remote teams

Rob: Welcome to this week’s episode of Startups for the Rest of Us, I’m your host, Rob Walling. This week, I’m trying out a new episode format. It is a discussion show, so it’s a conversation between myself, my old friend Derrick Reimer, and we talk about a number of topics. We talk about the value versus the stress of Twitter and social media in general, the pros and cons of remote work. We talk about Cal Newport’s new book Digital Minimalism, and then we wind up talking about Josh Pigford’s blog post in the Baremetrics blog that’s titled, I Almost Sold Baremetrics for $5 Million.

What I like about this episode format is it’s pretty casual and we’re covering topics that I think are relevant to many of us and a lot of us are thinking about. I originally thought of structuring this in some type of news, round-table, or show where we’re talking about topics of today. We do that with a couple things, I think the ability to introduce topics that aren’t necessarily news articles or news headlines also works, and the fact that Derrick and I know each other as well as we do really helps with just the rapport in the conversation, it’s not stiff or stilted. I hope you feel the same way about that.

If you don’t recall who Derrick Reimer is, he and I have known each other for years. We met back when I lived in Fresno. He was a young kid who was participating in a startup competition that I was the judge of. He won a couple years in a row. Then, he was thinking about starting to do some consulting work and I said, “Look, why don’t you come, write some code for HitTail?”

He wrote all the early code for Drip and later on, became retroactive co-founder of Drip. So, he and I have known each other. We’ve worked together. He’s been on the show several times talking about starting an app on the side called Codetree that he sold for $128,000 a few years back. Then, he moved to Minneapolis when we sold Drip. So, he and I now live six or seven minutes apart.

We see each other once a month or so and it’s always a good time to hang out and chat. So, I wanted to mix up the format just a little bit and do something that’s not an interview, not keeping up with Mike Taber, not just question and answer, but actually just bringing topics to the table that (I think) might be of interest to you. So let me know what you think.

You can tweet me @robwalling, you can email questions@startupsfortherestofus.com, or you can post a comment on this episode, episode 482 and just say, “Yeah, I enjoyed the mix-up of the show format and the fresh ideas in a conversation.” Or you can say, “Got five minutes in, didn’t hold my attention, and I was out.”

That helps me think about and consider maybe we had one of these to the line up every couple months. It doesn’t always have to be Derrick. I could bring on different co-hosts and folks to weigh in, so we have different perspectives.

And with that, let’s dive into the show. Derrick Reimer, thank you for joining me on the show.

Derrick: Hey, thanks for having me again.

Rob: Yeah, I think this is going to be a fun one today, just talking through some interesting topics. I had a few in mind over the past couple weeks, some things have come up where I’m like, “You know, I really want to discuss these with someone,” and I don’t know who to bring on the show to do it. Then, you and I were having dinner last night and we got on some really good conversation topics, so I figured we could jump on the mic and record a few of these.

Derrick: Yeah, we both are a couple of old-fashioned, but we probably should have brought our mics, to be honest.

Rob: I know, I agree. One thing you kicked off with was just talking about something on a lot of our minds, social media in general but Twitter specifically, because that’s big in our circles and the value versus the stress of it.

Derrick: Yeah, for me, my personal journey with it has been the last remaining piece of social media that I really use these days. I’ve given up Facebook, technically, I have an Instagram account but I don’t really use it, and I’m not really hooked on checking those things. But Twitter is a tricky one and I think it is for a lot of people in the text space because it’s where a lot of our industry news is coming from, where a lot of the camaraderie among software developers and start up people is happening. There’s not really (to my knowledge) another platform like it.

There are niche communities in Slack and things like that, but Twitter is the public square for that. It’s been a struggle (I think) for the last few years. I’ve been saying things like, “Yeah, I’ve given up all social media,” but I can’t on Twitter because that’s where work stuff happens. I just become so aware that, for me (and I think it varies from person to person how they deal with it) it’s like Twitter is always the default. I hit a rough spot on something I’m working on and what’s my first inclination is to go check Twitter, go get a dopamine hit, and I’m over it at this point.

Rob: Do you still have it on your phone?

Derrick: I took it off my phone (which has been good) and I actually did another trick where I put all my apps in one folder, so now I just have like a blank desktop screen essentially on my phone. I keep email on there, for example, because I just want to be able to do email mobily, but I don’t want it to be something I compulsively check if I have a break during my day. That’s been a good way to deter that.

Rob: When you put them all in one folder, was it just to make them hard to find?

Derrick: Yeah. It’s like I had muscle memory built where I knew where to tap my thumb subconsciously to open email and now it adds friction to that.

Rob: Yeah, I do that. I’m compulsive with email and Slack, specifically the TinySeed Slack. I don’t do it with Twitter or Facebook and I’ve never really had that problem, but I definitely can see getting into that habit and I try to avoid it. I think the thing with Twitter is I check Twitter a couple times a week and (for me) that’s a pretty healthy balance.

I might post to it more often. A few months ago, I was posting every day and I fell off that wagon. I’d like to do that again, but checking it all the time is not healthy. That’s what you were saying last night. It doesn’t feel good because you’re going for the dopamine hit of someone replying to you, a conversation, likes, or retweets?

Derrick: Yeah. I don’t know if I’m feeling particularly just unsure about something I’m working on or just my business in general, all these existential mini crises we have all the time into building startups. That’s an easy place to turn where I’m going to share some piece of work that I’m doing and it’s going to have some marketing benefit. It’s going to increase awareness about what I’m doing and hope people will spread it around. Maybe someone new will discover my app.

I can justify that there’s some benefit to it, so then I’ll share something and it feels good to get people liking, engaging, and commenting, but it’s pretty hollow and it’s a veneer that’s providing a short-term benefit, but I don’t think it’s the healthiest way to engage with that. Then, when you don’t get the response that you were hoping for, then you feel bad. It’s like, “Why am I doing this in the first place?” This is not a solid way to go.

Rob: Yeah and the struggle is that it’s not just the social aspect. I know you got off Facebook years ago and I think it was easier to justify because there was no work component. There was no way Facebook was going to help you build or grow a company, whereas Twitter might (and I want to put it in italics and bold). We know folks who have personal brands on Twitter, social media empires. I don’t know of anyone who has built a SaaS app and the marketing was all Twitter.

I view Twitter as you can get a small audience and you can get those first few customers or you can get the first people who are going to give you good feedback. It’s part of just building that relationship with people, but realistically, once you have any type of product market fit and you’re actually trying to build a scalable marketing approach, Twitter is not it. If you’re looking at it purely as a utilitarian thing, there’s definitely times and places to do it and be on it, but with all the negatives, it does feel hard to justify to me.

Derrick: Yeah. You can definitely come into it with the strategy of like, “I know the best times a day to post where I’m going to maximize engagement,” I figured out some of those things for myself. Some of it, you can apply methodically. Other parts of it are a lot of the benefits that have come to me has been serendipitous and that’s where I have a little bit of fear that if I were to give this thing up, I don’t know what I’m giving up entirely. I don’t know what random encounters or  interactions I might be missing out on and I think that’s for the fear that comes. This could be the thing that catapults my nascent start up into a different realm, if I were just there engaging in the community on Twitter. In reality, I’ve become pretty convinced that’s probably not a very good reason to accept all the negatives.

Rob: I keep doing it, yeah. You make a good point because it isn’t just finding customers, but what about that one relationship you build with the business development where someone says, “Let’s integrate. We’re a web host so let’s integrate.” You’re like a kid and you’re like. “Yeah, that could move the needle.” That’s what you’re saying, it’s like, “Do I want to miss out on those? What’s the potential?” and that’s where they get you. That’s where […], is it has all these negatives, and yet we still want to consider doing it.

Derrick: Yeah. If I think back, I’m frustrated by how many Twitter DMs have actually led to productive business meetings or chats and it’s like, “Why does that have to come to a Twitter DM?” because that’s just reinforcing that I struggle to actually get off of there, because people would have to find my email address or something.

Rob: Yeah, and it does seem like Twitter has declined pretty substantially in popularity. That’s been my sense and just the number of people on it. Obviously, the tech community, the Silicon Valley, plus MicroConf and just startups in general are on there. And the press. It does seem like there’s a lot of journalists, not just like TechCrunch but like Wall Street Journal, big-named journalists are on there and there’s certainly still some value. Remember Arab Spring, there is communication there, there is value to the world that that stuff is able to get out.

It really does seem like people have moved on to Instagram and what are the others? Snapchat, although I guess they’re on […] now. You mentioned TikTok last night and I was like, “Yeah, I’ve heard of that. No idea what it does.” I’m so old dude.

Derrick: Yeah, we’re getting old.

Rob: What are you going to do? If you listen like I was asked on stage, “Are you bullish or bearish on Twitter?” and I was like, “Bearish.” This was last year. I was on my 2016 or 2017 prediction. This is when Twitter was still going strong. There are going to be too many trolls. People are just going to move on, and the nature of social media is that it’s pretty rare for a platform to actually stick around for that long. People just move from one to the next.

I don’t love Twitter and struggle with a lot of stuff on it, although I am still on it. I think there are benefits, especially now with the MicroConf stuff, the podcast and all that. I’m not going to quit Twitter anytime soon, even though I do have some struggles with it. But I’m curious, you’re seriously thinking about getting off of it or quitting it basically. Is that right?

Derrick: Yeah. I’m getting dangerously close to that. For me, my big fear is how am I going to keep a similar type of connection to people in the industry who I’m not so close with? I’m texting or private messaging all the time. How am I going to maintain that? How am I going to still get up-to-the-minute news about stuff? I see a lot of things in the React community, for example. New things emerging or new releases of things and a lot of that I’m getting through Twitter right now.

It’s important for me to know about that because I’m building tooling in that ecosystem. I don’t always want to be the guy who’s a month behind late to the party knowing about stuff, but a lot of these you can think of it as, is that really so bad if you’re a few more days delayed in finding stuff out? Probably not. In that case, for me, I’m trying to look for what are some digests newsletters for example that are in the industry? I’m already a part of some of these.

The Changelog is one of them. They send a weekly summary of what’s happening in the open source world. There’s one for the Jamstack community, too, and I’m on that one. I get a lot of good info from that. These are probably good enough for the news part. For me it’s like, how am I going to keep connection to my “audience?”

The podcast is a good one side of a way to do that. Again, returning back to the fundamentals. My email list, my newsletter list, how can I invest there? The time I maybe would have spent on Twitter carve out some of that time to try to invest that in the email list. Those are some of the ways I’m thinking about it.

Rob: Those are good alternatives. I was going to propose that mailing list and a couple of those other things. The bottom line is, yes, you may miss out on some things, but take the time and invest in stuff. I would say, investment in stuff that is less ephemeral.

That’s what bothers me about social media. It’s just here today and gone tomorrow. It’s not a blog post. It’s not even a podcast episode people go back and listen to. It’s not a book that people will read for years.

With your email list, if you can invest in an email list and repost that on the blog, because email is a bit ephemeral even though it’s a pretty deep connection. That’s when I’ve been off because the entire time we were doing Drip, I was not on Twitter at all. It was the right choice. I didn’t quit it for life though, I came back. Obviously, I’m a little more active on it now, but I do hear what you’re saying. If you tried it for two weeks or 30 days, or something, my guess is you’re not going to want to go back.

Derrick: That’s a good segue, because I’ve been reading a book, Cal Newport’s latest book called Digital Minimalism, which is like Deep Work. A lot of people know about that one. It’s Deep Work principles applied to more of your personal life and how you interface with things like social media.

One of the things you he talks about in there and recommends doing is like a digital declutter. That’s a term he coined for. Basically, taking 30 days and eliminating the things that are causing you problems like social media, that are pulling at your brain and causing it to be distracted, and all the negative side effects that come with it.

Think of this as you’re eliminating all this stuff and then at the end of it, be really deliberate about what you add back in. Don’t think of this as just a temporary detox where you remove all and then at the end, I’ve reset and now I can go back to the way I was doing things.

I’m in the midst of one of those right now. I’m not deleting my Twitter account, but I’m not checking it. I started this off going on a trip where I had very little internet access. That forced me to step away from it and even coming back from that after five days, I already had much less desire to go check it. I do feel a certain amount of Zen just from that. That’s becoming a reinforcing thing already for me. The more time I spend off of it, the less drive I have to go and check it all the time. That’s been healthy, I think.

Rob: That’s cool. How long have you been doing that?

Derrick: Since really the turn of the New Year, so we’re about two weeks in. It’s been good.

Rob: It’s a trip when you change habits like that. How scary, you don’t know if it’s going to work, and then you get in a few days and suddenly you feel this clarity, and then trying to come back to it. I’ve done this with drinking alcohol, social media, or just anything. I enjoy it. There are pros and cons to each of those things. It’s like if I have an old fashion, I feel better. In the short-term, it’s a good thing. Much like checking Twitter. Then in the long-term, I question the value of doing that and going off of those things. Coming back, you just realize how much it impacts your day-to-day or just how it actually affects your life.

Derrick: Yeah.

Rob: And you were saying last night because I haven’t read Digital Minimalism, but you piggy-backed on it and it got you thinking about remote work.

Derrick: Yeah. A thing that he spends a fair amount of time talking about in the book is what does it mean to have relationships and have real connection with other human beings. This is heavily tied in with the era of social media there of text messaging. The fact that we rarely call each other anymore. We are always texting. There’s all these norms that were established in society and a lot of them were around lower fidelity means of communication.

He makes a good point. This is based on some research he pulls into his thesis. We’re wired after millennia of communicating with each other, talking to each other, being able to read non-verbals and verbals, the whole picture, and now we’re reducing our communication down to very binary things. If you think about what’s a reaction in Slack or a like on Twitter? It’s literally a binary piece of information. You compare that to all the richness that comes with someone reacting to something in person. You get to see their face, you get to see them smile, or see them look inquisitive. There’s just so much more you can get from it.

In the one sense, you can think of it as more efficient using these productivity tools like Slack, but on the other hand, how much communication are you missing out on and what does that do to our mental state? You make some pretty interesting points that there’s high rates of depression and mental health among college students in the generation that grew up with smartphones. That’s starting to become really evident. There’s been some research at universities about this and just a really sharp increase in a lot of these issues that weren’t a problem before.

You take all that, bundle that all up, and I start thinking about how are we architecting companies? How are we building teams? I feel like a struggle that you build a 100% remote company. How often do you really have that high fidelity communication with each other? That’s what got me thinking about that.

Rob: It’s tough. My personality is I want to go against the majority opinion. It’s like, “Hey, everyone’s raising venture capital.” “Cool. I’m going to go start one without venture capital,” and that’s going to be a bad thing that I talk about. Or, “Hey, all these Fortune 1000 companies or even venture capitalists want you to be located in one place.” “Cool. I’m going to go start a remote company.” That was what you do and it’s a natural thing that I want to do.

In addition, we have the Remote book by DHH and Jason Fried. It’s definitely a thing and we know tons of startups, especially more in the non-venture track space that we write in, that are remote. And there are advantages to it. You can hire people in cheaper locations. You can hire the best people around the world. Everyone doesn’t have to be local, all that stuff.

I see the value of that for sure, but I’ve always said that the situation we had with Drip where half of us were in one city, and I would have loved for all of us to be in one city. We just couldn’t find the talent in Fresno. Half of us were in one city and we were in the office 2-3 days a week. That was my dream setup and I wish every job that I worked and every company I run, because now with TinySeed, there’s three of us and then with MicroConf, there’s two of us, and we’re all remote.

While I don’t think we should all need to live in the same city—it wouldn’t be practical, because (again) we wanted to hire the best people, and Einar and I are co-founders, he’s in California and I’m in Minneapolis—I would love to see them once or twice a week in person, which is what we did back when we’re doing Drip. And that’s so healthy.

Derrick: Yeah it felt pretty ideal. The nice thing was we can write the rules for how this works. There was inherent flexibility, we weren’t always on the same days every week. If something in life happens and you need to be out of the office an extra day a week, no big deal. But to have that as the default, it felt really good, like hopping in front of a white board with […] getting to work through some tough problems. I was never able to reproduce the same benefits over digital means and maybe someone still needs to solve that. Maybe we’ll get there.

Rob: Yeah, that’s the question that’s like will VR solve that at some point? Can you imagine if VR was super, super high fidelity, you and I can look around, literally feel like we are in front of a whiteboard together, and to get social cues, to where it’s uncanny “Valley” type stuff, like you see these amazing video games or even a Pixar movie. Humans look human enough that you can pick up all the stuff. If you and I can be in a room and literally look like that, maybe that would do it.

It’s a bummer. Some of the things I enjoy the most are lunches and hanging out, but I don’t know if you need that. Maybe that’s the point where it’s solved because video chat isn’t enough. Zoom is not enough because you are not going to sit on a Zoom call for 2–4 hours and shoot the breeze and get those moments that you need.

Derrick: That’s the thing. A lot of the way we are thinking about building companies and the tools that we are building for them, it’s introverted Silicon Valley-type engineers who are helping architects how we socially interact with each other. There’s an inherent bias in that. The fact that we are all about using tools for productivity, an important part of building a healthy team is actually having a relationship that has nothing to do with direct productivity. That’s more of a long-ball type of thing. If we are going to build cohesion, we’re going to be able to go to lunch together.

A friend of mine shared this anecdote, coming back after a long break and catching up on work over the holidays. His wife was relaying this to him and she said, “How was work today?” He’s like, “It wasn’t a great day, but I got to see my friends.” It was powerful. That’s something that you don’t necessarily have if you just stay, show up, and be productive. If your day is not productive, then you feel like you had a good day. If you get to see your friends, you get to see the people you built relationships with, then perhaps you’ll feel a lot more well-balanced.

Rob: Yeah. In Slack, you get the emojis and you get some fun stuff shared on a random channel. That’s fun, but it’s definitely different and it’s hard. Think about with TinySeed, we are a remote accelerator, so this is an issue. We get together three or four times a year and those times are really cool when we’re together. There’s a lot of bonding that happens being in person. That’s something that we are going to be facing and trying to overcome for sure.

In a perfect world, again, I just like seeing people more often. I’m pretty introverted, too. To your point about Silicon Valley people building tools, introverted Silicon Valley people thinking that remote work is, I won’t say infallible but it is the ideal. I don’t think it is for most of the world. I don’t think it is especially for extroverts for people who want to be around other folks. The loneliness and isolation is absolutely being shown. They are doing research on it, there’s going to be a real swing here depending on personality type. There’s a lot here that is not as clear cut as just saying, “Here are the pros of remote work and therefore we should all do it,” because it’s nowhere near that clear-cut.

Derrick: I feel like I’m starting to look at a lot of these things that I previously saw as absolutes and I’m starting to see a lot more gray in them. There are benefits, but there’s also drawbacks and you have to weigh them against each other. One cool anecdote that was from Cal Newport’s book, he talks about the Amish and he talks about how a lot of people just assume that it’s this community of people that decided arbitrarily like, “This is the peak of technology and we shall not accept anymore technology.”

That’s what I thought for many years. It just feels very arbitrary, why are horse-drawn carriages better than cars? I don’t know. It’s just a form of technology. But he talks about if you actually learn about their culture, they always evaluate technology. They are very open to it, but they also evaluate the pros and cons against their value system.

Look at cars back in the early 1900s. They try to mount for a while and then they determine that people who are driving cars tended to leave the community, go to neighboring cities, and engage with people outside the community that led to a breakdown in relationships. They just decided like, “This is not coherent with our values, so we are not going to do it.” I think there’s something really powerful to being open to looking at pros and cons and weighing them against value systems and what you are trying to do.

Rob: Yeah and that’s the thing. There are so many fewer absolutes than we would like. They talk about how it’s a sign of intelligence being able to hold two conflicting ideas in your head at once. That’s what both of the things we just talked about are, Twitter and social media conflicting there has a lot of pros and cons.

The same thing with remote work where you can get a little too gung ho in either direction. I think it’s situational and having the willingness to really think it through on a case-by-case basis, to see the realities of it, and know no matter which choice I make, neither is ideal. That’s the hard part is that neither one is ideal. They are going to come with pretty major cons and figuring out how to work around them as best as you can.

As our last topic before we wrap up today, did you read that article, Josh Pigford almost sold Biometrics for $5 million. That was the title, I almost sold Biometrics for $5 million. He published it about six weeks ago.

Derrick: Yeah, I did check it out. It’s a pretty interesting read just because you don’t generally see this level of transparency about something like almost selling your company. It was pretty fascinating to see someone outline their thought process and what was going on through that.

Rob: I know. Super gutsy to do it. I think that’s why because there can be backlash. If you sell it, obviously it goes public that you sold it, but if you don’t sell it and you talk about doing it, there’s danger there. You could have customers leave. You can have employees be upset. Kudos to him for sharing that and sharing his thought process because it sounded tough. A really tough process.

To start with, he kicked it off and he said there’s always a price. Some people get too hung up. A lot of people are, “I’m never selling my business. Why would I sell my business?” I just don’t know. I don’t think that’s the right choice for most people. If you could become independent wealthy, why would you not do this? I don’t hold it against people certainly if you are going to keep your company but don’t just say something out of principle or out of some belief that this is the right thing to do to never sell your company. Think this through.

Now it’s easy. Let’s say I was running a company. It’s doing $50 million a year and I’m pulling $5 million or $10 million a year right off the top, which is totally easy to do with SaaS because it’s so profitable. If you really enjoy what you are doing, then yeah selling your company for $250 million. How much is it actually going to change your lifestyle?

You can afford a jet or whatever, but if you don’t want that and you are doing what you’re doing, why would you do that? But most of us are not in that situation. If you’re running an app doing a million or $5 million a year, somewhere in there, you are not pulling that much money off typically. Typically at that stage, you are in danger of riding it over the top, the growth can die, we can have a recession, you can get killed by a competitor. There’s all these things that could happen and selling a company for a 3X, 4X, or 5X revenue multiple, which Josh was offered 3.75 revenue.

You are doing $2 million a year and you are going to sell your company for $7.5 million, that is absolutely life changing. If you are making $150,000 or $200,000 a year and suddenly you can sell it for that, life-changing in the real sense of the word. It will change your life. You will have options that you never knew you had at that point.

Derrick: A lot of this talk of like why I would want to sell the thing. I’m working on my best idea. I can’t help but think of the Basecamp guys and that was their narrative for a long time. I feel like nowadays there’s a lot more nuance coming from them, which is really refreshing. Jason Fried was at MicroConf, was it last year or the year before?

Rob: Yeah, last year in 2019.

Derrick: Yeah, talking from the stage and he has been one, much more quick to plan the fact that they early on took some money off the table enough, to where him and JJ were millionaires after a couple of years and felt like, “Okay, we’ve made a healthy amount of return of this business. Now we can write it for longer.” A lot of founders go in blind and say, “Why would I want everyone to sell my company,” and yet, what usually ends up happening is that you are not as financially rewarded upfront as you would be if you were taking your raw skill set and having a salary job.

You’re foregoing a lot of money you could be making. A lot of opportunity cost and you are messing that into your equity that you have in your company. If you do end up five years down the line, things are competitive, whatever market conditions, and now suddenly you can’t achieve profitability, you are unable to sell it when you really want to, and you find yourself not able to extract a return from all of the investment that you’ve put into it.

For Basecamp to say, “Why would we want to sell?” because you were able to take some money off the table early on. Then, he also compared now Basecamp to like, “As if I’ve won the lottery and I’m taking the payout over time as opposed to a lump sum.” That totally makes sense.

Rob: Yup. The odds of them going to a business or something is infinitesimal and they get to work. They love their jobs, they have built a great team, and they get to build whatever they want. They’re building Basecamp version three, already built that. Jason Fried was talking a couple of weeks ago on Twitter, like they’re launching two more things this year. They really are a kid in a candy store.

If I were them, I wouldn’t sell, either, but I wouldn’t tell other people. I know they don’t tell other people not to, that’s not something. But I do think that people hear that and then take it upon themselves to think, “Well, I respect Jason Fried and […], I want to be like them, so I’m not going to sell my company either.” I don’t think that’s smart. I think you should evaluate.

Again, if I were Jason Fried, I would not sell Basecamp either because that sounds amazingly fun, but if you’re not in that situation, where you’re tens of millions a year in net profit is what he said, up from the market […], if you’re not in that situation and maybe you don’t enjoy your job, maybe you’re in a really competitive space, and you think that you could flat line.” Once your growth flat lines, your sales multiple plummets. There’s a really good time to sell and if you ride it over the top, suddenly you’re selling for 1X revenue or less. If you’re doubling every year, you’re selling for 4X or 5X revenue, again, it can be a life-changing amount of money or not.

I’m not encouraging people to sell. I think you should do what you want to do, but just really think things through. Back to that whole article we were talking about where Josh basically says, “Hey, there’s always a price. I wasn’t really that open to it,” but he got an offer for $4.95 million and it was like, “Wow, that would change my life.” Then he talks about just how it was a dead end and the buyers had claimed they had the money, but in actual hell, they got him under LOI (letter of intent), they went out and tried to raise money from investors, it was pretty dang shady. It was not cool. That must have been very, very hard.

Derrick: I can only imagine if that had been the case with our Drip story, because I just know how much stress we were under, you especially because you are really bearing the brunt of it, how long the process was, the due diligence stuff, just even getting to LOI. I’m glad that it moves a bit faster, like things didn’t drag out a year, and then Josh discovered this.

I guess on that sense it’s good that it didn’t go on too long, but even for as long as it did, I can only imagine how much you build up all this anticipation. You start to think, “Well, this is looking like it’s going to happen, they seemed very serious about it. Everything I’m hearing from them seems good.” It’s really hard to shift your mind into the gear of like, “I’m about to have a life-changing exit,” and then for that to be torn away is really a mental struggle.

Rob: Yeah. He said, “We’d spent nearly $20,000 on legal fees, months of time gathering all the docs, and they just disappeared. It was crushing. I was and still am furious with them. They wasted an epic amount of our time and money and then crawled into a new hole when they realized they couldn’t do the deal.” Crushing is an understatement, I would have probably crawled into a hole for weeks because your momentum is gone.

It’s one of those really hard decisions to make, but once you make it, you get a sense of peace about it and then that’s all you want. I remember almost hanging on to it too much because you don’t know if the deal is going to go through until it’s all signed. A month before we were selling Drip, it was like, “I’m so ready to sell this company. But I can’t say that out loud, because then if it doesn’t happen, I’ll be crushed.” I definitely feel his pain.

Derrick: Yeah, it’s tough. I don’t know how you could combat that. You have to enter the process, you have to trust what people are telling you initially. You had counsel, you had advisors and stuff, so I wonder how can you avoid that from happening or can you?

Rob: Yeah. I have no idea. I certainly did not and do not believe that I personally could. You would have to be someone of real fortitude to do it. I do like he links over to another article, where he says, “Five things I learned failing to sell my company,” and one of the things he says is avoid needing to sell. This is something a lot of people forget. If you need to sell, if you’re a desperate seller, you will have terms that are not as good.

Always having the abilities to, “Hey, we are growing, we are profitable. I don’t need to sell.” Those three sentiments will get you the best price, that plus getting a lot of different offers. That puts you in the driver’s seat. It’s the same thing with raising funding. Unfortunately, so many people go out to raise funding when they really, really need funding to do anything and nobody wants to fund those companies. They want to fund the companies that don’t need the funding as paradoxical as that sounds.

Derrick: Even on a small scale. When I sold Codetree, this is happening about around the same time that the Drip sale is going through. I was so focused on the Drip stuff that was going on and this was a side app that wasn’t really growing much, but was still just a nice side income for me. I decided it was time to not have to worry about that anymore, but even just having that, going into that with the mindset of like, “I want to sell this thing because it seems like the right time to do that, but I don’t have to,” it could just keep running on the side for a while and no big deal.

Even just going into the negotiation with that attitude. The seller then later on wrote a blog post about how they felt, like they were at a disadvantaged position because they could come in and say, “No, we really want $20,000 off.” My broker was like, “No, we don’t need to do that.” I’m like, “Cool, then tell them no.” Of course, I’m not going to do that, and then ultimately, I think, trying to keep that mindset of like, “If this doesn’t go through, no big deal. I don’t have to do this.” It helps.

Rob: Yeah, having your backs to the walls. Never good, whether you’re selling a car, selling a house. If you’re in a big hurry, you just get the worst deal. Kudos to Josh for that and for sharing. These are helpful things because (again) so many people don’t talk about it when deals fall through like this because it could have negative repercussions, but that’s something that I do love about our community, is that people are often willing to share experiences to help others avoid the mistakes they’ve made.

As we say in the intro, whether it’s to avoid the mistakes or just to understand, if I get into that situation, what will I do? What is this really like? That’s the other thing. If you have not heard of these stories, if you haven’t heard Josh, you haven’t heard you and I talk about selling Drip or any (I’ll say) real startup acquisition, then all you’ve heard is that on TechCrunch, that Instagram sold for $1 billion to Facebook over a weekend, when they had seven people and not much revenue. It’s like, “Well, that’s how startup acquisitions work.” It’s like, “No, they never do. Never.” This is like one in ten years does that.

The real startup acquisitions take a long time, they’re a grind, they’re typically for a revenue multiple or a net profit multiple if you’re running a different type of business or at a smaller revenue scale. There’s just a bunch of pretty common things that are realistic. If you don’t know that and you’ve only read the popular articles about the outliers, your sale is probably not going to be an outlier. So level-setting expectations with this post that Josh wrote is (I think) good.

Derrick: A helpful piece for the community archive for sure.

Rob: Yup, indeed. Thanks, man. Thanks for coming on the show.

Derrick: Yeah. It was a blast, thanks for having me.

Rob: If folks want to keep up with you, you release an episode every week, podcast episode at the Art of Product, you and your co-host Ben Orenstein. That’s a good bootstrap for podcasts over there. Then you are at @derrickreimer on Twitter. We’ll just send people there, but that is what it is.

Derrick: Yeah. Twitter and derrickreimer.com newsletter. Sign-up there.

Rob: That’s probably the one. That’s almost what we should recommend more, derrickreimer.com. I know you’ve blogged a bit over the years. I think all of us probably wish you blogged more.

Derrick: Yeah, it’s always the thing. It’s interesting to think about trying to do more, like higher frequency, less trying to spend 10 hours writing a piece, and think of it a little bit more like Twitter. That could be an interesting thing, too.

Rob: Sounds good, man.

Derrick: Cool. Thanks.

Rob: Thanks again to Derrick for coming on the show. He is working on his new startup. It’s called StaticKit, statickit.com. If you’re working on static sites stuff or interested in that whole ecosystem, he’s building some pretty interesting tools for static site builders.

If you have a question or even a topic for the show, a news item, just something that you think is interesting that you’d like, or a guest take on, you can email it questions@startupsfortherestofus.com, you can attach it as an audio question, or leave us a voice mail at (888) 801-9690.

If you’re not already subscribed to the show (I’m actually surprised), head over to any podcatcher, search for “startups” and we should be in the top three or four. If you want transcripts of these episodes, head for startupsfortherestofus.com.

If you have not yet left us a five star review in your podcatcher, please do so. It would mean a lot to me and it helps the show rank higher, helps us get more listeners, helps me stay motivated to keep producing the show week after week.

We have a theme song, it’s an excerpt from the song called We’re Outta Control by MoOt. We use it under Creative Commons. Thanks for listening to this week’s episode. I’ll see you next time.