Best Bootstrapped Giants Podcasts (2025)

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What Happens When You Move Beyond the Ego 58:18

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17h ago58:18

58:18

What if your biggest source of stress… is your own mind? In this episode of Heart of Entrepreneurship, Jesse and Dave unpack the concept of ego—not as arrogance, but as the mental identity we all unconsciously carry. They explore how identifying with your thoughts creates suffering, limits your potential, and keeps even successful founders from fee…

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How Dan Shipper’s AI-first company built 4 apps 49:02

4d ago49:02

49:02

⏱️ TIMESTAMPS 00:00 – Intro Montage 00:52 – Every’s portfolio: Monologue, Spiral, Cora, and Sparkle 01:48 – How many people use their tools today? 02:15 – Mostly bootstrapped, with a small raise from Reid Hoffman 04:00 – Building based on internal needs and workflows 06:45 – Monologue’s origin story: weekend build, instant love 09:00 – Why Monologu…

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Anger Is a Compass: How Founders Turn Emotion into Clarity 51:50

3d ago51:50

51:50

Anger as a Compass: How Founders Can Use Emotion to Set Clearer Boundaries and Make Better Decisions Most entrepreneurs are taught to suppress anger—or worse, use it as a weapon. But what if anger isn’t something to avoid… but something to listen to? In this episode of The Heart of Entrepreneurship, Jesse and Dave explore how anger, when processed …

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Neil Patel’s AI System for Getting 100 Clients a Week 46:56

10d ago46:56

46:56

⏱️ Timestamps / Episode Guide 00:00 – Intro 01:12 – Why most companies fail to get ROI from AI 02:06 – The #1 mistake: Using AI for content without strategy 03:00 – Fragmented data = wasted AI potential 04:00 – How Neil’s team fixes that: Find what drives revenue first 05:24 – Real case study: Med spas using AI to win back Google traffic 07:00 – Ho…

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The G.O.A.T.s of Kindness on Bootstrapping a Purpose-Driven Company | Dr. Brent Ridge & Josh Kilmer-Purcell 1:01:47

9d ago1:01:47

1:01:47

Most companies talk about purpose. Beekman 1802 made it their operating system. In this episode of The Eric Ries Show, I sit down with Dr. Brent Ridge and Josh Kilmer-Purcell, co-founders of Beekman 1802, to explore how a small act of compassion grew into a multimillion-dollar skincare brand rooted in community and purpose. After losing their Manha…

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Building Mission-Driven Products in Regulated Industries: Lessons from 20 Years in Product Management 33:18

9d ago33:18

33:18

Ever wondered how to navigate product development in highly regulated industries while still driving innovation? Join Amanda and Adam as they chat with Patrick Wesonga, Senior Product Leader, who shares two decades of invaluable product management wisdom. From hypothesis-driven development to building mission-driven products, discover how to balanc…

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Why Following Aliveness Might Be the Smartest Business Move 44:26

16d ago44:26

44:26

How to Follow What Makes You Feel Alive (Even If It Makes No Logical Sense) You’ve probably heard advice like “follow your passion” or “do what lights you up”—but how do you actually do that in practice as a founder? And how do you know when you’re following aliveness vs fear or performance? In this episode, Jesse and Dave dive into the deeper laye…

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Garry Tan: Why Startups Are Scaling to $10M in 20 Months 49:33

17d ago49:33

49:33

⏱️ Timestamps / Episode Guide 00:00 – Intro 00:46 – Garry Tan on CaseText, early LLMs, and hallucination risk 04:00 – The first AI breakthroughs in legal tech 08:00 – How vertical SaaS outperforms general AI platforms 11:00 – Avoca & HVAC: beating ServiceTitan with niche AI 13:00 – YC startup growth rates: 10%–20% revenue weekly 17:00 – The “startu…

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When You Don’t Know What’s Next – You’re Expanding and Growing 50:27

18d ago50:27

50:27

Ever feel stuck as a founder—uncertain about your next move, paralyzed by fear, or second-guessing what you really want? In this episode, Jesse Pujji and Dave Kashen unpack the hidden dynamics behind “stuckness” and how founders can transform it into growth. From reframing “I don’t know” as liberation, to uncovering fear, anger, and desire as power…

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Why Even Billionaires Still Don’t Feel Safe 47:26

23d ago47:26

47:26

Can you build a wildly successful company without sacrificing heart? In this episode, Jesse Pujji and Dave Kashen dive deep into the Sedona Method—a powerful practice for letting go of the endless chase for security, control, and approval. They share personal stories about money, identity, and ambition, and explore how founders can build businesses…

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From Fired CEO to Billion-Dollar Exit: How Lukas Biewald Turned Failure into the Future of AI 1:05:54

23d ago1:05:54

1:05:54

Lukas Biewald has been shaping the future of AI for nearly two decades. In this episode of The Eric Ries Show, we explore how his early passion for the board game Go, his hard-won lessons as a founder, and his focus on alignment and culture helped him build Weights & Biases into a trusted toolmaker in machine learning. In our conversation, we discu…

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Hey. What is this? 2:04

27d ago2:04

2:04

By Andrew Warner

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The Untold Truth About Agency Growth: Why Small Teams Beat Giant Competitors 34:02

1M ago34:02

34:02

From Oracle Sales to Digital Product Pioneer: Building a Sustainable Tech Agency in the Mobile Era.In this episode of How I Grew This, host Adam speaks with Robert Armstrong, Co-Founder and CEO of Appstem, about his 15-year journey building a successful digital product agency from the early days of mobile apps to today's AI-driven landscape, alongs…

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No VC, No Limits! How Bootstrapping Built Manoj "Marty" Pranik’s Global Cloud Giant Atlantic.Net? 1:15:40

1M ago1:15:40

1:15:40

Dorm Room Dreams to Cloud Empire From a dorm room startup to building a global cloud infrastructure powerhouse without venture capital. Marty Pranik, Founder & CEO of Atlantic.Net, shares his story of resilience, innovation, and vision. 🙏 Special Thanks A big thank you to PayPal Stadium, San Jose Earthquakes Press Room, and the entire San Jose Eart…

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Beyond Success: Gagan Biyani’s Inner Journey Building Udemy, Sprig, and Maven 1:15:38

1M ago1:15:38

1:15:38

What does it take to build, lose, and rebuild as an entrepreneur—while staying true to yourself? In this conversation, host Dave Kashen sits down with Gagan Biyani (co-founder of Udemy, Sprig, and Maven) to explore the emotional and practical realities of entrepreneurship: co-founder dynamics, letting go of team members, navigating failure, and mov…

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How to move beyond bureaucracy, not waste talent, and innovate faster | Michele Zanini & Gary Hamel 1:37:17

1M ago1:37:17

1:37:17

Bureaucracy was once a breakthrough. Today, it’s become a costly drag on innovation, human potential, and business impact. In this episode of The Eric Ries Show, I sit down with Gary Hamel and Michele Zanini, authors of Humanocracy, to explore how organizations can move beyond outdated management models and unlock true human thriving. Hamel and Zan…

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How to Change Without Willpower, Guilt, or Discipline 56:08

2M ago56:08

56:08

Ever find yourself stuck in a cycle of self-discipline, shame, and yo-yo habits? In this episode of Heart of Entrepreneurship, Jesse and Dave dive deep into the psychology behind personal growth—and why punishing yourself into change doesn’t actually work. From fitness routines to leadership patterns, they explore how to unlock lasting behavior cha…

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Discover the Power of Podcasting 54:55

2M ago54:55

54:55

Tune to here personal journey of host, from her early days in radio to building a thriving podcasting platform. Pranali dives into the passion, challenges, and lessons learned along the way, highlighting the key benefits of podcasting and how it can ignite your own creative journey. Whether you’re an entrepreneur, startup founder, business owner, o…

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The Parts You Reject Are Blocking Your Potential 48:18

2M ago48:18

48:18

Why You Resist Feeling Bad (And How It Holds You Back as a Founder) ✅ Are you bootstrapping? You need this: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up 00:00 – Intro + today's topic: “shadows” and the parts we deny 01:30 – Jesse’s shadow: the victim 03:00 –…

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The Hidden Blueprint - Customers Who Sell Your Product 53:38

2M ago53:38

53:38

How to Turn Your First Customers into Superfans? Your first customers aren’t just transactions—they’re the foundation of your startup’s growth. In this episode of Bootstrap Banter, uncover strategies most founders overlook when turning early adopters into loyal design partners and superfans. What you’ll learn: Transform your first customers into co…

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From Blacksmith to Billionaire: The Making of Patagonia’s Ethos 1:28:48

2M ago1:28:48

1:28:48

Patagonia has always been different. While so many companies lose their way when profits come before people, the planet, or even their own products, Patagonia continues to stay true to its values. In today’s episode of The Eric Ries Show, I speak with journalist David Gelles, author of Dirtbag Billionaire, his new book about founder Yvon Chouinard.…

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Turning Insights Into Impact: The Art of Strategic Creativity 33:42

2M ago33:42

33:42

In this episode of How I Grew This, hosts Amanda and Adam sit down with Jason White, Head of Acquisition at Policygenius, to explore the evolving landscape of digital marketing and SEO. Jason shares invaluable insights from his journey from a local bike shop to leading acquisition strategies, discussing why traditional marketing principles still ma…

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How Enjoyment (Not Hustle) Drives Real Growth 47:51

2M ago47:51

47:51

7 Inner Shifts That Make You a Better Leader (Without Forcing It) ✅ Are you bootstrapping? You need this: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up 00:00 – Intro: Dave’s coaching lineage + the Groundbreakers retreat 01:30 – Why even high-performing founde…

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The Personas Playing You: How Founders Get Trapped in Drama & Identity 55:21

2M ago55:21

55:21

The Personas Playing You: How Founders Get Trapped in Drama & Identity ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up Show Notes: 00:00 – Intro + why entrepreneurship doesn’t have to be painful 01:30 – What is a persona?…

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“AI Will Break the Internet” — Cloudflare CEO’s Big Prediction 1:18:58

2M ago1:18:58

1:18:58

What if your company’s mission turned out to be bigger than you imagined? In this episode of The Eric Ries Show, I speak with Matthew Prince, co-founder and CEO of Cloudflare, now a $70 billion company defending 20% of all internet traffic. We trace how Cloudflare’s mission wasn’t declared at the start, but discovered through a series of principled…

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Why Unfelt Feelings Become a Prison for Founders 50:28

2M ago50:28

50:28

What Are You Resisting? How Founders Block Growth by Avoiding Emotion ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up Show Notes: 00:00 – Intro + recap: resisting emotions, what it means for founders 02:00 – Why emotions …

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The Answers Are Hiding in Your Repressed Emotions 48:13

3M ago48:13

48:13

Emotions Are Not the Enemy: Unlocking Leadership, Clarity & Decision-Making Through Feeling ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up Most entrepreneurs think their emotions get in the way. But what if they’re actua…

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Inside Vercel: The $3B giant that’s changed coding forever 1:19:17

3M ago1:19:17

1:19:17

In this episode of The Eric Ries Show, I’m joined by Guillermo Rauch, CEO and founder of Vercel—a company powering the front end of the internet for brands like OpenAI, Nintendo, Chick-fil-A, and many more. Guillermo’s journey began far from Silicon Valley, in Argentina, where a Red Hat Linux CD changed the course of his life. We talk about how ope…

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5 Growth Hacks to win your first five customers (No Budget Startup Guide) 54:48

3M ago54:48

54:48

What if I told you 5 game-changing startups never paid for their first customers… and still won? No ads. No funding. No big team. Just one thing they all had in common! Today on Bootstrap Banter, I’m digging into a set of patterns most founders overlook in their early days. And once you see it… you can’t unsee it. This isn’t theory. It’s a decoded …

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Subscription App Growth: Insights from the Frontlines 34:37

4M ago34:37

34:37

Join Adam and Amanda as they sit down with Shumel Lais, a mobile growth expert with over a decade of experience, to explore the essential strategies for launching and scaling subscription apps. From setting up proper analytics and understanding payback periods to navigating iOS challenges and leveraging AI, this episode delivers practical insights …

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Creative Tension: The Secret to Creating Big Results Without the Grind 51:47

4M ago51:47

51:47

Why do some goals drain you while others inspire action? In this powerful conversation, Jesse Pujji and executive coach Dave Kashen unpack a core concept at the heart of entrepreneurship: the Desired Future State (DFS). They explore how clean motivation, grounded in acceptance and vision—not fear or lack—can transform the way you lead, strategize, …

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Motorboat Leadership vs. Sailboat Leadership 41:18

4M ago41:18

41:18

[00:00:00] Intro – Jesse hints at a personal and professional transition [00:00:27] Jesse’s life update – spiritual journey and post-Japan reflection [00:01:30] The Motorboat vs Sailboat leadership metaphor explained [00:02:51] Internal conflict: fear of letting go and team dependency [00:04:03] Overwhelm from managing multiple businesses – “a comp…

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How GitLab scaled to 30M users with transparency, remote work, and the ultimate employee handbook | Sid Sijbrandij 1:33:29

4M ago1:33:29

1:33:29

In this episode of The Eric Ries Show, I’m joined by Sid Sijbrandij, co-founder and Executive Chair of GitLab—one of the world’s most radically transparent and values-driven software companies. Sid shares how GitLab evolved from an open-source side project into a publicly traded DevOps platform, all while remaining deeply aligned with its values. F…

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What really builds a robust business? 54:48

4M ago54:48

54:48

Are you building for likes or for longevity? In this Bootstrap Banter episode, we dive into the game-changing difference between chasing votes (validation) and building real weight (value). If you're navigating noise, distractions, or hype while building your business—this one's for you. 🔍 Learn: ✔️ What truly drives sustainable success ✔️ How to s…

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Is Spirituality the Missing Key for Founders? 46:37

4M ago46:37

46:37

You're Not Your Inner Voice: Meditation, Spirituality, and Mental Clarity for Founders ✅ ARE YOU BOOTSTRAPPING? YOU NEED THIS: https://bootstrappedgiants.com/subscribe ✅ Master the Inner Game of Entrepreneurship here: https://www.davekashen.com/newsletter-sign-up 00:00 – Jesse introduces the topic: spirituality for entrepreneurs 01:00 – What does s…

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Turning down $200 million and the big bets that led to powering 40% of the internet 1:10:48

5M ago1:10:48

1:10:48

In this episode of The Eric Ries Show, I’m joined by Matt Mullenweg, CEO of Automattic and co-founder of WordPress, the open-source platform that now powers 43% of the internet. Recorded on the 20th anniversary of Automattic, our conversation is a deep dive into what it takes to build enduring companies on top of open infrastructure. We explore Mat…

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Close - Focused CRM does $50 million a year 49:11

5M ago49:11

49:11

[00:00:00] Intro – Andrew sets up the conversation: sales reluctance, AI, and CRM evolution [00:00:47] Steli explains Close's positioning: high-communication CRM for salespeople [00:01:41] Revenue milestone: Close is on track to hit $50M this year [00:02:36] Bootstrapping vs. fundraising: why Close chose profitability over VC [00:04:01] Why staying…

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The playbook for fixing toxic culture, pointless friction, and broken systems | Bob Sutton (Stanford, NYT bestselling author) 1:27:34

5M ago1:27:34

1:27:34

In this episode of The Eric Ries Show, I’m joined by Bob Sutton, organizational psychologist and New York Times bestselling author of several influential books on leadership, behavior, and workplace culture, including his latest: The Friction Project. We explore insights from across his body of work, including real-world examples of large organizat…

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The pitch that changed air travel forever: $3B in preorders, Richard Branson’s backing, and the return of supersonic flight | Blake Scholl (Boom Supersonic) 1:26:59

6M ago1:26:59

1:26:59

What does it take to challenge a century-old status quo in aviation? In this episode of The Eric Ries Show, I sit down with Blake Scholl, Founder and CEO of Boom Supersonic, a company on a mission to bring back supersonic air travel—sustainably and affordably. Blake doesn’t come from aerospace. He’s a computer scientist and former Amazon engineer w…

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He's controlling ChatGPT responses 50:56

6M ago50:56

50:56

[00:00:36] Intro: ChatGPT as a traffic driver and Chirag’s early insight [00:01:48] Revenue Numbers and Profitability of Taco [00:02:24] Personal investment strategy and non-AI assets [00:03:36] How Chirag uses AI agents to replace writers and boost efficiency [00:05:42] What makes Taco a true AI-powered agency [00:07:03] Tracking brand rankings in…

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1440 is a Bootstrapped Giant 49:49

6M ago49:49

49:49

[00:00:00] Quick Montage (Growth, Grit, Vision, Revenue, Meaning of 1440) [00:00:36] Intro: Why 1440 is Different [00:01:48] Revenue Numbers and Profitability [00:02:24] How They Funded Without Venture Capital [00:04:48] How Big Can an Email Newsletter Get? [00:05:15] Why They Ignored Advice to “Go Niche” [00:06:09] 1440’s Thesis: Inch-Deep, Mile-W…

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The Hidden Costs of Pay Inequality, And How Leading Companies are Solving It | Maria Colacurcio (Syndio) 1:13:57

6M ago1:13:57

1:13:57

In this episode of The Eric Ries Show, I’m joined by Maria Colacurcio, Co-Founder and CEO of Syndio, a workplace equity analytics platform. Syndio helps companies close pay gaps and build high-trust organizations. Maria has had a long career in leadership, previously co-founding Smartsheet and serving as a senior leader at Starbucks, where she focu…

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Why to build in public? 53:29

7M ago53:29

53:29

What if your startup journey could inspire others before you make it big? In this episode of Bootstrap Banter, I’m breaking down the fears and cultural taboos around sharing your entrepreneurial story while you’re still in the making. Discover why building in public isn’t just brave, it’s a game-changer. With real talk, founder stories, and tips yo…

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Lessons on co-founding Twitter, Medium and Blogger with Ev Williams 1:22:17

7M ago1:22:17

1:22:17

In this episode of The Eric Ries Show, I sit down with Ev Williams—someone whose work has profoundly shaped the modern internet. Ev co-founded Twitter, created Medium, and before all that, built Blogger, the original blogging platform (and the one where my own blog, Startup Lessons Learned, still lives today). We cover a wide range of topics, but a…

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The playbook for building a business to $1M/month with 3 employees, hiring great leaders, and rejecting Silicon Valley’s rules | Jess Mah (Rahway) 1:24:29

7M ago1:24:29

1:24:29

In this episode of The Eric Ries Show, I'm joined by Jess Mah, an extraordinary entrepreneur who launched her first six-figure business in middle school and went on to co-found more than 10 companies collectively valued at over $1 billion. Jess rose to public acclaim and earned a spot on Forbes' 30 Under 30 while privately facing the reality that h…

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ज्योतिषशास्त्र आणि विज्ञान यांच्यात खरंच काही संबंध आहे का? 1:27:33

7M ago1:27:33

1:27:33

ग्रहांमुळे तुमच्या आरोग्यावर, तुमच्या निर्णय प्रक्रियांवर, तुमच्या आयुष्यातील प्रत्येक बाबींवर कसा आणि काय परिणाम होतो, हे जाणून घेण्याची उत्सुकता तुम्हाला आहे का? डॉ. पं. संदीप अवचट ह्यांनी अमेरिकेतील २०२४ च्या निवडणुकीचे भाकीत निवडणूक सुरु होण्यापूर्वी सहा महिने आधीच केले होते, त्या भविष्याबद्दलचे भाष्य तुम्हाला ऐकायला आवडेल का? अमेरिकेतील निवडणू…

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The Hired CEO with Founder Mode | Marten Mickos (MySQL, HackerOne) 1:32:37

7M ago1:32:37

1:32:37

In this episode of The Eric Ries Show, I sit down with Marten Mickos, a serial tech CEO who has been at the forefront of some of the most transformative moments in open-source technology. From leading MySQL through its groundbreaking journey to guiding HackerOne as a pioneering bug bounty platform, Marten's career is a masterclass in building innov…

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How To Raise $125M Pre-Revenue and Why Harder Can Be Easier | Celine Halioua (Loyal) 1:40:25

8M ago1:40:25

1:40:25

In this episode of The Eric Ries Show, I'm joined by Celine Halioua, founder and CEO of Loyal, a groundbreaking biotech startup developing drugs to extend dogs' healthspan and lifespan. Celine's journey combines her passion for animals with a bold scientific mission that looks beyond pets to potentially transform human longevity as well. Our conver…

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Build Your Network of Mentors & Peers, Here’s How & Why! 54:58

8M ago54:58

54:58

Welcome to the Passionate Pulse Podcast's, Bootstrap Banter series! In this episode, we dive into the power of networking, peer support, and mentorship in shaping unconventional career paths. I’m Pranali, your host, sharing personal insights and real-world experiences on building a strong support system, whether you're an entrepreneur, solopreneur,…