At a Glance:

• The different types of motivations  

• Why the assholes won’t win for much longer 

• Finding your “source” motivation 

Shifting Motivations

I usually pick up on a founder's motivations a few minutes after meeting them. It’s in their tone, posture, word choices, facial expressions, and emotional cues. 

If I’m coaching them, I shine a light on those drives to clear any blockages and go deeper. Why? I’m the turnaround guy: failure is highly likely if they don’t. Even if they do succeed, they will be miserable. Kind of a no-brainer. 

The deeper your motivations, the more success and joy you create. Sometimes, our desires develop with age, but my experience is that deepening is possible for all ages. 

Six months ago, I wrote about my friend Paul Lightfoot, whose career followed this model: from lawyer to startup CEO to running a team at Patagonia. He worked through every stage like a Plinko machine. At each experience, his fuel became stronger and cleaner. By the end, he was like the dilithium crystals in Star Trek: a regenerative energy source beyond space and time. His Eros. 

What’s Changing

“Don’t the assholes always win?”

I get this question a lot. Then I’ll ask them to name the assholes, and it’s always the same five people (you can probably guess….or DM me and I’ll give you the list, politicians not included). 

Yes, some high-profile leaders are at the upper end of the model. They’ve been able to hide behind better, faster technology, hard work, and “first mover advantages” for a while. 

But the tech stack is being commoditized. This means there’s less infrastructure “moat” to mask the leadership’s egoic drives. 

People don’t want to work with assholes. It’s only when they have no choice. As we confront a raging race to singularity, the winners will attract workers and customers by being more human, with AI supporting that humanity. 

I’ve worked with leaders whose motivations fall into these less-evolved categories. They’re not assholes. They have old trauma, and our system doesn’t help them work through it. They can either buffer themselves with kinder people or confront it. I’m proud to say all the founders I’ve worked with have the mettle to go “through it, not around it.” 

Finding Your Inexhaustible Fuel 

More to come in upcoming newsletters, and it will be covered in my next book, but here are some questions to tease out your deepest drives: 

• What has been the most meaningful experience of your life?

• When do you lose track of time?

• What did you obsess over when you were five?

• Is there an idea that has always haunted you?

• When did a work of art move you?

• What have been your most memorable dreams? 

• What would your 90-year-old self say about your motivations? 

• If your life were a movie, what’s it about?

• What would be your redemptive eulogy at the end of that movie? 

The new capitalism will point out the emperor’s egoic nudity. Channel your deepest fuel source, and you’ll beat the assholes…and enjoy the ride a lot more. 

With love,

Dave

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