Roland Siebelink

Breakthrough AI Operators

Business EN ↓ 30 episodes

Breakthrough AI Operators is a podcast about how the best startup founders are reinventing how their companies work. Not AI hype. Not vendor pitches. Real operators who've rebuilt significant parts of their business around AI — and can talk honestly about what worked and what didn't. Hosted by Roland Siebelink and Doug Miller, co-founders of Midstage Accelerator (7 unicorns built between them, 100+ leadership teams scaled), each episode features a founder who's achieved a genuine step-change breakthrough in how their company operates. These aren't productivity wins or tool adoption stories — t...

Author

Roland Siebelink

Episodes

Scaling Culture Through Storytelling | Vyntra | Gerlinde Boback | EP 104 25.11.2025 36:45

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. From cross-cultural leadership to building “baby values,” navigating layoffs with humanity, and choosin...

Fail 40 Times, Build a Hit | Sesh | Pepe Del Rio | EP 103 11.11.2025 39:33

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. Pepe shares how he: Went from a teenage tennis player in Madrid to leading one of the most innovative startups in...

Making HOAs Loved Again | Daisy | Yotam Cohen | EP 102 28.10.2025 40:32

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. Yotam reveals how 18 AI agents (complete with names, job titles, and even performance reviews) helped Daisy...

Introducing Scaling Without Breaking | Midstage Accelerator | Roland Siebelink | EP 101 15.10.2025 42:11

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. From managing chaos and hiring the right people to shifting from founder to true CEO, this candid conversation explores the realities of scaling a busi...

Scaling Without Breaking Podcast 15.10.2025 0:39

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...