I have a team whose livelihoods depend on me making good bets.
I’m not a theoretical builder. I’m a real business owner employing real humans in a time of massive uncertainty and disruption.
And since I was 13, I’ve pushed the boundaries of every piece of technology I’ve owned, starting with programming assembly language on my TI-86 calculator.
So when I talk about AI, it’s not theoretical. It’s not from the standpoint of a newscaster who can barely open Gmail on their phone.
It’s from the point of view of a builder who is constantly navigating implementing technology ethically while maintaining the livelihoods of a team that I love like family.
I talk about the intersection of ethics, philosophy, technology, and real-world leadership.
Because we need fewer opinions from those on the sidelines of these issues. And more from those who are actually building with it.
The bets I make with AI are the areas in which I think it has the greatest probability of improving my business while keeping my team employed.
The bets I don’t make are reflected in what I don’t do.
Hint: Not one of these posts is written by AI.
Do this with AI, and you are disrespecting your team
It’s never been easier to spin up an AI-generated, pseudo-scientific 25-page document and tell your team to memorize it.
But asking someone to study (and spend valuable time digesting) something that we spent very little time creating is the ultimate form of modern disrespect.
When we do that, we’re effectively saying “I don’t value your time, only my own.”
This is guaranteed to rub people the wrong way.
Steve Jobs was famous for extremely short emails. “Thx” “K”. Because previously, busy CEOs had to use extreme brevity to maximize their time.
And it’s not just me who feels this way. Even Paul Graham, co-founder of Y Combinator, admits that he checks out whenever he sees something was written by AI.
Just because ChatGPT can write a ten-page response to every email doesn’t mean that it’s more effective than “Thx.”
Failing in public.
The history of tech products is littered with failed product demos.
From Blue Screens of Death in front of thousands at a Microsoft event to the Cybertruck’s shatterproof glass easily shattering on stage, to robots falling down mid-routine and going berserk…
There’s no shortage of embarrassing failures out there.
But a lot of it comes down to expectations.
Deep tech is hard. Doing things that have never been done before is hard.
Creating a rocket that’s never existed before is inherently more likely to cause catastrophic damage than a new sneaker.
But we shouldn’t shy away from (or hide) this type of failure. Instead, we should embrace it.
It’s all part of the process. The failures represent a path towards success, and big victories often come shortly after (and because of) very public failures.
One quick way to improve your digital design now
In short, turn every “generic” decision into a specific choice.
All AI-generated interfaces look the same because they are all following a generic template. To be fair, what AI can do is far better than what the vast majority of humans can do when it comes to design.
But it’s not better than what the top tier of professionals can do.
The difference is in intentionality and meaning.
On Behance, you’ll see countless examples of amateur designers doing something flashy because it looks cool.
But it seldom has meaning other than the looks.
The best designers start from something that looks cool, and then keep pushing:
Ask “why” about every major design decision. Can we inject more meaning or significance into this decision?
Use natural language to talk about the design problem. What is the product called? What does it mean? What are we selling? Is there any way to put that meaning into this design decision?
How can a seemingly random design element tell a deeper story?
These explorations won’t always work out. But a design that has thought about these questions will always be better than one that is just cool for the sake of cool.
The Netflix show “Beef” and The Path to Happiness™
My brother has always talked about the path to happiness. Fundamentally, it’s about acknowledging that we can’t change the past, so which decisions/actions can we take right now that will lead to happiness?
But few of us ever put this into practice. The Netflix show Beef is about what happens when people can’t let go of a small slight and how it spirals into greater misery.
Someone bumped our car? Let it go. That’s the path to happiness.
But instead, so many of us believe that we have to get even. Vengeance is never a path to happiness.
Seneca said: “…the one who is indeed a great spirit and a true judge of his own worth takes no vengeance for an injury, because he just doesn’t feel it.”
On the contrary, a book written by a certain president once said, "When somebody screws you, screw them back in spades.”
Of course, it's up to us whether we want to read or listen to a book like that.
Or be that kind of leader.





