Scaling Without Breaking

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. 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 👍 Like if this changed how you think about product velocity 🔔 Subscribe for more honest conversations about growth 💬 Comment with your biggest takeaway 🔗 Share this with a founder building their product #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. 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 👍 Like if this changed how you think about mental health tech 🔔 Subscribe for more honest conversations about growth 💬 Comment with your biggest takeaway 🔗 Share this with someone building in AI or healthtech #ScalingWithoutBreaking #MentalHealthTechnology #DigitalTherapeutics #ObjectiveEmotionalMeasurement #FounderLedSales #ScientistToCEO #HealthTech #StartupLeadership

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. 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/ 👍 Like if this changed how you think about startup decisions 🔔 Subscribe for more honest conversations about growth 💬 Comment with your biggest takeaway 🔗 Share this with a founder navigating critical decisions   #ScalingWithoutBreaking #StartupFunding #FounderDecisionMaking #ScalingStrategy #ResourceAllocation #ProductMarketFit #StartupLeadership #FounderMindset

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. 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

He spent nearly three-quarters of his $60M in funding. 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. 👍 Like if this changed how you think about founder-led sales 🔔 Follow for more honest conversations about scaling 💬 Comment with your biggest takeaway 🔗 Share this with a founder who needs to hear this #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 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 

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. Key Discussion Points 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

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 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

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 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

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: 👍 Support the show if it added value 🔔 Subscribe for more honest conversations about scaling 💬 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

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: 👍 Like the video, so more operators see it 🔔 Subscribe for more honest conversations about scaling 💬 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

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. Don’t forget to: 👍 Like if the conversation sparked new ideas 🔔 Subscribe for more high-caliber founder stories 🔗 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

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. 👍 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

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? ✅ 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. 🔔 Subscribe so you never miss a new episode drop. 📢 Know a founder who needs to hear this? Share it with them. #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.