My father had one rule.

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My father had one rule, and it ruined a lot of my good ideas.

You want to run a restaurant? Go work in a restaurant.

You want to open an indoor driving range? Go work at one. Figure out the economics before you fall in love with it.

He’d challenge an idea vigorously, then support my decision unconditionally. At nineteen, I found the first half unbearable.

It is the single most valuable thing anyone ever did for me.

Because he was forcing me to make it real instead of living in the dream version. And that habit of pressure-testing properly, then committing fully is the reason we eventually stopped building only other people’s castles and started partnering with others to stand up our own.

We have nine companies now. Legal. Preventative health. Construction. Coffee.

When we get it wrong, we feel it in our own pocket.

We have skin in the game.

The kind that makes our contribution to the chaotic world of dancing with AI real. And pressure-tested.

Something to take away here: Separate the challenge from the support.

Most people combine them, and it comes out as discouragement.

Challenge the thinking as hard as you can stand. Every assumption, every number, every “it’ll be fine.”

Then once the decision is made, back it completely and commit to executing.

Very rarely do we make the right decision. We make the decision and then make that decision right.

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Jason Shupp had me on the From There to Here podcast this week, and because his show does origin stories he took it all the way back:

The two years I spent pounding shingles for my uncle's business (formerly my grandfather’s), the referee years where I learned to come under fire, the PhD I left during the dissertation phase, and the day I watched my father put 32 rival business owners in one room and align them toward a common purpose in two days.

That was the day he became so much more than my dad.

The day I saw him for what he could do in a room. And what that skill set could mean for the world.

Full conversation in the podcast episode. Worth a listen on your drive to work.

• Listen on Apple podcast​

• Or listen on Spotify​

  
  

​Cheers,

Matt

PS. We still have some spots in our State of AI webinar on Monday at 4 PM AT. We act as your filter on what AI changes and use cases are worth your attention right now. Your first session is free, so zero risk to decide if it's worth it.