Show Notes
In this episode of Startups For The Rest Of Us, Rob and Mike talk about five ways to structure your mastermind. They list some different formats to try and the pros and cons to each.
Items mentioned in this episode:
- ZenFounder
- Sherry Walling’s Retreat Book
- The Nights & Weekend Podcast
- Mastermind Jam
- The Productivity Project Book
Transcript
Mike [00:00:24]: In this episode of Startups For the Rest of Us, Rob and I are going to be talking about five ways to structure your startup mastermind. This is Startups For the Rest of Us, episode 277. Welcome to Startups For the Rest of Us, the podcast helps developers, designers, and entrepreneurs be awesome at launching software products, whether you’ve built your first product or you’re just thinking about it. I’m Mike.
Rob [00:00:25]: Hi, I’m Rob.
Mike [00:00:29]: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. What are you doing this week, Rob?
Rob [00:02:16]: Well you know how at the end of every year I talk about how email had become such a problem for me. That’s kind of the one thing I’ve haven’t been able to fix. I feel like I’ve outsourced or delegated or figured out systems for so many things, but my inbox was always the one, it’s just hammering me non-stop. I finally might have a solution. Basically I hired a VA about, let’s see, six or seven months ago. And it was more like, I’d say maybe a step up from just a standard VA, and it was someone who called themselves an Executive Assistant so I’ll call her an EA. And Executive Assistants are more used to dealing with executives, in essence, and it’s not like I’m some high-powered executive, but they are used to managing calendars and going through email and evaluating things, and being less about – there is definitely some process there but it’s also a lot of pretty hardcore thought put into it. And so the one that I had before didn’t work out. It became a little too much of a process and she was basically just filtering my stuff into some categories and it wasn’t actually helpful. I let her go a while back, she eventually became not liable. And now I have a new one who’s been with me for about a month and I’m slowly ramping more and more up. I have notices a dramatic difference now. Instead of waking up to 70 or 80 new emails in my inbox every morning, and then I get another 50 during the day or something, it’s just way, way less, stuff that I’m processing. Because not only is she filtering things, but she is responding to podcast invites. I told her my criteria, my loose criteria for evaluating invites for interviews and guest posts, and even some partnership stuff and she’s starting to take some action on those and inquire for more information or to let someone know that not able to do it or to actually book the thing, and then she has access to my calendar and she’s booking that. A long way of saying this week I’m feeling finally good for a brief glimpse about the status of my email inbox.
Mike [00:02:21]: Cool. I just have one question about that. Are my emails getting directly routed past?
Rob [00:02:59]: They definitely are. I said one of my things is if someone seems like they know me and they’re emailing me, just put them into the ‘Today’. ‘Today’ is everything I handled today. I get a lot of cold pitches for different things and I’ve asked her that if they’re cold that either evaluate it yourself or if you don’t know how, let’s talk about how you can evaluate it in the future, and then she puts it into a ‘This Week’ label. And I check the ‘This Week’ label once, maybe twice a week. And that’s where I have some newsletters that I like to read and some other stuff. And it’s people asking for advice as well, if I don’t already know them. Stuff that I just want to do in a big batch. Yes, since you know me, you would go into the ‘Today’ label.
Mike [00:03:01]: Well that’s good to know, I guess.
Rob [00:03:22]: The other thing, too, is I’m not having her reply as me at all. For some reason that feels weird. I know some people have a VA or an EA reply as them and that, I don’t know that I will ever want to do that. I’d prefer for her to basically send it over to me and I reply or she can reply but signed as her just to let someone know.
Mike [00:03:28]: I was going to say you could just have her do that and do the reply but then also sign it as herself instead.
Rob [00:03:28]: Exactly.
Mike [00:03:29]: That would work.
Rob [00:03:31]: How about you? What’s new this week?
Mike [00:04:33]: I was reading a new book over the past day or two. It’s called the “Zen Founder Guide to Founder Retreats.” And that’s by Sherry Walling. We’ll link that up in the show notes. I talked about founder retreats in my book as well, but it was based on an interview that I did with her and also, obviously, she was the source of that idea. So this is probably the definitive guide, I would say. It walks through four steps to making sure that you have a successful retreat and then goes through various strategies and activities that you should use while you’re on that retreat. And then it also includes some worksheets along with it. Like I said, we’ll link that up in the show notes, but I would definitely recommend that anybody who’s out there who’s considering a retreat or even if you’ve already gone on a retreat, there’s a lot of good tips in there. I especially liked the strategy section where she maps out four different strategies specifically for how to answer some of the questions that you have in your head, or how to go about goal setting. Again, definitely worth a read. We’ll link it up in the show notes.
Rob [00:06:27]: I was pretty happy with how this turned out. I did absolutely none of the writing. I didn’t write a single word in this thing. I did read it over for her and give her a little bit of advice, but she really drove it. And this is the first product she’s ever launched so I’m excited about it and she’s certainly stoked about it. If you go to ZenFounder.com there’s a link to it in the right navigation and I think she’s selling it for $24.00 via Gumroad. If you’re interested in it you should check it out. I have another recommendation for a book. It’s something I stumbled upon from listening to the Unmistakable Creative podcast. And the book is called “The Productivity Project.” I’ve listened to a lot of productivity books over the years and I’ve become immune to a lot of them and they have a lot of suggestions and tactics that don’t necessarily work for everyone or they just become advice that you don’t take. But what this guy did is he did, I think, a 100 different productivity experiments over the course of a year or a little more, and he basically looked at all the best advice and some of the worst advice and just implemented it and then he recorded all the results and he published it on a blog. And later, that turned into this book. So the book itself, I think, is 20 or 25 of the ones that worked the best for him. Maybe I’m 20% into the book and I had to stop listening in the car because I wanted to take so many notes and I didn’t want to take notes while I was driving. It has really resonated with me in terms of actually having actionable stuff and things that I have implemented so far this week. I mean I’m only three days into implementing these, but I want to see if I can make them sustainable because I think his suggestions and his insights are worth doing. Again, I’m not a huge fan of these productivity books because once you read one, if you’re not implementing the suggestions, then you should not read another until you do. But if you think you’re at a point where you really need a boost in productivity and you’re ready to start building some new habits, and I think that’s the key, then I would check out “Productivity Project.” It’s obviously on Amazon and Audible. I’m listening to it on Audible myself.
Mike [00:06:40]: I was just going to mention that when you pick up those types of books, basically if you make the decision to go down that road, you’re creating work for yourself because you have to commit to doing those things otherwise reading the books doesn’t actually do anything for you.
Rob [00:07:13]: Exactly. And I think I’ve listened to three or four approaches and I’ve noted down one, one and a half. I made a variation on the second one. And that’s what I’m going to do, is filter each one and say, “Am I going to do that? Do I think it will work, and B, do I have the discipline and the head space right now to start doing that?” And my hope is not to come away with 20 new ideas, it’s to come away with about three or four, and then implement one, make it a habit, wait about a month and then implement the second, make it a habit, wait about a month. So that’s my plan with it. But hopefully it helps folks out if you decide to listen to it. What else is going on?
Mike [00:07:49]: We have a question that came into us from Don Falcor [ph] and he asks us about using Medium. And he said, “Hi Rob and Mike. I’ve recently noticed a slew of folks who are using Medium as their content marketing platform instead of their actual site. I noticed that Drip is also doing this. My thought process is that I’m now losing control of the platform and I’m not able to provide a Drip pop-up or email marketing opt-in form and cross promotion since I don’t own the platform. Medium’s rather limited, and though it’s a fantastic tool for writing and sharing content, I can’t get past the fact that I no longer own the platform and I essentially lose the extra opportunity to cross promote and upsell a reader. The question is why do you use Medium instead of your actual marketing site?”
Rob [00:10:29]: And the answer for us is that we started it purely as an experiment. I’ve got quite a bit of content, let’s say between two and four posts a week and some of those – we put a post out today on blog.getdrip.com. It’s essentially a 3,000 word teardown with a bunch of screenshots of Derek Halpern’s recent email sequence that he used to sell his seven figure course thing. So we’re putting out pretty big pieces of content like that, and what we found is if we didn’t experiment and we ran it on our blog where we send the tweets to send people to the blog, and when we email our list we send people to the blog, and we did all that and we looked at the numbers. Then we tried a separate experiment where we still posted to the blog but then we posted to Medium as well. At the bottom of Medium we have two things. One, we have a link back to our blog that says “This was originally published here,” and we then have a call to action, “You can get this free email marketing email course.” They have to click through and there’s a landing page and they have to enter their email, so it isn’t as nice as being able to embed an opt-in form there. But the whole Medium post is there and so far we’ve seen no Google content penalties or anything like that, having duplicate content. In addition, then when we do the tweets and we do the shares and we send the email we refer people to the Medium post. It still exists on our blog, people can find it. But we’re sending them over there and the idea there is that you’re basically using your network to get noticed within the Medium space. The more hearts and more reads something gets, the more likely it is to get onto Medium’s list of popular posts today. And if you hit one of those then your stuff skyrockets. You get 2X, 3X the traffic and the views and the reads and all that. So that’s the idea, is you’re trying to utilize some else’s network. I totally agree with Don in the sense that you’re losing control if you’re building it solely on Medium. We’ve gone back and forth and we’ve run different experiments and what we found is that we do definitely get more traffic and more reads over on Medium. We also have found that they tend to be, I’ll say less qualified. So we get less interest, less people clicking back to our site because they’re not on our blog anymore, right. So there isn’t a Drip logo on the header, we can’t directly ask for the opt-in. There’s pluses and minuses here. I don’t have a definitive answer. We have not made a decision to go solely with Medium. I wouldn’t make that decision because I still want stuff to live on our blog. We don’t want to be a digital sharecropper where you’re basically building this community and this reputation but you don’t own any of it like Don said. I guess that’s a non-definitive answer to what we’ve done and the experiments we’re still currently running. And we were just evaluating one today. I was evaluating with our growth marketer Zack about which way should we go? Do we need to make a commitment to these because some we’re posting on Medium and then some we’re not. I didn’t realize, that was a long answer. It’s probably the shortest answer I could give.
Mike [00:11:25]: So Don hope that helps. Thanks for the question. In today’s episode what we’re going to do is we’re going to talk about five ways to structure your startup mastermind. And back in episode 167 we talked about how to organize and how to run a startup mastermind. So if you’re not a member of a mastermind group or you’re thinking about starting one but you’re not quite sure, go listen to that episode and you can learn some of the basics of how to get started. But in this episode what we’re going to do is we’re going to talk about the pros and cons of some different formats that you may or may not have tried in your own mastermind groups. This came about because in my own mastermind group, what we’ve started doing is we’ve started experimenting a little bit and talking about what different things we can do and how we can continue to use the people that are in the mastermind group to drive our businesses forward, but also to do some experiments, to not just mix things up so that the format itself isn’t stale but to help identify whether or not there are other formats that would work better for our businesses.
Rob [00:11:31]: So today we’re going to be talking through five different approaches for structuring your startup mastermind.
Mike [00:12:28]: The first approach is to use what’s called the round table. In the round table, pretty much everyone speaks for an equal amount of time for each session. Let’s say that you have a mastermind group with three people and you’re meeting for an hour and a half, then each person gets about half and hour. There’s a couple of different reasons why you might go with this approach. We started using this approach very early on just because it was the one we came across first and it just made sense. But one of the benefits of doing this approach is that pretty much everybody gets to speak every single time so everyone has a reason to go there. Everyone has a reason to show up because they are going to be getting valuable feedback for their particular business. And another reason is that you always get an opportunity every single time you meet to bring up the problems and issues that you’re facing in your business that were a little bit different where, let’s say you were skipped on a particular week or you got less time then you wouldn’t have those opportunities to talk about the problems that you’re facing.
Rob [00:13:46]: And to be honest, this is my preferred approach. I wouldn’t say it’s the best one but it’s the one that I’ve found that resonates the most with me because since we only meet every other week in the two masterminds we do, I’ve always struggled with if we do a hot seat one or a rotating hot seat, that I may not get to talk about my stuff for four, six, eight weeks, and that’s just too long given how much is going on. I think it depends. It’s certainly a personal preference and maybe it depends on what stage your business is at and how fast things are moving and how often you meet. But I’ve always really like the round table approach. I’m trying to think if I’ve even ever tried any of these other ones. I don’t know that I have. I think we might have done a hot seat one at one point and I didn’t like it as much as round table. But I do know that some people swear by the hot seat approach. And one of the cons, or the con, I think, the biggest con of the round table approach is that you may not get enough time, you may not be able to dive in deep enough into specific topics most of the time if you have four or five people in a mastermind and you only have an hour to meet, then you have like 12 minutes. So you really need to focus on what you’re talking about. I think the way I’ve gotten around this if by keeping masterminds really small, like three people, and then meeting for 60 or 90 minutes so that you have apple time each time. There are some trade offs here, but that, compared to the others, that would definitely be the drawback of round table approach.
Mike [00:15:17]: The second approach that I came across doing some research was essentially doing a timed segment. In a timed segment, what you do is you divide the call into very short time segments for somewhere between five and ten minutes. Let’s say that you have five minutes allotted to you, you can talk for those five minutes and then you get one minute to ask and answer questions, and then you get about a minute to transition to the next person. Now, in this, the nice thing is that you get to speak multiple times. So if you’re meeting for an hour and there’s three people, you’re going to get four different opportunities to speak or somewhere along those lines. Obviously those extra one minutes in there, but you get to talk several times in a row throughout the course of the conversation. And one of the other side effects of this is that if you forget to bring something up, you can bring it up later. What I’ve found in doing the round table is that if I go first, for example, then I might speak for my half and hour and then a little ways into somebody else’s turn speaking I might remember something. It does give you the opportunity to come back and bring something up that you might have forgotten about. The other thing that it does is it helps to keep the call on track without meandering a lot. I have had calls where the mastermind group will go long or will meander into discussions which are sort of meaningless, but if you have a strict timetable that you’re trying to stick to, then this can help alleviate those. And it’s not to say that you shouldn’t have fun during your mastermind calls, but there are certainly times where conversation will meander a little bit and an hour and a half call can turn into two and a half hours pretty easily.
Rob [00:16:19]: What I also like about this format is in essence it keeps you from having to listen to the same voice for 20 or 30 minutes. Studies have shown that if someone sits there and talks for no visuals for a solid 20 or 30 minutes that people, you almost naturally tune out. Our attention spans are only so long when it’s just one person talking. And so this breaks it up more and gets multiple voices into the system. I think this is a cool approach. I hadn’t heard of this one before. Obviously there are a couple cons to this one. I think the first one is that you need to be really focused to talk about your topic in only five minutes. Five minutes goes very quickly, and so if that’s all the time you have then you need to present an update and then maybe ask a question, and then you just have time for one or two people to weigh in and you have to move past it. And maybe the other con is that someone needs to be keeping track of time because if someone doesn’t have a timer going that beeps, you’re going to go long every time because five minutes is so short. You would have to be more structured and be willing to cut people off with this approach, but there’s the only two cons I can think of.
Mike [00:16:32]: It seems like you have to be much more, not just structured, but it’s very much more business like. It becomes less of a, I don’t want to say less of a peer scenario or friend scenario, but you’re a lot more businesslike about what you’re doing, what you’re talking about because you have to stick to that timer.
Rob [00:16:34]: Yeah, a lot of discipline to get this one going.
Mike [00:17:29]: The third way to structure your mastermind group is to have a short hot seat. This is similar to the round table in that every person still gets a chance to talk during that session, but one person is going to get extra time on the hot seat that week. And everyone else who is not on the hot seat is going to provide smaller updates. Let’s say that you’ve got three people in a mastermind group that’s a 90 minute call, one person might get an hour and the other two each get 15 minutes, so that would carry you through that 90 minutes. One of the benefits to this approach is that you get to have longer between your sessions in order to focus on your goals, and then during your hot seat you would provide larger updates when you are on the hot seat. If you have three people in your group and you’re meeting every other week, then it’s going to be six weeks to focus on your goals and buckle down, and then come back to the group and be on the hot seat about what you were able to accomplish over those past six weeks.
Rob [00:18:08]: There’s a couple pretty solid pros with this one. First is that you get longer between sessions to focus on your goals, and so you’re able to provide larger updates when you are on the hot seat. Because, as you said, you have a gap of like six weeks or eight weeks between times you talk so you can get a lot done during that time. The other pro is that you get to do one or two deep dives during your turn and get more detailed feedback. Because if you’re really on the hot seat for let’s say, 45 minutes or something, you can cover two topics, even three, pretty in depth. And you can explain a scenario, ask for feedback, get a good discussion, and then move on. There’s just a lot more time here to dive into some things that you might need help with.
Mike [00:19:08]: There’s also a number of downsides to this approach. The first one is that there are obviously higher expectations for you when you’re on your hot seat. For example, if you didn’t perform and it’s been six weeks since your last hot seat session, it’s really hard for the other people in your group to let that slide because you’ve had a number of weeks in order to work on that stuff and to get things done. The second thing is that it takes a lot more preparation for when you are on the hot seat. You really have to spend some time in advance of the call and make sure that you’ve got all your numbers laid out and you come to the group with some very explicit questions along with the data that you can present to them that will, essentially, give them some context about why you’re confused or why you’re not sure what to do at that point. So those two things definitely factor into the cons list. And this is an approach that we’ve tried in our own mastermind group. We’ve tried the round table first and then we went over to a short hot seat. And these are some of the things that I’ve brought out of that as cons for this particular approach.
Rob [00:19:40]: I think another couple cons to this approach are, one, that it can be easier to let things slide a bit during the weeks that you’re not on the hot seat. If you’re really going after strong accountability, then having six or eight weeks between each time you talk might not be optimal for you if that really is what you’re looking for. And the other con I can think of is that you might not get the ongoing attention you need if you run into a serious problem right after you have a hot seat because of the delay between them. Obviously you could always have email exchanges and get around that through other means, but that is definitely one of the cons.
Mike [00:20:42]: The fourth structure that we have here is a dedicated hot seat, and this is different from a short hot seat where a short hot seat, you still get an opportunity to speak every week. With a dedicated hot seat, each session is focused on a single person and that’s the person who’s the focus of the entire session. Obviously the benefit here is that you get an entire session that’s dedicated specifically to focusing on your startup and the problems that you’re having and being able to really dive deep into a lot of the issues that you’re facing. But that also comes with the drawbacks. And the drawbacks are that it could be several weeks before you give any kind of update to the group, and a lot can happen during those six or eight weeks. If you’re going to do an approach like this then it would seem to me like you’d probably want to also have another mastermind group that you’re part of that is not doing a dedicated hot seat approach. That’s where I think this would probably best fit in. I don’t think that it’s something that you can do alone. But if you do this in conjunction with some of the other mastermind formats then it would probably work out quite well.
Rob [00:21:15]: This is taking the rotating or the short hot seat approach to an extreme, I think. Obviously you get a lot of good time dedicated to your own startup and your problem when you’re on the hot seat. I think the cons here are again, there’s going to be several weeks between giving any kind of update. So that could be, I think, a real detriment to you. Also, it’s easier for someone to justify skipping a session because they’re just contributing ideas and really not getting much out of it. I think you’d have to have a certain kind of group and attendees if you’re going to do this, because if people start skipping sessions then it really isn’t going to work. It isn’t going to be an optimal mastermind at that point.
Mike [00:22:57]: And the fifth way to structure your mastermind group is to use a moderator. And if you’re using a moderator then I think what you’re going to want to is you’re going to want to bring somebody in from outside the group in order to moderate the call and drive those discussions forward. There’s a number of different benefits to this approach because that moderator can be used to ask the hard questions and help push for results from people. Sometimes it’s very difficult to put pressure on your peers because you don’t want to come off as being overaggressive or overbearing or even taking hot shots at somebody who came back to you and said, “I think this thing that you’re working on here is a terrible idea.” You can essentially have those things piped through the moderator and the moderator can help do those things. They’re also there to help mediate any personal conflicts between people, which hopefully in a mastermind group you wouldn’t have, but those things do come up on occasion. The moderator can help with that stuff as well. The last thing that a moderator can really do is they will do a better job than you probably would of tracking people and holding them accountable to their goals. And what I found that is in the mastermind groups that I’m part of, I tend to focus on the things that I’m working on and keep track of those things very well, but when it comes to what other people are working on, unless they bring it up, it’s very easy for me to forget something that they commented on or that they said that they were going to do a couple of weeks ago or a month or two ago because I’m so focused on all the different things that I have to do. Unless you’re very regimented and disciplined about keeping track of lists or checklists where people can literally check-mark things off and say I did this and I did this and did this, unless you are doing that kind of thing, it’s very easy for somebody to just let something slip through the cracks and then not notice it for weeks or even months at a time if you notice it at all.
Rob [00:24:34]: I think this is an interesting approach and I think this is the old style of running mastermind. There would be an info-marketing guru in the ’90s or the early 2000’s and they would say we’re going to have a mastermind and they’d get eight or ten people together and then I think they would moderate it or they would get one of their minions to moderate it, and then they would charge for it. And they’d charge a lot for it, to be part be of it. And I think there are arguably some value there to be given advice by someone who’s ahead of you, as well as to be around other folks. I’ve always had an issue with A, the overcharging of this stuff and, B, the fact that there’s eight or ten people in the group really is beyond me. I can’t imagine that actually being that productive. Since I haven’t participated in one, I don’t want to speak too strongly about it. With that said, I think there’s maybe a more modern approach to this in having a moderator in a smaller group of, let’s say, between three and five people. And still compensating that moderator, because I think that if you really are going to moderate, which means you’re not going to be one of the participants, then you need some type of compensation. And that may be monetary and it may be something else. But it has to be worth you spending the time to do all of these things that you said, tracking the meetings and asking the hard questions and mediating personal conflicts and all that. I don’t think it’s a sustainable model. I don’t think someone’s going to do it for a year or two if they’re just doing it as a volunteer thing. But I definitely see the advantages of using this approach, especially if you really do want to be all about business. Like you said earlier, it’s less of a discussion and maybe a hang out time and conversations between friends, and it really is a hardcore moderated business discussion with someone keeping it on track.
Mike [00:25:05]: I think one of the downsides that I can think of for this particular approach is that if the moderator ever is unable to make the call then the call is probably going to get canceled at that point. Because if you’re so used to having that moderator around to drive the conversations, you may very well find yourself a little bit lost if they’re not able to make it for whatever reason. And then there’s the obvious things of being able to compensate that moderator for their time. And then the other problem of some people are just really not qualified to be moderators so you have to have the right type of person who is filling that role for your group.
Rob [00:25:50]: I think another con to it is scheduling becomes slightly more difficult because there is another person involved in the mix. Easy enough to work around, but it is something to think about. I think another con to it is I don’t know anyone who’s doing it today. And so there’s no model for it. It would be experimental and you would have to spend some time to find that moderator and the experiment with it and figure out if it’s going to work and you’re kind of pioneering it. So it’s less about listening to what others have done and more about pushing into some new territory, which is not a bad thing, but it’s going to take time. It’s going to take adjustment and it’s probably not going to be optimal at the start. To recap, we talked about five ways to structure your mastermind group. The first was a round table, second was timed segments, the third was a short hot seat, fourth was a dedicated hot seat, and the fifth was using a moderator.
Mike [00:26:18]: And we mentioned it earlier on that if you’re not a member of a mastermind group, check out episode 167 where we talked about some of the basics of finding a mastermind group and setting it up and finding people. Something else that you can do is you can head over to a Web site called MastermindJam.com. We’ll link that up in the show notes. It’s run by one of the MicroConf attendees named Ken Wallace who also cohosts the Nights and Weekends podcast, which you can find over at nightsandweekendspodcast.com.
Rob [00:26:35]: And we don’t get any type of commission or anything like that from using Ken’s service. We just know that he’s a smart guy, working on this problem and trying to solve it for the community. And if I was looking for a mastermind today I would either go to my network or I would go to MastermindJam. This is a place you’re going to want to do it in the bootstrapping circles.
Mike [00:27:02]: And what he does with that service is he actually puts you together with other people who are in similar situations and who, based on the data that he has available to him, are probably going to fit well because they are in similar market verticals or let’s say, if you were building a SaaS company he would put you with other SaaS founders with similar revenue numbers. And he does that work on the back end to make sure that the group that you end up with is a good fit for what it is that you’re trying to achieve.
Rob [00:27:23]: And with that, we’re wrapped up for the day. If you have a question for us call our voicemail number at 888-801-9690 or email us at questions@startupsfortherestofus.com. Our theme music is an excerpt from “We’re Outta Control” by MoOt, used under Creative Commons. Subscribe to us in iTunes by searching for startups and visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening, we’ll see you next time.
Episode 276 | Handling Failed Payments, Cold Calling, and Staying Accountable
Show Notes
In this episode of Startups For The Rest Of Us, Rob and Mike talk about handling failed payments, cold calling, and staying accountable. These topics come from more listener questions and Rob and Mike share their expertise and advice on the subjects.
Items mentioned in this episode:
- Drip
- Blue Tick
- Churn Buster
- LeadFuze
- LeadGenius
- HostFamily
- Successful DJ
- Startup Stories Podcast
- FogBugz
- TeamWork.com
- Codetree
Transcript
Rob [00:00]: In this episode of Startups for the Rest of Us, Mike and I talk about handling failed payments, cold calling, and staying accountable. This is Startups for the Rest of Us, Episode 276.
Welcome to Startups for the Rest of Us, the podcast that helps developers, designers and entrepreneurs be awesome at launching software products. Whether you’ve built your first product, or you’re just thinking about it. I’m Rob.
Mike [00:28]: And I’m Mike.
Rob [00:29]: We’re here to share our experiences to help you avoid the same mistakes we’ve made. What do have this week, man?
Mike [00:34]: Well we’ve got an email from Will Samuels, who wrote in to us about our 2015 predictions, and he says he thinks that Rob was right on the storage. He gives us a link to … I think it’s hubic.com, it’s H-U-B-I-C dot com. They are a hosting provider, and they are, I believe the third largest in the world is what he says. According to the “”Way Back Machine, he says that back in March of 2015, they were offering 10 terrabytes of cloud storage for €120 a year, so that’s 5 terrabytes for $65.50. So according to that, Rob you were correct on one of your predictions last year.
Rob [01:13]: Wow, thanks Will, for writing in. Yeah, both you and I tried to look for some confirmation, or otherwise, from our 2015 predictions and it was kind of hard to find them and I think found some shady cloud hosting thing that did this, but I didn’t really want to call it good. So if these guys are the third largest in the world or thereabouts, I think that’s pretty good. Then when I made the prediction again for 2016, I can’t count that as a win, can I?
Mike [01:34]: I don’t think so. In fact, they’ve actually dropped their price, so 10 terrabytes is no longer $130, it’s more like $65 or so at this point. They’ve dropped the price since then, yeah, so 10 terrabytes personal cloud.
Rob [01:47]: Let’s be honest, this is kind of a gimmee. Every time you’re predicting that storage is going to get cheaper in the next year, it’s kind of obvious; like processors are reading it faster, phones are going to get better cameras and high resolution screens. This is not that interesting, but the fact that the price point was actually under that exact point is kind of cool. That’s a lot of storage, man. Five terrabytes, or now I guess, 10 terrabytes for that much?
Mike [02:10]: Yup.
Rob [02:11]: So, I’m running some split test right now on DRIP, on the homepage, and other pages, to try to nail down some messaging. We’ve had the same positioning and messaging for a long time, and I just want to see if something else resonates, because we’ve changed so much over the 18 to 20 months since we really nailed down that headline of “lightweight automation that doesn’t suck”. and I’m wondering if perhaps different ways to phrase that that might resonate with the current traffic to come rather than … the last split test I ran was 18 months ago. S, I always find split testing — I feel like it’s pain to get set up, even with something like Optimize.ly, but man, it’s so much fun. It’s so much fun when you hit Start and you’re just excited. Every morning, I wake up like a kid on Christmas and look at the results to see, is something winning?
Mike [02:52]: I thought you were going to say you’re excited to look at the credit card bill and say, “Oh, I just lost a thousand dollars yesterday.”
Rob [02:57]: Oh nice. Well, that could be the other thing, I guess, right? Like, “Doh! I totallt hosed it.” Yeah, I definitely a keep a close eye – when something like this, when it’s on the homepage, or it’s a high traffic page – I like to keep a pretty close eye, and tabs on it, because you’re right, you can, kind of, screw things up pretty bad pretty quickly, I think.
Mike [03:15]: Yeah, funny you mentioned that, because I’m just kind of in the final stages of finishing marketing plan for my product, Bluetick, and that’s kind of one of those things that I’m looking at pretty heavily right now, is to figure out what should the exact wording of the messaging be. I have my personal favorites picked out, but I’ve also got a list of about 10 different things that I want to go through and start testing to see what resonates with people, and whether or not those things take people through and convince them to actually sign up for, like a mailing list. So I’ve got to look through those, and do some split testing myself, and see what comes out of that, because whatever you think may not necessarily be the winner. It may be, but at that point, you’re just spending $1,000 a day or whatever, but it will be interesting to figure out what happens and what comes out of that.
Rob [03:58]: If I were you, I wouldn’t start with all 10. I would go back to the people who have already bought from you and run those by them and have everybody pick up their top one or two, and then try to aggregate a few from there. Because it seems like you already have a little bit of an audience, and if you have a mailing list as well you could toy around with that. If you felt like sending people an email or ask them to choose how they would describe it, or something like that. It might give you a little leg up so that you don’t have so many things to test, because you need a lot of traffic to test that many options.
Mike [04:30]: Right. I don’t think I was planning on going through and testing all 10 of them, but it also kind of puts in my head the idea that if I go to those list of 12 or 13 people that have place preorders so far, I’ve got their language, so I will essentially be finding more of those people, which is not necessarily a bad thing, but it’s also a very self-selecting group. I wonder if there are other groups out there that it would resonate more with. I don’t know the answer to that, but I’m also not sure whether or not that makes a difference at this point, and I don’t think that it does.
Rob [05:00]: Yeah, yeah. You’re pre-launched now, and so I would focus on super small vertical target market, and if selecting now, then that’s actually good. Because if you go out and try to get multiple groups of people in there, then they’re going to be asking for different features, and it’s going to conflict. I would imagine you have small entrepreneurs and solopreneurs and single founders and probably some bootstrappers in there, that type of thing. If that’s where it’s working right now, I would focus on that for the time being until you feel like you’ve tapped that market out, rather than trying to expand out. Maybe it’s not even premature optimization, but it’s just going to be time consuming to try to do this, when I think there’s other stuff that you could better spend your time doing.
Mike [05:44]: Yeah. Either way, I still have to go out and start doing … I want to start doing some paid acquisition to start acquiring email addresses that I can start building up that mailing list. I think that tying back some of the messaging into that is probably wise at this point. It would at least give me some data points. But you’re right, I don’t think just testing all of them would probably be a good idea at this point. I haven’t really gotten to the point where I’m going to actually pull the trigger on that. I’m just starting that process now.
Rob [06:11]: I think I realized when you said dropping a thousand dollars a day, you meant on ads to split test, right?
Mike [06:16]: Oh yeah.
Rob [06:18]: Okay, because right now you don’t have any organic traffic yet. No, the DRIP that I’m doing, I’m not running any ads to this. This is all the organic traffic that comes through. We get a bazillion visitors a month, so it’s actually going to be pretty easy. I was thinking you meant, when you said losing a thousand dollars a day, I was thinking you meant that if you run a split test and one of them is doing really poorly, that you lose the trials and therefore lose the thousand dollars a day.
Mike [06:39]: Got it. no. I haven’t even thought about that, but I was kind of operating under the assumption that you were going to be doing paid advertising for those split testing, but it makes sense.
Rob [06:47]: Yup, cool. Hey, we have a bunch of new iTunes reviews. Can’t read them all, but I’ll read a couple here. This is from Jerry Weir. He says, “Great show, value in every episode. If you’re at all into starting your own business alone or in a team, you really shouldn’t miss out subscribing for Startups for the Rest of Us. Actionable advice in every episode.”
Then we have one from Prof. Duchamp. Five star review from the US. It says, “Listen or miss out, you choose. If you’re doing anything related to startups, you would be plain silly not to listen to this podcast. Mike and Rob do a really job of exploring the minutiae of building a platform. It’s not about interviewing the biggest names in the industry, or even talking about the trending topics. They get into stuff that really matters. Keep doing what you do.”
Lastly, from Zephron ADR, from the US, he says, “Great content for first time entrepreneurs, great knowledge, thanks for sharing.” We have 462 worldwide reviews in iTunes, and we’re looking to get that number up over 500, so if you haven’t ever given us a five-star review, it would be awesome if you could. Log in to iTunes, hit that five-star. Even if you don’t write a full review like these folks did, you can just click the five-star and it will greatly help us out. If you feel like we’ve given you some value, it would be great to get some back.
Today, we’re answering some more listener questions. We had some really good questions come in, the first one is from Don Felcor, and it’s about handling failed payments and dunning. He says, “Hey Rob and Mike, I’d love to hear how you guys handle subscription problems that relate to failed payments. For example, if you use the default Stripe subscription system, you have three options after the user’s payment method fails three times. Those three options are to “cancel the subscription, to mark it as unpaid, or to leave it as is.”
By default, Stripe selects “cancel the subscription”. I feel this is bad mojo because you then lose the subscription that you worked hard to get. Therefore, I’ve changed it to mark it as unpaid so I can follow up with the customer. Given the other options, what would you recommend SaaS companies do in this case?” Then he has a follow up question. Maybe we’ll answer this one first, and then look at that one later. You have any thoughts about this?
Mike [08:42]: It seems like that’s the way that it should be handled. You don’t necessarily want to just make that subscription go away. You want to go back and talk to those people for a couple of different reasons. One is that it could just be that the credit card failed because it expired or their account was hacked so they got a new credit card. There’s a lot of different reasons for the credit card to fail. So it’s not necessarily uncommon for those things to fail three times, but there’s also a lot of cases where customers have decided, “Hey, I know that my credit card is expiring. I’m going to use that as an opportunity to essentially wipe the slate clean on all of my paid subscriptions, and anything that I really want to renew or that I depend on, then I will renew it.”
Those are the types of people that you probably want to reach out to, that you can at least get some sort of feedback about why it is that they cancelled or why it is that they chose to go in that direction. A couple of other options for getting those customers back…I mean, obviously you can send some sort of dunning email to them if you’re not doing that already, but there are services out there like Churnbuster or Stunning.co that you can use that will go out and try to get those people back for you as customers. It really depends on whether or not you want to be the one reaching out to them or if you’re at a scale where…I don’t want to say that their feedback to you doesn’t necessarily matter, but it is less important to you to hear the specifics of what it is that those people are saying. Those other services might be an option for you if you have other things that are a little bit more important to you than listening to the specifics of what their feedback is.
Rob [10:08]: Yeah, I think the meat of Don’s question is about whether after three email attempts – because that’s what Stripe does, right, it’s built in that they email three times and you can set the intervals. And after they haven’t responded, or updated their card after three attempts, do you cancel the subscription or not? Don says he doesn’t, and that he then wants to touch base with them.
So in my experience of trying to do this manually, and I did this with HitTail for a while in the early days, just because I didn’t know any better and I was experimenting and trying to get the people back. If they didn’t respond to the three credit card expiration emails, I never got a response to a personal email. Either they weren’t getting the emails, they didn’t care about them, they were going to spam, they’ve abandoned the inbox — there was just something, where if they’re not going to open or come back after three emails, I never… and let’s say I emailed by hand maybe 20 or 30 people. It’s not thousands of people, but it was enough that I stopped doing it, because it just was a bad use of my time. So I didn’t get good results from there.
With that said, I think that if you have phone numbers, and you can reach out, I know that that is dramatically more effective. I saw an article by [Allan?] at Less Accounting, where he talked about – this was a couple of years ago – but he talked about, I think it was like his sister doing basically dunning phone calls to people, and that they dramatically changed the number of people who gave them a credit card, and basically an updated card number.
That’s my thought. If someone doesn’t respond to three, and you’re just going to send them another email, I actually don’t think it’s worth it, and I would put their subscription into cancelled mode. Now, with DRIP, we wrote our own engine. We didn’t use the Stripes subscription API, we just used a [bare?] charge API, and as a result, after three emails — I think it’s three, maybe it’s four – your account is pending cancellation, and if you come back and try to log in to that account again, then it says “Hey, your card expired, or your account is cancelled, Just enter a new card here and we’ll get you started again.” It is easy to undo that, and I’m not sure if it is with the Stripe subscription API, because obviously we don’t do that.
Mike [12:06]: I’m not sure if Stripe actually sends those people emails if their payments fail. I think that it initiates a web hook – or you can have it initiate a web hook back to your site – but I don’t know that it actually sends them an email on its own.
Rob [12:17]: Oh got it. Okay. Thank you for that clarification. Absolutely then, I would capture that web hook and send some automated emails – whether you use Stunning or Churnbuster, or whether you just write some code to handle that web hook instead of emails – that has to get done, yes. I don’t think that you – even at a small scale – you don’t want to handle this manually, because it’s going to happen a lot more than you think.
Mike [12:39]: I really like the idea of capturing the phone number and getting in touch with them. It just sounds to me like that’s something you would probably want to do much earlier on in the cycle of them becoming a customer. So maybe a week or two weeks after they’ve become a customer, you pop something up and ask them for their phone number. And you can use that – maybe bribe them in some way, shape, or form. Either you give them an extra amount of service, or discount, or free white paper, or free consultation, like that, in order to gather that information, so if it does happen down the road, then at least you’ve kind of planned for it in advance.
Rob [13:10]: I’m glad you said that. It reminded me of what I did with HitTail. We do something similar with DRIP, although we do it during the guided set-up. We’re asking some other questions, and we do ask phone numbers and say, “We’re going to contact you for billing purposes.” It’s not required, but we get a good response rate to that. With HitTail, I’d coded up this form where it was like every fourth or fifth time you logged in, if you didn’t have a phone number, it would do a little pop-up, and it would say, “Hey, just in case your account gets messed up, can we ask for your phone number? We’ll use it for billing purposes.” We got a nice chunk of phone numbers, and then I went – this is before Stunning and Churnbuster, right – I went and I got an account with, I think it was Coalfire, and they basically do Robo-calling through an API. In essence, I recorded a 45-second call from me, it was just like, “Hey, this is Rob, I’m the owner of HitTail and your credit card is expired, and blah-blah-blah. Go to hittail.com/account to update your credit card.” Something like that. Then that would then fire, after all the emails had gone and people weren’t doing it, then it would put them into a call thing and they would basically get an automated call from me. Most of them hit voice mail – you can see how many hit voice mail and how many didn’t. But the impact of calling versus just emailing was substantial, I will say. I don’t want to give exact numbers, but it was substantially better. Even with Robo-calling, which is not going to be nearly effective as actually having someone do it. So if you’re at any kind of scale, you’re definitely going to want someone to help out and actually make the phone calls.
Then the second part of Don’s question, he says, “On another note, I know from conversations with Derek,” – that’s my co-founder with DRIP – “that he built the billing system for DRIP from the ground up, and it does not use Stripe-built subscription system. If you’ve built it that way,” – which we have – “how do you guys handle this kind of stuff?”
To be honest, we handle it similar to Stripe. We basically just, we retry, and if it fails, then we email. If you notice – I don’t think we’ve ever gotten our dunning emails. I think they might be published on the Stunning.co blog, to be honest, because he did a dunning series. They may have changed since then. But you’ll notice that they’re not shaming, and they don’t sound like they’re coming from a Fortune 500 company. They’re very much personable, and they’re like, “Hey, this happens to everyone sometimes. No problem. All you have to do is…I mean it’s just like talking like a person. I think I sign it as a co-founder of DRIP.
We do that a few times, and like I said, they go into cancellation. They can come back after any length of time, frankly, and reactivate the account. They just have to enter their credit card and make that payment. So thanks for the question, Tom. That was a good one, I’m glad we’re able to discuss it today.
Our next question is from Glenn at archived.io. It’s about cold calling, and he says, “Hey Rob and Mike. I’m in the very early stages of business development. I was wondering if for your B to B businesses, in the early stages, did you do much, or any, cold calling, or possibly cold emailing.” Then he addressed something to you, Mike. He says, “How did you go about finding the prospects to interview while you were doing customer development with Audit Shark.”
Mike [16:00]: So back when I was doing sales level, what I found was as I was trying to do cold calling it generally didn’t work very well for me. What I ended up running into was the fact that, in much larger size accounts, what tends to happen is that those types of accounts have enterprise sales reps who are talking to them from Dell, and HSI, and Tiger Direct, and HP, and places like that, and they’re all basically in the door. So, unless you’re talking to those people, and you’re getting introductions from those people, it can be very difficult to get anyone’s attention.
That tends to be more at the manager, or director of IT, level. I wasn’t trying to get in at the lower level people, like the end engineers or things like that. Although I did try to do that as well. I never had much success with it, but it could be just a matter of either the calling scripts that we were using, or the types of people that we were calling, and the leads that we ended up dredging up. It honestly just didn’t end up working very well for me. I do know that there are people out there who are making it work, and they’re doing extremely well with it, but they’re also in, I would say, different businesses where their products are not necessarily aimed at the IT department. So I can’t really speak outside of the IT department, because I haven’t done anything with larger companies outside of that area.
Rob [17:20]: I have not done cold calling in the early stages of a product – frankly in any stages of a product. I did used to do some cold emailing outreach, but it’s very, very specific, when I was consulting and contracting. I would email designers and other folks, to try to get work, and that actually worked pretty well. I mean, if you really hone it, and I wouldn’t email a hundred or 200 people. I would email like 10 in our local area and I would say, “Hey, here’s what I am. I can be your outsource developer, blah-blah-blah.” I had a pretty well-written email that got me some leads. I think cold email like that can actually work reasonably well. The other option is something that’s pretty popular these days, with the publication of Predictable Revenue – which is a book by one of the guys who helped grow Salesforce – is this cold outbound email to these large lists. So you can use a service like LeadFuze, or LeadGenius, and they will put together a lead list based on your criteria, and they will email them. If you don’t have the budget for it, you can totally Google this and people will show you how to do it. It’s not that hard, it’s just a lot of manual, grinding work, because you can’s mass email this lists. That’s spam, but if you send each email individually using a tool like Tout or Yesware – there are a lot of tools in that space – and you customize the email reasonably well, you can actually get some traction here and get some demos if you have a decent value proposition.
So I wouldn’t say that cold calling is dead, or doesn’t work, or anything like that, but I don’t think it’s a good use of your time, necessarily, early on, unless you really are trying to access a market where a cold email isn’t going to work. Maybe if you’re selling to realtors, or you’re selling to someone who is by the phone all the time and is going to pick up, I think that might have some legs. I think that may be the best way to get a hold of them, because in general, realtors tend not to respond to emails. If you’re marketing to designers or online marketers or software developers, or something, cold calling is probably not going to be a good way to do it, and you either got to do it through cold email, or frankly, just getting some semi-warm introductions. I think before I’d start doing cold stuff, I would think about running ads to a landing page and getting some prospects there. You get 10, 20, 30 emails and you don’t then have to go outreach. You can just basically say, “Hey, you’re interested in this. Let’s talk more about it.” That’s an interesting idea.
Another one is to think about going to your network before you try to do cold outreach that’s so time intensive, and trying to figure out if you know people who can recommend others who might be interested in this. So I think there’s two ways to think about this cold outreach. It’s like in the early stages of your company, when you’re just doing customer development and you’re just trying to figure out what to build, it’s not going to scale. But yeah, I think that maybe you should consider doing it if that’s really what you need to do and you can’t figure out a way using ads or using the network to get around it.
Then in the later stages, once the company’s growing and you’re looking to scale, I think that cold emailing has, kind of, been proven to be an effective medium. For the time being, anyways, everyone’s getting into it, and when everyone gets into these marketing approaches, they tend to stop working. I’m getting so many cold emails now that I’m already seeing the effectiveness of them drop. So I think, like infographics and like – what was it five years before that – certain things come into vogue, and then they go out of vogue. I think that cold emailing will be around, but I think it’s effect in this – especially with the technorati, who are getting all these same emails from everybody – I think the effectiveness of it is going down and will continue to do over time.
Mike [20:50]: One thing that you mentioned in there that I want to expand on was the idea of asking for introductions to people. I found that that works extremely well, especially if you find one person who is interested in what you have to offer and is interested in talking to you. So even if you don’t have a product yet, and you have one person in your network that you can talk to, you can ask them for an introduction and say, “Hey, are there three people that you can think of that you can introduce me to that might have this particular problem?” If they can’t get you one right away, I think that there’s a couple of videos from [?] talking about exactly this thing, where even if they say no right away, just say “Okay, just give me one. I just want one,” because that one person can lead to three others who are not in your personal network. And after a while, when all of those roads start pointing back to the same people, then that method has probably been saturated to some extent, because when I was going through this for Bluetick, I was asking that exact same question of people. What I found was that there’s one person who’s several people in a row would start recommending me back to him, and I’m like, “Okay, well, this network of people is probably, at least, a little bit saturated.” Obviously, I didn’t go through every single list of everyone that I had access to, but I got to a point where it was obvious that a lot of people were pointing back to the same people.
Rob [21:53]: Good question, Glenn. Thanks for sending it in. Our next question is a voice mail from Rudy, and he’s asking about starting two product ideas at once.
Rudy [22:01]: Hey there, guys. This is Rudy. I own [?] I have a quick question. I’ve been [?] for a little bit of a short while now, and I ran into a problem and some people then came up with a product idea for the solution to that problem. As guys that are involved with multiple ventures, and kind of dabble in different projects. What’s your advice on trying to manage maybe starting two product ideas at once, or trying to build something that would both solve your present need with a different existing business, as well as solve other users’ needs in different niches. Thanks.
Mike [22:41]: I think the technical term for this is Objectivius Shinium Syndromus, which is Shiny Object Syndrome.
Rob [22:47]: Yeah, the scientific name.
Mike [22:49]: There’s a scientific name for this.
Rob [22:50]: Episode 170 of this podcast, 12 Strategies for Avoiding Shiny Objects Syndrome. That’s exactly what I was thinking too.
Mike [22:55]: Yeah, it just seems to me like, yes, it’s a problem that you kind of need to be solved, but if you’re looking at it as something else that you can build, it’s very easy to get distracted from what you’re currently working on. It’s also very easy to let your attention, kind of, drift off to those other things.
Now, if your current business is kind of stalling out, and it’s not because you’re getting distracted, then maybe it’s worth looking at that as kind of the next area that you’re going to go at, but it seems to me like trying to build something like that and making it into a full-blown product is probably not a good use of your time.
One of the things that come to mind is Rob with DRIP. Very early on in the stages of building DRIP, what you had wanted to do was you wanted to be able to collect email addresses on the HitTail website. So you built this little widget that you could install onto the site to help collect email addresses and send them into an email campaign. That eventually turned into what is now DRIP, but you didn’t let that distract you too much from building on HitTail. You still buckled down and got everything on HitTail that you needed to do, and you didn’t turn that into a product until you had made the conscious decision that, “Hey, I’ve taken HitTail really as far as I want to go right now, and I want to go do something else, because everything is fine here and I just want to build a different product.”
So it seems to be like this may very well be one of those situations where if you build something, make it something for you, make it something you use internally, and if it gets you to where you need to go with your current products, awesome. But I would not spend any time and effort to build it out into like a full-fledged product for other people, because that involves a whole world of other problems that you’re going to need to dig into.
Rob [24:42]: Yup, that would be my advice as well. I think that it’s easy to see something and think of it as going to be more fun or easier than what you’re working on now. If you are ready to completely abandon what you’re doing now, then I’d say consider this. Because in essence, your summary of the HitTail to DRIP transition is mostly accurate. Basically, Derek was contracting for me at the time and he built that little widget. I was at the point where HitTail was already – we were not starting out. It was already generating somewhere between $20,000 to $30,000 a month, every month, as a SaaS app. Given the return and a bunch of other factors, I saw that it was topping out. I could have pushed it further by really digging in and building a bunch more features and doing a whole revamp, but I started evaluating the landscape, the SEO space, the [not provided]?. “There’s just a bunch of things, factors that are coming into play, and you know what? I think I’m kind of ready to move on. I think I’ve accomplished a lot here, and I’ve learned a lot.” And I was ready to move on to another business. I did keep HitTail running on the side. It declined over time, slowly, but it was able to fund the next project, which is now bigger.
Even that, trying to manage two things at once- trying to grow one and manage another – was a challenge. I would be very, very hesitant – not just hesitant, I would never start two projects at once. Don’t try to grow two things at once. That’s my unequivocal advice, is not do that. Owning two things at once is doable, if you get someone to manage one. As long as you’re not trying to grow both of them at once, because it’s the growth that really takes the founder and the creative thought, and it takes some mental energy. If you split that between two things, neither of them is going to go very far. If you’re thinking about building this other product, I would abandon the first one. That’s a decision that you have to make at this point.
All right, last question for the day is another voice mail. It’s about how to manage a project from conception to completion.
Bran [26:25]: Hey, what’s up guys? Big fan of the show. This is Bran from successfuldj.com. What my question is is about project management. I was listening to a little bit of the startup documentary, Rob. I just want to say that was awesome. Thank you for putting that out. But I’m curious about how you guys do project management. I was hoping you could do an episode where you walk us through how you go from, let’s say, the concept of DRIP to the creation of DRIP. I know you did that in the documentary, but if you could take maybe a smaller project and concept, and just give us some ideas in terms of software you use – [?], Trell, to do it, whatever it is, and some mistakes you made in the past with project management, and how you just keep everything streamlined and efficient in terms of breaking things down into small pieces, and what to put on the “to do” list, et cetera, et cetera. Keep up the good work, guys. I’m loving the show as always. Talk to you later.
Rob [27:20]: To clarify, he mentioned the Startup Documentary. That is the documentary that Derek and I recorded. It’s an audio documentary, as we were building DRIP, over the course of 9 months. That’s at startupstoriespodcast.com if you haven’t heard that before.
Mike, the reason I wanted to talk about this in this episode, instead of doing an entire episode around it, is I actually think it’s a lot simpler than most people think. I think he asked for mistakes that we made, and the mistake that I made in the past is putting too much process, or going too heavyweight. Seeing someone break out Microsoft Project to manage a three- or four-month software project. I have a couple of tools that I use pretty loosely, with some light process around it in order to manage features or even entire DRIP process. But I’m curious to hear, before that, what you use. Because right now, you’re in the middle of building Bluetick. What kind of tools and process you have set up?
Mike [28:13]: Sure. I think there’s two different aspects to this question that, kind of, came to mind when he was talking about it. The first one is what tools do you use, and how do you basically manage the flow of data back and forth between them. Then the second piece of it is, how do you decide what to do, and when? I think that those are related things, but the tools do not necessarily dictate what you’re doing and what order. They can, especially if you were to use Project, or anything like that, where you can put up cascades between one task and the next.
For what I’m doing now, I use probably three different tools pretty extensively. The first one is FogBugz, which is where all of the development tasks go. So anything that is related to code, or back end or front end application changes, all of that stuff goes in FogBugz. Everythig that’s basically product development oriented goes in there. I manage all of that code, and all the various sprints, and what we’re working on, all of that goes in there.
For all of the marketing stuff, I have a teamwork.com account, and I actually have two different projects that have been there. One for the engineering team, which I did not expect them to use, and they have not used at all yet. So it’s there if they need it, if they need to share files or whatever, but we also have kind of a Dropbox on the back end that everybody has access to the same sharer. So if they really needed to share larger files, they could, and it’s all connected to my account, so it counts against my storage space. Then I also have inside of Teamwork, I have a specific project set aside for just all of my marketing tasks.
Now the other thing that I use pretty extensively is a Goggle Doc, where I put together a marketing plan for Bluetick. What I did is – I actually have been working on that for the past couple of weeks. I sat down and I decided what my goals are, how am I going to get there, what the product is, how do I describe it to people, what are some of the descriptions and potential headlines that I used, what are the concerns that people have about the product, why would they use it? I have stuff in there about pricing, and all these other things that go into the marketing document. But most of them are really just notes. They are things for me to look at and review, and think about how I want to address that problem, or some of the different ideas or thoughts that I have about that particular piece of it.
Then what I do is I take those things and then I translate them into my Teamwork account and say, “These are definitive things that need to be checked off as something to do.” For example, in my marketing plan I might have the idea of hiring writers. Then I have like a bunch of different job boards, or places where I might find writers. Then I take that over into my Teamwork account and I write it down and I say, “Okay, if I’m going to through, and I’m going to do a content marketing campaign, these are the places that I can go and evaluate a writer. But, one of my tasks is going to be to go each of these things, do a little bit of research, find a writer, and then hire them.” Then it then leads into the other tasks. The document itself is really just for me to kind of basically spew out all of my different thoughts on a particular topic, because Teamwork is much more for lists of tasks, and being able to iterate through those. There is like a notebook section, but because it’s not really tied over to the tasks section it’s a little bit more difficult for me to use it in that way. So those are the tools that I use in terms of process. I kind of start from that marketing plan document and decide what needs to be done, and then it goes over into Teamwork. Again, all of the software development stuff gets managed directly through that other side of things inside of FogBugz.
Rob [31:44]: For me, when I’m first starting a project out, I don’t use any type of issue tracking. I go into basically a Google spreadsheet, or an Excel — it used to be an Excel spreadsheet — and sit down with a developer, or if I’m building it myself…I forgot what are the top objects. Typically if it’s a web app, I look at web pages. If it’s a mobile app, I would look at screens. If it’s a desktop app, I’d look at screens or forms, I guess you’d call them. Then I’d try to throw some time in there for database development, and some project management, and database design, and that kind of stuff. Then go right to the screens and say, “How long it’s going to take to build each of these?” And throw estimates at everything in a big Excel spreadsheet, or Google spreadsheet these days. Then start working and deduct those as I go so I know where the project is. So it’s basically an entire project tracking mechanism just within the spreadsheet.
There are some more exotic stuff you can do that I’ve talked about in the podcast before, but you basically can say how many hours a day you’re working on it, and then you can set a date, using – there’s a workday function – where it just automatically tells you when you’re going to deliver this, based on how many days a week you work. So If you don’t work a few days, it just continues to push the date out. You can physically see at the bottom of that Excel spreadsheet continually getting pushed out. It’s pretty motivating when you see that.
The reason I do that, instead of stuffing everything into an issue tracker, like a FogBugz or Github Issues, or Codetree, is because early on you might have 50 things that all have to get done, and you’re kind of just hammering through them. I don’t want to have to update 50 issues independently. I’m just trying to aggregate everything, because you really are coding this in a block, right? And this is maybe a three- to six-month project, and if it’s one or two developers just sharing that doc with someone working with them like me basically driving the project, this is I found to be a lot more efficient than having every individual task in a tracker.
Once we start getting towards the end and it becomes more of a punch list thing, we were actually looking at maybe 10 or 12 individual tasks left in order to get to a certain milestone, and then you really do need to start measuring stuff, that’s when I switch over to more an issue tracker and enter them individually. Of course, at Drip we use Codetree, which is built over GitHub issues essentially. It’s like a nice sprinkling layer on top of that that helps your prioritize and do other stuff.
That’s really it. I’ve never been a fan of the heavyweight project management tools. I think, if you are managing 10 developers, or you’re on a big enterprise team where you have a lot of communication, you do need it. You know, you’re a big company. But for small startups, the gift that we have, or the advantage that we have, is that we move quickly. I’ve found that a lot of the PM tools that I’ve seen tend to weigh you down a bit more. Now with that said, I still have not tried Teamwork. I have an account that we got for MicroComf Europe, and I do want to try it, because I’ve heard so many good things about it, and I know that Peter and his team have certainly built something good there. So I’m tempted to do that, perhaps for a future project. So I think that would be the one othercaveat I would lend to it.
Mike [35:05]: Yeah, I think that in terms of the development side of things, I think that it’s more a matter of personal preference than anything else. There’s no right or wrong answer, it’s what works for you. What I was running into was that for the development team that I’ve got working with me on Bluetick, I wanted them to basically handle everything. Because of that, when I took all the different UI mockups that I’ve run through people who have placed preorders, I took a PDF of those mockups, sent them off to the development team and said, “Look, this is what you’re going to be responsible for building, and I want you to give me a time estimate of how long it’s going to take you to build each of these screens.” From those, they were able to break those down into individual tasks inside of FogBugz, and apply an estimate to those and say, “Okay, to put the screen together is going to take me, let’s say, two hours or three hours or whatever. And then to wire it up is going to take another hour. And to do unit testing. or whatever, it’s going to take another hour on top of that, whatever those numbers happen to be.
What that did for me is it allowed me to go from there and then look at the total report and make sure that none of their task estimates were more than four hours. If they were, I could go back to them and say, “Hey, you need to break this down a little bit further, because we need to be sure that this is probably more accurate than not.” Then using that information, I was able to go back in and, kind of, look at a report and say, “Where on the timeline is getting all of this stuff done going to fall? Is it going to be closer to four weeks, is it going to be closer to eight weeks?” Just having all of those hours added up was really helpful. The point is really what those hours add up to; how you do it, whether it’s in FogBugz or in a spreadsheet, it is almost immaterial. It’s more a matter a matter of personal preference than anything else.
Rob [36:17]: I think that’s a good point. It’s like, don’t get hung up on the tools. Seth Godin will often not talk about the tools he uses to write, because he doesn’t want everyone to try to use the tools he uses to write, because that’s not what makes him Seth Godin. I would say the same thing with project management. You can ask for advice, you can get a suggestion, try out a couple of different approaches. Obviously Mike and I have very different approaches. Try out both of them, and just pick one. Don’t go looking for the tool that’s going to make your project succeed, because it’s not the tool that’s going to do it. It’s you and your developers and your team that’s going to do it. You can even use some pretty shoddy tools and get some good work done. It’s happened in my career, where we’ve been forced to use things that don’t work that well, and you can still produce good product. Other times you can use the best tool available and you can turn up crap. It’s really much more you and you’re team in terms of actually getting things done on time.
Mike [37:00]: I think that about wraps us up for today. If you have a question for us, call it into our voice mail number, 1 888 801 9690, or you can email it to us at questions@startupsfortherestofus.com. Our theme music is an excerpt from ‘We’re Out of Control’ by MoOt, used under Creative Commons. Subscribe to us on iTunes by searching for startups in business, and visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening and we’ll see you next time.
Episode 275 | How to Influence Decision Makers on Your Pricing Page
Show Notes
In this episode of Startups For The Rest Of Us, Rob and Mike talk about how to influence decision makers on your pricing page. Inspired by a listener question they give you some tips on how to optimize for better conversion.
Items mentioned in this episode:
Trancript
Mike [00:00]: In this episode of Startups for the Rest of Us, Rob and I are going to be talking about how to influence decision-makers on your pricing page. This is Startups for the Rest of Us, Episode 275. Welcome to Startups for The Rest of Us, the podcast that helps developers, designers and entrepreneurs be awesome at launching software products. Whether you’ve build your first product or you’re just thinking about it. I’m Mike.
Rob [00:25]: And I’m Rob.
Mike [00:26]: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. How you doing this week, Rob?
Rob [00:30]: I’m doing pretty good. I’m feeling excited and, I guess, relaxed to be on the other side of my launch. Last week’s podcast episode, Derrick and I talked about launching the big feature in Drip called “Workflows”, and I feel so much more relaxed now. Trials are coming in. We’re going to look to have the biggest month of growth we’ve ever had, and it’s like you have two fears. I feel like I have two fears when I launch something like this. One, that the feature itself somehow isn’t going to work, right? You’re going to have bugs, you’re going to give yourself some performance errors, or something like that, none of which happened. Then the other one is that you’re going to do it and no one is going to care. You’re going to spend all this time and just have crickets. So far, neither of those has happened. So it just feels good, and I feel a lot more calm than I was last week.
Mike [01:16]: Yeah. That was a huge change, I’ll say.
Rob [01:18]: Yeah, it really changed the focus of the app, and brings us on or above parity with a lot of really big competitors. So it’s definitely starting to have a ripple. And what we’re seeing is that launch day we got more trials than usual, but then it just kept going, and just every day after that there’s conversations in Facebook groups I’m being pulled into, and forums, and people are now asking questions like, “What really is the difference anymore between DRIP and all these big competitors?” Just that those discussions are being had with a lot of strong opinions has just up’ed the game. I mean we’re just being mentioned in places where there’re previously probably an open and shut case of, “I’m an infusion suffusion user, and that’s’ all I’m going to use.” or Entrepot or ActiveCampaign, or something like that. That just doesn’t seem to be the case anymore. And it’s noticeable as the trial count has – at least for now – and we only launched last week, in essence, but we already have reached a new normal for trial counts. We don’t know how long that will last, but so far it’s looking really good. How about you? What’s going on? You were at the Big Snow Tiny Conf last week.
Mike [02:16]: Yeah, it was a lot of fun. The unfortunate thing is that the New England area is not exactly cold right now, for whatever reason. We’re just having a warm winter. It did rain one of the first nights we were there, so the next day there was a lot of ice on the mountain, as opposed to snow. But it was still a lot of fun, and there were a lot of great conversations that were had, and people were grilling me early on. There was actually a betting campaign going on about what my upcoming product is, because people who were there were listening to the podcast, and they were like, “Oh, I think I know what it is!” So they went around the table. They wanted to start a pool. I don’t think any money ever actually exchanged hands, but some of the things that they came up with were rather interesting.
Rob [02:57]: That’s cool. That’s fun. To dive into that with folks, especially when people are already invested in the thought of it. So you pulled the trigger? You pick a name? You get something up?
Mike [03:07]: Yeah. so I guess I’ll finally pull the rabbit out of the hat, so to speak. I’ve got a minimal website up and running right now. The product is called Bluetick, and you can find it at bluetick.io. It’s animated follow-up software aimed at freelancers and small agencies who have high-touch sales pipelines. So if you think of current tools that you’re probably using – something like Boomerang or FollowUp.cc – it’s similar, but it goes a step further. In those types of tools, those will detect whether or not somebody replied to you, and if not it will throw something in your inbox and say, “Hey, you’ve got to go talk to this person.” Or, “You’ve got to follow up with them.” The Bluetick software that I’m working on will take that a step further, and will actually send the e-mail to them automatically so that you don’t have to.
And if there’s additional e-mails that need to be sent, it will do those as well. If there is a workflow in place that you need to put such that you’re walking them through a sales process, then it will be able to handle that stuff as well. So I’ve gotten a lot of great feedback from it so far, especially over at Big Snow Tiny Conf and then, as I said, I’ve got 12 people who have placed preorders for it. And right now I’ve got a team of developers who are tasked with building it based on the designs and stuff that I’ve put together, and they’ve been working on it. Things are going pretty well so far, and right now I’m focused more on all the marketing stuff, and I’m trying to stay completely out of all the tech stuff. People have been asking me for decisions and stuff on different things. Generally speaking, I’ve stayed out of the code.
Rob [04:32]: Got it. If someone’s a freelancer or an agency and they have a high-touch sales pipeline, they might want to check out bluetick.io, get on your list at least to see what you’re up to and hear the updates on the product. We set a deadline for this, didn’t we?
Mike [04:44]: The target deadline for having it in front of the people who’ve placed preorders from me is April 1. It’s a coincidence. Maybe I should have said May 30th or 31st or whatever it is, March. Whatever those months happen to be. Maybe I failed grade school, I’m not sure.
Rob [05:01]: It’s approximately 60 days from now.
Mike [05:04]: Yep.
Rob [05:05]: And are you on track?
Mike [05:06]: So far, I seem to be.
Rob [05:07]: The only other thing, I was just looking at my e-mail, and Sherry, my wife, is writing an e-book about founder retreats, and it is shaping up pretty cool. I just saw the final, or almost final, PDF version, and it’s going to be e-book PDF Kindle and ePUB. She got the layouts from a designer who cranked it out. It’s looking really nice. It’s looks to be about 28 or 30 pages, and it has a worksheet, and that kind of stuff. We’re going to be launching it more through zenfounder.com, if you’re not on that mailing list. If you’re interested in hearing more about founder retreats; whether you’ve taken one and you feel like you might need more guidance, or if thought about taking one and want, kind of, what at this point I’m thinking it’s the definitive guide to founder retreats. Mike, you wrote about it in your book. Sherry and I have talked about on the podcast. She wrote a little one or two page helper thing a while back, but this is where she just said I’m going to put down everything, all the knowledge that we have on this into a single resource. So if that sounds interesting, head over to zenfounder.com and get on that list, because we’ll be launching that in the next couple of weeks. What are we talking about today?
Mike [06:13]: Well, we got an e-mail from Dave and he asked us, “Hey guys. I’d love to hear an episode in regards to tactics for getting people to sign up for your highest plans. We have four plans but only 4% of people sign up for the highest two. Why is that? I’d love to know what the benchmark should be in terms of the percent of sign-ups and revenue your highest plans, on average, should be and tactics for increasing that percentage.”
Rob [06:33]: Dave is from ninjaoutreach.com. So we’re going to take the rest of the episode to explore Dave’s question. Really quick, I wanted to chime in on – he has a precursor question where he says, “We have four plans, but only 4% of people sign up for the highest two. Why is that?” Frankly, because a lot of your traffic these days is probably bloggers and small agencies. Which is, you have four plans. There’s blogger for $29, small agency for $49, large agency for $129 and enterprise for $249, and either you’re getting more bloggers and small agencies than large and enterprise, or it’s the fact that the price points are so different, right? You have a $49 plan. It’s your first from the bottom. Then your large agency plan is a big jump to 129. If people aren’t getting value out of your software yet, they’re probably not willing to dive in with both feet to pay 129 bucks. Most people want to try a lower priced plan to dip their feet in. As long as it has the same amount of functionality, why not sign up for the one user $29 a month plan, just to give it a shot so that, maybe, if accidentally I forget to cancel, or forget to stop after my trial, then I’ll only get billed 29 bucks – always knowing that if the person does start to get a lot of value out of it, they can quickly upgrade to the $49 or $129 plan. That would be my take on why only a small percentage sign up for the higher ones, because there’s no feature gating here. There’s no features that are not in the lower plans, and so there’s not much reason for them to sign up for the higher plans until they’ve seen value from your software.
Mike [08:02]: What Rob just said takes us into the first point of our outline for this episode. That is to highlight a default plan for the user. This, kind of, ties back into segmentation a little bit. You have to know who your audience is, and the bulk of the users who are coming in. For example, specifically on this page, the small agency plan is highlighted. So if you wanted to try and push people up into those larger tiers, you could highlight the large agency of the enterprise plan. I wouldn’t do the enterprise plan because it’s not typical to highlight your priciest plan, but highlighting the large agency plan would probably be a good bet there. The other thing that you’re doing here is that the names of the plans are essentially a self-categorization of the user. For example, enterprise users or enterprise companies are not going to sign up for a blogger plan or a small agency plan, because they can’t really justify that. Patrick McKenzie has some great stories about how he went in and tried to sign up his company for a personal plan that was only $9 a month, and his boss crossed it out and said, “Yeah, we’re signing up for the $500 a month plan,” and he said, “We only need the $9 a month plan,” he’s like, “Nope, we’re an enterprise. We pay for the top of the line.”
Rob [09:10]: Yeah, I think something else to think about is, where did you get these names from? We have blogger, small agency, large agency and enterprise. They’re great first cuts to allow people to self-select. But have you spoken to folks who’ve signed up for your small agency plan and asked them, “Are you actually a small agency? Do you identify as a small agency?” Try to forget how many of them are just random people. Maybe they run in a SaaS app or sell info products and they’re not an agency at all, but that’s the plan that they needed based on the number of users and contacts that you allow. So I would circle back and go for some qualitative data from your existing customers, because “large agency”, right off the bat, makes me think of a 50% company, and a 50% company probably needs more than four users, which is what this plan has, and she’d probably be paying more than 129.
That’s just my opinion. I’m not a small or large agencies, so I’m not necessarily an authority on this, but that’s what I’m saying is go to the people who are signing up and really figure out if these are the right names or if there’s another angle that you can take here with the naming. I think one other thing that I would throw out is we have four SaaS tiers on this pricing page. and I’m not sure if we really need tiers, or just doing a per user pricing, much like a CRM, would be a better approach. If you did $29 a month per user and each user gets whatever it is, 1500 or 2500 contacts, it would simplify your pricing. It will be an interesting test. I’m not saying it would absolutely be better, but since you’re not feature gating, and if someone is really a large agency and they do need 10 people in there, it would, kind of, be nice for them to come in and be able to pay that 290 bucks and get started with one user as they’re just getting their feet wet with it, and trialling it out, and then ramp up piece at a time instead of feeling like they have these big jumps between tiers. So here’s definitely arguments. It’s probably whole episode to talk about a per user or per subscriber cost, versus actually having tiers, and feature gating, and that kind of stuff. But that’s something that comes to mind here as maybe if these folks are used to paying per seat or per user, which I bet agencies are – because that’s how CRM is done, that’s how project management – then maybe that model could be closer to the other tools they’re using and therefore it might make a little more sense for them.
Mike [11:23]: The next item for how to influence decision-makers on your pricing page is to limit the number of sign up options. By that, what I really mean is if you’re trying to do too much on your page, it’s going to hurt the level of sign-ups that you get. If you start looking at most people’s pricing pages, you’ll see things like, “Oh, we have a monthly pricing, we have annual pricing, and then we also have three plans or four different plans that you’re offering,” and in some cases you’ll see things like a trial button, to sign up for a free trial versus a ‘buy now’ button. Once you start compounding those options, now you’ll say, “Okay, well, I have to decide, first of all, whether I’m going to do an annual or a monthly plan. Then I have to decide which of the plans I’m going to go for.” In addition to that, you also have to decide, “Do I want a free trial, or do I just want to pay for it now?” And tied it with that last piece is, are you going to ask them for a credit card upfront, or are you going to ask from them for a credit card down the road? That may be tied directly to whether or not it’s a free trial versus buy now. But again, you’re putting a lot of options in front of your prospective customer, and that serves almost as a road block to them even signing up, because they have to make all these decisions both before they get the software and start setting things up.
Rob [12:31]: Yeah. I’m not sure that I’ve seen this before, where there’s a 14 day free trial button for each tier, and then a ‘buy now’ button right below it. That feels to me like unnecessary decision-making, because now someone has to think, “Wow, do I want to do a trial or do I just want to buy it?” And I can’t imagine anyone’s going to want to buy it now without a trial, even if they know they want to use it eventually and they’re 100% sure, they still want to take advantage of the free trial. So that would be something I would definitely consider not having that ‘buy now’ button. It will remove another color from the screen, because that’s a green button, and it will simplify your pricing grid, in terms of there’s one call to action there and it will just be sign up for the free trial..
Mike [13:08]: The next item on the list is to deemphasize specific options. These are especially things you don’t necessarily want people to sign up for. For example, let’s say that you had a starter plan, where it was one user and it was very stripped down. You might have just a link there for that particular plan. If it’s a $9 a month plan, you might want to just get somebody started on your application and then up-sell them inside of it to a higher pricing plan. But then there’s also things like the enterprise plan, which if you have something that is going to be much more of a custom plan for that person, depending on the number of plans that you already have, you may not even want to have a column or a tier for that. You may just want to put down in the text some place that says, “Are you thinking that you’re an enterprise customer? You need something more than this? Just call us.” That way it doesn’t take up one of the spots on your page as a full blown pricing tier.
Rob [14:00]: And for that button on the enterprise tier, I’ve seen folks do ‘Call us now’. I think requested demo is an interesting test for that enterprise tier, because if they really are enterprise they probably want a demo before they can even think about anything else. They don’t typically want to start a free trial without seeing a demo of it. So what’s nice about requested demo is then, boom, you instantly ask for their contact information. You’re not making them contact you. You just pop up a form right there and ask for an e-mail, phone, perhaps how big their list its; some metric to where you can figure out how large of a customer they might be. Then the ball is in your court to follow up with them. And you could use fancy software like Bluetick.io or you could just put it in your CRM, or however you’re going to do it. Then, like I said, you are essentially in control at that point. So that’s another angle. Instead of having them taking action in terms of calling you, it’s nice to set it up where you have their contact information and can follow up as needed.
Mike [14:58]: A bit of a follow up to one that you mentioned a few minutes ago, Rob, which was removing either the free trial button or the ‘buy now’ button and just having the one to help limit the number of calls to action, and eliminate an additional color on the screen that’s fighting for attention. You can deemphasize other navigation options. So whether that’s up at the header, or in the footer, or even just removing pop-ups. I’ve seen pricing pages where they will still pop-up something that will try and get you to sign up for their newsletter. The one exception to them might be if you have something there that asks them if they have pricing questions, or have some sort of little widget there that allows you to interact with the person to help them make a decision. But that’s something I would definitely test. I wouldn’t just throw it out there and just hope that it’s going to work, or expect that it is doing its job. That’s something that you definitely want to test to make sure that it is moving people in the right direction.
Rob [15:49]: Yeah. I agree. I tend to strip away all the noise that I possibly can, all the buttons, all the colors and everything that you can, off of your pricing page and make it almost a little bit minimalist, or a little boring. Then the only colors that you need are on those buttons that you want folks to use, like the ‘start a free trial’ button. Those can be a nice, attractive – like an orange or a yellow – and they’ll really stand out. And you don’t have to make them flash, and have a marquee tag or something to stand out against all the other noise on your page.
Mike [16:21]: The next item on the list is using heat mapping software. On your pricing page, especially if you have enough traffic coming to the page where it makes sense to go in that direction, there’s a lot of different options out there. There’s Crazy Egg, ClickTale, Get Clicky. You really want to see where people are looking on your page, and find out if there’re other elements on the page that either people are clicking on because they’re distracting those people, or if there is copy that is drawing their attention and, kind of, influencing them on the page. Those are the types of things you want to know, and find out whether or not they’re additional things that you need to add on the page or remove from the page, because it’s either confusing the user or it is retracting from them moving in the direction that you want them to go.
Rob [17:06]: Yeah. Heat maps are really cool. I’ve learnt a lot from them. The two tools that I would use these days are Crazy Egg and Inspectlet. Those both give you a nice heat maps. You’d be surprised at how much you can learn from one of these. They also have scroll maps that shows you where people are scrolling and where they’re looking around. This is worth running on your homepage and pricing page at a minimum.
Mike [17:30]: The next item on the list is to identify feature differences. General advice and general wisdom basically says that you should be talking about the benefits of your products. But I think on the pricing page it is an exception to the rule, because on the pricing page people are much closer to making a decision. By that time, the expectation from you is that they have most of what they need to make a decision, and what they’re looking for is, what the pricing is, and which of the plans is right for them. They’re not trying to figure out, “Is this going to do something for my business? Is this the right tool for me?” What they’re really looking for is, “Which of these pricing plans do I fit into?” And, “I need help making that decision.” So at that point, comparing and contrasting the feature differences between your plans is much more important than it would be on your homepage, for example, or on a page where you’re talking about the benefits of using the software, or why you would use it. The pricing page, I would tend to err on the side of doing feature comparisons between the pricing tiers.
Rob [18:30]: Yeah. On a pricing page, you still want to be building that social proof with testimonial and these trust markers that we’ll talk about in a minute, but you don’t want to be still talking at a high level in terms of benefits. I think that’s something that people make that mistake of getting overly benefitted, and it feels like it’s vague, if you’re still talking about too many benefits — you can have a nice headline that’s a benefit, or the button can have the benefit on it, but if you have any other text on this page, people are already at decision-making process and they’re trying to figure out– it’s hard enough to make a decision. They’re trying to decide between your tiers. Make it really simple, really clear and very specific as to what they’re signing up for. Because without that, it’s going to sow the seed of doubt in their mind and the odds are they’re going to back out and not click that free trial button.
Mike [19:15]: One of the things that you just mentioned, Rob, was the trust symbols. With trust symbols, sometimes you can be pointing to third party rating systems, or maybe you’ll show like an SSL Certificate. Sometimes they have site seals that you can put on your website just to say, “Hey, this is secure.” I don’t know if I would put that on the pricing page itself. I might put it up on the sign up page, because I think on the pricing page it would probablydetract from the sign-up experience. But you do want to show – once they go through and they click the buy now button or the free trial – that you are securing their information. So that’s probably where I’d put the site seal information. On the pricing page, you might want to put some testimonials to talk about what other people are saying about your products, and what sorts of benefits those people have experienced.
When you’re doing that – I see this when people are using comments from Twitter, for example – and I’ve made this mistake myself. I actually still have a place where I have it on my list to do to change it, but If you have dates on those testimonials because they’re coming directly from Twitter, then somebody might look at that and say, “Oh, well that testimonial is a year old,” or two years old or five years old. You have to be a little bit careful about that, because you don’t want it to look outdated. You want it to look as if somebody just recently said that. I think that If you have those dates on there you do have to be a little careful about making sure that you either updating them with more recent things, or doing a live stream from Twitter is little bit of a risk because then you could have somebody goes on and just complains about it, and that could end up on your website inadvertently, and you don’t want that in your pricing page. You do want to make sure that you pay attention to whether or not those dates are displayed.
Rob [20:45]: I’m a fan of having testimonials, but not a big fan of having the big, bulky tweet boxes that come natively when you do a little plug in, or a Java Script thing that displays it, because there’s then just so many buttons appearing. You have like the person’s headshot, their name, their Twitter username, a follow-up button, a heart button, and a retweet. It just adds to the noise on the page. So when I tend to do testimonials, I like having a headshot if I can. I like having something in quotes, right? That’s the testimonial, and include the quotes around it. Then a name, and perhaps a URL that’s not underlined, that’s not blue, that doesn’t drag away the eye from the rest of the page. So if you are going to have tweets on it, I would opt to not use the big, bulky or fancy tweet boxes with all the options, because you want to remove that noise. It doesn’t necessarily add to the value of it to have all of that on the page. You can certainly use someone’s Twitter handle, and grab their headshot from their Twitter account and use it, but I would think twice before adding a lot of extra noise to the pricing page.
Mike [21:51]: The next thing on our list is to mitigate the risk for the user of signing up. This comes into play when you are looking at using a free trial button versus some sort of a buy now and saying there’s a satisfaction guarantee. If you use a free trial, there’s a limited time window during which they have to get in and they have to start setting things up. There’s this time pressure for them to do it. On the other side of it is if they’re buying it now, then they know that they’ve just paid for it and they have usually like a month or a year before they have to pay for it again. So hopefully, during any point up to that renewal time, they can go in there and start using the software. But you are forcing them to make a choice about whether or not they are going to get started using it right away, or they’re going to, kind of, delay that decision. So it does factor into that, and the trial length also factors into that as well, if you’re going to use free trials. So whether it’s 14 days, 21 days or 30 days, the trial length is something you’ll probably want to play around with a little bit to see whether or not there’s a difference in conversion. You want to be able to provide that value to them as quickly as you possibly can, but you also want to make sure that that’s as short as possible so that you can start getting them as a paying customer. So there’s a balancing act that you need to take into account.
Rob [23:04]: In terms of trial length I always try to go as short as possible so that you can run the most split tests. When I first required HitTail years ago, the trial was 60 days long, and that meant that I could only run six tests a year on the on-boarding e-mails, or on making changes. Then if you’re running marketing experiments, and different quality leads were coming in the phone, you didn’t know for two months. So you can make a lot of mistakes. Pretty quickly I had dropped that down to 30, and I wound up getting it down to 21. The reason I couldn’t go shorter than 21 is it was taking people about 21 days to get a lot of value out of HitTail at the time. Later on we rewrote the code and we were able to give value a lot quicker than that. But if you can do a seven day trial and people can get value out of your software in that timeframe then that’s what I would go with – even going as far as to charge upfront if you can. I feel like when you’re first starting out and you don’t have any type of brand or word of mouth, it’s a little hard to do that, not impossible – especially if you’re still learning about the app, and what people want, and what features you need, and the feedback is rally valuable – I’d probably still do free trials to get people in. But the time urgency of a free trial, there’s a benefit there. In terms of mitigating a risk for the users who are signing up, one of the big ones is to have that 100% money-back guarantee and to display it prominently on the pricing page, and to let people know that you will always refund the most recent monthly payment, you have a money-back guarantee within 30 days, just all that stuff.
There’s no reason not to do that. I know that some apps won’t refund payments, and to me it’s such short-term thinking. Yes, you’ll get some people who’ll screw around with it and they’ll get their $19 or their $39 back from you and it will feel unjust and the principle of it doesn’t feel right. It is absolutely not worth screwing all the other people who genuinely didn’t mean to do whatever. They forgot about something. They weren’t using it. There are lots of legitimate businesses that just have a reason to get the refund, and this world of ours is not that big. I know you think that you can, perhaps, not refund people and it won’t get around, but eventually it will. If you hit any type of size, word just gets around that you are not treating people fairly. So that’s always been my policy. It also helps keep chargebacks from happening, because charge-backs are expensive, and they’re a pain in the butt and you either have to fight them, and you spend the time to do that, or you get this extra charge. So if someone was not happy and you don’t give them a refund, the odds are they’re going to charge you back anyways and you might lose that as well, and it’s definitely going to waste time. So those are some thoughts around free trial, trial length and how to offer that money-back guarantee.
Mike [25:30]: The last item on our list is if you’re displaying answers to FAQ questions, make them relevant to the pricing tiers that you have. So rather than displaying a huge list of FAQs that are relevant to you products, make the FAQ questions that you’re going to display specifically relevant to the plans themselves. For example, maybe you have something in there about your cancellation policy, or whether somebody wants to upgrade or downgrade from a particular plan. Those are the types of things that are relevant. But things like “How to use your product” or “How to use a specific feature.” – those are things that should not appear on your pricing page.
Rob [26:07]: Right. Examples of questions that apply directly – either to the tiers, or just signing up for a trial – are something that I’m pulling here from the HitTail and the DRIP pricing pages. Questions like, “How does the trial work? What if I go over my monthly limit? Do I have to sign a long term contract? What happens when I start a free trial? What’s the set up process like? Can I change my plan?” Right? Those are things that people are thinking about as they’re looking at your pricing grid. So they may not answer specific questions about a specific pricing tier, but it is what’s going through the person’s head as they’re deciding whether or not to sign up, and they’re thinking, “What are the risks? What are the negatives of doing this?”
Mike [26:42]: And if you’re looking for additional resources on conversion rate optimization, we’ll include a link over to quicksprout.com, where they have the definitive guide to conversion optimization. There are a few things from this episode that were taking from that, but there’s a lot of things on there that are generally applicable to your website itself, or to learning pages. So there’s a different instances where some of the things that they have in there would be applicable.
Rob [27:04]: We outlined and recorded this entire episode based on a listener question from Dave at Ninja Outreach. If you have question for us, call our voicemail number at 8-8-8-8-0-1-9-6-9-0, or email us at questions@startupsfortherestofus.com. Our theme music is an excerpt from ‘We’re Out of Control’ by MoOt, used under creative commons. Subscribe to us on iTunes by searching for startups in business, startupsfortherestofus.com for a full transcript of each episode. Thanks for listening and we’ll see you next time.
Episode 274 | How to Mentally & Technically Prepare For Your Launch (With Guest Derrick Reimer)
Show Notes
In this episode of Startups For The Rest Of Us, Rob and guest Derrick Reimer of Drip, talk about how to mentally and technically prepare for your launch. They give you first hand advice from things they learned and experienced when launching a new feature to their product.
Items mentioned in this episode:
Transcript
Rob [00]: In this episode of Startups For The Rest Of Us, Drip takes over the podcast. My co-founder Derrick Reimer and I talk about how to mentally and technically prepare for your launch. This is Startups For The Rest Of Us, Episode 274.
Rob [21]: Welcome to Startups For The Rest Of Us, the podcast that helps developers, designers, and entrepreneurs be awesome at launching software products, whether you’ve built your first product, or you’re just thinking about it. I’m Rob.
Derrick [30]: And I’m Derrick.
Rob [31]: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. What’s the word this week, Derrick?
Derrick [36]: The word is “Workflows.”
Rob [37]: Indeed, it is.
Derrick [40]: We just launched probably our biggest paradigm-shifting feature in Drip since we launched our automation engine about a-year-and-a-half ago.
Rob [48]: It was quite a week, this week.
Derrick [50]: Indeed.
Rob [51]: It always is, and that’s what we want to talk about today. We were in a discussion the other day, and I realized it was probably worthwhile having on the podcast. Mike is out this week at Big Snow Tiny Conf in Vermont, and since we did this launch this week and there was so much that I learn every time we do one of these – both from just a planning perspective, like, the actual tasks we have to get done in terms of getting the feature built, getting the marketing out; but then there’s also that whole mental side of it. And I think I experienced it. I think part of it is being lack of sleep, but part of it is just trying to get stuff out on a deadline, that is pretty interesting to talk about and, I think, it help folks who are interested in preparing better for their next launch, whether it’s a feature launch like we just did, or whether it’s an actual product launch.
Derrick [01:33]: Absolutely. It seems like we go through these constantly, but it somehow never seems to get easier.
Rob [01:38]: I know. I know. I wonder. Part of that might be that you just get more and more ambitious with each one.
I think about the very first launch that I did. I’m trying to think of what it was. It was probably launching a new version of DotNetInvoice, and it was release the code and email my customers, and that was the launch and that was it. So it was pretty easy, because I had to draft one email and check something into source control and put a zip file on a server.
But this launch that we did this week with Workflows – and if folks didn’t hear about it, it’s, in essence, a visual way to build a marketing funnel. So it’s centered around email, but there’s all types of stuff you can do in terms of tracking someone clicking a link, or an action they did outside of just doing stuff in email, so it’s a visual flow. I’ll put a screenshot of it in the show notes for this. Or, frankly, you can go to getdrip.com/workflows and check out the whole deal. But launching something this large is more ambitious than just an update or some bug fixes. And so we didn’t just push a feature out, we did a big marketing push to people both in our list and not. We had some loose partnerships. We had some onboarding we had to redo. A bunch of documentation had to be updated and all that stuff.
Derrick [02:49]: Right. And on the technical side, there were a lot of opportunities to break things when building this as well, and the stakes are higher because with this new feature, we basically had to rewire the app to push everybody to center their whole account around their Workflows. So it’s – yeah, definitely the stakes are higher with this feature.
Rob [03:07]: Let’s start by running through the tasks that need to get done to launch a feature or a product. Maybe you won’t have all of these in your particular case, but this is what we saw, and this is a complete representation of the stuff that we’re working on to get Workflows out this week. I think the first one is just finishing the feature itself, getting the code out there in a way that the feature or the product is done. And, frankly, you were almost done with it a couple weeks prior to the actual launch.
Derrick [03:39]: Right. A couple weeks prior, we started to get some early-access users looking at it, and we didn’t encounter a whole lot of technical problems after they started using it. There are a few things here and there, a few recommendations on things we can improve, but it was pretty technically sound. At that point, we started looking at the other tasks that were needed to actually get this launch started.
Rob [04:01]: Right and the plan for this one was to do a little bit of a buildup. Since it was such a big feature we were getting out, we didn’t just want to launch it and send an email. We actually wanted to give a teaser a couple weeks in advance, but the thing is once you send a teaser email like that, you’ve basically set a ticking clock, right? You’ve started a timer. And assuming you want to hit the deadline that you’ve committed to – which, for us, the teaser said, “It’s coming in two weeks” – we know people will give you a day or two, but if you go a month after that, people are going to notice. So we really wanted to mentally focus on hitting that. If you’re going to do that, then you’d better know everything that needs to get done between that point and the day that you’re going to launch.
And I felt like we did a so-so job of that. I felt like, technically, we were dialed in, but there were so many other things that we discovered after that like, “Oh, all of our knowledge base docs. We need a ton of knowledge base docs for this.” We had a lot more marketing collateral and email copy and blog post copy and filtering of lists than I thought we were going to have. Then there were also a few things on the technical side that we had to expand, and we discovered that, I think, the day we sent that two-week email. You and I went into a conference room, and you said, “We need to rework some stuff.”
Derrick [05:12]: The big thing that jumped out as soon as we started the clock ticking was our entire user onboarding – basically, we call it our “guided setup”, which is a few screens that ask you some questions when you first sign up for a Drip account and basically helps us to auto-generate some things in your account, like a campaign and an automation rule and things like that. We realized that, basically, our whole guided setup was centered around our basic automation rules, and now we’re trying to get people to shift into centering their whole account around Workflows. And when we originally built guided setup, I think it was at least a month long of planning and iteration and building out how exactly should this wizard work. So, yeah, it was a little frightening to realize that late in the game that we had missed something so large.
Rob [05:58]: Right. So, again, the feature itself was pretty much feature-complete, code-complete, and it was even in beta, so it was pretty heavily tested. But the realization of, “Oh, yeah. Our onboarding doesn’t push anyone into Workflows. It’s going to take them through this older style of stuff,” we had to sit there in that conference room and say, “How can we best do this in a way that works for our new trials, but that doesn’t take more than two weeks, in essence, because we literally have a ticking time bomb?” And that’s not something we do. We don’t do deadlines here at Drip. We just haven’t ever set a hard deadline like that. We push, and we try to get stuff out on a time schedule, but we don’t kill ourselves. We have the luxury of doing that, since we don’t have the investor timelines and we don’t have a burn rate. And so that was, I think, kind of a new experience for both of us.
Derrick [06:41]: Totally. And there were some other features that I really wanted to add in if I had time in the two weeks leading up, and when you’re looking at it a month out, you feel like you have a lot more time than you actually do. When that clock is ticking and you start looking at, “Well, this is how many business days we have left until that deadline, and if I do sub out some of this work to someone else on the team, we’ve got to review everything, make sure everything is airtight before deploying it.” So you realize how quickly those deadlines come up. I definitely had to cut out some features that I really wanted to add in the interest of getting our onboarding done.
Rob [07:16]: Right, and so those will go in post-launch, and I think we prioritized those yesterday.
So in terms of actual tasks, we’ve talked about a couple so far. I have a total of eight here listed. The first was basically finishing the feature or the product itself. The second one was – for us, it was realizing that, “Oh, there’s this extraneous thing that’s impacted.” It was our onboarding that was impacted. So I think, as a listener to this, if you’re launching a brand new product, you don’t have to worry about this, but if you’re launching a major, new feature, try to sit down earlier than we did and think about, “How does this feature impact other features in the app,” such as your onboarding, or such as other flows that are already existing. Because I think that while technically everything would’ve worked and nothing would’ve crashed, it would’ve been a poor user experience had we not circled back and done that.
The third thing that I thought was interesting was we had maybe 5 to 10 alpha users, and then we had close to – I think it was between 20 and 22 beta users who were really digging in and building production Workflows. I was working one-on-one with most of them, answering questions via email. If they ran into any issues, we were correcting them or clarifying them. A lot of them were just questions or misunderstandings rather than any type of technical bug or issue, but the amount of feedback that generated and the number of tweaks we made based on that was not inconsequential. We added a couple features based on some really good advice from some – these are very knowledgeable, influencer beta users who use other products that compete with us. We wound up adding a couple new features within the last couple weeks, as well as making some tweaks.
How did you feel about that and how that process went?
Derrick [08:49]: I felt really good about that. I always enjoy getting features in front of customers early on, because it’s like we talk about, with launching brand new products. You never want to go off in your basement and build for months, without getting it in front of potential customers or people who are really knowledgeable about the problem space you’re trying to attack. So I felt really good just showing it to people and hearing this feature that I thought made perfect sense, as soon as someone else looks at it, they’re a little bit confused by it. Then as soon as we iterate on it and work on it, then it becomes clear that, “Oh, yeah, it totally makes sense what they’re saying.” So I like to think of any big feature like this as almost a brand new product that we have to do adequate customer development on and getting it in front of people.
Rob [09:34]:And to be honest, I found that having knowledgeable beta users using it in production flows and giving us feedback made me rest much easier when we did the launch, because I knew that it had already been battle tested pretty well and that a lot of questions had been answered, and those early rough spots in an early product were ironed out by that point, right, because we had folks who were using it and offering suggestions in a controlled environment where we didn’t have 500 people or 1,000 people using it. We just had ten or 20. So if you have any time where you can carve that out and give yourself even a week or two to hone the product based on user feedback, it will make you sleep better the night before launch.
Derrick [10:15]: Absolutely. And just back to the point of part of the process of finishing the feature, I feel like this is included in that, where immediately I felt better once I was able to take this feature that I’d been working on for a few months and actually deploy it into production behind some feature flags. So just knowing that this code is actually running on our live servers, nothing’s falling apart, and now we can tick a box in our admin screen to open it up to people and start getting people using it, that’s just a major load off my mind.
Rob [10:45]: I agree. That’s another good point, and that’s something that we’ve done a lot over the past couple years is we try not to have these big branches, these two-, three-, four-month-long branches/features that are not merged into the core codebase. Because one of the worst things that can happen on launch day is not only are you worrying about all those extraneous tasks and the marketing and the docs and all this stuff, but you’re also trying to merge in code, and you’re breaking other things. So that’s something that you’ve been really good at, is along the way, you were trying to get as much code into production months before we actually launched this thing.
Something else that I was thinking of that we didn’t have to do here, but may happen if you have a really big launch list, or if you think that this new feature is going to be hitting your servers hard is some folks have to increase their capacity. They either have to staff up with support, or they have to increase server capacity, spin up new VMs and stuff like that. We didn’t have to, because we don’t see this as being a big load on our servers.
Derrick [11:43]: Look, fortunately for us, this one’s pretty light on the servers.
Rob [11:48]: The next task that you’ll want to think about – and this is our fifth one we’re talking about – is essentially getting your documentation up to speed. We call them “KB docs.” They’re knowledge base docs. You can check all our stuff out. It’s at kb.getdrip.com, see how we structure it; but for a feature like Workflows, that’s almost an app unto itself, you need docs that show people: a) how to get started; they need a quick start guide; b) they need a more encyclopedic list of what do all the steps do in these categories and what are really the ways to use this. And then they probably need some case studies or use cases. They probably need an FAQ. They might need a migration guide of, “This is the way we used to do it with one-off automation rules, and we’re still going to keep those around for certain purposes, but Workflows are now the main focus. And if you can, and it makes sense, then move yourself into Workflows from rules.”
So all that to say that’s not just one KB doc. That’s not just cranking up WordPress and hammering something out. And this really requires some planning in advance, and luckily we have the help, and we were able to get Anna to write all these KB docs. But I can’t imagine if we were still a two-person team or a three-person team, this would have been an enormous amount of effort for us to do, in addition to the marketing and the technical side.
Derrick [13:01]: Oh, man, yeah. It’s really easy to think that the feature itself is the hardest work and to think, “Oh, yeah, the documentation – that stuff, we’ll maybe work on it the day before.” But watching Anna, our customer success person, flesh out all these docs and start rerecording help videos and rerecording her demo videos that she sends to folks who want to watch a video demo, it’s been a monumental effort, for sure. Just a few days before launch, we were all sitting in the office, and you and Anna were both editing videos, and I watched you guys sit there for hours. I realized that the editing process is really time-consuming. So things like that, it’s important to keep in mind that everything takes longer than expected, just like feature development.
Rob [13:42]: Exactly. Exactly.
Last couple things. One is basically just your marketing plan and your marketing collateral. For us, there was a lot of email copy and thought put into how that was going to be sent because we have a lot of segmentation, right? We don’t just want to send our customers, our marketing lists, all the same stuff. If people are in a trial, they probably want to hear something different about the feature. If they’re a customer, they want to hear something different. They want to see KB docs. If they’re just on a marketing list, then they probably don’t want to see KB docs. They really want to hear, “Why is this important to me? Should I sign up for Drip?” because they’re not even a customer yet. So thought went into how the emails were structured, and then announcement blog posts, and then we had the whole Features page that we added. You brought it up two weeks in advance, and then it never made a list, and so then it was like two days before, and we were also scrambling to get that out.
But there’s a lot to be thought about here. It, again, is not just so feature-centric. Especially if you’re going to do a launch that requires multiple phases of marketing, where you’re not just sending a single email, but you’re doing a two-week-before and then a day-before. Then that day before, realize that if you create any type of stir or conversation, you’re going to be on Twitter a lot of the day. Or you’re going to be answering emails. Or you’re going to be helping answer questions on forums, or in Facebook groups, where people are talking about us. So a lot of time can be pulled into that, so it’s better to be ahead on pretty much everything and not waiting last minute trying to do that, and still finalizing the next day’s copy.
Derrick [15:08]: Absolutely. A lot of this stuff we talk about, like the demo videos, the KB articles, the blog posts and feature pages that explain what this is, all of that, you could probably skip some of that, but what you’re doing is potentially creating a much larger volume of support and questions afterward. So part of this is doing the work up front to mitigate the amount of questions and support emails you’re going to receive, and also just it makes customers happier if they can figure things out on their own and things are intuitive. And when they do have a question, the answers are right there at their fingertips.
Rob [15:40]: Right. Another thing that we did pretty well with is you have to prioritize. For a while, I kept saying, “If we can do a screencast – if we have time, then we will do it,” but that is below the priority of just getting the features page up and just getting the launch copy written. As it turned out, I was able on the last day, to get a screencast recorded and edited, and we got it into production after getting some feedback from you guys. But if we hadn’t had time, if something had gone sideways, we just would’ve launched without it, and that’s okay. You don’t need all of this stuff. This is trying to approach the perfect launch. We really were thinking, “What is the ideal launch that we can do that will give us maximum impact, maximum conversation, maximum number of trials coming in, the least amount of support?” because we answer questions up front. That’s what you’re trying to think through, but you may not be able to do everything that you dream up, and there may be some things that you do have to leave on the table, in essence.
The last task that I want to talk about is interesting. It’s another marketing piece, but I found myself spending a lot of time working with our early users, our early-access folks. Some of them are influencers, and some of them are just people who are power users of Drip, and so we wanted to get them into an alpha just to play around with it. We knew it was still buggy. This is, like, November, December. Then we pushed it into beta in, I think, early January. And that’s when we started doing a lot of production work, production flows for ourselves, and other people started building it. The nice part about that is I was in such steady communication with them that by the time we launched, these people knew how to use it pretty well, and they were able to instantly throw stuff into production if they didn’t have it already. And since they’d been part of the process, they began tweeting about it and talking about, and it definitely drove conversation and it made people feel like, “Wow. These Workflows are everywhere.”
That’s approach you’re trying to go for. So we had [Brenan Dunn?] record a screencast yesterday all about a flow he built and threw into production. We had Dan Norris posting in his – he has a seven-day startup, private Facebook group, and he was posting in there about it. It’s because these guys we’re in early. They’ve been longtime Drip customers and they were using Workflows for a month before everyone else, and so they had the familiarity and the confidence in it, to then on launch day be able to do that kind of stuff for us.
Derrick [17:46]: Absolutely. It didn’t seem like it was a stretch for any of them to honestly say, “This is a super awesome feature. You should go check it out, and here’s what I’ve done with it so far.” It wasn’t forced. It wasn’t like they were pulling a favor for us, necessarily. They were really genuinely excited about it, which is, I feel like, the best way to do it.
Rob [18:05]: So the interesting part with that was it was very time-consuming, period. I did a lot of one-on-one emailing. It was totally worth it in the end, but realize that this is another task that you have to do if you’re going to go down this road. And in early products that I did and launches that I’ve done, I haven’t done this part because I didn’t have the team doing all the other stuff that enabled me to have the time to do this. Because if you are writing the code, and you’re doing the marketing collateral, and you’re doing the docs, and you’re going to handle support this is a nice-to-have, and it can help you, but it’s not in the top of the list – right – in terms of getting features out. But it can be powerful if you have folks who are on your side on launch day.
All right. So let’s dive into the mental side of things, because in addition to just getting the feature out and getting all the marketing and the docs, there’s this levels of stress that hit you at different points. And there’s mental games when you and I are up until midnight, and then we wake up at 5 in the morning to launch the product. There’s a certain amount of struggle that you’re going through to just think clearly and make good decisions and to sleep well when you can and get it done. So I think the way that I was thinking about it is a couple weeks before the feature launched, before we set the initial, “Hey, this feature’s going to be out in two weeks,” we all had a conversation at lunch. My memory of that was that the sentiment was very positive. Do you recall that? I don’t remember feeling any stress during that meeting.
Derrick [19:25]: Yeah. No, I felt like we had given ourselves plenty of time to build the feature, to test it, to get people using it. We already had our beta users banging on it and making sure that there were no bugs, so I felt really calm at that point.
Rob [19:36]: Then we sent the two-week email, that started the clock ticking, and then essentially that day or the next day, we realized, “Oh, we have to rework our whole onboarding.” What did that do to your psyche?
Derrick [19:49]: That definitely added an element of stress. I don’t know why setting a deadline in public like that somehow opens up areas of your brain to think of things like onboarding, but as soon as we did that, I can remember the moment and starting to think of, “All right. What do we really have to do in the next two weeks, because things have gotten real here?” And that’s when all these little things like – or, big things, like onboarding, started coming up. At that point it wasn’t – I don’t feel like it was toxic stress, but it was definitely stress.
Rob [20:18]: That’s a good point you bring up about setting a deadline in public really puts your feet to the fire. And I agree. I also started really gathering the list of deliverables at that point, and we really should do that before we set the deadline, but you just don’t. It’s just the nature of how we’re rolling. If you’re moving fast and doing things, I think you’re just – maybe it’s, like you said, your mindset shifts once you’ve committed to something.
Rob [20:43]: And I think that’s a good thing. I think that’s a lesson for listeners to take away, is if you find that you’re just pushing it off and pushing it off, maybe just set a deadline in public even if it’s just on Twitter, or even if it’s just in a blog post. It may not be to 10,000 people like we did but maybe it can be to 50 or 100. And if you feel that pressure, it can be something that forces you to make some tough calls towards the end. I could totally have seen that if we hadn’t set that two-week deadline, that it may have taken us a month to get it out. We may not be launched, because there were things that were coming up that we were like, “Oh, yeah. There’s this other feature someone just asked for. Should we build it before launch or not?” And if we could’ve pushed off launch, we very well may have decided to.
Okay. So that takes us up almost to the launch. I think the week before, we were doing fine. We were hammering stuff out, and then really the day or two before, we all came into the office. We typically come into the office a couple days a week and we really packed those days before launch with office time. We essentially launched on a Wednesday; and for me, personally, I felt like Monday was intense, but not stressful. We were all very focused. In fact, we normally have a lot of conversation here in the office, but I felt like we all had headphones on with some type of deep-focus playlist. We knew what we had in front of us. Did you feel the same way?
Derrick [22:00]: I did, yeah. At that point, it was all hands on the feature. We all had our own individual tasks we were working on for it. There were a few points where we wanted to be in the same room, because sometimes you just get those spontaneous – someone has a thought, someone brings it up. Another person hears it and contributes, and magic happens. So I think we had a few of those moments, and some really good things came out of it, but for the most part we were pretty heads-down.
Rob [22:24]: And I think that, as a listener to this, the theme for those 48 hours before launch is “focus.” That’s what. You have to focus in. We sat around the whiteboard, and we figured out what were all the – we threw them out. What are all the tasks that need to get done? And then each of us took their tasks. I had my own Trello board, and it basically had the list of tasks, because I was writing the email copy and segmenting the lists and running lists through some processors and trying to get the screencast done and talking with our launch partners. You were finishing up features and onboarding. Anna was doing KB. Ian was doing other stuff. So I think the fact that we did that once, got everything out on the table that we knew about that had to get done, and then all went into our little cocoons of deep-focus sound. I think that’s a way better approach, way less distracting and way more productive than always having something new, then not thinking of everything –
Derrick [23:11]: Right, absolutely.
Rob [23:12]: – and having the interruptions.
Cool. So the night before launch, I was stressed.
Derrick [23:18]: I was pretty stressed as well. We had just wrapped up the onboarding stuff, so of course it took a little longer than usual. We were so heads-down on our tasks that we had – we had tested it. I had tested it locally, and Ian had tested it as well, but we basically started doing our final run-through. We had it deployed in production, so that only we could see it, and we started –
Rob [23:41]: Right. This is just onboarding, not the feature itself.
Derrick [23:44]: Right, just the –
Rob [23:44]: Just the onboarding code, yeah.
Derrick [23:45]: – onboarding. The main feature itself was solid, but the onboarding, we were doing final run-throughs, looking basically from a very high level, end-to-end, what is the user experience of signing up for a trial, going through onboarding, the guided setup and then looking at your first Workflow. There were definitely some things that we all caught that night that were just extra polish things, but that path is so critical. So to be working on those things at the eleventh hour, essentially, was pretty stressful.
Rob [24:17]: It was literally the eleventh hour. It was 11 p.m. and we were on slack. I’m starting to nod off in my chair, because I’m not as young as I used to be, and I’d been getting up early to do stuff. I was like, “Oh, man. I just went through it, and this part – what are we going to do about this?” I know that at 11 p.m., that’s not what you want to be doing the night before launch.
But it was cool. We came up with, I think, some really good tweaks and we added some yellow highlighting to something just to call it out, because I felt like people wouldn’t see it. And we came up with good solutions that you were basically able to implement in under an hour.
Derrick [24:47]: I was pleasantly surprised that the problems that we did discover – or, not necessarily problems, but just things that could’ve used extra polish – that we were able to come up with a quick solution and deploy it in a way that it didn’t feel like making some last-minute change that might break a bunch of stuff. So it worked out pretty well. It could’ve been worse, but it turned out to be pretty smooth.
Rob [25:09]: And I think the lesson here for a listener is we were down to the wire, but it was down to the wire with onboarding. Realize that we could’ve shipped with what we had. We were not tweaking the production feature at this point. That had been feature-complete, code-complete for a long time with beta testers and all that, because that would be really scary. I would’ve pushed the launch off if we were still tweaking code the night before, because there’s no chance that we could launch to that many people with any type of question that we were going to have some buggy interface. This really was small stuff. So there was a certain level of stress, but it was a lot less than if we suddenly discovered some major flaw in the feature itself. In fact, we would’ve just pushed it off at that point for risk’s sake.
So there’s interesting levels of stress that go along with a launch like this. One can be a technical one of, “Oh, man. Is the feature going to work? We haven’t tested it well enough.” Try not to be in that boat. We were not in that boat, I felt like. There’s other stress, though. It’s all this work and all this time. Because it was five, six months of development, and then the last several weeks, it was the whole team, all hands-on, doing all this stuff. “Is this going to be worth it? Or is no one going to care?” It always goes through your mind. Or, “Are people going to be haters?” Are people going to be critical of it? Is something going to happen? Are we missing it here? So were we going to get criticism, or negative feedback, or is no one going to care? That’s another stress, I think, doing this, because you’re really putting yourself out there.
Derrick [26:25]: Totally. Are people going to sign up? We’ve just completely transformed the whole guided setup, the whole onboarding process. Are people going to be completely confused and not know how to use the app anymore in such a large shift like this?
Rob [26:38]: So we woke up on Wednesday morning around 5:00, 5:30, and we deployed everything. I remember you said, “I’m pushing the button,” and I logged in, and there were such minimal changes, because all the code pretty much was already in production. And all you did was add Workflows to the marketing site top nav and changed where the automations button. It was some very minimal stuff. So I remember feeling calm in the sense that the complex code that was in production had been in production and being hammered on for weeks, and the only changes were more aesthetic, I guess.
Derrick [27:11]: Right, just basically opening it up – removing the feature flags and opening it up for everybody.
Rob [27:15]: Yeah, which was nice. I’m always surprised on launch days. I think it’s a good thing, but launch days themselves tend to be anticlimactic. Did you feel that way as well?
Derrick [27:26]: Yeah, I did. You see these startup launches are things that create a big splash and a big viral wave of chatter and people talking about it. And we definitely had a lot of chatter on Twitter and things, but, by and large, it wasn’t like we had a thousand new users sign up, or servers going down, or – basically, it always end up being calmer than I expect.
Rob [27:48]: And I think that’s a good thing, because I think there certainly were conversations going on online, and we were responding to that kind of stuff; people talking about it on Twitter, and that’s a good amount of action going on. What you don’t want is the action of bugs being found, or people running into problems or getting confused. If it’s calm, probably consider yourself lucky as long as people are talking about it and/or signing up for trials.
So the day of, I didn’t feel too stressed about it. You as well?
Derrick [28:15]: Yeah. I felt really calm the day of. I did have trouble – for some reason, I had trouble focusing on the day of, I think because you’re just on edge, waiting for the other shoe to drop – like, “What’s going to go wrong?” I was looking at my list of tasks and things that I wanted to get in before launch, but didn’t quite have time and thinking, “Should I start working on one of these right now, or should I be trying to anticipate what might go wrong and get out ahead of the problem?”
Rob [28:40]: I totally agree.
Derrick [28:41]: I think I had that going on just looping in my head, and I think it affected my ability to focus that day.
Rob [28:47]: I think that’s something good to take away – is consider your launch day a non-working day. You’re going to sit in front of your computer all day, and you should, and you should interact with people, but you will likely get zero work done. Because I was in the same boat as you. I sat there and stared at my email queue. I really didn’t have anything to do after the emails went out aside from handle some email and some important conversations, but that was very minimal. Yet, I feel like I accomplished nothing that day, because I had that same track playing for me of, “What’s going on?” “Where are we?” “What’s going to happen?” It’s kind of like the stress that built up over the previous two weeks – it doesn’t just go away when you launch. It doesn’t dissipate. It hangs around, and I think that launch day is the day where you’re able to blow off that steam and release it. Because for me, the day after launch was actually when I came back and I felt really good. I wasn’t depleted anymore like I was on launch day.
Derrick [29:34]: Right. And we were a little tired, too. I know I took a nap on launch day when I found a lull in the afternoon.
Rob [29:40]: Well, yeah, after five hours of sleep, it’s probably a good idea to get your wits about you.
Hopefully, this gives you some thoughts and ideas and a checklist of how to mentally and technically prepare for your launch, whether that’s a feature or an entire product. Again, you may not run into all of these things, depending on the size and complexity of your launch, but these are definitely things to think about and get out ahead of before you do so.
So thanks for joining me today, Derrick.
Derrick [30:05]: Thanks for having me. It was a blast.
Rob [30:07]: And if folks want to keep up with you online, where would they do that?
Derrick [30:10]: Probably on Twitter @Derrickreimer.
Rob [30:12]: Sounds good.
If you have a question for us, call our voicemail number at 888.801.9690, or email us at questions@startupsfortherestofus.com. Our theme music is an excerpt from We’re Outta Control by MoOt, used under Creative Commons. Subscribe to us on iTunes by searching for “startups” and visit startupsfortherestofus.com for a full transcript of each episode.
Thanks for listening, and we’ll see you next time.