Trailblazers by Erica Wenger

Meka Asonye is the founder and managing partner of Prist Capital, where he backs early-stage companies building breakthrough technologies in aerospace, defense, manufacturing, and other complex industries. His career spans the Cleveland Guardians, Stripe, and First Round Capital.

In this episode of Trailblazers, Meka breaks down his approach to evaluating founders, from recognizing exceptional technical talent to understanding whether someone has the conviction and commercial judgment to build a lasting company.

He also shares the story behind his early investment in K2 Space, explains why traditional venture capital firms can overlook unconventional opportunities, and reveals how competing against better-funded teams in professional baseball shaped his approach to risk and decision-making.

If you're interested in how venture capitalists evaluate startups, what makes a great founder, and where the next generation of deep tech companies could emerge, 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/8dccb81c-ac02-48e1-afb3-b6a7d8ff9160-00b881l8

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
• 00:52 - What Baseball Taught Him About Venture Capital
• 07:36 - Overcoming Personal Challenges and Finding Balance
• 12:06 - From Aviation to Investing in Deep Tech
• 19:59 - Why Meka Left First Round to Start His Own VC Firm
• 25:44 - Why Deep Tech Investing Requires a Different Strategy
• 30:41 - The #1 Thing to Look for When Investing in Startups
• 32:46 - How Meka Spotted the Opportunity in K2 Space
• 39:36 - The Future of Deep Tech and Emerging Startup Hubs
• 42:49 - Building the Future of Prist Capital

Tyler Denk is the co-founder and CEO of beehiiv, a platform helping creators, entrepreneurs, and independent publishers build, grow, and monetize their audiences through newsletters.

In this episode of Trailblazers, Tyler shares what it takes to build and scale a successful startup, why storytelling is one of the most important skills a founder can have, and how creators are turning niche audiences into million-dollar media businesses.

We also discuss how beehiiv builds products at remarkable speed, why newsletters are becoming powerful businesses, how AI could reshape the future of digital media, and how losing his co-founder changed his perspective on leadership and entrepreneurship.

If you're interested in startups, entrepreneurship, the creator economy, newsletters, or building a profitable media business, 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-22&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 - Intro

01:50 - Losing a Co-Founder and Navigating Tragedy

07:03 - Honouring Andrew's Legacy

10:37 - The Secret to Building Products Faster

14:45 - Why Storytelling Is a Founder's Most Important Skill

16:15 - The Reality of Being a Startup CEO

19:56 - How Creators Are Building Million-Dollar Media Businesses

26:54 - How AI Could Disrupt the Future of Media

34:39 - Supporting the Next Generation of Independent Journalism

38:07 - Finding the Right Balance Between Creativity and Growth

44:12 - Why Niche Audiences Are More Valuable Than You Think

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 - Intro
• 00:52 - The Year Everything Went Wrong
• 06:42 - Losing Control and Finding Faith
• 10:32 - Media Literacy and the Next Generation of Entrepreneurs
• 17:19 - From FabFitFun to Investing in Frontier Technology
• 24:50 - Why Michael Is Betting on Hard Tech
• 28:10 - Sovereign AI and the Race for Technological Control
• 34:44 - The US-China Rivalry and the Future of AI
• 38:04 - Why Young People Should Stop Fearing AI
• 46:07 - 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 - Intro
• 3:21 - Battling Perinatal Depression
• 9:36 - Why She Left San Francisco for Nashville
• 13:53 - 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 Backlash
• 35:00 - 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 - Intro
• 6:04 - Does a College Degree Still Matter?
• 9:24 - How Failure Led Sara to Bumble
• 12:05 - Why Authenticity Builds a Stronger Audience
• 19:00 - How Sara & Phil Started Working Together
• 22:14 - From Celebrity Partnerships to Startup Investing
• 27:30 - Why Celebrity Endorsements Are Failing
• 29:02 - Building Oversubscribed Ventures
• 35:08 - How They Choose and Support Their Investments
• 41:38 - Reputation, Founders & Managing Other People’s Money
• 45:57 - The Reality of Being Famous on Social Media
• 51:06 - 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 - Intro
• 06:22 - Why VCs Become Founders and Founders Become VCs
• 08:34 - Building a Venture Firm vs. Running a Fund
• 14:36 - How Andreessen Horowitz Operates Differently
• 15:44 - Why David Joined Andreessen Horowitz and Built Its NYC Office
• 19:53 - What the Best Investment Firms Do Differently
• 26:57 - Why Venture Firms Are Becoming Media Companies
• 28:49 - New York vs. Silicon Valley for Building Startups
• 33:00 - 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 Market
• 44:48 - Why David Looks for “N of 1” Companies
• 46:44 - How David Became an Early Investor in Plaid
• 51:48 - David’s Secret Biochemistry Background
• 56:37 - 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 - Intro
• 03:05 - The Fundraise That Took Jeff Nearly Two Years
• 08:38 - How Jeff Launched One of the First Seed Funds
• 13:26 - Why DPI Matters More Than Paper Markups
• 23:28 - What LPs Actually Want From Emerging Managers
• 26:26 - How to Build a Venture Firm That Outlives You
• 30:45 - Life Outside Venture Capital
• 36:46 - Why Jeff Is Betting on Deep Tech and Hardware
• 43:08 - Why Jeff Passed on Investing in Uber
• 47:45 - How Jeff Led the Seed Round for Postmates
• 51:09 - 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 - Intro
• 05:19 - The Dunning-Kruger Effect
• 11:30 - What Makes or Breaks a Venture Fund
• 12:17 - Why Natalie Doesn't Call Herself a Content Creator
• 15:00 - How Deep Tech Content Went Viral
• 17:50 - Building a Brand Bigger Than Your Product
• 21:04 - Why Human-Made Content Will Matter More
• 24:38 - Thought Leadership vs. Hot Takes
• 27:00 - How to Use AI Without Outsourcing Your Thinking
• 40:48 - What Happens When Scarcity Disappears?
• 43:07 - The Childhood That Shaped How Natalie Thinks
• 48:46 - Why You Can't Predict What Will Go Viral
• 51:17 - Why You Need to Own Your Audience
• 52:36 - 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

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🐘 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
• 01:17 - The Hardest Part of Being a CEO
• 04:46 - The Lonely Reality of Being a CEO
• 09:10 - Building Your Personal Board of Directors
• 10:26 - Why Nirav Returned to Nextdoor
• 13:45 - Building a Tech Company in the Age of AI
• 15:38 - Fear, Failure and Self-Doubt
• 21:18 - What Silicon Valley CEOs Don't Talk About
• 22:48 - Inside Nirav's Monthly CEO Dinners
• 31:04 - Why Nirav Moved His Family to Italy
• 36:38 - Living in Italy When COVID Hit
• 38:09 - Stepping Away From Silicon Valley
• 41:44 - Rebuilding Nextdoor
• 46:53 - Behind the Scenes of Shark Tank
• 51:37 - Mark Cuban, Kevin O'Leary and Entrepreneurship
• 55:34 - Trailblazer Trade-Offs