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I Left My Company. Came Back to Find a Shell. Then Rebuilt It. | EP 119
Most founders who return to a company they once built come back to fix operations. Daniel Hanemann came back to WunderTax to find a company with 25 people, a plateauing market, and a unicorn…
I Spent My 18th Birthday Studying Credit Cards. Now I Run a Unicorn | EP 118
Most fintech companies build products for people who already have access. Kikoff was built by someone who didn't. The question this episode forces a founder to sit with isn't about market sizing or…
Why Craft Still Matters in Fintech | EP 117
Most fintech infrastructure is built to sell. Features designed for pitch decks. Prices set for markets. Products shipped fast. The result? Platforms everyone tolerates — but nobody loves. In the…
Shipping Every Week: The Release Strategy That Finally Unlocked Fieldmagic's Growth | EP 116
Building the “perfect” product sounds like the right move. It wasn’t. In this episode of Scaling Without Breaking, host Roland Siebelink sits down with Glenn Richmond, Founder & CEO of…
When Half Your Industry Thinks You're Dead Wrong | EP 115
Mental health assessments rely on what people say they feel. But what if words aren’t the most reliable signal? In this episode of Scaling Without Breaking, host Roland Siebelink sits down with…
How to Place Big Bets Without Betting the Farm | EP 114
Early-stage startups feel like a series of small decisions. They’re not. In this episode of Scaling Without Breaking, host Roland Siebelink sits down with Anthony Rose, Founder & CEO of…
The more AI spam there is, the better for my team! | EP 113
Returning to the company you founded sounds like a victory lap. Except, it wasn’t. In this episode of Scaling Without Breaking, host Roland Siebelink sits down with Erki Koldits, founder of…
We spent $12M chasing product-led-growth. Then doubled revenues by ignoring it. | EP 112
He spent nearly three-quarters of his $16M in funding. Not on bad hires. Not on a failed product. But on the wrong go-to-market playbook. In the latest episode of Scaling Without Breaking, I sat down…
S1E111 How to Scale to 8,000 Merchants with a Sub-70 Person Team | EP 111
Scaling to 8,000 merchants sounds like a hiring story. It wasn’t. In this episode of Scaling Without Breaking, host Roland Siebelink sits down with a founder who built a merchant network of 8,000+ —…
How to Scale Enterprise Sales with A Team of 11
Scaling looks glamorous until enterprise customers start pulling you in ten different directions. Ashish Agrawal built an AI company serving NBC Sports, Comcast, the PGA Tour, WWE, and U.S. Olympic…
Bootstrapping Clinked: 14 Years of Profitable SaaS Growth
Some companies are built fast. Others are built to last. This conversation is about the second kind. Tayfun Bilsel spent 14 years building Clinked.com into a profitable, multi-million-pound SaaS…
How to Scale Yourself as a CEO Without Breaking
What actually breaks when a company scales—and why does it so often happen between 30 and 100 employees? This conversation with Matt Blumberg goes straight to the uncomfortable truth: most…
Weaponize the POC: How to Turn Your Biggest Sales Liability into Your Secret Weapon | Scaling Without Breaking | EP 107
For years, sales leaders were taught to avoid POCs at all costs. They slow deals down. They spiral out of control. They kill momentum. So what happens when a longtime CRO—who preached that exact…
Your Series A Vanishes Because You Build What You Could Have Bought | Scaling Without Breaking | EP 106
At some point, every growing company hits the same wall: too many tools, too many decisions, and not enough clarity on what actually matters. In this conversation with Sven Sabas, founder of…
”While You Sleep, My AI Agents Close Deals in China” | Kaspar Korjus | Scaling Without Breaking | EP 105
As startups race to adopt AI, many enterprise leaders quietly admit they’re overwhelmed, underprepared, and unsure how to avoid becoming part of the 95% of failed AI initiatives. Kaspar Korjus isn’t…
Scaling Culture Through Storytelling: Vyntra’s Gerlinde Boback | Gerlinde Boback | Scaling without Breaking | EP 104
Most companies treat OKRs like a necessary evil. Gerlinde Boback treats them like a stage—where real people, real ingenuity, and real stories move the company forward. In this episode, she breaks…
Fail 40 Times, Build a Hit: The SESH Story | Pepe del Rio | Scaling Without Breaking | EP 103
What happens when your biggest weakness becomes your greatest advantage? In this episode of Scaling Without Breaking, host Roland Siebelink sits down with Pepe del Rio, founder and CEO of SESH, a…
Making HOAs Loved Again: The AI-Native Approach to Managing 200+ Buildings
Meet the startup that’s rewriting the rules of real estate—one digital employee at a time. In this episode of Scaling Without Breaking, host Roland Siebelink sits down with Yotam Cohen, CEO and…
Introducing Scaling Without Breaking | EP 101
In this special full-length episode of Scaling Without Breaking, host Roland Siebelink sits down with producer Nick for a deep dive into the why behind the podcast — and the hard truths every founder…
Scaling Without Breaking Podcast
Scaling Without Breaking is the podcast for startup leaders who are done winging it and ready to lead like CEOs. Straight talk only. Real stories about what breaks when your team hits 30, why…
Frequently Asked Questions
Scaling Without Breaking has published 20 episodes since October 2025, covering topics in Business, Management.
Scaling Without Breaking is currently highly active with new episodes weekly. Average episode length is 33m.
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