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 thread.

The thing about being an entrepreneur is that there is nobody you can ask for help.

There is no boss you can call and dish off the really hard problems.

And there is no track-record or “way of doing things” that is proven.

So you have this constant nagging feeling that what I’m doing might not work and I might lose a lot of money.

When our student storage company took off a bit in the early days it was equally as stressful because we didn’t know what the hell we were doing.

I was a senior in college trying to graduate and finish out my track and field career.

If found myself in the hotel the night before the meet answering customer service calls and emails until 2am.

And between events on meet day.

My first real breakdown was a year later on the streets of boston.

We were 10 days into a crazy work period. 20 hr days.

Our workforce was overwhelmed and in the middle of one day two employees quit and abandoned two trucks full of customers stuff on the city streets.

We had no employees left so I rode my bicycle to the truck and single handedly unloaded the thing through the city between 9am and 3pm.

Then rode my bike to the second truck and did the same between 4-midnight.

Around mid day one of our guys sent me a text that he dinged up the roof.

He had driving the truck down a “cars only” road in boston.

It’s not that bad he said.

I made him send me a picture and this is what I got.

At one point, as more employees called out for the next day, and I hadn’t stopped to eat or drink anything in 8+ hours, I laid down on the sidewalk and cried.

Called my mother. Cried some more.

I wanted nothing more than to stop doing this and go home to my bed.

But we had hundreds more customers that needed delivered so the hell lasted another 6 days.

We barely got through it with our company in one piece.

On my first self storage development deal 3 years later we raised over $500k from family and friends to build a building on a $1.8MM budget.

We bought a parcel and got to work.

But surprise after surprise crushed out budget. We ended up spending $2.4MM.

So I had to call them all and try to convince them (+ bank) to put in more money because I was fresh out.

We were a few weeks away from totally running out when we finally got it raised.

But we thought we were going to lose everything and end up with a 1/2 done building.

When covid hit, we had 4 employees and no warehouses and our colleges started sending kids home with very little notice.

We had to flip our business model on our heads, throw down 20 hour days, fly to DC and Ithaca and pack up the dorm rooms of kids using FaceTime.

We had to hire 70 employees, make deals on thousands of square feet of space in HCoL cities, find a way to get packing supplies on site in days, and arrange lodging for our entire team during a pandemic.

It was two months of hell.

Spending tens of thousands a day to do work on net 120 terms.

And building a totally new business model as we went while every one of our customers were insanely stressed themselves.

Insane liability and expectations from universities and customers.

We bought a storage facility at auction in 2019.

Only to find 130 of the 185 units had abandoned items inside them because the owner had severe dementia and had lost track of them.

We had to try to locate them and organize an auction of every unit. We took on a ton of liability

These are the things folks don’t talk about.

You hear about the money, private jets, wins.

You don’t hear about the struggles that come along with building an airplane as it’s ascending into the air.

With no parachutes on board.

Entrepreneurship will humble you.

And break you down.

And you’ve got nobody to save you but yourself and a little bit of luck.

There have been days where somebody could have called me and offered me a job and I would have taken it.

Shuddered everything. And given up.

There were days when the alarm clock would go off at 4:30am and Id lay there for a second knowing I had 20 brutal hours of physical labor ahead of me.

And 10 days just like it on deck.

And absolutely no other option because I was too deep to give up. Too many customers and employees counting on me.

And a baby at home and a house payment to make.

And it makes you fucking scared.

And anxious. And doubtful.

And absolutely miserable.

For every person like me who was lucky enough to come out alive on the other side...

There are hundreds of thousands of stories that end in failure.

Bankruptcy. Smashed egos and ruined households.

This life isn’t the life most folks make you think it is.

If you’ve ever had to fire your best friend or push your body to its physical and mental limits you know what I mean.

Nothing fun about 99% of this stuff.

If you’ve ever had back to back hell days for a few months straight and came home to a wife ready to pack up and get out of the mess you’ve created.

Or if you’ve ever had everything on the line and all the chips on the table and felt utterly and completely helpless.

It makes the highs higher and the joys of winning every bit sweeter.

But at what cost?

Sometimes we wonder why the hell we even do it.

And the worst part...

If you fail. And everything goes to waste.

You know, deep down, it’s all 100% on you.

You weren’t good enough. Your decisions weren’t good enough.

You have no boss to blame. No fingers to point.

It’s the ultimate accountability.

And wrapping your head around that when times get tough and failure is easy to visualize right in front of you...

Is the hard part of entrepreneurship.

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The craziest part about this suffering and uncertainty...

Is that it makes a certain type of person feel alive. And we can’t get enough of it.

And I have a confession to make.

I’m guilty of pitching entrepreneurship and wealth in a way that makes someone appear foolish not to give it a try.

But it is not the right move for 95% of folks.

Writing this was an emotional trip down memory lane.

Still sitting in my truck staring off into the abyss right now actually. It’s been a wild 10 years.

I hope other entrepreneurs are encouraged to share their stories.