5 Lessons Every Entrepreneur Has to Learn the Hard Way



When you set out to become an entrepreneur, nobody can prepare you for what you’re about to experience.

Building a business takes practice, patience, persistence, and a whole lot more, many of which you can’t learn until you’re standing in the fire.

As a successful entrepreneur, I want to shed some light on the lessons most have to learn the hard way–and help you move through those challenges quickly and effectively. Consider me your paperback mentor.

1. Having talent isn’t enough.

The truth is, you could be the most talented person the world, the smartest one in your class, born with an exceptional gift–but if you’re not willing to work, you won’t make it very far.

I have always been the type to feel like I had to work so much harder than everyone else in order to succeed. But I’ll tell you what, it was my iron will that allowed me to build successful companies, and nothing else.

You can’t rely solely on your gifts and talents to carry you. Whatever you’re good at, take that as a lucky head start, and then get to work.

2. What goes around really does come around.

Ever heard of the phrase, “What goes around comes around?”

It’s so true, especially in the business world. The world may seem like this huge place when you’re starting out, but just you wait. As you get older, it begins to shrink. You start to see people come back into your life that you thought you’d never see again. You never know when someone will reappear and be in a position to help you–so don’t burn bridges.

Never let your emotions get the best of you if a business deal doesn’t go your way. Always be professional. Don’t be a hothead and blow off steam because you think, “Who cares? I’ll never see this person again.”

You never know.

3. Complacency will kill you.

I want you to imagine for a second that you’re at the same point in your business that I was back in 1978. You’re off and running, ready to grow your business and take on the world. 

It’s your job to harness that enthusiasm, and use it wisely–because you don’t want to get fat on your success. A lot of entrepreneurs can fall into the trap of getting complacent once they reach their initial goals. Why? I have no idea. It’s almost like some of them don’t have enough dreams in their head to keep coming up with more.

Never get too satisfied by your success. When you hit a milestone, great. Go have a steak dinner. Pop a cork, if you must. But you expected to be here, right? So get back to work, and don’t waste too much time doing a touchdown dance. 

That’s what true winners do. They act like they’ve been in the end zone before.

4. If you don’t adapt, you will lose.

I can’t stress this enough: adapt, adapt, adapt.

Even when you have multiple revenue streams, you will still need to adapt your business to whatever obstacles present themselves. Long after Wilmar Industries became Interline Brands, and I made my exit, I started Crestar Capital, a tax lien business. However, over time the tax lien business had become flooded with institutional competition with lower costs of capital in a shrinking market.

I would need to adapt–and fast.

Instead of tunnel-visioning and trying to work twice as hard, I looked for ways to “work smart.” I knew that we had developed expertise in underwriting real estate and we had the infrastructure already in place, so I took that same team and formed a new company with a proposition that mitigated some of those risks, called LendingOne.

This is what I mean when I say you have to always be paying attention, always looking for the next move–because unfortunately, most entrepreneurs don’t realize it’s time to pivot and adjust until it’s too late.

5. You have to give it all you’ve got.

I can’t stress this enough: if you want to be successful, you have to go (as I say in my book) All In.  

My family stories and early business endeavors It wasn’t just a job. It was my life. I lived and breathed it 365 days a year. I was the first into the office and last to leave, and when I wasn’t traveling I ran home to have dinner with my family and then worked some more. I had a passion for what I was doing–and failure was not an option. 

Once you realize that there is no difference between “work hours” and “non-work hours,” that’s when you truly become an entrepreneur. 



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