Avenging Angel — Dartmouth Alumni Magazine (2014)
Source: raw/articles/avenging-angel.md | Dartmouth Alumni Magazine
Bibliographic Details
- Author: Eric Smillie ‘02
- Publication: Dartmouth Alumni Magazine
- Issue: November–December 2014
- URL: https://dartmouthalumnimagazine.com/articles/avenging-angel
Summary
The best single long-form profile of Naval Ravikant written at the peak of AngelList’s early growth. It narrates the arc from Epinions betrayal to AngelList reinvention, with direct quotes throughout.
Background: Queens to Dartmouth
Born in India, Naval arrived in Queens at 9 with his single mother and older brother Kamal. A self-described antisocial introvert, he was drawn to Phi Tau (“the geek and misfit house”) at Dartmouth. He was accepted to Stuyvesant, which put him on a college track, and chose Dartmouth partly for its high satisfaction ratings and financial aid. He majored in economics and computer science — “the only flexible combination” — and bought his first Mac with a student loan.
Epinions and the Lawsuit
Ravikant co-founded Epinions in 1999 (consumer reviews), which raised 750M. Ravikant and three co-founders received nothing; they sued Benchmark Capital, August Capital, and a co-founder, alleging a conspiracy to hide the company’s value and devalue their common stock. The lawsuit settled for an undisclosed amount and branded him “radioactive mud.” “The day I realised what had happened was horrific,” he told Smillie. Rather than start another company, he became an angel investor — learning from the lawsuit that he hadn’t understood what he was getting into.
Venture Hacks → AngelList
The experience turned Ravikant and Babak Nivi into educators — they wrote Venture Hacks, advising entrepreneurs on term sheets and fundraising. This kept them connected to an ever-widening network of investors, which became the seed of AngelList (launched 2010). By early September 2014, over 100,000 companies had raised more than 10–20M per month. Syndicates — allowing a prominent angel to pool co-investors deal-by-deal — amplified individual leverage: Tim Ferriss described having “$3–4M in automatic backing” and funding his last three deals in two to three hours each.
The JOBS Act: Six Months in Washington
AngelList’s original structure ran afoul of broker-dealer regulations. Ravikant spent six months lobbying Congress to carve out an exemption — a gruelling, tedious process. The Jumpstart Our Business Startups (JOBS) Act passed in 2012, signed by President Obama, and included the AngelList exemption. “How could a congressperson vote against something called the JOBS Act?” Ferriss and Tom Fallows (Google) both describe Naval as a “business chess master” who sees angles others miss.
Philosophy of Radical Transparency
AngelList is described as injecting the transparency of stock markets into the previously opaque, relationship-driven VC market. Where previously raising money could take 2 months of cold pitching, AngelList can cut that to hours. Ravikant frames this as a service business — not being the dealmaker, but making other people’s deals smooth.
Key Concepts Introduced / Reinforced
angel-investing · angellist · startup-ecosystem (implied) · babak-nivi · wealth-creation
Connected sources: wikipedia-2025-naval-ravikant (factual corroboration) · stankovic-2021-naval-ravikant-profile (extends AngelList history)