Chris Sacca, AI Pressure to Do More, Faster, & Dialectic w/ CW&T: Time, Prototyping, and Collaboration

Listen & Read: Chris Sacca on Tim Ferriss (Redux) & Not Fade Away: A Short Life Well Lived

Chris Sacca is one of a kind. In an era when we’re starting to wonder what uniqueness means in a human sense, it’s hard to think of someone who is a more pure representation of it than him.

Chris used to spend a lot more time speaking publicly, and first went on Tim’s show ten(!) years ago—a year or so before I started working for him. I still remember listening to that episode. I was delighted to hear vintage Chris again in 2025. Chris is far from perfect and has been known to ruffle some feathers, but man, I couldn’t help but nod along while I listened and be inspired to live more of life at full blast.

Years ago, Chris recommended one of my now favorite books: Not Fade Away: a Short Life Well-Lived. Its the memoir of Peter Barton, a rambunctious, big-hearted, full-throttle, brilliant, beloved man who lived hard and fast. Peter’s father and grandfather both died at about 50 of heart disease, so when Peter was about 20 he decided he would have to live his life double-time, assuming a similar fate. In his late 40s, Peter had a healthy heart and had lived quite a life with lots still planned. Then he was diagnosed with cancer and died at 51. He and co-author Lawrence Shames took some of his final year to write the beautiful book about living and dying with grace.

I hope Chris won’t mind the comparison—and hope he has plenty of time left—but I realized that Chris is almost fifty. I think Peter would have a lot to admire about how Chris has lived his first fifty. I can only hope I am as alive as a leader, partner, dad, and person as Chris or Peter when I get there too.

Listen 🎧🎼: Dialectic Ep. 12: Che-Wei Wang and Taylor Levy (CW&T)

Che-Wei Wang and Taylor Levy are the founders of CW&T, a Brooklyn-based studio that creates tools, products, art, and esoteric objects that inspire me.

Their most recognizable products include the Pen Type-A, Pen Type-C (my favorite), Time Since Launch (a one-time-use, 100-year timekeeper), and Solid State Watch, a remix of the classic Casio F-91W. They won the 2022 Cooper Hewitt National Design Award for Product Design and the way they move between the wildly simple and practical to the abstract and thought-provoking is awesome.

Our conversation explores their fascination with time, their commitment to creating heirloom-quality objects in a disposable world, and how they've built a sustainable creative practice on their own terms. We discuss their prototyping-centered approach, the tension between digital and physical creation, and how they navigate collaboration as partners in life and work.

As someone who is obsessed with time, reveres collaboration, and spends too much of my time in digital space, I could not have enjoyed this conversation more. I hope you appreciate their thoughtfulness, wisdom, and earnest creativity too. Maybe you’ll even treat yourself to one of their creations.

All platforms: transcript, spotify, apple, youtube.

Read 📖📄: Jevons Paradox: A personal perspective - Tina He

Friend and Dialectic guest Tina He wrote about the growing feeling of a red queen effect many are noticing in response to the speeding up of everyone’s output these days, thanks to AI. And of course, what it means to be human. She nails it:

When technical execution becomes trivially easy, when anyone can spin up a startup, design a fashion line, or produce a film, the scarce resource becomes knowing what's worth doing in the first place. And what’s worth doing is typically deeply subjective.

Many have asked me recently, somewhat anxiously, about how I see the future of work unfold. I start asking them: close your eyes and think what amplifies your soul?

The answers I’ve gotten were about overcoming some really hard thing like finishing a marathon, experiencing a mind-blowing hospitality experience provided at a hole-in-the-wall bar, or an imperfect but emotionally-filled performance on Broadway. I thought of this Joan Didion quote on self respect:

“To do without self-respect, on the other hand, is to be an unwilling audience of one to an interminable documentary that details one's failings, both real and imagined, with fresh footage spliced in for every screening. (...) To live without self-respect is to lie awake some night, beyond the reach of warm milk, phenobarbital, and the sleeping hand on the coverlet, counting up the sins of commission and omission, the trusts betrayed, the promises subtly broken, the gifts irrevocably wasted through sloth or cowardice or carelessness. However long we postpone
it, we eventually lie down alone in that notoriously uncomfortable bed, the one we make ourselves. Whether or not we sleep in it depends, of course, on whether or not we respect ourselves."

Art collectors instinctively know this. The most successful shows aren't the ones displaying technical virtuosity but those that wrestle with distinctly human questions.

This may be the good news for those that didn’t dare to fully lean into what they love and want to do. What if the most game-optimal play in the new system is actually to become relentlessly, unapologetically you?

It’s not just “you can just do things,” but that “you can just be you, doing things.”