Uploaded August 2021 | Updated September 2026, 2 hours ago

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Welcome to The Quest Season 2: Episode 27 with Alexis Ohanian: the Reddit co-founder and ‘Mayor of the Internet’ shares Reddit’s painful history, growing into a parent, and learning resilience.

I’ve known Alexis Ohanian for almost fifteen years, ever since we were in the trenches together as part of the first Y-Combinator cohort. I witnessed the trials and tribulations he went through while building Reddit first-hand, and watched him grow into a great founder, leader, investor, and parent.

In this episode, he opens up about his personal struggles during the early days of Reddit, the challenges of modern parenthood, and the philosophy behind Seven Seven Six. I really appreciate Alexis for being so vulnerable in this episode, and I think it is a powerful message that all founders need to hear.

0:00 Intro
1:03 Seven Seven Six and investing
10:14 Y-Combinator days: self-doubt and privilege
17:49 Coping with depression and mom’s cancer (Reddit)
23:51 Happiness, wealth and motivation
34:50 Business dads and paid family leaves for men
43:23 Investing in crypto and gaming
50:52 Justin.tv and Reddit days

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