The Crazy Ones
Nov. 15, 2022

What You Need to Know Before Raising Capital, and The Billion-Dollar Media Company You’ve Never Heard of

Episode 7: Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) recount the wild story of how the digital media company Red Ventures bootstrapped its way to becoming a business with an $11 billion valuation. Then, the crew dives into fundraising—when to do it, how to set your goals, and their best advice for how to raise most successfully. And finally, the crew answers a Startup AMA question around how find the most attractive benefits packages at the best rates as a small company.


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00:33 - Intro

02:02 - The Rundown

03:15 - The story of Ric Elias and Red Ventures

08:09 - Ric’s life-changing experience 

08:51 - How Red Ventures’ growth started to take off

12:10 - Red Ventures’ great work culture

13:29 - Jesse’s biggest takeaways from working with Red Ventures

15:38 - How Ric Elias spends his time

24:16 - Sophia’s experience of fundraising and her biggest lessons learned

30:51 - What kind of businesses should raise money vs shouldn’t?

36:29 - Sophia’s advice for founders looking to raise capital right now

37:05 - Jesse’s advice for founders looking to raise capital right now

37:37 - Alex’s advice for founders looking to raise capital right now

37:58 - Startup AMA - How do startups get attractive benefits packages at competitive rates before they get a large headcount?


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