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





about this episode

Check out Gumroad:


Listen here:

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
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
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
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

Subscribe to our YouTube to watch all full episodes:

Subscribe to TWiST Clips for all the best moments:

more episodes

See more in: 2021, community, e-commerce, fund raising, investing, Startups
Notice: Only variables should be passed by reference in /home/thiswee/public_html/wp-content/themes/supersimple/functions.php on line 92

Notice: Only variables should be assigned by reference in /home/thiswee/public_html/wp-content/themes/supersimple/functions.php on line 92
| Comments

Leave a Reply

Your email address will not be published.