Best Bootstrapped Giants Podcasts (2025)

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AI is eating the world 26:42

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9h ago26:42

26:42

🎧 Highlights: [00:00:00] Benedict Evans and “AI Eats the World” [00:01:30] Will startups unbundle ChatGPT? [00:05:00] Why vertical specialization wins [00:07:03] Every startup is now “AI-first” [00:07:48] The trillion-dollar AI consulting wave [00:10:57] Is AI a new plateau or the next exponential curve? [00:12:00] The pyramid of progress: computin…

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AI made a “no code” guy into a coder 54:10

7h ago54:10

54:10

🎧 Highlights: [00:00:00] From Makerpad to Factory — Ben Tossell’s journey [00:01:33] Life after acquisition and redefining work [00:05:06] Why AI might make things harder, not easier [00:07:30] No-code lessons and the illusion of simplicity [00:10:42] From teaching no-code to debugging workflows [00:12:00] Learning to code with AI as your translato…

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Inside a Designer’s Mind: The MarTech Operator’s Playbook 36:42

5d ago36:42

36:42

In this episode of HIGT, hosts Adam and Amanda sit down with Lindiwe Stenberg, newly promoted Chief of Staff to the VP of Marketing at Venmo (formerly Growth Marketing Operations Lead), to explore her unconventional career journey from multimedia design to nursing school to fintech marketing, her philosophy on continuous learning, and practical str…

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The Psychology of Motivation No One Taught You 54:56

10d ago54:56

54:56

Do you secretly believe success has to come with suffering? In this episode, Jesse Pujji and Dave Kashen challenge one of the most deeply ingrained beliefs in entrepreneurship — that ambition, achievement, and peace can’t coexist. They explore what it means to shift from dirty fuel (fear, lack, and self-criticism) to clean fuel (love, creativity, a…

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Solopreneurs: Doing Everything. Growing Nothing? Get these Fixes to Finally generate revenue! 55:14

10d ago55:14

55:14

Welcome to Bootstrap Banter, the show where we strip away the noise and talk about the raw truth behind building something real from scratch without waiting for permission. In this episode, we tackle the unspoken reality of why most hustlers don't become companies. Discover the three biggest roadblocks that side hustlers face. Learn how to transfor…

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How I became a board member of a major supermarket 32:59

18d ago32:59

32:59

⏱ Episode Breakdown 00:00 – Andrew questions the real value of being on a board 02:00 – Jesse’s framework: people, impact, learning, and comp 04:00 – The unique story of Schnucks: family values and $4B scale 06:00 – What makes a board seat “worth it” for Jesse 08:00 – How he ended up on the Schnucks board 09:00 – The role of impact in Jesse’s decis…

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Inside a VC Mind - What Separates Fundable Startups From the Rest? 1:03:06

18d ago1:03:06

1:03:06

Join us on the Passionate Pulse Podcast's Capital Pulse series as we welcome Gautam Gupta, former partner at TCV funds and founder of NatureBox. Gautam shares his incredible journey from raising a $2 million seed round to scaling NatureBox to $70 million. Discover the key lessons he's learned about taking bold steps, leveraging existing networks, n…

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The Ultimate Guide for Creating Products People Trust | Seth Goldman (Honest Tea) 1:03:38

18d ago1:03:38

1:03:38

Most companies scale by cutting corners. Seth Goldman built a brand by refusing to. Seth is one of the founders of Honest Tea, a longtime chair at Beyond Meat, and the cofounder of Just Ice Tea. His career has been defined by a belief that business can be a force for human and environmental good. From a thermos of tea brewed in his kitchen to natio…

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Pepper’s content making machine 37:24

21d ago37:24

37:24

🎧 Highlights: [00:00:00] From freelance writer to $10M ARR founder [00:03:36] How Pepper scaled from a marketplace to an AI-powered content engine [00:05:06] The hybrid model: humans and AI creating together [00:07:12] Building “Nimbus” — Pepper’s internal AI platform [00:08:24] Re-optimizing thousands of old pages automatically [00:13:03] Why FAQs…

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Lonely at the Top: Why Success Can Still Feel Empty 53:59

24d ago53:59

53:59

Lonely at the Top: How Success Can Disconnect Founders From Themselves What if chasing success actually makes you feel less fulfilled? In this episode, Jesse and Dave unpack Brian Chesky’s viral reflection on the loneliness he felt after Airbnb's $100B IPO. Despite achieving the dream, he felt disconnected, empty, and unsure of how he got there. Th…

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Why Saying “No” Is Key to Long-Term Success 31:03

25d ago31:03

31:03

Building a Sustainable Agency Through Values-Driven Leadership and Specialist Focus.In this episode of How I Grew This, hosts Amanda and Adam speak with Mick Rigby, founder and CEO of Yodel Mobile, about his 20-year journey building a specialist mobile app marketing agency. From launching just before the iPhone's debut to being recently acquired by…

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Why I'm Building an AI Writer 40:35

26d ago40:35

40:35

🎧 Highlights: [00:00:00] Why build your own AI writer instead of using existing tools [00:02:15] The dream of never writing social posts again [00:03:36] “Software is no longer generic — it’s bespoke” [00:06:18] Excel as the original custom-software platform [00:08:42] How Excel models run billion-dollar deals [00:10:39] The rise of low-code and AI…

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What AI Tools Founders Actually Use 7:19

26d ago7:19

7:19

Andrew shares the AI tools that real startup founders are using every day — not hype, but the ones that actually help them work smarter. From AI note-takers that surface your blind spots to automations that coach your team after meetings, these are the tools that top entrepreneurs rely on. 🔗 Tools mentioned: Granola App: https://www.granola.ai/ Cla…

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How to do AEO - Answer Engine Optimization 51:34

28d ago51:34

51:34

🎧 Highlights: [00:00:00] Intro – “Don’t start with SEO. Start with AEO.” [00:00:36] Why this is the right time to focus on answer engine optimization [00:01:30] Case study: Webflow drives 8% of signups from LLMs [00:03:00] Onsite vs. offsite optimization — Reddit and YouTube matter most [00:06:18] Why Help Center content outperforms traditional SEO…

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From Deepti’s Double to Oprah’s Ownership - When Women Play to Change the Game! 54:59

1M ago54:59

54:59

Learn how to turn every “no” into your next big play. This Bootstrap Banter episode celebrates women who didn’t just play the game — they changed it. From cricket fields to boardrooms, uncover the secret pillars behind women’s wins and take actionable strategies to elevate your game in your career field. Attention, ambitious women! If you're ready …

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How the Former U.S. CTO Built a $3B Healthcare Company Powered by Love | Todd Park 1:32:24

30d ago1:32:24

1:32:24

Most companies optimize for profit. Devoted Health was built to serve people. In this episode of The Eric Ries Show, I sit down with Todd Park, co-founder of Devoted Health and former U.S. Chief Technology Officer, to explore what it looks like to design a company for human flourishing at scale. Todd shares how Devoted earned one of the highest tru…

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Why is Morning Brew’s founder selling “AI Transformation”? 1:01:42

1M ago1:01:42

1:01:42

🎧 Highlights: [00:00:00] Intro [00:02:06] Alex & Arman’s founding story — from pivot to partnership [00:03:09] Why engineers experience AI’s biggest leverage [00:05:15] “Think of it as a high-quality AI-powered dev shop” [00:06:36] The big vision: Building the McKinsey of AI [00:09:09] Crossing the chasm: From pre-AI to post-AI [00:13:03] Intellige…

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What Happens When You Move Beyond the Ego 58:18

1M 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

1M 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

1M 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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Building Mission-Driven Products in Regulated Industries: Lessons from 20 Years in Product Management 33:18

1M 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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Neil Patel’s AI System for Getting 100 Clients a Week 46:56

2M 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

2M 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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Why Following Aliveness Might Be the Smartest Business Move 44:26

2M 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

2M 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

2M 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

2M 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

2M 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

2M 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

2M 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

2M 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

2M 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

2M 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

3M 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

3M 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

3M 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

3M 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

3M 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

3M 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

3M 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

3M 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

3M 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

4M 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

4M 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

4M 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

4M 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

5M 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

5M 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

5M 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

5M 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…