Suits, Ties and Tech Titans

It seemed to start with Steve Jobs. Jobs wore black turtlenecks when he was presenting new ideas to the Apple bureaucracy, as well as the general public. Many a medical expert has claimed that Mr. Jobs could have lived considerably longer, and possibly even enjoyed his billions for a few more years had he taken the right measures to address his cancer. But we’ve all failed in some respect, it is just that being a billionaire makes everyone examine your life with microscopes and make judgements. The world is full of Monday morning quarterbacks, yours truly included at least to some degree.

Theranos - Elizabeth Holmes
Elizabeth Holmes backstage at TechCrunch Disrupt San Francisco 2014


Then Elizabeth Holmes arrived on the scene and attempted to make the black turtleneck the laid-back Silicon Valley billionaire signature top. Not sure if they’ll let Holmes wear her black turtleneck in the joint where she’s going for an eleven year internment; those prison officers get picky about your wardrobe. Anyway, the track record of the casually clad billionaires hasn’t been making a very good first impression, or second. The nonchalant Silicon Valley billionaire vesture just doesn’t seem to make it, at least for me. Do they not sell suits there? Do they simply refuse to travel to some faraway Neolithic-Age city where there are still some tailors breathing?


If you still doubt this jaundiced critique , Google images of Warren Buffet, and you will see he wears suits and ties a lot. Let’s face it, Warren Buffet doesn’t have to do anything to impress us, he just wears what he feels treats us with respect. Say…respect would make a good title of a song; oh well, we’ll work on that later.


Then there was T-Shirt Zuckerberg, picking up where Steve Jobs left off, wearing T-Shirts convincing everyone that you can lead a billion-dollar company while wearing only T-shirts. It seems Zuckerberg has changed his style somewhat, as more of the recent pictures have him wearing suits and ties, especially since he has lost $71 billion in 2022, and he is trying to reframe his Facebook into Meta. I’m not sure how fast he’s moving or how much he’s been breaking things of late; (his motto used to be “move fast and break things”) it might be better for Zuckerberg (I don’t know if he has a nickname) to slow down before all the money vanishes like that critical English assignment that you didn’t back up on a hard drive and it vanished into cyberspace in the blink of an eye, to never return, just like all of the cryptocurrencies.

If you walk into a courtroom from off the street wearing jeans and a T-shirt, the court will consider you disrespectful


If you walk into a courtroom from off the street wearing jeans and a T-shirt, the court will consider you disrespectful. I don’t wear suits and ties because my purpose is to impress people; it shows respect and gravity.  Then we have a self-made cryptocurrency billionaire interviewing with the press. The reporter, wearing a respectable jacket and tie, and the billionaire, well, the way he was dressed, he sure didn’t look like a billionaire.

Sam Bankman-Fried

From the unkempt hair, the Bermuda shorts, the wrinkled T-shirt (reminiscent of Zuckerberg) Sam Bankman-Fried, aka SBF, interviewed as if he was so busy making billions that he didn’t have time to disentangle his hair or get fitted for a jacket and tie. Didn’t Howard Hughes (a billionaire from long ago, noted for his lack of personal hygiene) use that excuse as well?

Here’s a hint, SBF, when you have the kind of money you had and blew through, they will come by your residence in your beautiful gated community (just tell the guards they’re coming) and cut your hair of get you fitted for a suit. SBF is not the only billionaire to avoid personal hygiene and presentable apparel, but those of us who remember Howard Hughes are too few in number to be considered.

Hopefully, you saw a pattern here with all of these sloppily-dressed former titans of industry, with some exceptions. You aren’t turning the world around by dressing disrespectfully. You aren’t “freeing” anyone by ignoring tradition. When the cameras are rolling, make an effort to stop looking like a loser; in some cases, the loser you are. If you’re going to run a billion-dollar company into the ground, at minimum wear a suit and a tie; I will at least respect you a little bit.


Jeffrey Neil Jackson

Jeffrey Neil Jackson is an
Educator & Literary Mercenary

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