It will almost kill you

In 2012 when I was working at a church, I went all in.

I flirted with burnout every week for over a year. It was hard…

Long hours, low pay.

In 2014 when I started in real estate, I didn’t know what I was doing. It was hard — learning a new skill while dealing with thousands of tenants at the same time.

The pay was marginally better, but still not great. Compared to the hours I was pulling, the pay looked even worse. I put myself through night school during this season and taught myself marketing.

5:00 AM to 8:00 PM → 5 days a week

This is when I developed my enthusiasm for reading.

One day I had a realization, “If I don’t get smarter, I will just work and work and work and never get anywhere.” One day my wife came home to a few books in the living room and asked me how I got them.

“I bought them!” I replied proudly.

“With what money?” She asked…

We had to skimp on groceries that month because I chose to buy books. That’s how poor we were.

In 2015 it became obvious I had a knack for marketing. Like a serious knack. I was doing work for extremely cheap or free on the side – and industry titans were starting to ask “Who taught you how to write like this?” My response was always the same, “Nobody… I was just desperate so I read everything out there.”

Everyday for hours, I would copy (by hand) sales letters, emails, books, and materials from great business leaders. My life was brutal for about 14 months but then it started to pay off.

In January of 2015, I got a retainer client that paid me more than my full time real estate job was paying me. I kept the full time job, and used it to fund my learning (ended up quitting later that year to go all in).

In 2016 when my firm started to blow up, I didn’t know how to hire. I didn’t know the regulations, the legalities — “What are you telling me I have to pay taxes for my EMPLOYEES?”


I had to hire to learn all of the rules.

My operations manager taught me that if I didn’t pay state taxes I couldn’t operate in the state. If I didn’t pay Federal taxes, the IRS would call me. If I didn’t pay employment taxes, I could get in legal trouble and not be able to operate. Oh, and you can’t just take money out of a business to pay for something, that’s called commingling.

“Commingling? Wtf is commingle?”

All of this on top of a dozen different types of business practices that I had never heard of. Tracking business revenue is different than managing a personal checkbook… but I hadn’t gone to school for this, I just didn’t know any of it.

“Oh my gosh what have I done?” I thought.

I had to learn the hard way, in the middle of the free fall, while learning how to manage, hire, fire, and keep all the operations spinning. When you get into operations, it’s hard to think about marketing. When you’re into marketing, it’s hard to think about operations. On and on the merry-go-round went.

And I almost burned out, many times. And many days I wondered if I wouldn’t be better off just staying a freelancer, running a small operation to cover the bills plus a little extra… but I kept going.

In 2018 I started a new firm, alongside the previous one.

Same thing.

New industry, new regulations. Fast growth. New rules. Some of those rules I didn’t understand, and I’m still processing through those ramifications today — the cost of extreme growth can accrue. I had a bias towards fast earlier in my career, now I have a bias towards right. It’s better to be slower, and right — than faster and wrong.

In 2019, another firm – this time in real estate.

Lots of new regulations… things I could not say, was not allowed to say… and for extra measure, the operating principles for that business were wildly different than the others. Money had to be tracked and allocated differently. Not only was the commingling to watch out for and protect against, there were parameters and rules around how we could spend the money we did have.

And here is the point of this rant: every significant hurdle in my life has felt like an overextension. A prolific investor that I follow says it like this, and I think he’s correct:

Whenever you get to this point, you will have a decision to make. When you really go for it, it will always look and feel the same way:

  • You say “Let’s go, I’m ready.”
  • Then sh*t breaks and breaks hard
  • It gets overwhelming
  • You crave the simplicity of the old days
  • You must decide to push through to the other side, or stay stuck on one side of history

The people who choose to go back to simplicity and safety are the ones we never hear about. Nobody is studying the people who fold up and die in the middle. They’re not worth studying and not worth modeling.

Think about it.

When you want to read the life of a great entrepreneur, you pick the ones who fought like bloody hell to advance and level up. You study Sam Walton and Abraham Lincoln — both who had extraordinarily difficult lives marked by great influence.

I’m in London at the time I’m writing this, and walked by Westminster Abbey the other day. Winston Churchill is buried there. People wait for hours to walk through his war room and look through his life — they “oooo” and “ahhhh” and we admire him…

But Churchill’s life is one that many of you would not covet or crave for your own.

We idolize the influence a person carries, while attempting to AVOID the price they paid for that influence.

Churchill survived one house fire, two plane crashes, three car crashes, four bouts of pneumonia during World War II, five wars as a soldier, and a prison break in South Africa.

The man’s life was incredibly hard.

That’s why we want to tour the museum and see his life.

When most people die, unfortunately, nobody will care about touring a museum with their lives in it. Their lives are too boring. Too safe.

I want the books written about me to invigorate and inspire and light afire the world — and in the same breath, I want my life to be simple and easy. These two things do not go together, my friends.

Can it be both?

Sure, in different seasons, yes.

Churchill picked up painting when he was ousted from his position, before and after the war. Lincoln loved to study. Roosevelt loved to ride horses until he could no longer sit up straight.

We all require periods of rest.

But we must never allow ourselves to get to the place where we crave, above all else, safety. That is when you begin to die…

Your most powerful monuments will feel like they’re going to take you over the edge. But they won’t. The last rep will often feel the hardest, like you cannot finish. But you will. And when you begin to feel that you can go no further, it is typically one more step and then you are in the home stretch.

Do not give up in the final mile.

Here’s more if you’d like to go deeper:

Talk soon,


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