The role of CEO is often described in gauzy, glowing terms espousing passion mingled with ambition that runs deep enough to change the world. All this noble ambition belies the uncomfortable reality that the inner world of a start-up CEO is often a constant state of conflicting realities that can distract from the mission at hand.
This list reflects my personal experience as the CEO of a social commerce startup. I can tell you – the dual reality can be disconcerting at first but after a while it gives you a certain edge that makes you tougher and smarter the longer you stay at it.
1) Your vision must be out there enough to generate investor interest but not so out there so as no one knows what you’re talking about. We’ve heard it from the pundits a lot – be different, don’t just iterate on another idea. Gotcha but then when you truly do go out on the limb – you may not get investor interest because you’ve too far out on that very limb they asked you climb out on.
2) Being 100% committed to do the best you can do but realizing that it might not be the best that can be done. As CEO, people want to believe you know more than you do – especially if you are chartering new territory. Unfortunately, you know that your best is probably not close to the best that can be done. You have to hope that it good enough to get by.
3) Truly believing in your vision yet living with the reality that the odds are definitely against you. I heard Brad Feld of Foundry Group remark recently that they get about 1,000 pitches a year but only invest in about a dozen ventures. So do the math. Your chances of getting funded are very small and even you do get funded – your chances of success are not in your favor. It’s a miracle anyone actually takes the plunge.
4) You are constantly recruiting even though can never afford most of the people you would love to hire. I learned never ever recruit when you urgently need to fill a job. That increases the chances for a bad hire because hiring in a moment of need won’t bring the best candidate forward – it will merely bring the most convenient one to the table. Instead, you should be recruiting ALL THE TIME. The trick is keeping the candidates you want on simmer until you are ready.
5) You must be a perennial optimist yet become exquisitely good at “productive worrying.” The grind of a startup requires a positive, upbeat attitude to get the team through the inevitable tough times. Yet, a Pollyanna attitude won’t get the job done to overcome the inevitable stumble that’s to come. For that eventuality, it best to be prepared with a Plan B and a Plan C too. In my case, I’m such a good worrier that my Plan B’s have Plan B’s (ya – I know – that’s extreme worrying).
6) You want to be fully transparent but realize there are some things you should NEVER EVER tell your VC. There is great serenity in knowing that you have been totally open and trustworthy in all your dealings with your people, your customers and your investors. Despite that – never confuse transparency with “true confessions” when dealing with investors. You need to convey confidence with a healthy dash of cautious optimism. Keep the deeper “what if’s” worries to yourself unless you have a specific ask of your VC.
7) People call you “Brilliant” and a “Visionary” but you feel like you are faking it. If you are a half articulate and just passionate enough – people will use the “B” or “V” word around you a lot. They hang on your every word waiting for the inevitable pearls of wisdom to trip off your tongue. Yet, often people confuse “Brilliance” with deep experience and a “Visionary” for someone who has a good grasp of history. Truth be told though, often you feel like you are just muddling through. That’s OK because if you admit you don’t know then others can step in to help. Otherwise the visionary, a.k.a. prophet must always have the answers. Not.
There you have it – the seven habits that are vital for any startup CEO. I guess ya’ need just a touch of crazy to pull it off.