Person · 3 items

Sahil Lavingia

Gumroad founder who has published unusually candid accounts of raising and not raising.

Articles (2)

Article

Reflecting on My Failure to Build a Billion-Dollar Company

Sahil Lavingia

Lavingia raised $8M from top VCs at 19, failed to hit venture-scale growth, laid off 75% of his team after a failed Series B, and rebuilt Gumroad as a profitable, deliberately smaller company. A brutally honest account of what happens when you take venture money and land on the 'good but not billion-dollar' outcome.

Failed raiseFundraising psychologySeries A

View item →

Article

Reflecting on My Failure to Build a Billion-Dollar Company, Part 2

Nathan Baschez

An analytical companion to Lavingia's essay: Baschez unpacks the structural reasons venture-backed Gumroad 'failed' at billion-dollar scale while succeeding as a business, examining how funding choices define what counts as success.

Failed raiseValuation & dilutionSeries A

Availability varies

View item →

Threads (1)

Thread

How to Raise a Crowdfunding Round, by the Founder Who Raised $5M in 12 Hours

Sahil Lavingia

Lavingia's post pointing to his 'How to Raise A Crowdfunding Round' guide, drawn from Gumroad's landmark March 2021 Reg CF raise: $5M in 12 hours from 7,303 investors (5,800+ first-time angels) at the newly raised legal cap.

Alternative capitalFundraising strategyStage-agnostic

View item →

Find the investors these stories are aboutVCMatch matches your startup with the VCs most likely to invest at your stage and sector.

Get matched