I've bought over $100 million worth of real estate.

6 things I wish I knew at the beginning:

Is it potentially possible that doctors actually are still learning and new information is coming available all the time?

Doctors handed out cigarettes to patients once upon a time and they fogged playgrounds with DDT.

We should be happy people question the establishment.

For the last few weeks I’ve been turning my phone off at 7pm and turning it back on at 7am.

3 hours before bed and 1 hour after wake.

6 out of the last 7 days I’ve done no screens at all during that time period.

Very very hard to do but I highly recommend it.

The best advice I can give:

Do not marry somebody who comes from a messed up, disfunctional family.

They break the cycle maybe once or twice in ten.

Do not play those odds.

Because nothing will ruin your life faster than a mentally unstable spouse.

The rules of people:

How to get rich without getting lucky:

A funny thing:

Small businesses will spend $75k on a truck or $500k on a building or $10,000 a month in rent…

But they’ll run their multi-million dollar business with a $500 website that isn’t optimized.

I've hired hundreds of people in my career.

I've let go family members and folks who stood up at my wedding.

From part time laborers to executives who help me raise capital for large real estate deals to full time off shore folks.

Here's 10 things I've learned:

I've bought over $100 million worth of real estate.

6 things I wish I knew at the beginning:

A hill I'll die on:

95% of entrepreneurs should forget about technology (a few big fish and a lot of sophisticated fishermen) and focus on small business (small fish everywhere and really crappy fishermen).

In 2021, I worked on a career-defining $75M self storage deal that could have generated tens of millions in enterprise value for my company Bolt Storage.

But we lost it to a competitor...

It hurt!

Here's what happened:

A hill I'll die on:

95% of entrepreneurs should forget about technology (a few big fish and a lot of sophisticated fishermen) and focus on small business (small fish everywhere and really crappy fishermen).

If you are consistently working 60+ hour weeks you have one of three problems:

There is always a bottleneck in every single business.

Here are the stages:

10 important things I've learned about hiring:

Bad advice:

“Make money doing what you love.”

Good advice:

“Make money chasing an opportunity and then spend your time doing what you love.”

SELF STORAGE UPDATE:

Same store revenue was up 14.1% in Q1 2025 over Q1 2024. Occupancy is up 7% year over year.

We have officially refinanced all of our new acquisition debt from our purchases from 2020-2023.

Over the last 12 months we've refinanced over $40 million of debt.

I'm convinced a lot of my success in life can be attributed to taking the path of least resistance.

I got a lot of advice like "do what you love, log 10,000 hrs, become an expert".

Horrible advice.

Instead, look at every decision like this:

What are my odds of success?

In 2021, I worked on a career-defining $75M self storage deal that could have generated tens of millions in enterprise value for my company Bolt Storage.

But we lost it to a competitor...

It hurt!

Here's what happened:

Too many folks set the bar way too high with entrepreneurship. The next million dollar company. The next sexy startup.

Forget all that.

Why isn’t the goal to build something that pays you good $ every year and requires only a few hours of your time per week to make it happen?

A mindset shift that really changed my life:

Walk into every single interaction with the goal of adding as much value as humanly possible.

Don't think about charging money, withholding info, etc. Prove you know your stuff.

Help in a massive way. Gain trust. Profit later.

Too many folks set the bar way too high with entrepreneurship. The next million dollar company. The next sexy startup.

Forget all that.

Why isn’t the goal to build something that pays you good $ every year and requires only a few hours of your time per week to make it happen?

Normal people eating 150-200 grams of protein daily will go down as as big of a disaster as the lead pipes that took down the Roman Empire.

How to figure out if your business idea is any good in 5 minutes or less:

I've been serious about personal development and getting better at business for 15+ years.

But not just reading and thinking about business...

I've put the concepts to work.

I sold my first business for 7 figures and built a real estate portfolio worth $100 million+.

I

I once made $10,000 in profit in one weekend as a college student with no money.

Here is how I did it:

6 (unconventional) rules of business:

10+ years ago, in a college entrepreneurship class, I pitched my sweaty startup.

They asked me what my "moat" was.

"We'll answer the phone & do what we say we're going to do."

They told me it was a bad idea and would never scale.

We sold that business for 7 figures.

A mindset shift that really changed my life:

Walk into every single interaction with the goal of adding as much value as humanly possible.

Don't think about charging money, withholding info, etc. Prove you know your stuff.

Help in a massive way. Gain trust. Profit later.

This was one of the hardest things I’ve ever done.

Coming April 29th.

The hardest thing about entrepreneurship, real estate, or anything else worth doing:

You have to be able to look at incomplete information...

Or a complicated problem without a clear-cut solution...

And make a good decision on which way to proceed.

I have 50 remote employees at my self storage company.

Half of them have never met one another in person.

They live and work all over the world.

Here’s how we do it:

5 things about health I wish I knew 15 years ago:

How to grow a business the old fashioned way:

The truth about success.

50% or more can be attributable to just running with the right people and being in the right place at the right time:

The life of an entrepreneur can be brutally difficult.

But nobody talks about it.

Time for a stiff drink and a few words on some of the most stressful periods in my life.

A friend of mine makes about $500k a year and controls his own schedule.

3 kids. Travels a lot. Has hobbies. Works 30-40 hrs a week.

Here is the career path:

I've been serious about personal development for 10+ years.

But not just reading.

I've put the concepts to work and built a portfolio of successful businesses.

Here are a few of my top takeaways:

The hardest thing about entrepreneurship, real estate, or anything else worth doing:

You have to be able to look at incomplete information...

Or a complicated problem without a clear-cut solution...

And make a good decision on which way to proceed.

I have 45 remote employees at my self storage company.

Half of them have never met one another in person.

They live and work all over the world.

Here’s how we do it:

What the internet gets wrong about real estate:

What successful people understood before they were successful:

I've been micro-dosing psychedelic mushrooms for about 2 months now.

Haven't felt anything.

Except better mood, more excited and playful with my kids, more improvements in golf game, clearer head.

I recommend it.

How to get rich without getting lucky:

Find a way to make $100 an hour doing something simple IN YOUR TOWN.

Do it until you have $10k+ in the bank and you’re too busy to sell new customers.

Hire employee for $25 / hr to do what you do so you can sell new customers.

Repeat.

I attribute a lot of my success to running every major career decision through this test from age 20 onward:

Which route increases the odds of me being able to do whatever I want with 100% my time when I’m 35 yrs old?

This is what my wife and I spent our free time doing 11 years ago.

I wore holes in 3 pairs of jeans writing 2000+ ads just like this on the streets of Boston.

Marketing budget was $200 in chalk.

It worked. We got 2,000 customers first year and $500k of revenue.

There are a lot of underrated skills in this world.

Attributes that aren’t openly discussed but are widely shared by the most successful among us.

Here's how you can increase your chances.

A mindset shift that really changed my life:

What the internet gets wrong about real estate:

What successful people understood before they were successful.

A short thread.