How Hard Is Entrepreneurship? Nothing Comes Easy. Entrepreneurship is very, very hard work. My path to success involved dented cars, the FBI and going broke.

By Jason Saltzman

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WARNING: This article is not for the faint of heart.

But neither is entrepreneurship.

I've been self-employed for as long as I can remember. I've worked in multiple industries with a variety of different processes, learned skillsets, and aggravation. Most of the projects I worked on sucked. I was in the mortgage industry when it was the golden time, aggregated data for Fortune 500 companies, and even set up call centers across the world to sell anything and everything (mostly real estate). I don't know everything, but I know a little about a lot.

The one big lesson I learned above all else, though, is that no matter what you're working on -- no matter how glamorous it seems to the onlookers and armchair quarterbacks -- nothing comes easy, especially when you're self-employed.

Don't believe me? Let me share personal things that happened to me in my life. I hope it motivates you through the crap that most of us face when doing our own thing.

Lawsuits. And Then More Lawsuits.

My father always told me, "You are nobody until somebody sues you." After all, this is America. You can sue anyone for anything you want. In another life, I raised money on a project that failed miserably. We tried everything we could to make it work, but it just wasn't the right product. We raised money and worked our asses off, and everyone lost out. In a high-risk investment, this is one of the likely outcomes.

Fast forward to another project, and it became rapidly successful. One of the investors tried to sue us because he felt that the investment he made should follow us around for every project we worked on. That's ludicrous. This case clearly didn't go anywhere, but the stress of getting served papers was a shock to my system. It's stressful to getting dumped with a ream of legal documents, but you know what? Sh*t happens.

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The Time the FBI Knocked On My Door.

I will leave the names out of this to protect the innocent and my own ass. Once upon a time, I got offered a quick way of making money. I was approached by the pillar of a community through a friend, and was told to be the head of this network for political reasons. I was told I would get a payout for my involvement. The people that were involved were heavy-hitting politicians and lawyers. I thought it looked shady, but convinced myself it was just the way things got done. Why not get a quick buck? After all, I work my ass off and this would be easy money.

Friends, one major lesson I learned is that their is no such thing as easy money. Months after the transaction, this high-profile individual got arrested for one of the biggest crimes in US history. It was featured on American Greed. Three months after his arrest, the FBI knocked on my door. Let me tell you that this was the scariest moment of my life. Luckily, I didn't violate any laws and was cleared. Going through this process was a huge eye opener. If it looks like sh*t and tastes like sh*t, it's probably sh*t. Lesson learned.

This Is Why We Can't Have Nice Things.

I had a SICK car when I lived in Florida: an Audi A5 S model. I was in love with it. When I was younger, I cared about things like that. At the time, I ran a sales office with 75 employees. A portion of the office was a simple call center that called lists to transfer potential prospects to sales people. One of the sales managers fired a call center employee and, in an irate state, he came out to my beautiful car and smashed the door in with his foot. It was $1,000 worth of damage -- and this before I was even made aware of the issue the sales manager had with this employee.

The lesson here was that no matter how large of a company you manage, pay close attention to whom you're hiring. This person had a criminal background and we were very light on our screening process. Even though we can't control every aspect, we can take a step back and do everything in our power to lessen the outcome of something bad happening. After all, that is part of the responsibility of owning your own company.

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And Then the Feds Came Knocking Again.

Some of the highest paying verticals were the most aggressive. After working on a new marketing campaign in a very aggressive industry, I learned the term "vertical liability," which basically means that even if you are doing outsourced marketing for a company, you still have liability for whatever that company does with the client. A firm that we were doing marketing for took on too many clients and the product suffered and people complained. The FTC got involved.

One thing I learned about large government organizations is that they act first and investigate after. I guess they have their reasons for this. Our bank accounts were frozen and we had to keep the company going on our personal dime. Employees that depended on our paycheck to feed their families needed to be taken care of, and we went broke making sure it happened. We eventually got cleared from any wrongdoing, but -- needless to say -- this was just another huge hurdle to overcome. I learned that no matter how lucrative the opportunity may be, I must fully vet what I get into with proper representation.

Losing Friends.

I take my friendships very seriously. To me, a friend is the family you choose to be around. When you work with friends, bad things can happen. Because of a stupid dispute over a business transaction, I lost one of my very best friends. I guess he wasn't that good of a friend because our friendship unraveled over it, but it broke my heart. To this day, I always extend an olive branch. (If you're reading this, you know who you are. Let's grab a beer and talk it through.)

I learned to separate business from my personal life. It's a super slippery slope. I realize that this is subjective and combining the professional and personal works for some people. But it's just not right for me. I naturally become close friends with the people I work with, but our friendship is based on a working relationship.

Going Broke. Again and Again and Again.

I have gone broke about five times. I made a ton of money and lost it all, over and over again. Going broke sucks. You go from living a certain way to eating ramen noodles every night. It's a huge psychological bender. I remember being depressed and feeling like the world was going to end, borrowing money from my dad to pay the bills. (Thanks, Dad.) Guess what? The world didn't end. And it taught me who were my real friends and who were not. It showed me that family takes care of each other, no matter what. If it was not for my dad, I would be working for some boring company more than likely. He encouraged me to stick in there and do my own thing.

Reading this you may be thinking, "Wow! Jason attracts some negative crap." I can assure you that I do my best to stay away from drama and surround myself with positivity. It's just that I do a lot, and with that a lot happens. A lot of crappy stuff and a lot of great stuff. Fortunately, most of it has been great.

I know that this is not the end of my troubles. As we roll on with life things happen.

Out of all of this, the main thing I learned is that the only thing I can do is try my 100 percent best to make things work. We cannot worry about the things we cannot control. Nothing comes easy. We have to keep going. We have to push through. We have to HUSTLE ON.

Related: How Poker Is Like the Startup World, From a Real Pro

Jason Saltzman

Startup Mentor, Entrepreneur, CEO of Alley

Jason Saltzman is a seasoned entrepreneur with a background in sales and marketing. Through his role as CEO of Alley and as a TechStars mentor, he advises hundreds of startups, offering real-life practical application and creative marketing advice.  

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