Scaling Without Breaking

Roland Siebelink

English Business Entrepreneurship Management

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Episodes 9

Avg. Duration 40m

Activity Highly Active

Since Oct 2025

Latest Episode Jan 2026

Outreach Signals

Features Guests

Publishing Details

Schedule

Every 2 Weeks

Format

Episodic

Consistency

80%

Hosting

feeds.podetize.com

About This 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 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 firefighting, this one’s for you.

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Recent Episodes

How to Scale Yourself as a CEO Without Breaking

Jan 13, 2026 35m

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 companies…

Weaponize the POC: How to Turn Your Biggest Sales Liability into Your Secret Weapon | Scaling Without Breaking | EP 107

Jan 06, 2026 46m

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

Dec 23, 2025 43m

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

Dec 09, 2025 42m

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

Nov 25, 2025 36m

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…

Fail 40 Times, Build a Hit: The SESH Story | Pepe del Rio | Scaling Without Breaking | EP 103

Nov 11, 2025 39m

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…

Making HOAs Loved Again: The AI-Native Approach to Managing 200+ Buildings

Oct 28, 2025 40m

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

Oct 15, 2025 42m

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…