Navigating the Shift from Entrepreneur to Investor

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Tinder Founder on How Swiping Changed Dating Forever | Justin Mateen

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CHAPTER

Navigating the Shift from Entrepreneur to Investor

This chapter explores the transition from entrepreneurship to becoming a full-time investor and hedge fund manager. The speakers share their journey, emphasizing the enjoyment of working with founders and the importance of balancing work with personal life.

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Justin Mateen set out to make dating simple—no lengthy profiles, no uncertainty—just a "yes" or "no" swipe. Today, Tinder’s user base has expanded to 75 million monthly active users.

Justin Mateen has continued building on his success by investing early in promising startups such as Brex, Curative Health, Deel, Home Chef, Kalshi, Speak, Whop, and many others, becoming a billionaire along the way.

In 2020 he launched JAM Fund, one of the largest Solo VC firms in the world, which has raised approximately $500 million, with $330 million dedicated to its second fund.

Business Insider listed Justin Mateen as the number 1 ranked investor in the “Top 100 list of US seed investors” in both 2020 and 2021, with Forbes including Mateen on their list of the decade's top 10 tech entrepreneurs.

In this episode, he and I sat down to discuss Tinder’s highs, struggles, and the lessons learned along the way. We also unpack:

• the evolution of the 'swipe left/right' phenomenon

• whether Facebook played to his subconscious while building Tinder, and why

• putting all your eggs in one basket → asymmetric returns

Justin’s investing firm, Jam Fund, raised about $300 million from investors for its second fund last year.

ABOUT US:

We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count.

I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. Onward and upward, together.

Connect with us here:

1. Justin Mateen- https://x.com/Justin_Mateen

2. Brex- https://x.com/brexHQ

3. Henrique Dubugras- https://x.com/hdubugras

(00:00:00) Intro

(00:01:37) Inquisitive childhood

(00:05:07) Learning on both fronts

(00:10:08) Bullied and trading stocks

(00:12:36) Relationship with money

(00:15:26) USC and the freshman experience

(00:20:47) Lover boy

(00:23:47) Financial stability and freedom