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

Rob Walling: 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 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, a quick reminder that MicroConf Europe is happening in Reykjavik, Iceland from September 21st through the 23rd of 2026. 

Rob Walling: 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 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 from MicroConf. This is your chance to show them. Plus, getting everyone in the same room is much, much more valuable than another Zoom 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.com/europe 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.com/europe. And now let’s dive into my conversation with Nick. Nick Francis, welcome to the show. 

Nick Francis: So happy to be here, Rob. 

Rob Walling: It’s great to have you, man. We ran into each other at MicroConf of all places in 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? You guys are awesome. I love Help Scout. A bunch of TinySeed companies still use Help Scout, a bunch of people at MicroConf. I mean, Drip back in the day used Help Scout. It is really cool to have you. 

Nick Francis: I was so honored. It was great to show up at MicroConf and have such name recognition. Every time I talked to somebody it was just like, oh, Help Scout. It was really, really nice. 

Rob Walling: 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 TinySeed mentor, maybe teasing something we haven’t announced yet, but let’s just say loyal listeners, I 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? 

Nick Francis: 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. 

Rob Walling: Thank you. Appreciate that. It’s definitely your people, right? I think of you as a founder who has that opinionated taste that I admire. Ben Chestnut of Mailchimp, the Basecamp guys, these other founders who really, even Postmark — 

Nick Francis: Natalie and Chris. Yeah, they’re legends. 

Rob Walling: Wild Bit, right? 

Nick Francis: Yes. 

Rob Walling: 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 think of you mostly as a bootstrapper. I think of Jason Cohen, to be honest, mostly as a bootstrapper, even though he has raised a cajillion dollars, he just has that mentality. He thinks 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. I just want to start that off. 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’m going to change the TinySeed terms. I want to buy companies at that valuation. Holy moly. 

Nick Francis: I know. Wasn’t that wild? And this was before Techstars was doing a convertible note and 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 the money that we lived on for the next three months. 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 $18K, and we ended up returning about two and a half million dollars on that investment. 

Rob Walling: Wow, that’s a nice little lift for them. And so you had this idea of a shared email inbox that was invisible to customers, right? No portals or ticket numbers. And in fact, I want to take just a moment and read your H1 today: “Businesses that run on relationships run support on Help Scout.” Does that still land? Tell me about the original vision. Was no one else doing this? This sounds obvious now, but I don’t know that anyone had done this, right? It was like Zendesk and a bunch of — sorry, my words. 

Nick Francis: That’s basically the case. Yeah, 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. 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 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. It had like 200,000 active users, this little product that we built, and it was enough such that we had a customer support problem. 

Nick Francis: 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 around doing customer support, and I just felt like, man, there’s got to be a better way to do it. And basically I just wanted to remove the system in the middle. 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 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 and remove the humanity. 

Nick Francis: We can make it so that 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: 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. 

Rob Walling: People often wonder how a tool like this that becomes an eight-figure ARR SaaS company, how it starts, 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? 

Nick Francis: The way I describe our time at 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 Techstars actually operated in a space in Cambridge, Massachusetts called Dogpatch Labs. And at the time, this was a big incubator space, so there were literally 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? 

Nick Francis: 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, 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 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 signup 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: 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. 

Rob Walling: And you had two other co-founders, so there are three of you total. What was your role? 

Nick Francis: Yeah, so Denny is an extraordinary engineer and Jared is an extraordinary designer. And so I 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 I was coding the front end and building a lot of the components, but Jared was really responsible for a lot of the design and user experience. Jared didn’t know how to code at the time. Today he’s a way better coder than me. So that’s kind of how it all fit together. 

Rob Walling: 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? 

Nick Francis: 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. Every day was always harder than the last, but I enjoyed every minute of it, absolutely building that business. And I still think there’s a lot of really great things to come for the company. 

Rob Walling: And I want to touch on that a little later. I want to get into raising funding, which maybe is the next topic as well. As a mostly bootstrapper at heart, which I think we have a quote on: you announced on Medium in March of 2015, “I’m a bootstrapper at heart,” but you raised a $12 million Series A from Foundry Group. That is a very large amount of money. What was your thought process there? What made you decide to raise? 

Nick Francis: I actually want your take on this too, because we were building horizontal SaaS at the exact same time 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 grind trying to reach that next level of growth. I just never felt like I could fully capture the opportunity. And I felt exactly the same way. The company was growing like gangbusters. We were profitable. It took us about 18 months before we were profitable, but then we sort of maintained a 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, based here in Boulder. 

Nick Francis: Brad Feld is an absolute legend. Their firm is absolutely legendary 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, if we were going to go chase a much bigger opportunity, which is effectively what we were signing onto, it was like, hey man, is there potential for this to be a hundred-million-dollar business? If we think there is, then we owe it to the business. Even if that’s not my default operating model or default operating mode, raising money — if I feel like the business’s potential is to be a hundred-million-dollar-plus business, then I have to lean in even if it feels uncomfortable. So that was the calculus: look, we were in a good place as a company, but we were really able to take the company to another level. I think between 2015 and 2018, we 3x’d the company. We were certainly able to put that capital to good use. 

Rob Walling: 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 the extreme on either side, I should always bootstrap, 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 game you’re playing. Now, if you raise $12 million bucks, you’re not playing the same game that you were six months earlier. The exit valuation, all of that. You went on over the course of the next several years to raise total, I have $28 million is what I have listed. And at a certain point, I think it was 2021, I have a note that you had an opportunity to actually de-risk financially. To explain to folks what that means: you can sometimes take secondary out, you sell your shares as 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? 

Nick Francis: 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. 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 leaned into the discomfort and I got an understanding of what it is to run a business like that, where there’s never an amount of growth that’s enough. If you double the business, you look up, I got to double the business again. I mean, 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. 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, right? It’s not actually their money that they’re deploying. 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, I would’ve done it differently. I wouldn’t have raised money. 

Rob Walling: That’s crazy. So just the early hard days of bootstrapping, you would’ve just ground it out and kept doing it? 

Nick Francis: Sometimes I look around and I sort of laugh to myself. I’m like, damn, those 37 Signals people, damn, Jason and David, they were always right about this stuff. As much as I wanted to stress test 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. 

Rob Walling: We’ll get back to the conversation in a minute. If you’re running a B2B SaaS company doing between two 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 same. 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. In Einar Vollset runs Discretion Capital, 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. I loved the tool, and you reminded me that Help Scout was a Drip customer, one of our early biggest customers. 

Nick Francis: Absolutely. 

Rob Walling: You backed up our queue and maybe took us down once or twice with a big send. It’s impressive. 

Nick Francis: Yes, dude, I was so psyched about Drip because it’s a very similar thing: 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. 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. 

Rob Walling: That’s a big compliment. 

Nick Francis: And I just felt like 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. 

Rob Walling: Totally. You broke it all the time with your big list. And shout out to Derrick 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 it met your standards, which are very high, I’m sure, of design taste, that was Derrick. 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 — 

Nick Francis: I’m a happy customer of SavvyCal. 

Rob Walling: Okay, and isn’t the UX really elegant? It’s that whole — 

Nick Francis: It’s outstanding. It’s one of those things where, yeah, there’s a hundred tools. I don’t care. That’s the best one. 

Rob Walling: Ah, that’s great. What a testimonial. I want to ask you about this public benefit corporation, and I have the note: in 2018, Help 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. 

Nick Francis: So Eric Ries just came out with a book called Incorruptible that’s about all of these kinds 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. You don’t really realize that corporations are legally designed to serve only the shareholder. There are no other stakeholders. So when 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 our friends at Foundry Group a lot of credit here. Our investors sent every CEO a book on what a public benefit corporation was. 

Nick Francis: It was the B Corp handbook, back in the day before public benefit corps were a thing, and I read it, I loved it. And basically the concept behind a public benefit corporation today: instead of a C Corp, it’s a PBC, 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 and that you exist to make happy, 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. 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. 

Nick Francis: So we decided, and we were very early on remote work, so 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 I got to give the folks at Foundry credit because they were very cool with it. Our investors were very cool with it. It helped us kind of sign the paperwork and ensure that we could get B Corp certified, which is the next level. So think of a B Corp certification similar to if you have a food company and you want to get fair trade or organic certified. This is that for a business. And so we went through that B Corp certification as well, which was really interesting. Some of the first ones were Patagonia and Ben and Jerry’s and all these companies that we’ve admired for a really long time. And I’m like, well, why aren’t there any software companies here? I think I want to be one of the first. 

Rob Walling: That’s a cool story and it really does feel aligned with your values and who you are. I want to ask you about AI. As AI came out, ChatGPT and everyone’s talking about how you have to integrate it into your product, and then how it must be this, and then it’s going to kill SaaS and all this stuff. When you were inside Help Scout in 2022, 2023, and 2024, as you’re thinking, everyone’s asking you, what’s your AI strategy? Investors, I’m sure, customers, I’m sure, and internally, your team members. What was your approach? How did you use AI? There are a couple obvious ones, right? I want AI to scan through stuff and create a first draft of the ticket response. Did you do that? Did you do more than that? Just talk me through how that played out. 

Nick Francis: 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 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 less than 5% of our customers had enough data 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. 

Nick Francis: I mean, Rob, you and I are builders, right? 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 draft responses, and then we ended up making an acquisition along those lines. But we built six things over the course of two weeks. We had a little working group, and I was in the details working on these products myself as well. And we had a lot of fun building with those tools. 

Nick Francis: And I think that that was sort of the beginning of what became our AI roadmap. But I think of AI as a tool. At the end of the day, we design our products for the optimal customer experience. Not our customer, their customer. We optimize for the user at the end of it: 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 customer’s experience at the end of the day. And so that perspective allowed us to do a lot of building and have a lot of fun with it, but the outputs look different, 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. 

Nick Francis: And we take a lot of pride in that because there’s a lot of companies out there, 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 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. 

Rob Walling: I have a note about a pricing overhaul in November of 2024, you guys moving from seat to per contact. That feels like a really bold, 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? 

Nick Francis: 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 moving the ball forward with regard to that aspect of our strategy. And so very early on, as I mentioned, we were building a lot with AI. We realized, wow, we’re going to be able to create a lot of value for our customers that doesn’t tie back to a seat. And generally you could sort of see: hey, if you fast-forward this ten 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, I felt like we were about to live an innovator’s dilemma where the incumbents were going to be at a strategic disadvantage. 

Nick Francis: They weren’t going to adopt this new technology fast enough. And there was going to be an opportunity for a little guy. Help Scout still like, yes, you could say 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, 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. 

Nick Francis: 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 I think that’s a funky metric. The person could literally reach out via email the next day, and 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, the one Drip was in. 

Nick Francis: And so we felt like it was generally acceptable. 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 saw the status quo and the way that people bought this software, and they wanted to do it that way. 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 per-seat SaaS particularly is that 20% of those seats shouldn’t be paying for anything because they’re not even using the tool. And so I wanted to go directly at that and try to win it against our competitors. And if there’s just not willingness to accept that business model, then I have to live to fight another day. 

Rob Walling: What a bold move. I mean, these are the types of big swings that you take that have 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? Was it tough? 

Nick Francis: Absolutely. At the end of the day, I feel like I just lost confidence from some of our stakeholders, and 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, I’m trying to build a hundred-million-dollar-plus company here when all of my competitors have raised ten times the amount. 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’ve got to grow, I’m going to swing for the fences. 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 I’m an entrepreneur. That’s what I’m built to do. 

Rob Walling: And then you already mentioned it: in late 2025, you stepped down as CEO, you became chairman of the board. It sounds like it was time. I was going to say, why did you decide to leave that role? 

Nick Francis: 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. So 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? What if the journey from $40 million to a hundred million, it’s just somebody else. And when I asked myself that question, I’ll be honest with you, Rob, a weight lifted, and I was like, well, then that would enable me to actually go do what feels true to me as an entrepreneur. Just no compromise, no tensions, 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. 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. 

Rob Walling: I was going to ask, you got another startup in you. Have you started working on it? Is it in stealth mode still? 

Nick Francis: Yeah, I am working on something. The weird thing about what I’m working on is that it’s not necessarily 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. 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. 

Rob Walling: What a great end to that story, man. 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 helping coach entrepreneurs and founders. 

Nick Francis: I will say 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. So many people have 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 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. 

Rob Walling: And if folks want to reach out to you, they can go to nick.francis, so it’s Nick Francis but with a dot before the “is.” 

Nick Francis: Yeah, that’s the Icelandic domain, I think. Is that what it is? 

Rob Walling: Icelandic? Yeah. And they can read your writings. You have a get-in-touch link and more about what you’re up to. Thanks so much for coming on the show, man. It’s been really great having you. 

Nick Francis: Oh, it’s my pleasure, buddy. Good to see you. 

Rob Walling: 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 TinySeed ecosystem. Thank you for listening this week and every week. This is Rob Walling signing off from episode 839.