8 rules for CEOs

Ian Lurie

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:

  1. A boss who came to work so wasted his eyes looked like red-rimmed bottomless pits.
  2. 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. 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 have 2-3 employees. Then someone came along looking to buy us, and I signed without hesitation. That was a very poor decision. 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.

Cultivate talent

Portent’s COO has been with the company for 10 years. He started here as an HTML jockey and designer. He became a 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 passed.
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, check out our Digital Marketing Stack. 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.

Related, recent, and random

Start call to action

See how Portent can help you own your piece of the web.

End call to action


  1. Ian,
    Excellent. I’m new to reading your stuff, and based on this post I know I’ll be reading a lot more!
    Seriously, though, still “boss from hell” 5-10% of the time? I find that hard to believe with your level of insight with the office relationship dynamic! Pat yourself on the back again, it’s probably more like 1-2% of the time. đŸ˜‰
    Great stuff.

  2. So true, all of it. I love how you mentioned that a potential employee has to fit and work well with the personalities of the team. This took me several years to figure out. If the skill are top notch you might think why not, perfect, hired. Only thing is once combined with the marketing team it could have been what was I thinking, this isn’t going to work, why did I hire this person. Being a team that can function working collaboratively together is priceless. Nice article Ian.

  3. Great post. Would add just two things to your list, based on our experience launching a ton of startups: 1) know (and admit) what you don’t know; and 2) recognize and pay for value (in terms of attracting a talented ecosystem of vendors and getting a great reputation within it.)

Comments are closed.

Close search overlay