Breakthrough AI Operators
Roland SiebelinkBreakthrough 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, 10... more
| Publishes | Weekly | Episodes | 25 | Founded | 8 months ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | ManagementBusiness | |||
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Latest Episodes
The most advanced AI operating model in this episode wasn't built from a strategy deck. It was built from desperation — and that turns out to be the best design constraint available.
Miloš Djurdjevic is co-CEO and co-founder of heyData, a Berlin-bas... more
Most AI adoption failures at growing startups aren't technology problems. They're a founder who is moving fast, surrounded by a team that isn't — and a growing gap between the two that no new tool subscription will close.
Roland Siebelink is co-foun... more
Most PE investors see a 25-year-old automation business in 2026 and calculate the half-life. Ali Evans saw the one thing AI can't replicate overnight: trust earned over decades of client relationships. The conventional move would have been to exit be... more
Open source AI models are now just 3-5% behind the best closed source models on benchmarks — about six months of lag time, not five years. If you're building an AI infrastructure company on the assumption that OpenAI or Anthropic will maintain a perm... more
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 incl... more
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... more
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... more
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 latest episode of Scaling Without Breaking, host Ro... more
Key Facts
Chart Rankings
How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.
Apple Podcasts | #57 |  Philippines/Business/Management |
Top Management Podcasts
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| Listeners per Episode | Gender Skew | Location | |||
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| Interests | Professions | Age Range | |||
| Household Income | Social Media Reach | ||||
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Breakthrough AI Operators launched 8 months ago and published 25 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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