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Via Chicago Tribune : Recently, I returned to my alma mater, the University of Illinois (after 20-plus years), to give a talk on entrepreneurship. It was energizing to speak to budding entrepreneurs on campus and share lessons from my career building and selling companies. As always, my favorite part was Q&A, when I engaged directly with undergraduate and graduate students about any topic.

Most of the questions were some version of “How hard is it to build a business?” or “How do I know if I can do it?”

I started off trying to be inspirational and sanitized, but these students were interested in the bitter realities of entrepreneurship, no holds barred. Below are some of the unglamorous (but true) points that came out of this chat:

Hard work isn’t enough

Working hard when you love something is a joy. Most hardworking investment bankers love M&A, and driven surgeons typically love medicine. But start a business, even in an industry you love, and you will inevitably work super hard at activities you may despise. A startup CEO will, at various stages, handle hiring, firing, sales, production, finance, customer service, operations, purchasing, even shipping clerk. It doesn’t matter what you enjoy, or are skilled at.

Can you be a chameleon?

Besides wearing different hats, entrepreneurs have to occasionally transform their personas. You’re a timid person? Good luck chasing that deadbeat client to pay so you can make payroll. Not detail-oriented? When you get served with a lawsuit, I promise you’ll change real fast. Don’t like conflict? Wait until your best employee defects to your main competitor. This is why most businesses fail — dealing with unending problems while facing 24/7 financial uncertainty is a “responsibility tsunami” that overwhelms most people.

Don’t micromanage

The saying “if you want something done right, do it yourself” works perfectly in school, and as an employee. But micromanaging is a killer for entrepreneurs. A “one-man show” company usually ends one of two ways — the owner burns out because of the tireless grind, or despairs that business never grows. To build a company that can scale rapidly, you have to hire great people (which is really hard), then trust them with your life (which is impossible for micromanagers).

It’s all about people

If your small business earns $150K in profit, it may seem insane to hire a superstar who might bring in million-dollar clients, but who requires a six-figure salary. But that’s the kind of sleep-depriving risk you must be willing to take if you want to build a lasting enterprise. And for anyone who dreams of selling their business, know that buyers only provide huge exits to companies with demonstrated depth of management.

It’s lonely if you fail

When you start your business, a part of your life gets painfully cut off from friends and even family. Why? Because very few people will understand what you are going through, and you will never have time to explain every labyrinthine problem. If things go downhill despite your best efforts, it’s pointless to complain, because it was your choice to start a company in the first place. Most people will offer cold comfort, reminding you that “you can always go get a job, right?”

It’s lonely if you succeed

If you’re lucky enough to beat the odds and build a successful business, strange and awkward things happen if you share your worries openly. After friends (even close ones) roll their eyes and say “Whatever, I wish I had your problems” enough times, you stop being candid because you feel self-conscious. All entrepreneurs eventually learn that isolation is occasionally part of the job description, whether you like it or not.

Do you like pressure?

When I was selling my first business in my 20s, a multi-billion dollar competitor sued us during due diligence. Our buyer threatened to walk, and I felt crushing pressure unlike anything I’d experienced. One night, after a brutal 15-hour legal marathon, I passed out in bed wearing my suit. I woke up in agony and discovered that my pillow, face and neck were soaked in blood. I had chewed up the inside of my cheek so badly that at 3 a.m. I needed 11 stitches in the ER to stop the bleeding. The next morning, I had to present our case to 10 people from the buyer’s side. I smiled, ignored the tennis ball-sized purple lump on my face, and got on with it. The good news: our deal closed. The lesson: in entrepreneurship, the show must always go on.

No one has the answers

Most of us have business heroes we look up to — brilliant/rich/famous people who we are certain have everything figured out. I’ve been fortunate enough to get to know some of these luminaries, and it definitely wasn’t what I expected. The sobering reality: these “legends” are normal, flawed, anxious humans, exactly like you and I. None of them has a magic bullet about anything. They made it by doing what you better quickly learn: to find answers from within yourself.

Luck is vital

If there’s a universal truth among my friends who have built successful companies, it’s that we all had critical “make or break” junctures in our professional lives where things went our way because of pure, unadulterated luck. Does luck favor the prepared? Of course. But do legions of people work their tails off and still fail because of bad luck that is just horribly unfair? You bet. As irrational as it sounds, I believe that I am a very lucky person, and that I would not be where I am without this trait.

You need thick skin

Everyone will have an opinion about you and your company, but it’s crippling to tie your self-worth to what others think because you’ll be paralyzed and insecure. A longtime mentor gave me wise advice: He said it’s not even my business what others say about me. I love this because it makes it incredibly easy to ignore useless gossip. You have to be driven internally because haters are always going to hate. And the reverse is true: Some people will artificially put you on a pedestal, and that’s just as important to brush off. Do what you want to do because you want to do it, period. Authenticity is always the right answer.

It’s completely worth it

Entrepreneurship can be an unrelenting nightmare that ruins your personal and professional life. It’s simply not for everyone. But, besides having my kids, building companies is the best thing I have ever done. Life is full of contradictions, and this is one that I have a hard time describing. When I see my employees crushing it with great performance, closing big deals with great clients, and having fun doing it, I am filled with a satisfaction that can only come from the act of creation. So, if you know deep down that you can do it, jump in, and I promise you won’t regret it.

 

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