Sahil Lavingia on Gumroad’s groundbreaking equity crowdfunding raise, lessons from a decade-long startup journey, insights on rolling funds & more | E1188

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Check out Gumroad: https://gumroad.com

FOLLOW Sahil: https://twitter.com/shl
FOLLOW Jason: https://linktr.ee/calacanis

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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:
0:52 Jason intros Sahil Lavingia & they discuss Gumroad’s explosive early days
5:44 Launching one of the first $5M equity crowdfunding rounds, lessons from being on both sides of the table as a founder & investor
10:35 Roman – Get $15 off your first order of ED treatment, a FREE online visit, and FREE two-day shipping at https://www.getroman.com/twist
11:47 Kleiner Perkins’ initial investment in Gumroad, raising millions from top VCs as a teenager
17:22 Receiving a bridge round from KP with aggressive terms, founders raising with poor terms being a negative signal, going into “cockroach mode”
25:32 Dell – Sign up for a free IT consultation at https://launch.co/dell
26:58 Gumroad’s growth resurrection, competing on price, buying out Kleiner Perkins
32:57 How Sahil settled on equity crowdfunding for Gumroad’s recent fundraising
38:07 OurCrowd – Sign up for a free account at https://www.ourcrowd.com/twist
39:42 Getting 7000+ investors, major innovations in general soliciting of rounds, why Sahil only raised at 8.5x revenue, tying brand to capital, NFTs & rights
54:56 Starting a rolling fund, getting anchored by Naval, why 506(c) over 506(b), managing risk and upside
1:06:23 Sahil’s advice from getting through the rough patches with Gumroad

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