Reflecting on My Failure to Build a Billion-Dollar Company
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.
We're Raising $3.5m in Funding: Here is the Valuation, Term Sheet and Why We're Doing It
Buffer publishes every detail of its $3.5M Series A: the valuation, the actual term sheet, investor list, ARR ($4.6M), and the unusual structure that let founders and early employees take secondary money. A landmark in fundraising transparency.
SparkToro Raised a Very Unusual Round of Funding & We're Open-Sourcing Our Docs
After his bruising VC experience at Moz, Fishkin raised $1.3M from 35 angels under a novel structure allowing profit-sharing distributions instead of requiring a huge exit, and open-sourced the legal docs so others could copy it.
Debt is Coming
Danco argues that recurring-revenue businesses funding predictable growth with dilutive equity is a historical accident, and predicts the rise of revenue-based and debt financing for startups. Sparked a wide industry debate.
SparkToro Year 3 Retrospective: Investor Payback, Systemic Challenges, and V2 on the Way
Three years after the unusual angel round, Fishkin reports real numbers: profit-sharing distributions actually paid to investors, growth against plan, and honest assessment of the model's tradeoffs.
Overdosing on VC: Lessons from 71 IPOs
A seed VC analyzes 71 tech IPOs and finds no correlation between capital raised and outcome quality: the most efficient companies returned more per dollar than the most funded. Argues overcapitalization is a drug with real side effects.
Financing Options for Startups (MBA Mondays)
The index post for Wilson's MBA Mondays series covering every startup financing option: friends and family, angels, convertible debt, venture debt, preferred rounds, and when each fits.
Reflecting on My Failure to Build a Billion-Dollar Company, Part 2
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.
The growing dissonance between two business models (SaaS and VC)
A SaaS-focused VC admits the venture model's power-law needs are increasingly mismatched with how most healthy SaaS companies actually grow, and explores what that means for founders choosing capital.
Getting Out of the Startup Rat Race
After raising a $500K seed and then nearly running out of money, Pigford describes negotiating with his investors to reset expectations and step off the venture growth track, with the actual numbers Baremetrics published all along.