The Remarkable SaaS Podcast

Ton Dobbe

For B2B SaaS founders who are done blending in.

The Remarkable SaaS Podcast features unfiltered conversations with SaaS founders navigating the real challenges of building software that matters.

Hosted by Ton Dobbe, author of The Remarkable Effect, each episode zooms in on one of the 10 traits that define remarkable software companies—like offering something truly valuable and desirable, and aiming to be different, not just better.

Some guests are scaling fast. Others are still in the trenches—but all share hard-won lessons about what it really takes to create pull, shorten sales cycles, and become the only logical choice in their market.

Expect:

Honest conversations—no hype, no theory

Tactical insights from sales-led SaaS founders

Practical ideas you can apply to sharpen your product and your positioning

If you're building a SaaS business that deserves attention—not just more noise—this podcast is for you.

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S9 · E414
Wednesday · 46 min
#414 – How Dima Gutzeit rejected three markets and got to dictate the terms
A story about saying no until you're the only option. This episode is for founders who believe a horizontal product means a horizontal go-to-market. A product for everyone still needs a market of one. Dima Gutzeit, founder and CEO of LeapXpert, watched bankers in Hong Kong do their real work on WhatsApp in 2017, then spent two years building before selling anything. He wrote a large part of that first product himself. He built something that fits any industry. Then he turned down almost every industry that asked. Today he sets the terms, not only the price. And this inspired me to invite Dima to my podcast. We explore why he said no to marketing applications, CPaaS, and the contact centre business, and how that gave him the upper hand in the one category he kept in focus. You'll discover what he can ask of a customer today that he couldn't ask for in the early years. We also zoom in on two of the 10 traits that define remarkable software companies: Acknowledge you cannot please everyone Aim to be different, not just better Both are chapters in The Remarkable Effect. Remarkable companies decide who they are not for before the market decides for them. Here's one of Dima's quotes that captures how he thinks about what focus buys you: "In today's market, the only way to win is not the product. Anybody can create a product; it's velocity" By listening to this episode, you'll learn: Why a horizontal product and a horizontal go-to-market are separate decisions What saying no protects when the market starts pulling you sideways When the bigger customer gives you more room instead of less How years of focus turn into the speed you need later For more information about the guest from this week: Guest: Dima Gutzeit, founder and CEO, LeapXpert Website: leapxpert.com
S9 · E413
August 26 · 55 min
#413 – How Cyril Golub chose the ground Amazon can never stand on
A story about picking a fight your biggest competitor cannot win. This episode is for founders who believe the only answer to a bigger player copying them is to build faster. Most founders fear the day the giant copies them. It happened to Cyril Golub, CEO of Jinnify — Amazon shipped what they'd built within months. He'd spent twenty years inside e-commerce, long enough to know how marketplaces actually make their money. So, his answer wasn't to beat them by building faster. This inspired me to invite Cyril to my podcast. We explore why the strongest position isn't the one you defend, but the one your competitor cannot afford to take. Cyril shares what twenty years inside e-commerce taught him about reading a competitor. You'll discover what he saw in Amazon's business model that decided how he competes. We also zoom in on two of the 10 traits that define remarkable software companies: Master the art of curiosity Aim to be different, not just better Both are chapters in The Remarkable Effect. Cyril's story proves that remarkable companies don't out-build the giant. They choose ground the giant cannot take without damaging itself. Here's one of Cyril's quotes that captures how he thinks about growth: "The company should be ready to change, probably completely change level by level, and the main limiter here is the mindset of the founder and CEO." By listening to this episode, you'll learn: Why the real limit on scaling sits in the founder's head, not the market Why two founders make better decisions than three Why the safest position is one your competitor can't copy without hurting itself What to study when a platform starts building what you built For more information about the guest from this week: Guest: Cyril Golub, Founder and CEO of Jinnify Website: jinnify.ai
S9 · E412
August 12 · 47 min
#412 – How Martin Payne turned a flatlined company from $7M to $20M
A story about what he kept, and what he cut. For SaaS founders whose growth has stalled and who can't tell whether the problem is the company or the plan. Most new CEOs tear down what they inherit. Martin Payne, CEO of TextUs, took a different path. He replaced the founder CEO in April 2020. Growth had flatlined, cash was burning, and he laid off a third of the company in his first year. The business is now at $20M. He'll tell you most of what got it there was already in the building. And this inspired me to invite Martin to my podcast. We explore why a stalled company has more going for it than anyone inside can see. Martin shares what he found in his first months, the hardest call he had to make, and a culture his employees wrote. You'll discover the one thing he did twice, six years apart, for the same reason. We also zoom in on two of the 10 traits that define remarkable software companies: Master the art of curiosity Offer something valuable AND desirable Martin's story proves that remarkable companies read the signs others stopped noticing. Here's one of Martin's quotes that captures how he sized up what he inherited: "I came into the company thinking this is not a turnaround situation. This is a fine-tune, refine situation. And so I just went in with the mindset of there's goodness here. Now let me understand more specifically where the goodness is. Let me understand where specifically things need to be removed or changed." By listening to this episode, you'll learn: Why a stalled company rarely needs the rebuild everyone assumes What intellectual honesty looks like when you inherit someone else's company When retention tells you more about growth than new revenue does How to make culture stick For more information about the guest from this week: Guest: Martin Payne, CEO of TextUs Website: textus.com Nice surprise this week: Feedspot ranked The Remarkable SaaS Podcast 17th in their Top 70 Tech Startup Podcasts. Thanks for listening — that's the only reason it's there.
S9 · E411
July 8 · 45 min
#411 – Alex David: The question AI made everyone forget
A story about thinking harder while everyone builds faster. This episode is for founders wondering why shipping faster with AI hasn't made their product any better. Building has never been easier. That's exactly the problem. Alex David spent a decade in pricing — Simon-Kucher, then Segment — before founding unSurvey, an AI company G2 acquired last year. Today, he leads AI Solutions there. His worry is simple: the tools got cheap, but good judgment didn't. While everyone rushed to build, he kept asking the question most people skip ”Is this even worth building?” This inspired me, hence I invited Alex to my podcast. We explore why the founders who win aren't the ones building fastest — they're the ones who know what's worth building. Alex shares why he walked away from a company that was working to start another and what a decade in pricing taught him about worth. You'll discover why the price was never yours to set — and what that changes about everything you build. We also zoom in on two of the 10 traits that define remarkable software companies: Master the art of curiosity (trait 4) Create momentum (trait 8) Alex's journey is an excellent example of the mindset that goes behind how remarkable software companies build something people just keep talking about. Here's Alex's approach to deciding what to build and what not: "The price is what the price is to the customer; that's what it's worth to them. You have two options: You build a product that is profitable within that constraint, or you have to spend a lot of marketing dollars to educate the customer on why they're wrong, and why it should be worth more." By listening to this episode, you'll learn: Why asking why matters more now that building costs almost nothing What real momentum is made of — and why founders manufacture it Why hope is what stops founders from pivoting in time Why acquisitions live or die on people, not terms For more information about the guest from this week: Guest: Alex David, Founder and CEO of unSurvey. Today, GM of AI Solutions at G2 Website: g2.com (and g2.ai)
S9 · E410
July 1 · 53 min
#410 – How Mazy Dar found room in Google and Microsoft's market — and won the world's biggest banks
A story about the market everyone assumed was taken. This episode is for founders wondering how to find room in a market owned by giants. The biggest software market in the world looked fully taken. Mazy Dar, CEO of Here, found room in it anyway. He spent 26 years on one pain the giants' browsers aren't built around — a browser made for work, not the public internet. The world's biggest banks now run mission-critical work on it. And this inspired me to invite Mazy to my podcast. We explore how you find room in a category owned by Google and Microsoft — and why the slice they leave open turned out to be sizeable. Mazy shares why he named the company after an idea rather than a product, and what he learned serving the most locked-down desktops in the world. We also zoom in on two of the 10 traits that define remarkable software companies: Acknowledge you cannot please everyone Sell the idea, not the product Mazy's journey proves that remarkable companies don't fight the giants head-on. They find the ground where they can become the only logical option. Here's one of Mazy's quotes that captures how he thinks about a problem hiding in plain sight: "This is not like a crazy concept. What's crazy is that in this one category of product, the web browser that's the most widely used in the world, it's the one area where the one size fits all seems to be the thing that everyone assumes is the correct answer." By listening to this episode, you'll learn: Why holding one problem for years can beat chasing the next trend What it really costs to let big customers design your product for you When to stop building only what your founding segment demands Why selling the idea outlasts selling the product For more information about the guest from this week: Guest: Mazy Dar, co-founder & CEO of Here Website: here.io Mazy's email: mazy@here.io
S9 · E409
June 24 · 46 min
#409 – How Renaud Charvet chose ownership over speed — and made Ringover impossible to copy
A story about what compounds when you don't take the shortcut. This episode is for sales-led SaaS founders who invested to grow fast but now realize they forgot to grow their differentiation. Most software companies buy speed — they build on someone else's foundation — and never count the cost. Renaud Charvet, co-founder and US CEO of Ringover, took the opposite path. He started in 2005 selling cheap international calls, watched Skype and WhatsApp kill that business, and built something new from scratch. Bootstrapped for fifteen years, then raised to expand — and moved his family to the US to make it work. He's never once taken the shortcut. And this inspired me to invite Renaud to my podcast. We explore how choosing ownership over speed creates an edge competitors can't copy. Renaud shares how he thinks about what's worth owning, where to focus, and what actually makes customers stay. You'll discover why the slow, expensive choice compounded into something no shortcut could match. We also zoom in on two of the 10 traits that define remarkable software companies: – Aim to be different, not just better – Acknowledge you cannot please everyone Renaud's journey proves remarkable companies don't copy the playbook — they own what others rent and let the advantage compound. Here's one of Renaud's quotes that captures how he thinks about building an edge: "Focus — it might feel slower in the short term, but it compounds much faster in the long term." By listening to this episode, you'll learn: What you give up the day you build on someone else's stack What changes when you stop selling features and start selling outcomes What he did when the US market ignored him Why the customers easiest to win are the ones who leave For more information about the guest from this week: Guest: Renaud Charvet, co-founder and US CEO of Ringover Website: ringover.com
S9 · E408
June 17 · 43 min
#408 – How Stan Markuze refused the me-too game and made buying a no-brainer
A story about choosing the one thing no competitor would copy. This episode is for sales-led SaaS founders stuck in a crowded category, wondering how to escape the price-and-features war In a crowded category, most founders just try to win it. Stan Markuze, CEO of Balance, did something else. Five companies in, with two auto-tech exits and a decade in real estate, he'd seen what a price war looks like. So when seven companies were selling the same treasury tool, he refused to be the seventh. And this inspired me to invite Stan to my podcast. We explore how refusing to compete on everyone else's terms creates an edge no rival can copy. Stan shares why he walked away from a feature-and-price war, and what turns a quiet user into a vocal one. You'll discover what happened to his sales cycle once buying his product stopped being a debate. We also zoom in on two of the 10 traits that define remarkable software companies: – Aim to be different, not just better – Turn customers into fans Stan's story proves remarkable companies don't fight harder inside the category—they change what they get measured on. Here's one of Stan's quotes that captures how he thinks about the standard SaaS model: "We turned the business model upside down. Usually, you pay an annual SaaS fee for a treasury management product. What we do is, if people sweep cash through our platform, for those who sweep a certain threshold, we would actually give them the treasury management system at no cost, because we're able to monetize the automatic sweeps." By listening to this episode, you'll learn: Why removing friction you can't see beats chasing growth you can What makes an ROI concrete enough to close on the first call Why the metric you stop tracking matters as much as the one you keep How a tight niche turns happy customers into a referral flywheel For more information about the guest from this week: Guest: Stan Markuze, CEO of Balance Website: balancecash.io
S9 · E407
June 10 · 52 min
#407 – How Martin Gourdeau refused the commodity race and added $1M ARR in 9 months
A story about choosing the harder fight on purpose. This episode is for SaaS founders wondering why adding more features to their niche product isn't creating the edge it used to. Most niche SaaS races to add features—and wonders why margins shrink. Martin Gourdeau, CEO of Vacation Tracker, took a different path. After running Workleap as President and GM, he took a year off to study what's actually changing in software—then chose a 22-person bootstrapped company over another large stage. And he didn't pick Vacation Tracker by accident. He picked it because he believes the next wave of software will be won by a very different kind of company. And this inspired me to invite Martin to my podcast. We explore what he saw in that year off—and why it shaped a very different bet on what wins next. Martin shares why a small bootstrapped company now has an edge most large companies will never get back, why he changed the one number that decides when his whole team gets a raise, and what kind of SaaS he thinks AI will quietly destroy. We also zoom in on two of the 10 traits that define remarkable software companies: – Aim to be different, not just better – Create NEW value possibilities Martin's journey proves that the next wave of remarkable software companies won't look like the last. Here's something Martin observed that explains where he thinks the real opportunity sits: "High performers are notoriously bad at managing their energy levels because of this obsession to perform." By listening to this episode, you'll learn: Why most SaaS companies are competing in the wrong layer Why ARR-per-head changes the behavior of every employee What high performers get wrong about their own energy Why delegation to agents is the skill most leaders lack For more information about the guest from this week: Guest: Martin Gourdeau, CEO of Vacation Tracker Website: https://vacationtracker.io
S9 · E406
June 3 · 44 min
#406 – How Chad Gaydos chose fit over TAM and doubled deal sizes in 12 months
A story about asking the question many CEOs avoid—and finding real money. This episode is for SaaS CEOs with a nagging feeling that their growth isn't compounding the way it should. Most CEOs chase market size. And miss what actually matters. Chad Gaydos, CEO of Procurify, took a different path. With 30 years across SAP, Skillsoft, Talkdesk, and Total Expert, he's learned that growth isn't about how big the market is—it's about how well you fit it. When he took the CEO seat in January 2025, he asked a question most operators skip: Is there a real use case here—or just a big number? And this inspired me to invite Chad to my podcast. We explore why use-case fit—not market size—is what actually compounds growth. Chad shares why his first move was repositioning the entire company, why the product was being sold to the wrong customers, and why saying yes to the wrong customer is more expensive than saying no. We also zoom in on two of the 10 traits that define remarkable software companies: – Master the art of curiosity – Acknowledge you cannot please everyone Chad's journey proves that remarkable companies don't grow by chasing markets—they grow by reading them differently than everyone else. Here's one of Chad's quotes that captures how he reads markets: "What drew me wasn't procurement per se. It was really what was going on in this last category of the Office of the CFO. I felt like it hadn't been written yet." By listening to this episode, you'll learn: Why use-case fit beats TAM size What happens when pricing finally matches the value you deliver When the first 90 days demand subtraction, not addition How to make hard decisions without committee paralysis For more information about the guest from this week: Guest: Chad Gaydos, CEO of Procurify Website: https://www.procurify.com
S9 · E405
May 27 · 57 min
#405 – Burak Karakan, CEO of Bruin - On the cost of trying to please everyone
A story about an opinionated founder, the customers he turns away, and the ones who stay. This episode is for SaaS founders quietly wondering whether trying to be a fit for every buyer is what's slowing them down. Most founders think the goal is to be a fit for as many buyers as possible. Burak Karakan, Co-founder and CEO of Bruin, runs his company on the opposite belief. A former engineering manager at HelloFresh, he built an opinionated product — and he's at peace with the buyers who walk away because of it. And this inspired me to invite Burak to my podcast. We explore why being opinionated on purpose creates focus, speed, and the right kind of customer base. Burak shares his thinking on the question that qualifies a buyer in five minutes, why he hires juniors over seniors right now, and what happened when his team stopped tracking competitors altogether. You'll discover why he turns down deals that other founders would take. We also zoom in on three of the 10 traits that define remarkable software companies: – Acknowledge you cannot please everyone – Aim to be different, not just better – Master the art of curiosity Burak's journey proves that remarkable companies don't try to be a fit for everyone — they hold their position, and the right customers find them because of it. Here's one of Burak's quotes that captures his thinking: "It's unbelievable to me that engineers think they are there just to build stuff. No, you're there to solve problems, and sometimes solving that problem will especially require you to not build something." By listening to this episode, you'll learn: Why opinionated products attract better customers than agreeable ones What question reveals whether a buyer is a real fit in five minutes When ignoring your competitors becomes your sharpest strategic move Why hiring juniors right now beats hiring seniors For more information about the guest from this week: Guest: Burak Karakan, Co-founder & CEO of Bruin Website: https://getbruin.com
S9 · E404
May 20 · 50 min
#404 – How Tim Barker proved the software org chart is now optional
A story about rebuilding how a company runs from the ground up. This podcast is for SaaS founders wondering whether the playbook they've been running is still enough to keep their edge. Most software CEOs scale by hiring. Few question that. Tim Barker, CEO of Attain IP, walked away from the obvious next move. After scaling Salesforce in EMEA, leading DataSift through Twitter's data shutdown, and running a public mental health platform for five years, he turned down PE roles and board seats to start over. New company, new market — white-box AI for patent attorneys. But the real bet wasn't the market. It was the build: five people, no functional org, agents doing the work a department used to. That's the choice I wanted to understand. This inspired me to invite Tim to my podcast. We dig into how the operating model of a software company gets rebuilt when one person can run what used to take a department. Tim shares his thinking on why products should be bought not sold, why trust is now a measurable input, and why the obvious next move is rarely the remarkable one. We also zoom in on two of the 10 traits that define remarkable software companies: Sell the idea, not the product Master the art of curiosity Tim's story proves that remarkable companies don't follow the obvious playbook—they question the foundations everyone else takes for granted and build what works now. Here's one of Tim's quotes that captures how his definition of a winning product has shifted: "There's no MVP in our world, in our vocabulary. It's replaced by the minimum magical product. Magical products drive word of mouth, and our North Star is: once I've used it, I'm never going back." By listening to this episode, you'll learn: Why systems beat super prompts in any AI-first business What separates products people buy from products you have to sell Why trust is a measurable input, not just a brand value Why uncomfortable choices teach faster than comfortable ones For more information about the guest from this week: Guest: Tim Barker, CEO at Attain IP Website: attainip.ai
S9 · E403
May 13 · 40 min
#403 – Why Amos Bar-Joseph rejected the playbook every unicorn ran
A story about questioning the play itself—not the execution. For SaaS founders quietly wondering whether their next round will fix what the last one didn't. Most founders who fail try harder the next time. Amos Bar-Joseph, co-founder and CEO of Swan, took a different path. Three-time founder. Two prior B2B startups built on the unicorn growth-at-all-costs playbook—both ended in failure. On the third one, he didn't tighten his execution. He rejected the play—and reached seven figures in ARR in just nine weeks. And this inspired me to invite Amos to my podcast. We explore why questioning the playbook creates a different kind of edge. Amos shares the thinking behind scaling talent first, not headcount—why mental capacity is the bottleneck, why knowledge has to become software, why meetings and alignment calls are the real cost of scale. We also zoom in on three of the 10 traits that define remarkable software companies: – Aim to be different, not just better – Master the art of curiosity – Focus on the essence Amos's journey proves that remarkable companies don't follow consensus—they question what everyone else accepts and walk away from it. Here's one of Amos's quotes that captures his philosophy on how a business should be built: "We're scaling our talent inside the company so we can discover what does it look like the 100x version of an engineer, the 100x product, the 100x seller, the 100x marketeer. [...] A business that is designed from the ground up to scale its employees, not a business that employees are designed to scale the business." By listening to this episode, you'll learn: Why convention is the fastest path to mediocrity in software What changes when revenue per employee becomes your North Star metric Why mental capacity is the real bottleneck, not headcount Why knowledge has to live in the system, not the team For more information about the guest from this week: Guest: Amos Bar-Joseph, Co-founder & CEO of Swan Website: https://www.getswan.com
S9 · E402
May 6 · 44 min
#402 – How Joseph Lee refused to outspend his rivals — and outgrew them anyway
A story about advantages that capital cannot buy. This episode is for SaaS founders who are watching better-funded rivals raise round after round—and questioning whether outspending is really the only way to win. Most founders chase scale before they've earned the right. Joseph Lee, CEO of Supademo, took a different path. After six years and several pivots in his previous company, he started Supademo in early 2023 with a bootstrap mindset—even after raising. He did the gritty work that bigger competitors refused to do, and shared every harsh lesson in public from day one. The result: mid-seven-figure ARR — built by a team of 11. And this inspired me to invite Joseph to my podcast. We explore why founder-led grit beats capital when capital is everywhere. Joseph shares why he stopped tracking twenty metrics to focus on three, and why he believes 99% of a startup's momentum has nothing to do with the founder. You'll discover what happens when the smaller player chooses the work the bigger players won't touch. We also zoom in on two of the 10 traits that define remarkable software companies: Turn customers into fans Master creating momentum Joseph's journey proves that remarkable companies don't outspend competitors—they build flywheels competitors can't buy. Here's one of his quotes: "You need to build the right levers into your business where you're riding the momentum of the market or momentum of the product. We're not doing as much like hand-to-hand combat." By listening to this episode, you'll learn: Why structural market dynamics drive 99% of a startup's momentum What makes 100 early customers more valuable than 10,000 later ones Why measuring twenty metrics hides what three actually reveal Why trust compounds when founders share lessons publicly from day one For more information about the guest from this week: Guest: Joseph Lee, CEO of Supademo Website: https://supademo.com
S9 · E401
April 29 · 42 min
#401 – How Alex Levin grew Regal 4x while ignoring what everyone else was doing
A story about refusing what the market expected—and a business that grew stronger for it. This episode is for sales-led SaaS founders wondering why adding more people keeps making growth harder, not easier. When I last spoke with Alex Levin in 2022, Regal was already scaling. Since then, revenue has grown 4x—with the exact same team. Back in 2022, Regal was growing fast, and the team was expanding with it. Alex made a different call. He stopped hiring to solve problems—and started solving problems instead. Three and a half years later, the team is exactly the same size. The revenue isn't. He said no to entire customer segments. He stopped solving product gaps with people. He moved from $50K average contracts to over $150K—without adding a single person to make it happen. The result is a business approaching cash-flow break-even with most of its $83M still in the bank and revenue growing 50 to 100% a year. And this inspired me to invite Alex back to my podcast—three and a half years after our first conversation. We explore how questioning every default assumption about growth creates compounding advantage. Alex shares hard-won insights about the ego trap of hiring, the shift from $50K to $150K average contracts, and why AI agents didn't change his core belief—they finally made it scale. You'll discover what happens when a founder refuses the obvious answer—and finds that the constraint was always the key. We zoom in on two of the 10 traits that define remarkable software companies: – Acknowledge you cannot please everyone – Focus on the essence Alex's story proves that remarkable companies grow their leverage, not their headcount. Here's one of Alex's quotes that captures his thinking on building a business that forces clarity: "Don't solve problems with people, like solve the problem and then hire people if you, you know, if you want to. That's a very big shift in how companies are run." By listening to this episode, you'll learn: Why the most valuable employee is the one who automates their own job out of existence What saying no to a whole customer segment does for average contract value Why the constraint you kept accepting was actually the problem all along Why the fastest solution to a product gap is often the most expensive one long-term For more information about the guest from this week: Guest: Alex Levin, CEO & Co-founder Website: regal.ai
S9 · E400
April 15 · 34 min
#400 - What 99 CEOs wish they'd known sooner
Four hundred episodes. When I started this podcast, I had one simple belief: the best lessons in building a remarkable software company don't come from business books or consulting frameworks. They come from CEOs who've lived it — the ones who made the hard calls, paid for the wrong assumptions, and built something worth talking about. I went back through the last 99 conversations — and pulled the 18 insights that I believe will genuinely open your eyes. Not the ones that make you nod. The ones that hold a mirror. I selected them for one reason: each one connects directly to the traits I write about in The Remarkable Effect. The patterns that separate the software companies people keep talking about from the ones that quietly disappear. Six don'ts. Twelve do's. The don'ts follow one thread — each one is an assumption that ended up costing a CEO everything. The do's move from the inside out — who you need to be, how you compete, how you grow, and who you put around you. Here's who you'll hear from: DON'TS Harpreet Singh, Co-CEO Launchable — on the mistake that erodes confidence in leadership faster than anything else Josh Ellars, CEO OpenGTM — on the decision he kept making wrong, more than once Ed Bradley, CEO Virtualstock — on why being turned down by every investor was the best thing that happened to him Emeric Ernoult, CEO Agorapulse — on the reason he almost gave away part of his company for nothing Krishna Raj Raja, CEO SupportLogic — on which hiring mistake is actually more dangerous Jason Cohen, Founder WPEngine — on the belief that quietly kills more scaling companies than anything else DO'S Matt van Itallie, CEO Sema — on why the leadership book's answer didn't work Richard White, CEO Fathom — on what the best YC founders had in common that surprised him Matt Achariam, CEO Mesh — on what falls apart when momentum arrives too fast Scott Reynolds, CEO UpCodes — on the question most AI founders can't answer Mark Walker, CEO Nue — on why creating a new market isn't always the best idea Caitlin MacGregor, CEO Plum — on why CEOs should spend more time selling Tal Peretz, CEO Onfire — on saying no to customers who wanted to pay him Jason Cohen, Founder WPEngine — on the one thing worth fixing before everything else Emeric Ernoult, CEO Agorapulse — on why testing for the outcome is the wrong test Theo Saville, CEO CloudNC — on the difference between a busy team and a focused one Randy Wootton, CEO Maxio — on what nobody tells you before you sit in the CEO chair Jon Jorgensen, CEO The Access Group — on how he actually went about finding the right people Dinakara Nagalla, CEO EmpowerMx (acquired by IFS) — on what remarkable actually means when nobody is watching
S9 · E399
April 1 · 46 min
#399 – How Louis Hoch rejected the obvious customers—and grew when rivals collapsed
A story about choosing who not to serve—and building competitive advantage no crisis can touch. This episode is for sales-led SaaS founders who've never tested whether their revenue would survive a major market shock — and aren't sure they want to know the answer. Most software companies are built to serve as many customers as possible. Louis Hoch, CEO of Usio, chose differently. Louis has been building in payments since 1998. He raised $50 million while competitors raised $200 million—and won. He built a company that processes enough direct bank payment volume to rank as the 50th largest bank in the United States. When COVID hit and rivals saw revenue drop by as much as 80%, Usio grew. That outcome wasn't luck. It was a customer decision made years earlier that most CEOs would never make. What Louis did—deliberately, by design—was say no to entire industries. Not because he couldn't serve them. Because serving them would have cost him everything else. And this inspired me to invite Louis to my podcast. We explore how deliberate customer rejection builds a resilience that no market crisis can touch. Louis shares insights about turning regulatory hurdles into early competitive positioning, building payment channel diversity while staying ruthlessly focused on vertical, and why the companies that fail are often the ones who stayed truest to their original idea. You'll discover what happens to your revenue when a crisis hits — and you made the right customer choices years earlier. We also zoom in on two of the 10 traits that define remarkable software companies: Acknowledge you cannot please everyone Aim to be different, not just better Louis's story proves that remarkable companies don't just pick their market—they pick what they will never serve, and build their advantage from that constraint. Here's one of Louis's quotes that captures his philosophy on what it takes to survive as a founder: "What you think you're going to be when you start a software company and what you end up being are often different. The companies that are successful understand that. The companies that fail try to maintain their focus on what their original product or service is." By listening to this episode, you'll learn: Why going public before your first customer can be your strongest sales move Why giving customers the conditions to choose beats telling them what they need Why your original business plan may be the biggest threat to your survival Why operating leverage has to be designed in from the start — not stumbled into later Guest: Louis Hoch, CEO and Chairman of Usio Website: usio.com
S9 · E398
March 25 · 45 min
#398 – How Scott Reynolds bet on depth over breadth and built a position that sticks
A story about choosing the hard problem—and winning because of it. This episode is for sales-led SaaS founders who feel their product lead shrinking—and wondering what actually creates a position competitors can't close. Most founders chase obvious markets. Scott Reynolds chose a complicated one nobody else wanted. Scott, co-founder and CEO of UpCodes, is a trained architect who has lived the pain of navigating construction regulations. Weeks buried in phone-book-sized regulations that no software had organized—until he built it. While others built broad tools for obvious problems, Scott went narrow and deep. His conviction: if it's not dramatically better, it isn't worth building. And this inspired me to invite Scott to my podcast. We explore why going deep into one vertical beats building broad for everyone. Scott shares what forces professionals to call a tool irreplaceable, why vertical depth compounds, and what a decade of quiet data does when AI arrives. You'll discover why his bet keeps getting stronger. We also zoom in on two of the 10 traits that define remarkable software companies: – Aim to be different, not just better – Offer something valuable and desirable Scott's story proves that remarkable companies find the problems others walk past—and build advantages that compound. Here's one of Scott's quotes that captures his thinking on competition in the AI era: "We view that marriage of our data and their data to give them a unique instance of AI that can just answer questions better than their competitor could. And I think that's a very critical component of competition in an AI era." By listening to this episode, you'll learn: Why a 10% improvement rarely moves anyone—and what threshold actually drives adoption What choosing a vertical others ignore reveals about long-term defensibility When combining your data with customer data creates an advantage nobody else can access Why the hardest problems to solve are often the strongest positions to own For more information about the guest from this week: Guest: Scott Reynolds, Co-founder and CEO UpCodes Website: up.codes
S9 · E397
March 18 · 39 min
#397 – How Dean Mathews rejected conventional growth and built a company 170,000 people rely on every month
A story about measuring success differently—and what that single decision builds. This episode is for SaaS founders who sense their growth metrics are missing something — and can't put their finger on what. Many SaaS companies track monthly active users. Dean Mathews asks a different question when he looks at that number. Dean Mathews, Founder and CEO of OnTheClock, launched his time-tracking company in 2004 after reading complaints in a small business forum. For the next decade, he ran it as a side project — patient, focused, and measuring success by one question: are we actually helping people? That question changed what he built, how he hired, and why customers keep coming back. And this inspired me to invite Dean to my podcast. We explore how measuring success by people rather than revenue changes what a software company becomes. Dean shares why monthly active users became his north star, why 20 years of patience in one segment compounds in ways rapid growth never does, and what really drives customers to recommend you without being asked. You'll discover how a 4.9 out of 5 customer support rating and 7–8% word-of-mouth referrals trace back to one belief about what business is actually for. We zoom in on two of the 10 traits that define remarkable software companies: – Turn customers into fans – Master the art of curiosity Dean's story proves remarkable companies don't obsess over revenue metrics—they obsess over the people those metrics are supposed to represent. Here's one of Dean's quotes that captures his philosophy on what makes a team culture actually work: "The biggest one for me is connecting their work to the actual value that's delivered to a customer, and showing them that their work actually matters. That's like gold." By listening to this episode, you'll learn: Why measuring success by people helped—not revenue—changes how your whole team behaves What turns occasional users into customers who recommend you to friends and colleagues Why staying in one segment for 20 years compounds in ways most founders never see Why connecting every team member to customer outcomes creates effort no salary can buy For more information about the guest from this week: Guest: Dean Mathews, Founder & CEO of OnTheClock Website: ontheclock.com
S9 · E396
March 11 · 52 min
#396 – Why Hewitt Tomlin reversed course at $10M
A story about admitting your own strategy pulled you away from what matters. This episode is for sales-led SaaS founders wondering whether their expansion strategy is building strength—or spreading them thin. Most SaaS founders treat $10M as proof the playbook works. Hewitt Tomlin, CEO of TeamBuildr, treated it as a reason to question everything. He and his college teammate James Peters built TeamBuildr from a frustration with paper workout programs into a $10M strength and conditioning platform—with fewer than 50 employees and zero outside capital. But at $10M, Hewitt made a choice most founders wouldn't. He stopped building new products—and started rebuilding the one that got him there. And this inspired me to invite Hewitt to my podcast. We explore why a bootstrapped founder at $10M chose restraint over expansion—and what that decision reveals about building real competitive advantage. Hewitt shares hard-won lessons about a pricing mistake he calls his biggest error, an acquisition that taught him the cost of scarcity thinking, and why he now hires from the profession he serves. You'll discover what happens when a founder stops chasing more and starts going deeper. We also zoom in on two of the 10 traits that define remarkable software companies: – Focus on the essence – Master the art of curiosity Hewitt's story proves that remarkable companies don't keep adding—they challenge everything that doesn't move the needle, even when it's their own strategy. Here's one of Hewitt's quotes that captures his long-term conviction: "Our existing application is responsible for 10 million in revenue. It's not bad. There's a good argument there for not changing anything, and continuing to tack on 2 million in revenue a year. But no, we're convinced it's the right thing to do, because we feel like, if it's gotten us so far for 10 years, then the new version will carry us for 10 years into the future." By listening to this episode, you'll learn: Why early revenue matters less than the insight your first customers carry What happens when a $10M founder chooses depth over new product lines Why analysis without intuition leads to your most expensive mistakes How hiring from your customer's profession builds a moat competitors can't copy For more information about the guest from this week: Guest: Hewitt Tomlin, CEO & Co-Founder Website: teambuildr.com
S9 · E395
March 4 · 46 min
#395 – How Bassem Hamdy created something no competitor can touch
A story about destroying your own work—and creating what lasts. This episode is for sales-led SaaS founders who suspect their product is slowly becoming a custom shop—and don't know how to stop it. Bassem Hamdy, CEO and Co-Founder of Briq, has spent 25 years in construction technology—three software revolutions, three companies. He says Briq found product market fit every 24 months. Each time meant tearing something down to build the next version. Each time, the same thing triggered the rebuild — the company had started solving for individual customers instead of the market. And this inspired me to invite Bassem to my podcast. We explore why the instinct to please your biggest customers creates exactly the kind of fragility that kills companies. Bassem shares hard lessons about killing a product he spent two years building, the moment his QA team exposed how far the company had drifted, and why domain expertise—not platform size—determines who wins in vertical AI. We also zoom in on two of the 10 traits that define remarkable software companies: – Acknowledge you cannot please everyone – Master the art of curiosity Bassem's journey proves that remarkable companies refound themselves before the market forces them to. Here's one of Bassem's quotes that captures what happens when a company starts drifting: "Software is like jello. You slap that thing, it's going to shake the hell out of it. So the moment you inject that code, that's client specific, you're pooched." By listening to this episode, you'll learn: Why saying yes to customers can turn your product into something nobody else wants When to check whether your team is building a product or managing client tickets Why deep domain expertise matters more than platform size in the age of AI How one metric—revenue per employee—changes every decision a CEO makes For more information about the guest from this week: Guest: Bassem Hamdy, CEO and Co-Founder of Briq Website: briq.com

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