Episode 1153

E1153: Dave Portnoy on the business of Barstool, talent acquisition, Call Her Daddy feud & more

Dec 15, 20201:06:15Watch on YouTube

Check out Barstool: https://barstoolsports.com

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Overcast: https://overcast.fm/itunes315114957/this-week-in-startups-audio

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Show notes:

0:00 Start

0:57 Jason intros Barstool Sports Founder Dave Portnoy; Barstool’s origin as a gambling newspaper & creating the blog, Dave’s first bet & introduction to gambling

6:18 Barstool’s transition into a digital media brand, why Dave disregards resumes, how he looks at hiring

10:17 Masterworks - Skip the 25,000 person waitlist by going to https://www.masterworks.io and using promo code TWIST

11:56 Call Her Daddy controversy

18:56 Dave’s willingness to go down with the ship

22:11 Raising money from Peter Chernin’s Chernin Group

23:45 Squarespace - Go to https://squarespace.com/twist for a free trial, and use code TWIST for 10% off

25:15 Positioning Barstool to capitalize on sports betting, benefits to staying afloat as a company

28:28 Improper framing of Barstool

32:30 Interviewing Trump, day trading at DDTG, taking over financial media

38:54 Gusto - Get three months free when you run your first payroll at https://www.gusto.com/twist

40:16 Will we see Barstool Finance in the future? Creating content for vices

43:06 Unions, Barstool’s advantage in talent acquisition

50:38 The Penn deal, emotional wave of the stock price, post-COVID outlook & getting the virus

56:40 Dave’s next chapter, being shopped to other gambling companies pre-Penn, how 9 figures in wealth impacted his bet sizing, impact of fame