How I Lost 80% of My Bets and Still Made $21,000

When I was deep into sports betting, I lost 4 out of every 5 bets I placed.
And still walked away with over $21,000 in profit.

That experience taught me more about decision-making under uncertainty than any textbook ever could.

The Counterintuitive Truth About Risk

Most people think smart decisions mean being right most of the time. And that’s what we learn in school, because questions on a test are typically weighted the same.

But here’s what I learned from sports betting:

You can make the right choice and still get the wrong outcome.

Winning life isn’t about being right more often. It’s about playing the game well over time.

That comes down to three principles:

1. Expected Value (EV) – Is the outcome favorable when you account for risk?

2. Position Sizing – How much risk can you handle?

3. Long-Term Thinking – Judge outcomes over years, not moments

How Expected Value Actually Works

A lot of people hear “expected value” and assume it's complicated.

But it’s actually simple once you understand the formula:

EV = (Probability of Winning × Potential Gain) − (Probability of Losing × Potential Loss)

This equation helps you answer one key question:
Is the upside worth the risk?

For example:

You have a 20% chance to make $1,000 and an 80% chance to lose $100.

EV = (0.2 × $1,000) − (0.8 × $100) = $200 - $80 = $120

Even though you lose four times out of five, it’s still a smart bet.
Why? Because the math is in your favor.

If you made the same bet 1,000 times or even 1 million times, you’d come out way ahead.

That shift (focusing on the quality of the decision, not just the result) is a game changer.

How This Played Out in My Life

→ Ethereum in 2016
Bought at $130. Didn’t know it would hit $4,000, but the upside was massive compared to the downside. Small bet (~$300), huge potential.

Fun fact: Selling this Ethereum paid for my housing my junior year of college

→ Moving to Houston
Took a lower-paying job with higher growth potential. It looked like a step back short-term, but it put me on a better trajectory and helped me develop more (higher-paying) skills.

→ First Rental Property
Only bought once I could afford the worst-case scenario (vacancy, repairs, downturn). The cash flow made sense, even if appreciation didn’t happen.

→ COVID Crypto Crash
Ethereum dropped to $118. Panic everywhere. But the fundamentals hadn’t changed, and the expected value was obvious. When people are panicking, there are usually a lot of good bets to be made.

Pattern across all of them?

Good process + right-sized bet + long-term mindset = smart risk

Use This Framework for Any Big Decision

Before you make your next move ask yourself:

1. What’s the worst-case scenario, and can I handle it?
   In modern America, things don’t get that bad. Just give yourself the chance to be wrong several times. If your process is good, you’ll eventually hit.

2. What’s the expected value over 3–5 years (or even 20, 30, or 40 years)?
   There’s no crystal ball. Just favorable odds repeated over a long enough time horizon.

3. Am I prepared to look wrong in the short term?
   Most good bets look bad before they look smart. If you don’t believe me, read The Big Short or watch the GameStop Saga. Playing the odds when no one believes you is hard.

The Biggest Risk of All

The real danger isn’t making a bad bet.
It’s never betting at all.

Trying to “play it safe” often means missing out while inflation eats away your savings or asking yourself “what if” as life experiences pass you by.

You don’t need to be right every time.
You just need to be right about the big things and wrong in small, survivable ways.

What Calculated Risk Are You Avoiding?

A new job?
An investment?
A business idea?

Hit reply and tell me.
Sometimes talking it out with someone else makes the next step obvious.

— Jake

P.S. I still track my investments the same way I tracked my bets: by process, not outcome.
A good decision that goes “wrong” is still a good decision if the math and logic were sound.

P.P.S. If you have a friend making a big decision, send this to them.