Trailblazers by Erica Wenger

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, KalshiSydecar: https://sydecar.io/partners/trailblazersbeehiiv: 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-13a7aee11e95-008umkv4Kalshi: http://Kalshi.com/r/trailblazersWispr Flow: https://ref.wisprflow.ai/trailblazersHEX: 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.comTrailblazers 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 - Intro04:58 - How Céline Dion Inspired Brian to Quit His Job08:18 - From a $50 Side Hustle to The Points Guy11:06 - How a NYT Backlink Generated $120K in One Day12:22 - Selling The Points Guy for $28 Million With No VC Funding15:59 - How Credit Card Affiliate Revenue Really Works17:51 - How Media Training Generated Millions in Free Exposure22:45 - Evolving The Points Guy for the AI Era28:49 - How Brian Kelly Became an Angel Investor35:35 - Why Brian Won’t Invest in Celebrity Beverage Brands40:24 - What Brian Looks for in Great Founders43:32 - The Last-Minute Flight Hack That Can Save You Thousands46:19 - Saving $5,000+ on Lufthansa First Class51:31 - 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, KalshiSydecar: https://sydecar.io/partners/trailblazersbeehiiv: 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-4e55e4ef7ef6-00b881l8Kalshi: http://Kalshi.com/r/trailblazersWispr Flow: https://ref.wisprflow.ai/trailblazersHEX: 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.comTrailblazers 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, KalshiSydecar: https://sydecar.io/partners/trailblazersbeehiiv: 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-00b881l8Kalshi: http://Kalshi.com/r/trailblazersWispr Flow: https://ref.wisprflow.ai/trailblazersHEX: 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.comTrailblazers 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, KalshiSydecar: https://sydecar.io/partners/trailblazersbeehiiv: 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-aa06845fd977-008umkv4Kalshi: http://Kalshi.com/r/trailblazersWispr Flow: https://ref.wisprflow.ai/trailblazersHEX: 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.comTrailblazers 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, KalshiSydecar: https://sydecar.io/partners/trailblazersbeehiiv: 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-008umkv4Kalshi: http://Kalshi.com/r/trailblazersWispr Flow: https://ref.wisprflow.ai/trailblazersHEX: 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.comTrailblazers 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, KalshiSydecar: https://sydecar.io/partners/trailblazersbeehiiv: 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-a4e0-2afd6b66c6e1-00b881l8Kalshi: http://Kalshi.com/r/trailblazersWispr Flow: https://ref.wisprflow.ai/trailblazersHEX: 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.comTrailblazers 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 - Intro00:43 - Balancing Name Drops With Execution01:40 - The Hardest Part of Marshall's Journey06:02 - The Reality of Fundraising09:56 - Raising a Fund in a Down Market14:18 - Building the Animal Capital Team15:36 - How Animal Capital Works With Celebrities27:08 - How Marshall Built His Celebrity Network35:26 - Celebrity Influence Beyond Social Media40:49 - The Future of Content and Emerging VC Firms46:06 - Venture Capitalists vs. Asset Managers49:00 - What's Next for Animal Capital55:40 - 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, KalshiSydecar: https://sydecar.io/partners/trailblazersbeehiiv: 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-2026Granola: 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-00b881l8Kalshi: http://Kalshi.com/r/trailblazersWispr Flow: https://ref.wisprflow.ai/trailblazersHEX: 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.comTrailblazers 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 - Intro1:40 - The Hardest Part Of Her Journey7:07 - Transitioning To Substack Full-Time13:52 - The Art of Profiling Polarizing People23:06 - The Role of Vulnerability and Content Serendipity43:52 - The Intersection of Media and Generative AI50:01 - Personal Vulnerability: A Twin Pregnancy Story1:01:29 - 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, KalshiSydecar: https://sydecar.io/partners/trailblazersbeehiiv: 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-0a6176678e84-008umkv4Kalshi: http://Kalshi.com/r/trailblazersWispr Flow: https://ref.wisprflow.ai/trailblazersHEX: 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.comTrailblazers 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 - Intro5:28 - Market Cycles vs. Fund Cycles8:28 - The Rebel Alliance & Open Ecosystems11:18 - The Four Quadrants & Future Of AI12:51 - Programmable Energy Bets14:02 - Renewed Application Layer Conviction18:11 - Public Thinking as Alpha21:39 - Developing and Testing a Thesis27:16 - Changing Market Structures From The Outside In33:26 - Flexibility in Small Fund Sizes35:59 - Selling on the way up39:58 - Building Internal AI Agents47:00 - Data at the Edge Thesis51:46 - 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, KalshiSydecar: https://sydecar.io/partners/trailblazersbeehiiv: 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/trailblazersWispr Flow: https://ref.wisprflow.ai/trailblazersHEX: 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.comTrailblazers 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, KalshiSydecar: https://sydecar.io/partners/trailblazersbeehiiv: 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-fbc5bed34450-008umkv4Kalshi: http://Kalshi.com/r/trailblazersWispr Flow: https://ref.wisprflow.ai/trailblazersHEX: 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.comTrailblazers 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