Best Bootstrapped Giants Podcasts (2025)

1
He's controlling ChatGPT responses 50:56

23d 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…

1
MUST LISTEN: The 9 Biggest GTM Dysfunctions in B2B SaaS 53:09

5d ago53:09

53:09

This week on GTM Live, Carolyn and Trevor unpack the 9 go-to-market dysfunctions quietly derailing growth at even the most ambitious B2B companies. They dig into why so many teams, despite big budgets, headcount, and tools, are still struggling to drive efficient growth. Spoiler: it’s not the people. It’s the system. You’ll hear why fragmented data…

1
The Outsider Who Sparked New York’s Tech Ecosystem and Backed Multiple Billion Dollar Outcomes w/ Kevin O’Connor, Co-Founder of DoubleClick, fmr CEO of Graphiq, and Founder & GP at ScOp Venture Capital ... 44:43

7d ago44:43

44:43

In this episode of Outsider, Inc., host Ian Hathaway interviews Kevin O'Connor, co-founder of DoubleClick, former CEO of Graphiq, and Founder and General Partner at ScOp Venture Capital. Kevin shares insights from his remarkable career, starting from his early curiosity in electronics to forego a career as a research scientist and instead spearhead…

1
Episode 6: Culture Fit is BS 54:13

8d ago54:13

54:13

Is “culture fit” the secret sauce of team cohesion… or just startup speak for hiring people who look, think, and act exactly like you? In Episode 6 of UnicornPrn, Melissa and Lloyed torch the startup world’s favorite excuse for bias, groupthink, and hiring your drinking buddies. They unpack how “culture fit” became a Trojan horse for toxic execs, l…

1
The Ugly Truth About Pipeline (Real Talk for GTM Teams Running on Broken Systems) 43:11

13d ago43:11

43:11

This week on GTM Live, Carolyn sits down with Nick Flamini, host of the Sales Architecture Podcast, to explore the real reasons most go-to-market teams are still struggling—despite all the headcount, tools, and budget. They dig into the myth of “more BDRs = more pipeline,” and why most organizations are missing the data, architecture, and cross-fun…

1
Building a 400cr+ Waste Empire | Dhruv Luthra (Luthra Group) 1:08:56

15d ago1:08:56

1:08:56

"Waste is the resource which is in the wrong place." This powerful statement from Dhruv Luthra encapsulates the core philosophy driving the Luthra Group. It’s a paradigm shift from viewing waste as a problem to seeing it as an opportunity – a valuable raw material waiting to be transformed. This mindset has propelled the Luthra Group to the forefro…

1
Bootstrapping to Exit, First Principles Thinking, Product Simplicity, and Mentoring the Next Generation w/ Jason Seats, Co-Founder of Slicehost & fmr CIO of Techstars 59:03

21d ago59:03

59:03

On this episode of Outsider Inc., host Ian Hathaway sits down with Jason Seats, Co-Founder of Slicehost, former Chief Investment Officer of Techstars, and a pioneer in the startup and cloud computing worlds. Jason details his journey from co-founding the game-changing cloud infrastructure company, Slicehost, to mentoring and investing in early-stag…

1
The Hidden Systems Behind REAL Product-Led Growth (with Wes Bush) 47:27

23d ago47:27

47:27

Most SaaS teams claim they’re “doing PLG,” but very few are doing it well. This week on GTM Live, Carolyn and Trevor sit down with Wes Bush, CEO of ProductLed, to unpack why product-led growth often fails—and what to do about it. They explore why PLG isn’t just a pricing model or trial strategy, but a deep, systems-level shift that most teams under…

1
1440 is a Bootstrapped Giant 49:49

1M 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…

1
Exposing the Attribution Lie That’s Costing You Millions 58:41

1M ago58:41

58:41

Everyone’s analyzing win rates, but too few teams are asking the harder question: how did that opportunity even begin? This week on GTM Live, Trevor and Carolyn break down the most overlooked stage in go-to-market: what happens before a lead becomes a lead. They unpack why early-funnel signals (the ones that come before forms, meetings, or MQL scor…

1
Disrupting the Status Quo & Building Global Entrepreneurial Ecosystems w/ Linda Rottenberg, Co-Founder & CEO, Endeavor 57:06

1M ago57:06

57:06

On this episode of Outsider Inc., host Ian Hathaway interviews Linda Rottenberg, co-founder and CEO of Endeavor, the global organization supporting high-impact entrepreneurs in emerging markets. Linda shares her unique insights on the benefits of chaos over stability for entrepreneurship, her journey from an unlikely start in Latin America to creat…

1
Episode 5: These Hires Will Kill Your Company 43:18

1M ago43:18

43:18

In startup land, everyone acts like hiring’s a cheat code… “just add a rockstar!” But what if that rockstar needs a brief for everything, tanks morale, or burns $280K on vaporware? In Episode 5 of UnicornPrn, Melissa and Lloyed discuss the hiring disasters that don’t make it to TechCrunch, from corporate dinosaurs who can’t function without minions…

1
Inside the GTM Black Hole: Why Marketing Can't Prove Impact 46:19

1M ago46:19

46:19

Everyone’s trying to grow pipeline, but only few companies are measuring the part of GTM that actually creates it. This week on GTM Live, Trevor and Carolyn expose why the early-stage “signals” that actually drive pipeline are the ones most teams ignore. They dig into the real problem: teams aren’t tracking signals across the entire pipeline creati…

1
Solving Healthcare Affordability Crisis | Aditya Sharma (Affordplan) 51:05

1M ago51:05

51:05

"The journey of reduction in health care costs is not the responsibility of the hospital on its own, it's also the responsibility at the patient level." Aditya Sharma, CEO and Co- founder of AffordPlan, is tackling the critical issue of healthcare affordability in India. From his unique perspective as an investor-turned-founder, he's driving a purp…

1
From Central Missouri Hackathon to $5B Automation Platform w/ Wade Foster, Co-Founder & CEO, Zapier 50:40

2M ago50:40

50:40

In this episode of Outsider Inc., host Ian Hathaway sits down with Wade Foster, co-founder and CEO of Zapier, an automation platform valued at $5 billion. Wade discusses his unique path to success, starting from a typical middle-class environment in Missouri, leveraging lessons from early marketing roles, and winning a local hackathon with his init…

1
Why Your GTM Strategy Isn’t Working (Hint: Attribution, Data, and Unit Economics) 46:45

2M ago46:45

46:45

This week on GTM Live, Carolyn and Trevor dive into the messiness of go-to-market strategy: overspending on pipeline, bad attribution models, and why marketers are often stuck doing RevOps jobs. Carolyn breaks down the trap of chasing new logos without clear ROI, while Trevor shares how his IT-to-marketing journey led to launching Passetto to fix t…

1
Episode 4: Founder or Fraudster - Con Artists In The Boardroom 45:05

2M ago45:05

45:05

In the startup world, everyone preaches “fake it till you make it”. But what happens when faking it goes too far? Are you a bold founder hustling to realize a big vision, or a fraudster selling pipe dreams and ending up in handcuffs? In Episode 4 of UnicornPrn, Melissa and Lloyed pull back the curtain on the dark side of startup hustle – when “fake…

1
Zapier’s AI Revolution Hits NOW (Bootstrapped to $1M ARR w/ CEO Wade Foster) 59:00

2M ago59:00

59:00

In this episode I sit down with Wade Foster, the founder and CEO of Zapier. We explore Zapier’s unique path, from building its first integrations on nights and weekends in Missouri to scaling with minimal funding through Y Combinator. Wade shares how “don’t hire till it hurts” became a guiding mantra, why Zapier embraced remote work early on, and h…

1
RV240 - The End Of An Era (And Beginning Of A New One) - Go To Market Live Episode 45 24:18

2M ago24:18

24:18

After a month-long sabbatical that took him across Australia, New Zealand, and Fiji, Chris Walker returns to Revenue Vitals with a life-changing announcement. In this deeply personal episode, Chris reveals a profound shift in his perspective and purpose that has led him to hand over hosting duties to Carolyn Dilks (Co-Founder and Managing Partner @…

1
From Startup to IPO: Building a FinTech Giant in Charlotte w/ Michael Praeger, Co-Founder, Chairman & CEO, AvidXchange 45:51

2M ago45:51

45:51

In this episode of Outsider Inc., host Ian Hathaway interviews Michael Prager, co-founder and CEO of AvidXchange. Michael shares his entrepreneurial journey from founding early ventures to building AvidXchange into a leader in FinTech, processing $200 billion in annual payments. He discusses the importance of starting small, focusing on solving spe…

1
Surviving Downturns and Bootstrapping a Fintech Giant | Sameer Mathur (ROINet) 1:03:00

2M ago1:03:00

1:03:00

"You cannot grow the country's GDP if a third of your population is not a part of the financial inclusion piece." Sameer Mathur highlights the critical link between financial inclusion and national economic growth, emphasizing the vast untapped potential of serving the underserved in India. This isn't just about business; it's about societal impact…

1
Episode 3: Venture Capital is a Giant Ponzi Scheme 53:04

2M ago53:04

53:04

Is venture capital the fuel behind world-changing innovation…or just a glorified pyramid scheme where everyone’s pretending they’re building the next Uber while actually praying for a higher valuation before the money runs out? In this spicy episode of UnicornPrn, Melissa and Lloyed expose how the game is played — founders chasing funding like junk…

1
The $100B Revolution: How LLMs will Change Accounting Forever 30:32

2M ago30:32

30:32

In this episode, I sit down with Seema, a partner on the Andreessen Horowitz Fintech Team, to explore how AI is transforming accounting. We uncover why 75% of accountants may retire over the next decade and how AI could relieve shortages by streamlining data ingestion, research, reporting, and client advising. Seema also shares insights from her co…

1
Scaling Companies & Leveraging Community in Indianapolis w/ Scott Dorsey, Co-Founder & CEO, ExactTarget; Managing Partner, High Alpha 57:35

3M ago57:35

57:35

On this inaugural episode of Outsider Inc., host Ian Hathaway talks with Scott Dorsey, co-founder and former CEO of ExactTarget. Scott shares his journey from founding ExactTarget in 2000, through its $2.5 billion acquisition by Salesforce in 2013, to his current efforts in fostering entrepreneurship in Indianapolis via HighAlpha. Their discussion …

1
Episode 2: Cofounder Confessions — Love, Lies & Betrayal 56:36

3M ago56:36

56:36

Startups are messy. But cofounder relationships? Even messier. In this brutally honest episode of UnicornPrn, Melissa and Lloyed dive into the raw, real, and often ridiculous world of cofounder dynamics—from love stories gone wrong to business partnerships built on shaky foundations. They read founder DMs and dissect juicy, anonymized tales of star…

1
Episode 1: The Internet is for UnicornPrn 48:21

3M ago48:21

48:21

Welcome to the very first episode of UnicornPrn, the only podcast that peels back the glossy veneer of startup life and roasts it over a flaming pile of pitch decks. Hosted by Melissa Kwan and Lloyed Lobo, two founder friends who’ve seen the startup world from the inside out, upside down, and on fire… we’re here to talk about what it’s actually lik…

1
Welcome to UnicornPrn 1:02

3M ago1:02

1:02

UnicornPrn is the only podcast that peels back the glossy veneer of startup life and roasts it over a flaming pile of pitch decks 🔥 Hosted by Melissa Kwan and Lloyed Lobo, two founder friends who’ve seen the startup world from the inside out, upside down, and on fire. This show dives into what it’s actually like to build a company (spoiler: it’s no…

1
Inside Public's Product Strategy - Deep Dive w/ Leif Abraham 44:32

3M ago44:32

44:32

In this episode, I sit down with Leif, Co-founder and Co-CEO at Public, an investing platform built for people who take investing seriously. We discuss how Public raised $400 million, doubled its user base in just 48 hours, and evolved beyond commission-free trading to offer options, treasuries, bonds, and more. Leif shares their no-payment-for-ord…

1
I Built 4 AI Agents in 2 Weeks – No Code! 30:49

3M 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 …

1
Outsider Inc. Trailer 3:27

3M ago3:27

3:27

Introducing Outsider Inc., the podcast that dives into the untold stories of visionary leaders from unexpected places and backgrounds who broke the mold of tech entrepreneurship to build generation-defining companies. In each episode, host Ian Hathaway facilitates a conversation that reveals how founders turned early setbacks into stepping stones, …

1
State of Startups: Everything You Need to Know, with Peter Walker of Carta 1:06:23

3M ago1:06:23

1:06:23

In this episode I sit down with Peter Walker, head of insights at Carta, to discuss the sweeping changes in how founders are building and funding startups in 2024. Peter shares fresh data on AI’s outsized influence across every stage, why more founders are bootstrapping, and the real story behind down rounds and bridge rounds. We also dive into fou…

1
RV239 - The Bootstrap Advantage (My CEO Consulting Call) 8:25

3M ago8:25

8:25

In this unique episode, Chris shares the unfiltered audio from a consulting call with an entrepreneur. Chris offers advice from his personal experience building multiple businesses to 7 and 8 figures in revenue. Here’s what you’ll learn in this episode: Why raising VC money might be a sign that your business model needs rethinking The advantages of…

1
Ajay Singhania (Epack Durable) on building a Rs 3500Cr empire from near bankruptcy 1:05:19

3M ago1:05:19

1:05:19

From losing their biggest client to building a ₹3500 Cr manufacturing powerhouse, hear the inspiring journey of Ajay Singhania, MD & CEO of Epack Durable! In this episode of "The Spotlight", presented by the Founder Thesis podcast, learn how resilience, strategic pivots, and a commitment to "Make in India" fueled Epack's rise from near collapse to …

1
I found my zone of genius 45:54

3M 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…

1
RV238 - How To Outcompete $100M Giants (Live Fireside Chat) 52:24

3M ago52:24

52:24

Today’s episode is a live fireside chat recorded at Warmly’s office, where Chris covers why smaller software companies can move faster than larger ones, what customers actually want versus what they say they need, and practical ways to measure what matters in marketing. Here’s what you’ll learn in this episode: Why smaller companies have distinct a…

1
Amit Mehta's (Asha Ventures) Path to Impactful Investing 1:13:55

3M ago1:13:55

1:13:55

In this episode, Amit Mehta, Managing Partner at Asha Ventures, a venture capital and private equity firm highlights key lessons from his successful investments and the evolving Indian VC landscape. He discusses Asha Ventures' focus on sustainability, healthcare, and inclusion in its investment strategy, as well as the importance of governance and …

1
Fintech’s Biggest Shift Is Happening Now, with Sheel Mohnot of BTV 45:47

3M ago45:47

45:47

In this episode Rex chats with Sheel Mohnot from Better Tomorrow Ventures. Sheel shares his journey of living on a dollar a day in India, founding and selling multiple companies (including one sparked by a chance meeting on a train), and even hosting nine weddings—one of them sponsored by Taco Bell in the metaverse. They dive into Sheel’s evolving …

1
Sahil Anand (Cedar IBSi Capital) on the massive B2B Fintech opportunity 1:27:55

4M ago1:27:55

1:27:55

In this episode, join Sahil Anand, founder of Cedar IBSi Capital, as he shares his entrepreneurial journey, exploring the evolution of Cedar Consulting and the unique challenges of launching a fintech investment fund. Learn about the consulting landscape, Cedar's execution-heavy approach, and the promising future of fintech in India. Akshay Datt, a…

1
RV237 - Stop Overcomplicating Marketing Measurement | Go To Market Live Episode 44 51:37

4M ago51:37

51:37

When Chris Walker looked at his bank account in 2019, he had $3,000 and student loan debt. In this week’s GTM Live episode, he shares an overview of the choices that led to building successful multi-million dollar companies over the next 6 years, and the personal cost of those decisions. He then spends the majority of the episode examining why B2B …

1
Why You Unknowingly Resist Love, Joy, and Fulfillment 49:42

4M 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 …

1
RV236 - The Role of Finance Leaders in GTM Success 1:04:37

4M ago1:04:37

1:04:37

In this episode, Chris joinsFP&A Tomorrow host Paul Barnhurst (a.k.a.The FP&A Guy) to talk about the intersection of finance and GTM. Chris shares his perspective on why most B2B companies get GTM investments wrong, the inefficiencies in traditional marketing measurement, and how CFO's and finance teams can play an incredibly strategic role in driv…

1
Unravelling the Threads | Ankit Jaipuria @ ZYOD 1:18:51

4M ago1:18:51

1:18:51

Dive into the world of fashion manufacturing with Ankit Jaipuria, Co-founder of ZYOD! Discover how ZYOD is disrupting the B2B fashion industry with a cutting-edge supply chain, learn about the rise of fast fashion, and explore opportunities in India's growing market. Whether you're a fashion enthusiast, a business owner, or an aspiring entrepreneur…

1
RV235 - Create A High Performing GTM Engine | with Sangram Vajre 1:02:08

4M ago1:02:08

1:02:08

How can CEOs, CMOs, and revenue leaders truly create a high-performance GTM engine? This episode is a live event that Chris Walker did with Sangram Vajre (co-founder & CEO at GTM Partners) where they answer exactly that. Key topics from this episode: Who should really own GTM? Moving beyond “marketing vs. sales” The 4 pillars of pipeline creation W…

1
RV234 - The Pipeline Creation Framework | Go To Market Live Episode 43 45:32

4M ago45:32

45:32

Why do so many companies struggle to generate pipeline efficiently? In this episode, Chris shares exactly why (and new and more effective GTM strategies). Whether you're a CMO, CRO, CEO, or CFO, this episode will challenge your thinking and help you build a smarter GTM strategy with marketing investments that are actually delivering returns. Key to…

1
Redefining Wealth Management | Brijesh Damodaran @ Auxano Capital 46:11

4M ago46:11

46:11

Join us as we explore the inspiring journey of Brijesh Damodaran, Managing Partner of Auxano Capital, as he transitions from a corporate financial controller to a leading entrepreneur in wealth management. Discover his innovative "three-bucket strategy", insights into private market investing, approach to adapting to regulatory changes, and the imp…

1
RV233 - My Lessons From Scaling to $22 Million 48:41

4M ago48:41

48:41

Chris joined Brad Zomick’s show (LinkedIn Famous), where he shared insights on personal growth as a founder, his learnings from executing on LinkedIn for 5 years, and the new playbook founders can use to build and grow their companies. Key topics from this episode: The right way to approach LinkedIn (hint: vanity metrics don’t matter) Personal grow…

1
Nubank ft. David Vélez - An Outsider Upends the Brazilian Banking System 50:04

4M 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…

1
RV232 - The 3 Pillars of GTM Success | Go To Market Live Episode 42 50:52

4M ago50:52

50:52

This is the first GTM Live episode of 2025, and Chris shares his most recent GTM strategies to help you win. These lessons are especially crucial for companies who want to scale past $10 million ARR. Key topics from this episode: The 3 Pillars of GTM Success: GTM Strategy, GTM Optimization, and GTM Operations. Cost of Growth: Reframing GTM efficien…

1
Binu Jacob of Experion Technologies on The Art of Product Development 1:05:47

5M ago1:05:47

1:05:47

Join us for an enlightening episode featuring Binu Jacob, MD & CEO of Experion Technologies, as he recounts his extraordinary transition from aspiring professor to thriving entrepreneur in the product engineering services arena. Binu is the MD & CEO of Experion Technologies, a Global Product Engineering Services company offering enterprises future-…

1
RV231 - Chris Walker & Dave Gerhardt Talk B2B Marketing 48:28

5M ago48:28

48:28

This is a must-listen episode where Chris Walker joined Dave Gerhardt (Founder & CEO of Exit Five) on the B2B Marketing with Dave Gerhardt podcast. Key topics from this episode: Why being “early” in seeing how marketing is changing is often misunderstood as being wrong How to manage negativity on social media while staying focused on your goals Usi…

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Bootstrapped Giants Podcasts

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