Episode 453 | How a Non-Technical Founder Built and Sold a Multi-million Dollar SaaS Startup with Jeff Epstein

Rob: In this episode of Startups for the Rest of Us, I talk with Jeff Epstein of Ambassador about how he, as a non-technical founder, built and sold a multi-million dollar SaaS startup. This is Startups for the Rest of Us Episode 453.

Welcome to Startups for the Rest of Us, a podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing software products, whether you’ve built your first one or you’re just thinking about it. I’m Rob, and today with Jeff Epstein, we’re here to share our experiences to help you avoid the same mistakes we’ve made.

Welcome back to Startups for the Rest of Us. On this show, we talk about building startups in an organic, sustainable fashion that allows you to focus on your personal freedom, purpose, and relationships. We have different show formats and this week, I sit down with an accomplished, impressive founder named Jeff Epstein. I’ve known Jeff for around eight years and watched in awe as he built Ambassador—it’s at getambassador.com—into a $5–$10 million ARR SaaS company, and all the trials, the tribulations, the struggles of what he went through to get there. He exited about seven or eight months ago.

What I like about Jeff is that at heart, he’s a bootstrapper. He bootstrapped Ambassador—which was, at the time called Zferral—for a year and he had to pay a developer essentially out of his own pocket. Then he raised a very, very small round between $25,000 and $50,000 just to basically keep the product moving forward. He’s a scrappy founder. He was doing sales calls constantly in the early days, really, a founder who was ambitious.

One of the interesting things we dig into today is how he has a kind of what a bootstrapper mindset had to raise funding to keep the company growing and we talked through his decision to do that. We also talked about the toll that the company took on him over the course of this time. He said he didn’t sleep very well, he did feel stress, he put on a lot of weight that this company took a toll on him, and we walk through any regrets he has. It’s really a fascinating story.

The latter half of the interview focuses on the acquisition because I find that level setting people’s mindsets of what a real acquisition looks like. The fact that Instagram was supposedly sold in a weekend for a billion dollars is like, (a) we don’t even know if that’s really true or if that’s just kind of a myth and the story around it, and (b) even if it is true, that’s like a once-in-five-year thing or once a year, once a decade, whatever, very, very, very rare.

The other thousands and thousands and thousands of companies and startups that are acquired happen much more like what you’ll hear Jeff talk about today. Again, the latter half of the interview focuses on that. Then it’s fun to talk through with Jeff to hear what he’s been doing for the seven months since he was able to leave the company. I always enjoy sitting down talking with Jeff, really enjoyed the conversation and digging into his victories, his struggles, his failures, and everything that came along with it.

Oh, and one side note before we dig in, it was an absolute comedy of errors trying to get this recorded so I’m actually impressed that we’re even able to ship it. I was in a Starbucks—which I normally don’t work from coffee shops—I especially don’t record interviews from coffee shops but due to extenuating circumstances, that’s where I was. Fire alarm started going off an hour before the interview then stopped, then went back on, then went off, then went back on.

Eventually, I went out to get my car and take off and fire trucks had blocked the driveway so I literally could not leave so I sat in my car, I hooked up my hotspot to my phone and this entire interview was recorded using that USB headset plugged into just a laptop sitting on the passenger seat so it was a funny moment. I couldn’t cancel the interview because the episode wouldn’t have gone live on time. But the show must go on, we ship every Tuesday morning. I hope you enjoy my conversation with Jeff Epstein.

Thanks so much for joining me on the show this week, Jeff.

Jeff: Yeah, great to be here, Rob. Thanks. I appreciate it.

Rob: We go way back. We were in a mastermind with Ruben Gomez for a couple years, if I recall back, when I was doing HitTail, 2011–2012 timeframe.

Jeff: Yeah. It seems like a long time ago but it was a lot of fun and I know, at least for myself, it was a really valuable time to chat with folks. Also, there wasn’t a huge community and we’re all in interesting areas where there weren’t startup communities and it was really important back then and, obviously, so today. It’s cool that we remained friends for so long.

Rob: I agree. I see you at MicroConf every so often. You made it this year. It is cool that we ran across each other. I remember you and I originally met. I came and spoke, I believe it was in Grand Rapids and you live in Detroit, Ruben was in Florida, and I was in Fresno, California so we were all in these places where there wasn’t a huge startup community around us and we found each other through these channels.

Today, I want to walk people through your story because, as I was saying right before I hit record, your story of growing Ambassador as a non-technical founder is so compelling, it almost writes itself. We just cover the points and it’s like, “Oh, man, that was amazing.” “Oh, man, that was brutal. How did you get over that?” These are the best kinds of stories where there’s a lot of adversity and struggle and it was probably pretty painful at the time, the different things that happened with co-founders and whatever, fundraising, and working 24/7 for a few years, but I do think the folks are in for a pretty good ride today so thanks again for sharing your story.

Jeff: My pleasure and I’m excited to tell it. It is interesting and there’s certainly a bunch of highs and lows, so hopefully I can help some people avoid some of the stresses and struggles that I had but definitely interesting for sure.

Rob: To summarize, so we don’t have to spend 10 minutes going through details, you started Ambassador in 2010, you exited, sold the company in 2018 to a company called West Corporation. Ambassador was originally called Zferral and you did raise a few rounds of funding, I believe. You started working on Zferral/Ambassador in 2010 and you raised a small angel round between $25,000 and $50,000 in 2011. You’ve been self-funding it since then.

You mentioned to me that your wife was making money and you were pumping the money out the back door into the app. What was the impetus to raise the angel round? Because I think of you more as a bootstrapper. You just have that capital-efficient, you’re not the Silicon Valley go-big-or-go-home billion dollar valuation, you’re ambitious, but you don’t fit the mold of, “I’m going to topple Salesforce and become the next Dropbox, Facebook, and Airbnb.” What was the impetus for taking outside money in 2011?

Jeff: Good question. For me, it was really in a sense kind of bad, but it was almost desperation mode. I didn’t act like that—I don’t think—at the time, but for me, I had done pretty well, I guess, for being an adult without having an actual job, I was investing in real estate, I was doing some odd things, I had just come out of law school, and I had sold a small business that helped me pay off my loans. I didn’t have that much money saved up or capital, and again, it was coming off of the 2008 financial situation, so there weren’t a lot of jobs.

I basically self-funded Zferral and it was maybe $4000 or $5000 a month to pay for developers to build the product. A couple of things led to me raising money. One was there wasn’t this playbook that exists today in terms of how to bootstrap even. Bootstrapping at the time, was just grinding it out and getting money wherever you could. I kind of exhausted all avenues. The problem for me—I mentioned this earlier to you—was I couldn’t stay up late and get the app done. I wasn’t able to just do the work because I couldn’t write code. I had to basically pay for it.

At the end of the day, I had an opportunity to raise $25,000 and I took it because I got married in 2010. So, right before this money came in 2011, I had to think about my wife in terms of, “Hey, it’s not just my money I’m risking now. It’s our partnership.” She was kind enough, she believed in me, and allowed me to do it but it was at a certain point, literally, the money was coming in and it was going right out. She wasn’t making, even maybe me, even more than what I was paying out. Our household was a net deficit, which is pretty tough to do when you’re just getting married and just bought a house.

She’s used to always joke, “I thought I was marrying an attorney and this isn’t what I signed up for.” She was a good sport. She’s joking about it, but I don’t know if she knew that was what she was getting into. It was a big relief at the time and $25,000 was probably six months of expenses. I was fine not getting paid, but money going out was tough when I wasn’t making anything.

Rob: And at that point, you had maybe a couple of grand in MRR, you think?

Jeff: Right. The other thing is, at that point, we probably just started getting customers. I don’t think the customers could fund the development and sustain the business. As that started happening, again, I probably didn’t take a salary until maybe after Techstars are around Techstars which was 2012, but again, just not losing money. I remember that was a big turning point in my family. It was like, “Alright, we’re not losing money anymore.” We’re just not making any money, but we’re not losing money. That was pretty big.

Rob: Getting back to break-even. It’s tough, man, in an early, I won’t say new relationship because you guys have known each other, but a new marriage and then trying to scramble and start a startup like that. Do you have any regrets around that, either raising the money initially or not learning to code at some point? Anything you would do differently? Or do you feel like no, you came to play, you showed up, and you made it happen?

Jeff: I don’t have any regrets about it. I do think it would have been smart for me to learn how to code. That would have saved a ton of stress and heartache. As you know, I’m willing to do the work so being able to do the work would have been hugely valuable for me instead of having to rely on somebody else. Even just being a control freak, which you think a lot of founders are, it would have been better if I could do it myself.

That being said, I think the value and what I was so lucky was that my wife was supportive and understanding about it, so as hard as it should have been, it wasn’t nearly as hard as it probably sounds. But overall, no regrets.

Rob: That makes sense, you look back today and you’ve had this successful exit. Everything worked out, but at the time, when you’re grinding it out for a year and you’re at $1000 or $2000 MRR, you just started taking customers, and you’ve spent tens of thousands of dollars, I’ll assume it’s hard. That’s not an easy place to be in, I can imagine.

Jeff: Absolutely. It was super tough. It was a perfect storm of being naive and young enough where it would be a lot harder for me to do that where I am in my life today in terms of age and expectations. Fortunately for me, I was willing to do it. It is hard and looking back, you’re like, “Wow, I can’t believe I did that.” But you also don’t know any better. That’s part of the beauty of it.

Rob: I know you’re under NDA for the acquisition terms, but I’ll ask it in a more vague way that I feel like people have asked me on the record about the Drip acquisition as well. You sold the company last year. Did you make enough money that you don’t have to work again if you don’t want to?

Jeff: Yeah. For the most part, we definitely can live a comfortable life based on how things went. We could survive and be pretty well-off. The reality is we both want to continue working. My goal is really just to focus on things that I’m passionate about and just have the cab of more fun. That’s a big change going forward and has been already.

Rob: That makes a lot of sense. I’ve done the same thing. The passion is like TinySeed’s what I’m excited about and it’s nice to have the luxury of basically not getting a paycheck for a year or two, or three or five. Einar and I got our first paycheck from TinySeed last month and it was like, “Yay,” but I couldn’t have done that 10 years ago. You can’t just not take a check for a long time, so it is nice to have the luxury.

I know how much of a hustler you are and when you find that next thing, while I hope you don’t go as all-in as you did on Ambassador—because you’re right, and I walked through a year or two of it with you when I saw the toll it was taken on you—I do think that you’ll find that spark again and you’ll go mostly in on something that you’ll be working on.

Jeff: Yeah, it’s funny you say that. It’s something that I’ve even talked to my wife about is that I’m concerned that I won’t be able to do 80% or whatever the number is. That’s a healthy amount of all in this because I always tell people, “I’m not all-or-nothing kind of guy.” I’m not good at, “Oh, yeah, I’ll just work for X hours a week.” Even if it’s 20, or 40, or whatever it’s supposed to be, or 60, if I say it’s that, I’m not realistically going to stop unless I feel like I did everything I could. It gets harder and you just get worn down. For me, it definitely had that happened.

I’m getting close to 40 years old so it’s like, “All right, I need to start reevaluating my life and looking at it a little bit differently than feeling like you’re a college kid,” which is what I felt like for the last 10 years, probably.

Rob: It seems like one of your goals with the next one should be to control your work, to work 35-hour weeks, or 40, or some reasonable amount.

Just to wrap up the intro story so that we can dig into some of the points, you mentioned you went through Techstars in Austin, that was mid 2011, that was back when Techstars wrote really small checks, so it was like $18,000. It was just a stipend. Then I think the next year, they started giving $100,000 notes which probably sucked for you to not get that. I’m imagining you could have used that money at the time.

Jeff: Definitely, and we were in New York so it was even more expensive to live. But yeah, it was during the class, they announced the $100,000 note and it was super big bummer for us because we were one of the few B2B companies, and at the time, 2011, that also meant we were completely unattractive to investors especially in New York. We had a really hard time raising money while all of our cohort, basically all the B2C apps, all the mobile apps, they easily raised money. I don’t think any of them are around now, but they had a much, much, much easier time raising money than we did. It was really tough.

Rob: Then you raised a couple of hundred grand in a note in 2012 and then you did raise a Series A in 2015. So total over the course of several years—that’s almost five years—you brought to about $2.75 million. I know you mentioned earlier, you needed that early money to fund development because you couldn’t write the code itself. In 2015, when you raised $2.4 million, what was the thought there? Was it that you’d hit product-market fit, you’re growing super fast, and you need money for bodies? Talk me through the logic.

Jeff: Yeah. It’s funny thinking about this. Someone asked me the other day and thinking about my thought process, I didn’t run a process, which is a little bit different than most people. It was an opportunistic fundraise. I had—and you probably know this personally—at the time, fundraising wasn’t on my radar.

We were mildly cash flow positive. I would say five figures cash flow positive and then maybe the team was 10 or 11 people. There were certainly people there. It was a ragtag group of folks. I would say most people weren’t experienced startup or tech people, it was like you’re hiring people that would be willing to work with you even though you could offer them almost nothing in terms of benefits or comps. That’s always tough.

One of the reasons why we raised money and one of the goals that I had before I even started Ambassador was I really wanted to help build the community in Michigan, I wanted to create an environment where these companies survived and thrived, and where people wanted to go to work every day. That was what I wanted to build. I realized that incrementally adding one person at a time and being really, really lean, I mean, I was super lean. I was paying myself $40,000 a year. Our office was all IKEA furniture. It was just really hard to create that environment with such a lack of resources.

When Arthur Ventures came along and pitched me on a partnership where they said, “We’re not going to make you step out of your comfort zone and try to grow at all costs. We do respect the way that you’ve built the company and that,” I think the director said, “you wouldn’t die. You should have died, but you didn’t because you were willing to just fight.” I just saw this alignment there and I said, “You know what? This could be really good.” We had great people and we got lucky that the people that we hired early all ended up being amazing and grew into amazing pieces and teammates. Even more awesome to begin with, but being able to spend ahead of where we were, it was a big accelerant for us that we needed. It allowed us, again, to give people benefits, to up comp, and do some of the things that I wanted to do. There was no money to be had before that, so really that was why I raised money.

Rob: It sounds like you found money on terms that made a lot of sense for you to raise and didn’t come, perhaps, with a lot of the strings attached that maybe a lot of the Silicon Valley money would come with. Whether it still does today, it’s still evolving, it’s becoming more founder-friendly. But is that accurate? You found someone willing to give you a couple of a million bucks in a way that made sense for how you wanted to grow the company and didn’t negatively impact your optionality down the line.

Jeff: Yeah. I have a ton of respect for Arthur Ventures and Pat. They were awesome and it was a really great fit. Did we want to build a $100 million company? The answer is yes. The expectation was we were going to try our hardest to do that, but what I always said to him is I don’t want to leverage the business to be successful. I don’t want to get to $100 million or die. I think that’s something that many VC’s, if they hear that answer, they’d be like, “This isn’t the person for me,” which is fair and in some cases, they want you to take that swing and if you miss, they’re okay with it and they can go to bed at night. I didn’t want to sleep at night and saying, “Everyone could have had a really great career and a really great experience,” but I selfishly went for it and we all went home and that was it.

I think there was an agreement there. I know for a fact we weren’t the best outcome for Arthur’s. I definitely do feel bad about that and I know that I tried my best to be both smart enough and calculated to maximize the outcome without killing the business. We got pretty low, to be honest, in cash multiple times, way lower than we agreed to get because we were trying everything we could to continue to grow as fast as possible to get to the next stage. But yeah, it was definitely founder-investor fit for sure and we have nothing but great things to say about Arthur and Pat who’s awesome. When they offered, we negotiated a little bit and that was what we did.

Rob: That makes a lot of sense. Something that I want to dig into is the fact that you said you got pretty low on cash multiple times. You and I both mentioned that you were all-in and you were basically working 24/7 for several years. This all sounds like not fun. That sounds very stressful. Was it that in the moment? When you were doing it, were you thinking to yourself, “Oh, my gosh this is brutal”? I would have been stressed, let me put it that way. There are people who just absorb that and they just don’t feel the stress about this stuff. Talk me through. It’s an eight-year period, so it’s hard to nail anything, but I’m just curious. Were there moments when you were like, “I don’t think I can keep doing this. I’m going to explode”?

Jeff: To be honest, not really. I like stress for the most part. I used to always tell people—maybe this is a bad advice—I would say if you care about something, there’ll be a level of stress. To me, that shows that you care. There was, looking back, more stress than I would have liked, but I’m also the kind of person who loves to dive in and obsess over something. When it doesn’t go exactly as you want, then it becomes what I would consider to be stress. Whether that, at one point in my life, was playing poker, or another time in my life, it was wondering to play sports or whatever, those things were, at a certain point, super stressful to me but in a way that it didn’t bother me that much.

To me, it manifested in things like gaining a lot of weight, not just being exhausted, not working out or not being able to sleep, things that I reasonably should have been able to do but I just couldn’t focus or prioritize for those things because I was so concerned about doing everything I could for the business.

There were very few times where I’m like, “Oh, my God I need a vacation.” I always thought like, “Man, I’m really stressed,” but day-to-day, I really enjoyed it, especially post-Series A when we had a little bit of money in the bank and I was surrounded by more people that felt like peers. Some of the early employees became good friends, so it’s not that but people that had experience.

For a long time I felt like I was doing everything myself. Of course, my CTO and co-founder, Chase, was an amazing help, but when we added a couple of more folks and we had a leadership team, so to speak, that took a lot of burden off of me. The problems became different problems. It never got less stressful, but it became a little bit more fun for me and allowed me to keep going despite some of those other challenges.

Rob: I know you applied to Techstars one year and you didn’t have a co-founder. You had an agency or was it an offshore developer and you got rejected. One of the things they said was, “We don’t really want a non-technical single-founder type of thing.” So, you came back the next year and you applied with a technical co-founder but he was almost like employee number one, is that right?

Jeff: Yeah. The next year I had applied to Techstars. I had done some networking in between the two applications. I had a reasonable feeling that I might be able to get in the next time in New York. I had known some people that were in the prior class and they’re like, “You need to have a technical person show up with you,” so I hired somebody who, again, technically we’d called him a co-founder and certainly he deserves that title, but he was basically hired a couple months before TechStars New York, to just basically help rewrite that code base from the original Zferral one, which was what I applied with into Ambassador, which we ended up leaving with, so to speak. So, we had rewritten the code base.

Rob: That was your first to rewrite of the code base. Didn’t you rewrite it again in 2012–2013?

Jeff: Yeah. We rewrote it again. Soon after when Chase joined—he’s still part of the team and actually onto bigger and better things at West now—one of his first projects was really to undertake start migrating the code base to something a bit more scalable and in a more modern technology. We were previously PHP and then we moved it over to Python and Angular, which became React eventually. It was a big undertaking. We probably started that 2013 and it may have taken a year or so, but we did it in a compartmentalized way. We didn’t really slow down the site too much, but there’s a lot of extra work probably to do it that way.

Rob: And the reason that you wound up leaving the mastermind is you, Ruben, and I were like, I had HitTail and maybe was just starting Drip, no employees, Ruben had two contractors or three—I don’t know—two employees, and you were hiring your 20th employee. You were putting out culture and vision documents, trying to get everybody on the same page. We’re like, “Look, we like each other, we’re all ambitious,” but you’re just at a different place. That’s what wound up happening.

But during that time, I remember, that rewrite was not super fun. You just had a team of developers trying to rewrite it and then you had folks trying to add more features. You were basically building the parachute after you jumped out of the plane. I don’t know what there is to say about that, but do you remember that as being super painful? Because that was my memory of it. Or do you remember it as, “No, we handled it and we got it done”? I guess the fact that you rewrote it twice was the real brutal thing.

I remember when we talked about it, I was like, “Gosh, do not rewrite this code base.” Coming from a developer, my own perspective whenever I come into a new code base, I’m always like, “Oh, this is a whole piece of crap. I’m going to rewrite this whole thing,” and then I eventually resist the urge and I push the business forward instead. But you made a very, very hard decision to do that.

Jeff: Yeah, it’s funny you say that. I remember even when Chase joined, when he was thinking about joining, and he had done some diligence, we agreed like, “Hey, let’s not rewrite it.” I think even you said something like, “The first thing he’s going to want to do is rewrite it.” So, one of the things we talked about was, “Okay, let’s try to keep it as is and we’ll go with PHP.” I remember we hired a PHP dev and we hired someone else who was competent in PHP but also knew Django and Python as well. After a couple of months he’s like, “Dude, we got to rewrite this. I’m sorry. There’s too many issues with it.” Like you said, it was building the parachute on the way down or he used to say it was like changing the tires on the highway while you’re going 70 miles an hour.

At that time we had $20,000 a month maybe in customers, so we made $250,000 ARR maybe. Your customers don’t care if you’re rewriting it until it’s done. At the time, we might have had even T-Mobile or we were getting a customer like T-Mobile, so it was super stressful. Knowing that you’re building something that’s going to get ripped out eventually was way more stressful for them than it was for me.

As you know, anything technical always takes a lot longer than you hope and that probably happened, but what went well and what I learned from Chase—I knew even then—was he was super money when he recommended we do something. It always seemed like it was the right move. It was one of those things where he was like, “We have to do it,” and I said, “Okay, let’s do it.” It wasn’t what I wanted to do because obviously, it doesn’t feel like you’re moving forward.

We were rewriting it this year, too. We rewrote a lot of the front end, we rewrote some of the back end in terms of scalability, going from a few hundred thousand or a few thousand people on your site to millions of people on your site, the growth in terms of requests was insane. They were 10X-ing the site every year just to maintain it. It was pretty insane.

Rob: Yeah. I’ve been a part of one of those. Insane is the right way to describe it. So, you grew it. I remember in the early days you had a lot of focus on sales. You were doing a lot of one-on-one demos and that’s how you’ve landed, or one of the ways you’ve landed to customers like T-Mobile and these big enterprise deals. I was super impressed with that.

At a certain point, you and I lost touch for a year or two. I was doing Drip and you were really digging into growing Ambassador. When you sold the company in 2018, how big were you, guys? I don’t think you’ve been public with revenues so I won’t ask that, but employee count or some other indication?

Jeff: I’ll tell you a couple things. We were between $5 million and $10 million in revenue and about 40 some-odd employees, give or take.

Rob: What was the acquisition process like? Were you getting approached by people who wanted to buy you? Did you have to go out looking for interest? How long did it take? Talk me through. There are folks listening to this who don’t get to hear a lot of inside stories about these because a lot of them are so opaque. “It’s a TechCrunch post of X company sold for Y million dollars.” “Wow, isn’t that great?” and you feel like it happened in three days. The Drip acquisition from first email to close was 13 months, and 6 of that was me working 20 hours a week on it. It was incredibly stressful for me, so I loved if you can walk me through bits of it so people can hear what it’s like on the inside of something like this.

Jeff: Sure. It was definitely intense and it was probably close to, like you said, a year of planning total at least. For me, because we were funded, because we had a board, the first part of the process really came about through board discussions of, again, when you have a board, you always have to look at multiple years out. One of the things that we were doing was trying to figure out how can we get to where we want to be and what are the strategic options, and that includes either fundraising or essentially selling or buying somebody.

Once you raise money, you’re on the clock. So, the worst thing you can do is grow slowly or decelerate. Not say that it was happening, but I think it was a concern. We were kind of in-between a Series B, it was possible we could raise to B and that was one option. Then all the factors you have to think about if you raise a B between dilution, and lots of times people want new leadership teams. That was one path potentially and another path was, of course, selling. Another path was going to stay in the course, but having to figure out a way to accelerate growth instead of decelerating, which happens to most companies that usually don’t grow faster the year after.

We came up with the idea that we’d kick the tires and see if it made sense to explore strategic partnership which really usually means a sale, but it could have been different kinds of investments, too. We’re pretty open and we’d also looked at other types of alternative financing. So, we were looking at all options.

As I mentioned, money was getting lower than we had planned. Again, we were with 40, 50 people, we weren’t burning a lot, and some years, we were cash flow positive, but the swings with 40 people, payroll was several hundred thousand dollars a month. So, the swings are pretty big. You need to have enough cash-on-hand and again, relying on checks from companies and things like that.

That was going to begin the process. We didn’t end up hiring a banker, which basically was much more work from my perspective, for me personally, to get ready for working with a banker than working for fundraising. It was like putting a whole fundraising deck together but then including everything, even things that you would normally maybe not tell or you wouldn’t want to advertise, but you need to be really open about and just get everything together so that you can share everything, and that they know everything so that things go well and they give you an accurate idea of the value of the business.

When working with a banker, one of the things is the process. First, of course, they speak directly with the companies, companies are interested. Then they reach out to the team and they have what’s called a management meeting. We probably had a couple of dozen management meetings which are basically calls with the entire management team, giving them an overview of the business. It’s extremely stressful. For us, we had to do them and keep them private.

I like the idea that we were talking to potential acquirers, couldn’t be that obvious to the company. It was really stressful and we did probably a dozen or more of those. Some companies were some of the biggest companies that everyone’s heard of, some of them were known, private equity companies, and range across the gamut. We did that for several months and then eventually you get IOIs and LOIs. Eventually, once the LOI is signed, there’s a lot of work to do, you actually meet with all the folks, and try to really talk about get down to brass tacks in terms of integration and real items.

It was incredibly stressful. For me, I played a point person on most of the stuff. Obviously, the banker did a lot, I did a lot, it’s a lot more stressful than I anticipated, and it’s a lot harder, like a few times investors be like, “Why don’t just wait like two years and just sell?” I was like, “Man, it’s not as easy as it sounds,” but people always say that.

Rob: But you’re eight years in it at this point and it’s like, “This is eight years and it’s been really hard.” I imagine you might have been feeling some burnout. There’s a certain point where I feel like you start to hear that there’s an opportunity to not have to continue doing what you’re doing. I don’t get the feeling that you hated what you were doing. I think you were still into it, but at a certain point, you start to think about the next phase as well as, “When is this going to pay off? All this hard work, my whole life’s work, and my net worth is tied up in this company.”

Jeff: Yeah. That was one of the things where I felt bad because truly, my investors, some of them would have been excited if we would have kept going. The business was in a good spot. It wasn’t the best deal ever. We did well and generally, everyone was pretty happy, but it also wasn’t a no-brainer. You always hope for a no-brainer and everyone’s on the same page. The reality is, investors are smart. If something’s going well or something’s going good enough, they want to keep going. They’re only making so many bets or investments per year and if it’s working and there’s a pretty clear path to the next milestone, they don’t want to sell, which makes sense.

We got mixed feedback. Lots of people were happy. No one was mad, but people were like, “Hey, have you considered continuing on and going?” Like you said, Rob, I got to the point where it was so close, you could taste it, you see the outcome, and a lot of us have worked hard for it. They knew a year before that we were going to try to do this. It was one of those conversations that I had with them was like, “Guys, I know we’ve been working hard, but I need you to work twice as hard this year. Hopefully, they’re going to pay off and here’s all the incentives and reasons why we should do that.” I think everyone was pretty burnt. I think we were fried. As what we used to say, “We were totally fried. It was tough.” From that perspective, it was really hard to just walk away.

Knowing that, it obviously makes it a little bit more stressful because at any point in my time in Ambassador, I always felt like I had a lot of optionality where I didn’t need a specific outcome. This was one of those situations where I was like, “Alright, if we don’t sell here, we’re going to have to start looking to replace people because I don’t know if they’re going to be able to handle it.” That’s my analysis of it and, of course, we never got to that point. I’m really good friends with everybody, so if I would have also said, “We need you,” they would have stayed, but I just felt I would have been doing everyone a disservice by pushing. We pushed really hard for a long time.

Rob: I know the deal closed last October of 2018. When did you tell your employees and how did they react?

Jeff: We told them that day that we signed the deal. We had done all the diligence up into that point and had not told them. The reason for it was, based on everything that I heard, you really don’t want to tell people. I know that with big companies, with really big transactions or public companies, as soon as the LOI is signed, they tell the companies.

For us, we had the LOI signed a lot earlier. It wasn’t 100% that it was going to get done. That was just like in bigger companies, there’s a lot of shareholder pressure and things, like when you make the announcement, the expectation is that you’re going to close the deal. We had a lot of deal points that were not ironed out yet. Actually, multiple times during that period, I thought we might not close.

We told the team early October. I would say 95% of the people were super pumped. A lot of them were way more pumped when they heard what they would get out of it. I like to say that I prided myself on really trying to build a great culture, especially over the last couple years. Really, that was my main focus.

I think a few people were sad that, that might be happening and the uncertainty with an acquisition is scary for a lot of people. We were super transparent and we immediately had like a town hall Q&A. Everyone felt good after, but there were some things that we couldn’t control.

Right after closing that, I think West didn’t do very well and that got everybody unsettled again. Luckily, things went as smooth as they could have been. Behind the scenes, it was a lot of scratching, clawing, and tough conversations. I’m really proud for the leadership team and for what we did to hopefully make things work out as well as they did, but I think I’m very happy with how things turned out.

Rob: I know you’re someone who takes a lot of personal ownership over things, obviously, over your company but over the culture and over the well-being of your employees and such. The deal closes, you’re obviously relieved, probably pretty happy that went through. It’s a life-changing moment for you, but I know, as you just mentioned, over the next several weeks or whatever, a month or two, West maybe fumbled the ball a little bit and you weren’t in charge anymore. These weren’t things that you could fix. How did that impact you? Was it really hard to see it? Was it something that you knew would iron itself out so it didn’t stress you out that much?

Jeff: It was really hard actually. There were multiple times after the fact where I was like, “I wish we wouldn’t have done this, wouldn’t have sold.” A couple deal points weren’t fully fleshed out because West Corporate wasn’t able to disclose the particulars because they were still fluid. We agreed, “Okay, we won’t agree to this in terms of we won’t specifically memorialize it in the agreement,” and that ended up being a big mistake for me. I don’t want to say anything harmful, but what we got in that particular agreement was a lot worse than what we expected and it was again, to me, directly affecting the people and culture, and it really was a gut punch.

I did a couple of things that cemented my place with West probably and wrote some really aggressive emails and took some pretty aggressive stands that I hope paid off and set the tone for my team. Luckily, only a few people ever saw or heard it, but I felt good that I took a stand. I felt it was the right thing to do. Luckily, I know the folks who were going to stay there after me, I needed them to see that we need to stand up for the folks. Everyone was in agreement that we did.

Rob: Yeah, that comes back to that ownership piece, that’s what I was pointing at. That’s your personality. I figured you would do something like that. You mentioned that during that post-acquisition, you were struggling with it and that there were days where you regretted selling.

I guess I was lucky or whatever, I never woke up a single day after the Drip acquisition and thought, “I wish that we hadn’t done that.” It just worked out. There were some hard days, but it never made me think, “Oh, I would go back on this.” That tells me a lot. That tells me that it was hard, that it was really hard knowing you and knowing your psyche and ability to take stress and deal with it.

You were with West for about a month or two after the acquisition, really the first of the year, you were able to move on. It’s been seven-ish months, seven and a half months. Have you had any regrets since that point about selling?

Jeff: No, definitely not. A couple of things have changed those, I should add, the team, I would say, has worked really well with West. West just recently has put Ambassador in a position to be successful and that took a lot longer than we hoped it would, but even just as recent as last week, I still talked to a bunch of folks there, everyone’s doing well, I actually played in the softball team yesterday so it’s a lot of fun and everyone’s really excited, which is really great and that’s what we wanted to do.

West has really done a great job of correcting course and working with Chase, specifically, but other folks at Ambassador to try to continue to allow it to flourish and be successful. From what I’ve heard, things are going really well and people are happy.

Rob: That’s great to hear, man. It’s easy to have no regrets when it did work out in the end for your team. It worked out financially for you and several folks on your team, and then obviously life is substantially better for you at this point. I’m happy to hear that things are a lot better.

I think that leads us to our final question. Do you know what’s next for yourself yet or is that just something that you’ll wait and see? Because there’s no rush. That’s what I would tell you. Jeff, don’t rush into the next thing. There is no need to rush into the next thing.

Jeff: Yeah, I know. It’s funny. I’ve even told my wife, “Let’s be super intentional about what we do going forward,” because we’re fortunate enough to have that flexibility. I’ve tried to be really intentional. I’ve spent a good amount of time just advising, not formally, but I wrote a couple blog posts and just said, “Hey, if you’re in the area or you want to chat, I’m happy to talk.”

Rob: You’re a TinySeed mentor, thanks for that.

Jeff: Yeah, hopefully I can even do more but I’m excited to be on the Slack group, answer some questions, and be available for when it’s my turn to […] folks. I’m staying busy a little bit, looking to maybe do some lightweight consulting where I’m still keeping a lot of flexibility. I’ll be honest, I’ve talked to a couple of business brokers, just looked at what’s available, and tried to see what piques my interest.

I’ve floated out a couple of offers for companies that were maybe not the best offer for the founder. No one’s accepted anything yet, but I’m kicking the tires on a few things. But as we talked about earlier, my biggest concern is can I do it in a way that’s not all in and that allows me to be flexible? If I were to do something, I would really focus on that work-life integration or balance or whatever you want to call it where it’s much more flexible than the traditional company. I think that’s the future.

Rob: Thanks again, man, for coming on the show. I really appreciate you taking the time.

Jeff: Absolutely. It was great catching up again, Rob, and always good to chat.

Rob: If folks want to keep up with you online, where’s the best place to do that?

Jeff: Best place is probably Twitter, it’s @jeff_epstein. I’m on Medium also, but Twitter, I’m pretty active. If you tweet at me or DM me or something, I’m sure to see it and I can follow-up and chat from there.

Rob: Sounds great. Thanks again, man.

Jeff: Of course. Yeah, my pleasure.

Rob: Thanks so much for listening. As you can tell, I’ve been changing up the format over the past four or five episodes. Mike is on a temporary hiatus and an update on him, he took some time completely off. He was on vacation and he’s interested in coming on the show in the next few weeks to talk about his thoughts and his progress. So, we’ll hear from Mike soon.

In the meantime, if you have a question for me or one of my guest hosts, call our voicemail number at 1-888-801-9690 or email them to us at questions@startupsfortherestofus.com. Thank you for listening.

If you haven’t left a five-star review, would really appreciate it. If you liked the change-up in the format and the fresh voices, fresh perspective, even just the fresh show format, I’d really appreciate if you could lend a five-star review, even tweet out particular episodes that you’ve been impacted by. It really does help to show me that what I’m doing here matters.

I’m spending a lot more time on the show. I’m dedicating time to trying to raise the bar. If it doesn’t make a difference and I don’t hear anyone talking about it—I’ve heard two or three people compliment me on, that was super appreciated—if it doesn’t move the needle, then obviously, I have to invest my time in places where it really moves them forward. So, I would appreciate hearing your thoughts, sentiments on Twitter. You can email us directly, obviously, questions@startupsfortherestofus.com or five-star review always helps as well. I appreciate it and I’ll talk to you next time.