Brutal lessons from my first entrepreneurial year

This is one of the brutal lessons that the entrepreneurial spirit left me: In the process of trying to be great, you will fail at almost everything.

Three years ago, I convinced one of my best friends, Drew Reggie, to quit his job and join my entrepreneurial crusade.

I had left my job in advertising just a few months earlier and was making a comfortable living as a freelance writer. He was about to finish his MBA and had clearly expressed his lack of enthusiasm for what the future held: a well-paying cubicle job at a large company.

“I want to build something,” he said. «You know, with employees. And with finances. “I don't want to be self-employed… I want to build a company”.

“Why don’t you want to take the leap with me, then?” I asked, dozens of times. “With the money we've saved, do you really think we won't come up with something in a year?”

Twelve months later we had a full-time team and a company that is successful beyond our wildest dreams. Digital Press, named during one of our many apartment balcony coffee conversations, has been our attempt to empower the smartest people in the world to share what they know.

We work with carefully selected CEOs, entrepreneurs, investors and venture capitalists (primarily at companies with revenues between $10 million and $300 million) to share their hard-earned knowledge online. None of the atrocious writing that most PR firms sell as insight. None of the advertising jargon that no one finds useful. Just the hard lessons learned and the personal stories of how these successful people learned them.

So, as a founder, I'd like to share some of the hard lessons I've learned over the last year, building Digital Press from the ground up.

I was very lucky to have a mentor before taking the entrepreneurial leap. My friend and Inc. columnist Ron Gibori taught me more about life and business than I could have learned on my own. But even after four years of tutoring, what I “knew” was still just theory.

I hadn't felt it yet.

Before taking the leap, Ron told me: “When everything becomes chaos, as a founder, you have to provide calm.”

I didn't understand what that meant until I started to feel the reality of building a company with other people's livelihoods at stake.

The entrepreneurial spirit has humbled me. And I find it humbling to many young founders, who often set out to change the world only to feel the weight of their aspirations when they realize it doesn't happen overnight.

Theory means nothing until you've been in the trenches. So, be passionate. Set out to do something big. But remember that you won't really know until you can say: “I have been there”.

After a year of entrepreneurship, I am surprised by how little the entrepreneurial world talks about the value of personal development.

I have done a lot in my 30 years of youth on this earth. I was a professional player in my adolescence. I was a bodybuilder in college. But nothing, and I mean nothing, has tested me like the entrepreneurial spirit.

Throughout the first year, I encountered moments where I would focus on the business, lose sight of myself, and then things in my life would fall apart. The personal relationships. Health. Emotional well-being. Everything suffered, because I felt that my business was my child, and that I would do anything to make it successful.

This is not healthy. And at times when you push too hard, you end up doing more harm than good.

I know I will be an entrepreneur for the rest of my life. There is no turning back. I have changed forever. But if there's one thing I hope to do for the business community along my journey, it's to start broader dialogues about the importance of personal development while building a business.

If you lose yourself in the process, your business will suffer.

I am fortunate to have other successful entrepreneurial leaders in my life who have passed on words of wisdom to me. But one of the most important (and you learn very quickly as a startup founder) is the value of cash.

I've always been frugal, but entrepreneurship made me see the money I had as much more than a “savings account.” Money began to have dozens of meanings: the ability to survive, the ability to innovate, the future of the company itself.

Before we came up with the idea for Digital Press, we were eating into our savings accounts. We helped each other cover our expenses. And by the time things clicked and we started building a profitable business, we both shared the exact same mindset: “Keep as much cash in the company as possible.”

This is one of those lessons that you hear about, and that you can even understand on a theoretical level, but it's not until you start adding employees, and you see your monthly payroll go up and up, that you really understand it.

Cash is your gas. You don't want to find yourself on the road with an empty tank.

A good problem to have is a problem anyway.

As an entrepreneur, one of the worst things you can do is chase too many rabbits at once. I have struggled with this in all aspects of my life, because when you are curious about the world you want to explore everything.

Part of what allows a business to flourish is simplicity. As another of my mentors, Aaron Webber, told me: “Simplicity is speed.”

When we try to build in too many directions at once, we fail. We overload ourselves with work. We get burned out, even discouraged.

But when we were able to focus on improving one or two things at a time, we flew.

This is a lesson that fundamentally changed my way of thinking, not only in business, but in all activities in life.

One thing at a time.

Since not many people seem to want to admit this, I guess I'll do it.

Entrepreneurship is lonely. No one will know how hard you work at what you do. No one will give you the recognition or the “pat on the back” that you think you deserve. No one will sit there, cheering you on, day after day. No one will take the blame when you screw up. No one will be able to tell you which address is right or wrong.

Entrepreneurship is lonely because, by definition, it means choosing your own path.

This took me a while to accept and emotionally address within myself. Not only will your efforts not be recognized by most of the people in your life (at least to the degree you would like), but at every turn you will feel like you are letting someone down.

If you're not letting your partner down because you've been working 17 hours straight, then you're letting your friend down by not calling him back, or you're letting your co-founder down by not responding to a problem quickly enough, or you're letting your employees down by not get them what they need… or you're letting yourself down by not being able to do it all.

This is one of the hardest and most brutal truths of entrepreneurship: In the process of trying to be great, you will fail at almost everything.

And you know what? That's fine too.

Because at the end of the day, all you can do is the best you can, and then get up the next day and try again, and again, and again.