A Letter For Jesse Itzler

When the signals converge and someone says it for you

I’m writing today from my bed, laid up sick with the flu and feeling increasingly worse. So I’m writing this ahead of time so I can schedule the post and go back to bed.

Something magical typically happens to me in these moments, when I’m sick and isolated, my brain tends to find it’s way to these signals that all start to converge. Often times these signals have long tails and are meandering until they aren’t anymore, they converge and then BOOM, they coalesce together.

This happened last night when I watched the latest episode of My First Million, hosted by the venerable duo of Shaan Puri and Sam Parr. I’ve been a fan of these two and their work for many years now, they produce just outstanding content.

Their guest was Jesse Itzler, hustler extraordinaire and “do hard things” junky.

The premise of the show was Jesse’s way to prepare for an awesome 2025 and right up front he starts to talk about writing letters !

He tells the guys:

“ [at the end of the year] I write handwritten letters to the 20-30 people that really impacted me or helped me… with no purpose other than really giving a thank you”

I wasn’t expecting the premise of my project to be communicated out by Jesse in such a succinct and beautiful way. It was like gasoline on a fire.

He ends up talking about his habit of writing letters for 6 straight minutes. From how he used letters to do marketing in his first business and writing over 3000 letters to keeping all the handwritten letters he gets throughout the year.

Shaan even jumps in and gives a story about another guest they had on that got a letter from Warren Buffett. Then Jesse hits back with an anecdote about getting a letter every year from Coach K (of Duke Basketball Fame).

If you’re keeping score, that’s 2 Billionaires, one of which is the single greatest investor of all time, along one of the greatest coaches ever, that regularly write letters to tell people thank you.

Sometimes it’s nice to get validation that your idea is good. It’s not like this project is some secret future vision either, it’s an old idea. I’m just making it very public and am making it my mission to get others on board start this practice and then keep doing it. It works.

Jesse even hits on why it works - A letter has soul, and you can’t outsource soul. Giving gratitude and soul to another human is a gift.

I’ll end this with the same plea that Jesse gives, go write some letters to people that have made an impact on you and who you’re thankful for. Set aside 30 minutes, write 10 names down, and get to work. Put your soul into, use your words to communicate it, put it in an envelope with a stamp, and send it. It will be the best 30 minutes you spend doing something all year.

Thanks Jesse, for the reminder of why I’m doing this and for the confidence I’ve now got to keep going and keep pushing to spread this farther and wider.

With love and deep appreciation,

-Andrew