In the summer of 2013, Dan Morehead made a bold prediction:

Bitcoin at $65 was a screaming buy. Armed with conviction, he sent an email to his fund with a subject line in all caps: “WE SHOULD BUY BITCOIN NOW AT $65.”

By the weekend, he had personally acquired 30,000 Bitcoin.

This move was a masterclass in asymmetric investing.

Bitcoin represented a unique opportunity—where the potential upside dwarfed the downside risk.

Fast forward to today, his Bitcoin fund has posted a staggering 131,000% return.

But what can the rest of us learn from this story?

How do you find the next asymmetric bet that could deliver life-changing returns? Pulling from insights shared in Dan Morehead’s Bankless podcast appearance, here are the keys to asymmetric investing, whether in crypto or beyond.

What Is Asymmetric Investing?

The concept is simple but powerful: you look for opportunities where the upside far exceeds the downside.

These aren’t “safe” plays.

They’re frontier investments—the kind of trades that seem crazy to most people at the time but offer astronomical potential if they work.

As Morehead explained, investing in Bitcoin back in 2013 was an incredibly contrarian move.

The ecosystem was nascent, riddled with skepticism, and riddled with sketchy logistics.

To buy Bitcoin in bulk, he had to wire millions to Slovenia—risking everything on Bitstamp, a fledgling exchange.

Recognize the Frontier

Asymmetric opportunities usually exist in what Morehead calls the "frontier."

These are areas that feel risky, underdeveloped, or even speculative at first glance. But that’s exactly where outsized gains hide.

Consider other examples from Morehead’s career:

• Investing in Tesla Motors when it was a “wild bet” on electric cars.
• Launching one of the first funds in Saudi Arabia and the UAE, now considered standard emerging markets.
• Betting on Argentine farmland during a financial crisis.

In every case, these bets were considered “weird” at the time but paid off spectacularly.

Pattern Recognition Is Everything

Morehead credits much of his success to seeing patterns emerge across asset classes. Whether it’s commodities, emerging markets, or Bitcoin, asymmetric trades often share similar characteristics:

• They feel uncomfortable. Buying Bitcoin in 2013 meant dealing with clunky exchanges and manual transactions.
• They are misunderstood. Bitcoin was seen as “magic internet money” used by drug dealers on Silk Road. Most people couldn’t imagine it as a legitimate financial asset.
• The upside is exponential. Morehead knew Bitcoin had the potential to grow 1,000x or more because its addressable market—gold, remittance, and payments—was massive.

To develop pattern recognition, Morehead suggests looking at history. What technologies or markets have disrupted the status quo in the past?

Crypto is still early—analogous to investing in the internet in the 1990s or gold in 1000 BC.

What’s Next?

Bitcoin has come a long way since 2013, but Morehead believes the opportunity isn’t over.

He argues that we’re only 15% into global crypto adoption.

 The technology is still maturing, and the potential to disrupt legacy industries—Visa, Mastercard, and even gold—is enormous.

More importantly, the playbook for finding asymmetric opportunities hasn’t changed.

 The next 1,000x investment might not be Bitcoin, but it will have the same hallmarks: discomfort, skepticism, and enormous upside potential.

Bet Big, Bet Small

Asymmetric investing isn’t about risking it all on one trade. It’s about placing smart, calculated bets on the frontier.

As Morehead puts it, “Invest as much as you can afford to lose 80% of—and hold on.”

That’s the formula for finding the next Bitcoin, Tesla, or whatever the future holds.

The frontier is still open.

And 2025 is going to be FULL of these opportunities.

Happy new year,