Best Venture Capital Vs Bootstrapping Podcasts (2025)

1
SaaStr 818: Anthropic, Cursor, Fal & Bessemer: The Realities of Scaling AI 30:57

Play Pause

4h ago30:57

30:57

SaaStr 818: Anthropic, Cursor, Fal & Bessemer: The Realities of Scaling AI Join Talia Goldberg (Bessemer Venture Partners), Kelly Loftus (Anthropic), Jacob Jackson (Cursor), and Gorkem Yurtseven (FaL - Feautres and Labels) as they discuss the evolving landscape of AI, business models, metrics, and the future of generative media. 00:00 - Introductio…

1
Portfolio Construction, Power Laws and Fund Differentiation in Venture Capital - E623 9:58

12h ago9:58

9:58

Jeremy Au broke down how venture capital funds design LP decks, allocate capital, and differentiate themselves in competitive markets. The discussion covered portfolio construction math, capital call strategy, the role of opportunity funds, and how funds highlight unique value-adds like founder wellness programs. 02:12 Capital Calls and Timing Fund…

1
Jianggan Li: China Price War Chaos, EV Subsidy Battles & Why Firms Flee Abroad – E622 30:37

3d ago30:37

30:37

Jeremy Au and Jianggan explore why China business environment is locked in cycles of over-competition that destroy margins and push firms to seek growth abroad. They trace how JD, Meituan, and Alibaba’s food delivery war escalated into billions of yuan in subsidies, why regulators hesitate to intervene, and how clusters like Shenzhen and Hangzhou s…

1
Gita Sjahrir: Indonesia Corruption Protests, eFishery Police Detention & Public Mistrust vs. Startup Governance – E621 36:50

5d ago36:50

36:50

Jeremy Au and Gita Sjahrir unpack Indonesia’s turbulence, from corruption scandals and startup economic uncertainty due to the collapse of eFishery. They contrast Singapore’s stability with Indonesia’s volatility, explore how weak rule of law erodes trust, and discuss how scandals damage both founders and investors. They also analyze the role of bo…

1
DJ Tan: $4.2M Fundraise Flavor House, Bean-Free Coffee Product-Market Fit & Climate Change vs. Food Tech – E620 40:11

8d ago40:11

40:11

Jeremy Au and DJ Tan sit down to discuss how Prefer grew from a bold bean-free coffee experiment into a flavor house tackling climate-threatened ingredients. They explore the evolution from naive product launches to customer-driven adoption, why B2B positioning makes more sense than B2C in food tech, and how shifting investor expectations shaped th…

1
SaaStr 817: What Happens When AI Kills Your SaaS Growth? Live Q&A with SaaStr CEO and Founder Jason Lemkin 48:04

9d ago48:04

48:04

SaaStr 817: What Happens When AI Kills Your SaaS Growth? Live Q&A with SaaStr CEO and Founder Jason Lemkin In this Q&A session from SaaStr Annual, Jason Lemkin delivers hard truths about how AI is reshaping the entire SaaS landscape. No sugarcoating, no feel-good platitudes - just the brutal reality of what's happening to B2B companies right now. W…

1
Kristie Neo: Southeast Asia’s Mood Shift, Middle East Optimism & Gen Z’s AI Job Crunch – E619 49:20

10d ago49:20

49:20

Kristie Neo and Jeremy Au compare Southeast Asia and the Middle East, exploring how mood shifts, tariffs, scandals, and cultural codes are shaping technology and finance. They discuss Southeast Asia’s dampened atmosphere after 2021, the role of sovereign wealth in the Middle East, and how generational challenges meet an AI-driven job market. Their …

1
Rob Liu: Bootstrapping to Millions, Why Venture Capital Is Credit Card Debt, and Learning Science for Impact – E618 40:32

12d ago40:32

40:32

Rob Liu, Founder of ContactOut, and Jeremy Au dive into the realities of building a profitable SaaS business, the myths of venture capital, and the role of lifelong learning. Rob shares how he scaled ContactOut by stacking insights from competitors, why bootstrapping gave him more control, and how he now invests in young founders. Their conversatio…

1
Choosing Personal Success Before Professional Glory - E617 11:22

15d ago11:22

11:22

Jeremy Au spoke about the dangers of chasing only professional success and why it can lead to emptiness despite external achievements. He explained the importance of balancing career ambition with personal happiness, introduced a shifting framework for finding purpose, and shared stories that highlight resilience, injustice, and the values that tru…

1
Would you take that check? 33:48

16d ago33:48

33:48

Would you take that check again? Two founders. Two paths. One backed by venture capital, the other bootstrapped. This episode breaks down the tradeoffs of startup funding in today’s environment, where open-source tools and cheaper tech stacks have changed the rules. What you’ll hear: How modern stacks cut startup costs VC mentorship vs. hard-earned…

1
SaaStr 816: PLG to Enterprise to SMB: Insights from Calendly's CEO 31:48

16d ago31:48

31:48

Join us as Jason Lemkin, CEO, and Founder of SaaStr, sits down with Tope Awotona, CEO, and founder of Calendly for an insightful AMA session. They discuss Calendly's journey, their success in the Product-Led Growth (PLG) domain, and how it balances self-serve with enterprise sales strategies. Tope shares candid lessons learned from growing Calendly…

1
Javier Lorenzana: Startup Failure to Social Media Star and Building Influence that Lasts – E616 32:06

17d ago32:06

32:06

Javier Lorenzana, former EdTech founder turned content creator, joins Jeremy Au to revisit their first meeting during an On Deck podcasting course and trace his journey from startup building to social media success. They discuss the creation and shutdown of his pandemic-born company Upnext, the personal and professional fallout that followed, and h…

1
Sang Shin: Startup Rebel, Investor Philosopher and Life in a Simulation – E615 56:46

19d ago56:46

56:46

Jeremy Au and Sang Shin trace Sang’s journey from a privileged childhood in the Philippines to his evolution as an entrepreneur, investor, and philosopher. They unpack the pivotal moments that shaped his outlook, the hard lessons from building a privacy-first startup that challenged big tech, and his creation of Fafty, a belief system grounded in t…

1
Health, Purpose & Criticism Choosing Your Pain, Building Resilience and Leading for the Long Haul - E614 12:45

22d ago12:45

12:45

Jeremy Au shares why long-term career success depends on investing in health, cultivating purpose, and learning to handle inevitable criticism. He explains the link between purpose and happiness, why choosing your challenges makes them more bearable, and how treating yourself as your own best friend helps you grow despite setbacks. 02:00 The Role o…

1
SaaStr 815: Redpoint Ventures Playbook: How Top VCs Are Really Investing in AI 31:52

23d ago31:52

31:52

SaaStr 815: Redpoint Ventures Playbook: How Top VCs Are Really Investing in AI with Jacob Effron, Managing Director of Redpoint Ventures Jacob Effron, Managing Director at RedPoint, discusses the state of AI investing and the rapid advancements in AI technology. He highlights the significant decrease in model costs, increased AI capabilities in app…

1
Adrian Choo: Career Skeletons, AI Assistants & Why Singapore is Losing Jobs to KL and Bangkok – E613 53:01

24d ago53:01

53:01

Adrian Choo, CEO of Career Agility International, joins Jeremy Au to explore how AI, job insecurity, and shifting regional trends are reshaping the future of work in Southeast Asia. They discuss why Singapore is losing its dominance as a regional employment hub, how mid-career professionals are getting priced out, and why Gen Z graduates are enteri…

1
Jianggan Li: China Rare Earth Power, Vietnam USA Fast Deal & Labubu's Global Rise – E612 35:19

26d ago35:19

35:19

Jianggan Li, Founder of Momentum Works, joins Jeremy Au to unpack the evolving trade dynamics between China, Vietnam, and the United States. They compare Vietnam’s swift concessions with China’s calculated rare earth strategy, discuss the blurred lines of transshipment, and explore how Apple, Pop Mart, and Labubu reflect larger trends in global man…

1
Fairness Isn’t Real, Power Awareness & Small Fish Career Strategy – E611 12:27

29d ago12:27

12:27

Jeremy Au speaks about the uncomfortable truth that the world isn’t fair. He urges listeners to let go of idealism, understand real-world power dynamics, and make deliberate career choices. From decoding hypocrisy in leadership to choosing when to be a small fish in a big pond, he shares how to survive and thrive by thinking both outside-in and ins…

1
SaaStr 814: How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott 41:54

1M ago41:54

41:54

SaaStr 814: How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott Join Maggie Hott, GTM Leader at OpenAI, as she shares her extensive experience in building top-performing sales organizations at SaaStr. With a remarkable career history at Eventbrite, Slack, Webflow, and OpenAI, Maggie distills 15 years of insights into a tacti…

1
Tiang Lim Foo: Start-Up Governance, VC Math Reality & How AI Is Rewiring SEA Startups – E610 45:53

1M ago45:53

45:53

Tiang Lim Foo, General Partner at Forge Ventures, and Jeremy Au discussed how Southeast Asia’s tech and venture capital landscape is evolving through cycles of hype, correction, and AI-driven transformation. They unpack the eFishery scandal as a clearing event, reframe expectations around exits, and debate whether venture capital remains viable in …

1
Sudhir Vadaketh: Building Jom, Managing Fear & Publishing Bravely in Singapore – E609 47:45

1M ago47:45

47:45

Sudhir Vadaketh, Co-founder and Editor-in-Chief of Jom, returns to BRAVE after four years to share how he built a long-form journalism outlet in Singapore. He and Jeremy Au discuss the journey from solo writer to team manager, the real risks and support systems behind independent media, and how Jom navigates Singapore’s evolving boundaries on speec…

1
Shiyan Koh: Singapore Studies Nuclear Energy, SEA Startup Pessimism & AI Waifus – E608 44:38

1M ago44:38

44:38

Shiyan Koh, Managing Partner at Hustle Fund, joins Jeremy Au to explore Singapore’s exploration of nuclear energy, the Southeast Asia startup downturn, and how AI is changing both business and social behavior. They discuss how the government seeds long-term energy strategy, what optimism looks like in a bear market, and why human interaction must r…

1
SaaStr 813: From Startup to $11B: ServiceTitan's CRO Breaks Down Their Sales Playbook 32:39

1M ago32:39

32:39

In this session, CRO of ServiceTitan, Ross Biestman, and Chemistry's Managing Partner and Co-Founder, Kristina Shen, discuss ServiceTitan's founding principles and growth from a small company to a $11 billion vertical SaaS leader. Together they cover ServiceTitan’s mission-driven approach, and its successful adoption of AI for operational efficienc…

1
Startup Failure Patterns, AI Job Risk & Founder-Problem Fit - E607 11:37

1M ago11:37

11:37

Jeremy Au breaks down why most startups fail and what it really takes to succeed in the AI age. He explains the six patterns of startup failure, the tricky economics of service businesses, and why AI will wipe out average workers. He also explores how caring about a problem gives founders their edge and why listening, not output, is the real marker…

1
Daniel Thong: Bootstrapping AI, Spinning Out AI, and Surviving the VC Downturn – E606 45:38

1M ago45:38

45:38

Secure your privacy with Surfshark! Enter coupon code BRAVESEA for an extra 4 months at www.surfshark.com/BRAVESEA Daniel Thong, founder of Nimbus, returns to BRAVE to share how he built a profitable, tech-enabled service business without venture capital. He and Jeremy Au unpack the rise and fall of tech companies like Zilingo, examine the structur…

1
AI Companions, Unicorn Odds, and Southeast Asia’s Next 100 Years of Startups - E605 13:30

1M ago13:30

13:30

Jeremy Au explores how exponential tech progress is reshaping the future, why Southeast Asia is positioned for a surge in unicorns, and how venture capitalists evaluate founders. From AI relationships to realistic startup odds, this discussion challenges assumptions about the next 100 years of innovation and entrepreneurship. 01:15 100 Years of Pro…

1
SaaStr 812: What’s Working Now: AI’s Real Impact on Sales with SaaStr's CEO and Co-Founder, and SVP & GM 47:20

1M ago47:20

47:20

SaaStr 812: What’s Working Now: AI’s Real Impact on Sales with SaaStr's CEO and Co-Founder, and SVP & GM Join Jason Lemkin, CEO and Founder of SaaStr, and Amelia Lerutte, SVP and GM of SaaStr as they dive deep into the practical applications, results, and learnings from integrating AI into sales workflows. This session covers the initial struggles,…

1
Bernard Leong: How AI Is Reshaping Development, Business Models, and Startup Growth – E604 40:46

1M ago40:46

40:46

Secure your privacy with Surfshark! Enter coupon code BRAVESEA for an extra 4 months at www.surfshark.com/BRAVESEA Bernard Leong, founder of Dorje AI and host of Analyse Asia, joins Jeremy Au to explore how AI is transforming software development, business models, and professional roles across Southeast Asia. They break down why dev houses are losi…

1
Saurabh Chauhan: From EF to YC, Beating the Hype & Building AI Finance Agents – E603 40:46

2M ago40:46

40:46

Secure your privacy with Surfshark! Enter coupon code BRAVESEA for an extra 4 months at www.surfshark.com/BRAVESEA Saurabh Chauhan, Co-founder and CEO of Peakflo, returns to BRAVE with Jeremy Au to reflect on their journey since first meeting at Entrepreneur First in 2020. They unpack how Saurabh identified pain points in finance ops during his tim…

1
Double Down or Walk Away: Instacart, Unicorn Portfolios, and Southeast Asia’s Exit Problem - E602 16:23

2M ago16:23

16:23

Jeremy Au breaks down the hidden math behind venture capital: why only a few startups matter, how VCs double down or walk away, and what real exits look like. Using the case of Instacart and Southeast Asia IPOs like SEA, Grab, and GoTo, he explains what separates paper value from cash returns, and why timing is everything. 01:07 VC Fund Economics a…

1
SaaStr 811: Marketing in the Age of AI with Wiz's CMO Raaz Herzberg 41:12

2M ago41:12

41:12

SaaStr 811: Marketing in the Age of AI with Wiz's CMO Raaz Herzberg Join us for an insightful discussion with Raaz Herzberg, the Chief Marketing Officer of Wiz, as she dives into her unconventional journey from engineering to leading Wiz's marketing strategy. In this episode, Raaz shares her unique perspectives on how a lack of traditional marketin…

1
Kelvin Subowo: 7 Failures, Cloud Kitchen Collapse & Building Indonesia’s F&B Avengers – E601 34:25

2M ago34:25

34:25

Kelvin Subowo, CEO of Daily Co., joins Jeremy Au to share how he built one of Indonesia’s fastest growing F&B groups after seven failed ventures. They talk through how Kelvin’s early failures taught him the realities of Indonesia’s price sensitive market, how cloud kitchens initially succeeded but quickly collapsed post-Covid, and how Daily Co. piv…

1
America's VC Wall, Singapore’s Job Crunch & How AI Is Rewiring Relationships with Adriel Yong – E600 44:36

2M ago44:36

44:36

Adriel Yong, Orvel Venture Partner, joins Jeremy Au to reflect on five years of career transitions from investing to building startups across Southeast Asia and the US. They unpack how American venture capital has turned inward, the unintended consequences of remote work, and why AI is upending both work and relationships. Through candid stories fr…

1
Power Struggles in Southeast Asia: VC Rights, Founder Conflicts and the Return of Convertible Debt - E599 12:52

2M ago12:52

12:52

Jeremy Au breaks down the evolving power dynamics between VCs and founders in Southeast Asia, diving into board control, investor rights, and why most startups fail despite support. He shares practical lessons from both sides of the table, highlights the return of convertible debt, and explains how founders should think about conflict, dilution, an…

1
SaaStr 810: AI and the Bottom Line, How Canva Turns Freemium into Conversions with Canva's CCO Rob Giglio 38:13

2M ago38:13

38:13

SaaStr 810: AI and the Bottom Line, How Canva Turns Freemium into Conversions with Canva's CCO Rob Giglio Join John Gleason, founder and managing partner at Success Venture Partners, as he interviews Rob Giglio, Chief Customer Officer at Canva. Rob shares his extensive experience leading customer success, sales, and go-to-market functions at top co…

1
Janine Teo: How AI Empowers Youth, Reinvents Learning & Sparks Motivation – E598 42:08

2M ago42:08

42:08

Janine Teo, CEO of Solve Education, returns to BRAVE after three years to explore how AI is reshaping education for marginalized youth. She and Jeremy Au unpack the double-edged nature of AI in learning, how Solve Education leverages gamification and AI coaching to drive motivation, and the shifting job market where entry-level roles are disappeari…

1
Leaked Power Calls, Cannabis Crackdown & Why Thailand’s Startup Scene Is Quietly Rebooting with Wing Vasiksiri – E597 33:29

2M ago33:29

33:29

Wing Vasiksiri, investor and ecosystem builder, returns to unpack the recent political upheaval in Thailand, the shifting startup landscape, and how these dynamics intersect. He and Jeremy Au explore the Prime Minister’s suspension, the ripple effects of leaked diplomacy, and what these events signal for foreign investment and local sentiment. They…

1
The Funding Game: Mastering SAFE Notes, Board Seats & Control - E596 13:13

2M ago13:13

13:13

Jeremy Au broke down the real stakes behind early-stage fundraising—where founders trade equity for survival, and investors negotiate for control. He explained how financing tools like SAFE notes, convertible notes, and priced rounds shape who gets rich, who gets a say, and who gets left behind. From legal traps to boardroom dynamics, this session …

1
SaaStr 809: Why Enterprise AI Adoption Is Moving 5-10X Faster Than Cloud with Box's CEO and Co-Founder, IBM's VP for AI and SaaStr's CEO and Founder 38:13

2M ago38:13

38:13

SaaStr 809: Why Enterprise AI Adoption Is Moving 5-10X Faster Than Cloud with Box's CEO and Co-Founder, IBM's VP for AI and SaaStr's CEO and Founder This conversation between Aaron Levie, CEO & Co-Founder of Box, Raj Datta, Global Vice President for Software and A.I. Partnerships at IBM and Jason Lemkin, CEO and Founder of SaaStr, covers the evolut…

1
How Vietnam’s Economy is Rewiring for Tech & Trade Battles with Valerie Vu – E595 32:18

2M ago32:18

32:18

Vietnam’s rapid economic transformation is reshaping its future. Valerie Vu, General Partner at Ansible Ventures, joins Jeremy Au to explore how Vietnam is shifting from export dependence to a tech-driven, domestic growth model. They discuss the rollback of anti-corruption campaigns, intensified U.S. trade negotiations, and how food safety scandals…

1
Demographic Collapse, Broken Visas & Why Global Talent Is Rerouting to Southeast Asia – E594 46:46

2M ago46:46

46:46

Shiyan Koh, Managing Partner at Hustle Fund, joins Jeremy Au to examine how geopolitical shifts, demographic decline, and education policy are reshaping global talent and innovation flows. They explore Japan and Korea’s push into Southeast Asia, the unexpected impact of smartphone culture on fertility, and how political actions in the US are disrup…

1
Edtech's Real Buyers, Startup Law Traps and Why Founders Need Better Equity Deals - E593 13:43

2M ago13:43

13:43

Jeremy Au breaks down the hidden risks in Southeast Asia’s edtech sector and early-stage startup law. He explains why edtech often fails to scale, how founder disputes emerge without early agreements, and why choosing the right jurisdiction like Singapore matters for survival. From investor alignment to taxation nightmares, this episode guides foun…

1
SaaStr 808: AI and Cybersecurity: Scaling Rubrik to a Billion Dollar Enterprise with Rubrik's Co-Founder and CTO 25:32

2M ago25:32

25:32

SaaStr 808: AI and Cybersecurity: Scaling Rubrik to a Billion Dollar Enterprise with Rubrik's Co-Founder and CTO In this episode, Kit Colbert, former CTO of VMware and Platform CTO at Invisible, sits down with Arvind  Nithrakashyap, Co-founder and CTO of Rubrik, to discuss the company's journey and innovations over the last 11 years. Arvind  shares…

1
Olzhas (Oz) Zhiyenkul: From Soviet Collapse to Disrupting Global Wealth Tech - E592 33:24

2M ago33:24

33:24

Olzhas (Oz) Zhiyenkul, CEO and co-founder of Investbanq, joins Jeremy Au to share how his journey from post-Soviet Kazakhstan to launching a full-stack wealth operating system was shaped by hardship, global education, and the inefficiencies he witnessed firsthand across Asia’s financial sector. They discuss how legacy systems fail family offices, w…

1
Henry Motte-de la Motte: AI Tutors, Global EdTech, and the $1M Parenting Dilemma – E591 27:07

2M ago27:07

27:07

Henry Motte-de la Motte, CEO of Edge Tutor, and Jeremy Au reconnect two years after their last conversation to discuss how global tutoring has evolved. They examine the rise of AI in education, differences in learner motivation, and how human connection and structure remain critical to learning. They explore Edge Tutor’s expansion into 30 countries…

1
Ilya Kravtsov: Inside Indonesia’s Startup Meltdown, eFishery’s Hidden Fallout & How Real Founders Survive – E590 35:34

3M ago35:34

35:34

Ilya Kravtsov, Co-Founder of Ringkas, joins Jeremy Au to unpack the rise and fall of Indonesia’s lending wave, the ripple effects of the eFishery scandal, and the hard lessons founders must absorb to build sustainable startups. They examine how early hype misaligned business models, how fraud damages more than just a company, and why radical transp…

1
SaaStr 807: Snowflake's CEO on the AI Data Cloud, Partner Strategy, and What’s Next 39:44

3M ago39:44

39:44

SaaStr 807: Snowflake's CEO on the AI Data Cloud, Partner Strategy, and What’s Next Join Sridhar Ramaswamy, CEO of Snowflake, and Jeremy Burton, CEO of Observe, in a comprehensive discussion led by SaaStr CEO & Founder, Jason Lemkin. Discover the inner workings of Snowflake's Board, the dynamics of strategic partnerships, and the evolving role of A…

1
Mohan Belani: Fatherhood as a Founder, Raising AI-Ready Kids & Balancing Marriage with Startup Life – E589 52:27

3M ago52:27

52:27

Mohan Belani, Co-Founder of e27, and Jeremy Au reflect on what it means to be a tech leader, startup founder, and modern dad raising Generation Alpha. They explore how parenting rewires identity, the mental load of fatherhood, and how decision-making feels like startup building in a world flooded with information. They discuss the tension between b…

1
Dr. Gerald Tan: AI Dentistry, Business Betrayal & Rebuilding Trust – E588 37:18

3M ago37:18

37:18

Dr. Gerald Tan, founder of Elite Dental Group and the first Singaporean dentist to graduate from Harvard Business School, joins Jeremy Au to share how dentistry blends science, art, and entrepreneurship. They explore his journey from being one of 30 students in NUS Dentistry to leading an AI-driven public health initiative and surviving a devastati…

1
SaaStr 806: How The Smartest Founders Are Already Winning with AI: SaaStr CEO Jason Lemkin on My First Million 45:53

3M ago45:53

45:53

SaaStr 806: How The Smartest Founders Are Already Winning with AI: SaaStr CEO Jason Lemkin on My First Million SaaStr CEO and Founder Jason Lemkin recently returned to HubSpot's My First Million Podcast with Sam Parr and Shaan Puri to do a deep dive on AI and SaaS. It was a fun one because we approached it more from a content creator and end-user p…