You Lose Some and Win Some

As long as the outcome is income

Reading time: 3 min

Oh well, guess you lose some and win some

Long as the outcome is income

Drake, Over My Dead Body

Babe Ruth is known as one of the greatest baseball players of all time.

In 1923, he set the record for most home runs in a season. Do you know what else he also set a record for?


He was struck out more than any other player in the league. Most people are afraid to strike out, but not Babe.

He knew you needed to take risks to hit it big, even if that meant taking failures in the process. Every strikeout brought him closer to his next home run.

Some people never attempt anything because they’re worried about failing. But there’s no success without failure.

Before I found writing, I failed at a lot things.

  • I tried learning how to program.

  • I tried photography as a side hustle.

  • I tried DJing for a summer.

  • I tried day trading and lost thousands of dollars in the process.

  • I tried starting a paid community which shut down after a couple of months.

Even with writing, my tweets and threads flopped at first.

I’d get 1 or 2 likes at most. Strikeout after strikeout. But I kept putting myself out there and taking swings. Then it happened.

I hit my first home run.

One of my threads took off, gaining hundreds of likes and a surge of new followers (and massively boosting my ego that day).

After that, I had a formula for what worked and knew I just had to keep taking swings. Several flops came but so did a lot more home runs. Then one day, someone noticed my work and reached out about a web3 content position. Ya boy got his first shot at the big leagues.

I wouldn’t be where I am without all those failures.

Similar to my journey as a writer, I wouldn’t have found investing success without taking losses in the process.

My first time investing?

I struck out badly, losing all my hard-earned savings.

I’ve made several bad investments and poor decisions throughout my investing journey.

Even now, I currently have some NFTs and coins that are down 90% and have no chance of recovering.

Despite all the losses, I’ve managed to build a six-figure investment portfolio. Like Babe Ruth, I wouldn’t have hit home runs without taking strikeouts.

If you want high rewards, you need to take high risks.

No, this doesn’t mean go throw your life savings at random NFTs and coins. You need to take calculated risks. You need to stay in the game to keep taking your shots—and you can’t do that if you lose all your money on your first swing.

Let’s take a look at venture capital (VC) investing.

VC investing often involves investing in several companies with the expectation that most will fail and a few will become highly successful.

For example, if a VC makes 50 investments then they’d expect:

  • More than half will fail.

  • 10 or so will do pretty good.

  • 1 or 2 will go to the moon and far outweigh their losses.

Failure is part of the game. You lose some and you win some. As long as the outcome is income.

I’m not in the VC investing game but I follow the same principles with my own investing.

I expect some of my high-risk investments to fail.

I personally allocate around 1-5% of my portfolio to a single high-risk asset (10% max if I’m hella bullish). That way a loss won’t ruin me, but if it does well then it still pays off.

I also balance my high-risk investments with low-risk investments using a barbell strategy. If my high-risk investments fail then I have something to fall back on. My low-risk investments keep me in the game so I can keep taking swings.

Whether it’s investing or pursuing your passion, you’re going to take Ls in the process.

But all it takes is one win to change your life forever.

Talk next week,

Fifty Sat


I want to do a newsletter edition where I answer the community’s questions. Reply to this email with questions you have about crypto, finance, or anything in general.

I’ll feature and answer some in one of the next newsletters.

Song of the Week

“Somewhere between psychotic and iconic. Somewhere between I want it and I got it.”

GOAT Drake album.

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