Breakthrough AI Operators

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: matt@markup.ai
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
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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
02:30 – Sven Sabas on the most expensive build-vs-buy mistake he’s seen
06:45 – Why engineers default to building—and why it backfires
09:15 – Opportunity cost: the real price no one calculates
11:00 – Junior vs mid vs senior decision-making patterns
14:20 – The explosion of SaaS tools and “shadow IT”
17:40 – Why most companies don’t actually know what they’re paying for
21:10 – Thinking about your tech stack as a system, not a list of tools
24:00 – Serving customers without becoming a custom software shop
27:30 – Staying unbiased in a pay-to-play software world
30:00 – Productivity, leverage, and managing time as a founder
32:30 – Career lessons from hypergrowth and constant reinvention
40:00 – Mentorship, giving back, and long-term impact
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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#ScalingWithoutBreaking #SvenSabas #TechStack #BuildVsBuy #StartupLeadership #FounderLife #SaaS #Operations #Leadership #StartupPodcast

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
00:39 — The Walmart pitch that changed everything
01:12 — Building AI negotiation agents before it was cool
02:05 — Why 95% of AI initiatives fail—and why it doesn’t worry Kaspar
03:26 — Digital workforces + leveling the supplier playing field
05:16 — How AI is reshaping procurement at scale
06:26 — Founding story: from e-Residency to AI negotiations
08:15 — The Walmart negotiation—and what founders get wrong
10:10 — Non-linear negotiations & the myth of zero-sum deals
12:12 — Managing thousands of parallel negotiations
13:05 — Go-to-market strategy & landing enterprise early
14:45 — ICP discipline and the psychology of sales teams
16:02 — Hunters vs. farmers—when to split the sales org
17:12 — The shocking size of Factum’s marketing team
18:40 — Why the founder still needs to meet customers
20:05 — Avoiding “founder escalation chaos”
21:11 — Product vision: when (and how) to hire a CPO
23:18 — Europe vs. US founders—go-to-market mindsets
24:44 — How much should founders pre-sell?
26:19 — Driving internal AI adoption
27:46 — Creating a culture where people embrace agents
29:08 — The surprising internal use cases
30:03 — Estonia vs. US: building globally
31:22 — Remote culture done right
32:55 — Energy, trust, and the 90-day reset
33:19 — Childhood, Estonia, and early entrepreneurial patterns
35:19 — Family bankruptcy, tech, and resilience
36:28 — Fatherhood, Ironman training & CEO performance
38:11 — Creativity, mental space & leadership
39:56 — Books and influences
40:43 — How to reach Kaspar
41:23 — Closing thoughts
A masterclass for founders, operators, and anyone trying to scale without breaking.
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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
02:56 – Why spreadsheets aren’t the problem—communication is
04:22 – Getting non-storytellers to tell powerful stories
05:42 – A clash between engineer + PM that turned into a breakthrough
07:47 – The gift of seeing different realities inside one team
09:06 – What being a “professional foreigner” teaches leaders
11:23 – What great HR leaders understand that others miss
13:30 – When founders challenge HR (and why that’s good)
16:56 – Coaching founders through their first reduction-in-force
19:14 – Worst practices during layoffs
20:14 – Building an alumni network after tough moments
21:56 – Why people matter differently in scale-ups
22:46 – Purpose-driven hires vs. corporate hires
24:35 – Burnout, passion, and work-life reality in tech
25:56 – How engineers chose “kindness” as a core value
28:13 – Building a job-description wizard with AI in 90 minutes
32:16 – Volunteering with unhoused jobseekers (and what resilience really looks like)
35:22 – Growing up between worlds
41:17 – The first person who truly needed her help
42:11 – How a boss changed her entire career trajectory
43:51 – What her younger self would think of who she became
45:21 – Where to find Gerlinde + roles Vyntra is hiring for
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.
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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.