Episode 429 | Building a Launch List of 5,900 and Grinding Out Customer Development

Show Notes

In this episode of Startups For The Rest Of Us, Rob talks with Derrick Reimer about his new product Level. They go through the development timeline as Derrick gives insights on the early access phase, alpha testing, taking pre-orders, and going live with the MVP.

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Transcript

Rob: In this episode of Startups for the Rest of Us, Derrick Reimer and I talk about how we built a launch list of 5900 people and how he’s been grinding out customer development on his new effort Level. This is Startups for the Rest of Us episode 429.

Welcome to Startups for the Rest of Us, the podcast that helps developers, designers and entrepreneurs be awesome at building, launching, and growing software products. Whether you’ve built your first product, or you’re just thinking about it. I’m Rob.

Derrick: And I’m Derrick.

Rob: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. So where this week, Derrick?

Derrick: Just in the startup trenches doing some customer onboarding calls.

Rob: How many calls have you done this week?

Derrick: So far, I’ve done seven. I have 11 or 12 booked right now.

Rob: Very nice.

Derrick: I reached a milestone this week. It feels good to finally be in the realm of getting the product into the hands of potential customers and having those awkward conversations about, “When do you want to start paying for this thing?” but it feels good to be in this realm.

Rob: Yeah, it’s cool. You’ve been working on Level now for 9 or 10 months. It’s a long road to get to this place even for those like yourself who’ve done it a few times before.

Derrick: Yeah, it’s kind of unbelievable when I look back at the timeline. Depending on how you look at it, some would say that’s a really short amount of time to just go from nothing to a product that is potentially viable, but on the same token I’m ever impatient and feel like, “Man, it’s been an eternity.”

Rob: Right, and you’ve been able to work full time on it which is a luxury a lot of people don’t have. I can imagine doing this nights and weekends trying get here. I know you’ve been there, so you remember how it was.

Derrick: Totally.

Rob: We’re going to dive in today to your story. We’re actually going to catch folks up because last time you were on the show was in July, it was episode 399. We talked about how you were validating the idea of Level and how you started having people reserve their handles to build your pre launch list. Today, we’re going to continue that story. We’re going to talk about where you’ve been since then, tell the story of the major milestones you’ve hit through the rest of 2018, and pull out the learnings from those. Folks listening can see how an experienced founder like yourself has taken on this challenge of building essentially a competitor to Slack, which is an app that has a lot of momentum, and trying to thread a usability needle and have a different use case that works better for your development teams.

But before we dive in, I want to talk about an AppSumo contest that’s happening, where AppSumo is going to pay for an all-expense paid trip to both MicroConf Starter Edition and Growth in late March. We’ll link that up in the show notes, but they’ve graciously sponsored this podcast and are going to be giving somebody a trip to both of those. You could be a lucky winner Derrick.

Derrick: Yeah, I know, because it’s open to anyone even if people have purchased a ticket, right?

Rob: Exactly. We’ll refund your ticket if you win. I don’t think it’s open to me, but I’m tempted to apply.

Derrick: I was going to say I’d definitely jump on that. If there was a call to action in that email, I’m sure I clicked it. I’m not sure how that would look if I won it, but here’s to hoping.

Rob: I know. I just know that I am totally not involved in the selection process. I have no idea what’s going on. That giveaway ends on February 11th, which is another week or two after this goes live. Check it out if you haven’t.

You were here in July. You and I were talking before the show, kind of laying out some milestones that happened since then. I know you were heads down, you’re in pretty hardcore design mode of trying to figure out what are the screens going to look like, how am I going to architect the inbox, how do you compete with Slack in a way that is less invasive, less interruptive. I mean, that’s the promise of Level. For folks who want to a good explanation of it, go to level.app and it’s your headline there, ‘Team communication optimized for deep work.’

In September, you were telling me you came to a fork in the road in terms of this. You’re writing some code I believe, but you were trying to decide the hardest part of this app to design really is probably the inbox. From a usability perspective, you just have to get it right. Talk to us about where you were in September.

Derrick: Up until that point, it’s funny now looking back like why did it take me so long to get to where I am today? I think a big part of that was, I spent a few months at the frontend just focusing mostly on getting familiar, comfortable with the Tech Stack, this is an application that has a lot of real time stuff. It will eventually need offline support, web sockets, just a very different type of application from the ones I’ve built before.

I spent a lot of time getting familiar with Tech Stack, and also I had a general vision in my head of how the product should work, like just kind of picture how it would feel. It’s interesting how once you get from the phase of, I have the vision for this thing, and how it should function, and how it should not interrupt people like Slack does, to actually getting down to the implementation.

There’s a big gap there. In theory I know how it should work, but it’s actually a really hard problem to solve to strike just the right balance. I think we were sitting on your rooftop, September, I was sipping some scotch and I was like, “Rob, what am I going to do?” What should I do? Should I spend time doing another round of calls with potential customers, try to put together some wireframes and some mockups, show it to them, cast a vision for how it’s going to work, and potentially get responses like, “Yeah, looks cool”? Or do I take the route of just spending some time writing some code, and implementing what I feel is my best guess at how it should function according to my own experience, and what I’ve heard from others?

To me, at the time it felt risky because I know that that big trap that a lot of people fall into is going to the basement, code for months, emerge, and potentially be missing the mark. I’ve been very careful and almost a little bit paranoid not to fall into that trap, even though it’s still really hard even after having a few apps under your belt. That’s kind of the crossroads.

Rob: Yeah and it’s never clear cut. You and I sat and tried to look at what are the options here and what are the drawbacks because you don’t want to fall into exactly that trap. Like the conventional wisdom says, “Do more customer development upfront, have a lot of conversations, don’t waste time writing a bunch of code, get it all settled out of front.” But it seems like your gut feel and mind in essence, too, was by the time we get to the end of the conversation it’s like your intuition of what it should be, since you’re trying to invent something new or at least innovate enough in a medium that’s chat, but you’re trying to do it differently, and it’s like, “I’m not sure that having conversations with people about mockups is going to get you there.” It wasn’t like you should absolutely do A or B. We both by the end leaned towards, “Go build something,” because until someone touches it and clicks a button, and even if it’s a fake simulated chat with an invisible person, with a bot, or whatever, at least they’ll get an idea of like, “Oh, that doesn’t make sense at all,” or, “Oh, it does,” in a way that I don’t know, you can’t get your hands on mockups the way that you can with some code.

Derrick: Yeah. If Steve Jobs would have taken some wireframes of the iPhone and showed it to people, would people have caught the magic? I don’t think so. It would look like an interesting concept, “Oh, it’s a phone that you can web browse on, and have all these apps, and these games. Interesting.” It’s hard to represent the user experience aspect of it, which I think for Level is a really big thing. It just has to feel right to people. As opposed to some other apps where it has this very specific utilitarian purpose, and as long as it can deliver on this purpose, then it will be good. Level is not necessarily good even if it delivers on the purpose, it also has to feel right.

Rob: I want to touch on the thing you said about Steve Jobs. I feel like some people will throw that around. He’s also an exception. Henry Ford talks about the model T being a faster horse or whatever, which I think is actually apocryphal. I’m not sure that he ever said that, but the idea is that I’m an innovator and I know better, I’m never going to show such to customers, and that’s what has gotten people into the two years of coding in your basement thing.

One I think is knowing your strengths. You happen to have really solid strength in app usability and design. I think both you and I were like, “You’re probably going to do a better job of this than most people would know, so take a flyer on it,” and two, I think it’s a gut feel. It’s like how strongly do you feel that you know what’s better in this space? Are you like, “I don’t really know the solution and I truly do need the input of 10 or 20 potential customers,” then think I’ll do that. It didn’t seem like you needed that. That’s what we were pulling out. You had enough of an image in your head of what you wanted to do that we thought it was worth the gamble. That’s how it felt, right?

Derrick: Yeah. I think that this is also one of the other things that complicates getting that type of feedback from wireframes for Level. It’s the type of product where if someone came and asked me, “Here’s what I’m thinking for a new tool that solves this problem, what do you think?” I would be like, “I don’t know if I could answer that very accurately either,” because I’d be like, “Well, it just depends on if I use it for two weeks, go through my day, and a bunch of stuff isn’t falling through the cracks, or do I truly feel like I am able to retain focus better, or am I constantly drawn to go check it?” There’s a whole story that has to come together. I don’t know if I’m imaginative enough to be able to answer with confidence like, “Yeah, I think you nailed it.”

Rob: All startups have some type of risk, whether it’s a market risk or technology risk. It’s almost [UX 00:10:14] risk, or threading the needle of being that’s the riskiest thing. We know you can build the app and you’re probably going to market it pretty well. I think there is some market risk in terms of, is the market of people who don’t like being interrupted by Slack, how large is that market? That’s an open question, but that’s one that’s very hard to answer until you build something cool right now. At that point, you made the decision to not have more conversations, and not build mockups, and you got to code in September.

Derrick: Yeah.

Rob: And then October, you did your early access phase. It was like pre-early access or something, right?

Derrick: Yeah. I’ve already been building foundations leading up to that point. So then it was just locking in some decisions around how the inbox works and some of the other elements in the product. I was only a few weeks away from being able to show it to people. At that phase, now looking back, it was very early and it would have been a pretty big ask to have any teams really switch off of their existing tooling and use this. There are just elements that people had come to expect in a communication tool that were just not present in Level.

I got good feedback, a good amount of like, “Hey, this feels a little bit off. This kind of thing works junky when I use it. It might be a bug.” It was valuable in a lot of ways, but it didn’t provide all the value that I hoped it would. I kind of, at one point, hoped that some people would actually switch off their existing tools and then it became clear that it just wasn’t there yet. There was still more that needed to be built.

Rob: That’s interesting. You showed it to customers, you got some feedback, but you felt like it maybe wasn’t worth it. You didn’t get enough feedback to warrant all the time at that point.

Derrick: Yeah. It goes back to that analogy of what is an MVP? Is it up a half-built product or is it just a simplified version of a product that will eventually grow into a more full-featured thing? I think at that phase, it was a bicycle missing a wheel.

Rob: Rather than a scooter or something, right?

Derrick: Yeah.

Rob: That’s interesting. We jumped ahead in November and that was when you decided to set a public launch date. It was a public launch date but it was essentially of a minimum viable product that you thought teams could use. You set that date for January 21st which is a few days ago now. What made you decide to put a stake in the ground in November and set a date?

Derrick: There were a few things leading to that. One is I was becoming really impatient with it not moving to that next phase. Part of it was for my own psychology. I wanted to have this date set. I actually was kind of inspired. We were interviewing Paul Jarvis who just released a book in January.

Rob: Company of One.

Derrick: Company of One, really good read. He was doing his press tour for that promotion and stuff. I remember seeing everywhere that he was showing up, he was talking about, “The book is coming on January 15th,” or whatever it was. I’m sure that’s kind of an artifact. They’re just weird publishing schedules, and working with traditional publishers and stuff. But it kind of inspired me like it would be kind of nice if I could be talking about Level and have a date. There’s a date that is coming, and so start building momentum up to that, partially for myself, partially for people who are following the story, and getting excited about it. I was ready to give something a little bit more into the public conversation. That was a big piece of it.

I’ve been toying with the idea of doing presales for the product. Some people are more aggressive with this than others, some people as soon as they have the idea, they’re asking for money right away. I feel like that’s just something you have to take on a case-by-case, founder-by-founder, what you’re comfortable with, what market you’re in, and so on. For me, I felt like to be most comfortable asking for money, I wanted to have a date that I could use and say, “If you put down a deposit today for Level, you will get access guaranteed by the this date,” that was another big piece of motivation.

Rob: I can see that. In retrospect, do you think it was a good decision to set that date?

Derrick: Yeah, I think it was great. No regrets on that. I actually probably could have pushed it earlier. There were definitely things that always happens with launches a few days before. I’m like, “Oh, it would be nice to get that in.” I was working around the clock a few days leading up to Monday, slipping in things that were just like, “I would really love to have this. When I’m demoing the product, I want this part to really shine.” I definitely procrastinated a little bit but I think I could have probably pushed it even a little bit earlier. Being close to the holidays and stuff, I just wasn’t sure how hosed my work schedule would be over that period of time. The value of having a public deadline, there’s many benefits to it. No regrets.

Rob: What did it do for you? Did it just motivate you like, “I have to get this done so I’m going to work more cut scope”?

Derrick: Yeah. I think it’s a really good forcing function for bringing clarity. I fall into this trap all the time. I pay close attention to detail about stuff and I’m very particular about UX. I could easily just keep iterating on small pieces and burn hours on that. I definitely have done my fair share of that. Even still with all these pressures I put on myself to keep focused on the most important things. I think deadline is even more forcing function than just me telling myself to stay focused.

Rob: Yeah, that makes sense. I feel like one of the purposes of deadlines in our space is that, people who build great products almost without exception are perfectionists. They never think it’s good enough because their taste in products is so high. That’s how they know when it’s good, because their taste is good. If your taste is good, you don’t want to put something crappy out. To you, crappy is like things that everyone else looks and says, “Oh, that’s so amazing and gorgeous,” and it’s like, “No, it’s one pixel off of this and that,” at a certain point, you set a date, and you just force yourself to do it.

We’ve done this a couple times already with Tiny Seed where we just go up and decided to announce in October, and we’ve set a forcing function of getting this first batch picked out before MicroConf which is end of March, and that feels incredibly ambitious. I stress about that every day, but it’s good. It’s made me motivated. It hasn’t made me work more hours, but it’s making me be way more focused on the important things. Anything that’s not getting me closer, getting us closer to that objective, I’m just putting on the side. I think it’s good.

Derrick: That’s why I like the concept of healthy stress which has been well studied. There is a certain amount of stress that’s good. I think it’s kind of like that Basecamp mentality. They talk a lot about how they work and how they set these six-week cycles. At first, when I heard Basecamp has deadlines, that seems opposite of how they work. I thought they were calmly, and work at a natural cadence, and not overly stressed, but once you dig into their philosophy around that, it’s like, “No, we set deadlines. No, we cut scope around those deadlines. We don’t burn ourselves out, or make people toxically stressed, and pack in a bunch of work that’s unrealistic. We just pull the other levers to make it happen.” That’s what I found. I’m either going to work around the clock, obsess about every single detail, and try to pack in a bunch of features, or I’m just going to set aside my compulsion to perfect everything, and just focus on the most important stuff.

Rob: Cool. In November also, you mentioned you did a presale in essence. What was the purpose behind that?

Derrick: Yeah. I’ve wanted to do that for awhile and then kind of setting this deadline in my mind, made it kind of feasible to propose this to the public. My rationale was I wanted to figure out, at that point it was probably close to 4,000 people on the launch list who reserved a handle on Level. That’s a lot of people. There’s a lot of people who are supportive. I’m doing a lot of working in public, on Twitter and stuff, sharing my work.

There’s quite a few people who seem to really be following along with the story and glad that it’s happening. That still doesn’t necessarily translate to who’s actually feeling the pain enough to hand over their hard earned dollars for a solution. For me, this was like getting that set of people who are most feeling the pain, most willing to pay, and those are the ones that I want to be getting into the product first, hearing their feedback, and kind of building off of that.

Rob: It’s a good filter in essence is what you’re saying. You just picked out a number out of the air if I recall. It was $48 which is six times your Percy pricing. It’s $8 a seat, right?

Derrick: Yeah, right.

Rob: How many preorders did you get? What was your total preorder amount? I’m curious.

Derrick: I think it was around $2500. I’m not good at mental arithmetic. I think it was 55 or 56 people who went to buying the preorder.

Rob: Were you happy with that? Did you have a number in your head in advance?

Derrick: I didn’t really know how to declare success or failure on that. I felt happy with it. If I got 20 people, I was going to be happy. That felt good to me.

Rob: Cool. Let’s jump forward. It sounds like the holidays, December was a lot of coding. Even early January you were heads down, you’re just trying to get stuff done and meet this deadline. Here we are, we’re recording the week of the 21st, even though it’s going to go live next week. You talked about doing seven calls so far and you have another half dozen or so scheduled. How is it feeling? Do you feel like the product’s at that point where it’s a good time to do it? Are you getting a lot of value out of this or is it still too early to tell?

Derrick: I’m feeling overall positive about it. I think I had to temper my expectations, because the switching costs for a lot of organizations is pretty high. For better or worse, Slack starts out as just a place for humans to talk to each other within their organization. Gradually, some organizations decide to kind of turn it into this place that runs a bunch of their internal workflows, maybe the sales team relies on it for leads to come through into a specific Slack channel which then they can follow up with.

For some people I’ve talked to, it’s proven that this is going to be a longer process. Overall, the response has been positive. Even from those who have more complicated set up, it’s still like, “This product looks really interesting. I’m intrigued.” But the gap between me being intrigued as the champion in my organization, and us actually switching over to it, for some, the gap is pretty big. I think it’s a reminder to me that I need to be patient and just set my expectations properly.

Another artifact of this is that Level is going to be most impactful for teams that are a little bit larger. Really small teams just don’t feel a lot of the pain that teams that are growing start to feel when Slack really becomes unwieldy. That’s another thing that I’m keeping at the back of my mind, set those expectations properly. I’m really feeling positive about this model of staying in the zone of vetting people who come into the funnel, that alternately make it into a demo with me, who ultimately get into the product to try it out, as opposed to doing the big splash public launch, let in a bunch of people, get a big spike of interest, and then a majority of them turn out, and probably send in feedback along the way that I don’t really know if I can trust because I don’t know if they’re a good fit in the first place.

Rob: It’s going more after the super human model, right?

Derrick: Yeah, exactly.

Rob: Derrick, do you remember a day maybe 5-10 years ago where you dreamt of just building a self-service software product that paid your bills. Is that why you got into this?

Derrick: I think so, yeah. My very first product that I remember throwing something together and then I literally Googled, “How do I get customers?” I just thought they would come.

Rob: Yeah. Now here you are, doing heavy hand-holding, onboarding, and conversations It’s good stuff. It’s just crazy how it changes especially as your goals change too, I think. You want to build something great and you want to build something that I’ll say is a decent sized company, whatever that means to people. I just don’t know if you can do that anymore, trying to go no touch. It’s really hard. I shouldn’t say you can’t, but it’s really going to be one in a million or something to just thread that needle and have the Cinderella story. You’re putting in the work. This is what it’s about.

Derrick: Yeah. I feel the no touch phase will come once the product market fit is extremely tight. I feel everything I am doing now—of course I didn’t come up with any of this, these are things that people talk about—going through this phase of intense hand-holding, keeping the filters on really strong, for this round of folks, of the people who put in a preorder, I sent them a questionnaire, asked a bunch of questions about what are the current problems in more detail with chat, what tools are they using, how big is their team, are these for project management, what does email look like in their company. Just a bunch of things I felt like would be good inputs into me understanding their use case, and being able to cater my demo to them, and set my own expectations on what I expect from them. Not everyone has submitted that questionnaire. Not everyone got a Calendly link to get on my calendar to then get into the product yet.

I’ll keep nudging to other people who have preordered and haven’t done that yet. I want to keep the filters really tight because what that does is ensures that I’m getting the best quality feedback that I can possibly get, to then hopefully lead to more of these folks coming through the pipeline, and getting just tighter product market fit.

Rob: You put in the kind of grinding out customer development now so that later on, you have that fit and you know that you can market it and self service it. It’s a good way to think about it. If you think about it, it mirrors very closely what we did in the early days of Drip. You were off coding and I was doing what you’re doing. I was either having calls, or doing videos, so that you could keep moving full speed. In this case, you have to do both because you’re a single founder. I’m pretty proud of what we built with Drip. It had product market fit. Once we nailed that, growth really kicked in. It’s a good kind of analogy or parallel thought there.

One of the things that you’ve done well is, you’ve built up this launch list of almost 5900 email addresses. It’s people who wanted to reserve their handle, and they probably want to follow along, and might want to use Level. There’s all the reasons but I’m curious, for listeners out there who haven’t built a lunch list yet, the first question is what’s the value of that launch list? It’s probably pretty obvious, but I talked through that a little bit and then how did you do that?

I know you have a podcast Art of Product, we should plug it here. Folks want to hear two software founders who were getting it done and building interesting products. They talk every week, you and your co-host Ben that’s artofproductpodcast.com. You have a podcast but that didn’t get your 5900 handles. Talk to us about the value you see in it, and why you spent the time to build it, and then talk through a couple things you’ve done to do that.

Derrick: I think the benefits of having that email list, it talked about a bunch. You’re going to have a certain conversion rate on your list, ultimately. The larger you can grow that list, hopefully the more customers you’ll have come out the other end. When it’s really early, I don’t know how well qualified everyone is on that list, but I know that right now I wanted that to be a very wide top of funnel, just get people onto a list so that they can have a chance of hearing about what I’m up to, and hopefully converting if they’re kind of in the camp of a good, ideal fit.

What really cranked up the number of people submitting the form was adding that scarcity piece, that reserving a handle. When I did that, it obviously has to fit with the kind of application that you have. If you don’t have something where there will be a user name, then it wouldn’t make sense to do that. I think introducing some element of scarcity is just enough to push a lot of people over to, “Well, I don’t really know, but I’ll at least drop my email in this,” they’re getting some kind of perceived value in addition to just getting email updates.

I actually don’t have great historical metrics on conversion rate of hitting the homepage to submitting, but my traffic is not that huge right now. It’s a pretty high percentage of people who land on the homepage will submit that form. It’s not like I have a huge amount of traffic coming to the website, but if I look into my analytics, I think a majority of people are either coming from Twitter, links on Twitter to Level which is where I’m predominantly talking about in the open what I’m working on day-to-day, and just direct. People who either hear about it on the podcast, or hear about it from someone else in person, or whatever, just typing in level.app and coming directly there.

I think I’m kind of playing a long ball with this, but from the get go decided I was going to be as open and transparent with the development process as possible. The thinking behind that is just, people are interested in following a journey. Starting out the Level journey with the manifesto, I think that resonated with a lot of people. It gets people curious about how this is going to all come together, and then in the process of sharing openly what I’m working on, also trying to just be useful to other people. It’s something that Adam Wathan and Steve Schoger are really good at with their newly launched Refactoring UI.

A core part of their strategy was to provide hot tips on Twitter and just be insanely valuable. Giving away a bunch of free knowledge and just stuff that is part of their day-to-day work that they can just package up and share in a way that provides value to other people. That was insanely effective for them. I’m following that same similar strategy of just trying to share a lot. I think it’s built up a decent amount of people who are just genuinely interested in the story. That leads people to when they sign up for a handle, they are more likely to tweet about it and tell it to their friends. That leads to more people signing up. It’s just kind of a nice little flywheel there.

Rob: Yeah, that’s nice. One concern that I have with that approach, especially with SaaS, it’s different than what Adam and Steve are doing, is that SaaS is a tool and people pay for it on a monthly basis, whereas Adam and Steve sell info products. They sell books and courses on the topics that they’re tweeting. There’s a tighter alignment there. I think their conversion rate will be very high and I think yours will be less. It was that way when we were doing Drip as well.

I don’t know if you remember but the first 500 people on our email launch list were mostly for me talking about it on this podcast and a couple other places. The conversion rate on those was far less than the ones that I got from other avenues. It’s not a bad approach, but it might give you a false sense of security. I don’t think you’re kidding yourself in thinking that everyone who wants to follow your story is going to sign up for Level. I want folks at home, if you’re listening to this, realize that there’s difference here.

I still think it’s a viable approach, and it’s something I would be doing the same, but you have to have it in the back of your head that these people are probably not going to convert as well as if you’re running a targeted ad campaign to only the demographic that gets value out of it. If they give you their email and they’re more of a cold lead, they almost might have a better chance if that’s a real pain point for them, versus someone who’s listening and is just like, “I want to follow along and see how Derrick is marketing,” right?

Derrick: Yeah. That’s a really good point. One thing that is in my favor that is not universally in people’s favor when they’re working out in public and sharing their story is that, the people who are potentially good candidates to become Level customers are developers, designers, founders, and that’s the people that are in my tribe on Twitter. The community that I have some degree of access to that are interested in the story, they’re interested in the meta story, they’re interested in the startup journey because there are other startup people, and this just happens to be a tool that is being sold to other startups and founders and stuff like that. If you’re building countertop installer software, sharing your story to other developers on Twitter isn’t necessarily going to move the needle at all.

Rob: Exactly. I’m curious, you had to buckle down at some point, put a stake in the ground, and make some hard choices, and decisions about the inbox. This is as you said, it’s the most critical part of the app because if it works, it’s magical, and angels sing down from the heavens. If it doesn’t, then it’s just a big point of your app that really needs to go well. How did you finally decide to buckle down and just say, “I got to make a call on this,” because I know that you’ve thought about it a lot and it was a long process there.

Derrick: I think I don’t have any other choice. I have to do this. I have to just follow my gut instinct and know that I may have to change this. It may not be a perfect implementation and it’s something that I have to fight against because now that I’ve been through Drip, Codetree, and all these experiences, I am very aware of the cost of legacy code and technical debt. Part of me was like, I don’t want to write any code unless I’m sure that it’s going to not have to change in a significant way.

I had to get past that a little bit and know that there’s always going to be a tension between writing well-crafted, well-tested code that you’re going to invest a lot of time into making it really rock solid and know that you’re potentially going to have to change a bunch of that, and rework data models, and rip out database tables, and do launch data migration, or whatever it may be. I ultimately just had to make the call that I’ve got to do this, I’ve got to get it in the hands of people, and then hopefully the mutations are relatively small, and I can just dial it in with smaller refinements, but also know that maybe it is larger shifts that need to happen.

Rob: How about the experience this time around? In essence it’s your third app, but you had two or three before that. It’s like the fifth or sixth project. You’ve had a lot of experience doing this, so reflecting on it as someone who has launched and grown things in the past. The last nine or ten months when you look back, did it take longer than you thought? Less time than you thought?

Derrick: Yeah, I think my big takeaway is this stuff, regardless of your experience, never gets easy. It gets easier in some ways, but there are fundamental truths about custom software development that still hold regardless of how experienced you are and knowing that there are some of those pitfalls that arise once you have some battle scars. The first time around in earlier apps, I was probably less concerned about scaling challenges for example, because figuring that rightly so that will tackle those problems when we get there.

Now, coming out of an experience with Drip where there were a ton of scaling challenges, I think it’s been a difficult thing that I’ve tried to stay aware of not prematurely optimizing things, or planning to much in advance for scale that I don’t really know what scaling challenges will look like, so try not to invest too much into over-architecting stuff. It gets easier in some ways but then also gets harder in other ways once you have more experience under your belt.

Rob: Yeah. I made a mistake or just a judgment error after HitTail as we started Drip. I thought that it would go faster because I knew more, I had more experience, and more knowledge, and it didn’t. I remember being very frustrated by that for a year. Your mindset and your expectations can really negatively impact your experience of an event.

Derrick: Yeah.

Rob: That’s what you’re saying, don’t get overconfident. Parts of it get easier and you do get better at it, but I don’t think you get faster at it. There is a difference. Look at David Cancel, who’s on his fifth or sixth, all have been successful and exited. Right out of the gate he raised $5 million, or $10 million, or $15 million, it was a huge number, right out of the gate as they were starting. He’s been grinding on Drip for years now, and yes they have traction now, but the first one or two years, it was not getting the traction that I would have expected from a founder of his experience and caliber. Even Jason Cohen with WP Engine. WP Engine is huge now. Remember him bootstrapping and toiling away for a year-and-a-half or two years before anyone had heard of it? It’s crazy.

Derrick: Yeah. When I look at the product, I’m trying to keep Level very simple and elegant. I looked at the product today and I’ve been spending a lot of time in it obviously using it myself. The mechanics of this feels very simple. On the one hand I think, why did it take me so long to arrive at something that feels so simple? It feels like given all this time and all this effort, it should be something that has thousands of dials and tweaks to it, and just like this very complicated system. Just looking at a product that looks simple on the surface doesn’t mean that there weren’t thousands of hours of thinking, and laying on the floor, staring at the ceiling, trying to figure out the most elegant way to execute this. It’s even hard for me sometimes looking at my own product to say, “Why did this take so long?” but it just does, because these are hard problems to solve.

Rob: For sure. Well sir, I think we’re at time. Thanks so much for coming back on the show.

Derrick: Cool. Thanks for having me.

Rob: If folks want to keep up with Level, that’s at level.app, and if they want to hear you talk about it every week, it’s artofproductpodcast.com, or they can head to iTunes, Stitcher, wherever fine podcasts are sold. Have you gotten into Spotify yet?

Derrick: We are in Spotify. Actually, that just happened. We use Fireside for hosting our podcast and they just did it one day. I just went in and I’m like, “Oh, I guess we’re in Spotify.”

Rob: Yeah, that’s cool. Good for you. Folks have been requesting that we get in Spotify and I was like, “How do we do that?” [00:37:57] research [00:37:58] and appear that because we self host on a shared hosting thing with a CDN over it, we don’t use any of the fancy big hosts that kind of do it all for you. It looked like we were going to have to move hosting, copy all the files, and do 301s, and I was like, “I’m not sure this is worth it,” but as it turns out, we missed a link to the first look around. So when I submit our RSS feed 15 minutes later, we were in Spotify. I was like, “Yes. [00:38:22]. It’s great.” Well, thanks again sir for coming on the show.

Derrick: Thanks for having me Rob.

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One Response to “Episode 429 | Building a Launch List of 5,900 and Grinding Out Customer Development”

  1. Christian says:

    Love the show and thanks for keep sharing your knowledge and experience (please keep doing it! 🙏).

    I wanted to say that the reasons why Derrick started building Level instead of investing on customer development seemed to me pretty weak.

    I understand that the benefit of using Level over Slack is something that needs to be felt and perhaps not entirely appreciable from mockups. Still, this sounds like the type of product that would really benefit from a large study in Slack’s users pain points.

    I would also be cautious in forgetting the benefits of faking a product (through high-res prototypes). Both for validation but also for creativity, especially in products where the UX will be quite important.

    Thanks again and love to all ❤️!