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

about this episode

Check out Barstool: https://barstoolsports.com

FOLLOW Dave: https://twitter.com/stoolpresidente
FOLLOW Jason: https://linktr.ee/calacanis

Listen here:
Apple: https://podcasts.apple.com/us/podcast/this-week-in-startups-audio/id315114957
Spotify: https://open.spotify.com/show/6ULQ0ewYf5zmsDgBchlkr9
Overcast: https://overcast.fm/itunes315114957/this-week-in-startups-audio

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

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