The Remarkable SaaS Podcast

#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 curiosityTim'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 businessWhat separates products people buy from products you have to sellWhy trust is a measurable input, not just a brand valueWhy uncomfortable choices teach faster than comfortable onesFor more information about the guest from this week: Guest: Tim Barker, CEO at Attain IP Website: attainip.ai

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#403 – Why Amos Bar-Joseph rejected the playbook every unicorn ran

3w ago00:40:00Tap to summarize

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 essenceAmos'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 softwareWhat changes when revenue per employee becomes your North Star metricWhy mental capacity is the real bottleneck, not headcountWhy knowledge has to live in the system, not the teamFor more information about the guest from this week: Guest: Amos Bar-Joseph, Co-founder & CEO of Swan Website: https://www.getswan.com

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#402 – How Joseph Lee refused to outspend his rivals — and outgrew them anyway

4w ago00:44:41Tap to summarize

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 fansMaster creating momentumJoseph'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 momentumWhat makes 100 early customers more valuable than 10,000 later onesWhy measuring twenty metrics hides what three actually revealWhy trust compounds when founders share lessons publicly from day oneFor more information about the guest from this week: Guest: Joseph Lee, CEO of Supademo Website: https://supademo.com

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#401 – How Alex Levin grew Regal 4x while ignoring what everyone else was doing

Apr 2900:42:37Tap to summarize

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 essenceAlex'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 existenceWhat saying no to a whole customer segment does for average contract valueWhy the constraint you kept accepting was actually the problem all alongWhy the fastest solution to a product gap is often the most expensive one long-termFor more information about the guest from this week: Guest: Alex Levin, CEO & Co-founder Website: regal.ai

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#400 - What 99 CEOs wish they'd known sooner

Apr 1500:34:35Tap to summarize

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'TSHarpreet Singh, Co-CEO Launchable — on the mistake that erodes confidence in leadership faster than anything elseJosh Ellars, CEO OpenGTM — on the decision he kept making wrong, more than onceEd Bradley, CEO Virtualstock — on why being turned down by every investor was the best thing that happened to himEmeric Ernoult, CEO Agorapulse — on the reason he almost gave away part of his company for nothingKrishna Raj Raja, CEO SupportLogic — on which hiring mistake is actually more dangerousJason Cohen, Founder WPEngine — on the belief that quietly kills more scaling companies than anything elseDO'SMatt van Itallie, CEO Sema — on why the leadership book's answer didn't workRichard White, CEO Fathom — on what the best YC founders had in common that surprised himMatt Achariam, CEO Mesh — on what falls apart when momentum arrives too fastScott Reynolds, CEO UpCodes — on the question most AI founders can't answerMark Walker, CEO Nue — on why creating a new market isn't always the best ideaCaitlin MacGregor, CEO Plum — on why CEOs should spend more time sellingTal Peretz, CEO Onfire — on saying no to customers who wanted to pay himJason Cohen, Founder WPEngine — on the one thing worth fixing before everything elseEmeric Ernoult, CEO Agorapulse — on why testing for the outcome is the wrong testTheo Saville, CEO CloudNC — on the difference between a busy team and a focused oneRandy Wootton, CEO Maxio — on what nobody tells you before you sit in the CEO chairJon Jorgensen, CEO The Access Group — on how he actually went about finding the right peopleDinakara Nagalla, CEO EmpowerMx (acquired by IFS) — on what remarkable actually means when nobody is watching

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#399 – How Louis Hoch rejected the obvious customers—and grew when rivals collapsed

Apr 100:46:10Tap to summarize

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 betterLouis'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 moveWhy giving customers the conditions to choose beats telling them what they needWhy your original business plan may be the biggest threat to your survivalWhy operating leverage has to be designed in from the start — not stumbled into laterGuest: Louis Hoch, CEO and Chairman of UsioWebsite: usio.com

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#398 – How Scott Reynolds bet on depth over breadth and built a position that sticks

Mar 2500:45:26Tap to summarize

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 desirableScott'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 adoptionWhat choosing a vertical others ignore reveals about long-term defensibilityWhen combining your data with customer data creates an advantage nobody else can accessWhy the hardest problems to solve are often the strongest positions to ownFor more information about the guest from this week: Guest: Scott Reynolds, Co-founder and CEO UpCodesWebsite: up.codes

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#397 – How Dean Mathews rejected conventional growth and built a company 170,000 people rely on every month

Mar 1800:39:49Tap to summarize

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 curiosityDean'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 behavesWhat turns occasional users into customers who recommend you to friends and colleaguesWhy staying in one segment for 20 years compounds in ways most founders never seeWhy connecting every team member to customer outcomes creates effort no salary can buyFor more information about the guest from this week:Guest: Dean Mathews, Founder & CEO of OnTheClockWebsite: ontheclock.com

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#396 – Why Hewitt Tomlin reversed course at $10M

Mar 1100:52:28Tap to summarize

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 curiosityHewitt'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 carryWhat happens when a $10M founder chooses depth over new product linesWhy analysis without intuition leads to your most expensive mistakesHow hiring from your customer's profession builds a moat competitors can't copyFor more information about the guest from this week:Guest: Hewitt Tomlin, CEO & Co-FounderWebsite: teambuildr.com

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#395 – How Bassem Hamdy created something no competitor can touch

Mar 400:46:45Tap to summarize

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 curiosityBassem'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 wantsWhen to check whether your team is building a product or managing client ticketsWhy deep domain expertise matters more than platform size in the age of AIHow one metric—revenue per employee—changes every decision a CEO makesFor more information about the guest from this week:Guest: Bassem Hamdy, CEO and Co-Founder of BriqWebsite: briq.com

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All episodes

#404 – How Tim Barker proved the software org chart is now optional

#403 – Why Amos Bar-Joseph rejected the playbook every unicorn ran

#402 – How Joseph Lee refused to outspend his rivals — and outgrew them anyway

#401 – How Alex Levin grew Regal 4x while ignoring what everyone else was doing

#400 - What 99 CEOs wish they'd known sooner

#399 – How Louis Hoch rejected the obvious customers—and grew when rivals collapsed

#398 – How Scott Reynolds bet on depth over breadth and built a position that sticks

#397 – How Dean Mathews rejected conventional growth and built a company 170,000 people rely on every month

#396 – Why Hewitt Tomlin reversed course at $10M

#395 – How Bassem Hamdy created something no competitor can touch