Sahil Lavingia
Born 1992 · Age 33
Founder & CEO of Gumroad; early Pinterest engineer/designer; author of The Minimalist Entrepreneur; early-stage investor and rolling-fund manager. Known for running Gumroad as a lean, largely-contract-based, profitable creator-economy platform.
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Life & Career Timeline
Family moves from U.S. to Singapore
Sahil's family moved abroad (from Long Island) when he was about five; he primarily grew up in Singapore.
Began building iPhone apps and learning design
Started creating apps and learning design in high school, which laid the technical/founder groundwork.
Joins Pinterest as an early employee / designer
Recruited to work at Pinterest (helped build the iPhone app); one of the company's earliest employees.
Moves back to U.S.; enrolls at USC
Moved back to the United States to attend the University of Southern California for computer science.
Drops out of USC after ~4 months
Left USC after a short time to pursue opportunities in Silicon Valley.
Seed funding raised (~$1.1M)
Raised ~$1.1M in seed funding from angels and early investors (Accel, Chris Sacca, Max Levchin, Naval Ravikant among others).
Leaves Pinterest to found Gumroad
Departed Pinterest after about a year to focus full-time on an idea that became Gumroad, a direct-to-audience commerce tool for creators.
Forms LLC and accepts first angel check
Created an LLC (LegalZoom) and accepted an early $10,000 from Craig Shapiro / Collaborative Fund after Hacker News visibility.
Series A led by Kleiner Perkins (~$7M)
Raised a reported $7M Series A (Kleiner Perkins lead), rapidly scaling the young startup's runway and expectations.
Total venture funding exceeds $10M
Across seed and subsequent rounds/bridges the company raised a little over $10M in the early years.
Rapid early growth (10x in first year)
Gumroad experienced a period of extremely fast growth early on (a reported tenfold year), validating product-market fit among creators.
Interview with The Billfold
Profiled in a Billfold feature about leaving college to join Pinterest and then founding Gumroad.
Growth slows; investor pressure increases
Gumroad's growth slowed from earlier highs and investors began to demand aggressive monthly growth (e.g., ~20% MoM expectations).
Major downsizing and pivot to sustainability
Faced with investor pressure and limited runway, Lavingia laid off over half the company, pivoted toward profitability, cut the office, and shifted to contractors.
Received acquisition offer (~$1M)
At one point Gumroad received an acquisition offer for roughly $1M, which would have been insufficient to cover investor preference stack.
Moves to Provo, Utah; pursues painting and writing
Left San Francisco, moved to Provo, studied writing (notably with Brandon Sanderson) and painting; embraced a quieter life while running Gumroad remotely.
Achieves profitability after restructuring
After reducing headcount and operating costs, Gumroad reached profitability and sustained operations as a smaller business.
Kleiner writes off investment; sells shares back for $1
Kleiner Perkins reportedly sold its shares back to Lavingia for $1, effectively writing off its prior investment and dramatically reducing the preference stack burden.
Publishes 'From Bubble to Bubble' reflection
Wrote a reflective essay ('From Bubble to Bubble') describing the experience of scaling, investor pressure, and pivoting Gumroad to sustainability.
Public advocacy for flexible / remote work
Publicly championed remote and flexible work arrangements for engineers and creators (tweets, essays), positioning Gumroad as a flexible employer.
COVID-era growth spike (doubling)
During COVID-era changes to the economy, Gumroad saw accelerated growth — roughly doubling usage/revenue in 2020.
Writes 'Reflecting on my failure to build a billion-dollar company'
Published a widely-read piece reflecting on Gumroad's journey, choices on VC, growth, and prioritizing sustainability over 'growth at all costs.'
Crowdfund round raises ~$5M from non-accredited investors
Leveraging new SEC rules, Gumroad raised ~$5M via crowdfunding (non-accredited investors) — reported as 5% of the company — and approx. $6M total in the round at a $100M valuation.
Raised ~$6M at ~$100M valuation (crowd + other)
Reported that the company raised a ~$6M round at roughly a $100M valuation (including the $5M crowdfunding portion).
Large creator economics metrics reported (GMV & revenue)
Reported metrics for Gumroad: ~$200M GMV for creators and roughly $12M in revenue off that GMV (figures cited publicly around this period).
Announces plan to explore dividends for investors
Publicly discussed exploring issuing the company's first dividend to investors — a sign of long-term sustainable focus versus exit-only thinking.
Launches rolling fund to invest in startups
Launched a rolling fund to invest in early-stage startups (initially reported at ~$5M/year capacity), later scaled.
Reports ~$12M ARR and continued profitability
Public statements cite Gumroad doing ~$12M ARR and being profitable, with a small and mostly contract-based workforce.
Guest on Manifold podcast (episode published)
Appeared on Manifold podcast (Jan 5, 2023) discussing Gumroad, founding story, fundraising, and creator economy ideas.
Rolling fund scaled to larger annual allocation (~$12M/year)
Rolling fund capacity reported to have grown (from $5M/year at launch to ~$12M/year), increasing Lavingia's activity as an investor.
Public speaker — Business of Software (BoS) content & talk
Featured in Business of Software content / talk ('The Pros and Cons of Setting Your Own Goals') discussing Gumroad culture (no full-time staff, no meetings), fundraising, and philosophy.
Continued public thought leadership and writing
Active as a writer, podcaster guest, and public commentator on creator economy, founder culture, remote work, and startup design.
Favikon influencer profile & social-media metrics published
Favikon published a profile (Apr 23, 2025) summarizing Sahil's large X following (~361.9K), YouTube / LinkedIn presence, and influence rankings.
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