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Michael Broukhim is the co-founder of FabFitFun and Deep 33, a venture capital firm focused on AI, robotics, and frontier technologies. He's also an early investor in companies like SpaceX and Stripe. In this episode of Trailblazers, Michael explains why AI is becoming a national security priority, how the US and China are competing for technological leadership, and why controlling critical technology matters more than ever. We also discuss the importance of US-Israel tech partnerships, the growing resistance to AI infrastructure, and how his experience building FabFitFun shaped his approach to investing. If you're interested in artificial intelligence, venture capital, AI infrastructure, or emerging technologies, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-21&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers! Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro00:52 - The Year Everything Went Wrong06:42 - Losing Control and Finding Faith10:32 - Media Literacy and the Next Generation of Entrepreneurs17:19 - From FabFitFun to Investing in Frontier Technology24:50 - Why Michael Is Betting on Hard Tech28:10 - Sovereign AI and the Race for Technological Control34:44 - The US-China Rivalry and the Future of AI38:04 - Why Young People Should Stop Fearing AI46:07 - Information Warfare and the Battle for Global Power

Nichole Wischoff is the founder of Wischoff Ventures, an early-stage venture capital firm investing in overlooked industries. She's grown the firm from a $5M first fund to a $50M third fund. In this episode of Trailblazers, Nichole explains why great startup ideas can make bad investments, how she finds promising founders before other VCs, and why Silicon Valley can actually hurt early-stage investors. We also discuss her journey from growing up on food stamps to building a venture firm, her decision to leave San Francisco for Nashville, and the personal challenges of balancing motherhood, mental health, and entrepreneurship. If you're interested in venture capital, entrepreneurship, startup investing, founder evaluation, fundraising, Silicon Valley, or building a venture capital firm, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: http://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-20&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers! Check out the episode show notes here: https://notes.granola.ai/t/287d5390-612b-44e7-bfbf-51da8cde9116-00b881l8 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro3:21 - Battling Perinatal Depression9:36 - Why She Left San Francisco for Nashville13:53 - Inside Wischoff Ventures 16:46 - How Nichole Finds and Evaluates Startups 18:54 - Why Being the First Investor Matters 21:24 - Building a Network That Shares VC Deals 25:43 - Why Venture Capital Content Is Changing 29:30 - The Problem With Scripted Podcasts 31:13 - Dealing With Online Criticism and Backlash35:00 - The Keith Rabois Incident and Lessons in Resilience

In this episode, we sit down with Sara Foster and Phil Schwarz, co-founders of Oversubscribed Ventures, alongside GP Erin Foster. We discuss how celebrity, media, and traditional venture capital are coming together to build a different model for investing in consumer companies. Sara brings a background in entertainment, brand building, and consumer influence, while Phil brings decades of experience across technology, marketing, and venture capital, including serving as CMO of Tinder and Partner at Corazon Capital. Together, they break down why they started Oversubscribed Ventures, how they evaluate and support companies, and why millions of followers no longer guarantee that a product will sell. We also discuss how AI could change the value of college degrees and entry-level jobs, what founders should expect from celebrity investors, how reputation travels through venture capital, and why they see major opportunities in consumer products and women’s health. If you're interested in venture capital, entrepreneurship, consumer investing, celebrity brands, AI, startups, or the creator economy, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-19&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers. Check out the episode show notes here: https://notes.granola.ai/t/db5d5620-36a4-4796-9ed6-408c6d55d3ad-00b881l8 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro6:04 - Does a College Degree Still Matter?9:24 - How Failure Led Sara to Bumble12:05 - Why Authenticity Builds a Stronger Audience19:00 - How Sara & Phil Started Working Together22:14 - From Celebrity Partnerships to Startup Investing27:30 - Why Celebrity Endorsements Are Failing29:02 - Building Oversubscribed Ventures35:08 - How They Choose and Support Their Investments41:38 - Reputation, Founders & Managing Other People’s Money45:57 - The Reality of Being Famous on Social Media51:06 - Why They’re Betting on Women’s Health & Consumer Products

In this episode, we sit down with David Haber, General Partner at Andreessen Horowitz and former founder of Bond Street, to discuss what separates exceptional founders from everyone else. David breaks down why the best founders study those who came before them, how to stand out in crowded markets, what makes an “N of 1” company, and the biggest mistakes founders make when hiring. We also discuss building and selling Bond Street, New York vs. Silicon Valley, and how AI is changing what it takes to build a successful company. If you're interested in entrepreneurship, startups, venture capital, founder advice, hiring, AI, or building a successful company, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-18&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers! Check out the episode shownotes here: https://notes.granola.ai/t/18b4e05d-a30c-4192-85f7-f5db17f34f4f-00b881l8 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro06:22 - Why VCs Become Founders and Founders Become VCs08:34 - Building a Venture Firm vs. Running a Fund14:36 - How Andreessen Horowitz Operates Differently15:44 - Why David Joined Andreessen Horowitz and Built Its NYC Office19:53 - What the Best Investment Firms Do Differently26:57 - Why Venture Firms Are Becoming Media Companies28:49 - New York vs. Silicon Valley for Building Startups33:00 - Does Domain Expertise Still Matter in the Age of AI?41:19 - What Makes a Founder Stand Out?43:24 - How to Win in a Crowded Market44:48 - Why David Looks for “N of 1” Companies46:44 - How David Became an Early Investor in Plaid51:48 - David’s Secret Biochemistry Background56:37 - Trailblazer Trade-Offs

In this episode, we sit down with Jeff Clavier, founder of Uncork Capital and one of the early pioneers of seed-stage venture capital. Jeff shares what he has learned from more than two decades of investing in startups, from raising some of the earliest institutional seed funds to backing companies like Postmates and Fitbit. We get into the realities of raising a venture fund, what LPs look for in emerging managers, why DPI and returning actual capital matter more than paper markups, and how secondaries can create liquidity for investors. Jeff also breaks down his approach to deep tech and hardware investing, the opportunity he missed with Uber, and how he planned the transition of Uncork to its next generation of leadership. If you're interested in venture capital, raising a VC fund, seed investing, emerging managers, LP fundraising, startup investing, fund economics, DPI, secondaries, or building a long-term career in venture, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-17&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers! Checkout the episode shownotes here: https://notes.granola.ai/t/cd9f769d-33de-4ef8-abe9-57baa929cc4f-00b881l8 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro03:05 - The Fundraise That Took Jeff Nearly Two Years08:38 - How Jeff Launched One of the First Seed Funds13:26 - Why DPI Matters More Than Paper Markups23:28 - What LPs Actually Want From Emerging Managers26:26 - How to Build a Venture Firm That Outlives You30:45 - Life Outside Venture Capital36:46 - Why Jeff Is Betting on Deep Tech and Hardware43:08 - Why Jeff Passed on Investing in Uber47:45 - How Jeff Led the Seed Round for Postmates51:09 - Trailblazer Trade-Offs

In this episode, we sit down with Brian Kelly, founder of The Points Guy, to break down the business behind one of the most recognizable brands in travel and credit card rewards. Brian shares how The Points Guy actually makes money, why affiliate marketing became such a powerful business model, and how he built trust with an audience that credit card companies wanted to reach. We also discuss his decision to sell the company for $28 million, the advantages of bootstrapping instead of raising venture capital, using media and SEO to grow a brand, and how his experience building TPG shaped the way he now approaches angel investing. Later, Brian shares practical strategies for maximizing credit card points, finding award availability, and booking business and first-class flights for significantly less. If you're interested in entrepreneurship, affiliate marketing, online businesses, credit card rewards, travel hacking, angel investing, SEO, or building a valuable audience, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-1&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) beehiiv: www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-16&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers. Checkout the episode shownotes here: https://notes.granola.ai/t/dad0c1f2-3590-415e-b2ee-13a7aee11e95-008umkv4 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro 04:58 - How Céline Dion Inspired Brian to Quit His Job 08:18 - From a $50 Side Hustle to The Points Guy 11:06 - How a NYT Backlink Generated $120K in One Day 12:22 - Selling The Points Guy for $28 Million With No VC Funding 15:59 - How Credit Card Affiliate Revenue Really Works 17:51 - How Media Training Generated Millions in Free Exposure 22:45 - Evolving The Points Guy for the AI Era 28:49 - How Brian Kelly Became an Angel Investor 35:35 - Why Brian Won’t Invest in Celebrity Beverage Brands 40:24 - What Brian Looks for in Great Founders 43:32 - The Last-Minute Flight Hack That Can Save You Thousands 46:19 - Saving $5,000+ on Lufthansa First Class 51:31 - Trailblazer Trade-Offs

In this episode, we sit down with Natalie Fratto, an investor, writer, and new media entrepreneur known for translating complex ideas across technology, venture capital, and culture to a growing online audience. We discuss why most content fails, how the power law drives viral growth, why Natalie doesn't consider herself a traditional content creator, and how deep tech found a massive audience on social media. We also get into the difference between thought leadership and hot takes, using AI without outsourcing your thinking, why human-made content could become more valuable in the AI era, and what companies like Red Bull and Stripe understand about building brands beyond their products. If you're interested in venture capital, technology, AI, content creation, social media, personal branding, audience growth, or how media and creativity are changing in the AI era, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-15&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers! Check out the episode show notes here: https://notes.granola.ai/t/22214880-1126-4ade-b61d-4e55e4ef7ef6-00b881l8 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro05:19 - The Dunning-Kruger Effect11:30 - What Makes or Breaks a Venture Fund12:17 - Why Natalie Doesn't Call Herself a Content Creator15:00 - How Deep Tech Content Went Viral17:50 - Building a Brand Bigger Than Your Product21:04 - Why Human-Made Content Will Matter More24:38 - Thought Leadership vs. Hot Takes27:00 - How to Use AI Without Outsourcing Your Thinking40:48 - What Happens When Scarcity Disappears?43:07 - The Childhood That Shaped How Natalie Thinks48:46 - Why You Can't Predict What Will Go Viral51:17 - Why You Need to Own Your Audience52:36 - Trailblazer Trade-Offs

In this episode, we sit down with Nirav Tolia, co-founder and CEO of Nextdoor and a longtime Silicon Valley entrepreneur who previously co-founded Epinions, which became Shopping.com. We discuss the lonely reality of being a CEO, building and rebuilding companies through failure, why Nirav returned to Nextdoor after years away, navigating fear and self-doubt as a leader, and how established technology companies can adapt in the age of AI. We also get into his time on Shark Tank, working alongside Mark Cuban and Kevin O'Leary, and what stepping away from Silicon Valley taught him about business and life. If you're interested in entrepreneurship, startups, leadership, Silicon Valley, AI, Shark Tank, building companies, or understanding what it's really like to lead a business through its hardest moments, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-14&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers! Check out the episode show notes here: https://notes.granola.ai/t/55838edb-522f-4468-a139-fad215bab7ca-00b881l8 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro01:17 - The Hardest Part of Being a CEO04:46 - The Lonely Reality of Being a CEO09:10 - Building Your Personal Board of Directors10:26 - Why Nirav Returned to Nextdoor13:45 - Building a Tech Company in the Age of AI15:38 - Fear, Failure and Self-Doubt21:18 - What Silicon Valley CEOs Don't Talk About22:48 - Inside Nirav's Monthly CEO Dinners31:04 - Why Nirav Moved His Family to Italy36:38 - Living in Italy When COVID Hit38:09 - Stepping Away From Silicon Valley41:44 - Rebuilding Nextdoor46:53 - Behind the Scenes of Shark Tank51:37 - Mark Cuban, Kevin O'Leary and Entrepreneurship55:34 - Trailblazer Trade-Offs

In this episode, we sit down with Jack Raines, investor at Slow Ventures and author of Young Money, a book about navigating the career, money, and life decisions that define your 20s. We discuss how to avoid wasting your 20s, why you should spend more money while you're young, how to balance ambition with adventure, how to know when you're on the wrong career path, and why building a personal brand without real substance can become a career liability. If you're interested in careers, money, investing, entrepreneurship, venture capital, personal branding, AI, or making better decisions in your 20s, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-13&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers! Check out the episode's show notes here: https://notes.granola.ai/t/5d11c7d5-3a1a-4c00-bbfa-aa06845fd977-008umkv4 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro01:04 - The Reality of Writing a Book05:19 - Why Jack Wrote Young Money09:13 - Why You Should Spend More in Your 20s13:33 - Ambition vs. Adventure17:14 - How to Know You're on the Wrong Career Path20:00 - How a LinkedIn Joke Landed Jack a Book Deal25:48 - Why Humor Matters in Venture Capital30:04 - How Slow Ventures Thinks About Personal Brands33:58 - When Personal Branding Goes Too Far40:37 - Why Jack Is Bullish on Legal AI46:49 - Trailblazer Trade-Offs

In this episode, we sit down with Nadya Okamoto, serial entrepreneur and creator who founded PERIOD at 16, went on to build period care brand August, and is now Co-Founder and CMO of social app Pie. We discuss why every founder should become a creator, how building an audience can become a competitive advantage, why posting more can outperform perfect content, the unglamorous reality of building a startup, and why the next generation of companies will need to compete for attention. If you're interested in entrepreneurship, startups, content creation, social media, marketing, personal branding, or understanding how attention can become a business advantage, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-12&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers! Check out the episode show notes here: https://notes.granola.ai/t/744dba26-26b1-4095-aee4-3d54531745fb-008umkv4 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro01:11 - When Your Personal Life Becomes Content03:29 - Why Nadya Posts So Much Content06:35 - How Social Media Algorithms Have Changed08:30 - The Cost of Building in Public10:33 - Founder vs. Content Creator13:56 - What Is a Social Entrepreneur?18:58 - Building Pie With Andy Dunn21:27 - The Myth of the “Celebrity CEO”23:48 - Why Traditional Marketing Is Too Slow26:06 - How Nadya Is Everywhere Online33:52 - Mental Health in Entrepreneurship36:58 - Building and Scaling August38:00 - Turning a Running Club Into a Business41:21 - Trailblazer Trade-Offs

In this episode, we sit down with Marshall Sandman, founder and Managing Partner of Animal Capital, a seed-stage venture firm whose first fund backed four unicorns and ranked in the top 1% of its vintage. We discuss how Marshall built a venture firm backed by some of the world's most recognizable celebrities and entrepreneurs, the reality of raising a fund in a down market, why most founders should bootstrap instead of raising venture capital, what separates venture capitalists from asset managers, and why he believes today's AI market is overhyped. If you're interested in venture capital, startups, fundraising, investing, AI, or understanding how top-performing venture firms are built, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-11&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers. Check out the episode shownotes here: https://notes.granola.ai/t/dff2aba0-4c29-498b-a4e0-2afd6b66c6e1-00b881l8 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro 00:43 - Balancing Name Drops With Execution 01:40 - The Hardest Part of Marshall's Journey 06:02 - The Reality of Fundraising 09:56 - Raising a Fund in a Down Market 14:18 - Building the Animal Capital Team 15:36 - How Animal Capital Works With Celebrities 27:08 - How Marshall Built His Celebrity Network 35:26 - Celebrity Influence Beyond Social Media 40:49 - The Future of Content and Emerging VC Firms 46:06 - Venture Capitalists vs. Asset Managers 49:00 - What's Next for Animal Capital 55:40 - Trailblazer Trade-Offs

In this episode, we sit down with Polina Pompliano, founder of The Profile and author of Hidden Genius, where she studies the lives, habits, and minds of exceptional people. We discuss what drives some of the world's most successful people, how putting yourself out there creates unexpected opportunities, why flaws and insecurities can become an advantage, the role of vulnerability in storytelling, and how to use AI without letting it think for you. If you're interested in entrepreneurship, media, AI, storytelling, personal growth, or understanding what makes exceptional people different, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-1&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) *beehiiv has a major announcement coming July 16 - can't say more, but you won't want to miss it. RSVP here: https://www.beehiiv.com/summer-release-2026 Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers! Check out the episode show notes here: https://notes.granola.ai/t/ed6c5333-9e78-42fe-850f-8910c833df7b-00b881l8 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro 1:40 - The Hardest Part Of Her Journey 7:07 - Transitioning To Substack Full-Time 13:52 - The Art of Profiling Polarizing People 23:06 - The Role of Vulnerability and Content Serendipity 43:52 - The Intersection of Media and Generative AI 50:01 - Personal Vulnerability: A Twin Pregnancy Story 1:01:29 - Trailblazer Trade-offs

In this episode, we sit down with Rebecca Kaden, General Partner at Union Square Ventures, where she invests in the next generation of AI, software, and technology companies shaping the future. We discuss why AI is still dramatically underhyped, how venture capitalists identify world-changing technologies before everyone else, the future of open versus closed AI ecosystems, why the best investors think in decades instead of years, and the frameworks Rebecca uses to evaluate the next wave of billion-dollar companies. If you're interested in AI, venture capital, startups, investing, or understanding how the world's best investors think, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-9&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers! Check out the episode's show notes here: https://notes.granola.ai/t/53b581cd-316f-4211-967c-0a6176678e84-008umkv4 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Timestamps: 00:00 - Intro 5:28 - Market Cycles vs. Fund Cycles 8:28 - The Rebel Alliance & Open Ecosystems 11:18 - The Four Quadrants & Future Of AI 12:51 - Programmable Energy Bets 14:02 - Renewed Application Layer Conviction 18:11 - Public Thinking as Alpha 21:39 - Developing and Testing a Thesis 27:16 - Changing Market Structures From The Outside In 33:26 - Flexibility in Small Fund Sizes 35:59 - Selling on the way up 39:58 - Building Internal AI Agents 47:00 - Data at the Edge Thesis 51:46 - Trailblazer Trade-offs

In this episode, we sit down with John Hu, the co-founder and CEO of Stan, the platform helping creators turn their audience into thriving businesses. We discuss how AI is changing entrepreneurship, why the best companies stay relentlessly founder-first, what it takes to build a $40M business with just 30 employees, the future of creator entrepreneurs, the importance of distribution and personal branding, and the principles behind building products people genuinely love. If you're interested in entrepreneurship, AI, startups, the creator economy, or building high-growth businesses, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-8&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers. Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro01:09 - Workplace Philosophy and Surfing Culture05:33 - The Founder-First Northstar Value08:23 - The Spectrum of Creator Entrepreneurs09:57 - Durability of Personal Branding at Scale12:40 - AI Content Creation Workflows15:53 - Building "Stanley": The Pocket AI Content Team18:10 - Marketing Breakthroughs vs Saturated Insights22:36 - Cold Outreach and Fundraising with Steven Bartlett26:47 - Career Expectations and dropper-out from Stanford Business School30:37 - Growing Up with a Single, Hardworking Immigrant Mother31:59 - Redefining Self-Worth, Fulfillment, and Corporate Plateaus41:14 - Creator Payout Success Stories on Stan44:04 - Trailblazers Trade-offs

In this episode, we sit down with Nicole Behnam, an entrepreneur, investor, and podcast host known for interviewing some of the world's top founders, investors, and business leaders. We discuss how to build relationships with influential people, why traditional education leaves entrepreneurs at a disadvantage, the future of AI and entrepreneurship, the power of storytelling, how to build a cult-like brand, and the mindset behind building one of the strongest networks in tech. If you're interested in entrepreneurship, AI, networking, business, or learning how successful founders think, this episode is for you. This episode is supported by Sydecar, HEX, Wispr Flow, Granola, Beehiiv, Kalshi Sydecar: https://sydecar.io/partners/trailblazers beehiiv: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-7&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF) Granola: http://granola.ai/trailblazers *Granola is the official notetaker of Trailblazers. Check out the episode show notes here: https://notes.granola.ai/t/b7b67559-e75a-4321-a59e-fbc5bed34450-008umkv4 Kalshi: http://Kalshi.com/r/trailblazers Wispr Flow: https://ref.wisprflow.ai/trailblazers HEX: http://hex.ai/trailblazers 🎧 Listen on Apple Podcasts: https://apple.trailblazerspod.com 🎧 Listen on Spotify: https://spotify.trailblazerspod.com 📲 Follow on TikTok: https://tiktok.trailblazerspod.com ▶️ Subscribe on YouTube: https://youtube.trailblazerspod.com 📸 Follow on Instagram: https://instagram.trailblazerspod.com 🐘 Learn more about Park Rangers Capital: https://parkrangerscap.com Trailblazers is your favorite tech + VC podcast, hosted by Erica Wenger (GP at Park Rangers Capital). Each week we sit down with founders, operators, and investors who’ve found conventional success in unconventional ways. New episodes every Tuesday. Enjoy! Timestamps: 00:00 - Intro01:00 - Strengths & Weaknesses 03:00 - Finding Mentors & The Power of Being Bold07:12 - Admitting Weaknesses & The Sales Mindset10:04 - Deciding to Ditch Traditional Journalism14:58 - Spotting Generational Talent Early18:04 - What School Forgot to Teach Us20:58 - Getting Access to Elite Investment Circles23:20 - Throwing a Private Event for Naval Ravikant30:10 - Why Nicole’s Interviews Are Radically Different32:00 - Is AI Going to Take Your Job?37:42 - Standing Up for Human Rights in Iran40:50 - How Algorithms Are Weaponizing Our Anger43:40 - Why Tech Has a Serious PR Problem46:14 - The Surprising Truth About Andrew Tate & Cult Branding49:58 - Lightning Round: Trailblazer Trade-offs54:53 - Final Thoughts: AI Abundance vs. Chaos