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Sahil Lavingia of Gumroad - The Future of Flexible Companies (Part 2)

Equity, Dividends, and Building a Platform for Flexible Companies and Work

This is Part 2 of my interview with Sahil Lavingia, founder of Gumroad, author of The Minimalist Entrepreneur, and startup investor.

You can check out Part 1 here.

In this episode, we talk about how equity works at Gumroad, their next product, Flexile, and why Sahil opted out of the unicorn chase. Sahil lays out both practical and philosophical visions for what flexible companies like Gumroad could look like in the future.

Watch on YouTube, listen online, or wherever you get your podcasts.

3 Takeaways from talking to Sahil Lavingia

1. 🍰 Contractors can have equity too

Gumroad employees are all contractors working part-time 20-35 hours/week. While they are paid hourly, they also receive equity yearly based on how many hours they worked.

This lets Gumroad thread the needle between flexibility for contractors while still allowing everyone to share in the upside of the company.

2. 💪 Flexile as the Operating System for Flexible Companies

Flexile (waitlist open) hopes to enable more companies to operate like Gumroad. Flexile is software that lets you manage hourly employees while hopefully allowing for equity sharing, dividends, contracts, and other tools needed to run a company like Gumroad.

Long-term the vision is that Flexile becomes a platform where anyone who wants to work flexibly can find flexible companies. You can bounce between companies, collecting bits of equity, and build credibility within the network.

3. 👁 A Vision for a Flexible Future: Compensation as a Long Term Portfolio

Today, working for startups or a big company means getting compensation now, and a potential lottery ticket for the future. You only work for one company at a time, and you have a lot of eggs in one basket. It has worked well for many but those options usually go to zero.

Sahil thinks this could look different. What if a private company like Gumroad could issue dividends in perpetuity to its equity holding employees? A 5% dividend on your shares forever on a cash flowing business is a much higher probability outcome than a Series A startup IPOing or selling for 9 or 10 figures.

In addition, if you work on the Flexile platform, you can freely work for several Gumroad-like companies at once, building a diversified portfolio of equity in addition to your cash base.

This recessionary environment could be the perfect conditions for non-VC, high probability, profitable companies to grow and start sharing the upside with workers.

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(0:00) Intro

(0:30) Equity at Gumroad

(2:51) Dividends through Flexile

(6:30) Thinking long term with compensation

(9:24) What is Flexile

(11:55) Flexile’s Ideal Customer

(15:29) Innovation in Work

(19:56) Lowering the stakes

(24:50) Work isn’t everything

(26:09) A different way to build companies

(31:45) Building a high probability portfolio

(34:28) Opting out of Unicorn Chasing

(37:35) Impact and What People Aren’t Doing

(43:10) The Bleeding Edge