Anna: I ended up sort of straddling this, stay at home mom world. But at the same time I had this thing that I felt like I wanted it to also be part of how I defined myself as a business person, as an entrepreneur.
Lexi: Did you find, was there a point in time where you felt like comfortable calling yourself an entrepreneur?
Anna: After I sold the company.
(both laugh)
What makes someone an entrepreneur? How many hours do you need to work in a week, or how much revenue do you need to bring in? We all carry assumptions of what building a successful business looks like. But are they true? Today’s story raises that question and will open your eyes to what’s possible when you carve your own path.
I’m Lexi Grant and you’re listening to They Got Acquired. A show about life-changing business acquisitions, and founders who don’t follow the Silicon Valley narrative.
Today, you’ll hear from Anna Maste, who co-founded a membership site for RVers with her mom. You’ll learn how this unlikely duo bootstrapped their way to a 7-figure sale — and how imposter syndrome almost got in the way.
Anna: He had expressed some interest in buying us earlier, but he reached out again and was sort of pretty insistent that, you know, come on, just, just name a number.
Lexi: “Name your number.” Not a bad way to start a conversation about selling your business. It was 2021, and the market was hot thanks to a global pandemic that made RV-ing one of the few safe recreation and travel options out there.
So… Anna Maste did name her number.
Lexi: I read it was a seven figure sale and all cash. Is there anything else that you can share with us about the terms?
Anna: Yeah. So mid seven figures, we, it was about 85% upfront. And then the last 15% over the following six months in six installments, sort of during the transition, I stayed on for those six months as a consultant for a small salary.
Lexi: How did you feel the day that the deal closed?
Anna: Bittersweet but mostly relief.
Lexi: If you’ve spent any amount of time building an online business, then it will make sense to you why Anna felt this way on the day the deal closed. After all, she and her mom, Marianne Edwards, had spent over TEN YEARS bootstrapping Boondockers Welcome.
Lexi: As a trained computer engineer and former waitress, it was a journey neither expected. Especially back in early 2010, when Anna was home in Ontario Canada on maternity leave with her first son — and Marianne shared with her a website idea.
Anna: It was more of a question about — she was thinking of hiring someone to build this website. And I knew that she had the idea, but I wasn’t sure how well it was going to take off.
Lexi: What was the idea? A membership site for traveling RVers, who needed a place to put their RV, and wanted something different than an RV park.
Marianne told Anna that she already had a name picked out for the website: Boondockers Welcome.
Anna: Boondocking is, you know, a thing in the RV industry that’s means you’re camping without hookups. So the idea was that you’re welcoming people to boondock on your property. So boondockers welcome.
She knew about couch surfing and how it lets people come stay on your couch overnight. And she wanted to create a community like that for our veers, where you could online go find other RV dealers who will let you stay overnight on their property.
RV-ers often will meet at a campground or somewhere else and very quickly we’ll, you know, become fast friends and invite each other to stay on their own property if they’re ever in your neighborhood.
Lexi: Marianne knew this because she was an avid RVer. She’d even written some e-books about camping and RVing affordably — and they sold well. Her website got decent traffic and the sales from the e-books brought in several thousands of email signups. Not bad for a self-taught entrepreneur.
But Anna had her reservations. After all, it was 2010 and website-building tools and platforms were limited. Anna knew that creating a membership site would take specialized skills.
Anna: I said, “I think it’s going to cost a lot more money than you should invest into it without knowing if it’s going to work.” And at that point I was on maternity leave and I said, “Hey, why don’t I see if I can do this for you?”
Lexi: So Anna got to work. She was on a year-long maternity leave that’s available to Canadians — but if you’re a parent, then you know those early months with a newborn aren’t exactly easy.
So while taking care of her newborn baby, she managed to put her coding skills toward building a membership site. It was far different from the kind of work she was used to with software development, but Anna saw it as an interesting challenge.
Anna: I didn’t have any web development expertise. I had been an embedded software engineer and, but I knew that the internet can teach me just about anything. So I sat down and started figuring it out.
Lexi: Can you talk about how you envision that first MVP, the first minimum viable product? Like what did your tech stack look like and what were you hoping to achieve with it?
Anna: At that point I opted to try to extend the Drupal CMS, which is essentially made as a content management system, not as a web development framework, but modules that you can use to sort of extend it. And I did some custom development when necessary, but we managed to essentially make the minimum viable product out of a Drupal CMS with some custom mods. And that was it.
It was definitely not really the ideal tech stack for this sort of a product, but for somebody who was coming in fresh and not really having a lot of expertise, it gave me enough comfort that I could get the job done.
Lexi: Anna worked on the MVP through the rest of her maternity leave and into the following year when she went back to work. She moved at a slow pace — an evening here, a few hours on the weekend there — basically whenever she had childcare. But Anna kept at it — even when she had her second kid in early 2012.
In fact, she and her mom launched Boondockers Welcome just TWO months into her second parental leave.
Anna: We had some beta testers from my mom’s email list right around then who started testing and in April of 2012 was when we officially launched.
Lexi: It sounds like she was somewhat marketing savvy because she had an email list, so she knew to collect emails.
Anna: Yeah, we had a great starting place when we wanted to find some hosts who were perhaps willing to let other RV owners come stay on their property for a night or two.
Lexi: At this point, Anna and Marianne figured out exactly what each of them were going to do in the business. As the RV expert, Marianne was the face of the company. She’d already gained trust through her RV travel guides, and continued to build on that by being the main point of contact with customers.
Anna: She had the RV and chops and I was just the, the person in the background doing the tech and, and, and that was fine with me.
Lexi: You’re a technical co-founder.
Anna: Yeah, exactly.
Lexi: People try really hard to find those these days. They’re hard to find. Maybe this didn’t come till later, but I’m curious about how you talked through how much each of you got paid and who had ownership of the company.
Anna: I mean, I think we set up front, you know, we’re going to be 50-50, and then we never really sort of dug into the wall. Are we going to keep track of how many hours people are working? And I mean, at that point, honestly, even if she wasn’t working on the business, the fact that she was taking care of my kids while I was working on the business was enough to make it feel like she was doing her share.
And she was working on the business as well when she was at home. And then when we incorporated in 2012, when we actually, formed a proper legal corporation and it was 50-50.
Lexi: By this point, you’re probably used to Anna’s modest, easygoing tone. So let me be clear: the fact that this woman built an entire membership site on the side of her day job while bringing two babies into the world? That’s impressive. very impressive.
But Anna didn’t see it that way.
Anna: It was always a side project at that point. I hadn’t really gone into it thinking I’m going to start a company. It was just, here’s something fun for me to do that keeps my brain sharp while I’m on maternity leave or that I can play with in the evenings after the kids go to bed.
Lexi: No matter how much Anna and Marianne thought of Boondockers Welcome as a side project, their idea was a good one. And as time went by, it became clear that Boondockers Welcome had a distinct advantage over its competition: they were creating exactly what Marianne, an RV enthusiast, wanted to use. Something small and community-based that celebrated the lifestyle of RVers.
Anna: We were talking to our customers. There were two of us, right? Like our best hosts, you know, we know them by name. We, you know, my, my mom has stayed with, you know, dozens of them.
Lexi: Because of this perspective, Marianne and Anna were able to find a niche in the market that social networking sites or large, venture-backed companies like Airbnb or VRBO wouldn’t necessarily set out to serve.
Anna: We worked on a membership model where our guests could stay with any of our hosts for free during the entire year that they paid us a membership. And our hosts don’t charge. Our hosts are essentially, usually other RV years, but people who are looking at.
It’s more of a social opportunity for them than a money-making opportunity. And in fact, once money starts changing hands, it becomes a bit of a logistical nightmare. Sometimes you’ve got to deal with insurance and, you know, should I be reporting this on my taxes and such. And so most of our hosts that while our hosts are not allowed to accept money, except for if they offer you an electric hookup, you’re allowed to compensate them for their out-of-pocket costs.
So while Anna and Marianne had found a niche in their market that was completely underserved, there was a lot they didn’t know. Like — did their business model really make sense for the long run? How long did they want to work on Boondockers Welcome and could Marianne ever leave the business?
These were important questions — but ones Anna and Marianne frankly didn’t have the time or energy to answer until Anna made a big lifestyle change.
After the break, you’ll learn exactly what that was, the moment they almost sold the business, and details of the 7-figure deal that funded Marianne’s retirement.
Anna: Hold on one second. I have a cat meowing outside my door.
Stay with us.
AD BREAK
Hope you’re enjoying this amazing episode of They Got Acquired, as you hear Anna Maste tell her story of her life-changing exit. Part of that story is that she was heavily impacted by attending a MicroConf in-person event that changed the course of her exit for the better. Well, I’m Rob Walling, Co-founder of MicroConf. MicroConf is where bootstrapped SaaS founders launch, meet, learn, and grow. We’ve been hosting in-person events for more than a decade, we have an online community and extensive video vault.
If you’d like to learn more about MicroConf and how we help founders grow their companies and connect with other founders—and often see them off to amazing exits—you should head to MicroConf.com/endwell. There, you can get free early access to a MicroConf growth talk that was given just two weeks ago called “Ending Well: The Complex Psychology of Exiting Your Company.” It was given by acclaimed startup consultant and advisor, Dr. Sherry Walling. Normally, we charge $50 for access to our talks, but we’d love for you to head to MicroConf.com/endwell, and get early and free access to that talk.
—
Hey, I’m Bobby Burch. I’m a reporter with They Got Acquired, and I’ve been covering startups and entrepreneurship for the last decade.
Did you know we offer so much more than this podcast?
On our website, you’ll see lots of stories explaining how founders built and sold their companies plus resources that will help you figure out how to go about selling your business. And soon, we’ll be releasing insights from our database, tracking hundreds of deals under $50 million.
The best way to access this all is through our newsletter. If you’re not already signed up, head over to theygotacquired.com/newsletter. We’ll see you in your inbox.
Anna: It was 2014 when I actually quit my day job. It was not because the company had grown big enough to let me do that. It was very much because my husband had taken a new job that involved a lot of travel and he was away a lot.
And my eldest had, you know, just started kindergarten and the youngest was still in daycare. And I was trying to like shuttle all these kids around and get to work. And I remember where my husband was away and the car broke down and I realized it’s like, I have to get one kid to school, one kid to daycare, myself to work.
And I have no car. No. We took public transit, but it was a nightmare one day because you’ve got car seats. It’s like, not like you can just hop into a cab easily. Right. So that was sort of the straw that broke the camel’s back. And I’m like, we, my husband made very good money. We did not really need that second income.
And I wasn’t really fulfilled with my day job. Obviously I talked about it with my husband, but we, I quit to be home with my kids and to be there for my family mostly, but with always the idea that maybe I could then put a little more time and effort into the company and see if I could grow it further.
Lexi: So you’re the primary caretaker and you’re also trying to make progress on this project. How did that look for you? Like what were the logistics of the day to day?
Anna: So I would take the older one to school. I would walk the younger one over to preschool in his stroller. And while he was there for two and a half hours, I would go to the library that was around the corner from his preschool. And I would sit there and I would work on the business. And that’s what I would do. So for two and a half hours, two or three days a week, that was what I managed to work on the business for those first couple of years after I quit my day job,
Lexi: And how did you feel about that? Did you, were you happy with the balance you had? Were you moving at the pace that was satisfying? Because a lot of people are in this position where we don’t have 40 hours a week to work. We might have 10 or 20 or 30 and kind of re-imagining what the work life should look like. It can be challenging when it feels like everyone else has a lot more time to work on their projects.
Anna: I loved it. I loved the balance. I loved the ability to, you know, if I’m only working seven and a half hours a week, but you know, they’re a solid seven and a half hours where I’m able to focus. Um, and I feel like, you know, it was definitely slow moving. There was no rocket ship growth at that point. That’s for sure.
But we were. Gaining traction bit by bit. And that was enough. It was enough for me to feel like I was doing something that was meaningful and that I had a purpose.
Once her youngest started Kindergarten a few years later, Anna had a little more time to spend on the business. And she didn’t waste it. First, she rewrote the entire tech stack for Boondockers Welcome and added some new features.
Then, she and Marianne made a huge adjustment to the business model: they allowed hosts to join for free.
Anna: We had actually thought that all of our hosts would also be our RVers and would be guests using the network as well. And so we just had one model where everybody paid a membership.
And if you were a host, you got a bit of a discount. But then we very quickly realized that we couldn’t keep our hosts because they would stop our being and then they wouldn’t be hosts anymore. You can be a host for free but if you wanted to use the network as a guest, it was an annual fee of at that time $30, which is. An incredible deal.
This new setup lowered the barrier of entry for hosts to sign up, giving members of Boondockers Welcome even more choices of places they could stay.
It worked well, and continued going well for the next two years — until Marianne, came to Anna, in 2019 and said…
Anna: I don’t think I can do this for that much longer. I would like to retire soon-ish.
Marianne was pushing 70 at this point, and Anna was feeling a little burned out herself. So when they got an offer from another company in the RV space, they seriously considered it.
They had worked on Boondockers Welcome for well over 8 years, were earning around $125,000 in Canadian, and had grown to 3,000 members and 1,500 hosts. Maybe their time with the company had run its course. Maybe, it was time for change.
While mulling over this decision, Anna applied for a scholarship to attend a conference called MicroConf.
Anna: MicroConf is a conference started by Rob Walling and Mike Tabor who are the hosts of Startups for the Rest of Us. It’s been, you know, probably a decade or close to that now that they’ve been running that conference. But 2019 was the first time that I had ever gone to it. I had heard of it and, you know, always thought, oh, that would be neat. But again, sort of that imposter syndrome, I was never really sure whether or not I was a good fit. Whether or not — again I was having trouble defining myself as an entrepreneur.
Anna won the scholarship and flew to Las Vegas, ready to learn and meet other business owners. Her goal was to use this time to think through what she would do after she and Marianne sold Boondockers Welcome.
But that’s nowhere close to what happened.
Anna: I ended up having so many conversations with people who were in the same position I had been earlier and were looking for a product that would be as successful as ours was.
And I realized that we actually had something pretty special and it would be pretty silly to give up on it at that point. So I came home from that conference and told my mom. We’re not going to sell. We’re going to hire someone to replace you.
Energized by the conference, Anna immediately looked for help from the Boondockers Welcome community. Less than a year later, with help from an RVer from Alaska who had a background in marketing, Marianne was finally able to retire.
Anna: She stayed on as a 50% shareholder and we, I just started paying myself a salary in order to compensate that way for extra work that I was doing. But that was sort of a real turning point, I guess, because I doubled down on the, on the business and it grew a ton after that time. I’m very glad we did not sell at that point.
Lexi: When you said we double down, what did you double down on?
Anna: We really started, using all the things that I had learned about marketing, but had never really gotten around to implementing to be honest.
Anna raised the Boondockers Welcome membership price and worked with her new hire to write content about RVing. They recruited guest bloggers to write for Boondockers Welcome, and started sending out more frequent newsletters.
Anna: We started just sending out a weekly newsletter with all our newest hosts, and that was brilliant and easy. And, I, you know, I coded up something to just dump that out directly into our email providers so that it was pretty easy. You could just click a button and all of the new hosts would show up there.
And that turned out to be a fantastic driver. We had lots of people who, you know, are thinking about planning, dreaming about their future RV trip and would sign up for our newsletter. But then seeing, oh, wow. There’s all these hosts in this area that I’m planning on traveling was the thing that would push them over and get them to buy.
The next year was a whirlwind of growth. All the groundwork that Anna and Marianne had laid over the years and the trust they’d built — it paid off. 2020 brought a surge of traffic and membership sales that neither of them could have foreseen.
The cause? A global pandemic.
Anna: The pandemic really made the RV thing go even crazier than it had already been going. So the RV market went kind of nuts and, we actually had several investors, private equity firms sort of reach out to us.
I don’t think that I was necessarily looking to sell, but there is also just, you know, thinking about my mom and she was, we were paying ourselves dividends every year on top of my salary and sort of those dividends at that point were funding her retirement. But being able to offer her. The security of knowing that, you know, she’s set now. That was a huge part of sort of deciding that maybe this would be a good time to sell.
Lexi: And when did you decide you were ready?
Anna: there’s another company in the space called harvest hosts and they had a very similar business. That was also membership-based they, but they worked with, wineries and breweries and museums and other small businesses encouraging them to welcome our viewers to come spend the night, typically in exchange for the RV years, buying something, a bottle of wine or, or visiting the, the music.
And we had developed a relationship with them over the years, we had reciprocal discounts for each other’s platforms, and they took $37 million in funding earlier that year. So they were clearly on the trajectory to continue growing even bigger. And they had grown quite a lot.
Because they were in the habit of getting an annual valuation, Anna had an idea of what their business was worth. But she also knew she had some leverage. First off, Harvest Hosts wanted to increase their host base, and acquiring Boondockers Welcome would double their current number of hosts.
Second, the pandemic had accelerated their pace of growth so dramatically that the buyer was very eager. And finally, Boondockers Welcome came with some amazing brand recognition. So Anna talked to some friends who worked in the VC-backed startup space, and asked how they would arrive at a fair price.
Anna: We came up with a number that seemed that my mother and I agreed, we would be very, very happy to finish with. And we brought that to Harvest Hosts and they pretty much very close to met that. So at that point it was pretty much impossible to say, no,
The deal was set at mid-seven-figures, with the majority paid up front and the last 15% paid out monthly over the six months that Anna would stay on as a consultant.
So, in March 2021, Anna and her mom signed the LOI, their letter of intent — and began the process of selling their business.
Anna: It was 43 days of craziness. Because they had taken funding from a firm, they had the firm’s lawyers —you know, big New York lawyers —like four lawyers on the deal who were constantly sending me things that I needed to get for them. And of course it was, I think we were in lockdown here for part of it. And my kids were learning distance from home. And there was a lot of craziness in that month and a half.
Lexi: Do you have any tips for other entrepreneurs who are building companies that they may eventually want to sell?
We use a lot of open-source software, right? Our web framework is Django, which is open source. We use JavaScript libraries that are all opensource. And if you’re getting acquired, they will want to sort of make sure you’ve got permissive licenses for all these software packages that you’re using. So be very careful when you’re building your product using open-source software, that you are not, there are, you know, copy left versus copyright licenses that, that, are just more, more difficult from a legal standpoint. You’re not necessarily breaking the law by using them, but it’s just, lawyers will be kind of particular about that.
Eventually, after a long 43 days, the lawyers finished lawyering. Anna stayed on as a consultant as promised, and with mixed emotions helped Harvest Hosts maintain the website and mobile app she’d coded until they transferred it to their own tech stack — effectively eliminating the code she’d written. Which… let’s be honest — must’ve felt a little brutal.
But with the deal officially done? Anna can see the big picture — the opportunities it’s given her, and what it means for her mom.
Anna: Now she has an actual investment advisor. Who’s investing her money rather than having a bunch of money in GICs sitting there, not actually earning anything. And I think that’s maybe the biggest change for her is just not having to constantly worry about training down her savings and being able to enjoy retirement.
Lexi: That’s really good. How was this journey of not just the acquisition, but the journey of building the business? How was It life-changing for you?
Anna: It gave me freedom. It gave me the opportunity to pick my kids up from school every single day, to walk them to school every single day to be in their lives in a way that I would not have been able to be before. I certainly don’t think that women can have it all. I think the myth of having it all is damaging and drives many of us insane, but I think that I came as close as I could while keeping my sanity by being able to.
Be there for my family, be there for my kids and build something that I was proud of — that in the end served us better financially than keeping my day job ever could have. You don’t have to fit into the mold, you don’t have to choose between family and your career.
Lexi: That’s really cool. I got the chills when you’re talking about just being able to pick up your kids after school. And it’s the simple things that so many of us want.
Anna: It’s true.
So to go back to that question, what makes someone an entrepreneur? Well, I think the answer is wider and more expansive than startup culture has led us to believe. It might look like working only seven hours a week. Or building a business with your mom. Or coding while the baby sleeps (if you’re not napping yourself that is).
The point? There’s room for all kinds of people, needs, and schedules. Don’t let impostor syndrome tell you otherwise. Including you, Anna.
Thanks for listening to They Got Acquired. I’m Lexi Grant, and if you want to learn about more business acquisitions like Anna’s, go to TheyGotAcquired.com and sign up for our email newsletter. We’re building all kinds of resources for founders, investors, and anyone who’s interested in building and selling online businesses.
And before we wrap up, I want to thank Anna Maste for coming on the show and sharing her story. You can look for ways to connect with her in the show notes.
This episode was produced, written and sound designed by Laura Boach. If you liked this story, please share it with a friend, and leave us a review on Spotify or Apple podcasts. With a podcast as new as ours, every single share and review truly matters.
Thanks again, and we’ll see you next time.
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