INTERVIEW | Make Money Building a Billion-Dollar Business: Lessons from Three Founders

Summary

Travis Makes Money – INTERVIEW | Make Money Building a Billion-Dollar Business: Lessons from Three Founders

Host: Travis Chappell
Date: July 1, 2026
Episode Focus: Featuring transformative insights from Tomer London (Gusto), Jim Lebenthal (Serity Partners), and Richard Harpin (HomeServe) on what it takes to build businesses worth billions.

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Episode Overview

This "best of" compilation episode brings together three accomplished founders and executives, each of whom has played a key role in building billion-dollar businesses. Through in-depth conversation, they uncover the mindsets, operational approaches, and critical lessons that enabled their companies’ exceptional growth. The episode is filled with practical advice, candid reflections on mistakes and successes, and actionable strategies for ambitious listeners looking to level up their own ventures.

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Key Discussion Points & Insights

1. Tomer London (Gusto) — Building Tech for Small Business [03:19–08:19]

Founding Story & Mission

• Tomer describes the formation of Gusto and how he and his co-founders united over a shared passion for helping small businesses, shaped by their family backgrounds.

  “We had this passion and love for small businesses because of our families... helping sell, seeing how it feels like to figure out every single customer interaction, figure out pricing, figuring out your cash flow...” (Tomer London, 03:32)

Product vs. Tech: Defining Roles

• Product focuses on close interaction with customers, understanding workflows and pain points, and translating that into technological solutions.
• Tech is about executing those visions, writing code, and building the infrastructure.

  “You need to understand technology very deeply... and then you try to bring together to build these kind of ideas and concepts about how to take those two things together and come up with like a concept.” (Tomer London, 05:26)

The Iterative Process & Customer Focus

• The importance of constant iteration — spending time with customers, rapidly prototyping ideas, and refining based on feedback.
• Product management is about leading this learning loop, working closely with engineering and design to achieve impact.

Product is Greater than Marketing

• Travis expands: the better the product, the less you need to rely on marketing and sales to compensate for weaknesses.

  “If you're bad at product, you gotta be good at marketing. If you're bad at marketing, you gotta be good at sales.” (Travis, 06:46)

Deployment of Capital

• A key challenge for serving small businesses is balancing investments in marketing, customer acquisition, and product retention.

  “That's the center of why it's been so difficult and challenging... to produce great software and services for small businesses.” (Tomer London, 08:19)

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2. Jim Lebenthal (Serity Partners) — The Long Game in Billion-Dollar Finance [09:35–14:33]

On Experience, Learning, and Market Wisdom

• Success in finance isn't just about intelligence—it's about sustained discipline, openness to new ideas, and above all, experience.
• Advocates for voracious, well-rounded learning: “That means a voracious amount of reading. It means reading newspapers or websites from both sides of the political aisle... It means understanding, finding out what industry trends are going on right now.” (Jim Lebenthal, 09:52)

The Value of Time in Markets

• Market timing is a “fool’s errand.” Endurance pays more than tactical brilliance.

  “I really realize more experientially the importance of staying in the markets for long periods of time. I realize that market timing is really a fool's errand.” (Jim Lebenthal, 10:35)

Famous Market Lesson

• If you simply stayed in the market for 30 years, annualized returns ≈ 9%. But if you missed just the 20 best days, that plummets to less than half.

  “There’s a famous chart... If you tried to market time and you missed the best 20 days out of those 30 years... your annual return goes down by more than half.” (Jim Lebenthal, 11:56)

• The best days almost always follow the worst; hard as it is psychologically, you must be in the game during tough times.

  “The best days tend to be clustered right next to the worst days. And you don't want to take the chance of missing those 20 best days out of 30 years.” (Jim Lebenthal, 13:09)

Humility Against the Experts

• Travis lampoons the notion that armchair investors can beat the pros:

  “You think sitting in your spare bedroom in a bathrobe, in a bag of... halfway down a bag of Doritos, you think you're going to be able to out earn all of the smartest investors the world has ever seen?” (Travis, 13:21)

Key Takeaway

• Stay invested, diversify, and leverage time: “Just trust that the economy's probably going to go up and to the right given enough time.” (Travis, 13:48)

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3. Richard Harpin (HomeServe) — Scaling Simple Solutions to Billions [14:44–24:17]

On Timing Growth and Funding

• Avoid over-ambition early—prove your model and bootstrap before seeking investors.

  “Don't be too ambitious and grow the business too quickly. Wait till you've proved out the model... and then you want to press the accelerate button and that's maybe the time that you seek an investor, but not like I did, give away over half of the business.” (Richard Harpin, 14:44)

• Reflects on giving away 52% equity for £500k to keep the business afloat. No regrets but a caution for others:

  “We had to give up 52% of the equity in return for half a million pounds to keep the business going... But ideally... only sell them a minority shareholding.” (Richard Harpin, 15:10)

Imposter Syndrome & Leadership Evolution

• Eight years in, he realized he preferred business development over daily operations, so he promoted his chief of business development, allowing himself to focus on expansion.

  “I brought in a guy that ran business development in the UK... called him into my office one day and said, Jonathan, congratulations, you're promoted. I'm giving you my job. Managing director of HomeServe UK...” (Richard Harpin, 16:38)

International Expansion Lessons

• Test new countries personally before committing resources.

• Stay as close as possible to your proven business model—don’t adapt it by more than 15% (the “15% rule”) or risk failure.

  “If you need to change your model by more than 15%, think again about going into that country.” (Richard Harpin, 18:39)

• Go for nearby, easier-to-operate countries first, not just huge markets.

Customer Acquisition & Lifetime Value

• Sought a two-year payback on customer acquisition spend; in the US proved the model with less than one year payback due to high retention and recurring revenue.

  “We were looking for ideally a two year payback on the marketing... over 80% retention rate... a two year payback was really, really attractive.” (Richard Harpin, 19:56)

• Upfront annual membership payments heavily aided cash flow; business was so cash-generative as to rarely need external funding.

Cross-selling Effectiveness

• The real money was in upselling and cross-selling to existing customers:

  “Typically the cost of acquiring an extra product sale from an existing customer is five times more cost effective than acquiring that customer in the first place.” (Richard Harpin, 22:28)

Operational Complexity—Managing Scale

• Heavy reliance on call center support suited their older customer base.
• To manage risk and claims surges, they used insurance underwriters to insulate both company and customers.

  “...we brought in insurance underwriters to make sure that if there was ever a... very high level of claims, that we were insured and that therefore the customer was always going to get the benefit.” (Richard Harpin, 24:17)

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Notable Quotes & Memorable Moments

• Tomer London on building for small business: “This incredible thing we have in common, which is this, this passion and love for small businesses because of our families... and all the hardship and the excitement about running a business was something that was very inspiring to me.” (03:32)
• Jim Lebenthal on market wisdom: “Market timing is really a fool's errand... When we talk about the best days in the market... those best days almost always happen right on the heels of the worst days in the market.” (10:35 & 12:30)
• Richard Harpin on model discipline: “Stay true to your original business model. I call it the 15% rule. If you need to change your model by more than 15%, think again about going into that country.” (18:32)

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Timestamps for Key Segments

• [03:19] – Tomer London on Gusto’s founding and product vs. tech roles
• [06:46] – Travis on product quality versus marketing and sales
• [08:19] – Challenges building for small businesses
• [09:35] – Jim Lebenthal on intelligence, drive, and experience in finance
• [11:56] – The danger of missing the best days in the stock market
• [13:21] – Travis mocks market timing for amateur investors
• [14:44] – Richard Harpin on the hazards of early-stage funding and over-ambition
• [16:35] – Harpin’s experience with imposter syndrome and passing the baton
• [17:52] – Lessons on international expansion and the 15% rule
• [19:56] – Customer acquisition costs, retention, and cash cycle mechanics
• [21:29] – Upselling and cross-selling to drive value
• [23:25] – Operationalizing call center support for customer experience
• [24:17] – Managing scale and risk with insurance underwriters

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Takeaways

• Obsess Over Product & Customers: Deep customer empathy and product quality lessen the need for heavy marketing spend.
• Experience (and Endurance) Matter: In business and the markets, no hack replaces hard-earned wisdom over the long term.
• Prove the Model Before Scaling: Don’t rush into funding or foreign expansion until your core business model performs with minimal adaptation.
• Leverage Existing Customers: Upselling and cross-selling to a loyal base can be a far superior growth engine than constant new customer acquisition.
• Operational Preparedness: Have systems in place, such as insurance coverage, to weather inevitable periods of high demand or crisis.

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This episode is packed with hard-won lessons and actionable insights from genuine billion-dollar builders, providing a rich roadmap for entrepreneurs and aspiring business leaders alike.

Transcript

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Imagine that you're listening to the Travis Makes Money podcast presented by GoHighLevel.com for a free 30 day trial of the best all in one digital marketing software tool on the planet. Just go to gohighlevel.com travis what's going on everybody? Welcome back to the Travis Makes Money podcast where it's our mission to help you make more money. On this episode of the show. We are starting a series for compilation episodes just for the next few days. Just because we have been doing this daily interview show for about a year and a half now and we have so many amazing people and I thought it'd be really fun. Since we are done with the first six months of 2026, I thought it'd be fun just to look through some of the recent guests that we've had on and compile some episodes that would be hard hit getting really good information, some of the best of conversations that I've had just all put into one episode. So on this episode of the show, I'm featuring three different guests that we've had on and this is the billion dollar episode. Okay, so this is going to be featuring first of all Tomer London, who is the co founder and chief product officer over at Gusto, which is a essentially a human resources software platform for small business and mid market sized businesses. But yeah, they, they're doing pretty well. They've raised over half a billion in venture capital, but they're also now completely profitable. They did over a billion in revenue last year and are continuing to grow. So they're completely self sustaining at this point, not looking to raise any more capital and doing extremely well. And so that's what it takes to build billion dollar business. Next we have Jim Labenthal. Jim is the is Serity Partners chief market strategist. So Serity Partners is a registered investment advisory firm. 40,000 clients, 1700 colleagues and $180 billion in assets under management. And so he's also a regular contributor to CNBC about the markets. He wrote a new book, how to Ride the Subway. Very, very interesting guy. Really interesting conversation. Somebody who understands the markets on a level that I will never even touch. So again, somebody who's the chief market officer for a firm managing over $180 billion in assets might know a thing or two about getting to A billion. And then next we have Richard Harpin. Richard's the founder of a company called Homeserve, which is so simple sounding, it's mind numbing. Basically, they insure your main water line because it's not covered under normal homeowners insurance. It's like 60 bucks a year. I don't know, something crazy simple and cheap like that. But because it was such a good service, he sold that company a couple years ago for over £4 billion. British guy, over £4 billion. So, Tomer London, Jim Lebenthal, Richard Harpin, all very, very qualified to talk about what it takes to get to this billion dollar number. So please, without further ado, enjoy this compilation episode with three of my good friends. How did your career end up pivoting into the direction of becoming a Chief Product Officer when that was not the original intention of your degree?

[B]

Yeah, for me we started the origins of Gusto was Josh, Eddy and I just found each other as like the right match to build a company together. And we connected on, you know, on one, which is our previous experiences building companies. So I had an earlier startup back in Israel that was not successful, but I really, really learned a lot from that and I felt like, you know, I kind of, that's what I want to do. I want to build something and that's meaningful for period of time with partners. And Josh and Eddie have had, you know, similar, you know, experiences with their startups. So we came together and then very quickly we figured out that, you know, this incredible thing we have in common, which is this, this passion and love for small businesses because of our families, where we come from and, you know, where we grow, where we grew up. My dad has a clothing store, as I mentioned earlier, and, you know, just being there, living in this, like going to the store a few times a week, helping sell, seeing how it feels like to figure out every single customer interaction, figure out pricing, figuring out your cash flow, coming in, going out, figuring out just the day to day of paying the bills and all the hardship and the excitement about running a business was something that was very inspiring to me. And then it's someone that was really close and cared a lot about computers and software. It just felt like consumers get this amazing technology, you know, they can use every day. Back then it was like the iPhone just came out, you know, is this a good, great example of that? And then on the other side, you have enterprises like big companies who have incredible technology to run their businesses, but the people in the middle, the small businesses often, you know, are left behind. And they just don't have great software and great services to run their business. So for us it felt like a great opportunity to build something and serve people that we love and build something special. What we know about building, you know, great products.

[A]

Yeah, can you talk a little bit about. So explain the differences between tech and product. Like when you're the chief product officer, what is it within your roles and responsibility? What, what are you mainly accountable for doing?

[B]

Yeah, yeah, yeah. So the thing that I love doing the most, which happens to align beautifully with what it means to be a product manager, is to one, spend a lot of time with customers, understand their workflow, understand their pain points, understand what works, what doesn't work. And then two, use all that knowledge to understand, to come up with concepts and ideas of, you know, how to, how to, how to solve these problems using technology. So it's kind of a fun place where on one side you need to understand technology very deeply and on the other side you need to understand the customer very deeply. And then you try to bring together to build, to build these kind of ideas and concepts about like how to, how to take those two things together and come up with like a concept. And then in phase two, call it like you work very closely with engineering and design to actually build this and then iterate on it with more customer feedback. And iterate with more customer feedback. So that loop is something that the product person, product manager is usually, you know, really leading. And you know, I didn't know any of this stuff by the way, you know, until, you know, just before we started gusto. You know, product management did not exist like 30 years ago at this where it is today. But in the end of the day like it kind of takes. I think it's a great fit for people who care a lot about, they love spending time with customers, love learning about problems, then love like working with technology at the other side.

[A]

Yeah, basically the, the tech and product arms have to work very closely together, but they're two. So I had a tech startup a few years ago and that was probably one of the biggest learnings that I took away was understanding that like, oh, these are two different worlds. Like you can have, you can have a full time person just on product, dude never even touches a line of code. And then you can have a full time tech person that's just writing code. And that was something that was like brand new to me. But it also was really important to me to try to understand that to some degree because I come from like a sales background. So I was just doing, I was a hustler, you know, I was just doing door to door sales for years and years before I started the podcast, got into the online business world. And then once I, once I really started getting a good understanding of, of how important it was to build good product, that's really when I started like leveraging that a little bit more because, you know, that naval quote, I'm going to butcher it because I always do. But it was something about, you know, product is greater than marketing, which is greater than sales or something like that. Like, like if you're bad, if you're bad at product, you gotta be good at marketing. If you're bad, if you're bad at marketing, you gotta be good at sales. And it was just like, oh yeah, no duh. Like the better you make the product, the more time you spend with the customers, the more easily work through the program, the less you have to spend on taking time to market, taking time to sell. How, how have you guys sort of, sort of looked at your Runway in terms of deploying capital against these different types of the, these different parts of the business? Marketing, sales, customer acquisition versus like product retention, you know, net promoter score, things like that.

[B]

Yeah, that's, that's the center of why it's been so difficult and challenging for, for, for the industry to produce great software and services for small businesses. It's exactly that. This summer, soccer is here and so are the watch parties. And Ubereats has your game day essentials covered with 30 off orders from Aldi Kroger and Dollar General. Everything you need to keep your crowd happy, delivered straight to your door. Chips, dips, fresh ingredients and more. Order in so you can lock in for the games. 30% off your grocery order only on UberEats for a limited time.

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[C]

Yeah, so let, let me add on to the earlier point I was making about earnestness and empathy. You have to have a certain level of intelligence. I'm not calling myself Smart. That's not what I mean. What I mean by that is you have to have the drive and the discipline to learn this craft.

[A]

Yeah.

[C]

And that means a voracious amount of reading. It means reading newspapers or, you know, websites from both sides of the political aisle. Not finding yourself being down a rabbit hole, whether it's social media or traditional media that has a just one editorial bent. It means understanding, finding out what industry trends are going on right now. By the way, it helps for me to be at a firm like Serity Partners. You were so kind to talk about the size of the firm. And that size of the firm allows us to see a lot of what's going on in the industry. And I'm every day learning something new in this industry. So you have to have that drive, that discipline, and that openness to new ideas. But I'll tell you one thing, and maybe this will disappoint some of your listeners. I don't know. I do think experience matters. Now, I don't want to discourage Somebody who's 25 years younger than me. I just said I started 27 years ago, right? So I remember a prospect once saying, you're too young. And I thought, well, that kind of hurts. I mean, don't you want to give me a chance? You know, it's. Now that I'm older, I've seen a thing or two. I really realize more experientially the importance of staying in the markets for long periods of time. I realize that market timing is really a fool's errand. And I hope I don't irritate any of your viewers, but that's what I so strongly believe.

[A]

Irritate away, Jimmy. Irritate away. Don't apologize for that.

[C]

I will, Travis, because I've gotten feedback on this before. There's a famous chart looking at the S&P 500 over the last 30 years. And it says if you just stayed in the market during the last 30 years, my number may be off a little bit. But you earn something like 9% per annum over the last 30 years. If you tried to market time and you missed the best 20 days out of those 30 days. So not even the best, you know, one day a year, your return, your annual return goes down by more than half.

[A]

That's insane.

[C]

And it's. I. I'm. I'm sorry. I'm gonna shamelessly plug my book again. It's in the book with a chart that shows it. Here's two things to think about. One, somebody out there is going to be Listening to this and saying, yeah, okay, smart guy. Well, what if you missed the worst days of the year? It's by market time. Okay? Of course your, your returns would be higher, but think about that 9% per annum return that far and away strips out. It surpasses inflation. Even with what we've seen over the past few years, your purchasing power goes up a lot, by 9%. And I also have to add this very important point. When we talk about the best days in the market and missing those 20 best days, those best days almost always happen right on the heels of the worst days in the market. So it's actually easy to say, hey, the market's high, I want to get out. That's easy. But you have to get back in when every fiber of your instinct says, don't get back in because it's a bloodbath out there. Yeah, you know, we saw it last year on April 9th when we'd had four bad days, really bad days in a row after the Liberation Day tariff announcement. And then snap of a fingers, we go higher and it's off to the races. The best days tend to be clustered right next to the worst days. And you don't want to take the chance of missing those 20 best days out of 30 years.

[A]

Yeah, no kidding. And like, my thing is that you have people like you, and you have people like the Buffetts of the world, and you have the Ray Dalios of the world who have dedicated their, like, decades of their professional career to learning this game, and they still don't know how to time the market completely. And you think sitting in your spare bedroom in a bathrobe, in a bag of, you know, halfway down a bag of Doritos, you think you're going to be able to out earn all of the smartest investors the world has ever seen. Like, it just doesn't make any sense to me. And it's so like you're doing so much more work to make less money. Just, just trust that the, the economy's probably going to go up and to the right given enough time. And let time be on your side and just put the money in the things that you believe in, as well as a bunch of different funds, and then you're probably going to be pretty, pretty good. This episode is brought to you by Accenture. When your advertising operations fall out of sync, everything else follows. Spotify and Accenture are working together to reinvent the rhythm of ad sales using automation, analytics, and smarter workflows to simplify campaign delivery and access better data across the Business.

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[D]

The other bit of advice is I didn't follow this, I know it now, but I didn't at the start of my entrepreneurial journey is don't be too ambitious and grow the business too quickly. Wait till you've proved out the model, bootstrap the business. Ideally, hold back on getting an investor until you proved your model and then you want to press the accelerate button and that's maybe the time that you seek an investor, but not like I did, give away over half of the business. We had to give up 52% of the equity in return for half a million pounds to keep the business going. So keep it small, prove the model, get to profitability and then if you need money to scale, that's when you should bring in an investor. But find an investor that can help you and only sell them a minority shareholding.

[A]

So here's the question. Would the business have survived had you not taken on that half million pound investment?

[D]

No. So I don't regret it. And that half a million pounds over the next 29 years became a £4.1 billion sale?

[A]

Yeah, I think your investor was probably pretty happy with that.

[D]

Yes.

[A]

At what point, what point did or did you ever reach a point where you felt imposter syndrome or some version of under qualification to continue scaling the business? Like when you start getting, when you start seeing some of these revenue numbers pouring in. Was there ever a time where you were like, I gotta find somebody else to run this thing, I don't know what I'm doing here?

[D]

Yeah, there was, it was eight years in and I was good at finding the right model eventually, but I didn't much like running the day to day business. I like the international expansion, the business development, not running the day to day customer service. So I brought in a guy that ran business development in the UK for a year, did a great job, called him into my office one day and said, jonathan, congratulations, you're promoted. I'm giving you my job. Managing director of HomeServe UK, when we were only a UK business and that meant I could work on the business rather than in the business. And he kept growing the uk, delivering great service. And I started thinking about, I wonder whether HomeServe would work in a foreign country.

[A]

What's your first step when you're moving into a new market like that? Does it look almost identical to when you started the business in the uk. Are you starting from a different position because you've already proven that successful in a different market or is it like back to grassroots because you're not sure how it's going to work or perform in this other market?

[D]

My learning was it's really important that the founder is out prospecting different countries to find the one that they think will work best first. In fact, we went into France as the first international country and France is really difficult. There's a high cost of employing people. If those people are not the right ones, it's very difficult to get rid of them. But we were owned. But the group that invested in HomeServe were themselves 30% owned by General Deseaux, the big French water company. So we got a deal with them to go into France. They persuaded us to change the business model and we did and we persevered for a year and the new model didn't work. So out of desperation, just when we were about to give up, we went back to the original direct mail model. We used the water company brand of General Deseaux service and guess what? It worked. So the learning is stay true to your original business model. I call it the 15% rule. If you need to change your model by more than 15%, think again about going into that country.

[A]

It's better to find another market than it is to find another model.

[D]

Yes. And don't go to a country too far away and don't get seduced by going to a really big country. Go to an easier one that's close by and prove that you can become an international business.

[A]

When it came to your, your acquisition of customers, I assume you know these, or at least at the time knew these metrics like the back of your hand. What, what were you looking for in terms like what were you happy with for a customer acquisition cost versus the lifetime value of your customer?

[D]

Yeah, we were, we were looking for ideally a, a two year payback on the, on the marketing. So because we were getting a over 80% retention rate that this is a recurring income membership model, then a two year payback was really, really attractive. And when we proved out the model in the us we were getting a less than a one year payback and that was a function of really high take up rates on the direct marketing branded as the local water utility or electric company or gas company, a one

[A]

year payback on that. So but even then, even then is still a full year of cash cycle. Right. So you're putting money out, you're not seeing that back for 12 months. Did you have to go raise more money at some point to continue acquiring customers. Do you have enough of a, of a war chest? What, what was the finance, what was the, what were the finances of the company looking like for that time period?

[D]

Yeah, we, we only ever as a public company did a, about a hundred 125 million pound equity raise but actually a year or two later we gave 100 million back to shareholders. So as a public company we didn't actually need money to grow because most of our members were paying upfront for the whole year's membership then it was a extremely cash generative business.

[A]

Were there any upsells along the way or was it just this one core product and it was good enough for you just to focus on expanding that one core product?

[D]

No, it was the most attractive part of the business model was the cross selling and the upselling. So when people had bought water service line cover alone, then we would go to them and sell them plumbing emergency cover and then electrics cover and then furnace breakdown cover.

[A]

Got it. So increased coverage across other things. But the initial offer being attractive enough, like I said, where it's, I mean, I mean, hey, if the main waterline does go out, that is going to be annoying. It's whatever it was 50, 60 bucks a year, like may as well go ahead and get that. The uptake on that was so the conversion rate on that was so high that it was basically like let's keep this front end offer as this one core service. Then once we get in, you hitting them with emails, you hitting them with phone team.

[D]

Yeah, there was a, some outbound calling to existing members and there would be suggestions when they might be calling us to change their address or with a query and we'd be also be sending direct mail because that worked in the first place. So typically the cost of acquiring an extra product sale from an existing customer is five times more cost effective than acquiring that customer in the first place.

[A]

Yeah, I just love the idea of that low ticket model where it's just like there's not a ton of barrier, there's not a lot of friction in the buying process when it's something like that, where it's not 50 bucks a month, it's 50 bucks a year or whatever the price point is. And it just makes it easy just to say yeah, let's go ahead and do this. Is it when somebody gets that, are they calling in like do you have an inbound call center or you tried to do all of this online.

[D]

Now a big part of the model is having a 1-800-free-phone-call center call. A lot of our customers are older, retired. They worry about things going wrong in the home, and therefore they want the reassurance of a number they can call that's answered quickly and to let them know that the plumber will be on their way.

[A]

So the operational complexity there, did that introduce any complications in terms like, so you have a year of, you know, one to two years, let's call it, before you make your money back on acquiring the customer. But then you have operational costs that also eat into that margin as well. Right. So was there, were there any concerns, from your perspective as you scaled the company as quickly as you ended up scaling it, that you were not going to be able to keep up with the demand that you were creating?

[D]

No. One of the things that we did was we, we brought in insurance underwriters to make sure that if there was ever a, an ice age and therefore a very high level of claims, that we were insured and that therefore the customer was always going to get the benefit.