Young Money Turns 1!

Time flies when you are writing words!

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One year ago last Friday, I sent the following article to 60 people:

Today, I sent the article that you are currently reading to 12,700 of you. What a ride.

Thank you, all 12,700 of you, for giving me a few minutes of your time every week. Your time is the most valuable asset that you have, and I don't take that responsibility lightly.

To celebrate Young Money's first birthday, I wanted to reflect and share a few thoughts with you.

For starters, I wanted to share Young Money's origin story.

Ironically, I never planned on starting a blog. I certainly never intended to write one for this long. The fact that I started this thing in the first place was a fluke.

Last summer, after spending the first 18 months of my professional career updating financial spreadsheets from my apartment bedroom, I needed a change.

I was in a unique spot in my life: I was planning to enroll at Columbia Business School in Fall 2022, I had enough money saved up that I could cover my bills until then, and I didn't want to keep working this same job for another year. My monotonous, Groundhog Day-like existence was driving me crazy. I'm sure some of you can relate.

The question, then, was what to do in the interim. One recurring idea was travel. But travel where? For how long? How much would it cost? Was that really the "right" thing to do for a year, or just the impulsive response to my work-from-home-induced cabin fever?

I wrestled with this dilemma for weeks, until my roommate gave me a book: Vagabonding, by Rolf Potts. I read it in one night. This book is a must-read for anyone who has any desire to travel.

That book changed my life. Thank you, Chase, for an excellent gift.

So it was settled, I was going to quit my job at the end of the summer, buy a one-way ticket somewhere overseas, and figure everything else out along the way.

Spending 18 months staring at your bedroom wall can make you do some crazy things.

While I had enough money to fund my travel plans (play your cards right and a vagabonding trip is cheaper than you would think), I wanted to make some money on the side. I realized that writing could be the perfect "job" while I was backpacking around Europe.

I applied for all sorts of writing roles with all sorts of companies. Two that stood out were gigs with Morning Brew and Collaborative Fund.

At this point, my writing experience had been 10 Seeking Alpha stock write-ups and a few short-form satire pieces for Hard Money. That's hardly a portfolio worth reviewing.

I had, however, also hatched the idea to write a book, The Inefficient Market Hypothesis, that would cover ~20 of the craziest things that I had seen in financial markets. I knew nothing about writing a book, marketing a book, or really anything about anything to do with books. But I thought it was a good idea, and I had written a few chapters.

Knowing that my lack of "writing experience" meant my applications would be forever lost in application portal purgatory, I went straight to the source, DMing several folks, including Morning Brew's CEO Austin Rief, about my interest in writing for them.

To my surprise, Austin actually responded.

For those curious, here's the message I sent Austin. This is a textbook example of how not to cold DM someone. Surprised I got a response. NEVER SEND MESSAGES LIKE THIS TO STRANGERS OR LITERALLY ANYONE.

Yes, Austin was cool with me sharing this. No, don't DM him.

As you can guess, I *did not* receive a job offer. To be fair, I wouldn't have hired me either. The samples I sent over weren't hire-worthy.

I realized that my lack of writing experience was making it impossible to land a writing job. How can one create writing experience to land a writing job, if they don't have a writing job?

Start their own newsletter.

So I went to Substack dot com, created a site called "" (youngmoney was already taken) threw a link to it on Instagram and Twitter, and started writing. Why Young Money? Because I was 24, and I was writing about money. How did I come up with the image? I tried to draw Benjamin Franklin on the $100 bill.

Close enough. If nothing else, the image is memorable.

I figured I would write about finance and stock stuff for three months, reapply to one of those jobs, and write for a publication until I began graduate school.

Well, here we are 12 months, 12,000 subscribers, and 100 blog posts later. The blog is still going, and I still haven't reapplied to any of those jobs.

(Though Austin has since subscribed to Young Money, and we chat pretty regularly, which is cool. I think he would agree that my content has improved.)

This side quest, which was only supposed to last for a few months, has become one of the most important parts of my life. It's funny how that works, isn't it? A year ago, my projected future looked something like this:

Write Young Money, write for a bigger publication, enroll at Columbia, intern for a consulting firm/bank, work for a consulting firm/ bank, climb the corporate ladder, and eventually make partner or land a C-Suite position somewhere.

Now? My projected future looks something like this: Write.

All I want to do is write. And write. And write. Plus I despise working with spreadsheets, which really puts me at odds with the day-to-day in those other industries.

Existential boredom led to a desire to travel led to searching for writing roles led to rejected book sample job applications led to starting a blog led to this post right now.

The number of possible outcomes is always larger than you can imagine, as the last year has shown. I guess that's how most origin stories work though, isn't it?

Some Highlights

The path from this random genesis to where we are today was by no means a straight line. It was extended plateaus interrupted by periodic explosions. Here is my Substack subscriber graph from last summer to January, when I switched to beehiiv.

Flat, flat, flat, then BOOM in late September, when a piece caught traction. And again in November, when it really started running. Then I switched over to beehiiv in January. There were several jumps over the last six months, but they look minuscule thanks to the wave of new readers from last weekend (hello, all of you!)

The Pareto principle states that roughly 80% of consequences come from 20% of causes. Young Money is a great example. I have published close to 100 articles over the last year, but a few key moments have contributed to the majority of my growth.

Some of these highlights:

  • Nick Maggiulli sharing my article about blowing a lot of money last fall

  • Packy McCormick sharing a piece I wrote about five dumb investments that would have made you rich last October

    • This piece made an appearance on the Compound and Friends podcast, and MarketWatch highlighted it a few days later

  • Tim Ferriss linking a thread I wrote on Twitter in his newsletter, which indirectly drove 500 subscribers to Young Money in May

  • Katie Gatti Tassin linking one of my articles on her Money with Katie blog

  • Alex Banks sharing my blog in a thread of his favorite newsletters

None of these highlights were planned. I've never paid for any promotion of any kind. These highlights only happened because I kept publishing every Monday and Thursday, and every once in a while someone liked a piece enough that they would share it with their audience.

Write, write, write. Nothing, nothing, nothing. Then suddenly, when you aren't expecting it, everything. That's how writing works. That's how a lot of things work.

Some Thoughts

Here are a few revelations that I've had while writing this thing.

1) A certain level of ignorance can be incredibly useful.

At first, I had no idea that writing, especially writing independently, could be a viable career path. I figured to make a living writing, you fell in one of two groups: a best-selling author or a journalist for a large publication. That's it.

Then I saw other newsletters and blogs that were making hundreds of thousands and even millions of dollars from advertisements and subscriptions.

I never once stopped to think, "Holy cow, it must be incredibly difficult to scale an audience to that size."

I thought, "Holy cow, YOU CAN GET PAID TO DO THIS STUFF. THAT'S INSANE. All I have to do is write good stuff and build a big audience."

This was an all-time ignorant take that ignored just how difficult it is to 1) consistently churn out quality content and 2) build an audience. But this ignorance gave me the longevity needed to get through the months of doldrums that any creator must face. Months of shouting into a void to just hear silence echoed back. Months of finding my voice, marketing my blog, and experimenting with different content. I never once stopped to think "this sucks." I never really thought at all. I just kept writing.

A certain level of ignorance can be incredibly useful.

2) Stories reign supreme.

When I started this thing, I was still trading stocks like a madman. As an active market participant, I figured that I would publish regular stock write-ups and personal finance tips. The funny thing is, I hated reading stock write-ups. I didn't care about EBITDA or CAPEX or FCF margins or anything like that. I also hated reading generic personal finance tips. How many different ways can you explain the tax benefits of using a Roth IRA for 40 years?

I liked reading stories about people, money, and markets. How Michael Burry shorted the housing bubble, and how FedEx's CEO saved his company from bankruptcy at a Vegas blackjack table.

I was interested in reading about the regrets of those who spent their lives chasing material things, and the mindsets of day traders who made and lost millions in the Dot Com bubble.

Numbers were boring, stories were captivating. So I leaned into the stories.

3) Real is underrated.

As a writer, there is this desire to write what is "acceptable." Not wanting to step on toes, be offensive, or go against the status quo. But as a reader, acceptable is boring. Authenticity is captivating.

Three books have had a profound impact on my life: Vagabonding, Greenlights, Man's Search for Meaning. There was nothing normal about any of these books. These books were human, and they reflected the thoughts and feelings of their authors.

So I leaned into the "real." And it turns out, what's real to me is real to many others as well. A year ago, I wanted to play it safe. "Here's how you build wealth over time." "Stocks go up 8% each year."

But no one wants to read the 100th regurgitation that "stocks go up over time." People want raw emotion. Fear. Excitement. People want stories that they can relate to. They want to read the revelations that they have always known to be true, but could never put into words.

So I published the revelations in my own mind for the world to see.

Many of those revelations have been well-received. Hundreds of you have emailed and messaged me, responding to my thoughts about life, money, careers, opportunity costs, tradeoffs, and everything else.

And a few of you have even changed something in your lives because of something I wrote. That is a wild experience, and it brings me to my last point:

4) The audience is the only thing that matters.

Without all 12,000+ of you, this blog would be nothing but a journal. The value of writing is measured by the impact that it has on its audience. Everything else is irrelevant. You guys have set a high bar for me, and I strive to hit that benchmark every week. These pieces come from me, but they are meant for you.

What's Next?

Honestly? I'm not entirely sure.

There is one constant: every Monday and Thursday, you will continue to receive my best work. Everything else is noise. Maybe Young Money will remain an independent publication, maybe I will partner with someone else down the road. Who knows. The last year has shown me that predicting the future is pointless. You can't predict the unknown variables that will impact your decisions down the road. What I do know, is that every piece I publish shifts the odds in my favor.

Success, or lack thereof, is determined by the ability to do ordinary things for extraordinary lengths of time. My outlook is pretty simple: keep writing, and writing, and writing, and good stuff will happen.

So thank you, all 12,700 of you, for giving me a few minutes of your time every week. Hopefully this time next year, I will be writing to 100,000 of you.

- Jack

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Jack's Picks

  • Morgan Housel dropped a fire post about the two big lifestyles you can choose from, and a crazy 1968 sailing race that left one competitor dead and the other happier than he'd ever been. Check it out here.

  • The Wolf of Franchises wrote a great thread on Nathan's Hotdog Eating Contest, definitely worth a read for those interested in America's greatest competition.

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