At least once every day I consider replacing myself with a ‘real’ CEO. Then I could just be the nerd in the cave, writing and programming and SERPing and such. But Portent’s my baby, so it’s hard to let go.
Here are the big 5 rules I’ve increasingly tried to work and live by. I am in no way suggesting I’ve succeeded. But if I look back at the best and worst moments of the last 16 years, these rules either helped, or could have:
Don’t model others
Before I started Portent, I worked for, in this order:
- A boss who came to work so wasted his eyes looked like red-rimmed bottomless pits.
- A 9th-Circuit judge who, while chomping on pretzels, would still manage to call me a fascist (?!) and point out how much my writing sucked. Seriously. That was every meeting.
- 3 bosses in a row who thought management improved with volume and obscenities.
Mix that together with my personality – hot-tempered, laced with swear words and generally negative – and I was the boss from hell at least 50% of the time.
Over the years, I think I’ve reduced it to 5-10%. But the most important lesson: Don’t model others just because they’re CEOs. Instead, take a look at leaders you truly respect, regardless of their roles, and emulate them. It works better.
Expect slings and arrows
Fortune can indeed be outrageous. If you’re expecting every day to be sweetness and light, you’d better reconsider.
You’ve heard the obvious issues: Making payroll, cash flow fears, irrational employees/clients/whatever. Those happen. The ones you probably won’t expect, though, are things like busted air conditioning pouring water into your office, the fired client driving down from Canada to accost you in your office, and of course the loss of phone service for five days (in 1997 – before VOIP).
Be ready for these kinds of things. Remember that, even a week later, you’ll probably be laughing about it.
Hire for chemistry
You can hire for skills, for smarts, or for chemistry. If you hire for skills, you get someone who can do the necessary work right away. Hire for smarts and you get someone who can learn a lot. Hire for chemistry, though, and you get someone who meshes your team, does a fantastic job in the long term and will probably be smart and skillful.
Of course I prefer all three. But when in doubt, I consider how a person will work with my existing team. They don’t have to ‘fit in’ – they can disrupt and make people really stop and think – but they do need to enhance the team.
Have a vision
“Make lots of money” does not count. It will not get you and your team through the slings and arrows and the thin times. You need a real vision of where you want your company to be in 5 years. You also need a real vision of what you want to offer the world.
This sounds really corny, I know. But something about what you do has to solve a problem and make your customer/client’s lives better. If you can’t do that, you will end up on the rocks. I guarantee it.
The first four years I ran Portent – 1995-1999 – I was trying to make a living. The company slowly morphed from a credit card-based, one-person part-time job in my spare room to having 2-3 employees. Then someone came along looking to buy us, and I signed without hesitation. That was a very poor decisions. I made it because, at the time, I didn’t really have a vision beyond “Make a living”. That kind of thinking leads to disastrous consequences.
Portent’s COO has been with the company for 10 years. He started here as an HTML jockey and designer. He became creative director. Then he became COO. He’s shy, so I won’t post photos or names. But he’s become a crucial part of the company through effort and opportunity.
If you have the good luck to hire someone truly spectacular, teach them. All the time. Don’t worry about whether they’re going to leave or not. Teach them everything you know until they say “Stop! My head’s exploding!” Pay them well. Send them to conferences. Encourage them to publish if they want to. Appreciate them. Challenge the hell out of them.
Talent in your company will change your business from “Ian’s company” to “Portent”. It brings real joy to your work, and it trickles down when the company gets to the point where you can’t mentor every single person.
And, if a great person leaves for a fantastic job somewhere else, the worst case is that you helped them get there. Take some pride in that. It still stings, but take pride anyway.
Mind your health
You will have weeks when you work 7 days, 15 hours a day. Depend on it.
Make sure you have a routine that can sustain you: Take breaks, chew gum, listen to music, whatever. Make sure your workspace is perfect. And make sure you can make up for that with friends, family and yourself when the squeeze is past.
Physical well-being is crucial. Mental well-being is even more important: Your personality drives your company. If you start to fall apart, your company will, too.
Take it personally
People will tell you business isn’t personal. That’s utter crap.
When it’s your business, it is personal. It had damned well better be, or you’re going to suck at it. You shouldn’t freak out and write psychotic blog posts about others (cough TechCrunch cough). But don’t beat yourself up if the setbacks affect you personally. And don’t deprive yourself of a little patting-on-the-back when things go well.
So yes, business is personal, at least for the CEO. Don’t avoid it. Embrace it.
Know your craft
I knew someone who tried to start a company making super-specialized bicycle wheels. Problem was, he didn’t know anything about wheels. So his idea of ‘super-specialized’ was a squirrel-chopping monstrosity that weighed so much most cars couldn’t have spun it. Of course he was planning to improve it, but his venture failed long before version two could get anywhere.
You cannot build a company around a craft – and everything’s a craft – if you’re not a craftsman. Lots of folks try it, but I have yet to see it go well.
Know your craft. If you’re running an internet marketing firm, you need these skills. Starting a burger joint? Know how to make a great burger. Building an online store? You must know your product and sourcing/selling.
You can’t make good hiring decisions, strategic decisions or anything else without that kind of specialized knowledge.
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