Want to Be an Entrepreneur? Its Hard, Really Hard, This Is What You Will Need.

Want to start a company? Think the only thing you need to be able to do is pitch to investors and build an app?

Unfortunately, that’s a common misperception these days. In reality, starting a company and seeing it through is much more about soft skills than having all the business acumen in the world. There are a lot of ways to be successful, here are some of the common things I see among successful entrepreneurs time and time again.

Mental toughness

To be an entrepreneur, you’ve got to be mentally tough. With every new day comes a new opportunity for you to get punched in the face. You’ll walk into your office and your website will be down or you’ll get a message over lunch that an employee just did something really stupid.

An old fashioned word for mental toughness is fortitude — “courage in pain or adversity.” Along with all the wins and triumphs, there’s a whole lot of pain and a whole lot of adversity that happens first.

Stoicism — the belief that happiness depends on accepting the present moment for what it is, not letting desire for pleasure or fear of pain determine choices — has become popular among successful entrepreneurs for this very reason. If you can make it through the tough days that come with founding a company, not just the good ones, then you’ll make it through it all. If you can’t handle the hardship, though, then success is going to be hard to come by.

Depression is a very real problem for entrepreneurs. Nearly one-third of entrepreneurs (compared with under 10% of Americans overall) fight depression at some point and for many it’s an ongoing struggle.

The reasons are many, but I think one of them is the new rockstar status of the startup world’s giants — the Simon Sineks, Gary Vaynerchuks, and Casey Neistats — and the difficulty some have when their entrepreneurial journey doesn’t follow the same trajectory.

There’s this perception that founding a company turns you into a superhuman with an epic YouTube channel and no problems. The reality is that wanna-be entrepreneurs looking in don’t see the real-life struggles that accompany the life.

Before Mark Zuckerberg and Jeff Bezos became household names, they experienced plenty of ups and downs with their companies. They worked hard and they overcame really tough challenges. But what young would-be entrepreneurs today see is the fame and the money and the power to change the world that accompanies building a world-class company.


Closely linked to mental toughness is tenacity. Entrepreneurs need to forget Einstein’s definition of insanity: doing something over and over again and expecting a different result. Instead of the definition of insanity, it’s the definition of an entrepreneur’s job. You have to keep making the cold calls, you have to keep reaching out and following up, you have to keep getting for an answer until it finally turns into

Tenacity is something most people have figured out at two years old but lose by the time they’re twenty. Kids get that “no” doesn’t mean , it just means , and they know if they keep asking long enough and loud enough, they’ll finally get the gummy bears or the new bike. But sometime before college, people buy into the notion that is final.

Here’s how most people think: “I called that one huge potential client and they said no. Guess I’ll just cross them off my list.”

Here’s how you need to think to win: “I called that one huge potential client and they said no. Cool. I follow up with them in three months.” And then you find the next big lead and chase them until they give you an answer.

When Chris and I started Penrod, he was the technical guy and I was the marketing guy. My job was to get the clients. I knew that I only needed a few customers to turn over to Chris so we could start making money. I heard “no” more times than I care to remember, but it only took a few responses to get us off our feet. Without a little bit of tenacity in making those cold calls and pitches, we wouldn’t be where we are today.

That also gets me to thinking about how many entrepreneurs fail right before their idea goes big. The original social network site, Sixdegrees.com, lasted for four years. The company actually had 100 employees and over three million users, so it wasn’t unsuccessful. But it shut down in 2001, right before social media became huge. A year later in 2002, Friendster was founded, Myspace followed in 2003, and the rest of the big players followed a few years later.

I don’t know exactly why Sixdegrees.com shut down, but what if they had stuck with it? They would have had a clear advantage — three million users before their competitors even had one. Even if their original concept wasn’t working for them, they could have made incremental changes until they landed on something good, and all with three million users.

And how many other entrepreneurs give up right before success strikes? If you have the ability to stick to it no matter how many times you hear “no,” you can be a legacy, not a bad example


Entrepreneurs have to take advantage of every opportunity that comes their way. Often founding a winning startup isn’t so much about the best idea, it’s about how you leverage your opportunities. It comes down to pay attention to what’s happening around you, focusing, and executing.

I used to play a lot of poker, and one skill I learned is something that I think every entrepreneur should know how to do: calculating implied odds. Each opportunity in business comes with it’s own set of risks and payoffs. In poker, if the payoff is 1000–1 and the odds are 50–1, then you jump on it. In a startup, you’ve got to know how to calculate the risks and the payoffs. If the winnings are potentially bigger than the risks, go for it. If not, say no.

I used my poker skills every day when I cofounded Penrod. It helped me evaluate opportunities so we could say “yes” to the right things and “no” to the wrong things. Along the way we were able to work with some incredible people, people who bet on Penrod early on and are now part of our success. We were able to turn that capital into a company that handles 60 to 100 projects at a time and we’re still growing.

But no matter how good you are at playing the odds and taking the right risks, sometimes you just get lucky. When that happens, have gratitude. Thank the people in your life who helped you get there and realize that it’s not all about you.

Ability to sell

Entrepreneurs can sell. This doesn’t mean they can run a successful sales cycle or make a good sales pitch. But they can sell themselves and their idea to their community, their network, and potential investors. Prove that you’re an expert in the field and that your idea has the potential to solve real world problems.

You’re also going to have to sell to potential employees. Somewhere along the line, you’re going to need to hire people to work alongside you. The problem is that you’re probably going to need to hire before you’ve hit it big, and it’s not easy to convince people to leave safe jobs for jobs at a startup whose future is still in question. You have to be able to convince them that, first of all, your company is worth it and secondly, that their hard work and effort is going to pan out and someday be worth it.

You’re going to have to talk. A lot. To the media, to your community. You have to get out there and present yourself to them, not by bragging or oversharing. Instead, share basic information about your company and let people ask questions. Sometimes they’ll take the bait and show interest — when that happens, be excited, share more, and ask them questions. And sometimes, they won’t care. That’s okay, too. Still continue to build a relationship with them, ask them questions about themselves, and learn about ways you could possibly help them in the future.

Knows the difference between activity and productivity

Many entrepreneurs are Type A people. They like to do, do, do. But superficial busyness and true productivity are not the same.

In Tim Ferriss says that this kind of busyness is actually a form of laziness. It’s easy to check tasks off a list and feel like you’ve accomplished something. But it’s hard to determine what kind of activities actually impact your mission.

You only have 24 hours in a day, and you’ve got to use those hours strategically. Take time to think and solve complex problems. Instead of doing every single task thrown your way, spend time contemplating what things you can do to make the biggest impact for your company and do those things.

Mindfulness is a powerful tool in determining what is just busy work and what is truly productive. At first, you may feel guilty about just sitting and thinking, but the minutes you spend journaling, meditating, or letting yourself be aware will have a direct influence on your success.

Do you have what it takes?

I wish I could tell all would-be entrepreneurs that this job is always easy and fun. It definitely has moments of greatness. But each day is made of little moments where computers sometimes crash, employees occasionally quit, and customers decide they want a cheaper option.

Sometimes it’s not even that earth-shattering. Sometimes it’s simple things that get you down like the loneliness or the mind-numbing tasks when you don’t have enough money to hire someone to do them for you.

But if you have the character it takes to make it through the earth-shattering and the mundane, then I can promise, the truly amazing moments will follow.

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