The Remarkable SaaS Podcast

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

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

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

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

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