Entrepreneur ProTips

I've seen various posts from a diaspora of "entrepreneurs" that have resulted in nothing more than a cacophony of conflicting advice. Some of that advice was (in my opinion) bad. What better way to fix this than add my own!

I started by first business OmniTI†† in 1997 and then proceeded to found three other companies: Fontdeck†† , MessageSystems†† , and Circonus†† . I've been around a bit and understand the stresses of growing a company from nothing (no funding) as well as from taking rounds of financing and leveraging debt.

So... here's my advice. (hint: nothing to do with finance)

1. Understand how you cope with the stresses in your life.

You, like everyone else, have stresses and have to cope with them. As an entrepreneur of a growing business you are going to be exposed to some very foreign and harsh stresses. Understanding how you cope with stress and having practiced techniques for doing so is pretty much the only thing that will keep you focused, committed, and effective on your journey.

I've cycled through many things: movie nights, boring exercise, rock climbing, martial arts, and CrossFit. Worst: boring exercise (as I could still keep my mind in work). Best: martial arts (if I think about work, I literally get punched in the face).

2. Be prepared to work hard.

There’s a lot of talk about sleep deprivation and not enough talk about 80 hour weeks and 3am calls. The latter does not induce the former. Sleep deprivations is the dominion of those with bad time management skills and poor discipline… oh, and new parents. That said, being a new parent during the high stress parts of building a company puts a phenomenal amount of stress on both partners.

I've pulled my share of all-nighters. I've taken pride in being up over 72 hours straight solving critical production issues for clients. I've had insane and counter-productive sleep schedules. I've also known when to stop and take a break. I always tried to average more than 5 hours of sleep per night. It's important to know that everyone is different and, if you're one of those people who needs 8 hours, that should be your goal. Remember, 8 hours of sleep per night leaves 112 hours in the week, so an 80 hour work week is something that is possible and quite likely. Shout out to my wonderful and strong wife.

3. Be passionate.

There will be some hard times. Other days will leave you feeling like you had three meals of shit sandwiches. If you don’t have a damn good reason to pick yourself up tomorrow and reengage, you won’t. Passion is that reason. For many, passion is just the money and while that may work, I find that it can be demoralizing to have that be the whole picture… because success.

I'm not sure if every entrepreneur has moments of doubt: "Why am I doing this? Why do I care?" But, I sure have and continue to have them even 18 years later. For me, these doubts are usually spawned by a failed deal, a failed goal or a personal argument. I take a break to do something else that forces my mind away then come back.

4. Be able to define success.

It doesn’t need to be articulated painstakingly in a contract, but you need a firm and unshifting idea of what success looks like. There may be times where you need to reevaluate that definition, but the process should be deliberate and from the ground up each time. Shifting definitions allow you to cheat yourself and yield less personal reward.

For me, hitting goals is elation. And, truthfully, I can only handle so much of it. I've found it important to set very few, very hard goals. Every bullshit goal that was an easy target has only devalued future goals for me. I've learned that, on occasion, I'm retrospectively quite proud of some of my accomplishments that didn't hit targets. Some even took five years longer than I'd planned.

4. Take risks and don’t be afraid to fail.

When you do fail, don’t let yourself off the hook. Hold yourself accountable and don’t excuse a future failure of like kind. Be honest with your customers and your staff about your failures and your bad decisions. We're all human (I think) and transparency is a powerful trust builder.

I don't think I've been reckless. But if I was afraid to grow or change and that lead to risk aversion or indecision, I'd always end up with less that I deserve. When I'm betting on myself, I put my fucking chips on the table.

5. Be prepared to be wrong.

Humility is not required, but it sure fucking helps. You’re going to get a lot of shit wrong. In fact, I’d wager you’re going to get most of it wrong. Neither arrogance nor selective memory turns that learning experience into personal improvement. Awareness, introspection, and honesty do that and it’s dramatically easier to leverage those character traits with a big fat dose of humility.

I personally cherish every time someone on my team proves me wrong. It means I hired the right people. If I was wrong a significant amount of the time, I'd fail. This means, I'm almost always right (yes, I just said that). This also means I must surround myself with smart people with backbone that are capable of calling me out on my fuckups before it goes too far.

6. Lead.

A great entrepreneur, like a great leader, should inspire others into their vision. If you surround yourself with people to do your work and lighten your load, you can grow and be good. If you surround yourself with people who are more capable than you, impassion them with your vision and tie successful outcomes to their contributions, you will succeed and be great.

Leading is a hard thing to teach. I attempt to reflect on every action I do and ask myself if it will inspire those around me. Sadly, the answer to that is "no" more often than I'd like. Still, I try hard and those around me see that effort.

That's it: take a deep breath, calm down, work your ass off, appreciate your loved ones, take risks, be humble, and lead on to greatness.

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