5 Hard Lessons I Learned My First Year As A Startup Founder

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Almost a year ago, to date, I convinced one of my closest friends, Drew Reggie, to quit his job and join me on my entrepreneurship crusade. 

I had left my job in advertising just a few months prior, and was making a comfortable living as a freelance writer. He was about to finish getting his MBA, and verbally clear about his lack of excitement for what the future held: a high-paying cubicle job at a major company.

“I want to build something,” he said. “You know, with employees. And financials. I don’t want to freelance–I want to build a company.”

“Why won’t you take the leap with me, then?” I asked–dozens of times over. “With the money we’ve saved up, do you really think we won’t figure something out in a year?”

12 months later, and we’ve built a full-time team and successful company beyond our wildest dreams.

Digital Press, a name that came from one of many apartment-balcony-and-coffee conversations, was our attempt to empower more of the world’s smartest people to share what they know. We work exclusively with carefully selected CEOs, serial entrepreneurs, investors and venture capitalists (primarily at the helm of businesses doing $10M to $300M in revenue) to share their hard-earned insight with the Internet. None of that atrocious writing PR firms peddle as acumen. None of the ad-speak and jargon nobody finds helpful. Just the hard lessons learned–and the personal stories of how these successful people learned those lessons the hard way. 

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

Lesson #1: You know nothing (and that’s okay).

I was extremely, extremely fortunate to have had a mentor for years before taking the entrepreneurial leap. Friend and fellow Inc Columnist, Ron Gibori, taught me more about life and business than I could have ever asked to learn on my own. But even after 4 years of mentorship, I can still admit that what I “knew” was still just theory.

I hadn’t felt it yet.

Before I took the leap, he told me, “When everything turns to chaos, as the founder, you have to bring the calm.”

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

Entrepreneurship has humbled me. And I find it humbles a lot of young founders, who set off to change the world, only to feel the weight of their aspirations and realize it doesn’t happen overnight. 

All that theory means nothing until you’ve been in the trenches. So, be passionate. Set out to do something big. But remember, you won’t truly know until you can say, “I’ve been there.” 

Lesson #2: Entrepreneurship without personal development is a disaster.

I’ll be completely honest: a year into real entrepreneurship and I am astounded at how little the business world talks about the value of personal development.

I have done a lot in my 27 young years of being on this earth. I was a professional gamer as a teenager. I was a bodybuilder in college. But nothing, and I mean nothing, has tested me like entrepreneurship. It wears on you in ways I imagine fatherhood wears on a man.

All throughout the year, I found myself in moments where I would hyper-focus on the business, lose sight of myself, and then things in my life would crumble. Personal relationships. Health. Emotional well-being. Everything took a toll, all because I felt like my business was my child–and I would go whatever distance to see it succeed.

This is unhealthy. And the moments you push too hard, you end up causing more damage than good.

I know I will be an entrepreneur for the rest of my life. There’s no going back now. I am forever changed. But if there’s one thing I really hope to do for the entrepreneurial community along my journey, it’s start larger dialogues about the importance of personal development while building a business.

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

Lesson #3: Cash is your gasoline.

I feel extremely fortunate to have other successful business leaders in my life that have passed along words of wisdom. But one of the most important (and you learn this real fast as a startup founder) is the value of cash.

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

Without cash, your company dies. 

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

I feel like this is one of those lessons you hear, and can even understand on a theoretical level, but it’s not until you start adding employees and see your monthly payroll go up and up, that you truly understand. 

Cash is your gasoline. And you don’t want to find yourself on the open road on an empty tank.

Lesson #4: The burden of opportunity is a real burden.

A good problem to have–but a problem nonetheless.

As an entrepreneur, one of the worst things you can do is chase too many rabbits at once. I have struggled with this through every aspect of my life, because when you’re curious about the world you want to explore it all.

Part of what allows a business to flourish, especially in record time, is simplicity. As another mentor of mine, Aaron Webber, would tell me: “Simplicity is velocity.”

The moments we tried to build in too many directions at once, we failed. We overworked ourselves. We got burned out, even discouraged. 

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

This is a lesson that fundamentally changed how I think about, not just business, but every pursuit in life. 

One thing at a time. 

Lesson #5: Entrepreneurship is lonely.

Since not very many other people seem to want to admit this, I guess I will.

Entrepreneurship is lonely. Nobody will ever know how hard you work at what you do. Nobody will give you the acknowledgment or the “pat on the back” you feel you deserve. Nobody will sit there, cheering you on, day in and day out. Nobody else will take the fall when you mess up. Nobody will be able to tell you which direction is right or wrong. 

Entrepreneurship is lonely because, by definition, entrepreneurship means choosing to go “your own way.” 

This took me a while to really accept, and also emotionally address within myself. Not only will your efforts go unacknowledged by the vast majority of people in your life (at least, to the degree you’re expecting to be acknowledged), but at every step you are going to feel like you’re letting someone down.

If you aren’t letting your significant other down because you’ve been working for 17 straight hours, then you’re letting your friend down for not calling them back, and you’re letting your co-founder down by not responding to an issue fast enough, and you’re letting your employees down by not getting them what they need that day–and you’re letting yourself down for not being able to do it all.

This is one of the hardest, most brutal truths about entrepreneurship:

In the process of trying to be great, you will fail at almost everything. 

And do you know what? That’s okay.

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