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.

Shervin Pishevar doesn't do anything small. While other investors carefully placed $25K bets, Pishevar was writing nine-figure personal checks into nuclear fusion and co-founding Hyperloop. Studying Shervin Pishevar investments isn't about conservative portfolio construction. It's about understanding how conviction in transformative industries generates massive returns.

From Immigrant to Super Angel

Pishevar immigrated to the United States with his family carrying $35. His father worked as a taxi driver and mother as a maid, despite holding advanced degrees in their homeland.

This background shaped everything. Pishevar gravitates toward founders tackling impossible problems because he fundamentally believes in determination and resilience.

The Sherpa Capital Numbers

Pishevar co-founded Sherpa Capital, which managed $650 million across three funds, raised an additional $500 million in co-investments, and pioneered SPVs with over $200 million.

The portfolio: Uber, Airbnb, Slack, Robinhood, SpaceX, Postmates, GoPuff, Warby Parker, Tumblr, and Machine Zone.

Since 2011, Pishevar's early investments generated over $7 billion in value, with more than $3 billion distributed in profits at an 88% IRR.

The Investment Thesis: Regulatory Arbitrage

Sherpa Capital's strategy was "regulatory arbitrage." Pishevar believed that out-of-date rules stifle labor markets, and breaking monopolies unlocks tremendous economic value and job creation.

This explains why Shervin Pishevar investments concentrated in companies fighting established industries. Uber versus taxi medallions. Airbnb versus hotel regulations. These weren't just tech companies, they were movements.

The Uber Story: More Than Just Money

Pishevar's most notable investments include Uber, where he was an early investor and board member. But his involvement went beyond typical investor support. When Uber faced existential threats from regulators, Pishevar publicly advocated for the company.

This level of commitment is rare. Most investors write a check and show up to board meetings. Pishevar treated his portfolio companies like they were his own.

The Massive Personal Bets

Helion Energy: In 2021, Pishevar invested $375 million in Helion's $500 million Series E round, his largest personal investment ever. Microsoft signed an agreement to buy electricity from Helion later this decade.

Hyperloop One: Pishevar co-founded Hyperloop One in 2014. Sherpa Capital led the first investment round, raising $37 million.

These bets reveal Pishevar's appetite for frontier technologies. He's not interested in incremental improvements. He backs companies trying to fundamentally change how the world works.

Pattern Recognition: Finding Founders Early

Pishevar recruited Anthony Casalena at age 15 while at WebOS, supporting him in founding Squarespace. He hired the future founders of Instacart (at 18) and TrueBill (at 21).

He doesn't just invest in trends. He's been instrumental in creating eleven groundbreaking industries, including Hyperloop, On-Demand Economy, Ride-Sharing, Cloud Computing, and Quantum Computing.

The Track Record Speaks

Pishevar had 93 exits across 200+ startups. Notable exits include Parse (acquired by Facebook), Dollar Shave Club ($1B exit), Postmates (acquired by Uber), and Truebill ($1.3B exit to Rocket).

Forbes named him to the Midas List four consecutive years.

Key Lessons For Angel Investors

Have genuine conviction in transformative industries

Don't just follow trends. Develop deep insights into where the world is heading and back companies that will shape that future.

Support your founders aggressively

When portfolio companies face existential threats, don't sit on the sidelines. Pishevar's public support for Uber during regulatory battles demonstrates the value of committed investors.

Consider regulatory arbitrage opportunities

Look for companies solving real problems held back by outdated regulations. These companies can unlock enormous value if they successfully navigate regulatory challenges.

Don't be afraid of frontier technologies

Pishevar's bets on fusion energy and hyperloop transportation show that the biggest returns often come from backing technologies that seem impossible.

Build deep domain expertise

Pishevar spent decades operating companies before becoming an investor. His operational experience made him a more valuable partner to founders.

The Bottom Line

Shervin Pishevar investments represent a masterclass in aggressive, conviction-driven investing. His approach won't work for everyone, especially risk-averse angels or those without deep operational experience. But for investors willing to take concentrated bets on transformative companies and support founders through the hardest battles, Pishevar's track record offers a compelling blueprint.

Ready to invest alongside experienced operators who understand conviction-driven investing? Angel Squad connects you with a community of investors who've been in the trenches, plus access to invest in Hustle Fund's top-performing early-stage startups with checks as small as $1K.