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.

Tim Ferriss isn't your typical angel investor. He's the guy who wrote a book about working less, then somehow built a portfolio that includes Uber, Shopify, Facebook, and Twitter. But here's what most people miss about Tim Ferriss investments: it's not about luck or connections. It's about having a system and sticking to it.

Who Is Tim Ferriss, Really?

Before we dig into his portfolio, let's get the basics straight. Ferriss launched The 4-Hour Workweek in 2007 and it became a massive hit. But around the same time, he started writing small checks into startups. We're talking $10,000 to $25,000 investments. Nothing crazy.

His portfolio includes Shopify (as first advisor), Facebook, Twitter, Uber (pre-seed round advisor), Duolingo (Series A), and SpaceX. His $25,000 investment in Uber when it was valued at $3.7 million is now worth millions.

But here's the thing: most of his startups have gone to zero, and that's an expected part of the game.

The Ferriss Investment System (That Actually Works)

Some angel investors fail because they invest too emotionally. They meet a charismatic founder, hear a great pitch, and write a check.

Ferriss does the opposite. He built a disciplined process:

1. Only invest what you can lose

Ferriss treats startup investing like casino money. You shouldn't invest anything you're not comfortable kissing goodbye. This mindset prevents you from making desperate decisions when companies struggle.

2. Build a portfolio, not a single bet

If you're going to invest in startups despite the high risk, plan on building a portfolio of dozens, very slowly and carefully. By 2020, Ferriss had invested in 50+ companies. This portfolio approach increases your odds that a few winners offset the losers.

3. Plan your exits before you invest

Too many angels think they're done once they write the check. Ferriss knows that's only half the battle. Before investing, he creates rules for when he'll double down and when he'll exit (if possible).

4. Test your strategy with "paper trading"

Before putting real money at risk, Ferriss recommends testing your investment thesis with virtual money for about two years. This helps you identify blind spots before they cost you actual dollars.

What Ferriss Actually Looks For

Studying Tim Ferriss investments reveals clear patterns:

Consumer internet companies with network effects

Think Uber, TaskRabbit, Twitter. These businesses get better as more people use them, creating natural moats.

Companies where he can add real value

Ferriss generally invests $10-25K in young, emerging companies with a focus on early stage consumer internet startups. He seeks to advise his portfolio companies on marketing and PR strategies and assists them on improving conversions/sign-ups.

Founders solving problems he understands

Ferriss was often the ideal customer for companies he invested in. He used Uber before investing. He was an Evernote power user. He understood the pain points because he experienced them.

Why Ferriss Mostly Quit Angel Investing

Here's where it gets interesting. In 2015, Ferriss declared a long vacation from new investing, citing the stress of the work and feeling his impact was "minimal in the long run".

In 2023, Ferriss reflected that he started angel investing seriously in 2008 and hit a golden window of converging trends, cheap valuations, and an uncrowded playing field. He doesn't believe he could replicate what he did in 2008-2012 now.

This matters. Even successful investors recognize when the game has changed.

The Real Lessons For Early-Stage Investors

Build your system first

Ferriss says if you want to play in early-stage tech investing, ensure you have a plan for developing an enormous informational advantage. Aim to develop new skills and relationships through portfolio companies.

Start small and learn

Though Ferriss's angel investing snowballed, he began with $10K checks and advising for sweat equity. Think of this as tuition for a real-world MBA.

Timing matters (and you can't control it)

Ferriss acknowledges luck and timing. The financial crisis had culled the herd of investors and fair-weather founders. It was a target-rich environment. Micro-VCs were just starting, and big players hadn't started assailing the seed stage.

Know when to focus elsewhere

Ferriss has largely stepped back from angel investing to double down on writing and his podcast. He finds that creative work brings in forecastable revenue year after year, which has compounded more reliably than all-or-nothing bets.

The Bottom Line

Tim Ferriss investments aren't about mystically picking winners. It's about process, discipline, and treating angel investing like a long-term game where most bets fail but a few winners make it worthwhile.

The most important lesson? Don't invest like it's a hobby. If you're going to do this, build systems, be honest about whether you can add value, and accept that timing and luck play bigger roles than most people admit.

Want to learn from a community of operators who've made the transition to angel investing? Angel Squad brings together experienced investors who share tactical insights on building portfolios, evaluating deals, and adding value beyond just writing checks. Join us to invest alongside seasoned angels in Hustle Fund's top-performing early-stage startups.