An entrepreneur’s bold fashion choices lead to unexpected results
Business and finance reporter James Surowiecki once wrote, “To make a splash as a seer, you have to heed a simple rule: Fortune Favors the bold.” However, he goes on to write that the history of forecasting is littered with examples of experts who were acclaimed as visionary, only to disappoint. For example, Irving Fisher, a pioneer of economic forecasting declared that stocks had reached a “permanently high plateau,” just two weeks before the Crash of 1929. Or take Elaine Garzarelli, who, on the other hand, predicted the Crash of 1987, but completely missed the call in 2007, when she was “absolutely bullish” on the market.
So, thinking of all these predications, crashed economies, and faulting markets, I asked myself, “do any of these people know what the hell they’re talking about?” I realized that with every decision you make in life, you never know what is going to happen. Even when it comes to choosing socks.
I should back-up a little bit. For many years, I’ve noticed and experienced a great struggle in Silicon Valley and that struggle is fashion. Layer this, match that, and make sure your “threads are on trend,” and unlike NYC, make sure you don’t stand out. It’s a lot to navigate. Most struggle, including yours truly. So naturally, as a serial entrepreneur, I decided to go bold seeking to make a splash in my own personal fashion choices.
My first bold move was socks. The initial rules were easy to come by. The guidelines of coordinating the color of your socks with your pants seemed to be law of the land. Like Uber turning the world of transportation upside down, the harmonious standard between sock and pant color seemed to be a rule ready to be broken. That’s not to say everything was thought through, like the sock’s relationship with ill-fitting pleated pants or when wild was too wild, but the first-mover opportunity was there, and had to be leveraged.
The first pair I purchased were covered in an explosion of colorful shapes that had no rhyme or reason to their positioning or sizes. Imagine if Jackson Pollack was forced at gunpoint to paint geometric abstraction art but made it very clear with each stroke, he was not happy about it. (Don’t worry, he safely got away.) At the time, when adorning these vibrant colors around the bottom of my legs, I thought of myself as unique and bold, standing up to sock convention. I imagined waiting in a cafe for my coffee, checking my phone, my pant leg slightly rising, exposing a cacophony of color and self-expression. But more importantly, confidence. I imagined a fellow customer seeing my socks and thinking, “Man, that guy is so cool,” or “seeing this man confidently wear a pair of socks like that makes me want to finally get my life together.” Look, it’s my fantasy…
Like a disruptive start-up, the sock replaced the tie, and individuality, like the midriff, made its appearance. Fortune favors the bold! A crisp new pair of loud socks not only elevated every piece of clothing I was wearing, but it also elevated my energy, my spirit, my ego! Michael wearing a plain pair of socks was boring. He tired easily and kept changing the music to “Smooth Jazz playlist.” When café customers spotted his blank black socks, they frowned and questioned the point of chasing their dreams. But Michael, with a fresh pair of colorful socks that looked like a Rorschach test, was the life of the party. He had endless amounts of energy. His playlist was, “ROCK.” This forecast of wild socks paired with tame trousers was going to make a splash!
My maverick feeling, however, was short-lived. In just a few months, every other entrepreneur in Silicon Valley were wearing the same eye-squinting fabric around the ankles, like my Sand Hill Road friend, Rajeev Batra at Mayfield Capital, who was on my board at the time. Colorful socks were no different from blue jeans. Did I start the trend? Did I actually make the desired splash? I doubted it.
Sitting around the conference table, I noticed everyone’s pant legs rising, revealing their individual explosion of expression. I felt they were wearing it better than me, especially Rajeev. I knew it was time to pivot and find another open road. You win this round, Rajeev…
I decided to stay in the accessories realm and go to the opposite end of the body and try my fortunes with eyewear. Yes, eyewear. Its unique position on your face is equal to its importance as a metaphor. By that I mean, here in Silicon Valley, we use such words as “optics” or “lens” or “frame” regarding HR, branding, storylines, even Board decisions. If a board member is conflicted on a given subject, it is through that “lens” that other board members must see. If your company mandates Covid vaccinations, the topic turns to the “optics” of that decision – how the company is viewed. When we talk about a specific topic, we sometimes “frame” the boundaries around a discussion. “Let’s ‘frame’ that topic in the right light.”
But most important of all, your eyewear is the first thing people see in your zoom sessions, obviously more visible than anything below the belt. I mean, if people are seeing below the belt in zoom sessions, I feel like perhaps HR should get involved.
Shopping for eyewear is difficult and misleading. You’re basically on the hunt for a new identity, to go bold and be independent, so you get choosey about your brands. Therefore, I avoided Ray-Ban, Persol, Oakley, Oliver Peoples, Chanel, Ralph Lauren, Prada, Tiffany, Versace, Club Monaco, Anne Klein, even Alain Mikli. I also refused to use Lens Crafters, Pearle Vision, Sunglass Hut, Target Optical, and EyeMed Vision Care. That’s because all of them are owned or manufactured by a single firm, Luxottica. The individual aesthetic these brands represent is “Fake Bold!”
My first framed breakthrough caught my naked eyes the second I spotted them, Chrome Hearts. Made of sterling silver, hand-built in Japan, worn by hipsters from all over, the purchase of these what I believed to be “game changers” was certainly my attempt at going bold. Even tubers like the “eye guy” were giving these glasses their official nod. With exquisite detail in the nook and crannies of the frame, I stood out in this barren cultural landscape.
The acuity of detail in the frames, however, didn’t necessarily follow my presbyopia – from the Greek word meaning “old man’s eye” – or the more common terms hyperopia (farsightedness) and myopia (nearsightedness). In other words, there were execution issues that I could only ignore for so long.
I strutted around Silicon Valley wearing those bad boys like I not only owned the place, but I was renting it out to everybody in town. They were all tenants in the house Chrome Hearts built. Even in the café, my drink orders got a little more sophisticated. “You know what, let’s go with the ristretto, 10 shot, venti, with breve.”
But things started to waver a bit. A minute into any conversation without praise for my groundbreaking eyewear always spiraled me into confusion. Which led to doubt. The splash I thought I was making got smaller with each step. I was shouting my fashion forecast from the mountain top, but nobody could hear me. I knew it was time for a change.
The change was forced upon me when I had to finally adorn myself with specialized glasses for reading, driving, or using my laptop. It started at the café with some light squinting at the menu and ended with a full-on Don Quixote moment of practically running into a powerline at night. My space to make bold predictions and take risks was suddenly restricted. No wonder why eyeglasses are classified as medical devices! Inherent complexity or too many choices led me to progressives, which necessitated a large frame to accommodate multifocals. It was time to retire the Chrome Hearts
My next pair was like going from a sleek sports car to an earth mover. I was going bold, but not in the name of fashion. I was going bold in the name of functionality. I purchased the following made of horn (manufactured in Germany).
They had the structural integrity of a building frame and looked as such. I envisioned myself Michael Caine in the downbeat espionage movie The Ipcress File. Caine plays the role of Harry Palmer. Not only is Harry Palmer (Caine) insubordinate, but he wears heavy black glasses (revolutionary at the time).
I was suddenly reenergized with this new bold choice. I mean, Michael Cain wore them! You could say I was reaching for the stars! Like trying to come up with different ways to “frame” an inflexion point to make a start-up look like a unicorn, I tried different colors and shapes of eyewear: striated, blue, red, even multi-color frames. Creating different perspectives. Changing it up, so to speak. But as time passed, I watched the focal fashion trends of tomorrow pass by just out of reach. The medical device sitting right above my nose was nothing but a relic. No more splash from me. I wasn’t even in the pool. I was out in the parking lot, pushing my multifocals to the limit by trying to spot my car.
Bold moves lead to unexpected consequences. You can say you are worth a billion dollars, but the facts, in some way, must back up the story (the data room in SV parlance). In other words, I realized that more attention had to be made in relation to what I was wearing. I had to think a little bit about the combination of jeans, t-shirt, socks, and framed resplendence. You would have thought that Covid-inspired Lululemon-wear would decrease the decision making, but it didn’t. My Gold and Wood silk-blues coerced some degree of pre-Covid attire, which of course mandated two outfits – one for work, and the other for my one-minute inversions.
Sadly, even with all this effort, I eventually realized my uniqueness was in the eyes of the beholder. The distinction was blurred in the same way that the Hyperscalers – AWS, MS Azure, Google – blur the distinctions of independently owned companies. My days as a fashion seer had come to an end. Maybe occasionally, I’d take out an old pair of wild socks to relive the journey, but chasing the next fashion accessory trend was a thing of the past, or was it?
I realized that it’s not just about being right. Nor is it about being wrong. Like Venture Capitalists who learn from their mistakes, it’s about being ready. Sometimes you invest prematurely, other times not, but in the end, it all comes back, like a retro look. All we can do is try, whether it’s companies or socks. So, to all the entrepreneurs out there, my hats off to you.
Hey, wait a minute, maybe I’ll give hats a shot. Right?! Fortune favors the Bold!
