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/

Matt's Books on Amazon

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

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#ScalingWithoutBreaking #MattBlumberg #StartupLeadership #FounderGrowth #CEODevelopment #ExecutiveCoaching #CompanyBuilding #Leadership

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

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#ScalingWithoutBreaking #B2BSales #PreSales #RevenueLeadership #StartupScaling #GoToMarket #SaaSSales #SalesEngineering #TechLeadership #FounderJourney

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 biggest killer of momentum. We also unpack why senior leaders stop chasing clever systems and start focusing on simplicity, integration, and leverage.

Key Discussion Points

• 00:00 – Why tech decisions quietly break scaling companies

If you’re scaling a team, drowning in SaaS tools, or questioning whether your tech stack is helping or hurting—this one will feel uncomfortably familiar.

If this conversation with Sven made you rethink how you’re building:

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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 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 customer, how founders should think about ICP discipline, the mechanics of scaling a global org across Estonia, Europe, and the US, and why freeing up mental bandwidth may be the most underrated executive skill in the AI era.

Kaspar also opens up about fatherhood, burnout-proof leadership, and the unexpected truth about work-life performance when you’re running a 100M-funded scale-up.

KEY DISCUSSION POINTS

• 00:00 — Welcome to Scaling Without Breaking

A masterclass for founders, operators, and anyone trying to scale without breaking.

Don’t forget to:

👍 Like if the conversation sparked new ideas

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#AIProcurement #EnterpriseAI #StartupLeadership #ScalingCompanies #Automation #DigitalWorkforce #FounderStories #GoToMarketStrategy #ProcurementTech #AITransformation #LeadershipDevelopment #B2BTech #FutureOfWork

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 it’s about process.

Episode Breakdown

• 00:00 – Why storytelling makes OKRs actually work

Building culture isn’t about adding more processes—it’s about adding more meaning. If this episode helped you rethink how you lead, communicate, or scale, share it with someone shaping a team of their own.

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#CultureLeadership #OKRs #StorytellingInBusiness #ScaleUpLife #PsychologyAtWork #LeadershipDevelopment #TechCulture #FintechLeadership #FoundersJourney #StartupCulture #PeopleAndCulture #BusinessStorytelling #ResilientLeadership

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 industry

Built SESH from zero network and zero revenue to a thriving global company

Scaled back from 48 employees to a lean, AI-powered team of 12—without losing growth momentum

Disrupted the industry by giving artists true visibility into their fans and communities

It’s a story of resilience, reinvention, and radical focus on product over prestige.

Listen now for real talk on failure, scaling smart, and what it takes to turn “no connections” into your ultimate edge.

Enjoying the conversation?

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#StartupGrowth #MusicIndustry #FanCommunities #Leadership #Entrepreneurship #ScalingWithoutBreaking #RolandSiebelink #PepeDelRio #sesh #FounderJourney #StartupPodcast

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 Steven” to autonomously catching phishing scams, this conversation uncovers how the future of work is already here.

Key Takeaways:

● How Daisy became an AI-native company from day one

● The truth about AI-human collaboration in real operations

● Why traditional property management is ripe for disruption

● How to build a positive, evolving company culture in a fast-scaling startup

● What autonomous buildings could look like by 2030

If you’re a startup founder, tech innovator, or builder of the future, hit Subscribe and turn on notifications. You should not miss another deep dive into scaling, leadership, and technology that actually works.

Main Topics Discussed

00:02 – 01:41 Introduction of Yotam and Daisy

01:44 – 04:30 AI Agents in Daisy

04:30 – 05:36 “AI Native” Companies

05:36 – 08:20 Day in the Life of an AI Agent (“Agent Steven”)

08:20 – 10:23 Human + AI Collaboration

10:27 – 12:27 Scaling Challenges

12:27 – 13:59 Operational Bottlenecks

13:59 – 15:29 Expansion Strategy

15:29 – 17:31 Customer Growth and Market Demand

17:31 – 18:54 Community Building

19:11 – 20:41 Customer Personas

20:41 – 21:36 Industry Fragmentation and Future Growth

21:36 – 23:14 Managing Global Teams

23:14 – 26:32 Tech Decisions and AI Stack

26:32 – 29:43 Origin Story of Daisy

29:43 – 31:19 Early Challenges and First Clients

31:37 – 33:16 Vision for 2030

33:16 – 35:51 Yotam’s Background

35:51 – 37:18 Entrepreneurial Traits

37:43 – 39:12 Leadership Style

39:12 – 42:11 Core Values

42:11 – 43:33 Source of Positivity

43:54 – 44:39 Parenting Lessons in Leadership

44:45 – 45:29 How to Contact Yotam

Connect on LinkedIn: Yotam Cohen, CEO and Co-founder of Daisy

Website: joinDaisy.com

#AIStartup #PropertyManagement #PropTech #AITransformation #StartupGrowth #RealEstateInnovation #AutonomousBuildings #TechDisruption

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 episode offers valuable lessons on building companies that thrive sustainably.

⏱️ Timestamps

00:00 – Welcome to Scaling Without Breaking

00:26 – What this show is all about

01:04 – Turning the tables: producer Nick interviews Roland

02:09 – The toughest stage of startup growth

03:18 – When success starts breaking what worked before

04:14 – Who this podcast is for

05:34 – The hiring trap: startup vs. corporate mindset

07:12 – Practical lessons for founders in chaos

08:35 – The challenge of making success repeatable

11:27 – Lessons from Amazon’s management style

12:17 – Meet the guests: founders, investors, and advisors

13:38 – The paradox of focus after raising funding

15:17 – Defining real startups vs. lifestyle businesses

17:48 – Why founders pivot instead of quit

20:06 – Balancing vision with pragmatism

21:02 – Future guests and expert perspectives

23:17 – Why outside advice matters when scaling

24:20 – Roland’s origin story and early career

26:20 – Lessons from Europe’s first broadband launch

29:37 – Becoming a coach for scaling startups

31:01 – Childhood roots of leadership

33:29 – Founders, growth, and the courage to change

35:11 – Family influences on leadership

38:07 – Lessons from Roland’s parents’ business

40:36 – Emotional reflections and insights

41:00 – Where to find the podcast and resources

🎧 About the Show

Scaling Without Breaking is the podcast for startup leaders who want to grow smarter, not harder. Each week, you’ll hear real stories, strategies, and solutions from founders, operators, and advisors who’ve scaled through the chaos — and learned how to lead like a CEO.

👉 Subscribe now

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. They’ll share the hard lessons, team meltdowns, and systems that actually worked. If you’re tired of vague advice and ready to build something that runs without constant firefighting, this one’s for you.