Going from Venture-Backed Rocket Ship to Independent Business with Sahil Lavingia of Gumroad

Sahil Lavingia will be speaking at BoS Conf Spring.Online 26-27 April on the topic: “The Pros and Cons of Setting Your Own Goals as an Entrepreneur.”

Venture-backed or independent? That’s a question many founders and entrepreneurs have to answer when they start a software company. (And a highly charged topic for many.)

Sahil is one of the few entrepreneurs who’s gone down both paths, with the same company. After taking angel and venture funding for his company he radically rethought the goals and purpose of his company and pivoted back to an independent business.

We’re therefore delighted to welcome Sahil, founder and CEO of Gumroad, as a first-time BoS speaker to share his unique experiences with us.

Photo courtesy of Sahil Lavingia

The Ultimate Pivot

Founded in 2011, Gumroad first took angel funding and subsequently raised a Series A from names including Max Levchin and Kleiner Perkins. The goal was to scale, grow rapidly, and become a unicorn business.

In 2016, having failed to raise further funding, the company moved from 25 employees to one and Sahil radically rethought the purpose of his company and personal goals.

Since then, the revenue generated by creators on the platform have grown to over $10 million per month and while there are 25 or so people working with the company, none are full time.

The company does not hold meetings or set deadlines.

What you will learn

Sahil will talk about The Pros and Cons of Setting Your Own Goals as an Entrepreneur.

He will discuss the evolution of his journey from running venture-backed rocket ship to owning an independent business.

Having chosen a goal and path for his business that breaks the traditional high-growth mould, he’ll share some of the lessons he’s learned about running a profitable, growing business with no full time employees as well as some of the advantages and disadvantages that come from being different.

Who is Sahil Lavingia?

Sahil was the second employee at Pinterest but left before his stock vested to start Gumroad, an online platform that helps creators sell products directly to consumers.

Learn how great companies are run

At BoS we run events and publish content that is highly valued by anyone trying to build, run, and scale a great software company.

Sign up for a regular dose of actionable and useful content: