The true stress and hardship of entrepreneurship

Is it time to sell your business?

I launched a business brokerage.

We now have 800+ buyers on our distribution list.

When we get a listing we’ll do a podcast episode with the owner, a breakdown of the business to my 140,000 newsletter subscribers, and several tweets promoting the listing (I get 50 million impressions a month on Twitter).

Want to sell your small biz? I can get you a great deal. Click here.

People rarely talk about the losses. The hardship. Failure.

I’ve experienced a lot of it.

Business is hard. Making money is hard.

Everyone on social media will act like it grows on trees and running a business is glamorous and stress-free.

It isn’t.

The pressure is intense. You have families and people who depend on you to pay their rent. You have customers who are entitled and will belittle you.

Negotiations won’t always go your way. You’ll make mistakes that cost you money when it hurts the most.

And EVERY TIME the phone rings there is a problem that everyone is looking to you to solve. Uncomfortable conversation after uncomfortable conversation. People demanding more and more of you and more and more for themselves.

My career has been advanced to levels I never imagined because of this place.

With that comes a hell of a lot of stress and challenges. I have a duty to my growing number of employees who are looking to me to guide them down the correct path.

And I’m just figuring it all out as I go. Doing the best I can. Making mistakes and owning them.

The problem with it all is that as men we often get our entire self-identity wrapped up in our businesses and our careers. I can sit here and act like my priorities are my kids and my hobbies (they are) but I know deep down that I’m known by other people as a businessman.

It is my identity. The legacy I’ll leave will revolve around companies and employees and numbers in an invisible bank account on a screen somewhere.

I’ve labeled myself as a businessman here in front of you and its why you’re reading these words – the words I’m down in my basement writing at about 1am because I can’t sleep.

The evenings are always the worst. The wicked serotonin levels are higher so the small stresses become big stresses in the evenings. When I wake up they won’t seem like that big of a deal but right now they bring on the anxiety.

Because I have a wife sleeping in this house who is completely trusting me to guide our family financially. I have three little kids peacefully sleeping in this house who are trusting me to raise them the right way. Who need me to be strong and teach them how to treat other people and how to live the right way. How to be humble and kind and productive.

And with my identity and my responsibility comes serious risk. What if I fail? What if I make a bad decision that brings it all down? I’m in the trenches, fighting, with everything on the line.

Self doubt. Anxiety. Fear. Responsibility.

I feel it all just like you do.

And I’ve got to wake up every day and bring it.

The decisions need made. They can’t wait for me to “gather data” or “get advice”. They can’t wait for me to sleep on it. I have grown adults with rent to pay and families to feed looking to me to solve the problems so we can all keep going.

But there is no how-to book. The people giving me advice don’t understand it all. Hell, many times there isn’t even a right answer or I’m choosing between “bad” and “worse”.

And every single bit of it is easier said than done.

The haters are quick to hate. They’ll copy you when it works and laugh at you when it doesn’t.

They think the way to own the tallest building in town is to tear down all the buildings taller than their own.

Crabs in a bucket.

The people saying it is easy aren’t in the game. They have never had an friend cry in your arms because you fired them and they have no way to feed their family and they let everyone around them down.

They’ve never had to part ways with a dear friend who was in their wedding a few months earlier but the company just doesn’t have the ability to help them achieve their goals.

They’ve never had an employee quit while in the middle of a work shift after making a 6 figure mistake.

It’s easy to look down on the man in the arena and think you could do a better job. An overweight fan in the 5th row booing the starting quarterback of his own team who is out there trying to do his job. An anonymous account on Twitter throwing haymakers to anyone who will listen.

People never see the stress and struggle behind the scenes. They don’t know the truth.

The truth is that this stuff is not easy – no matter how easy it looks.

The truth is that very few business owners are rich.

Most are unhealthy, unbalanced and a few unpaid invoices from being completely broken financially and as a man.

90% of businesses fail for a reason.

Business is hard and making money is hard.

It is NEVER easy.

It isn’t easy for you and it isn’t easy for me.

I’ve just got to wake up each day, step over the fear, trust my gut and walk out into battle.

I promise you this:

I’ll make mistakes. I’ll let people down. Ill make poor decisions. I’ll lose big chunks of money at times. You can’t count on me to get it right every time.

But you can always count on me to bring it every single day.

Onward and upward,


P.S. I’m an investor in a new web development firm called WebRun.

They built this amazing investor landing page for my real estate firm and I’m VERY impressed by their work.

If you need a website overhaul, new website or landing page – schedule a call with Will at WebRun to get a free proposal!

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About Me

I started the Sweaty Startup in December of 2018 because I believe the Shark Tank and Tech Crunch culture is ruining the real spirit of low-risk entrepreneurship.