ALEXIS OHANIAN

Alexis Ohanian's story starts at a Waffle House in Medford, Virginia in 2004. He and his University of Virginia roommate Steve Huffman drove there to brainstorm startup ideas, came up with something that went nowhere, got rejected by Y Combinator, and then got a call back from Paul Graham who said — essentially — 'your idea is bad but you seem smart, pivot.' What they pivoted to was Reddit: a simple link aggregator where users voted content up or down.

They built the first version in three weeks.

Y Combinator funded them with $12,000 in 2005. Eight months later, Condé Nast bought Reddit for somewhere between $10 million and $20 million.

Ohanian was 22. That's the origin story.

Fast and completely improbable.

He stayed at Condé Nast for a few years, hated the corporate structure, left, and spent the next several years doing everything at once: co-founding the travel startup Hipmunk (eventually acquired by Concur), writing a book called 'Without Their Permission,' giving TED talks about internet freedom, and loudly advocating against SOPA — the proposed internet censorship legislation that Reddit helped kill in 2012. That campaign was a genuine turning point in how the internet flexes political muscle.

Ohanian was central to it.

In 2010, he went back to Y Combinator as a part-time partner. In 2014, he rejoined Reddit as executive chairman.

The platform was growing fast and was also, at that point, a mess — content moderation disasters, internal chaos, a very public CEO firing. He eventually stepped down from the board in 2020, explicitly to make way for a Black board member, writing publicly that he was doing so in the wake of the George Floyd protests.

It was a notable move. Not many founders publicly resign their board seats and recommend their own replacement.

Meanwhile, he'd started building what would become his main act: 776 (pronounced 'Seven Seven Six'), his own venture fund launched in 2020. Named after the founding year of ancient Rome — because Ohanian is exactly the kind of person who names his fund after ancient Rome — 776 focuses on early-stage bets across consumer internet, crypto, and emerging tech.

He's been deploying capital aggressively ever since.

Reddit is the big one. Ohanian co-founded it with Steve Huffman in 2005, sold it to Condé Nast for roughly $10–20 million, watched it grow into a $10 billion+ platform, and returned as executive chairman from 2014 to 2020.

Reddit went public on the NYSE in March 2024 at a $6.5 billion valuation — a moment that made a lot of people do the math on what his original stake eventually compounded into.

Hipmunk was his second act post-Reddit: a travel search engine co-founded with Adam Goldstein in 2010 that won design awards, built a loyal user base, and was ultimately acquired by SAP Concur in 2016. It quietly shut down in 2020.

Honestly, not his finest chapter — but it taught him something about the limits of competing in commoditized search markets.

776 is the current main event. Launched in 2020 with an initial $150 million fund, it's a solo GP venture fund — meaning Ohanian runs it without a traditional partnership structure.

The fund uses technology to scale deal sourcing and portfolio support instead of hiring a large team. It has backed over 200 companies including early positions in Dapper Labs, Sorare, and a range of consumer and crypto-native startups.

Fund II raised $500 million in 2022, which is a serious number for a fund that's barely two years old.

His portfolio from his earlier investing days (including time at Y Combinator and Reddit-era angel checks) includes Coinbase, Instacart, and a number of other companies that turned into household names. He was writing checks into Coinbase before most people had heard of Bitcoin.

Ohanian bets on consumer internet the way a surfer reads waves — he's looking for the energy underneath the surface before it becomes obvious. His thesis has consistently been: find the thing that seems niche or weird right now, but has passionate early users who can't imagine life without it.

Reddit itself was exactly that. Coinbase was that.

Dapper Labs (the company behind NBA Top Shot) was that.

He's not a spreadsheet investor. He's not running DCF models.

He's asking: does this thing have a community? Is there something about this product that makes users evangelical?

Does it scratch an itch that doesn't have a good solution yet? That's the filter.

At 776, he's also doing something structurally different: running the fund like a startup rather than a traditional VC partnership. No large partnership meetings where deals die by committee.

He can move fast. He's deliberately built software infrastructure to help portfolio companies with hiring, press, and operations at scale — so the value-add isn't just money, it's the platform.

Think of it like a franchise model: you get the capital plus the toolkit.

He focuses heavily on the founder over the idea. He's said repeatedly that the best founders are the ones who have lived the problem they're solving and are slightly obsessive about it in a way that makes normal people uncomfortable.

He was exactly that founder at Reddit. He looks for himself in other people — which is both a strength and a potential blind spot.

Coinbase. Ohanian got into Coinbase early — before 2015, when it was still considered a niche product for crypto enthusiasts who were mostly dismissed as libertarian weirdos.

When Coinbase went public in April 2021 via direct listing, it opened at around $381 per share, valuing the company at over $85 billion. That's an astronomical return on early-stage capital.

Reddit is the other obvious answer, though it's complicated. He sold the company in 2005 for somewhere between $10 and $20 million — which seemed great at the time and then felt less great as Reddit became one of the most visited websites on the internet.

When Reddit finally IPO'd in March 2024, it debuted at a $6.5 billion valuation. Ohanian retained shares.

How much exactly is private, but it's safe to say the compounding on that original $12,000 YC bet across 19 years is one of the more quietly insane returns in startup history.

Selling Reddit in 2005 at 22 for what turned out to be a fraction of its eventual value isn't exactly a mistake — it's what made sense at the time, and $10–20 million is real money. But watching Condé Nast fail to capitalize on the platform for years while it still grew anyway, and knowing that if they'd stayed independent longer the outcome would have been dramatically different — he's acknowledged that stings.

Hipmunk is the cleaner mistake to examine. He co-founded a genuinely well-designed travel search product, raised serious venture funding, built a loyal user base — and then couldn't crack the distribution problem of competing with Google Flights and Kayak for search traffic.

The acquisition by Concur looked like an exit; it was mostly a landing pad before the product shut down entirely in 2020. That's a real loss for everyone who worked there and everyone who loved the product.

The lesson: great design and a passionate user base don't guarantee survival if you're fighting an impossible customer acquisition cost structure.

Ohanian's philosophy is basically: the internet changes everything, keep betting on it, and back the people who are building the future they actually want to live in rather than the future they think investors want to fund.

He's a vocal believer that the best returns come from the things that look wrong at first. Reddit looked wrong.

A community-run link aggregator with no editorial control? Every media company thought that was insane.

Coinbase looked wrong to a lot of traditional finance people. That pattern — conventional wisdom being wrong about the internet — is the through-line of everything he invests in.

He also believes in the compounding value of community. Not just user growth metrics, but actual human community — the kind that forms around products people genuinely love.

Reddit built one. He invests in companies trying to build one.

He's skeptical of growth-hacked, paid-acquisition-driven businesses that never develop organic loyalty.

On personal finance, he's been direct that he reinvests almost everything back into the fund and into new bets. He doesn't talk about diversifying into index funds or real estate.

His view is essentially: if you have genuine edge in identifying early-stage technology companies, use it. Don't spread yourself thin just for safety.

Ohanian married Serena Williams in November 2017 in New Orleans — a ceremony that, reportedly, had a Beauty and the Beast theme, which is a choice. They have a daughter, Olympia, born in September 2017, a few months before the wedding.

Serena's pregnancy was already public; Ohanian was famously by her side through a very difficult birth in which she suffered serious post-delivery complications and has spoken publicly about how close she came to dying. He's been vocal about that experience as something that changed how he thinks about family leave, healthcare, and the specific risks Black women face in childbirth.

His parents are immigrants — his father Armenag came from Cyprus, his mother Anke from Germany. He's talked about his mother's death from cancer when he was in college as a formative experience that sharpened his sense of urgency about doing something meaningful with his time.

He paid off his father's mortgage after the Reddit sale. He named 776 in part as a nod to his heritage — Rome is the origin, but the Armenian angle matters to him too.

Ohanian attended the University of Virginia, where he studied commerce and history. He was in his final semester when he drove to that Waffle House with Steve Huffman.

He applied to Y Combinator from his dorm room. He graduated in 2005, same year Reddit launched — which means he technically finished school before becoming a tech founder, which is a different timeline than most people assume.

He got into UVA law school, deferred, and never went back.

As an Amazon Associate, Netfigo earns from qualifying purchases. Book links above may be affiliate links.