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Heresy

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Categories
Country
United States
This podcast has
28 episodes
Language
English
Explicit
No
Date created
2017/04/26
Latest episode
2026/04/02
Average duration
65 min.
Release period
185 days

Description

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.

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The Moment AI Became Smarter Than The People Building It | Peter Nixey
2026/04/02
Most developers saw AI as a tool. Peter Nixey saw it as a warning sign.Three years ago, Peter wrote a post predicting the death of Stack Overflow - before anyone was talking about it. He was right. But his more recent writing hit closer to home: the moment he realized he was no longer directing the AI, he was slowing it down.Peter is a senior developer and advisor who has spent years working at the intersection of startups and software. He helped launch Fyxer, one of the UK's fastest growing AI assistant companies, at a time when OpenAI didn't even have a public API. Today he is building some of the most advanced AI development pipelines in the industry — and quietly questioning where humans fit into all of it.In this conversation, we explore: Why Peter predicted the death of Stack Overflow three years before the traffic data confirmed itHow AI moved from assistant to bottleneck — and why Peter realized he was the problemThe two factory system he built to remove himself from his own workflowWhy most developers are using AI completely wrongThe difference between building what you want and building what people needWhy the next bottleneck in software has nothing to do with codeHow to manage your mind when the future is genuinely impossible to predictFollow Peter Nixey:LinkedIn:   / peternixey  Follow Heresy Podcast:Instagram:   / heresy.pod  LinkedIn:   / the-heresy-podcast  Spotify: https://open.spotify.com/show/1PKWqUf...Apple Podcast: https://podcasts.apple.com/gb/podcast...Follow Dimitar Stanimiroff:LinkedIn:   / stanimiroff  00:00 Introduction01:35 The Stack Overflow prediction05:30 How AI changed the way Peter writes code09:49 Who owns knowledge in the AI era14:29 What made Fyxer work21:05 Why most founders don't want strategy23:25 The moment Peter felt his own value decline29:08 How Peter rebuilt his entire development process33:25 The chaos monkey step37:31 What is still left for humans44:21 AI, COVID and nuclear weapons1:06:01 The phase shift nobody is talking about1:07:18 Optimistic or pessimistic1:08:23 Outro
The Rise and Fall of Stack Overflow — and What AI Changes Next | Jeff Szczepanski
2026/02/12
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.
The Geopolitics of AI: China vs the U.S., Taiwan, Greenland & Global Power
2026/01/20
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
The GTM Reckoning: AI, Job Security, and Why Leaders Are Falling Behind
2025/12/18
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/
Lewis Parker: The Untold Story
2025/12/04
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.
Guy Rubin (Founder & CEO, Ebsta) — Bootstrapping, Exiting, and the Great SaaS Consolidation
2025/10/26
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
Ali Mitchell on Why Europe Struggles to Build $10B Startups — and How to Fix It
2025/10/09
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
Philip Su on Building at Meta & OpenAI — and How to Thrive in the Age of AI
2025/08/04
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.
How Max Altschuler Built Sales Hacker, Scaled Outreach, and Is Rethinking Venture Capital
2025/08/04
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.
E19: The Final Countdown (The End of Heresy.io — and What Came Next)
2020/02/10
This episode originally aired as the final Heresy podcast, recorded shortly after the winding down of Heresy.io — our sales software startup. After a last-minute acquisition fell through, we had no choice but to begin closing the company. In this episode, I sit down with my co-founder Svilen and our first hire Jack Otis Barker (frontend engineer) to reflect on the journey: The highs and lows of startup life The things we got right (and wrong) What we’d do differently if we had the chance Why we still wouldn’t trade the experience for anything We’ve since relaunched the Heresy podcast with a broader focus on scaling, selling, and building in tech — but we’re keeping this episode up as a time capsule of sorts. 💥 It’s raw, it’s real, and it was never meant to be the end.
Heresy E18 - Farlan Dowell, VP Sales @ CleanShelf on $0 to $10M in ARR 🚀
2019/09/04
In this episode of the Heresy podcast, Dimitar speaks to Farlan Dowell. Farlan is a sales pro & leader, but in reality what he brings is much more comprehensive approach to repeatable revenue. He has 15 years of startup experience in early stage B2B Saas companies. He currently serves as VP Sales at CleanShelf. Previously he was the VP of Sales at RainforestQA, where he increased ARR from $300k in founder-led sales to $10M ARR, increased ACV from 10k to ~100k, and built a 25-person sales team that continues to grow. In the past he’s held positions as the VP of Sales at Upsight and most recently has consulted for a number of companies including Replicated, Test.ai, and Kloudless. He’s interested in helping early teams find product market fit and scale rapidly while avoiding common mistakes developer companies make.
E17: Andrus Purde (Founder @Outfunnel, Ex-CMO @Pipedrive) on Why Cold Email Is Dying & How to Pick the Right Marketing Channel
2019/08/22
In this episode of the Heresy podcast, Dimitar is joined by Andrus Purde — founder of Outfunnel and former CMO at Pipedrive. With over 20 years of experience across companies like Skype and Pipedrive, Andrus has seen it all when it comes to digital marketing and growth. But lately? He’s had enough of cold email. Tune in to hear: Why Andrus believes we're slowly killing email as a channel His personal framework for picking the right marketing channel for your business Lessons from scaling Pipedrive’s user acquisition from the ground up What most early-stage founders and marketers get wrong about demand generation 🔥 A must-listen for anyone building go-to-market from scratch or rethinking how they reach prospects.
E16: Josh Allen, CRO @Drift — What It’s Really Like to Scale from $40M to $400M
2019/05/09
On this episode of the Heresy podcast, Dimitar is joined by Josh Allen, Chief Revenue Officer at Drift. Josh shares his journey through tech — from LogMeIn and CarGurus to leading Drift’s revenue engine — and offers a candid, no-fluff take on what managing hyper-growth really feels like. Tune in to hear: What it takes to scale from $40M to $400M Why it’s totally normal to feel like your “hair is on fire” Hard-earned lessons on leadership, pressure, and pace Practical advice for navigating the chaos of scale
E15: Jeremey Donovan on 5x-ing Reply Rates and Sales Engagement That Works
2019/04/16
In this episode, Dimitar speaks with Jeremey Donovan, SVP of Sales Strategy at SalesLoft — the world’s leading sales engagement platform. Jeremey brings a data-driven perspective to modern sales outreach and shares actionable tactics you can implement immediately, including: How long your emails actually should be The subject lines that get opened (and why) How to achieve up to 5x higher reply rates Where and how to use video to break through the noise Practical tips for SDRs, AEs, and Sales Enablement pros Whether you're building a sales motion from scratch or fine-tuning a mature machine, this episode is packed with insight.
E14: Jason Lemkin’s No-BS Guide to Building a SaaS Sales Machine
2019/03/14
Jason Lemkin — SaaStr founder, serial entrepreneur, and investor — joins Dimitar for a candid, practical deep dive on building a high-performing SaaS sales engine. First, hear Jason’s story — from his early career and first two exits to the hard lessons learned along the way.Then get actionable advice on: Why founder-led sales is critical The importance of closing your first 10 deals before hiring salespeople What to look for (and avoid) in your first Account Executives When and which type of VP Sales to hire Whether to hire VP Sales or VP Marketing first When to start building your Customer Success team Jason’s top sales tips to scale fast and smart If you’re serious about scaling SaaS sales, this episode is a must-listen.

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