Hosted by Roland Siebelink · 🇺🇸 US · EN · 24 episodes
Established thought leaders with verified media credentials.
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 — they're companies that are structurally different because of AI. If you're a founder at a 20–300 person company actively figuring out what AI means for your operating model and competitive position, this show gives you real stories from people in the field — not consult
Roland Siebelink hosts Breakthrough AI Operators, a business show with 24 episodes published.
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-fou
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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
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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 m
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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
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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 cl
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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 mark
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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 — i
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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 the latest episode of Scalin
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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 s
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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 Bechara Saab, Co-Founder &
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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
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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 scale
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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,
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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
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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 peo
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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
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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 to the uncomfortable truth: most companies don’t stall because o
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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 c
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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 a
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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
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Breakthrough AI Operators is hosted by Roland Siebelink. The show is categorised under business (management) and has published 24 episodes.
Breakthrough AI Operators has published 24 episodes.
Breakthrough AI Operators regularly covers business, management. It sits in the business category, with a management focus.
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Episodes of Breakthrough AI Operators average 31 minutes. a focused format where a clear narrative arc and tight preparation matter most.
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