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Random Thoughts On Business

Entrepreneurship is for the Mentally Unstable

By February 15, 2023May 18th, 2023No Comments

Entrepreneurship defies logic and reason. 

You work 80 hours a week so you don’t have to work 40. 

You’re going to take all of your cash and possibly some from The 3 F’s of early funding: friends, family, and fools and you’re going to put it all on the line for entrepreneurship

It’s like betting your life savings on a dice roll.  Unfortunately, it just doesn’t have immediate results. Most companies have a 90% failure rate within the first three years. 

Instead, you work yourself into madness that often leads to anxiety, self-doubt, depression, and (all too often) alcoholism. You will alienate most of your friends and some of your family, for what?

Often it starts with an itch of, “why am I making all these assholes richer when I’m doing all the work?” Sometimes it is in the grand belief that you can do it better than a former boss or some self-righteous quest to make the world a better place.  

But therein lies the key to why so many fail. 

On the 14th month of working 14-hour days without much in the way of reprieve: the money simply won’t be enough.  So you will either resort to downsizing the scale of the vision to “right size” your company OR most likely lick your wounds and return to corporate for the cushy benefits. 

The issue with the latter is the dog versus wolf scenario. Dogs stay in the backyard because they are fed daily; however, a dog that jumps the fence and experiences the freedom of being a wolf to live by its own rules… they don’t often return to being a good house dog. They will always long for running the mountains. Their intolerance for malignant corporate politics and disdain for ineffective leadership will leave them wishing for death daily. 

“I want to start my own business.”

“No, you don’t.”


“You want to be the type of person who wants people to think that you could start a business. If you wanted to start your own business, you would be doing that right now… and not trying to convince me.”

(I know. I’m an asshole.) 

But if you want to start a business. Just do it. Get the LLC. Then open a bank account. No one is stopping you. You can do it in an afternoon. 

And then… make a ton of mistakes. Learn how absolutely little you actually know about what it takes to run a company. Then you will learn some skills, get some clients, hire some people, lose some clients, make more mistakes, have panic attacks about how to make payroll, win some big accounts, develop a drinking problem, hire consultants, fire consultants, go networking, swear off networking, and then… come to me and I will share war stories and pass along the advice that was given to me by those who also earned every gray hair on their head. 

But you have to start. 

You have to make mistakes. Wilderness Agency isn’t my first company. It’s not my second. It’s just my first “successful company” and even while writing these words I reflect on how much debt I’m still in…. thousands and thousands of dollars invested in my education of what not to do and who not to trust. 

Because there also lies another truth about why companies fail. The story I share is about the couple who wants to start a pizza restaurant. Close to retirement. They decide, “let’s bail out early and start our restaurant.” They make a great pizza and everyone loves it. They will make a killing. And then… 9 months later the place is closed and they have lost their retirement savings. 


Because they didn’t know squat about the restaurant business, the food part of a restaurant is maybe 10% of the business. Once you have to take your recipe and scale it: you have to cut corners to make it profitable at market rates. Then you have to figure out how the back of house and front of house work. Inventory management; i.e. when it snows in Ohio: NO ONE goes out to eat and all of that produce is ending up in the trash. Then you have to deal with the fact that people don’t show up, the kitchen staff is high, the bar staff is giving away free drinks (mostly to themselves and their friends), and half the staff are sleeping with each other.

I know because I lived in that world for 8 years before I realized, “I’m not gonna ever end up in this business.”  It’s an impossible way of life. 

“What is your best advice for someone who wants to pursue entrepreneurship?”

I get asked this often. Here is my canned response:


No matter how curious. No matter how much you want to scratch that itch. Resist the urge!  More than likely, you will live a happier life. 

However, if time passes and you can’t not “try it” (my favorite phrase from idiots doomed to failure… “I just wanna try it”… oh really?  To me it sounds like “I just wanna try drowning, how bad can it be?”… good luck!)

Simon Sinek prophecies suggest that we must have our “why” figured out. That motive for what you and your company stand for and what your employees will stand behind. It’s got to be bigger than money and does help with the 14-hour days. 

It’s a big idea. But I will warn that it has to be authentic and relatable, i.e. if Phillip Morris suggested that their products were helping to bring people together OR help fund cancer research… probably not gonna work. 

“I’m an entrepreneur too!”

Sigh… take me now, Lord. 

Again, (in case you forgot) I’m an asshole. I believe that there is a VERY BIG difference between entrepreneurs and small business owners. 

There are a significant number of people who own lifestyle businesses. These businesses help the owner to have the life they want, ie 4 weeks of vacation a year instead of only 2 from corporate. 

There are a lot of small businesses. The business where the owner has a nice lifestyle, not too many headaches, and a small crew of folks that are making minimum wage or paying close to a living wage. 

It is my belief that an entrepreneur is something else. It is someone who is building a business not solely for increasing their personal wealth, but also that of their team and their community. 


I do believe that I have earned the right to call myself an entrepreneur. I’m not. I want to be. I’m trying really damn hard. I’m trying to pay my team higher than industry averages. I’m trying to help companies in my community to grow and bring them new businesses. But if you haven’t already gathered this from the ranting above: it’s stupid hard. 

Sorry. Not sorry. 

I know that all of this doesn’t sound grandly inspirational, but what I hope that it does do is serve as a nice cold splash of reality for any “wanna try it” folks out there. I sure as hell wish someone would have told me some of this. I don’t think it would have stopped me. But hopefully prepared me. 

I will say that it’s easier now that I have some mistakes behind me. It’s easier with some gray hair. Because on the other side of all that shit, I survived: I learned that what I value more than money is developing my team and seeing them grow as people. That is what keeps me going. The idea is that I can build my army of people who are also determined to help grow our community. 

Wilderness Agency’s “Why?” is in our mission statement:

Grow Companies. Put people back to work. 

I’ve spent too much time in the wilderness to ever go back to being inside the fence. So every day I have to go back and keep hunting for my dinner and my team’s dinner. I have to keep grinding and keep humping the American dream. 

And truth be told: there’s nothing I love more than playing this game. 


     + Richard Kaiser

Richard Kaiser

Some of my fondest memories from my formative years were from Boy Scout camps sitting on rough, wooden logs that encircled a crackling fire sharing stories with the other boys. I believe in my heart that it is a human need to be told stories. We crave stories much in the same way we crave love. The work we do at Wilderness Agency is based upon this primal need. We bring together some of the best creative talent from around the world to tell our client’s stories, to share their passion with the world.