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.

All built before meaningful customer feedback.

The result?

Months-long release cycles.

Because the real challenge of building a startup isn’t just building it right.

It’s building it fast enough to matter.

Everything changed when Glenn made a critical shift:

Ship every week.

In this episode, Roland and Glenn unpack what it takes to build and scale field service management software without getting trapped in unnecessary complexity.

Key Discussion Points

00:45 - Over-engineering + slow shipping problem

For founders building SaaS products — especially in field service scheduling software, service inspection software, and work order management — this episode offers a practical perspective on scaling without slowing down.

Fieldmagic is offering listeners a 30-day free trial plus a free consulting session.

Learn more here:

👍 Like if this changed how you think about product velocity

#ScalingWithoutBreaking #FieldServiceManagementSoftware #StartupLeadership #ProductDevelopment #FounderMindset #SaaS #GoToMarket #OperationalExcellence

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.

Instead, the conversation explores objective emotional measurement — using science and AI to uncover signals that traditional methods often miss.

Because the real challenge in mental health isn’t just access.

It’s accuracy.

In this episode, Roland and Bechara unpack what it takes to build and scale mental health technology and digital therapeutics with global potential.

Key Discussion Points

For founders building in AI, healthtech, or global platforms, this episode offers a new perspective on scaling innovation responsibly.

Mobio is also offering listeners access to a limited release of its latest platform.

Sign up here:

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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 founders face when every decision can shape the future of their company.

No perfect playbook.

Instead, the conversation focuses on making high-stakes bets, navigating uncertainty, and thinking clearly when the answers aren’t obvious.

Because the real challenge of building a startup isn’t just growth.

It’s making the right decisions when everything is still unclear.

In this episode, Roland and Anthony unpack what it really takes to navigate founder decision-making, align a strong scaling strategy, and manage resource allocation in the earliest stages of a company.

Key Discussion Points

00:00 – The binary problem founders face at the start

For founders navigating growth, fundraising, or strategic trade-offs, this episode offers a practical lens on decision-making and execution.

SeedLegals is also offering listeners a free consultation.

Book here:

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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 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 scratch.

No protecting outdated processes.

Instead, Erki started breaking things.

Processes.

Because sometimes the only way to transform a company is to dismantle the systems that are holding it back.

In this conversation, Roland and Erki explore what it takes when a founder returns to rescue a business and implement effective company turnaround strategies.

They also discuss how AI transformation in call centers, automation, and new operating models could reshape the telemarketing industry.

Key Discussion Points

00:00 – Why Erki wasn’t surprised when he returned

For founders, operators, and leaders thinking about workforce optimization automation, AI disruption, or business reinvention, this episode offers a candid look at what real transformation requires.

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He spent nearly three-quarters of his $16M in funding.

Not on bad hires.

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.

And when you’re selling mission-critical infrastructure software, engineers don’t just swipe a credit card and hope for the best.

Neil finally pivoted:

We also unpack:

This is an honest conversation about expensive mistakes, painful pivots, and what it really takes to scale enterprise software.

If you’re building in SaaS, infrastructure, or enterprise tech — this episode will challenge how you think about go-to-market.

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#ScalingWithoutBreaking #FounderLedSales #StartupLeadership #EnterpriseSales #SaaS #GoToMarket #FounderMode #BusinessGrowth

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 scale isn’t growth.

It’s staying coherent while you grow.

In this conversation, we unpack what it actually takes to scale distribution, partnerships, and merchant relationships without fracturing your culture or overwhelming your team.

Key Discussion Points

00:00 – Why headcount isn’t the answer to scale

If you’re scaling marketplaces, fintech platforms, SaaS ecosystems, or merchant networks, this episode will challenge how you think about growth.

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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 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 enterprise customers, designing workflows that adapt without customization chaos, and building a team that understands customers deeply—not just tickets and specs.

00:00 – Why most teams break as they scale

If you’re a founder or operator navigating enterprise complexity, metadata debt, or the pressure to “just make this one exception,” there’s a lot here for you.

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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 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 product, and what it actually looks like to scale slowly, intentionally, and sustainably—especially in a world being reshaped by AI.

If you’re a founder or operator questioning the “faster is better” narrative, there’s a lot here that will challenge your assumptions.

Key Discussion Points

If this conversation made you pause, rethink, or reflect:

Hit like so more builders find it

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Pass it along to someone building the long game

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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 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 the moments where he nearly broke himself—and the frameworks he developed to avoid breaking again.

This is a practical, honest discussion about feedback, coaching, leadership teams, boards, and why scaling yourself is the hardest (and most important) work a founder can do.

Key Discussion Points

00:00 – Why companies really break as they scale

01:40 – What “breaking” looks like for a CEO

03:00 – Matt Blumberg’s near-breaking moment as a first-time CEO

04:20 – Why getting a coach changed everything

07:40 – The real meaning of “scaling yourself”

09:55 – Why the 30–100 employee stage is so dangerous

11:40 – The two teams every CEO must scale: leadership & board

14:05 – How to actually invest in leadership team growth

16:40 – Coach vs mentor vs peer group (and why all three matter)

18:00 – How to ask for, process, and act on feedback

21:00 – Why operating systems become the company’s lifeblood

23:40 – When leaders must stop telling and start asking

26:00 – Why boards need to scale too

28:00 – Why being a student of the craft never stops

About Matt Blumberg

• LinkedIn: https://www.linkedin.com/in/blumbergmatt/
• Email: [email protected] 
• Personal Blog: https://startupceo.com (22 years of CEO insights)
• Company: https://markup.ai 

Matt's Books on Amazon

• Startup CEO: https://www.amazon.com/s?k=startup+ceo+matt+blumberg 
• Startup Boards: https://www.amazon.com/s?k=startup+boards+matt+blumberg
• Startup CXO: https://www.amazon.com/s?k=startup+cxo+matt+blumberg

Before you go:

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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 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 for years, how manual POC processes quietly destroy win rates, and what changes when you stop trying to avoid technical evaluations and start using them as a competitive advantage.

If deals keep stalling late, or “technical evaluation” feels like a black hole, this one will hit close to home.

Key Discussion Points

00:00 – Why “avoid the POC” became sales dogma

02:05 – The real reason POCs fail (and it’s not the buyer)

03:27 – How most teams still run POCs today

05:34 – Why POCs are no longer optional in modern buying

07:53 – The hidden revenue cost of unmanaged evaluations

10:32 – Turning POCs from a liability into leverage

12:07 – Where POCs actually go off the rails

15:19 – Why pre-sales were ignored for 30 years

18:24 – Early-stage vs. mid-stage CEO reality

20:29 – What lack of focus really does to a company

23:08 – Making decisions for where you’re going, not where you are

26:48 – Building a career by following great people

29:13 – Why most sales engineers struggle as AEs

30:34 – What true category leadership looks like

32:49 – Educating a market that doesn’t know it has a problem

44:55 – Where to learn more about Provarity

If this conversation sparked something:

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