Episode 569 | The Life Changing Decision of When to Sell Your Company

Rob: Welcome back to Startups for the Rest of Us. I’m your host, Rob Walling. This week, I had a conversation with a founder who’s been in the MicroConf community for several years. She actually attended her first MicroConf in 2019 on one of our scholarships, and by that time, she had been building a SaaS business. It’s a two-sided marketplace with a subscription component, and it’s for RVers.

She’d been building that business with her mom for seven years by then, received an offer to sell it—it was a so-so offer—she had come to the conclusion she was going to sell it, came to MicroConf, and got advice that literally changed the course of her and her mother’s life. It’s a great story of an entrepreneur who persevered for (really) nine years before selling her business, and changed the course of her and her mother’s life in the process.

This is entrepreneurship. This is why we talk about this every week on Startups for the Rest of Us. This show is for ambitious startup founders who want freedom, purpose, relationships, and want to change the course of their life through starting their own companies. With that, let’s dive into our conversation.

Anna Maste, welcome to Startups for the Rest of Us.

Anna: Thanks so much for having me, Rob.

Rob: Absolutely. Today, we’re going to be talking about Boondockers Welcome. It’s at boondockerswelcome.com, how you and your mom started it, grew it over the course of nine years, and then sold it for a life-changing amount of money.

I want to start with two questions. The first is, what is a boondocker?

Anna: In the RVing world, a boondocker is usually somebody who camps without hookups—camping in the boondocks, in the boonies—but more often than not, it actually ends up being in somebody’s driveway, or in a Walmart parking lot, or a much less glamorous than actually in the back country boonies. That is boondocker means in the RV industry.

Rob: And it’s a long domain name, and really would only be known by someone in the space because I had seen you in MicroConf Connect, I’d seen the URL, and I never had any idea what it did because I hadn’t visited the site until you and I have really connected deeper. Would you feel that was a benefit that is so niche-specific? It’s like saying build my MRR, everyone in SaaS says that is, and no one outside knows that?

Anna: I wouldn’t say that the term ‘boondocker’ had a great amount of benefit to us in that respect. On the list of things I would change, maybe a shorter domain name would have been at the top of the list, but we definitely did manage to build a brand, and to most RVers they would’ve known what a boondocker was. It became synonymous with staying on people’s properties, so that was pretty cool.

Rob: You and your mom sold Boondockers Welcome earlier this year. As you emailed me and you and I chatted definitely, I think the exact phrase you used in the email was, “It was in the space of the ‘we be crazy to say no’ variety in terms of the multiple.” Do you remember the moment when the deal closed and you were looking at it? Did you look at the bank account? Were you refreshing like I was the day we sold Drip? What was that like for you?

Anna: Actually, the funny story is that the money got lost for a couple of days.

Rob: Oh my gosh.

Anna: It was a couple of days where my lawyer was on the phone because it was going into her trust account, so she was actually on the phone with the bank trying to figure out where the money was. It was a bit of a kerfuffle, so our close actually got pushed out by a couple of days because of that. When the money finally did show up in the account, there was a combination of relief with just shock and happiness, but relief that money had not just disappeared.

Rob: That’s terrible because I remember how stressful any type of acquisition is, really from either side but more from selling, in my experience, and I cannot imagine not knowing where the money was.

Anna: Yeah. I think that some lucky person actually opened up their bank account, saw the money in there, honestly came back to their bank and said, this is not my money, and that’s how we found it.

Rob: Wow, that’s terrible.

Anna: Nobody’s fault. I’m sure there’s just a number, a digit got switched or something somewhere in there.

Rob: That’s unusual. I haven’t heard that before happening with an acquisition of a large sum of money getting set to the wrong account, in essence.

There’s a big chunk of stuff I want to cover around how MicroConf played a role, and how the MicroConf scholarship program played a role in shifting some of your thinking in 2019 that made this all possible. I want to roll back for now and start at the beginning of you starting Boondockers Welcome with your co-founder, your semi-retired mom (who is a former waitress). She had become an RVer, built herself a bit of an audience, and a name in the RV space, having written a couple of ebooks for RVers.

Talk to me about how that unfolds. I haven’t personally started a business with my relatives, much less my mother, so I’m curious. Was this an idea that came from her? Did you bring the idea to her? How did all that get started?

Anna: I was actually on maternity leave with my eldest son. My mother approached me. She had, like you said, these successful travel guides, had a bit of an audience, and she had this idea for what she called sort of a driveway surfing community, like couch surfing but for RVers.

Apparently, it’s quite common in the RVing industry for people to say, oh you should just come park at my place anytime you’re in town. RVers are really easy guests. They bring their own bathroom, they bring their own bed sheets, you don’t have to worry about what your house looks like. She said, I’m thinking about building this. I was going to see if I could contract somebody to develop it for me. Would you help me find someone?

I kind of stepped back and said, whoa, whoa, whoa, mom. Have you vetted this idea? Do you really know it’s going to cost you tens of thousands of dollars to get somebody to build this? I was on maternity leave. I didn’t really have a lot. We live in Canada where we have 12 months of paid maternity leave. I’m not incredibly well-paid but better than nothing paid.

I was happy to take some time. She came and spent time with her new grandson and I started working on developing the website. Web development wasn’t my background. I was a firmware engineer, so there was a big learning curve for me there just to switch gears, but that’s how it all started as a bit of a side project.

We developed it slowly. It wasn’t until my second child was born that we actually ended up launching it. That was the impetus.

Rob: I’m curious. As a firmware engineer building maybe one of your first web apps in 2012, what tech stack did you use?

Anna: I ended up using just a Drupal CMS with a bunch of modules and a little bit of custom PHP code stuck in there. I had some familiarity with PHP and it’s a pretty flexible CMS in general, so I was able to wedge in the payments and the pieces that we needed to make it work. That’s what we started with.

Rob: In retrospect, did you think that was a good decision?

Anna: It was probably a good decision in the minimum viable product sense. It didn’t require a whole lot of custom work to be done. It certainly did not give me the flexibility that I needed to really develop the platform to something larger. It took a long time, so I wouldn’t call it a minimum viable product in that sense, but on the side it was a minimum viable product in the sense that it did what it needed to do to see if it was an idea that was going to fly.

Rob: That’s (I think) the important point because I “built apps.” This is before no-code. These days I would probably use no-code for something like this, but I built them on Drupal and WordPress. Usually, it’s to get something out really quick, and then if it actually works, got to rewrite it. There’s no way I’m going to deal with the constraints and confines of an ecosystem like that.

You launched in 2012. Was it hockey stick rocket ship growth? What did you experience?

Anna: Oh goodness now. I remember we launched to my mother’s newsletter list. She had several hundred people who had bought her guides, and those first people seeded our host space. They were our first 200 hosts. They signed up quite readily at that point. It was lifetime free if you sign up as an initial host.

We’re talking about essentially a two-sided marketplace. The difficulty of building a two-sided marketplace is well-known and talked about often on the show, so I’m sure that most of our listeners are going, oh gosh, how did she ever make this work. That was the thing. But yes, we had the advantage of having a really decent seed list.

We got our first couple of hundred hosts in those first few months, and then we turned on the ‘okay, from now on if you want to join, you have to pay’ switch. I remember kind of sitting there waiting to see if anybody would buy. Within a week we had one person, and it was kind of like one person every week for a little while. It was very slow.

Rob: How did the pricing work at that point and what was the model? Is it a subscription model or a one-time fee? Were you charging the hosts or that RVers? Am I using the right terms there? The hosts or the boondockers?

Anna: Yeah. At that time, our assumption was that anybody who wanted to be a host was probably an RVer as well and would also want to be a guest. We did after those initial 200 free lifetime members. We turned on pricing for everybody. You got a discount if you signed up as a host, but we just assumed that everybody wanted to be a guest, so it’s going to cost you (I think it was) $25 a year. That’s subscription but not even an automatically renewing subscription. There was lots of low hanging fruit there but $25 a year, $20 a year if you were a host.

Rob: That’s crazy low. I marvel at everything you’ve done. Everything I’m about to say you already heard me say in the past. Building a two-sided marketplace is really hard. Don’t do lifetime grandfathering. The first 200–300 are the people that are most interested in using it. Maybe give them a free year. Maybe give them whatever free amount of time, but eventually they’ll convert in. Although billing a two-sided marketplace is a little different because you really do need those folks to dig in. Lastly, $20 or $25 for a year is like ouch.

Anna: You’re selling to consumers, too, which is a very different game. They’re so price-sensitive and RVers in general are. Essentially, we’re marketing to people who are too cheap to stay in the campground for a night. You’re really kind of scraping the bottom, but there’s also some degree on pricing. I mean they’re lovely people. As it grew and matured, it turned out that the savings of $25 or $50 a night on a campground was really not the value proposition that people actually ended up buying for.

Rob: What was it?

Anna: It ended up being community. Most of the hosts did end up being RVers themselves, but a lot of them were former RVers, people that couldn’t RV anymore, and people who ended up going to the effort to put in a couple of parking pads for Boondockers Welcome guests on their properties so that they could have people come and share their travel stories.

The same on the guest side. We had families who were traveling and it was just somewhere different to stop. You meet people on the road, people who know the area, people who are willing to show you around, people who give you eggs from their chickens in their backyard. It really ended up being much more about community than an alternative to spending the night in the Walmart parking lot.

Rob: That’s often what happens. There are a lot of businesses that we think it’s about saving money, and there’s often some other thing. It’s about saving time, efficiency, a hassle, or in this case, community, which maybe wouldn’t have predicted from the start.

By the end then—if we flash forward to 2021—I’m curious what your pricing was like then if it was still an annual subscription, if you’re still charging both sides, if the pricing was higher than $25 a year?

Anna: We did change our business model in late 2017 to allow hosts to sign up for free. Did not include (I guess) subscription, though. If hosts wanted to also be guests, they had to purchase a guest subscription but they got a 50% discount on that.

By the time we sold in 2021—and still great now—our annual price is $50 a year, so up from the $25 a year but still a good deal.

Rob: Yeah, and that makes a lot of sense to charge guests because they’re getting the benefit, whereas hosts, I know they get the community side of it but they don’t get paid, right? It truly is a free thing.

Anna: It truly is. We wouldn’t have existed without the generosity of our hosts, so yes, charging our hosts in the end definitely was not the right play.

Rob: What was that early assumption that every host will also want to be a guest? You often get in that mindset of something owned. I’ve written code where I coupled two classes, or made one class instead of having it be a more generic representation. It’s easy to do and then it’s something you just got to undo later.

You launched in 2012 and you do get one side of that marketplace, the host, in place enough because your mom has the audience, and then it’s growing onesie, twosie payments a week or every week or two, so truly slow growth bootstrap business. When did that change? I get the feeling there’s an inflection point here that happened where growth picked up, revenue started accelerating, and I’m curious what came together to make that happen.

Anna: It was sort of just slow growth. Got picked up by several influencers in the space slowly over time, but I think the big inflection point was in 2017 when I rewrote the tech stack, changed the business model. Honestly, that was when my youngest kid started school so I had a lot more time on my hands, and I was able to really focus on all the things that I knew we were supposed to be doing but we weren’t.

We didn’t even have a blog. We had no content marketing. We sent out newsletters but only to our existing members. We didn’t have a newsletter sign-up on the home page. All those things that you’re supposed to do, we hadn’t done them and we managed.

I think by the time in 2017 when I rewrote the stack, we had about $30,000 in ARR. It’s a pretty high-churn industry so that’s not a guarantee, but it was respectable for what was essentially just a maybe six-hours-a-week while my kids were in preschool or before I walk in evenings when I still had a day job sort of thing.

Rob: That makes sense, and at that point you’re five years into this business doing $30,000 a year. It sounds like you were fine with that, that you thought of it like a side project.

Anna: Absolutely. It was something I dreamed of quitting my day job for. I mean, I did quit my day job before 2017 for family reasons. My husband was traveling a lot and we needed some life balance. It’s not like two young kids at home who aren’t in school yet isn’t pretty much a full-time job. It was a side project and I treated it as such until I found the time to actually double down.

Rob: I am also curious about when you reworked it. You now have more web experience, I’m assuming. What tech stack did you use then in 2017?

Anna: We have a Django back-end. Obviously, Python Django running on NGINX and FreeBSD as our operating system. I happen to have my husband who is a bigwig in the FreeBSD world, so I have a good guy on board to help me with any of those OS server–level details. I didn’t even know Python (really) before I picked that, but it’s incredibly flexible, great from just the ability to implement anything I wanted after coming from trying to build on top of the Drupal CMS. It was a huge step up.

Rob: It sounds like your growth started moving a little more at that point because you did put things in place. Like you said, content marketing and other things that we would just say that most bootstrappers should be doing. Do you think if you had done that earlier, if you had the time do you feel like growth would have been faster in those first five years?

Anna: Maybe. I think the business model change was really imperative. I think we ended up losing hosts quite frequently because they stopped being guests. When we made that change, we were able to stop stagnating on our house count, and our number of hosts just really started to skyrocket. I think at that point we had about 800 hosts and we had sort of been oscillating around that for a couple of years. Today, we have over 3000.

Rob: And that’s the hard part. The hard part of the pricing period is you don’t know what do I feature gate, or what is my value metric often. A two-sided marketplace adds even more complexity than that. It’s who do I charge and for what, who’s getting value out of it. I can imagine that it took you a little while to figure out.

Your business is growing well, and I want to get to the kind of MicroConf part of the story right now. I’m curious. How did you hear about MicroConf? Were you a listener to this podcast?

Anna: Yes. I can’t remember when I started listening to Startups for the Rest of Us, but I’m pretty sure I was still working my day job and listening to it on and off. I knew that that was what I wanted, but I wasn’t sure that the business I had was going to be the business to get me there.

You guys do end up focusing quite a bit on B2B SaaS. We were B2C and not so much SaaS, so two-sided marketplace just didn’t necessarily feel like I was a fit in that I was able to put into place all of the suggestions that you made because there were so many differences. I had a lot of misgivings about whether or not I was really a fit for the MicroConf community.

Rob: Is that because of the B2C and the two-sided marketplace aspect of it?

Anna: A little bit, but also just because I was doing it on the side when my kids were in preschool. I don’t want to generalize what women think, but I know that I had difficulty with calling myself an entrepreneur when I spent my days with stay-at-home moms. It’s a difficult separation to make.

Rob: That’s one of the reasons we started this podcast. Mike and I didn’t fit into the prototypical YC founder. We weren’t the Silicon Valley person, the 24-year-old who could move there. I was already married with a kid and a mortgage, and I didn’t want to do the crazy, non-work-life balance, Silicon Valley 90-hour a week game.

We started the podcast because it’s for the rest of us, and we truly mean for the rest of us. I wish maybe I had said this five or six years ago when you could have heard of it at that point. One of the things I believe so strongly about bootstrapping is that it is this more inclusive or just there’s so much about it being is it a true meritocracy, maybe? Because you just went off and built a website. You built revenue and no one cared. No when asked if you were a man or a woman, or if you are a person of color or not. You just did it.

There are so many folks I think that if you had gone to Silicon Valley to try to raise money 10 years ago, it would’ve been perhaps hard for you. I move for the stories of the gender gap there. There are just all kinds of stuff that goes on with venture. I’m not trying to throw venture under the bus, in particular, but I do believe so hardly in this community, the MicroConf community, Startups for the Rest of Us, and even just the worldwide community of bootstrappers.

I do think there is so much more leeway for folks to just go and get it done because it’s about shipping a business and building a real business for real customers to pay you real money, versus anything else. You’re not putting on a show, you’re not trying to convince people or get permission from anyone to start a business. You’re just doing what you did, which was to hack together Drupal with your mom as basically an adviser, a subject matter expert, and to ship software.

Anna: Yeah, and honestly, at the end of the day there was nothing about Startups for the Rest of Us or MicroConf that put me off, but there’s always that representation piece. It’s like until you hear the story of somebody who you feel like they also did this while their baby was napping on their lap or while their kid was in preschool, and they were around the corner in the library trying to hack together Drupal. Until you feel that and hear it from somebody else, you’re always sort of questioning whether you fit in.

Rob: Absolutely. I should have talked more about that. It’s such a trip. My first child was born in 2006 and the second one in 2010. We started this podcast in 2010 and I used to record it with Mike while he was napping. I don’t know why I didn’t mention that. I never did, but I was in the same boat as you in those early days when I acquired HitTail. The second was less than a year old and I was still watching him almost full-time.

Anna: See? That’s really cool and I did not know that. And I’m sure that that’s true for a lot of bootstrap founders who quit their day job. It’s like, well, somebody’s got to put food on the table and it ends up being the wife. The husband in that case—if this is a man we’re talking about—ends up being that—a stay-at-home caregiver—but it just doesn’t get discussed (I think) as much, so those of us who are female and feel like that is often a role that we’re wedged into, don’t necessarily relate to that if we don’t hear that from the men who were doing that.

Rob: Yeah, I would agree. Again, I’m going to keep harping on, but I believe bootstrapping and just starting companies is so life-changing, building products. One of the reasons that I kept diving into it was because we had young kids. I wanted work that worked around my life. Life came first. My family came first. What can I do? I didn’t want to have a full-time job because that means I’m somewhere 9-to-6 or 8-to-5 or whatever it is, and it sounds like I think so many of us are doing it for that reason. Freedom, purpose, and relationships, right?

Anna: Absolutely. I wouldn’t have quit my day job if my husband was traveling a lot. We needed that balance. Even though Boondockers Welcome wasn’t anywhere near close to bringing in the revenue to replace my full-time engineering salary, it was a decision that was easy to make at the end of the day. We did not need my salary and we needed balance.

Rob: So in 2019, you get a purchase offer. You actually wrote me an email about six or eight weeks ago, and it was about the ultimate acquisition. One piece of that I just want to read here. You said, “In early 2019, I heard about the scholarships for underrepresented people from MicroConf, which I always wanted to attend but had never been able to justify the cost and time away from my family. So I decided to apply. I was surprised and thrilled to find that I’ve been granted one. I can say without hyperbole that receiving the scholarship changed my life.”

That has a lot of meaning to me. You’ve heard me say this. There’s a reason this podcast and MicroConf have gone on for 10 years. We’re essentially side project hobbies until a couple years ago, and it’s because of sentences like that. It’s us finding other people and us all helping one another make progress on this journey.

I want to hear, when you say it changed your life, give folks some background about what was going on coming into MicroConf and then how MicroConf maybe changed your thinking around that.

Anna: I’ve already said that I wasn’t sure that I was a fit for MicroConf based on how we had grown, my business, and my own personal sort of misgivings about my own skills, but I decided to apply for the scholarship and was accepted. At that time, we had actually been courted by another person in the RV space. A company that owns several blogs and forums that are well-known in the RV space, and they have made us an offer.

At that time, we had about $100,000 in ARR, and the offer was reasonable. We were still growing pretty well, so it was 3.9X-ish multiple. We had our accountants sort of look over it and go, yeah this a good offer. We had not yet signed an LOI.

I applied to MicroConf for the scholarship, thinking if I do go it will be an opportunity for me to learn what I will do with my next startup, so that I can really do it the right way. I went, thinking we were going to sell.

I swear to you, within the first hour, that very first night in the first mixer where I was just standing around having drinks, I had a conversation with somebody. I’m sad that I don’t remember his name, but he said, you should go read before the exit by the Dynamite Circle guys—I […] names, I’ve also forget.

Rob: Dan Andrews and Ian, yup.

Anna: That’s it, yes. It’s like thought experiments about other things you might choose to do before you sell your company. I went after that and had lots of other great conversations. I went back to my hotel room that night, and I think it was $4 on Amazon for this short book. It’s just thought experiments. I read the whole thing before I went to sleep. I’m on the East Coast time in Las Vegas, so I’m up until all hours of the morning. And that was. It was like, oh my gosh. What am I doing? Why am I going to sell this business?

Throughout the weekend I had more conversations with more people. They all just sort of said the same thing about, oh that’s really cool and you’ve got traction. A lot of people there were still struggling to find their first idea and here I was with a business that had made $100,000 that year. It’s like maybe this is a business that is worth pursuing and continuing.

That was how MicroConf changed my life. I did not sell my company. I came home and I said to my mom, nope, we’re not going to sell. Part of the reason we were talking about selling was she was looking to retire. She’s in her late sixties by now, and we’re like, okay, we’re going to figure something out. Either I buy you out or I take a salary or something, and we’re just going to keep going. That was how MicroConf changed my life.

Rob: That’s a heck of a story. It’s usually an exit and actually selling that changes her life—which ultimately did happen—but in this case it was not selling too early. At the end of the story, you kept growing. And then?

Anna: The end of the story is that I kept growing and then COVID happened. RVing went crazy and then I saw […].

Rob: Yup, and you could call it luck, you can call it serendipity, but honestly, something happened at that event. Something happened in your hotel room that night before the exit, that maybe it was meant to be or maybe it was just really fortuitous timing.

The sentence in your email to me is, “And now two years after the previous offer, we received a strategic offer from a venture-backed company in the space, that was of the ‘we be crazy to say no’ variety. Life-changing money that I can clearly draw back to a life-changing moment when I was offered the scholarship to MicroConf and accepted it.” It just warms my heart.

Anna: Everybody’s version of life-changing money is going to be different, obviously, but for someone who was planning to really quit my day job just so I could have some work-life balance, and my mother who was a waitress and doesn’t have a lot of retirement savings put away, now I don’t have to worry about that.

We ended up both staying on as full 50% owners. I took a salary so she gets half of our acquisition money. It’s definitely a special kind of exit to know that not only are you taken care of, but you help take care of your family as well.

Rob: I was going to ask you how that part panned out in terms of your mom, because I was imagining as a waitress most of her career, she didn’t have much retirement. That’s pretty incredible to think, like you said, it’s a double win because you get the money and so does she. Wow.

Congratulations. I feel great about the story. Honestly, whether this podcast or MicroConf had been involved or not, this is still a great story. It’s just a great story of building something to fill a need, getting that MVP out, and having the pricing not quite right. You had a little bit of an edge because you’re a developer and your mom is a subject matter expert with a little bit of an audience in the space allowed you to get that leg up. You made some mistakes along the way with structure, pricing, and this and that, but slow growth and you kept doing it. It’s a nine year to overnight success thing, right?

Anna: Exactly.

Rob: We’re good. Thanks so much for joining me on the show and telling your story. I feel like anyone listening to this can take away just the really life-changing nature of bootstrapping startups. I always say on the show, think in terms of years not months, because your story is one of those. It’s a realistic depiction of what most of us go through when we bootstrap.

Us bootstrapping is not the Facebook story. Even the story of ConvertKit or Baremetrics, when you look at it, they’re just growing tens of thousands of dollars. That does happen, that’s the Cinderella story version of it, but what do most of us experience and I feel your story is a lot of that.

Anna: Thanks so much. I’m so happy to have had the opportunity to be here and share the story, and to have obviously been able to attribute so much of that back to the MicroConf and the Startups for the Rest of Us community.

Rob: And if folks want to keep up with you, where can they find you online?

Anna: I am on Twitter @skulegirl.

Rob: Excellent, and MicroConf Connect, of course. You’re an active participant. It’s a free community that has a Slack room, but I don’t know. I think we’re around 2200 participants now. That’s where you and I (I think) really, really connected.

Thanks again for coming on the show, Anna.

Anna: Thanks so much for having me, Rob.

Rob: Thanks again to Anna Maste for coming on the show. Hope you enjoyed it this week. If you and I are not connected on Twitter, look me up. I’m @robwalling. I hope this week’s episode provided you with some inspiration or motivation to keep going, to keep shipping, to make that next sale. I’ll be back in your ear buds again next Tuesday morning.