Founders must have been jealous with all the asset focused froth talk last week because the humans came out in full force right after to show us that asset performance doesn’t have diddly on founder performance. A wise man once said “the only difference between genius and insanity is that genius has its limits”. That man was Albert Einstein and we can safely file him in the genius category.

Another said “one must work and dare if one really wants to live”. Poignant words. That man cut off his own ear in a pyschotic episode and later took his own life. One of the greatest painters of all time that Vincent Van Gogh.

In order to change the world or at least make dents in big markets there is some founder chutzpah required. A level of extraordinary needed. Genius, maybe. Kookiness? Definitely. A plotted point further out on the limb but not too far whereby you’ll experience a painful fall.

First, let’s summarize a sampling of the recent ticker tape so you can catch up:

• Justin Zhu – the co-founder & CEO of Iterable has stepped down from his role after (reportedly) microdosing LSD during a meeting in 2019
• Travis Kalanick – the super pumped former CEO of Uber has been (reportedly) running CloudKitchens in a very similar way to Uber with the same core values, NDAs & more control, and a grueling schedule all contributing to employee departures
• Jason Fried & David Heinemeier Hansson – the co-founders of Basecamp have publicly struck political discussion from their workplace in a couple blog posts here and here with some relevant background here

In the coming months managers will be choosing to re-commit or bail from employers based upon new office & work guidelines as well as a myriad of other post pandemic factors. But that skips arguably the most important question any employee, managers, and leader who chooses where to spend much of their waking hours should ask (and then answer):

How kooky is the captain of your ship?

There is a lot to weigh when choosing an employer > compensation & equity, flexibility, network, visibility, mentorship, “give-a-shit-ness” come to mind off the cuff. Or you could try the kookiness scale. It’s very scientific:

         Not At All Kooky < ———————————————-*———————- > The Kookiest

                                                                                                                         ^ this feels like a sweet spot?

💊

• Microdosing on the weekends? Sure, why not!
• In a meeting? Ehh..

🔒

• Operating a stealth startup operation in order to mask competitive advantages? Strategically sound!
• Seemingly doing the same thing that got you booted from America’s most valuable startup of the 00’s but with more control this time around? Ehh…

🔴🔵

• Managing political discussion in a workplace? Distractions abound, there’s got to be some guardrails!
• Banning employees from discussing politics as a response to a controversial internal debate? Ehh…

The battle for how to best build a company and maintain its operations rages on. Are employees partners or resources?  Are employers scared of their employees? This week shows, if nothing else, the level of trust between investors, founders, and employees varies widely across the startup landscape. When it comes your time to re-commit or bail later this year we all hope, for each others sake, that you’re not out too far on the limb with Captain Kookiest, Founder & CEO.