Heresy
Heresy

Heresy

Dimitar Stanimiroff

Overview
Episodes

Details

Thinkers. Builders. Rebels. Big ideas from the edge of tech and beyond. Hosted by Dimitar Stanimiroff, Heresy started with a simple goal: learn from the sharpest minds in SaaS GTM. It’s grown into a show that follows curiosity across domains—tech, startups, investing, science, and philosophy. Past guests include Jason Lemkin (SaaStr), Aaron Ross (Predictable Revenue), Philip Su (ex-Meta, OpenAI) and execs from Uber, Box, Twilio, and Stack Overflow. New episodes drop regularly.

Recent Episodes

The GTM Reckoning: AI, Job Security, and Why Leaders Are Falling Behind
DEC 18, 2025
The GTM Reckoning: AI, Job Security, and Why Leaders Are Falling Behind
2023 broke the old rules of go-to-market. AI isn’t just changing the tools — it’s rewriting the entire playbook, and most GTM leaders are already behind.In this episode, I sit down with Sam Jacobs, founder of Pavilion, to unpack the seismic shifts shaking SaaS leadership:Why growth has never been harder — even at top-tier tech companiesThe coming retention crisis for AI-native businessesHow Pavilion grew from a small dinner club into the SaaS industry’s barometerWhy showing up, doing things that don’t scale, and telling a story are now non-negotiableThe uncomfortable truth about job security and running outdated GTM playbooksIf you’re a founder, operator, or executive trying to navigate the future of GTM, this conversation is for you.Listen, take notes, and figure out how to stay ahead before it’s too late.👇 Timestamps & Resources below 👇00:00 Trailer – The GTM Reckoning: AI, Power Shifts, and What’s Breaking in SaaS00:54 Why AI-Native Companies Aren’t Playing the Efficiency Game – A Tale of Two Worlds05:18 Why Growth Is So Hard Right Now & Why There’s No Job Security for GTM Execs — Even at Elite Tech Companies09:30 Drivers vs. Passengers – Why So Many GTM Leaders Are Running Outdated, Dumb Playbooks13:30 The Pavilion Origin Story – From a Small Dinner Club to the SaaS Industry’s Unofficial Barometer21:08 “The Road to Hell Is Paved With Good Intentions” – Why You Can’t Build an Exclusive Community and Be Fully Inclusive at the Same Time27:00 The Power of Doing Things That Don’t Scale – Why Showing Up Daily and Being Face-to-Face With the Market Still Wins39:00 The Coming Retention Apocalypse for AI-Native Companies & Why Harry Stebbings’ Incentives Aren’t Aligned With Yours44:32 Are ChatGPT Prompts Actually Well-Intentioned? Or Are They Engineered for Addiction and Product Dependency?47:00 What AI Adoption Really Means for GTM Leaders & How the Role of Executives Is About to Change53:00 Why Storytelling and a Strong Point of View Matter More Than Ever In a World Where Everyone Has the Same Tools🔔 Don’t forget to subscribe for more unfiltered convos on technology, arts, and defying the status quo.Follow Sam:🔗 LinkedIn:   / samfjacobs   🎧 Topline Podcast:    • E120: What does the future of tech look li...   🎙 The Heresy Podcast – conversations with builders, thinkers & rebels 🔔 Subscribe: / @heresypodcast 📱The Heresy Pod on Instagram:   / heresy.pod  🔗 Follow Dimitar: https://www.linkedin.com/in/stanimiroff/
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59 MIN
Guy Rubin (Founder & CEO, Ebsta) — Bootstrapping, Exiting, and the Great SaaS Consolidation
OCT 26, 2025
Guy Rubin (Founder & CEO, Ebsta) — Bootstrapping, Exiting, and the Great SaaS Consolidation
In this episode, I sit down with Guy Rubin, Founder & CEO of Ebsta — the global leader in Revenue Intelligence, recently acquired by Fullcast.Guy shares unfiltered insights from a decade of building, scaling, and exiting a SaaS company that transformed how revenue teams operate.We cover:🚀 Raising Venture Capital vs Bootstrapping — the good, the bad, and the ugly💰 Exits — why selling to the highest bidder isn’t always the best outcome📉 GTM SaaS Consolidation — who’s winning, who’s losing, and why🤖 AI in Sales — how top Go-To-Market teams are using AI to pull ahead🎯 Elite AEs — what separates the best from the rest, and why the gap is wideningWhether you’re a founder, sales leader, Account Executive or SaaS operator, this episode is packed with hard-won lessons from someone who’s lived it all — from bootstrapping to acquisition.👇 Timestamps & Resources below 👇00:00 Episode Highlights & Intro00:02 Why "build it and they will come" never works and why founders should focus on solving "11/10 problems" (not 7/10)00:06 Founder Archetypes 00:08 Why Timing Beats Execution: Ebsta's Inception Story00:11 Doing Product Led Growth before Product Led Growth was a thing00:13 Why Guy chose NOT to raise VC and instead bootstrap the business 00:17 Going head to head with companies that have raised BILLIONs00:22 Delivering value to the C-suite: Pictures Work Better Than Words00:25 VC or Bootstrap: What's Right For You00:28 The great SaaS Consolidation: who’s winning, who’s losing, and why00:38 Advice to founders looking to sell their business 00:40 Why US SaaS companies continue to beat European ones00:45 The Rise Of The 10x Sales Professional 00:52 Why the best path to revenue growth is focusing on Existing Business 00:56 Why are we seeing a return to Full-Cycle Sales 01:02 Leveraging AI to Increase Sales Efficiency 01:10 All Eyes On Ideal Customer Persona (ICP)...and Finance01:16 The future of GTM: Will AI Agents Kill CRM 🔔 Don’t forget to subscribe for more unfiltered conversations on technology, business, and defying the status quo.Follow Guy:🔗 LinkedIn:   / rubinguy   🤖💰 Ebsta – Revenue Inteligence: https://www.ebsta.com/📊 2025 GTM Sales Benchmarks – https://benchmarks.ebsta.com/2025-gtm... 🎙 The Heresy Podcast – conversations with builders, thinkers & rebels 🔔 Subscribe: / @heresypodcast 🔗 Follow Dimitar:   / stanimiroff  
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80 MIN
Ali Mitchell on Why Europe Struggles to Build $10B Startups — and How to Fix It
OCT 9, 2025
Ali Mitchell on Why Europe Struggles to Build $10B Startups — and How to Fix It
Ali Mitchell has backed more than half a dozen unicorns — but his story starts with failure.Before co-founding Huddle and later leading EQT Ventures, one of Europe’s most successful VC funds, Ali was a founder who learned firsthand how hard it is to build and scale. In this episode, we unpack what those early failures taught him about resilience, product-market fit, and what separates great founders from good ones.We also dive into:Why Europe still struggles to produce $10B startupsWhat the best founders get right about distribution and go-to-marketHow to raise VC capital the right way (and what most get wrong)Why Ali still believes in founder intuition — even in the age of AIA conversation about hard lessons, second acts, and the patterns behind six unicorns.🎙️ Heresy is a podcast about people who defy conventional wisdom — founders, investors, and thinkers reshaping how technology gets built and scaled.👇 Timestamps & Resources below 👇00:00 – Trailer01:01 – Ali’s Early Journey and Entrepreneurial Roots05:32 – Building and Scaling Huddle14:27 – Go-to-Market Lessons and Missteps22:18 – Why Europe Struggles with Commercialization27:56 – From Founder to Investor: Lessons from EQT Ventures36:14 – The Cultural Contrast: US vs. Europe43:40 – What the US Gets Right: Selling, Storytelling, and Scale48:54 – The Tuck Shop Story: Teaching Entrepreneurship Early50:06 – Returning to Europe: Family, Values, and Purpose51:56 – From EQT to Odyssey: A New Mission for European Tech54:51 – Flow and the New Era of Engineering Automation56:00 – Odyssey’s Investment Focus: AI + Automation in the Real World57:30 – Lessons for Founders: Ambition, Focus, and Resilience59:41 – What Most People Get Wrong About Venture Capital01:02:31 – Final Advice for First-Time Founders01:03:41 – Closing Thoughts🔔 Don’t forget to subscribe for more unfiltered conversations on technology, business, and defying the status quo.Follow Ali:🔗 LinkedIn:   / alimitchell   💰 Odyssey Ventures: https://www.odyssey.ventures/🎙 The Heresy Podcast – conversations with builders, thinkers & rebels 🔔 Subscribe:    / @heresypodcast   🔗 Follow Dimitar:   / stanimiroff   #Ali Mitchell #EQT Ventures #startups #venture capital #founders #SaaS #Europe #tech #VC #Heresy Podcast #DimitarStanimiroff #growth #failure #unicorns #scaling #productmarketfit #fundraising
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64 MIN