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