What I Have Learned - Part 4 Why Am I So Lazy?

One of the hardest transitions I've ever had to make, and one I've seen several founders struggle with as well, is the move from Individual Contributor to Manager, especially to C-Suite executive.

Back in 2009 / 2010 I left a well-paying, super secure job as a research scientist and founded a consulting company with nothing. Very little credit, no savings, and no external investment, at the tail end of an economic crash.

Due to the generosity of several friends I managed to get a few sub-contracting jobs red-teaming and providing incident response. On Monday I would go to Starbucks, buy a bottled water and sit there all day sipping and working using their WIFI. Every day the rest of the week I would re-fil the bottle so it sort of looked like I had bought something. My dream was to partner with 3 of my best friends and get them on board full time working with me, so I worked incredibly hard to make enough money to bring the first one over.

I traveled southwest 2 or more weeks a month, stayed in lower end hotels, ate McDonalds, was often quintuple booked, and generally crushing it. It only took about a year or so to bring the other three guys on since each one would boost revenue enough to pay for the next.

My whole identity was wrapped up with selling, doing intense round the clock technical work, delivering value directly to the customers, and being in the trenches with my guys.

Flash forward a couple of years and we kept growing eventually getting up to 25 or so people. I had to focus more and more on CEO tasks and less on boots-on-the-ground technical work. I started to spend more time at dinners with big customers, in talks with VCs and private equity firms, working through 3-4 different acquisitions deals at the same time. And I was miserable.

I constantly had this sense that I was being lazy, letting my team down, and generally not getting any "real" work done. If I wasn't popping shells or bypassing a particularly tricky malware obfuscation technique or writing code, then I wasn't getting anything of value done. So I tried to do both and I did them poorly.

I didn't take into account how difficult and draining those CEO tasks actually are or how important they were to the company. Because I bootstrapped the company the way I did I built no hierarchy and internally thought of everyone as peers. I didn't establish strong lieutenants who could cover the areas I was weak and I didn't build a clear internal structure because I was so busy context switching between VC negotiations and reverse engineering.

Looking back I realize I had two good choices:

1. Embrace my new role, study it, and become as excellent at it as I had gotten at technical work. Leave the technical work to my team and trust them.
2. Place someone with those skills in the role of CEO and make myself Principle Consultant or something similar.

As the owner I would still have ability to make or influence major decisions but I would contribute to the company's success primarily from my core competency and passion and learn to trust my CEO.

In the end I did neither and spun off a product company instead, but that's a story for another time.

The Takeaway

Its important to plot out your personal progress as your company grows and understand that your work as a manager or executive has value, even if it doesn't feel the same as the work you have been doing. Realize that your identity has to evolve as you grow and likely won't stay static, so have a plan to help yourself through those transitions.

I have this rough bell curve in my mind where:

• In your 20s you are learning your skills and craft.
• In your 30s you are doing, ramping up the return on your investment in your 20s.
• In your 40s you are managing, boosting your organization by leveraging and enabling those in the two previous stages as a force multiplier.
• In your 50s you are mentoring and teaching.
• In your 60s you are enjoying and watching others on their journey.

And as usual I'm going to blow this whole approach up and do something totally counter to what I just said, which I will announce next week.

Thanks for listening,

A.