I don't think there's a more difficult or stressful job than being an entrepreneur. Doctors, scientists, and engineers are all highly skilled professions involving a lot of pressure, but as to stress level the difference is that for the most part emotions don't enter to what those specialists do because they're trained in a systematic process that keeps surprises to a minimum. Being an entrepreneur, though, has an emotional component to it that no professor, instructor, mentor or amount of reading can prepare you for. Even if they tried to teach you, they couldn't. You have to live through the emotional roller coaster to experience it and learn to handle it. Remember that if it proves too hard to get through it's okay to pack your bags, pat yourself on the back for giving it a shot, and do something else. We're not all entrepreneurs.
There's a Massive Stress Pendulum
I can try and put into words the highs and lows you experience when running a startup, but I'll hardly be able to do it justice. One day you're on the top of the world — you've hired the person you dreamed about, you received your first term sheet, you pocketed your first revenue, etc. — and the next moment the world feels like it's crumbling down around you — traction is slowing, you have to fire an employee, revenue is slowing, employees are losing morale, your shipping deadlines are not being met, etc.
You'd think that if things are going well, the highs and lows would at least balance out, but, sadly, even the highs themselves are lows because of the way our industry judges success. You haven't made it until you've been acquired or IPO. Creating a private ten-person company consistently generating revenue is "not successful enough" in the eyes of most people. (Kudos to Dennis Crowley for accurately measuring success.)
Because of this you then question yourself as an entrepreneur: "Things are great now, but for how long?" Entrepreneurs constantly second-guess themselves while projecting a façade that they're doing just fine. It's a scary thought, because obviously the entrepreneur who feels that way is not doing fine and needs emotional support from their friends, family, and loved ones. We all do.
You NEED a Co-Founder to Offload Stress
I use to think that after having co-founded two successful startups I wouldn't need a co-founder for my next one. I was wrong. You can be the most seasoned operator, but at the end of the day you need another shoulder to lean on.
When you're a founder, everything is on your shoulders. The responsibility is on you and the founding team alone. Without a co-founder to share the emotional side of running the startup, then, you're left to bottle things up inside yourself. That's not healthy and will negatively affect you as a person, which in turn will carry over to negatively affect your startup. You'll take your stress out on your employees, the product, your loved ones, and your friends, all because you didn't have a co-founder who could relate 100% with you about what's going on. Don't do this alone.
Side note: When picking a co-founder, you want someone emotionally stable who is generally more of an optimist that a pessimist. If you, however, are an extreme optimist like I am, you may want someone that's a bit more even-keeled to bring you back down to earth when necessary. And this works both ways. If they're feeling in a rut, you can pull them out.
Why Investors Back Second Time Entrepreneurs
It's well known that investors back second time entrepreneurs because they've done it before and know the ins and outs of running a business. I think that while knowing the process is great, and obviously second time entrepreneurs do have this down, investors should account likewise for the mental and emotional toughness that second time entrepreneurs now have. As in sports, a team with playoff experience is in a greater position to beat a team who's seeing playoff action for the first time. Sports commentators call these teams "mentally and emotionally tough" because they can handle the stress better and don't get stage fright.
That being said, just being a second and third time entrepreneur doesn't mean that you won't go through the same same highs and lows as the first time entrepreneurs. It just means that you're slightly better equipped at handling them. Often times being slightly better is all that's needed for an entrepreneur.
If I was an investor — and in ten to twenty years I hope to be — I'd look at the emotional toughness of the entrepreneurs I was investing together with their ability to execute, the market for the product, and the idea. How do they perform under pressure when the world is coming down around their ears?
Get Back to the Basics
An investor friend that will remain anonymous once told me that when the going gets tough, you have to get back to the basics: "Eat. Sleep. Drink. Fuck."
He's right. As entrepreneurs, we get caught up in the dailiness of our startup and think that if we can just squeeze one more hour into the day, this'll somehow increase our success. After having done this for what seems like forever, I can tell you that one more hour a day will do more harm than good.
What matters is that you get back to the basics — as my friend so eloquently stated — and focus on relieving stress. The hour away from work can greatly increase your productivity when you come back to the office more relaxed and fresh.
Use that hour to escape. For me, the only time I can disconnect my mind from my startup is when I go to the gym to play squash and to relax after the match in the steam room. Even when I'm sleeping, I dream of my startup, but thankfully I was able to find my escape, and know that I can go there when I need to.
Another thing you can do is to take time off — something that I struggle to do. Go some place without Internet and without cell phone reception. Being away from it all may take a day to sink in, but when there's no way for you to connect then you'll mentally loosen up and be able to fully relax.
Get a grip on your emotions. It'll pay off in the end.