November 14th, 2018

Man oh man, the thoughts are flowing.

First employee with a solo founder at blank label. first non-technical, 7 at wildcard. first pm, 20th? at clarifai. some consulting with early stage co's.

There's never been a playbook or answer sheet. There's never been a 'this is how the VP used to run the team 3 years ago'. There's never been 'let's execute on what we know has been working the last two years'. There's never been, 'we're making X thing that's a $$ legacy product..but better'.

For good or bad, it has always been playing in the deep-end. The dark, murky, and ambiguous space of decision making and hopeful progress in 'the' right direction. If you don't take any action that day, nothing will happen. There's no existing customers, inbound interest, or serendipity that will consistently get you to a better spot. Sit there without talking to users, cold emailing potential clients, or asking a friend to make that introduction...and :crickets:...nothing. You have no tailwinds. Thus, each day you are forced to pick what task, what boulder, you want to start pushing up that hill.

Last night I was thinking of two things. Why do I have strong points of view and why can't I multi-task well?

(points of view on things within my domain — roughly, the business strategy, product development, and people buckets)

When I was young and super naive I would genuinely try to be

thoughtful about helping founders with their business. Here's an idea, here's a bug I found, here's an unprompted product tear-down that I did (take it or leave it), I can introduce you to XYZ.

The list goes on. The intent was always genuine and good, everyone appreciates a friend or internet stranger trying to help them win. The problem is...most of that is all logical. It's logical to spend an hour fixing that bug or a few hours trying to re-word the onboarding copy. It would be great to document each one of our internal processes. It makes sense. But if everything is logical and theoretically doable, what's actually worth doing? Of course I want that thing done, this thing not showing up like it is, contacts with others who can help on marketing, etc.

In the earliest stages the common thread is that you're forced to make decisions with imperfect information.

Each morning you are presented with a choice of playing whack-a-mole. With a finite amount of time, energy, and money, what will you and your team do that will actually move the needle for the business?

Given this clear and challenging daily reality, out of necessity, I think I've developed both an awareness and skill in asking the right questions about what the right work to do is.

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There have been many 'well run' companies that found the deadpool pretty quickly. From an operational and org perspective, you can have all the right processes in place but if you're not actually executing in the right direction, it's all for naught. It's the equivalent of a modern couple trying to keep up with the Joneses. You two appear to be a match (Kevin went to Trinity and Sarah went to Williams), you had a nice precious wedding, you shared all the right IG photos, you appear to be happy, you take the nice two vacations a year, you'll send out a nice holiday card of the fam in early December, etc.

All that is perfectly fine and good, if it's on a base of true love, trust, longterm sacrifice, personal alignment, etc. And if that's not the case because it's just the default path or you feel pressure to show that slice of life, it certainly feels 'good' in a fleeting moment to operate as if everything is fine but ultimately the fundamental essence of what makes this life and partnership thrive will never be addressed.

No one knows the right answer. I certainly don't. I just know that I'm wise enough now to stop, think aloud, and as myself and others - is this what we really need to be doing now?