Trailblazers by Erica Wenger

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