Scaling Without Breaking
The Podcast for Startup Leaders Who are Done Winging It
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There is nothing bigger or more influential in the world right now than AI. But what exactly is the current state of AI, and where is it headed? What about startups in the AI space?
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Every cap table company in Silicon Valley is burning venture capital chasing growth. Tom Milar built one that makes money instead — and he did it without ever raising a pre-seed round, despite managing $300 billion in client assets for companies including Perplexity AI.
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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 competitor with 100x the marketing budget — and decided the answer wasn't to compete harder. It was to stop competing on the same terms entirely.
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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 product-market fit — it's about whether you actually understand the cost your customer pays when your product doesn't exist. That number, by the way, is a quarter million dollars over a lifetime.
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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 this episode of Scaling Without Breaking, host Roland Siebelink sits down with Robin Gandhi, Chief Product Officer at Lithic, a card issuing processor built for high-growth technology companies — to unpack the one principle Robin believes separates truly great fintech companies from average ones: Craft.
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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 Fieldmagic, who nearly killed his startup by over-engineering it from day one.
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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 Dr. Bechara Saab, Co-Founder & CEO of Mobio Interactive, who is building technology that uses biomarkers from a simple selfie to assess mental well-being.
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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 SeedLegals, to explore the reality founders face when every decision can shape the future of their company.
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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 Kontaktikeskus, who once scaled the company from 25 to 250 employees — making it the largest call center in the Baltics.
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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 with Neil Cresswell, Founder & CEO of Portainer, who openly shares how chasing product-led growth in a market that didn’t buy that way nearly derailed his company.
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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+ — with a team of fewer than 70 people.No bloated org chart. No endless layers of management. No “just hire more people” solution.Instead, it was about operational discipline, clear positioning, repeatable systems, and the courage to say no when complexity tried to creep in. Because the real challenge of scale isn’t growth.It’s staying coherent while you grow.
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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 teams—with just 11 people, no outsourcing, and no external funding. The secret wasn’t working harder. It was refusing to fracture the product.In this conversation with host Roland Siebelink, Ashish breaks down what it actually takes to scale without breaking: staying product-led while serving enterprise customers, designing workflows that adapt without customization chaos, and building a team that understands customers deeply—not just tickets and specs.
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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 business without venture capital, without chasing growth for growth’s sake, and without losing control of what mattered most: customers, trust, and long-term thinking.We talk about what bootstrapping really costs, why white-labeling became a competitive advantage, how founder-led sales shaped the product, and what it actually looks like to scale slowly, intentionally, and sustainably—especially in a world being reshaped by AI.If you’re a founder or operator questioning the “faster is better” narrative, there’s a lot here that will challenge your assumptions.
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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 at the uncomfortable truth: most companies don’t stall because of product or market fit. They stall because the CEO hasn’t scaled yet. Matt has built companies from zero to $100M+, served as CEO and executive chair, advised hundreds of founders, and written the go-to books on being a startup CEO, CXO, and board member. In this episode, he shares the moments where he nearly broke himself—and the frameworks he developed to avoid breaking again.
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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 advice—becomes CEO of a company built to automate POCs?This conversation gets into the uncomfortable truth: POCs aren’t the problem. The way most teams run them is.
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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 Dragonfly, we get very real about one of the most expensive mistakes scaling teams make—building when they should buy.
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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 one of them.In this conversation, he breaks down how his company scaled AI negotiation agents from an idea to an engine trusted by Walmart, BMW, Rolls-Royce, and global enterprises moving hundreds of billions through automated procurement.
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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 down how to turn “boring processes” into shared narratives that teams actually want to rally around.
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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 fan community management platform that redefines how artists connect with their audiences.
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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 Co-founder of Daisy, the AI-native property management company disrupting how communities are run.
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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 faces when their company starts to outgrow them.
Listen to EpisodeScaling 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 people's calendars are a mess, and how to stop being your company's biggest bottleneck. The mission is to help founders scale without losing their minds or their culture.
You'll hear from startup CEOs, sharp edged investors, battle tested coaches, and operators who've been through the re and came out stronger. They'll share the hard lessons, team meltdowns, and systems that actually worked. If you're tired of vague advice and ready to build something that runs without constant fire fighting, this one's for you.
Roland Siebelink is the Founder Coach and CEO behind Midstage Institute, where he helps tech founders scale from chaos to clarity during periods of rapid growth. With firsthand experience scaling three startups from 10 to 1,000 employees in just three years, Roland brings a rare combination of operational insight and founder empathy to every conversation.
Founders turn to Roland when their companies hit the messy middle, when growth feels overwhelming and culture starts to slip. His clients credit him for bringing structure, focus, and calm to their scaling journeys, often doubling growth while preserving what makes their teams unique.
With more than two decades of experience, Roland specializes in helping CEOs of 50 to 200 person companies build resilient systems and leadership habits that support sustainable scale. He has also held executive roles in product and strategy at companies like Rocket Fuel and Topicmarks, and holds advanced degrees in business and social sciences from IMD Lausanne and Brussels Free University.
Originally from the Netherlands and now based in San Francisco with his husband and their rescue mutt, Roland brings a global perspective and a steady hand to every founder story.
• Growth-stage startup founders (Series A–C)
• CEOs who've transitioned from heroic hustler to strategic operator
• Venture capital partners who actually support their portfolio companies hands-on
• Investor-operators advising founders all the way through scale
• Former founders turned leadership advisors or coaches
• Fractional COOs and senior operators specializing in systems and scale
• Experts in organizational design, people ops, and team alignment
• Advisors on EOS, OKRs, and operational frameworks for growing teams
• Authors and speakers on startup leadership and company building
• Popular LinkedIn creators sharing insights on founder challenges
• Consultants helping startups scale culture, process, or go-to-market strategy
• Community builders and facilitators for founder networks and peer groups
Before Scaling Without Breaking, we produced Midstage Startup Momentum, a podcast where Roland Siebelink spoke with founders and operators from across the tech world. The show built a strong library of conversations that explored the real stories behind scaling. Guests talked about messy pivots, early hiring mistakes, and the turning points that helped their companies grow. Many listeners used the series as a practical guide for what it actually takes to move beyond the first stage of traction.
Across many interviews, Roland uncovered patterns that still shape our work today. Topics included how teams adjust after hitting 20 to 50 people, why discipline becomes more important than speed, and what separates leaders who stay in control from those who end up overwhelmed. These insights created the groundwork for Scaling Without Breaking, which continues the mission with deeper conversations and a sharper focus on helping founders grow without burning out.