$100 Million Story
Solopreneurship is the future.
Sahil Lavingia, previously the first designer at Pinterest, founded Gumroad in 2011.
He started it at age 19 after realizing how difficult it was for creators to sell digital products directly to consumers, without having to develop a website and complicated funnels.
In 2012, Gumroad raised $8.1 million in funding from prominent investors in the city of startups, San Francisco.
But the vision didn’t pan out. After failing to secure a Series B investment in 2015, Sahil Lavingia decided to rebuild Gumroad as a lean, remote-first business, employing only contractors and part-time workers—no full-time employees, no offices.
In other words, Sahil adopted the solopreneurship model.
He laid off all full-time employees, offering contract-based roles to some, and the company not only survived but became profitable. In 2020, it processed $143.8 million in sales, generated $9.2 million in net revenue, and achieved $1.08 million in net profit.
But the story doesn’t stop there.
As a solopreneur, Sahil couldn’t approach traditional VC investors the way he could as a startup founder. He also said he was tired of dealing with them. In 2021, he launched a crowdfunding campaign to raise growth capital and give the broader community of creators and supporters a chance to invest in the company’s future.
The campaign was a major success. Gumroad hit its $5 million goal within 12 hours, attracting over 7,000 individual investors and valuing the company at $100 million.
In 2023, after switching to a 10% flat fee model, the company reported a $9 million net profit.
So let’s sum up:
A failed startup became a highly successful solopreneur venture.
Sahil Lavingia raised $5 million in growth capital as a solopreneur.
He made $9 million in 2023.
The platform is a preferred place to sell products for other lean entrepreneurs, such as ConvertKit (now Kit) founder Nathan Barry. Its user base continues to grow.
What I want to tell you with this:
The solopreneurship model will become increasingly popular in the future.
The solopreneurship model has huge potential, both in delivering value to users and generating profit.
Solopreneurship isn’t limited to writing online or freelancing. You can be or do anything.
However, solopreneurship has its specifics, and since it’s still relatively new, there aren’t many educational programs that lay the foundation for how to build a solo business.
As a solopreneur for the past 11 years, and someone who has been researching and reporting on the industry for the past 5, I’ve developed such a program.
It’s called The Smarter Solopreneur Strategy, and I’ll be rolling it out to paid subscribers soon.
Stay tuned and remember, you’re early in this solopreneurship movement. It’s literally the future of work.
Till next time,
Maya
It makes a lot of sense, but we need to rethink the model of creating turf and control in favor of building a sustainable business.
Wow, this was such an inspiring read! Sahil Lavingia’s story with Gumroad is incredible — it really shows how failure doesn’t have to be the end. Instead, it can lead to something even better if you’re willing to rethink things and stay scrappy.
I love the idea that solopreneurship isn’t just about freelancing or writing; it’s about creating value in a way that works for you. The fact that Gumread became so profitable after switching to a lean model proves there’s huge potential in doing things differently. And honestly, it makes total sense that creators would flock to a platform built by someone who gets their struggles.
Thanks for sharing this story — it’s such a great reminder that success doesn’t always look like Silicon Valley VC funding. Sometimes, it looks like staying lean, building community, and trusting your vision. Can’t wait to see where this movement goes next!