Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups

Tony Hsieh died on November 27, 2020, at 46, from complications after a fire in New London, Connecticut. He left behind an estate estimated at $500 million, a downtown that still bears his fingerprints, and a set of ideas about business and investing that were unlike anyone else's.

Most people know him as the CEO of Zappos. Fewer know the full arc of his investing life, and what made Tony Hsieh investments so strange and interesting.

From LinkExchange to Venture Frogs

Before Zappos, Hsieh co-founded LinkExchange with Alfred Lin in 1996. Microsoft acquired it in 1998 for $265 million. Hsieh was 24. Most people would have stopped there and considered themselves done.

Instead, he and Lin used the proceeds to start Venture Frogs, an incubator and investment firm. Their early portfolio included Ask Jeeves and OpenTable. One of the pitches they received in 1999 was from a founder named Nick Swinmurn, who wanted to sell shoes online. Hsieh almost deleted the voicemail. He didn't, and the investment in what became Zappos eventually reshaped his entire life.

It's worth sitting with that for a second. One of the most influential e-commerce companies in the world almost got passed over by its own future CEO because the pitch didn't immediately make sense. Swinmurn's deciding detail was that mail-order catalogs were already the fastest-growing segment of footwear retail. That one data point changed everything.

The Zappos Years and What Came After

Hsieh joined Zappos as CEO in 2000, starting with $1.6 million in sales. By 2009, facing a potential cash crunch, he sold to Amazon for $1.2 billion. He stayed on as CEO for another decade, building Zappos into a case study for company culture done right. His 2010 book, Delivering Happiness, became a New York Times bestseller and influenced a generation of founders thinking about how workplaces actually function.

Then came the project that defined his later years.

The Downtown Las Vegas Bet

In 2009, Hsieh organized what became the Downtown Project, committing $350 million of his own money to revitalize the Fremont Street area of Las Vegas. This wasn't a real estate play. It was a social experiment. He wanted to create a dense, walkable urban neighborhood where tech entrepreneurs, artists, and Zappos employees could live and work together and generate the kind of serendipitous collisions he believed produced innovation.

Eric Bahn of Hustle Fund has written about the idea that the best investments are often about ecosystem, not just individual companies. That's what Hsieh was trying to build in physical space. The Downtown Project funded restaurants, bars, a preschool, tech startups, and a small business development program. It acquired around 90 properties by 2017. For several years it worked well enough that Hsieh became something of a civic figure in Las Vegas.

The project eventually struggled to sustain its original vision. Some of the funded startups didn't survive. The density of collisions Hsieh imagined didn't always materialize the way he'd hoped. But the attempt itself was instructive. He was trying to engineer the conditions for community rather than just back individual companies, which is a fundamentally different theory of what investing is for.

What Angel Squad Members Can Learn from His Approach

Hsieh's most interesting investment insight isn't in any specific company he backed. It's in his belief that the network matters as much as the bet. He joined JetSuite's board in 2011 and led a $7 million round because he believed in the people building it. He invested in downtown Las Vegas because he wanted to be surrounded by builders. The through-line is always about proximity to people doing interesting things.

This is exactly what drives Angel Squad's approach to investing. Members across 50-plus countries aren't just getting deal flow from Hustle Fund GPs like Elizabeth Yin, Eric Bahn, and Shiyan Koh. They're plugging into a community of operators who think about investing the way Hsieh did: as a relational activity, not a transactional one. When you're investing early, the network you're part of shapes your judgment, your access, and your outcomes. Learn more at hustlefund.vc/squad.

The Harder Parts of the Story

Hsieh struggled with loneliness despite building communities. The pandemic years hit him particularly hard. After stepping down as Zappos CEO in August 2020, he relocated to Park City, Utah. He was 46, wealthy beyond most people's imagination, and deeply isolated. He died in a fire in Connecticut later that year. A will, believed signed in 2015, surfaced in 2025 and has been the subject of ongoing legal proceedings.

It's a story worth reckoning with directly. Hsieh's public message was about happiness as a destination, a system, a deliverable. His private life was messier. That doesn't diminish what he built, but it complicates the lesson.

The Takeaway

Hsieh's body of work as an investor is unusual because it doesn't map neatly onto conventional angel investing. He wasn't optimizing for returns above all else. He was investing in theories about how people and communities function. Some of those theories worked. Some didn't. But the seriousness with which he took the question, what are we really building when we invest, is something worth carrying forward.