Heresy

Dimitar Stanimiroff

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.

  1. The Rise and Fall of Stack Overflow — and What AI Changes Next | Jeff Szczepanski

    12 FEB

    The Rise and Fall of Stack Overflow — and What AI Changes Next | Jeff Szczepanski

    Stack Overflow went from a scrappy side project to the backbone of modern software development — and sold for $1.8B along the way. Today, many are questioning its future. So what really happened? In this episode, I sit down with former Stack Overflow COO Jeff Szczepanski to unpack how the company scaled from community to global platform, why it pivoted into enterprise SaaS, what drove the Prosus acquisition — and why traffic is now falling in the age of AI. We also explore the bigger picture:Are LLMs replacing developer communities? Is programming still a viable long-term career? Are we in another tech bubble? And who wins — and loses — in the AI era. A candid insider conversation on one of the most influential platforms in tech, and what its story tells us about what comes next. 👇 Timestamps & Resources below 👇00:00 Trailer & Introduction01:36 How Stack Overflow Became an “Overnight” Success06:30 The Founders’ Edge: Why Spolsky & Atwood Won10:15 Turning a Developer Community into a $1B Business17:19 “Facebook or Yammer?” — The Pivot to Enterprise SaaS22:45 The Birth of Stack Overflow for Teams28:40 How to Build a World-Class Online Community37:12 Why Monetising “Fly-By” Users Doesn’t Work43:56 Why Prosus Bought Stack Overflow ($1.8B Deal Explained)52:35 Is Stack Overflow Dead? Did AI Kill It?1:00:26 Can LLMs Survive Without Human-Generated Code?1:04:10 Is Programming Still a Viable Career in the Age of AI Agents?1:07:09 Are We in Another Dot-Com Bubble?1:13:29 Winners and Losers of the AI Race🔔 Don’t forget to subscribe for more unfiltered convos on technology, business, and defying the status quo.

    1h 19m
  2. The Geopolitics of AI: China vs the U.S., Taiwan, Greenland & Global Power

    20 JAN

    The Geopolitics of AI: China vs the U.S., Taiwan, Greenland & Global Power

    AI is no longer just a technology story — it’s a geopolitical one. In this episode, I’m joined by Hung Lee, creator of Recruiting Brainfood, to unpack how AI is reshaping global power. We explore why Greenland has suddenly become strategically critical, why Taiwan and TSMC sit at the heart of the U.S.–China rivalry, how China’s AI strategy differs fundamentally from America’s, and why energy policy, EVs, and rare earths may matter more than algorithms themselves. We also examine why Russia is falling behind, why Europe is struggling economically, and whether representative democracy creates long-term disadvantages in an era of technological competition. This is a wide-ranging conversation about power, incentives, systems, and the future world order. CHAPTERS 00:00 — Introduction01:18 — Venezuela, Maduro & the ew global order06:30 — Greenland, rare earths & strategic leverage17:00 — Taiwan, TSMC & the semiconductor choke point32:50 — Tariffs, trade & industrial policy failures37:30 — China vs U.S.: two very different AI strategies56:50 — Energy, EVs & AI infrastructure01:06:30 — Russia, Europe & structural decline01:24:30 — Final reflections === Follow Us On: YouTube: https://www.youtube.com/@HeresyPodcast Instagram: https://www.instagram.com/heresy.pod

    1h 27m
  3. The GTM Reckoning: AI, Job Security, and Why Leaders Are Falling Behind

    18/12/2025

    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 companies The coming retention crisis for AI-native businesses How Pavilion grew from a small dinner club into the SaaS industry’s barometer Why showing up, doing things that don’t scale, and telling a story are now non-negotiable The uncomfortable truth about job security and running outdated GTM playbooks If 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/

    1 hr
  4. Lewis Parker: The Untold Story

    04/12/2025

    Lewis Parker: The Untold Story

    In this episode, Dimitar sits down with Lewis Parker, one of the most influential figures in UK Hip-Hop and a pioneer of sample-based, cinematic production. Lewis opens up about his early journey into Hip-Hop, the golden era of sample digging, and how he developed his unmistakable sound long before producing for hip-hop legends like Wu-Tang's Ghostface Killah. We explore the rise of UK rap in the 90s, the challenges artists faced with major labels, and why so much of that era’s music ended up left-field and underground. Lewis also talks about the impact of Star Wars, Jedi philosophy, and The Force on his creative process, as well as his move from London to Queens, NYC. The conversation goes deep into craft, culture, and the future:– How Lewis approaches beats, drums, and storytelling– Working with Lord Finesse, Jehst, and other legends– Surviving the music industry as an independent artist– The role of AI in music, creativity, and short-form content– The evolution of Grime, Drill, and the essence of Hip-Hop today This is one of the most honest and insightful conversations about Hip-Hop, creativity, and staying true to your art. A must-listen for fans of UK Hip-Hop, producers, beatmakers, and anyone who cares about the culture.

    1h 36m
  5. Guy Rubin (Founder & CEO, Ebsta) — Bootstrapping, Exiting, and the Great SaaS Consolidation

    26/10/2025

    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

    1h 21m

  6. 09/10/2025

    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 startups What the best founders get right about distribution and go-to-market How to raise VC capital the right way (and what most get wrong) Why Ali still believes in founder intuition — even in the age of AI A 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

    1h 4m

  7. 04/08/2025

    Philip Su on Building at Meta & OpenAI — and How to Thrive in the Age of AI

    Philip Su is an engineer and leader who helped build Microsoft, Facebook, and OpenAI from the inside. In this episode, he shares hard-earned lessons on thriving in the AI era — and staying human through it all. We cover: How AI is reshaping software careers (and what to do about it) Why “good enough” is no longer safe The dangerous gap between exponential tech and human systems Burnout, identity, and what working in an Amazon warehouse taught him The rise of agentic tools, LLMs, and what CS students need to know now Whether you’re an engineer, founder, or future-oriented thinker, this conversation will challenge your assumptions — and help you find a better path forward.

    1h 23m

  8. 04/08/2025

    How Max Altschuler Built Sales Hacker, Scaled Outreach, and Is Rethinking Venture Capital

    Max Altschuler (Sales Hacker, Outreach, GTMfund) joins us in London to talk about building category-defining companies, investing in breakout startups, and rethinking how venture capital works. We go deep on: Lessons from scaling Outreach with Manny Medina The birth of Sales Hacker and the GTMfund story How AI is reshaping go-to-market motions Why GTM is the last true moat in SaaS The tension between being a founder vs fund manager How Max picks winners—and his take on “The Death of VC” This is a must-listen for operators, founders, and anyone navigating the future of SaaS, sales, and startup investing.

    1h 9m
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Ratings & Reviews

3.3
out of 5
4 Ratings

About

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.

Information

  • Creator
    Dimitar Stanimiroff
  • Years Active
    2017 - 2026
  • Episodes
    27
  • Rating
    Explicit
  • Copyright
    © Dimitar Stanimiroff
  • Show Website
    Heresy