Best Bootstrapped Giants Podcasts (2025)

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

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9d 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

13d 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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Why Unfelt Feelings Become a Prison for Founders 50:28

20d 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

1M 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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Creative Tension: The Secret to Creating Big Results Without the Grind 51:47

2M 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

2M 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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Is Spirituality the Missing Key for Founders? 46:37

2M 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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Close - Focused CRM does $50 million a year 49:11

3M 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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He's controlling ChatGPT responses 50:56

4M 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

5M 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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I Built 4 AI Agents in 2 Weeks – No Code! 30:49

6M ago30:49

30:49

[00:00:00] Introduction [00:00:45] Early Adoption of Generative AI & GitHub Copilot [00:01:30] Discovering How Code Comments Improve AI Suggestions [00:02:33] Skepticism About AI Hype & Fear of Being Left Behind [00:04:03] Seeing a YouTube Tutorial That Unlocked Building a RAG Agent [00:05:06] Building His First Agent in One Week (and Feeling “Bad …

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I found my zone of genius 45:54

7M ago45:54

45:54

[00:00:00] Intro & Evolving Work Relationship [00:01:03] Balancing Andrew’s Creative Side vs. Business Demands [00:02:06] Integrating Different Approaches from Teammates [00:02:33] Identifying and Staying in Your “Zone of Genius” [00:04:03] Tasks That Energize vs. Tasks That Drain [00:05:06] Struggle With First Drafts & Delegation [00:06:09] Commit…

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Why You Unknowingly Resist Love, Joy, and Fulfillment 49:42

7M ago49:42

49:42

Most people think they struggle with fear or failure. But the truth is, we’re often more afraid of love, joy, and being fully seen. In this episode, Dave Kashen, Jesse Pujji, and Andrew Warner uncover the hidden ways we resist appreciation, connection, and fulfillment—without even realizing it. They break down why receiving acknowledgment can feel …

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Nubank ft. David Vélez - An Outsider Upends the Brazilian Banking System 50:04

8M ago50:04

50:04

When Nubank started 10 years ago, a few big banks in Brazil had a stranglehold on the largest economy in Latin America: they controlled nearly all the market share, and imposed some of the highest fees and worst banking terms in the world. David Vélez was an unlikely character to challenge the system: an outsider from Colombia and Costa Rica with a…

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Dropbox ft. Drew Houston - How the Cloud Pioneer Reinvented Itself 50:44

8M ago50:44

50:44

A scrappy upstart taking on hyperscalers in a category with lots of hand-wavers, Dropbox became the canonical example of Silicon Valley viral growth, adding 50 million users in the first years following their 2008 launch and quickly dominating their category. However, as CEO Drew Houston explains, their path from viral sensation to enduring busines…

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The Secret to Creating Your Dream Life and Business in 2025 51:06

8M ago51:06

51:06

What if the key to creating your dream life and business isn’t about working harder—but about taking radical responsibility for your entire experience, including the belief that it has to be difficult? In this episode, Jesse Pujji, Dave Kashen, and Andrew Warner reveal how entrepreneurs unknowingly create their own overwhelm by holding onto limitin…

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LIVE: ServiceNow CEO Bill McDermott on Unlocking Elite Level Execution 32:20

9M ago32:20

32:20

Earlier this season we heard the startup story of ServiceNow—from Fred Luddy setting out to reinvent IT workflows as a first-time founder, to Frank Slootman joining as CEO to scale the business to an IPO. Even more remarkable is that ServiceNow has only accelerated as a public company, growing over ten-fold in the last decade. At a recent closed ev…

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How Emotions Are Your Decision-Making Compass 56:29

9M ago56:29

56:29

What if the emotions you’ve been avoiding are the key to making better decisions and unlocking your true potential? In this episode, Jesse Pujji, Dave Kashen, and Andrew Warner dive into how emotions like fear, anger, and sadness can guide you to clarity and alignment—if you let them. They explore why resisting emotions creates stress and confusion…

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Robinhood ft. Vlad Tenev - Reinventing Finance for a New Generation 48:27

9M ago48:27

48:27

Millions of Americans use their smartphones to invest and manage their finances every day—but before Robinhood started in 2013, finance looked very different. Investing was something for the wealthy, with steep fees charged on every trade, and was done exclusively on computers with arcane trading software. In this episode, co-founder and CEO Vlad T…

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Outperform Yourself By Breaking Your Upper Limit 49:20

9M ago49:20

49:20

No matter how big your goals are or how much you’ve already achieved, you might have an 'upper limit problem' quietly holding you back. In this episode of The Heart of Entrepreneurship, Jesse Pujji, Dave Kashen, and Andrew Warner dive into the hidden barriers that limit success—even for high achievers. Together, they explore how unconscious beliefs…

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YouTube ft. Steve Chen - 18 Months That Changed the Internet 48:44

9M ago48:44

48:44

This episode takes us back to the earliest days of YouTube, as the founders explain why it was a longshot that succeeded against all odds. When cofounders Steve Chen, Chad Hurley and Jawed Karim left PayPal to start YouTube, it wasn’t even clear that the nascent broadband infrastructure could support playing video in a browser. In a brief period un…

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The Limiting Stories Entrepreneurs Tell Themselves—And How to Let Them Go 47:51

10M ago47:51

47:51

Entrepreneurs often chase success by pushing harder and striving for more, but what if the real key lies in rethinking the stories we tell ourselves? In this episode, Jesse Pujji and Dave Kashen share practical exercises to help entrepreneurs separate facts from narratives, freeing them from the things that hold them back––like guilt, regret, and b…

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Natera ft. Matthew Rabinowitz - A Personal Mission That Led to a Biotech Revolution 53:25

10M ago53:25

53:25

Founder Matthew Rabinowitz opens up about the intensely personal journey that set him on a course to revolutionizing healthcare. A PhD in electrical engineering, he had no background in genetics or biology, but after his sister had a baby with Down syndrome that hadn’t been detected and tragically died after 6 days, Matthew dedicated himself to sol…

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LIVE: DoorDash’s Tony Xu and Miki Kuusi Talk Scaling Operational Excellence 29:48

10M ago29:48

29:48

Tony Xu and Miki Kuusi share insights from building two of the world's most successful delivery platforms—DoorDash and Wolt—which merged in 2022 to create an $80B GOV business operating in 32 countries. In this candid conversation with Sequoia's Alfred Lin live at a Sequoia event in Europe, they discuss the challenges of scaling operational excelle…

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Why We're Doing This Podcast 48:44

10M ago48:44

48:44

Jesse Pujji sold a big piece of his company, Ampush. He should have felt "safe" and happy and more productive. It didn't work. He hired Dave Kashen to coach him. That was a huge unlock. It led him to build multiple companies, have a happier family life and embrace his love of teaching. This podcast shows why that happened. And why they're launching…

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DoorDash ft. Tony Xu - The “Wrong” Moves That Built a Giant 53:09

11M ago53:09

53:09

DoorDash faced skeptics from the start. Grubhub, Delivery.com, and others were already addressing the restaurant delivery market when CEO Tony Xu and his co-founders started in 2013. But after talking to hundreds of local small businesses, they realized there was still an unmet need: None of the competitors solved the problem of delivery with an on…

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UiPath ft. Daniel Dines - From Bootstrapping in Bucharest to One of Software’s Biggest IPOs 42:05

11M ago42:05

42:05

The biggest enterprise software company to come out of Europe in the last decade didn’t come from London, Paris, Berlin or Stockholm—but Bucharest, Romania. UiPath, founded in 2005 and originally called DeskOver, was a scrappy handful of engineers bootstrapping out of an apartment in Bucharest for about a decade, seeking in vain for product-market …

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Reddit ft. Steve Huffman - The Making (and Remaking) of the Front Page of the Internet 43:24

12M ago43:24

43:24

Reddit is one of the largest and most culturally influential sites on the internet—and its journey is one of the most unusual company stories in internet history. College roommates Steve Huffman and Alexis Ohanian founded Reddit in 2005 and scaled it on a shoestring until Condé Nast acquired it the following year. Struggling for direction under its…

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Raising $500M to build a meaningful business with Job van der Voort (Remote) 47:49

12M ago47:49

47:49

In this episode of The Only Thing That Matters, I sit down with Job van der Voort, CEO and co-founder of Remote—a company that has raised over $500 million, operates in 67 countries, and is valued at $3 billion. 🌍 Job shares the incredible journey of building Remote from a simple job board to a global platform solving one of the most complex challe…

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MongoDB ft. Dev Ittycheria - How an Early Pivot Catalyzed an Open Source Movement 44:24

1y ago44:24

44:24

MongoDB, founded in 2007, originally aimed to create a platform-as-a-service system with a new database layer. Facing competition from Google, the founders pivoted to focus solely on their database product, MongoDB—a new kind of database built for the scale of the internet era. Founder Dwight Merriman built a product that developers loved, but scal…

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Scaling to $50M in revenue over 18 years with Timo Buetefisch (Cooltra) 52:47

1y ago52:47

52:47

Timo Buetefisch is an entrepreneur like no other. He's the founder of Cooltra and he is still running the company after 18 years. Not only that, he's grown Cooltra "slow and steady" to over $50M in annual revenue over that period of time. Learn how Cooltra grew from a humble bootstrap startup to a booming enterprise with 28,000 electric vehicles an…

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ServiceNow ft. Frank Slootman and Fred Luddy - From Starting Over at 50 to Dodging a $150B Mistake 42:42

1y ago42:42

42:42

In 2004, bankrupt after the company where he’d previously worked had imploded, Fred Luddy decided to start over as a first-time founder at age 50. His vision was to reinvent the nascent IT software field for the cloud era. What started as simple help desk replacement software would eventually become a ~$150B market cap company powering digital work…

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The art of pivoting with Rajiv Ayyangar (Tandem + Product Hunt) 1:02:38

1y ago1:02:38

1:02:38

What happens when you can't find product-market fit with your startup idea? It's time to pivot, and Rajiv Ayyangar, CEO of Product Hunt and co-founder of Tandem, is a master at that. In this episode, Rajiv shares his journey from the highs of rapid growth to the tough calls of pivoting and transitioning Tandem to a self-sustainable business. Gain a…

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Crucible Moments Season 2: Coming August 29 2:30

1y ago2:30

2:30

In Season 1 of Crucible Moments, we heard from founders like PayPal’s Max Levchin, Block’s Jack Dorsey, Nvidia’s Jensen Huang and more about the turning points and key decisions that shaped their journeys. Now Crucible Moments is back for another exciting season. We’ll get the unvarnished history and inside story from Tony Xu of DoorDash, Drew Hous…

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Turning a naive idea into a 7-digit exit with Javier Escribano (Tourist Eye) 1:18:57

1y ago1:18:57

1:18:57

How do you build a successful travel app from scratch, grow it to millions of users, and sell it to a big brand in the industry? Join us as my former co-founder, Javier Escribano, and I recount our journey from naive 22-year-olds to existing to Lonely Planet. You'll learn the four critical checks for achieving product-market fit, and why validating…

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We launched a $40k/month newsletter 53:52

1y ago53:52

53:52

In this episode: how we launched our newsletter, Bootstrapped Giants. Presented by: Superhuman, the email app that gets us to inbox zero fast, helps us sell more and enables us to collaborate. Time stamps: [00:01:03] Why start the Bootstrapped Giants podcast? [00:01:26] Can you introduce yourself briefly? [00:04:03] Should we use clickbait titles? …

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E00: Why can't Andrew start this podcast? 43:18

1y ago43:18

43:18

We recorded 4 episodes and Andrew hasn't posted 1. Why not?By Andrew Warner and Jesse Pujji

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From side project to software giant with Alexis Fogel (Stonly + Dashlane) 1:15:44

1y ago1:15:44

1:15:44

Discover the journey from fun coding project to pioneering password management tool with Alexis Fogel, co-founder of Dashlane and CEO of Stonely. Alexis kicks things off by sharing how a school project aimed at universal one-click purchases evolved into a leading password manager and digital wallet, thanks to invaluable user feedback and a few key …

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Seeking freedom after a $130M exit with Pau Sabria (Olapic + Remotely) 1:05:07

1y ago1:05:07

1:05:07

What happens after you sell your startup for $130M? Join us as we sit down with Pau Sabriá, the mastermind behind Olapic and Remotely, to unravel the secrets of sustainable business growth and personal freedom. Discover how Pau transitioned from raising over $22 million in venture capital and selling Olapic for $130M to a more balanced and fulfilli…

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Introducing "Training Data," a new podcast from Sequoia about the future of A.I. 51:19

1y ago51:19

51:19

Crucible Moments will be back shortly with season 2. You’ll hear from the founders of YouTube, DoorDash, Reddit, and more. In the meantime, we’d love to introduce you to a new original podcast, Training Data, where Sequoia partners learn from builders, researchers and founders who are defining the technology wave of the future: AI. The following co…

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Bootstrapping to $20M with Amir Salihefendic (Todoist) 1:04:49

1y ago1:04:49

1:04:49

What if you could build a leading brand in a highly competitive market and grow to $20M in annual revenue without raising venture capital? In this episode, I chat with Amir Salihefendic, the brain behind Doist and its popular task management app, Todoist. Amir reveals his journey of bootstrapping Doist from a side project to a full-blown business. …

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Raising $80M to reforest the world with Diego Saez-Gil (Pachama) 1:05:06

1y ago1:05:06

1:05:06

Join us as we uncover the multifaceted entrepreneurial journey of Diego Saez-Gil, who navigated the twists and turns of three different startups. From the highs of selling a successful budget accommodations app to the lows of confronting airline restrictions with smart luggage, Diego's story is a testament to resilience and innovation. In this epis…

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Monetizing Open Source with Peer Richelsen (Cal.com) 1:26:39

1+ y ago1:26:39

1:26:39

Discover the secrets behind monetizing open-source projects with Peer Richelsen, co-founder and CEO of Cal.com. In this episode, Peer shares his journey from a frustrated calendar user to a pioneering entrepreneur raising over $30M to create Cal.com, an open-source scheduling platform. We explore the challenges and strategies involved in building a…

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Building Capital-Efficient Startups with François Derbaix (Indexa Capital) 1:03:38

1+ y ago1:03:38

1:03:38

Unlock the strategies of capital-efficient entrepreneurship with François Derbaix, the mastermind behind Indexa Capital, and delve into the art of scaling a startup without burning vast amounts of capital. This episode is a treasure trove of insights as François shares his journey of achieving profitability and outpacing competitors by a significan…

1
Welcome to The Only Thing That Matters 1:36

1+ y ago1:36

1:36

This is "The Only Thing That Matters", the podcast where Ariel Camus, serial entrepreneur, interviews successful founders to deconstruct their path to product-market fit and extract the principles and frameworks behind their success. You’ll hear about the insights from raising hundreds of millions of dollars and exiting multi-million dollar busines…

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Nvidia ft. Jensen Huang - An overnight success story 30 years in the making 39:23

2y ago39:23

39:23

CEO Jensen Huang tells the legendary story of Nvidia, from the company’s early days pioneering 3D graphics cards for a niche PC gaming market to powering the AI revolution as the sixth most valuable company in the world. Nvidia faced multiple near-death experiences along the way, and their so-called “diving catches,” as Jensen calls them, were some…

1
23andMe ft. Anne Wojcicki - How a DNA startup took on the FDA and redefined health tech 38:45

2y ago38:45

38:45

Millions of customers have explored their genome with 23andMe. But when the company started in 2006, the idea of consumer DNA testing was heresy to the medical establishment. The FDA once even ordered 23andMe to stop selling its health testing product. The company persevered to make allies out of adversaries, and became the only FDA-approved produc…

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Jawbone ft. Hosain Rahman - The rise and fall of the first wearable technology company 36:56

2y ago36:56

36:56

Co-founders Hosain Rahman and Alex Asseily, and Chief Creative Officer Yves Behar, recount the meteoric rise and fall of Jawbone. One of the most innovative companies of the mid 2000s, Jawbone pioneered wearable technology with UP, the first wrist-worn fitness tracker, and revolutionized sound with Jambox, the first smart wireless speaker. In one o…

1
HubSpot ft. Brian Halligan & Dharmesh Shah - How an underdog helped invent modern marketing, and then took on Goliath 33:08

2y ago33:08

33:08

Founders Brian Halligan and Dharmesh Shah reveal how they took a blog started as a hobby and turned the ideas behind it into a $20+ billion success. In 2006, HubSpot upended traditional approaches to marketing by taking advantage of the the nascent internet in a new way: By capitalizing on seach engines and social media, they offered a way to pull …

1
Eventbrite ft. Julia Hartz - A thriving events company took 14 years to build and nearly disappeared in 14 days 45:19

2y ago45:19

45:19

What happens to an events company when every event is canceled? “Even if you have spent 14 years building something, it could truly be gone in 14 days.” After working tirelessly to revolutionize how live events are organized, this was the reality Eventbrite CEO Julia Hartz faced in March of 2020 as pandemic lockdowns went into effect, extinguishing…