Do we get the Labor Day story confused?

This is Labor Day.  

You know, this is the day when we celebrate all that garbage about a fair wage for a good day’s work. The working man. The heart of the country. The backbone of the heartland. Images from steel mills and farms, from factories to small stores. We honor the heart and soul of our country. Pounding steel into high-rise buildings, building rockets to the moon and creating technologies that change the world.  

Yeah, maybe, but I wonder if sometimes, the story gets confused.  Founders aspire with passion, dedication and vision. Imagination unbounded. But turned backward, entrepreneurship as practiced in 2025 is a kaleidoscope, like that thing you put to your eye when you were a child and when you turned it the colors exploded.  

I know you tell yourself (and your investors) that you want to make the world a better place, to add value with a product that will inspire and create opportunities for growth and to raise all of society up with an aspiration for the better and good in our mutual lives.

Sure, but along the way, in those private moments, you know, tell me the truth, would it kill you if you got rich, really rich.  We don’t talk about it, we have integrity, but in the back of our minds, come on.  

So, on this Labor Day, allow me to share what lurks in the heart of darkness when the startup founder looks up into the azure sky.  Herewith a story from the Wall Street Journal by Gunjan Banerji, who writes:

Maxx Chewning sold his sour-candy business for $75 million a decade ago, but before the mandatory Rolex and the Birkin and the Ferrari, what he did first, was rent a private jet and take six friends to Vail on a Dassault Falcon 900. Price tag for the jaunt was $100,000.

“I had to get a private jet, so I could bring my dog.” This is why America is a great country.  

There are more “ultrahigh net worth” individuals than ever before, Banerji reports. You need $30 million to get into that club. There are about 200,000 of those guys. Next there are about 900,000 folks with 10M net worth, just scraping along the bottom. 

The billionaire class grew more than 50% between 2015 and 2024, according to the Wall Street Journal article. There are about 813 billionaires in America today. But after your IPO, well who knows. 

So, you ring the bell and you ask yourself, “What’s It All About, Alfie.” Well, the absolute next best, most desired thing is to fly private. And the private jet business is booming. There is a shortage of hangars. A shortage of pilots. And let’s not discuss air traffic controllers. This is clearly a startup opportunity.

Entrepreneur Tennille Holt retired in 2003, Banerji writes. She travels private with her Cavapoo, Hudson, who has his own Instagram account.  Labor Day, 2025, and a dog is a social media influencer. Only in America.

I’m not judgmental you understand. I believe in the American Dream. But when I am sitting in traffic, I do wonder from time to time if the homeless guy under the bridge or the nurse at the hospital is also dreaming. Not sure, maybe they are all good with a heavy dose of Ambien.

You gotta hang on and realize that you and me, we are living in an alternate universe, a Twilight Zone wonderland where monopoly money is being dished out like lines of coke. Pass go. Two hundred dollars. Hasn’t changed in 30 years.   

That $200 in 1935, when the Monopoly game was created, is the equivalent today of about $4,500. Parker Brothers needs an update feature that indexes for inflation.

OK, here comes the kicker.  

Kevin Hooks, writes Banerji, sold his pharmaceutical company and is a Flexjet customer, uses a Praetor 600 that seats nine. Sometimes he uses private helicopters to save time. Then he says, “Sometimes, I take a commercial plane. He recalls the time his son, then 4 years old, got on a Southwest Airlines flight and asked his dad, ‘Who are those other people on the plane’?”

Labor Day in America. Revel in it. After all, you don’t have to take off your shoes anymore.

Rule No. 795:  At least it wasn’t a middle seat.

Senturia is a serial entrepreneur who invests in startups. Please email ideas to neil@askturing.ai