Episode 553 | Stack Overflow and Moz Acquired, Quitting Instead of Giving Up Remote Work, and More Bootstrapper News

Rob: Welcome back to Startups for the Rest of Us. I’m your host, Rob Walling. Every week on this show we cover topics related to building and growing ambitious yet sane startups. We look at building companies, not as a vanity project, a way to get power and status in the world. But we think about it as a way to improve our lives to bring us freedom and purpose and allow us to maintain healthy relationships.

It’s not about being a total bootstrapper, it’s not about raising buckets of venture funding. It’s about being capital efficient and building a company that serves perhaps multiple purposes, rather than just being an IPO in 10 years, but that actually changes our lives and those around us.

Welcome back to the show. Thank you so much for joining me again today. We’re going to be covering bootstrapper news today with Tracy Osborn. I’m excited to talk about it. We have some pretty interesting stories, actually. Stack Overflow was acquired for $1.8 billion. It came as a total surprise to me. Just a few minutes prior to recording this, Moz was acquired. We talked about people quitting instead of giving up remote work. We wrap up the episode by talking about remote work and remote retreats, and if you are a remote team, how often you think about getting together.

We also talk about a few highlights from our 2020 batch of founders and talk about what we feel went well with that. That dovetails into the whole remote conversation of not being able to get together for retreats during this batch here, and how we feel that impacted us and perhaps the cohesion of the batch itself.

Today, I’m talking about these topics with Tracy Osborn. She’s @tracymakes on Twitter. Of course, she is the Managing Director of TinySeed and the author of Hello Web Design. Within the first few minutes of us chatting, you’ll get to see that book hot off the presses. She self-published it and then later went through a publisher and has a nice hardcover copy. So with that, let’s dive into today’s show. Tracy Osborn, thanks for joining me.

Tracy: Yeah, happy to be back.

Rob: Last time you were on you were talking about your book, Hello Web Design. Before that, we did a bootstrapper news episode. You’re getting the book out. Is that a physical hard copy, hardcover of your book?

Tracy: Yeah, it is a hardcover. The publishing company wanted to up the quality of it. Apologies to anyone who’s listening to the audio format. Just imagine a book that’s hardcover. It used to be a paperback. It looks really nice now. Gosh, I don’t know the exact date it’s coming out, but it’s going to be this month. I know some people have already gotten their book.

Rob: That’s cool.

Tracy: Listen to the last episode where I talked about my design book. You’ll get the link to buy my book that teaches web design. Sorry, I have to put a pitch in there. This is the perfect opportunity.

Rob: Nostarchpress.com/hello-web-design. Before that, you and Einar Vollset were on the show to talk about bootstrapper news. We’ve had all kinds of conversations around this. Einar is out of the office today. He’s taking a day off, and so it winds up being you and I here recording. Thanks for doing it last minute. I found myself at the end of the week saying, I have no episode next week. So it’s great.

Tracy: I like how you just admitted that. I wasn’t going to say anything. But, yes, I’m very happy to be the person you go to when you are in a pinch.

Rob: Scrambling. That was a thing. It doesn’t happen very often. I mean, I often record at least a couple of weeks ahead or I get stuff done Tuesday, Wednesday for the following week. But, I don’t know, this week there was a lot going on and a lot of email. But we are really talking through news and other topics. We even have a listener question I might throw in depending on how time works out. This is stuff that’s related to developers, designers, founders, bootstrappers, and such—the folks who would listen to this podcast.

The first story, what’s funny is I hadn’t heard about it. It wasn’t until I was digging through a bunch of social news sites for news over the past couple of weeks that I read that Stack Overflow sold to a tech giant that I’ve never heard of called Prosus for $1.8 billion. It says that it’s Prosus’s biggest investment in online learning and comes weeks after it’s sold a chunk from its massive Tencent holding.

Stack Overflow, this site. I listened to Joel and Jeff when they were launching Stack Overflow. They had a podcast around it. I’m an early account, I don’t think I ever answered a question. This is like a mainstay for our communities. What’s your take on this?

Tracy: I haven’t answered a question ever either. I’ve gotten so much out of Stack Overflow, whatever I’m programming. Like any programmer I’m using it on the minute, every minute, it seems like when I’m trying to debug something. This is interesting to me. I mean, one of the reasons why I work at TinySeed is that I’m a big fan of smaller companies. I try to enable a lot of people on the internet to launch small things, and I love small teams. This goes into real life for me. I do small businesses, not big conglomerates and whatnot.

It’s been interesting to see the trends we have in (I want to say) the physical world of consolidation, of businesses like news industries. Seeing that move into online industries, and you can see that here with Prosus, which I had never heard of either. For being such a tech giant—I guess it’s South African—I’ve never heard of them.

When I was researching a little bit for this story, looking at all the different acquisitions and properties they have, they’re all around online learning. It looks like they have this plan to go through all these online learning websites, supposedly, keeping them independent and they’re still running on their own, but they’re still consolidating all these online learning websites.

It leads me to wonder about what it’s going to look like in five or so years as these companies are getting acquired and consolidated. Are we going to have these mega-corporations that are pushing for a certain way of learning when it comes to online learning. Pushing for certain ways of learning or being more (I want to say) anti-democratic. You know what I mean when a big company comes in and takes over these small companies, and then all of a sudden, they all start looking the same. They all kind of had the same processes and whatnot.

On one hand, it’s more efficient, on the other hand, I mourn for the freedom of these small businesses. I might be going way too broad here, but it made me think about news corporations and consolidation there, and seeing this happen in the tech world. I told you earlier, I kind of miss the ‘90s, where it seemed like everyone was just individuals running websites. And now we have these mega-corporations that are running things that I use actively. It makes me wonder how it’s going to look in the short future.

Rob: I wonder if you’re the only person that misses the ‘90s because, man, the fashion was terrible/ I guess the music was pretty good, but no, I’m joking. Very fond memories of the ‘90s.

Tracy: Frame websites. We’d have friends and development nonsense. I just built it with frames.

Rob: Yeah.

Tracy: Sorry, go ahead.

Rob: The thing is with any industry, there’s always a bunch of players and the consolidation has been inevitable. Where it’s like there were a hundred car manufacturers in the US, and now there are three. There were a hundred airplane manufacturers, and now there are a handful around the world. There were a bazillion TV stations, and then it became just three, maybe that one’s not true. But radio? Each of these things has consolidated. TV is the one where it got distribution, cable, and it actually expanded. But then there’s only a handful of companies now that own them.

There’s NBC, CBS, and AMC, or whatever, but they’re only owned by a handful of companies. I hear you on wanting the days back where it’s small players. Again, Joel Spolsky started a little software company called Fog Creek Software in 1999 or 2000, started blogging, and then start Stack Overflow. He was the CEO until 2019, I found out, and then he became the chairman. At that point, when one of the founders steps away from being CEO, I feel like the clock is ticking for an exit.

This type of thing where they did raise venture funding, I think, a lot of us were surprised because Joel was one of the few bootstrappers. He was the first person I’d ever heard who started a software company without raising venture funding. As shocking as that sounds today, in 2001 I was like, you can do that? That’s a thing? I literally didn’t know that was possible. Just every model I had seen was someone raising funding.

When they raised for Stack Overflow, I remember being super surprised and Joel was like, look, certain types of businesses, if you want to do some certain types of outcomes, you need buckets of money. To do Stack Overflow the way they wanted to do it with all the stack exchanges and all the stuff, that was what they wanted to do. Once you raise that level of money that they did—through venture, not TinySeed money, not angel money—the clock starts ticking. You have to have a liquidity event. So they needed to IPO or they needed to sell at a certain point.

I look at it as I think it’s cool for Joel, Jeff Atwood, and the founders (whoever had equity in this) that they built something amazing and that they now walk away with boatloads of money to be able to invest in and fund future entrepreneurs. Of course, I’m concerned about Stack Overflow itself. I don’t use it at all anymore unless I’m helping my son troubleshoot a 3D printer driver or something. I don’t know if Prosus is private equity, or venture equity, or what they are exactly. I guess I could have actually done some research. But basically, they’re some type of big conglomerate investment that’s rolling things up.

But I’m excited about the opportunities. There’s always the opportunity for scrappy entrepreneurs to come in. If Stack Overflow is not going to be good, should we all start a new Stack Overflow that would be a competitor? That would be crazy. You wouldn’t have done that while Joel was running it because they would win. I guess there’s just a lot more money in the startup ecosystem with Jeff Atwood, Joel, and the other founders having this money to reinvest.

Backing startups, I think that’s something that they will do. They will do interesting things with the money. They’re not going to go retire on a beach somewhere. They’re going to start their next company or they’re going to help other entrepreneurs. But I’m a silver lining person when it comes to this stuff because there’s definitely (as you’re saying) both sides of it. There’s a real negative take I think that is very real. It’s a real possibility.

Tracy: Yeah, I just looked it up actually. Prosus has stakes in companies. It still has a stake in Tencent. But they also have other education companies like Brainly, Codecademy, Udemy, Remitly, PayU—some things I haven’t heard of and some things I have. It gives you an idea in terms of their ecosystem there.

When I say something about consolidation and mourning it, when I think about radio stations, you see the radio stations consolidating to get more plans, boring, and vanilla because there are no local radio stations. It’s harder, I think, for individuals for radio to start up their own thing.

But with tech, that’s the thing that makes me optimistic about what we can do on the internet. What we can do as tech entrepreneurs is that if Stack Overflow does go in a direction that people don’t want, then it’s easier to start something new and pull out those features, pull out anything that doesn’t work anymore—Stack Overflow, as they make changes. If they make changes and that the internet evolved pretty quickly to fill in that gap as compared to say some of these more (say) physical businesses.

That brings me a little bit of comfort. Obviously, I don’t want Stack Overflow to change. I mean, I’ve never given back, which is not necessarily a good thing. But I appreciate all the people out there who have spent the time and unpaid work to answer people’s questions. I hope that that kind of community sticks around post-acquisition.

Rob: That’s a good point because starting a new car company today would be very, very difficult. As we’ve seen with Elon Musk on Tesla—even with all the money, all the influence, and network he had—it’s been a real uphill battle for him. Versus starting a competitor Stack Overflow, the network effect will be really hard, like you said, the marketplace aspect of it. But way more possible than starting a car company. It’s interesting. We have another story we need to cover in-depth, but literally 33 minutes ago, the story broke that Moz was acquired by iContact.

I got a text from Einar and I’m like, wow. You know it’s gonna happen, but I’m always surprised when it does. And really, why should I be surprised? Again, it’s a venture-backed business that was doing, I think, $70 million a year last year, it’s SaaS App, it’s worth a lot of money. The founder left a few years ago to start SparkToro. It’s probably natural that the new CEO they brought in was to groom it and get in line for an exit.

We don’t have any details about price, outcome, or anything, but this is another thing. I think this is the critique of venture capitalists is that they don’t build businesses for the long-term because there does have to be this liquidity event, usually a sale. But what’s interesting is I’ve realized over the past couple of years, an IPO obviously is also a liquidity event, and an IPO is just really just raising funding from the public. Do you know what I mean?

A lot of people will say like, oh, they IPO and they sold out, or they sold everything. And it’s like, no, they just sold another 10% or 20% just like a funding round. Oftentimes, the founders or the current CEO will stick around for that.

Tracy: I didn’t get that for a long time either. IPOs felt like this big—I mean it is still a giant event and whatnot. But still, like you said, it’s the same thing. Taking a bit of your company, instead of going to private investors and going public.

In the Moz thing, I am looking forward to seeing what news comes out of this. I hopefully will hear from Rand soon. I hope that it worked out well for him. But iContact is another company where it’s like, oh, they’re acquiring Moz to form a suite of leading SEO, email, and digital marketing solutions for small- and mid-sized businesses. It’s another example of this consolidation. A bigger company being like, okay, we need another company in our portfolio, so we have this full portfolio, this full ecosystem of different tools. I guess we’ll just see what happens with Moz too.

Rob: Yeah, and that’s it. The plus of this is hopefully Rand, whoever else had equity, and the investors walk away with enough money that they now are reinvested back in the ecosystem. I mean, Rand himself, even before this exit, is an investor in TinySeed. He’s a mentor. He’s giving back to the entrepreneurial community in ways that his means have allowed, and if Rand has more means he will, I think, give back more. That’s the plus side of this.

And of course, the negative side is if you’re a Moz customer, things are going to change. They’re pretty likely to. That’s where it’s good that we do have competitors—Semrush, Ahrefs. There are other tools out there that do similar things. It’s just a bummer if you’ve been using a tool for 10 years, it gets sold, you’re waiting for the inevitable changes. The playbook, as you said earlier. These things, they start to be run the same. It’s the playbook. The private equity or the strategic playbook.

Tracy: Got to bring the people in to make sure everything is efficient, that efficiency is reflected across every one of their properties, and then everything looks the same.

Rob: Yep. Don’t do this, but if you read The Hacker News comments for any of this or even just the comments on anything, you’re going to see things like the founders sold out. You hear this phrase. It’s almost like, no one should ever sell their company. And you know what, that’s just not realistic because people don’t want to run the same company for 40 years, (a) it gets boring, (b) there’s a lot of risks.

You can have tens of millions of dollars in net worth tied up in an asset that you have no liquidity. So it just doesn’t make sense. It’s usually said by someone who’s never built a company worth tens of millions of dollars a year who is saying these things. Of course, do you think sometimes it gets worse after a company is sold? Of course. But there’s a flipside. Are there silver linings to this as well?

Tracy: Yeah. I mean, the service is more stable because there’s more tech support within the company, more A-team, or more personnel. Are they able to add more features quickly? The consolidation with other parts of the suite. I think of Microsoft. Microsoft has a whole suite of applications. A lot of these applications, they’ll talk to each other, so there’s a lot of benefits there as well when you opt in to some of these conglomerates.

Rob: Yeah. It is still disconcerting though, I’ll admit.

Tracy: Right.

Rob: Next story. We’re going to link up all these stories. This is on bloomberg.com and it says, “Employees are quitting instead of giving up working from home. The drive to get people back into offices is clashing with workers who’ve embraced remote work as the new normal.” And it talks about someone who is called into the office for a six-minute in-person meeting or something, and she’s like, that’s it. I’m quitting.

My brother lives in the Bay Area, most of my family is actually. He said that he is friends with some folks who work at Apple, and they lived near him. When the remote work started, they moved like a two-hour drive away because the houses are so much cheaper, and you can get a view on all this stuff. Maybe it was even two and a half hours.

He’s like, they think they’re going to be remote forever and I think they’re not. I don’t think Apple’s going remote with the big flying saucer campus there. What are they going to do when they come back or when that happens? We were chatting about that, and I said, boy, if they’re developers or they have skills, they can just work remote for someone else, probably. What’s your take on this?

Tracy: I mean, ignoring COVID, this is just what happened with Yahoo because they had a remote policy, Marissa Mayer came in, and then it was like, oh, we’re canceling the remote policy. Everyone has to come back into the office because there’s still this pervasive idea, that productivity is tied to butts-in-seats. I was like, oh look, we’re taking this company, or we’re making it more productive in bringing people to the office. We’re going to have all those “benefits” of having butts-in-seats. That was pre-COVID.

Yahoo is its own thing. Who knows what’s going on with Yahoo now. But I remember that happening in the Bay Area, and COVD happened. That forced all these companies to adopt a remote policy. It’s the same thing, COVID’s lessening, the pandemic is lessening. It’s allowing people to get fully vaccinated, have the possibility of people going back to the office.

Company is ill-advised, the pursuit of efficiency and managers who have maybe not a lot of confidence in their teams or they are insecure managers (I want to say) going to pursue bringing people back in the office so that they can not have that question over their head of are my workers being as efficient as possible?

So it’s not something I agree with. We’ve always been 100% remote. I love working remote. I just look at Yahoo, I look at what’s going on right now, and this is like duh. Watching these companies force people to come back to the office, people are going to quit because now they realize there are more opportunities out there.

I expected the companies to do this. What is different now is that so many companies are going to be adopting more remote work than these companies that have, say, insecure managers, and insecure C-suite teams that want to move people into the office, now, they have more competition. Now their workforce is aware of remote work.

I watch the industry, people are going to be trying to adopt these policies. People are going to be quitting. Other opportunities are going to show up that are fully remote. Again, five or so years from now, there is going to be a major shift in the industry that started now because of COVID.

I’m not surprised but I expect that this is going to be, hopefully, a long-term change. These companies that have insecurities around productivity, I expect them to have this reaction, but hopefully, they’ll change.

Rob: It’s interesting because I’m much less black and white on remote being the end all be all. Every company I’ve ever run has been remote or half remote. In Fresno, we were partially.

Tracy: Yeah, I didn’t mention that. I’m not black and white either, and I didn’t really go into that. I actually think, TinySeed, I wish we were half remote. I would love to work with you two days out of the week.

Rob: Yep. That’s my ideal.

Tracy: I think that is the ideal for these companies as well. I think the black and white thing is like whether fully remote versus fully in the office. There’s a lot of gray there. Sorry, continue.

Rob: That’s the tough part is every time I talk about remote, I talk about the best setup I ever had and it was in Fresno. There were five of us or six of us—I forget how many were in. It was two and a half days a week for me. Some people showed up three. I think Einar worked there five days a week in the office because she liked it better. She was alone half the time anyway because none of us were there, but we were able to whiteboard.

Our staff meeting was lunch, and we’d go out on Thursday. I mean, that was the best. And then I could go home, put the headphones on, and not worry about having to drive in those days. It’s really hard to do that. Not for Apple, I guess. It’s hard to do that if you’re a small company or a bootstrapper because if you’re going to pay for an office anyway, that’s a cost if you’re only using it half the time.

In addition, then it does restrict you to I can only hire within a 30–45 minute drive. You live in Canada, Einar’s in California, I’m in Minneapolis, Producer Xander with MicroConf is in Hawaii. If I had to hire everyone in Minneapolis, we wouldn’t have the team we have. It instantly breaks that. I really struggle with it.

Tracy: It’s the same thing if you were like okay, TinySeed, COVID is over. We’re going to pursue being in person in Minneapolis. I would have to quit. It was like the same thing. I don’t want to, but I have to because I’m here. I feel like that’s going to happen a lot to these companies where, like you said, the example of someone who moved out of the Bay Area—two hours out so they have a lower cost of living—is going to be very unwilling to come back into that high cost of living area. That’s maybe where this change is going to happen. There are companies that can make this work.

My first job out of university was at a tech company. That’s my example of an insecure manager. Over the four and a half years I was there, they kept adding more and more policies that make us more efficient. So (a) we were all in the office, (b) we started clocking in and clocking out, (c) bonuses were tied to us working nine hours a day, rather than eight. If you only work eight hours a day, you’re not eligible for any bonuses. These policies kept adding up, adding up because they’re like, we wanted to extract all the productivity. Curious how they’re doing now with COVID. I eventually quit because of that.

Rob: Absolutely. Hours do not equal productivity. That’s the thing is my kind of shades of grey, or my spectrum view of this is not because I think, oh, I’m going to get more productivity out of people, or I can make sure they’re in their seats those two or three days a week. It is purely for social interaction. A lot of the companies that say, we’re fully remote—Basecamp’s a typical example, they’re all remote. From what I’ve heard, they hired a bunch of introverts, and everyone in the world is not an introvert. The extroverts I know don’t love working out.

I have worked remote for 20 years, literally two decades of working remote. I had a couple of stints in there where I had jobs for a year or two. But in general, I’ve had a home office. Sometimes that was a desk in my living room when we had a small house, or in my bedroom during COVID when I didn’t have room. I generally prefer remote, but I also miss a lot of the social. It purely is social and the ability to sit in front of a whiteboard or to hash things out. It’s that water cooler conversation that just doesn’t happen because you’re not hanging out all day.

You just have other wild thoughts that you drop on someone and that spark something, then there’s a brainstorm, and then there’s a hey, can you… That’s what I miss rather than being a hardcore manager.

I think of Apple with thousands of people, that would be tough for me. There have to be people that are just totally abusing it at that scale. On our scale, there’s four of us, or at the Drip-scale there were 10 of us. That was pretty easy for me to see who was shipping, what we were getting done, and to know that everybody was in on it. But if we were a hundred or a thousand…

I mean, I’ll say, once we were exorbitant to Leadpages, which is about 180 people total, it was three days in the office, two days work from home. There were absolutely people that were slacking off. That’s tough. I don’t know how to handle that, other than to require people to be in the office.

Tracy: Yeah. I mean, that happens if you’re in the office all the time too.

Rob: Yeah, that’s true.

Tracy: I mean, not to defend myself, but I got really irritated by that one company constantly tracking hours. One other thing they did was I wasn’t allowed to have my phone out because then I could potentially be looking at my email during work hours. It’s just crazy. I wish I could name and shame them, but I’m not going to.

Rob: I know, I can’t even… this is crazy.

Tracy: I’ll tell you stories later. What I did, I just stared at the corner. I would just take breaks, stare at the corner of the wall, and let myself drift off because there was no way they could stop me because I was just so mad at their policies. That’s going off track, but it’s a funny story.

What I want to say is that it still happens. There are still going to be workers out there that are maybe not performing as well as they could have. Maybe they’re a worker that the company might want to hire a person to replace that person. I don’t like tying everything to productivity, but you know what I mean. The person is not necessarily a good fit for the company.

That doesn’t matter whether they’re remote or all in-person. What it means is that companies need to have better ways of tracking the quality of work. Instead of just being hours in the office, like that company that I originally worked at. We were doing all we could, the person’s here all the time, this is as efficient as we could be. Look at other metrics and then those metrics can apply to whether someone is in the office or out of the office.

Hopefully this forces these companies to remove butts-in-seats and find other ways of tracking quality of work, productivity, and whatnot. If those things apply to in-person or out of person, I think that overall, it’s going to be better for the company anyway.

Rob: I love that you just said in-person or out of person. That makes me feel like I’m leaving my body. I’m floating guys, I’m seeing myself.

Tracy: Oh, gosh. That’s what my brain does. I’m thinking two sentences ahead and forgetting what I’m currently talking about.

Rob: It’s all good. Our next story is a Twitter thread I’m going to be posting next week. Maybe I’ll post it the day before the day that this episode goes live. It is about TinySeed and the end of our second batch, which is our 2020 batch. I want to be careful. Audience, listener who’s sitting here listening, this is not going to be a big hooray for us or hooray for TinySeed, but I did want to visit some milestones that some batch two folks achieved. As well as reflect on things that we did well and some things that maybe we need to work on. As well as just the structure.

Someone asked me in the last couple of weeks how do you run a fully remote accelerator, and why were you running a remote accelerator before anyone else? Because we were running that pre-COVID. Now, all accelerators have been remote for the last year. We orchestrated and architected this to work that way.

Tracy: Actually, this ties into our previous conversation. We were talking about tracking performance and quality and not necessarily being butts-in-seats. For us, some context around this is that, before the first batch, we were able to talk to the founders and the accelerator in person at MicroConf. We’re able to say, how was this year for you? And kind of get the down low. Of course, fully remote we weren’t able to do that.

We have anonymous surveys because we want to know how well the accelerator is doing, which is especially important being that most of the people—actually, I’ve met a few people in batch two, our 2020 batch of MicroConf—I’ve never met in person. This is the only way we have a gut feel for how the year went, but how does this look from the founder’s side of things? How well did this year ago, being that we had no in-person events and we had to do everything remotely?

Rob: That’s right. Because if you think that hiring someone remote is difficult, imagine running someone a $120,000 or $180,000 check remote having never met them and only being able to talk to them via Zoom and email.

A couple of numbers. Our first batch, our 2019 batch was 10 founders. 2020 batch, that just ended was 13. And our spring 2021 batch is 18. But the 13 companies in our 2020 batch grew an average of 413% during the accelerator year. While fundraising is not an implied goal of TinySeed, we had—I guess there’s one company who secured their pre-seed round and two others who are basically about to wrap it up.

We had our first acquisition, which was SeekWell. The founder of SeekWell was on this very podcast probably about six months ago. ThoughSpot acquired them. We had some great milestones.

ScrapingBee is great because they are very public with their revenues. We can actually say exactly, not just percentage stuff, but Scrapingbee was at $40,000 ARR when they applied. I don’t know if it’s when they applied or the batch started, but now, they’re at north of $500,000 ARR. The founders there told us that TinySeed played a huge part in that.

And then SegMetrics. Many of you know Keith Perhac, he’s a long-time MicroConf-er and has been on this podcast. SegMetrics grew 10 times in the last 12 months and they’re on track to hit mid-seven figures ARR by the end of this year.

A lot of cool milestones. Pretty stoked about it. It was a big bummer that we couldn’t meet a person. It’s not a regret because you can’t do anything else, but the fact that we weren’t, as you said, able to make that connection I think was a pretty big struggle.

Tracy: We always knew it was going to be remote. We wanted to help companies and these founders grow their businesses, help them reach (what you say) escape velocity, which I think some of those stats we were successful in helping those companies reach those milestones. But a huge thing is also just community between founders, especially for solo founders. We talked to a lot of our solo founders. It gives them a sounding board, people to talk to. And all these things that we can do remotely fairly well, but there’s something about getting in-person and having this group of people all together in-person.

I mean, it’s the same thing as a company. Working remotely is fine with you, me, Xander, and Einar, but it’s a different feel when you do have those like in-person meetings, in-person events, and whatnot. It’s a bummer that we weren’t. We were able to have a lot of community. There’s a difference in feeling between the 2019 and 2020 batches. I think it has to do with the fact that there weren’t any in-person events. Hopefully, as things open up this fall, we are planning to have some sort of in-person event like a makeup retreat for the 2020 batch. Hopefully to add that into the end and solidify all those relationships we were able to do remotely.

I will say that I do feel like there was a different feel, and it was interesting to have that experience I guess. I think when we did that anonymous survey, thankfully it seems like people still got a lot of the program without those in-person events. I am looking forward to bringing them back in though and re-establishing that side of TinySeed.

Rob: It’s a big deal. It makes a huge difference. I think when we originally started TinySeed we said, let’s have four in-person retreats per year. That means that every four months you essentially get together. The founders told us, this is too often. I’m busy and I don’t want to travel every four months. So then we made it six months apart, which means you have three retreats.

Tracy: Beginning of the program, end of the program, and middle of the program, to be clear.

Rob: Yep. Every six months. We haven’t had a chance to do that yet, but I feel like that’s going to be perhaps our optimum cadence. And the reason I’m calling this out is let’s say we were a team of 20 people, would six months be the optimum cadence? Or would we want to meet more frequently like every three or four months? Because I know that there are certain companies that only have one—I think Zapier has like one retreat a year. There’s a lot of people working there. They spent a quarter-million dollars or more to get them together. It’s not something they could probably want to do every quarter.

But what do you think would be the optimal? Because working with founders is one thing. They’re busy, they’re doing their thing, we get together, and we mastermind. But we are not managing them as teammates, as employees versus an actual team that’s working together in a startup. What’s your take on optimum cadence, face-to-face?

Tracy: One of the reasons why it went from four to three was because we talked to the founders in the first batch, four retreats per year meant more time away with their family, more time away from their company. It’s different when it comes to say a team because maybe four retreats per year or whatever you choose, it’s not technically time away from your company. You’re still working on your company while you’re at those retreats. That’s the biggest difference between retreats for founders who work in a company versus a TinySeed if TinySeed was 80 people.

I think it’s really important for companies to have those in-person experiences, and those are the kind of things that don’t necessarily take away from work. Instead of working on the nitty-gritty day-to-day, it gives you that time you should be doing as a company anyway to think high-level, what’s the next three, six, whatnot months? That’s something that depends on the company and how remote they are. If you are very international, every three months would suck. Every year I think is doable.

Rob: If you’re going to get your team together, we’re talking about founder stuff, but if you have a team at a start-up and you’re going to get them together, I found a really nice cadence is to have about half the time be work and half the time be not. It’s even like 2/3 not work where you have a work session in the morning maybe through lunch or early afternoon, then you have an afternoon fun hang-out, and then you have a fun dinner hang-out.

Usually, if you can, have a fun dinner hang out the night before because everyone gets in and it’s like, oh man, I haven’t seen you in a while. You’re a lot taller than I thought you’d be. You have all that weird stuff and you’re chatting. And then by the time you get to the work session the next morning, you have some type of agenda.

We do masterminds but that wouldn’t make sense if you’re a team of 5, 10, 50 people. But you do have an agenda of these are the things we’re going to hammer through, and then there is space for other things to crop up. Then again, after you leave that in the early afternoon, usually that’s then a bunch of time to continue that conversation and let it go wherever. That’s where it goes naturally. That’s the best part.

Tracy: The spontaneity, the little things that you don’t expect.

Rob: Tracy Osborn, thank you so much for joining me today. You are @tracymakes on Twitter and tracyosborn.com if folks want to keep up with what you’re up to.

Tracy: Yeah, and if you are looking to pick up some design skills, I have a beginner design book that is being published through No Starch called Hello Web Design. If you google for that, you’ll probably find it on the internet. It’s a republished book. I originally self-published it, it was successful. I was able to sell it to a publisher. That’s how you know there’s a stamp of approval, it is good work. If you’re looking to add design skills on top of your current stock, check out my book.

Rob: Awesome. Thanks again for joining me.

Tracy: Thank you, nice being here.

Rob: Thanks again for joining me today. I got a five star review. “One of the best podcasts for SaaS founders.” It’s from onlyoneda. “Thank you, Rob. Loving the podcast. It’s motivating me to keep going.” We have 906 worldwide ratings, 397 worldwide reviews across 47 countries. If you haven’t left us a rating, that would be awesome. I’m on a drive to get to a thousand. I want four figures of five star reviews.

I really appreciate you listening all these years every week since 2010. We’ve been talking about mostly bootstrapping, building ambitious yet capital efficient companies that change our lives. I hope you join me again next Tuesday morning.