As a first-time CEO, I wasn't sure if I would scale to run IronPort long-term. But I wanted a legitimate shot at it.
The thorniest business problems will surface at the board meetings, and the different, sharp opinions help to better explore the poles of the arguments to make better decisions.
The best board members aren't elected by default. CEOs that set themselves up with their choice of board member - which means getting more than one term sheet and doing extensive reference checking - are better off.
Most companies don't have a good mechanism to give the CEO real, honest feedback.
I don't like sweating the details, and I'm pretty disorganized. To be a better leader, I need to stay on top of these shortcomings, and being reminded really helps.
For me, the brightest years at IronPort were without a doubt the darkest years at home.
Part of the magic of a startup is the fear of death. You have only so much money in the bank, and if you don't get to the right milestone before you run out, then the company goes under - it's over.
One of the stated values at IronPort was 'work/life balance,' but I wasn't living it. I was rarely home. And when I was home, well, let's just say I wasn't particularly helpful or cheery.
The experts typically know where the other best-in-the-world talents are currently working and can help you recruit them in with a credible intro.
It's really hard to break through the clutter and get the attention of the top investors, as they typically only look at deals that come in from a warm, credible referral. There's absolutely nothing more credible than getting an endorsement from a well-known subject matter expert who has already put their own money into your company.
When my co-founder and I first had the idea for IronPort, an email security company, we triangulated a list of the 20 most relevant people in email - former CEOs, open source technologists, investors and thought leaders.
All great pitches have a few things in common: the founder/team is wicked smart, the idea is big and a breakthrough, and the market is potentially enormous.
An approachable and authentic CEO is essential to fostering a high-performance, open communications culture.
Nothing helps make a leader more approachable than admitting your struggles, screw-ups and behind-the-scenes thinking on hard calls. If the leader makes this a priority, the whole company will be more open and methodical learning from failure.
While there's no substitute for real experience, I believe it helps to hear and share stories of resourcefulness in action - almost like case studies in school.
