Episode 839 | The Journey Growing Help Scout to $35M ARR

Speaker A: Welcome back to another episode of Startups for the Rest of Us. I am your host, Rob Walling, and in this episode I have the pleasure of interviewing Nick Francis, the co founder of Help Scout. Help Scout has long been one of my favorite support tools. We used it back in the day at Drip and when Nick and I recently met in person for the first time, I uh, jumped at the chance to get him on the podcast. Nick is a bootstrapper at heart, but he and his co founders did raise money with Help Scout and they have grown it over 15 years to 35 million in ARR. It's a really interesting story with a lot of ups, downs and gutsy decisions. I think you're going to enjoy the conversation. Before we dive in, quick reminder that Microconf Europe is happening in Reykjavik, Iceland from September 21st through the 23rd of 2026. We have an incredible lineup of speakers, some great excursions planned, and obviously we're all looking forward to getting in the same room with about uh, 175 to 200 other like minded founders. Ticket prices go up on July 2nd, so they're the cheapest they will ever be. And if you're thinking about bringing your team or your mastermind group, we're running a group discount right now. If you buy three or more tickets, you get 10% off. Maybe your co founder or your CMO always wonders why you're so revved up after coming back for Microcomp. This is your chance to show them. Plus getting everyone in the same room is much, much more valuable than another Zoom, um, call and you'll be in Iceland. So that doesn't hurt either. Come up and say hi to me. If you wind up making it, you can head to microconf Europe.com to see the speaker lineup, get all the details and to grab your tickets before the price goes up. This event will sell out. So if you're thinking about going, go ahead and head to microconf europe.com and now let's dive into my conversation with N. Nick Francis. Welcome to the show.

Speaker B: So happy to be here, Rob.

Speaker A: Uh, it's great to have you, man. We ran into each other at microconf of all places in uh, Portland a couple months ago and you came up and I was like, nick Francis, this name is familiar. And you're like, I'm the co founder of Help Scout. And I was like, what? Like you guys are awesome. Like, I love Help Scout. A bunch of tiny C companies still use Help Scout. Bunch of people at microconp. I mean Drip back in the day, used Help Scout. It's really cool to have you.

Speaker B: Uh, I was so honored. It was great to show up at microconf and have such name recognition. Every time I talk to somebody, just like, oh, Help Scout. It was really, really nice. Yeah.

Speaker A: Yeah, that's cool. So we were chatting there, and I realized I wanted to get you involved, assuming you wanted to in this whole ecosystem we have. So you've since become a tiny seed mentor. Maybe teasing. Something we haven't announced yet, but let's just say loyal listeners. I, um, may or may not have invited Nick to speak at a future microconf, tell the story of Help Scout. And I wanted to have you on the show to really live through the story, to go back through the painful memories and the beautiful ones as well of the past, what, 15 years, I guess, of Help Scout.

Speaker B: Yeah, 15 years. But I'm such a big fan of what you are doing, the community that you've built. Microconf has been a force of nature for so long. It was really great to be there with people. It's with kindred spirits, people with shared values. I think that's a really special event.

Speaker A: Thank you. Appreciate that. It's definitely your people, right? You're like, uh, basic. I think of you as a founder who has that opinionated taste that I admire, like Ben Chestnut of mailchimp, the Basecamp guys, these other founders who really even, um, Postmark Natalie and Chris.

Speaker B: Yeah, they're legends.

Speaker A: Yeah. Yeah. Wild bit, right? And it's this opinionated take on. I don't just want to build a company, but I want to do it in a certain way that I believe in. And for you, that was. I, uh, think of you mostly as a bootstrapper. I think of, like, Jason Cohen, to be honest, mostly as a bootstrapper. Even though he's raised a kajillion dollars, he just has that mentality. He thinks like a capital efficient. And you're one of the same. Even though, as we're going to get to in your story, you raised $28 million in funding. So I just want to. I just want to start that off. Like, as people are listening, it's like you are that Bootstrap founder who has now gone down this path. And I kind of want to hear about your thought process along the way. I think to kick us off, I have a nice little timeline here that producer Ron put together for me. And all the way back In April of 2011, you launched out of Techstars Boston. And is it true their terms were $18,000 for 6% of your company. I want to, I'm going to change the tiny seed terms. I want to buy companies at that valuation. Holy moly.

Speaker B: I know, Wasn't that wild? Uh, and this was before techstars was doing a convertible note. And like all this additional capital, back in the day, startup accelerators were much more profitable. It was truly. They gave us $18,000 and that was literally like the money that we lived on for the next three months. Like we shared an apartment. I slept two feet from one of my co founders for three straight months just grinding and trying to build that product and bring it to life. And so 18 grand. And we ended up, uh, returning about two and a half million dollars on that investment.

Speaker A: Wow, that's a nice little lift for them. And so you had this idea of a shared email in that was invisible to customers. Right. No portals or ticket numbers. And in fact, I want to take just ah, a moment and read your H1 today. H1 is businesses that run on relationships run support on help Scout. Does that still land?

Speaker B: I didn't write that one.

Speaker A: I was going to ask you, does that. That seems like that's a headline, but tell me about the original vision. Was no one else doing this? Because this sounds obvious now, but I don't know that anyone had done this. Right. Because it was like Zendesk and a bunch of crap. Crap. I say my words.

Speaker B: That's basically the case. Yeah, we had spent, uh. So I'd been working with my co founders for six years and we had done the playbook that so many successful bootstrap companies had done at that time. We start by doing client work and building things for clients. And then on the side we start to build products. Right. So we work on our craft and learn to build things for the web and try to get paid for it. And then on the side we're like grinding away on software products. And so the dream was always to do that. And so we had spent six years building together. And one of the products that we had built didn't make a lot of money, but it actually got a lot of traction. I had like 200,000 active users, this little product that we built, and it was enough such that we had a customer support problem. And so I wasted two weekends trying to set up Zendesk. I just thought it was far too complicated for the business that we were trying to run. I tried a bunch of other products. I actually ended up thinking about this space for a couple of years. For some reason I was Just obsessed with this particular set of problems and doing customer support. And I just felt like, man, there's gotta be a better way to do it. And basically I just wanted to remove the system in the middle, right? Ah, a lot of ticketing systems or customer support systems always had this system in the middle that was assigning a ticket number and basically removing all of the humanity from, from that interaction. And I'm like, man, I know that the technology exists so that we don't actually have to have all this system in the middle like and remove the humanity. We can make it just like every customer support email is like you're getting an email from a friend. There doesn't need to be a ticket number, there doesn't need to be all of this cruft. And so we just decided to remove that and also build a product that added this really light collaborative layer on top of email. That was the goal is like email is really not built for teams. I think that you could add this collaborative layer on top and it would be an extraordinary tool not just for customer support, but for all these other really interesting use cases. And so we did design and architect it for use cases well beyond customer support, which ended up being a very good move for the business.

Speaker A: People often wonder how a tool like this that becomes uh, an 8 figure ARR SaaS company, how it starts, like what those early days are like. And I'm wondering if you remember, do you remember how you got your first 50 customers? Were you doing content marketing outreach?

Speaker B: The way I describe our time at uh, techstars is that we knew how to build what we believed to be a great product, but we had no idea how to build a software business. And so techstars was really that process of three months grinding away, learning how to build a software business. And so what that meant for us in terms of initial traction is one, we were obviously using the heck out of our own product. But we techstars actually operated in a space in Cambridge, Massachusetts called Dogpatch Labs. And at the time this was like a big sort of incubator space. So there were literally like 30 ideal customers in the same space. All these people trying to build companies. And so I would literally just walk around with my laptop. I would be that guy that sort of tapped you on the shoulder and was like, hey, what are you guys doing for customer support? Would you be interested in answering a few questions? Can I show you the product that we're building? Would you be interested in trying it? If so, like, I'm right over there. If you have any questions. And that was sort of how we got started. So our first customers were not only some of our colleagues in techstars, but they were people that were in this broader office space that we were in. And I, uh, got to learn a lot from those folks. And something else that we did was every time somebody signed up, we would require a phone number. And I would call every single sign up just to understand I wasn't there to sell. I was actually just there to be like, why did you sign up? What problem were you trying to solve? Just some really high level questions that really helped us understand our ICP early and often. And so that was really, the early phase was just trying to be extremely close to the customer and the problems that they were trying to solve so that we could start to finish their sentences and design a product that met those needs.

Speaker A: And you had two other co founders. So there are three of you total. What was your role?

Speaker B: Yeah, so, uh, Denny is an extraordinary engineer and Jared is an extraordinary designer. And so I sort of sat between them. I guess you would call me the product person. I'm passionate about the brand and the go to market as well. I grew up coding, and so Jared didn't know how to code at the time. Today he's a way better coder than me, but I was coding the front end and building a lot of the, uh, components. But Jared was really responsible for a lot of the design and user experience. So that's kind of how it all fit together.

Speaker A: And just to cut to the end of where Help Scout is today, you stepped down as CEO about eight months ago, I guess late 2025, and became chairman of the board. And can you talk about where the business is at in terms of revenue or where it was at that time?

Speaker B: Yeah, today it's well north of 35 million in revenue. So we're really proud of what we achieved over the course of those 15 years. It was, it was always, every day was always harder than the last, but I enjoyed every minute of it. Uh, absolutely, building that business. And I still think there's a lot of really great things to come for the company.

Speaker A: And I want to touch on that a little later. I want to get into raising funding, which maybe, maybe is the next topic as well, is like as a mostly kind of bootstrapper at heart, which I think we have a quote in this. You, uh, announced on Medium In March of 2015, I'm a bootstrapper at heart. But you, you raised a $12 million Series A from Foundry Group. That is a very large amount of money. What was your thought process there? You know, what made you decide to raise?

Speaker B: I actually want your take on this too, because we were building horizontal SaaS at the exact same time, right? You were building Drip, we were building Help Scout. And I remember having a conversation with you at microconf where you were just like, man, it was such a, uh, grind trying to reach that next level of growth. I just never felt like I could fully capture the opportun. And I felt exactly the same way. Right? The company was growing like gangbusters. We were profitable. Took us about 18 months before we were profitable. But then we sort of maintained a sort of ramen profitable business where we were just hiring as fast as we could, deploying all the profits as fast as we could to try to keep growing the business. And about four years in, I had a friend that had taken money from Foundry Group. So Foundry is based here in Boulder. Brad Feld is an absolute legend. Their firm is absolutely legendary, uh, in so many ways. And I just felt a sort of alignment with the way that they operated. They were not hands on. They were pure capital. Gave founders a lot of freedom and respect. And so Foundry Group just felt like, you know, if we were going to go chase a much bigger opportunity, which is effectively what we were signing on to, it was like, hey, man, like, is there potential for this to be $100 million business? If we think there is, then we owe it to the business. Even if that's not my sort of default, uh, operating model or default operating mode is raising money. If I feel like the business, if the business's potential Is to be $100 million plus business, then I have to lean in, even if it feels uncomfortable. And so that was sort of the calculus is, look, we were, we were in a good place as a company, but we were really able to take the company to another level. And I think between 2015 and 2018, we like, 3x'd the company. And so, uh, we were certainly able to put that capital to good use.

Speaker A: The bootstrapping purists who are like, never raise money and all funding is evil and all venture capitalists are evil. I've never liked that tone. I think that, uh, the extreme on either side of I should always bootstrap or I should always raise money, I think both of those are unhelpful opinions because they don't give the nuance of what money can do for you as long as you know what strings are attached, what that, what game you're playing now. Because if you raise 12 million bucks, you're not playing the same game that you were six months earlier. You know, the exit valuation, all of that you went on over the course of the next several years to raise a total. I have 28 million is what I have listed down. And at a certain point, I think it was 2021, I have a note that you were, you had an opportunity to actually de risk financially and to explain to folks what that means is you can sometimes take secondary out. You sell your shares, a founder such that of a $15 million round. A portion of that goes to the co founders. They actually just sell some of their equity. But my question for you is you raise a lot of money. The business is doing well. Would you do it differently? If you could go back, would you still raise? Would you raise as much?

Speaker B: I would do it differently. That's kind of hard for me to say because along the way we did business with extraordinary investors. I actually have no complaints with the investors that we worked with, with what I, to use your words, signed up for, because I absolutely signed up for that journey. But now that I've seen that side of it, now that I kind of leaned into the discomfort and I got an understanding of what it is to run a business like that where like there's never an amount of growth that's enough. Right. If you double the business, you look up, I got to double the business again. Right. I uh, mean, you just. The growth expectation is. And I was really trying to do my best to lean into the tension between trying to craft something really beautiful because I'm not really motivated by the size of the revenue number. I think of success in a much broader sense. But investors don't.

Speaker A: Right.

Speaker B: It's not actually their money that they're deploying. Right. They have a job to do. And I was trying to lean into that tension and I thought that it would bring out my best and the company's best. And I think in many ways that it did. But for me personally, looking back now on a 15 year journey, yeah, I would have done it differently. I wouldn't have raised money.

Speaker A: That's crazy. So just the early hard days of bootstrapping, you would have just grounded out and kept doing it.

Speaker B: Sometimes I look around and I sort of laugh to m myself. I'm like, damn those 37signals people. Damn Jason and David. They were always right about this stuff. You know, as much as I wanted to stress test, you know, and really push against their way of thinking about this, that we've all been Inspired by over the years. I just think that they had it right. And I still think that.

Speaker A: We'll get back to the conversation in a minute. If you're running a B2B SaaS company doing between 2 and 25 million of ARR, you've probably had some buyers show up in your inbox. Maybe a private equity firm, maybe a competitor, maybe some random aggregator. And the questions are always the Is this a real offer? Is it any good? Should I even respond? Here's the thing. The buyers who cold email you are not the ones who are going to pay top dollar. They're hoping you don't know any better. Discretion Capital exists to fix that. Einar Volsett runs Discretion. He's also my co founder at tinyseed. They have a proven system for finding the right buyers and maximizing exits. If you want to know what your company is actually worth, not just what someone is willing to lowball you, head to discretioncapital.com and book a call. And something that you mentioned right before we hit record that I had forgotten about. I said at Drip, we were Help Scout users because I loved the tool. And you reminded me that Help Scout was a Drip customer, like one of our early biggest customers. Absolutely. You backed up our queue and maybe took us down once or twice with a big send. Uh, it was impressive.

Speaker B: Yes. Dude. I was so psyched about Drip because it's a very similar thing. Like when you're in this massive space with a lot of products that are way too complicated and they're not really focused on the user experience, that's what you're focused on. With Drip, you actually built a wonderful product. It was really good to use, reliable. And I just instantly connected with Drip myself because I was the one that signed up and started to use it. And I just felt like what Help Scout is in customer support. Drip was in email marketing.

Speaker A: Uh, that's a big compliment.

Speaker B: Yeah. And I just felt like that we were kindred spirits in that way. And I took a lot of joy in breaking your tool so you guys could make it better.

Speaker A: Totally. And you broke it all the time with your big list. And shout out to Derek Reimer, my co founder with Drip, because he was far ahead of me in terms of UX and design. And the reason if it felt very elegant to you and like it met your standards, which are very high, I'm sure, of design taste. That was Derek. He and I ran product together and decided what to build, but his fingerprints were all over the elegance of that. And he runs Savvycal these days, which is.

Speaker B: I'm a happy customer of Savvycal.

Speaker A: Okay. And isn't the UX really elegant? You know, it's that whole.

Speaker B: It's outstanding. It's one of those things where like, yeah, there's 100 tools. I don't care. That's the best one.

Speaker A: Ah. Uh, that's great. What a testimonial. I wanna ask you about this Public Benefit Corporation, and I have the note. In 2018, Health Scout converted to a Public Benefit Corporation and eventually earned a B Corp certification. I have never heard of a SaaS company doing that, especially not a funded SaaS company. What is the story there? Maybe you can start by explaining a lot of people won't know what those terms mean. Define them, and then talk about why you made that decision.

Speaker B: So, uh, Eric Rees just came out with a book called Incorruptible that's about all of these kind of concepts. And he says it so much better than I do. But as a founder, you often don't realize what you're signing up for when you start a corporation in America. Right? You don't really realize that, uh, corporations are legally designed to serve only the shareholder. There's no other stakeholder. So that we talk about a broad definition of success that I have. Legally, corporations don't have a broad definition of success. Shareholder value is the only thing that matters. And that's always felt incongruent with my personal values and the values that we espouse as a company. And so, believe it or not, I got to give, uh, our friends at Foundry Group a lot of credit here. Our investor sent us a book on Public benefit corporations. They sent every CEO a book on what a Public Benefit Corporation was. And like this, this whole handbook, I think it was the B Corp handbook back in the day. So it was before Public Benefit Corps were a thing, but it was like the B Corp certification thing. And I just. I read it, I loved it. And basically, the concept behind a Public Benefit Corporation today, instead of a C Corp, it's a. It's a PB Corp. And you can do it in Delaware just like you would do a C Corp. And effectively it just says, hey, instead of there being one stakeholder, the shareholder that you serve, that you exist to make happy, then there's a variety of stakeholders. There's customers, there's employees, there's the broader community at large, and there's also shareholders. I just think that that better aligns with who we are. Right? Like, we don't just care about shareholder value. We care about other aspects of the business as well. And we think that in the long term, those interests and those stakeholders serve shareholders. So we decided. Yeah, and I just, you know, we were very early on remote work. So we were, we founded the company fully remote in 2011 when people thought we were crazy. I'm used to doing things that sort of go against the grain, and being a public benefit corporation, specifically as a software company, was just another way for us to differentiate and make a statement as a brand about who we wanted to be to our customers, to our employees, to the broader community. And so we went through that process and, uh, I gotta give the folks at Foundry credit because they were very cool with it. So our investors were very cool with it, helped us kind of sign the paperwork and, uh, ensure that we could get B Corp certified, which is like the next level. So think of a B Corp certification similar to, like, if you have a food company and you want to get fair trade or organic certified, this is that for a business. And, uh, so we went through that B Corp certification as well, which was really interesting. So some of the first ones were like Patagonia and Ben and Jerry's and like all these companies that we've admired for a really long time. I'm like, well, why aren't there any software companies here? I think I want to be one of the first.

Speaker A: Uh, that's a cool story I like. And it really does feel like aligned with your values, you know, and who you are. I want to ask you about AI. And as AI came out, ChatGPT and everyone's talking about how you have to integrate it into your product and then how you. It must be this, and then it's going to kill SaaS and all this stuff. When you were inside help Scout in 2022, 3 and 4, as you're thinking, like, everyone's asking you, what's your AI strategy? Right. Uh, investors, I'm sure, customers, I'm sure the internal. Your team members. What was your approach? How did you use AI? Uh, there's a couple obvious ones. Right. I want AI to scan through stuff and, uh, create a first draft of the ticket response so that I can. Did you do that? Did you do more than that? Just talk me through how that played out.

Speaker B: Yeah. So before LLMs were a thing, there were several AI hype cycles in customer support. Customer support is traditionally seen as a cost center. And for that reason, there's a lot of people that have tried to build tools that make it so that you don't have to have as many humans involved, because humans are the biggest expense in that cost center. And so look back in 2017, there were AI chatbots, right? But they were built on these like machine learning models where we actually did the math. We investigated these tools, we tried to build some of these chatbots, and we realized they were really poor customer experience. And ultimately like less than 5% of our customers had enough data to really like for a machine learning model to even be useful to them. And so it wasn't the right time for us. So when LLMs came along, I was psyched. I mean, Rob, you and I are builders, right? Like we love to build software. And for that reason I was psyched about these new tools because I've never had so much fun building in my life. I had no idea what was to come. But basically when we first learned about ChatGPT, which I think was in late 2022, we did a hackathon much like a lot of other companies, just to explore these tools and see what was possible. And so right away we built a tool to summarize conversations, we built a tool to, to draft responses. And then we ended up making an acquisition along those lines. But we built like six things over the course of two weeks. We had a little working group and I was in the details, uh, working on these products myself as well. And we had a lot of fun building with those tools. And I think that that was sort of the beginning of, you know, what became our AI roadmap. But I think of AI as a tool. It's not necessarily like at the end of the day, we design our products for the optimal customer experience. So not our customer, their customer. We optimize for the user at the end of it, like what is the best possible experience we can create for them. And so that's actually a different perspective. I don't think any of our competitors actually think that way. We are optimizing for your customers experience at the end of the day. And so that perspective on this allowed us to do a lot of building and have a lot of fun with it. But, but the outputs looked different, uh, and I still think that they do today. So we're always going to make a human more available in our tools than pretty much any of our competitors. And we take a lot of pride in that because there's a lot of companies out there that, especially small businesses, which is what I'm so passionate about, that look, they win on better customer experience, maybe they can't win on features, maybe they can't win on the Most funding or whatever it might be, but they can win on a better customer experience. And that makes your brand what it is. That's your most effective marketing. Right. Is a great customer experience. And so if we can help our customers deliver that, then I think it's worth more than the price of admission.

Speaker A: I have a note about a, uh, pricing overhaul in November of 2020. Four of you guys moving from per seat to per contact. That feels like a really bold, like a big move after 13 years with thousands of customers. And then you're like, we're going to do it by contact. Talk me through. Were you the first to think about this? Had other competitors done it, why you made that switch and if it worked or not.

Speaker B: We were always thinking about pricing and packaging. From I'd say 2017 on. We had a team and I was on that team of people that were always thinking about pricing and packaging, always optimizing and testing and uh, moving the ball forward with regard to that aspect of our strategy. And so very early on with these tools, as I mentioned, we were building a lot with AI, we realized, wow, like we're going to be able to create a lot of value for our customer that doesn't tie back to a seat. And generally you could sort of see like, hey, if you Fast forward this 10 years, my sense is that a lot of businesses that are per seat today are not really going to make a lot of sense per seat tomorrow. I felt like, if you've read any Clayton Christensen, like, I felt like we were about to live an innovator's dilemma where the incumbents were going to be. There was new technology coming in. The incumbents were going to be at a strategic disadvantage. They weren't going to adopt this new technology fast enough. And there was going to be an opportunity for a little guy like help scout still, like, yes, you could say like tens of millions in revenue, but we're actually still the little guy. There's an opportunity for us to outmaneuver the competition. And so I felt like it was, yes, it was a massive swing, but I felt like customer support is moving away from seat based pricing. It's just not the correct value metric anymore. So we did a bunch of research, but at the time it was just like, there's no research that's going to tell you to do something this crazy. So we did the research, we saw all the data points, we talked to all the people and at the end of the day I made a call to test it and just say, look, we have to test A fully usage based pricing model. And for us that meant pricing per contact. So if somebody reached out five times over the course of a month, we just charge for that one contact. And so one thing that we noticed in our pricing research is that people have various definitions of what an AI resolution is. So the way Intercom, for instance defines an AI resolution is not the way 98% of the market actually defines an AI resolution. And so it's like what if you just didn't even have to worry about an AI resolution? Because uh, I think that's kind of um, a, it's a funky metric. Like the person could literally reach out via email the next day and uh, that's not an AI, that's not resolved. So we felt like a contact was a really clean way to capture value but not have to worry about all the semantics and details. It wasn't going to be that complicated. And contacts are a very familiar metric, at least in other industries, like the one drip was in. And so we felt like it was generally acceptable, like people would understand it. And so we tested and we iterated on three different variations of pricing and packaging over the course of 12 months. Long story short, it wasn't there. Even when this new usage based business model would benefit a customer, even when they would pay less, they just didn't want to do it. So there's a perception that people have more control over their costs when they pay per seat. And yeah, technically they do. The problem is that our pricing per contact was actually 30% less variable than per seat. It was actually more consistent, more predictable. But that's not the way that people saw it. They just, you know, they saw the status quo and the way that people bought this software and they wanted to do it that way. And so we ended up landing on a hybrid, which is kind of where the whole market has now landed, which is seats plus you pay for AI resolutions, which is what we wanted to avoid. But I think that's what the market clearly told us they wanted to do. So in summary, I would say we were too early. I still think that somebody's going to come along with a highly disruptive pricing model because look, the secret of SaaS, uh, per seat SaaS particularly is that 20% of those seats shouldn't be paying for anything because they're not even using the tool. Right. And so I wanted to go directly at that margin and try to win it against our competitors. And you know, if there's just not willingness to accept that business model, then I have to live to fight Another day.

Speaker A: What a bold move. I mean, these are the types of big swings that you take that if they turn asymmetric upside, right? If they work, they're a huge business changing event. And if they don't, it's probably pretty painful along the way. Was it brutal? Like, was it tough?

Speaker B: Absolutely, yeah. Uh, well, at the end of the day, I feel like I just lost confidence from some of our stakeholders that ended up being like, hey, I'm not the guy to lead the company anymore. I mean, that's really kind of what led to it. And I have no regrets. I'm an entrepreneur. I was built to make these kinds of swings. And in terms of leaning into that tension, we raised $28 million, as you mentioned. Like, I'm trying to build $100 million plus company here, right, when all of my competitors have raised 10 times the amount of. So I've got to do something different and really lean into that tension and that discomfort of the pressure of growth and say, well, hey, if I got to grow, I'm going to swing for the fences, because that's what this model is all about. And so had we been bootstrapped at the time, maybe a $20 million business, we wouldn't have made that move. But when you accept that kind of capital, you're swinging for the fences. And I felt like we had to at least try it. And so for eight, nine months, we tried it, and we ended up pivoting away from it. But that's what I'm an entrepreneur. That's what I'm built to do.

Speaker A: And then, you know, you already mentioned it. In late 2025, you stepped down as CEO. You became the chairman of the board. It sounds like it was time. I mean, is that it? I was going to say, why, you know, why did you decide to leave that role?

Speaker B: You know, upon reflection, I was having a really tough time leaning into that tension and trying to thread the needle between being a bootstrapper at heart, really being committed to building products in a certain way and operating businesses in a certain way and delivering on an outcome that would make my stakeholders very happy, right? So, like, trying to thread that needle for 15 years, really, like 11 years funded, was incredibly challenging for me and draining. And so I sort of picked my head up and I said, what if I'm just not the guy anymore, right? Like, what if the journey from 40 million to 100 million is just somebody else? And when I asked myself that question, I'll be honest with you, Rob, A, uh, weight lifted. And I was like, Whoa. Well, then that would enable me to actually go do what feels true to me as an entrepreneur. Just no compromise, no tensions. Like what feels absolutely true to my core and my values. I still have another rep in me. I still have more time to build one more thing. Like, this is the opportunity to go build that thing and not have any of those tensions. I've experienced it. I've seen that side of it. I'm not doing that again. So I really felt like it was just the right time.

Speaker A: I was going to ask, what do you do? You got another startup in you? Have you started working on it? Is it in stealth mode still?

Speaker B: Yeah, I am working on something. The weird thing about what I'm working on is that, uh, it's not necessarily like, something I can just put my head down and build. So I can't talk about it yet. Not because I'm holding any secrets. It's because I haven't figured it out. But I have been working really hard. I've got all the energy in the world. I feel like, as an entrepreneur, I still have unfinished business. I can promise you this, Rob, it's going to be bootstrapped. No institutional capital.

Speaker A: What a great end to that story, man. Um, I'm excited to see what you build next. And if folks want to keep up with you on the Internet, your H1 is I help founders become exceptional CEOs. So you're now help coaching entrepreneurs and founders?

Speaker B: Yeah, I will say, like, uh, one of the absolute joys of stepping away from the company and having an opportunity to just kind of pick my head up has been like, oh, wait, I have all this experience and I have all these things that I've learned over the years. It's time for me to put on the other hat that so many, you know, so many people have kind of given me their wisdom and advice over the years. And so I've started to work with some founders, I've started to work with other CEOs. I've built a CEO group that's, uh, that I'm really excited about. So I spend maybe a quarter of my time just trying to help other founders. And I just absolutely love that work, but I'm not ready to do it full time. I still want to be an entrepreneur, too.

Speaker A: And if folks want to reach out to you, um, they can go to nickfranc Is. So it's Nick Francis, but with a dot before the is.

Speaker B: A is. Yeah, that's the Icelandic, uh, domain, I think.

Speaker A: Is that what it is? Icelandic?

Speaker B: Yeah.

Speaker A: And they can read your writings. Uh, you have a get in touch link and about more of what you're up to. Thanks so much for coming on the show, man. It's been really great having you.

Speaker B: Oh, it's my pleasure buddy. Good to see you.

Speaker A: Thanks again to Nick for joining me on the show this week. And Nick is doing a great job giving back to entrepreneurs. He's ahead of so many folks and has so many learnings from his journey and I just really appreciate his earnest sharing and his willingness to give back to the microconf and tiny seed ecosystem. Thank you for listening this week and every week. This is Rob Walling signing off from episode 839. Sam.