Look at this photo. It is the absolute cliché of the “Silicon Valley Dream.”
The convertible. The California sun. The bright red jacket. The peace sign.
On Instagram, this looks like “Success.” It looks like an exit, or a closed Series A, or just a Tuesday in Palo Alto.
But I want to deconstruct this image. Because if you are building a company in 2022—amidst the Great Resignation and a market that can’t decide if it’s booming or crashing—you know that the reality behind the sunglasses is very different.
Here is what is actually happening in this picture.
1. The “Top Down” Vulnerability
Driving a convertible feels like freedom, but it is actually total exposure.
There is no roof. There is no steel cage around you.
This is exactly what being a Founder feels like right now. When you are the CEO, you are the windshield. You take the bugs, the wind, and the debris directly in the face.
If it rains (and in this market, the clouds are gathering), you are the first one to get wet.
My team is sitting in the back seat. They have protection. They have severance packages and equity vesting schedules. I have the steering wheel, sure—but I also have the elements. That smile? That’s me telling the passengers, “Don’t worry about the wind, just enjoy the ride.”
2. The Peacocking Strategy (Why I Wear Red)
I am an engineer by training. My natural state is “Dark Mode”—quiet focus, gray hoodies, invisible code.
So why am I wearing a bright, shiny red jacket in a sea of Patagonia vests?
Because capital is blind, and you have to signal it.
In the Valley, modesty is a vice. To raise funds and attract talent, you have to “Peacock.” You have to project an energy that is 10x higher than you actually feel.
I realized early on that the Founder is the company’s portable power plant.
- If I wear gray, the team sleeps.
- If I show up low-energy, the valuation drops.
- If I wear red, the team runs.
This jacket isn’t fashion. It’s a uniform. It’s a deliberate choice to amplify energy so the team can feed off it.
3. The Empty Seat (The Co-Pilot Paradox)
Notice the empty seat next to me.
In a sports car, that seat is reserved for a Co-Founder or a key partner.
I tell young entrepreneurs: Choosing who sits in that seat is more dangerous than choosing a spouse.
A marriage divorce is expensive. A Co-Founder divorce destroys the Cap Table, paralyzes decision-making, and can kill the company overnight.
I’d rather drive alone and navigate the map myself than fill that seat with the wrong person just to look less lonely. In 2022, hiring is hard, but firing a partner is impossible. Keep the seat empty until you find someone who knows how to read the map better than you do.
4. The Burnout Behind the Shades
Finally, the sunglasses.
Yes, it’s California, and the sun is bright. But that’s not the only reason I’m wearing them.
Behind these lenses, my eyes are red. Not from partying, but from 16 hours of strategic planning, negotiating with developers in different time zones, and trying to keep the culture intact while scaling remotely.
We post photos like this to signal “Victory.” But the reality of 2022 is that we are all tired. We are sprinting a marathon. The “Instagram Success” is a highlight reel; the reality is red eyes and adrenaline.
So, enjoy the view. The car is fast, the weather is great.
But don’t let the smile fool you—I’m gripping that steering wheel for dear life.
