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PODCAST

Scaling Without Breaking

Roland Siebelink

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

business management

All Episodes

28:59

Why Craft Still Matters in Fintech | EP 117

Scaling Without Breaking ·

2026/04/07

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 Product Officer at Lithic — a card issuing processor built for high-growth technology companies — to unpack the one principle Robin believes separates truly great fintech companies from average

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24:35

Shipping Every Week: The Release Strategy That...

Scaling Without Breaking ·

2026/03/31

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. Zero-downtime deployments. Full DevOps pipelines. All built before meaningful customer feedback. The result? Months-long release cycles. Slow iteration. A product at risk of falling behind. Because the

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21:23

When Half Your Industry Thinks You're Dead Wrong | EP...

Scaling Without Breaking ·

2026/03/25

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 from a simple selfie to assess mental well-being. No long surveys. No biased self-reporting. No guesswork. Instead, the conversation explores objective emotional measurement — using science and AI to

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29:51

How to Place Big Bets Without Betting the Farm | EP 114

Scaling Without Breaking ·

2026/03/20

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 perfect playbook. No guaranteed outcomes. No “safe” path forward. Instead, the conversation focuses on making high-stakes bets, navigating uncertainty, and thinking clearly when the answers aren’t

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25:31

The more AI spam there is, the better for my team! |...

Scaling Without Breaking ·

2026/03/11

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 the Baltics. Then he stepped away. Years later, he received the call no founder wants: the company had become a rudderless ship. So Erki returned. Not to preserve the past. But to rebuild the company from

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26:35

We spent $12M chasing product-led-growth. Then...

Scaling Without Breaking ·

2026/03/04

He spent nearly three-quarters of his $60M 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, Founder & CEO of Portainer, who openly shares how chasing product-led growth in a market that didn’t buy that way nearly derailed his company. Investors wanted PLG. The market needed enterprise sales. And when you’re selling mission-critical infrastructure software, engineers

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28:25

How to Scale to 8,000 Merchants with a Sub-70 Person...

Scaling Without Breaking ·

2026/02/24

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 “just hire more people” solution. Instead, it was about operational discipline, clear positioning, repeatable systems, and the courage to say no when complexity tried to creep in. Because the real challenge of

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35:12

How to Scale Enterprise Sales with A Team of 11

Scaling Without Breaking ·

2026/02/10

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 harder. It was refusing to fracture the product. In this conversation with host Roland Siebelink, Ashish breaks down what it actually takes to scale without breaking: staying product-led while serving

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47:17

Bootstrapping Clinked: 14 Years of Profitable SaaS...

Scaling Without Breaking ·

2026/01/27

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 capital, without chasing growth for growth’s sake, and without losing control of what mattered most: customers, trust, and long-term thinking. We talk about what bootstrapping really costs, why white-labeling became a competitive advantage, how founder-led sales shaped the

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35:19

How to Scale Yourself as a CEO Without Breaking

Scaling Without Breaking ·

2026/01/13

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 of product or market fit. They stall because the CEO hasn’t scaled yet.Matt has built companies from zero to $100M+, served as CEO and executive chair, advised hundreds of founders, and written the go-to books on being a startup CEO, CXO, and board member. In this episode, he shares

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46:18

Weaponize the POC: How to Turn Your Biggest Sales...

Scaling Without Breaking ·

2026/01/06

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 company built to automate POCs?This conversation gets into the uncomfortable truth: POCs aren’t the problem. The way most teams run them is.Steve Davis, CEO of Provarity, has spent three decades in Silicon Valley sales—BDR to CRO to CEO. He breaks down why pre-sales has been ignored

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43:42

Your Series A Vanishes Because You Build What You...

Scaling Without Breaking ·

2025/12/23

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 about one of the most expensive mistakes scaling teams make—building when they should buy.Sven shares a firsthand story of spending millions and 18 months building foundational tech that already existed, why engineers are wired to overbuild, and how opportunity cost quietly becomes the

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42:10

"While You Sleep, My AI Agents Close Deals in China"...

Scaling Without Breaking ·

2025/12/09

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 conversation, he breaks down how his company scaled AI negotiation agents from an idea to an engine trusted by Walmart, BMW, Rolls-Royce, and global enterprises moving hundreds of billions through automated procurement.You'll hear the real story behind landing Walmart as an early

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36:45

Scaling Culture Through Storytelling: Vyntra's...

Scaling Without Breaking ·

2025/11/25

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 choosing challenge over compensation—this conversation is a reminder that scaling is about people long before

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39:33

Fail 40 Times, Build a Hit: The SESH Story | Pepe del...

Scaling Without Breaking ·

2025/11/11

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 the music industryBuilt SESH from zero network and zero revenue to a thriving global companyScaled back

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40:32

Making HOAs Loved Again: The AI-Native Approach to...

Scaling Without Breaking ·

2025/10/28

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 triple revenue while cutting headcount and keeping customers happier than ever. From onboarding “Agent

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42:11

Introducing Scaling Without Breaking | EP 101

Scaling Without Breaking ·

2025/10/15

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 business without burning out or losing control. Whether you're a startup founder, operator, or investor, this

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0:39

Scaling Without Breaking Podcast

Scaling Without Breaking ·

2025/10/15

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 yourcompany’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

en-us

18 results

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