# Roland Siebelink
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Making HOAs Loved Again | Daisy | Yotam Cohen | EP 102
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.
Y…
Fail 40 Times, Build a Hit | Sesh | Pepe Del Rio | EP 103
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…
How to Scale Enterprise Sales with A Team of 11 | Eon Media AI | Ashish Agarwal | EP 110
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 hard…
How to Scale to 8,000 Merchants with a Sub-70 Person Team | Montonio Finance | Karel Nappus | EP 111
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 “j…
The more AI spam there is, the better for my team! | Kontaktikeskus | Erki Koldits | EP 113
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…
How to Place Big Bets Without Betting the Farm | SeedLegals | Anthony Rose | EP 114
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.
No…
When Half Your Industry Thinks You're Dead Wrong | Mobio Interactive | Besh Saab | EP 115
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 & CEO of Mobio Interactive, who is building technology that uses biomarkers fr…
Shipping Every Week: The Release Strategy That Finally Unlocked Fieldmagic's Growth | FieldMagic | Glen Richmond | EP 116
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.
Enterprise-grade architecture.
…
Why Craft Still Matters in Fintech | Lithic | Robin Gandhi | EP 117
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 Roland Siebelink sits down with Robin Gandhi, Chief…
The AI Breakthrough Stories Most Founders Are Not Telling | Midstage Accelerator | Doug Miller | EP 200
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-founder of Midstage Accelerator, who has helped scale…
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