Smoke, Ash, and Bootstraps: A Personal Reckoning with the Entrepreneurial Myth
The Monday Blueprint 3.03.25: The Late Evening Edition
Here are some financial resources for wildfire victims.
The frustrating part about a lot of book reviews: they pretend to be a critical examination but often end up promotions in disguise. What’s more interesting is when the reviewer uses the book(s) as their own launching pad for their own argument, which is kind of what’s happening in Robin Kaiser-Schatzlein’s The Cult of the Entrepreneur. But, I mean, who can resist a title like that?
Additionally, last week I did that whole Freakonomics Realtor comparison to the KKK, and that was a rather upsetting discovery and here again we are told Realtors are a bunch of losers, except way more elegantly. Take a look at this wonderful sentence:
“For every crisis initiated by ruling-class buffoonery or outright mendacity, an ideology that valorized the entrepreneur, the individual go-getter, the Johnny-on-the-spot, the hustler, the self-employed trickster God of Real Estate Financing would be a useful ideology for the winners of our social system.”
There is so much parallelism and repetition and rhythm built into that sentence structure that you almost don’t mind too much that you just suck because you’re poor. And also, more of Kaiser-Schatzlein’s magic when you realize in one single essay he covers not just 170 years of history, but exposes a cycle of the ruling class pushing entrepreneurship as a solution instead of fixing the system--because, well, the system is working just fine for those of us who are on the other side of the line.
From industrialization’s factory booms to jobs crashing, from Think and Grow Rich gurus to the New Deal’s unions rising—Reaganomics to dot-coms, side gigs, Uber drivers—the hustle myth repackaged and resold every time the markets crack. And I distinctly remember reading Success Magazine in the ‘80s, buying Tony Robbins in the ‘90s—entrepreneurialism wasn’t freedom, just a desperate survival strategy. Or worse, a desperate hope of survival.
Years ago, my dad was fired from his job. It was not the first time he had been let go. Or had walked flat out off a job—sometimes not even knowing what he was going to do the next day after quitting. He began C&S Lumber because it was either that or move to Michigan and work for somebody else who he would either quit on or be fired. In the end, the year my wife and I were married, and then also my sister and brother as well, he filed for bankruptcy. I stood in the garage with him. He sucked down a little brown cigarillo and I put away Camel Blues way faster than I should have been. We weren’t allowed to smoke inside. The bank was getting ready to take the house. He crushed out the cigarillo into the Maxwell House can we used for an ashtray. He said had nothing to give me for the wedding, and that he was scared because he had no idea what he was going to do the next day. That was the most vulnerable my father has ever been with me.
If Kaiser-Schatzlein’s essay had one shortcoming, it was that he didn’t fully address why people continue to embrace entrepreneurship even when that system of pull yourself up by your own bootstraps fails them. The appeal of entrepreneurship, he argues originates from America’s deeply embedded ideals: autonomy, self-reliance, and the believe in controlling one’s own fate. The values go all the way back to Jefferson’s agrarian ideal and are reinforced by Tony Robbins and ilk along with free-market policies. But his argument sticks to the level of history and ideology and doesn’t dig into what this looks like for people on the ground.
Because here I am, how many years later embracing the entrepreneurship ideology even though I have first hand experience of that system’s inherent failures. Do you want to buy, sell, or invest in real estate? Give me a call! No, seriously, give me a call.
In the last paragraph, we are left with a hell of an image—the idea that true freedom derives from the ability to quit bad jobs, form unions, create better more equitable systems, and carve out time away from work
It felt like there was going to be a call to action after that. A, hey reader, go do this one specific thing to help us get there. Or, maybe, I just felt like I wanted a call to action. Some simple solution to the problem.
Hey, I know last week I promised a crazy wild essay about Musk and what’s going on in Washington, but from the moment that I conceived that essay idea, by the time the end of last week so much went down I had to throw out my original draft and start fresh. Trust me, you’ll want to read this when it drops.
We too are implementing some logistical changes at the Coffee With Steve newsletter--adding yet another edition. The Saturday Rundown. But, also breaking the newsletter into sections that you will be able to subscribe to and unsubscribe from as you like. We’ll be uploading all the old Mailchimp editions to Substack as well. Every Saturday, The Rundown will deliver links to all the week's published content.
This way you can keep me in your inbox as much or as little as you want. And, if you do ever unsubscribe, I promise, we’ll still be friends.
Question of the Week
🚗 If Sal Paradise and Dean Moriarty were alive today, would they be digital nomads running a six-figure dropshipping business—or just broke Uber drivers chasing the algorithm?
STOCK MARKET REPORT?????
What stock market report?
Stuff happened, I’m pretty sure.
In other news, if you’re following along, I can walk again (well, sort of).