Sahil Lavingia on Gumroad's groundbreaking equity crowdfunding, rolling funds & more | E1188

Jason Calacanis chats with Sahil Lavingia about Gumroad's early days, their first $5M equity crowdfunding round, and the lessons learned as a founder and investor. They also discuss Gumroad's growth resurrection, the decision to use equity crowdfunding for recent fundraising, and Sahil's advice for navigating business challenges.

Speakers

AI Chat

Unidentified

Jason Calacanis

Host • 56%

Sahil Lavingia

Guest • 43%

Chapters

0:00	Start
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
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
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
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

Transcript

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