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 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 03:35 - Shift to weekly releases + impact on customers 05:20 - Product positioning (field service + inspections) 08:00 - GTM learning + advisors 10:13 - ICP mistake + Gartner lead issue 12:43 - Shift to outbound + ICP clarity 14:18 - Junior devs + shipping culture 16:09 - AI + role of juniors 21:57 - Founder advice

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: fieldmagic.co/midstage

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

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 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 00:06 – From neuroscientist to building objective psychiatry 01:23 – Can a selfie measure emotions better than self-reporting? 02:41 – Why objective biomarkers outperform subjective data 03:39 – How Mobio’s platform delivers personalized therapy 05:26 – “Exercise for the brain” and expanding use cases 06:34 – Self-guided vs. provider-supported mental health care 07:22 – Business model across different healthcare systems 08:37 – Market expansion strategy: US, Canada, Singapore, India 09:17 – Why the founder is still the best dealmaker 09:44 – Rethinking sales: supporting founder-led sales instead of hiring more closers 10:46 – Scaling globally: serving both large institutions and individual practitioners 11:49 – Universal biomarkers vs. culturally localized therapy 13:16 – Childhood, freedom, and shaping leadership style 14:49 – What leadership actually requires beyond decision-making 16:12 – Leading with empathy (and “not nice” traits used for good) 17:07 – Advice for founders without a business background 18:52 – Choosing investors and protecting company culture 20:09 – Making the platform accessible to everyone

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: https://forms.gle/TRFjwKpwryThfJjSA

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#ScalingWithoutBreaking #MentalHealthTechnology #DigitalTherapeutics #ObjectiveEmotionalMeasurement #FounderLedSales #ScientistToCEO #HealthTech #StartupLeadership

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 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 02:15 – Making bets that determine a startup’s future 05:10 – Leveraging teams to sharpen decisions 08:20 – The misalignment between founders and investors 11:35 – Rethinking startup funding and the rise of seed strapping 15:00 – Balancing speed vs. conviction in decision-making 18:25 – Finding product-market fit without overbuilding 22:10 – Allocating limited resources for maximum impact 26:40 – When to double down vs. change direction 30:05 – The evolving role of founders as companies scale

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: https://seedlegals.com/talk-to-an-expert/

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#ScalingWithoutBreaking #StartupFunding #FounderDecisionMaking #ScalingStrategy #ResourceAllocation #ProductMarketFit #StartupLeadership #FounderMindset

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. No maintaining comfortable leadership structures. No accepting “this is how we’ve always done it.”

Instead, Erki started breaking things.

Processes. Management layers. Bureaucracy.

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 02:25 – The risks of leadership staying too long in one company 04:43 – Why breaking systems can unlock growth 07:00 – Eliminating bureaucracy and unnecessary processes 08:25 – Why human calls may outperform AI-driven outreach 10:49 – The telemarketing CPO model and incentive alignment 12:10 – Using call transcripts and AI insights to generate new revenue 14:04 – Why human connection still matters in an AI world 15:52 – Why large companies are now moving like startups 17:42 – The emerging role of CEOs as builders and rapid prototypers

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.

👍 Like if this changed how you think about company turnarounds 🔔 Subscribe for more honest conversations about growth 💬 Comment with your biggest takeaway 🔗 Share this with someone leading a business transformation

#ScalingWithoutBreaking #CompanyTurnaroundStrategies #FounderReturnsToRescueBusiness #AITransformationCallCenter #TelemarketingCPOModel #WorkforceOptimizationAutomation #StartupLeadership #FounderMindset

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 don’t just swipe a credit card and hope for the best.

Neil finally pivoted: • Shifted from small $7K deals to true enterprise sales • Replaced transactional salespeople with engineers in pre-sales • Re-centered around founder-led sales • Raised prices • Doubled revenue within 12 months

We also unpack: • Why founders get out of sales too early (and why that’s dangerous) • The cost of being stuck in the “dead zone” of mid-sized deals • How to hire leaders who think like you — without creating tunnel vision • Why churn is more dangerous than missing revenue • How founder mode actually works in practice • And the unexpected hobby that helps Neil unplug (hint: it involves rappelling 2,000 feet underground into abandoned mines)

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

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 02:10 – Building systems that support 8,000 merchants 04:45 – The hidden operational risks of rapid expansion 07:30 – Standardization vs. customization: where to draw the line 10:15 – Designing internal clarity so teams don’t duplicate work 13:40 – Metrics that matter when scaling merchant networks 17:05 – Partner enablement without losing control of the brand 20:22 – Protecting culture while increasing complexity 24:18 – The inflection point: when scale starts to strain the system 28:50 – Leadership maturity required at 8,000+ merchants 33:12 – What founders get wrong about “lean teams” 37:05 – The mindset shift from hustle to architecture

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

👍 Like if this changed how you think about scale

🔔 Subscribe for more honest conversations about growth

💬 Comment with your biggest takeaway

🔗 Share this with someone building with a lean team

#ScalingWithoutBreaking #MarketplaceGrowth #StartupLeadership #OperationalExcellence #FounderMindset #LeanTeams #MerchantGrowth #BusinessArchitecture 

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 01:40 – Serving enterprise customers with a team of 11 03:15 – One product, many workflows (without customization hell) 05:23 – Why everyone on the team talks to customers 07:58 – Building an advisory board that actually adds value 11:14 – The hidden value trapped in archival content 13:55 – Pricing based on volume, not complexity 15:05 – Owning the full workflow end-to-end 17:17 – Partnerships, awards, and non-exclusive growth 19:54 – The hardest challenge: helping customers see their own value 22:31 – Why staying bootstrapped was a strategic choice 24:09 – Long-term growth and exit thinking 26:12 – Courage, problem-solving, and founder mindset 32:01 – Creating autonomy without chaos inside small teams

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.

👍 Like if this challenged how you think about scale 🔔 Subscribe for more honest conversations about growth 💬 Comment with your biggest takeaway 🔗 Share this with someone navigating enterprise complexity

#ScalingWithoutBreaking #StartupLeadership #EnterpriseSaaS #FounderMindset #ProductLedGrowth #Bootstrapped #EonMedia #OperationalExcellence

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

• 00:00 – Why midstage companies face a different kind of struggle
• 01:10 – Introducing Tayfun Bilsel & his work with scaling teams
• 02:55 – What “midstage” really means (and why founders misjudge it)
• 04:40 – The early traction trap: success that creates new problems06:35 – Why what worked before stops working now
• 08:50 – Hiring mistakes that compound complexity
• 10:45 – Organizational debt and invisible drag on growth
• 12:55 – When growth exposes broken processes
• 14:55 – Founder bottlenecks and decision overload
• 16:45 – Letting go of control without losing accountability
• 18:40 – Operating without a clear operating model
• 20:30 – Aligning teams around outcomes, not activity
• 22:35 – Why midstage teams feel busy but stuck
• 24:45 – Decision velocity as a leadership signal
• 26:50 – Cross-functional misalignment and execution gaps
• 28:55 – Scaling culture while raising standards
• 31:00 – Metrics that actually matter at this stage
• 33:05 – Strategy vs. execution: where teams fall apart
• 35:10 – Why founders resist structure (and why it hurts them)
• 37:05 – Building systems that support innovation
• 39:00 – Leadership leverage and focus at scale
• 40:55 – Moving from intuition to repeatability
• 42:50 – What sustainable scale really looks like
• 44:40 – Advice for overwhelmed midstage founders

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

• Hit like so more builders find it

• Subscribe if you care about scaling without chaos

• Share your biggest takeaway in the comments

• Pass it along to someone building the long game

#Bootstrapped #SaaS #FounderStories #StartupLeadership #ScalingWithoutBreaking #B2B #ProductStrategy #CustomerTrust #Entrepreneurship #AIinBusiness #ClientPortalSoftware #VirtualDataRoomSoftware #SecureClientPortal #WhiteLabelProjectManagementSoftware

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

Before you go:

👍 Like this if it resonates

🔔 Subscribe for more real conversations on leadership and scale

💬 Comment with the takeaway that hit closest to home

🔗 Share with someone navigating growth right now

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

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:

👍 Support the show if it added value

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💬 Share the takeaway that challenged your thinking

🔗 Send this to a leader stuck in endless POCs

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

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:

👍 Like the video, so more operators see it

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💬 Share the takeaway that hit closest to home

🔗 Send this to a founder or leader who’s buried in tool decisions

#ScalingWithoutBreaking #SvenSabas #TechStack #BuildVsBuy #StartupLeadership #FounderLife #SaaS #Operations #Leadership #StartupPodcast

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.

Don’t forget to:

👍 Like if the conversation sparked new ideas

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🔗 Share this with a founder or operator who needs to hear it

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

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.

👍 Show some love with a like

🔔 Subscribe for more human-centered business conversations

💬 Share your biggest insight about storytelling or leadership

🔗 Pass this episode forward to someone building a team or culture

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

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?

✅ Follow Scaling Without Breaking for more founder stories that tell the truth behind hypergrowth.

💬 Drop your biggest takeaway or lesson from Pepe’s journey in the comments.

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📢 Know a founder who needs to hear this? Share it with them.

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

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

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.

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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.