Sceptical Optimism Sceptical Optimism

Fatherhood and the Rise of the CEO

Fatherhood and the Rise of the CEO.

For longer than I can remember, I’ve done things my way.

“I go when I want, I talk to whom I want and generally I do what I want”

– Said no father or CEO EVER !!!

For longer than I can remember, I’ve operated as a Senior Engineer with my hands in many managerial and strategic pies. One might say, I enjoyed having my pie and eating it too.

After numerous fluctuations in the land of startups, in spring of 2019 I founded Startuplandia.

While having my pie and eating it too, I enjoyed refering to myself as CTO and avoided the phrase “CEO”. I think I had this mindset that I wanted to present myself to engineers as “one of them and not of management”.

Dec 23, 00:51 AM, the birth of my first child occurs, welcome to the world young Aurora!

My life with endless hours devoted to whatever reality I wanted comes crashing to a halt!

From December 2021 to May 2022, I’ve had my time compressed so intensly, I have no choice but to embrace the long ignored identity of CEO. On the positive side of things, being an organized CEO means doing less and getting more. On the less desireable side, my identity as a leader has accumulated some “power distance” from the people I most rely on to do amazing work. Thankfully, I’ve spent the last 3 years building rapport with many designers & engineers who so far seem happy to interact wiht me at CEO vice Senior Developer.

The Good

Think, Plan, Communicate, Calibrate

Almost everything useful that I do can be distilled to this cycle, notice there is no “do” -> As CEO, the closest I get to do is “communicate this plan to someone way better at doing than me”. The pro skill comes in Calibrate, the sooner, the smaller, the more precise the better, no blowups, no “get this done”, no “why is it so f’ing hard…”, just pure useful calibrations.

Recruiting, Product, Culture -> never change this prioritization stack

New talent and new projects, all forms of recruiting, diplomacy has an insane benefit to work ratio, an hour of useful conversation can lead to years of consistent revenue.

As CEO, I have 1 deliverable

From the CEO, Startuplandia requires a steady stream of financially/culturally appropriate projects to work on. The future belongs to the markets, Startuplandia operates as a broker to the talent markets of startups, Startuplandia wins when every designer or engineer has two or three alternative projects to work. (i’m not currently winning this battle)

One Kanban to rule them all

Trello, Asana, Whatever, only prioritized todos get done, the boards require constant refinement and organization. At Any moment in time, I can sit down, open my laptop or phone and have useful todo cards lined up to make use of small fractions of time.

Success comes from 20 minute note free conversations

Any topic or problem or opportunity, success can usually be found by having an emotionally real conversation with a decision maker, usually less than 20 minutes of real attention needs, no paperwork, no decks, no notes, just your thoughts, a few problem statements and a plan. As the leader on the other side probes your thinking, they will figure out if your actual plan holds water but they won’t need a diagram or a spreadsheet to have that conversation. They will probe for topics like “does this CEO have experience doing these things”, “does this CEO have a trustful rapport with me”, “will this CEO automagically take care of my problems” - Once a leader has a reasonably strong internal yes to all the above three questions, signed contracts and revenues materialize out of thin air.

The Bad

If you have people around you better than you and they aren’t working full capacity, CEO failure

Sometimes, I find myself trying to fix bugs or refactor code that well, there are at least 5 engineers who work with Startuplandia that are at least 3x more focused on engineering than I. I fail if I don’t maximize their time.

An 8 hour work day, in unstructured 10-45 minutes chunks at a time

Everyone says the father has no time, well that it isn’t true, we just don’t have long 6-10 hours stretches of UNINTERRUPTED time. I wake at 6am and by the time I go back to sleep at 9:30pm, I will have had numerous opportunites to work, those opportunities will just have been very unstable “oh you were focusing, i don’t care, clean me…” “oh you were focusing, I don’t care play with me..” and on than note please understand, I love my duties to the baby, I also love running a profitable business, happy path happens when everyones needs get reasonably met.

Any plan that exists without the support of trusted, experienced buyin will prolly result in serious turbulence

For the lone wolves out there, this one probably the hardest. Life gets more difficult as we become more developed. Getting buyin from people whom 1. trust and 2. have experience with the problems at hand, well that is the first part of building & executing on successfull plans.

The Ugly

There is no time to do anything, in fact the verb “doing” needs to be removed from CEO toolkit

As the CEO, I no longer have the luxure of “doing”. Anything that I need done, someone else needs to be doing, all I “do” is communicate a plan and help people calibrate, scary at first, liberating once well internalized. You hear a CEO say “this is hard work”, they don’t know how to be a CEO, CEO doesn’t work, CEO thinks, plans, communicates, calibrates.

Airplanes have warning indicators, CEO has no such luxury

Even in a total blackout an airplane that loses altitude, the pilots get a warning beep (or something?). Business problems, frequently while incubating, the CEO gets no warning, once the problem hatches, out rolls the dragon. So the CEO needs an excalibur, the will to use it, and the skill to find the problems during incubation stage.

All mistakes begin to cost non trivial amounts of money ->

April into May saw 16k of gross profit evaporate. Yep, I know I’ve made a mistake when I basically hand over money to some person, entity or problem

Ok, this post fully qualifies as an earful, that and I’ve no more momentum to write. Have a wonderful day!


John D


A Dream Team

We have traveled many miles.

We will help you build, scale, grow.