HARJTAGGAR

Born in 1984 or 1985 (he keeps you guessing), Harj Taggar grew up in London with a route that looked suspiciously conventional: University of Oxford, Jurisprudence (that's law, to us normal folk), graduate in 2006, become a lawyer, wear a wig occasionally in court. Simple.

But somewhere between Blackstone's Commentaries and a business idea that wouldn't let him sleep, Harj made a decision that would define his life. He dropped out of law school, bought a plane ticket to San Francisco, and never looked back. His mum probably has mixed feelings about this.

In 2007, alongside his brother Kulveer, he co-founded Auctomatic — a platform for online sellers to manage their marketplace listings. It got into Y Combinator's Winter 2007 batch. By 2008, it was acquired by Live Current Media. Harj Taggar had his first exit before most of his Oxford classmates had passed their bar exams.

That experience left a mark. Not just the money — but the realisation that Y Combinator was something extraordinary. When YC invited him back, not as a founder but as a Partner, he became something genuinely unprecedented: the first non-founder to ever join the YC team. That, in Silicon Valley terms, is the equivalent of being made a cardinal without ever having been a priest.

The joke that ended his legal career. A law firm partner once remarked that their office building "used to be a factory." Harj quipped back, "I guess some things never change!" He was quite proud of the line. The room was not. He spent the rest of that internship trying to figure out what type of humour wasn't taboo in law. He never did find out — because he left.

His blog post on humour quotes John Cleese: "Allow subordinates no humour — it threatens your self-importance." This tells you everything about why Harj and law were never going to work out.

In 2011, while still working as a YC partner, Harj co-founded Initialized Capital with Garry Tan and Alexis Ohanian (yes, the Reddit man). It started as a side project — a scrappy $7 million fund to back YC alumni. One of their very first cheques went to a small company called Coinbase.

The rest, as they say, is history worth approximately $64 billion at the time of Coinbase's direct listing. The Initialized Capital portfolio also includes: Instacart (grocery giant), Rippling (workforce software behemoth), Flexport (logistics tech), Opendoor (real estate), and GOAT (sneakers, obviously). The fund grew from $7M to over $3.2 billion in assets under management. Not bad for a side hustle.

Harj left Initialized in 2014 to pursue his third venture: Triplebyte — a technical hiring platform built on a radical idea: judge engineers on what they can actually do, not where they went to university. There's a certain poetry in an Oxford man who dropped out building a company that ignores credentials entirely.

Triplebyte raised $10M in Series A from — brilliantly — Initialized Capital (his own old fund backing his new startup). It eventually raised $50M+ and was used by household names including Apple, American Express, Adobe, and Dropbox to hire engineers.