How a Black Leather Jacket Creates Ripples of Belief
Once upon a time… the Jensen Jacket was auctioned off to fund the next generation of artists, builders, and thinkers.
About a Jacket
"Jensen replied to my email. He offered to donate his black leather jacket for the charity auction… AND he said he would sign it!"
That was AZ, over the phone, talking giddily. I remember going quiet the way you do when news outruns your ability to react to it. Because this was an idea we had dreamed up more than a year earlier, around a lunch table at our office.
It had survived. To understand why that mattered so much to us, I have to back up.
For the last five years, we have run an annual charity poker tournament (Inflection Casino) each December to fund grants and fellowships for young minds to act on their passions and create inflection points in their lives (through Edge City). A number of our team members have experienced scarcity first-hand (e.g. Cyan growing up homeless and finding inflections through the generosity of others). We know how daunting it can feel to take the first leap and pursue “risky” opportunities without access to resources and “second belief.” We know the power of a permission-giving push, a “you should go do this” and how liberating access to $2,000 can be. The tournament was our small way of helping to create abundance for others, so more people could become confident first believers in themselves.
Two years ago, I added an auction to the fundraiser, with a simple curatorial rule: the prizes had to be magically weird and authentic expressions of people’s interests and higher purposes. A tour of Anduril with Palmer Luckey. A 1:1 coaching session on storytelling with Lenny. A trek to watch a Stoke Space launch. A living funeral (yes, a living funeral!) designed by yours truly. Then came an item that added a new layer of magic. Mark Zuckerberg (thanks to AZ) donated one of the first gold chains he ever bought and wore. It retailed at $400. It raised $40,000.
So we started asking a bigger question. What are the other great artifacts of Silicon Valley self-expression, the things people wear when they are most boldly and authentically themselves? Someone said it almost as a joke: "What about the Jacket?"
The 8-hour email reply
You know the one. There is exactly one black leather jacket in this industry that everyone can picture with their eyes closed.
Here is the part I want to be honest about, because it's the part everyone skips in stories like this. We sat on the idea for months. Not because we were busy. Because we were scared to ask. What if he said no? Or even worse, didn’t reply? Even people whose entire profession is belief will hesitate at the edge of a bold request, and the jacket felt like an impossible one. Then one Monday, right after our weekly planning meeting (we call it MAM, for Monday Afternoon Meeting), AZ stood up and ended the deliberation with five words:
"OK, I'll just email him."
She hit send at 1:14 PM in the afternoon. At 9:18 PM that same evening, her phone dinged. Eight hours, cold email to reply. And the reply, in its entirety, was seven words and a question mark:
"I can contribute a signed leather jacket?"
A few days later, an unassuming garment bag pulled up to Arielle's house in an Uber Courier. Yes, I think it was the most nerve-wracking 30 minutes of AZ’s year. Inside: the jacket. Black leather. Tom Ford. Signed in gold ink across the lining. She brought it to me at the office, held it out, and said, "You can keep this safe, right?" And so it spent 6 magical months nestled in my bedroom closet.
About Inflections (and Edge City)
An inflection point is the place on a curve where the bend reverses, where a trajectory that was flattening starts to climb. At the moment they happen, inflection points are almost invisible. Nobody throws a party at one. The force that causes an inflection point is usually small, and it works only because of when it arrives. A modest push, applied at exactly the right place on the curve, changes everything downstream. The same push, a year earlier or later, does nothing.
And in a human life, that force is rarely money alone. It comes in the form of permission and belief. Small sentences, delivered at the right moment, each one bending a trajectory. “You are on to something.” “You should go do this.” “You are ready.” That is the physics of belief.
Edge City is a society incubator. That sounds abstract until you see one: month-long popup villages where technologists, scientists, researchers, artists, and families live and build side by side, prototyping the institutions and ways of living the future will need. Ten gatherings across four continents so far. More than 12,000 participants. 30+ projects spun out into the world. It is what happens when you take the question what should the future feel like? and answer it with an experience instead of a white paper.
With the grantees and fellows at Edge Esmeralda (the Edge City in Healdsburg, CA)
Every dollar this jacket raises goes to support future Edge Cities, through Edge Institute, the 501(c)(3) behind them. The proceeds fund programs that back young, often overlooked builders before the rest of the world does. Inflection Grants: fast grants for creative builders under 25, money that lets someone build a project and, more importantly, build the conviction that they are the kind of person who builds projects. The Inflection Fellowship: a full-ride month living inside an Edge City village, surrounded by mentors and peers, chasing an idea that has no business plan and doesn't need one yet.
I know the “physics” of this personally. I'm the son of two Chinese immigrants, and I grew up lower-middle class. I was the first in my family to graduate from a four-year American university. From middle school through high school, +85% of my tuition was paid by the company where my dad worked. We would not have been able to afford the high school and college I got into without the help of this institution and it created more inflection points in my life, than I can track. That was a force, applied at exactly the right point on my curve. Nearly everything in my life that I'm proud of sits downstream of it.
The builder believes first. They have to, alone, before anyone else can see it. At Long Journey, we have a name for the person “who goes next”: the second believer. The second believer is the one who arrives while it's still just a curve that hasn't bent yet, and says: I see it too. The gold chain funded second belief. The jacket will fund more of it. That's the whole machine: one person's bold self-expression, converted at auction into dozens of well-timed pushes for people whose inflection points haven't happened yet.
About a Charity Auction
The Jensen Jacket auction is live right now at Sotheby's (July 7 to July 17). Someone remarkable will win a remarkable artifact, and their bid will fund inflection points for people they will never meet. That's one way to be a second believer, and it's a beautiful one.
But it is not the only way, and it's not even the most important one. So here is the actual invitation:
Think of one person you could second-believe in this week. Someone whose curve you can see bending before they can. The friend with the half-built project. The kid with the stretch application. The colleague eyeing a role they think is too big for them. Take a leap and back it with something real: a curious conversation, an intro, an hour of advice, a small check, words of encouragement. Do it with no expectation or attachment to the outcome. Give generously. See what happens.
And if you happen to know the kind of person who bids on artifacts of belief, tell them the story. There's a jacket at Sotheby's, looking for its next believer.
