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-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
• 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

🎧 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
• 01:17 - 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

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 - Intro
• 01:04 - The Reality of Writing a Book
• 05:19 - Why Jack Wrote Young Money
• 09:13 - Why You Should Spend More in Your 20s
• 13:33 - Ambition vs. Adventure
• 17:14 - How to Know You're on the Wrong Career Path
• 20:00 - How a LinkedIn Joke Landed Jack a Book Deal
• 25:48 - Why Humor Matters in Venture Capital
• 30:04 - How Slow Ventures Thinks About Personal Brands
• 33:58 - When Personal Branding Goes Too Far
• 40:37 - Why Jack Is Bullish on Legal AI
• 46:49 - 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 - Intro
• 01:11 - When Your Personal Life Becomes Content
• 03:29 - Why Nadya Posts So Much Content
• 06:35 - How Social Media Algorithms Have Changed
• 08:30 - The Cost of Building in Public
• 10:33 - Founder vs. Content Creator
• 13:56 - What Is a Social Entrepreneur?
• 18:58 - Building Pie With Andy Dunn
• 21:27 - The Myth of the “Celebrity CEO”
• 23:48 - Why Traditional Marketing Is Too Slow
• 26:06 - How Nadya Is Everywhere Online
• 33:52 - Mental Health in Entrepreneurship
• 36:58 - Building and Scaling August
• 38:00 - Turning a Running Club Into a Business
• 41:21 - 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 - Intro
• 01:09 - Workplace Philosophy and Surfing Culture
• 05:33 - The Founder-First Northstar Value
• 08:23 - The Spectrum of Creator Entrepreneurs
• 09:57 - Durability of Personal Branding at Scale
• 12:40 - AI Content Creation Workflows
• 15:53 - Building "Stanley": The Pocket AI Content Team
• 18:10 - Marketing Breakthroughs vs Saturated Insights
• 22:36 - Cold Outreach and Fundraising with Steven Bartlett
• 26:47 - Career Expectations and dropper-out from Stanford Business School
• 30:37 - Growing Up with a Single, Hardworking Immigrant Mother
• 31:59 - Redefining Self-Worth, Fulfillment, and Corporate Plateaus
• 41:14 - Creator Payout Success Stories on Stan
• 44:04 - 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 - Intro
• 01:00 - Strengths & Weaknesses 
• 03:00 - Finding Mentors & The Power of Being Bold
• 07:12 - Admitting Weaknesses & The Sales Mindset
• 10:04 - Deciding to Ditch Traditional Journalism
• 14:58 - Spotting Generational Talent Early
• 18:04 - What School Forgot to Teach Us
• 20:58 - Getting Access to Elite Investment Circles
• 23:20 - Throwing a Private Event for Naval Ravikant
• 30:10 - Why Nicole’s Interviews Are Radically Different
• 32:00 - Is AI Going to Take Your Job?
• 37:42 - Standing Up for Human Rights in Iran
• 40:50 - How Algorithms Are Weaponizing Our Anger
• 43:40 - Why Tech Has a Serious PR Problem
• 46:14 - The Surprising Truth About Andrew Tate & Cult Branding
• 49:58 - Lightning Round: Trailblazer Trade-offs
• 54:53 - Final Thoughts: AI Abundance vs. Chaos

In this episode, we sit down with Geoff Woo, Co-Founder and Managing Partner of Antifund, an unconventional venture capital firm investing in the next generation of companies across technology, consumer, defense, and culture. Geoff is also the Founder and Executive Chairman of Ketone-IQ and has built businesses alongside creators like Jake and Logan Paul, giving him a unique perspective at the intersection of venture capital, entrepreneurship, and internet culture.

We discuss why venture capital is "high-class begging," how Antifund uses celebrity partnerships to win the most competitive startup deals, why attention is becoming more valuable than capital, how AI is changing the future of startups and human expertise, the philosophy behind Ketone-IQ, and the mindset founders need to build category-defining companies.

If you're interested in startups, venture capital, AI, entrepreneurship, creator businesses, or learning how top 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: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-6&stripe_campaign_code=TRAILBLAZERS30 (or use code “trailblazers30” for 30% OFF)

*Granola is the official notetaker of Trailblazers! 

Check out the episode show notes here: https://notes.granola.ai/t/7b44b7f3-ac56-487b-befa-81d024355e49-00b881l8

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:

0:00 - Intro

00:42 - Personal Strengths, Weaknesses, and Focus

6:53 - IQ vs EQ in Venture Capital

12:22 - The "Celebrity GP" Thesis & Value Add

23:08 - Antifund Structure & Incubations

29:27 - Meeting the Paul Brothers & The Origins of Antifund

43:13 - The Philosophy Behind the "Antifund" Name

48:37 - Ketone-Based Nutrition & Silicon Valley Fasting

51:19 Rapid Fire Questions

In this episode, we sit down with Ann Miura-Ko, Co-Founding Partner of Floodgate and one of Silicon Valley's earliest investors in companies like Lyft, Twitch, Twitter, and Okta. After nearly two decades investing in founders at the earliest stages of company building, Ann shares how she identifies exceptional entrepreneurs long before the rest of the market. We discuss how Twitch almost never happened, the early rivalry between Uber and Lyft, why the best entrepreneurs are truth seekers, the future of AI-pilled organizations, what teaching has revealed about curiosity and character, and how Ann thinks about investing in the next generation of world-changing companies. If you're interested in startups, venture capital, AI, or understanding how the 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: https://www.beehiiv.com/splash?utm_campaign=trailblazers-2026-Partnership&utm_medium=podcast&utm_source=trailblazers&utm_term=podcast-5&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/d1fb3aec-f1c5-4681-b763-af05df15ac3d-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:

0:00 Intro 

0:41 The AI Pilled Organization 

6:09 The Biggest Barrier to AI Adoption

8:41 The Rise of the Non-Technical Founders

10:32 How To Find Super-Thinkers

12:30 Why Ann Loves Teaching 

13:36 Stanford Mayfield Program

16:25 Getting Pitched By A 14-Year-Old

18:52 Different Types Of Leadership 

23:29 Early Investment In Twitter 

24:42 Why Twitch Never Should Have Worked

27:01 Ann’s 10,000x Return From Lyft Investment 

30:00 Inside the Uber vs. Lyft Rivalry

33:25 Ann’s Investment Philosophy  

35:52 Investing In Lyft At $5M Valuation 

39:10 Staying Disciplined On Fund Size 

47:49 Evaluating Companies After The Investment

51:29 Ann’s Partnership With Mike Maples 

1:03:27 Rapid Fire Questions

In this episode, we sit down with Kate McAndrew, Co-Founder and General Partner of Baukunst, a $100 million pre-seed venture fund investing in the next generation of founders. After spending more than a decade investing in over 100 early-stage companies, Kate shares how she evaluates entrepreneurs long before the rest of the market catches on. We discuss what makes a startup worth investing in, how great investors think from first principles, the traits that separate exceptional founders, how to build company cultures and institutions that last, and the unconventional path that led her into venture capital. If you're interested in startups, investing, entrepreneurship, or understanding how the best venture capitalists 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-4&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/860f1c91-f717-41cd-a6c1-567458bfb806-00b881l8

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.

Timestamps:

0:00 Intro

1:37 Kate’s Biggest Struggle

3:55 How Going To An All-Girls School Impacted Kate's Life

8:38 What Going To An All-Girls School Is Actually Like

11:21 How Kate Thinks About Investing

12:41 What Makes A Great Founder

14:23 How Companies Survive 100+ Years

17:14 Kate’s Unconventional Path To VC

23:15 The Philosophy Of Building A Great Company

27:54 How Kate Got Her First Job In VC

30:04 Kate’s Best Advice For Entrepreneurs

33:29 What Makes A Brand’s Identity

36:49 Why Kate Makes Content

43:30 The Purpose Behind Baukunst

48:04 How Baukunst Operates Internally

52:34 What Kate’s Most Excited To Invest In

54:57 Every VC Hates A Creator Business

In this episode, we sit down with Nas Daily, entrepreneur, creator, and founder of one of the world's largest creator brands. After building an audience of more than 70 million followers through nearly a decade of daily videos, Nas made the biggest gamble of his career by pivoting his content to AI. We discuss why he believes AI will create the next Walt Disney, how he built and manages a company with more than 100 employees, the philosophy behind Nas Daily, the family gamble that got him into Harvard, his perspective on the Israel-Palestine conflict, and how he thinks about storytelling, leadership, and the future of content. If you're interested in entrepreneurship, the creator economy, AI, or building a business that stands the test of time, 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-3&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/153edc4e-bc9a-410d-8f94-f9aea61e8cfd-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.

Timestamps:

0:00 Intro 

1:45 Nas Is Very Opinionated

4:40 How To Actually Create Company Culture

5:56 Nas Hasn’t Changed His T-Shirt In 9 Years

8:40 Asking People Their Net Worth Should Be Normal 

9:21 How Nas Chooses What Products To Build 

13:52 Why Justin Bieber’s Business Failed

16:09 Predicting What Type Of Founders Will Be Successful 

17:13 How Nas Daily Hires Employees 

18:05 Why AI Agencies Suck

21:16 The Biggest Risk Nas Daily Ever Took 

24:10 How Nas Daily Closed Series A Investment 

29:31 The Passing Of Zaki Djemal 

32:40 The Importance Of Believing In Yourself 

36:20 Why Nas Boycott YouTube For 2 Years 

38:37 Discussing The Israel-Palestine Conflict 

49:04 Growing Up In Israel 

51:08 How Nas Ended Up Going To Harvard 

52:43 North Korea Vs Israel 

54:47 Rapid Fire Questions

In this episode, we sit down with Justin Welsh, entrepreneur, writer, and founder of a $15 million one-person business. After helping build two billion-dollar companies and raising more than $300 million in venture capital, Justin chose a different path; one focused on freedom, leverage, and ownership. We discuss the power of writing, the future of entrepreneurship in the age of AI, why many founders are building the wrong businesses, and how to create wealth without sacrificing your time, health, and relationships. If you want to build a business that supports your life instead of consuming it, 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-2&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/5998b389-aaa5-4d9c-bc58-a7ff3230378c-009c2hma

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:

0:00 Intro

0:58 The Hardest Part In Justin’s Journey

2:17 Knowing When Something Has To Change

3:57 How Justin’s Wife Helped Build Their $15M Business

5:44 Revenue Sources

8:05 Learning How To Build Work-Life Balance

10:46 How AI Tools Impact Writing

16:40 The Most Valuable Social Platform

24:00 Justin’s Favourite Piece Of Writing

26:35 The Biggest Problem Founders Face Today

30:07 How To Give Value To Your Clients

31:59 Everyone Is So Bombastic

35:08 How Justin Chooses What Businesses To Invest In

39:10 Clients Love Being Part Of A Community

41:29 Building A $15M Business Alone

43:44 Healing From Burnout

48:41 Rapid Fire Questions

In this episode, we sit down with Mark Cuban to uncover the principles behind his success in business. From whether entrepreneurs should drop out of school to the toughest challenges he faced while building his companies, Mark shares the lessons that shaped his career. He explains why curiosity is a competitive advantage, how ego can hold people back, and what separates successful entrepreneurs from everyone else. If you're looking to build a business, advance your career, or think differently about success, 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-2&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/5998b389-aaa5-4d9c-bc58-a7ff3230378c-009c2hma

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:

0:00 Intro

1:25 Mark Cuban’s Biggest Professional Challenge 

4:14 Should Entrepreneurs Go To School?

7:26 How AI Is Impacting Education

14:26 Why Women Athletes Make Great CEO’s

15:40 Clavicular Getting Frame Mogged By ASU Frat Leader

16:44 When To Start A Company

20:59 AI Slop

26:08 The Dark Side Of AI

29:19 How Mark Cuban Is Fighting Big Pharma

33:03 Rich People Always Fail In Healthcare

37:23 Business Changes The World More Than Politics

44:57 Mark Cuban’s Advice For 20 Year Olds

53:46 Tech Wars 

1:01:15 Rapid Fire Question

This week, we chat with Leah Solivan!

Leah is the founder of TaskRabbit, the pioneering on-demand marketplace that helped redefine the future of work and laid the foundation for what we now know as the gig economy. As CEO for eight years, she scaled TaskRabbit into an international business operating in more than 40 cities before overseeing its successful acquisition by IKEA in 2017.

Today, Leah continues to build and back world-changing companies as Managing Director of Precedent.vc, General Partner at Fuel Capital, and founder of The Precedent Collective. Across her investing career, she’s supported more than 150 companies spanning consumer technology, marketplaces, hardware, education, and retail, including companies like Nanit, Pacaso, Our Place, Good Dog, and Upwards.

Before founding TaskRabbit, Leah began her career as a software engineer at IBM, where she worked on products like Lotus Notes and Domino, building the technical foundation that would later shape her journey as a founder and investor.

Leah is also a passionate advocate for diversity in technology and entrepreneurship, proudly representing her Latina heritage and speaking globally on topics like the future of work, innovation, and leadership.

✨ This episode is presented by Brex.

Brex: brex.com/trailblazerspod

This episode is supported by RocketReach, Gusto, OpenPhone & Athena.

RocketReach: rocketreach.co/trailblazers

Gusto: gusto.com/trailblazers

Quo: Quo.com/trailblazers

Athena: athenago.me/Erica-Wenger

Follow Us!

Leah Solivan: @labunleashed

Breaking Precedent Podcast: https://www.breakingprecedent.com/

https://truthorlie.ai/

@thetrailblazerspod: Instagram, YouTube, TikTok

Erica Wenger: @erica_wenger

This week, we chat with Mariam Naficy!

A serial entrepreneur and visionary leader known for pioneering new ways to connect creativity, technology, and human expression. Mariam is the Founder and Chairman of Minted, and now the Founder and CEO of Arcade, a platform that uses AI to help people communicate visually — transcending geographic and language barriers to connect creators, artisans, and consumers worldwide.

For Mariam, Arcade is a full-circle moment. Having grown up overseas exploring marketplaces and bazaars, she developed a lifelong love of handcrafted objects and the stories behind them. At Arcade, she’s bringing that passion to life — using technology to foster deeper human connection. By training models for makers like Christofle, Bitossi Ceramiche, Cabana, and Anastasio Home, as well as manufacturers around the world, Arcade empowers anyone to create meaningful, personal objects that reflect individual taste and creativity.

Before founding Arcade, Mariam built some of the Internet’s most influential creative brands over the past several decades. She founded and built Minted, the design marketplace that revolutionized the creator economy and became a several hundred million dollar business, and co-founded Eve.com, the very first online cosmetics retailer in the world, in 1998.

At the heart of her work is a belief that technology, when used thoughtfully, can bring meaning, beauty, and connection into people’s lives—as well as create meaningful income for others, such as the Minted artist community.

✨ This episode is presented by Brex.

Brex: brex.com/trailblazerspod

This episode is supported by RocketReach, Gusto, OpenPhone & Athena.

RocketReach: rocketreach.co/trailblazers

Gusto: gusto.com/trailblazers

Quo: Quo.com/trailblazers

Athena: athenago.me/Erica-Wenger

Follow Us!

Mariam Naficy: @mnaficy

Arcade: arcade_ai

@thetrailblazerspod: Instagram, YouTube, TikTok

Erica Wenger: @erica_wenger

This week, we chat with Marlon Nichols!

Marlon is the co-founder and managing general partner of MaC Venture Capital, a leading seed-stage firm backing visionary founders who are redefining industries and shaping the future. Under his leadership, MaC has grown into one of North America’s largest seed-stage venture firms, with over $600 million in assets under management.

He’s backed an incredible portfolio of companies including MongoDB, Gimlet Media, Thrive Market, Blavity, and Pipe—consistently identifying cultural and technological shifts before they hit the mainstream. His ability to spot transformative opportunities has earned him recognition on Business Insider’s Seed 100 and PitchBook’s top VCs to watch.

Before founding MaC Venture Capital, Marlon launched Cross Culture Ventures and served as an investment director at Intel Capital, developing a sharp lens on the intersection of culture, technology, and consumer behavior.

A former professional athlete, Marlon brings a leadership style rooted in discipline and long-term vision, and is deeply committed to expanding access in venture capital through his work with Kauffman Fellows.

✨ This episode is presented by Brex.

Brex: brex.com/trailblazerspod

This episode is supported by RocketReach, Gusto, OpenPhone & Athena.

RocketReach: rocketreach.co/trailblazers

Gusto: gusto.com/trailblazers

Quo: Quo.com/trailblazers

Athena: athenago.me/Erica-Wenger

Follow Us!

Marlon Nichols @MarlonCNichols

MaC Ventures: MaCVentureCap

@thetrailblazerspod: Instagram, YouTube, TikTok

Erica Wenger: @erica_wenger

Timestamps:

0:00 Intro

0:58 The Hardest Part In Justin’s Journey

2:17 Knowing When Something Has To Change

3:57 How Justin’s Wife Helped Build Their $15M Business

5:44 Revenue Sources

8:05 Learning How To Build Work-Life Balance

10:46 How AI Tools Impact Writing

16:40 The Most Valuable Social Platform

24:00 Justin’s Favourite Piece Of Writing

26:35 The Biggest Problem Founders Face Today

30:07 How To Give Value To Your Clients

31:59 Everyone Is So Bombastic

35:08 How Justin Chooses What Businesses To Invest In

39:10 Clients Love Being Part Of A Community

41:29 Building A $15M Business Alone

43:44 Healing From Burnout

48:41 Rapid Fire Questions