March 13, 2024

🥛 Crypto Taxes 101 📖

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GM. This is Milk Road. We present crypto news like a gourmet meal – a feast for your mind, no reservation required.

Here’s what we’re serving up today:

  • Your guide to crypto taxes 📖

  • Crypto is full of ‘Infinite Regret”… 👀

  • Ethereum’s big upgrade was a success 🍪


Every year, we all have to play a game. It’s called Guess-Your-Taxes™

The opponent in this game is the Internal Revenue Service (IRS).

It goes a little something like this:

It’s bullsh*t. I know 🤬

To make matters worse… crypto makes Guess-Your-Taxes even harder

We decided to hit up some smart crypto friends to see what they were doing. They all said the same thing…use crypto tax software. 

So we took a trip up Figure It Out Mountain™️ to find out everything we could.

We tried out different tools like Awaken, CoinTracker, and more. Each one was put under the Milk Road Stress Test to see how well they tracked data. 

We did different things with crypto like: 

  • Buy it

  • Stake it

  • Bridge it

It was the real-life ‘Bop It’ game (the real ones know).

Then we created a guide and ranked each tool based on our experience. Think of it like your cheat sheet for the annual tax pop quiz.

For all my fellow Olympic-gold-medal-procrastinators who haven’t filed taxes yet… check the guide, study it, and bookmark it.

It just might save you a few headaches this year. 

For all of you who have filed taxes… Kudos! Don’t get too comfy though. Next year’s tax season will come knocking before you know it. 

So check out the guide, study it, and bookmark it anyway.

Your future self will thank you.


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Yesterday we took a stroll down memory lane.

We visited the Milk Road “Wisdom Warehouse”. It’s a bank of old tweets, blogs, videos, and explainers we’ve saved over the years.

Only the best of the best. And while dusting off the cobwebs, we found a hidden gem from 2022.

It’s called ‘Infinite Regret’ and is written by Zeneca, an NFT trader. 

Here are the 5 biggest takeaways:

1/ Crypto is full of ‘Infinite Regret’

Did you buy a token that ended up being a scam? Regret. 

Did you sell too early and miss the pump? Regret. 

Did you sell too late and end up round-tripping your profits? Regret. 

Did you miss out on an airdrop worth thousands because you were too busy using the 24837438 other protocols that exist? Regret. 

Were you asleep while a new token did a 100x? Regret.

Crypto is FULL of Infinite Regret.

It’s the only industry where investors can get a 50x return, and still be mad. And while we all think we’ll have no regrets (like this guy)…

… the reality is, you’ll probably feel regret at some point in your crypto career. 

But here’s why that’s a good thing…

2/ Infinite Regret = Infinite Opportunities

Yes, it sucks seeing everyone (but you) hit 100x returns. You might even start thinking that you’re allergic to profits. 

But the fact that these insane money-making opportunities even exist is a very, very good thing…

It means you’re roughly in the right place, at roughly the right time. 

3/ Crypto investing is a numbers game 

There’s a TON of luck involved in this game. Anyone that says otherwise is a damn liar.

But there’s also a lot of skill too.

This includes your ability to research projects, evaluate them (i.e. know what’s likely to succeed and what isn’t), and then place bets accordingly. 

^^ This is what you need to focus on improving. 

And after a while, you realize it’s all a numbers game. The more educated guesses you make, the more the odds will slant in your favor. 

This still does not guarantee success, but it guarantees a better chance of success.

4/ You will lose money sometimes

This is the cost of tuition for crypto college. 

But here’s the thing. The goal isn’t to be happy when you make money and upset when you lose money. (Sounds counterintuitive, I know).

The goal is to:

  • Be happy when you play well (i.e. did good research, found a hidden gem, etc.)

  • Be upset when you play poorly (i.e. FOMO invest, fall for a scam, etc.)  

5/ In order to thrive, you need to survive

If you go all in on a couple of projects that turn to dust, not only do you lose your money, but you also lose your chance at future opportunities.

It’s a double whammy. 

So don’t feel the need to FOMO into whatever hot project your favorite neighborhood influencer is talking about. 

There are no shortages of opportunities (not anytime soon at least), so don’t let the Infinite Regret consume you.

Take your time to really learn and understand the space. 

As they say – we’re all gonna make it.


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Ethereum’s ‘Dencun’ upgrade went live on the main network this morning. History has been made! (Btw – if you want to dive deeper into the upgrade, here you go).

Coinbase is planning to raise $1B in convertible notes. The crypto exchange will use the money for “general corporate purposes” and may also use it to “make investments in and acquisitions of other companies, products, or technologies.”

Grayscale applied to launch a new “mini” Bitcoin trust. If approved, it will be a spin-off of Grayscale’s existing GBTC fund, with lower fees. 

Goldman Sachs, BNY Mellon, and Cboe Global Markets are testing a blockchain-based, communication system called Canton Network. According to the report, they executed 350+ simulated transactions using tokenized assets, digital cash, securities lending, and more.

El Salvador is sitting on $84M profit from its BTC holdings🎵 Stand on my money, headbutt Yao Ming 🎵





DISCLAIMER: None of this is financial advice. This newsletter is strictly educational and is not investment advice or a solicitation to buy or sell any assets or to make any financial decisions. Please be careful and do your own research.