Near the peak of my first relationship, my girlfriend and I wanted to start a food truck that sold fries with fun toppings. Our romance then descended to its unceremonious end, as our business would have, although it was an instructive experience for me I reflect on fondly from time to time.
A similar process repeated in my second relationship, except this time the market-disrupting idea was a cookie shop. What a spectacular IPO that would have been, assuming Jeff Bezos didn’t buy us out first.
It’s a small sample size, but half-baked, food-related business plans appear to be harbingers of relationship death for me. So if you overhear my wife and I tossing around a restaurant concept, get ready to choose sides in the divorce.
What annoys me is some of my buddies definitely would pick her, given their frequent unsolicited announcements of how much more they like her than me. Yet I don’t think I could poach any of her friends. I just haven’t made enough of an effort to ingratiate myself to the point where I could drive a wedge between them if it comes to that.
Fortunately for our marriage prospects, these frivolous thoughts of enterprise are dying down in my 30s. If I haven’t even tried to start a business by now, I am probably not the type to do it at all.
The realization is a bit sad, but I do have some thoughts counter to our generation’s fixation with entrepreneurship. We’ve been conditioned to see success as starting your own company, being your own boss, and never having to answer to the Man.
But everyone has to deal with some kind of boss in various situations. If you’re the owner of a company, maybe your boss is the big customer you have to keep to make payroll next month. Or distributors and vendors who need you less than you need them. Or the heavyweight in your ecosystem that can squash your business on a whim.
People have bosses outside of the org chart. I wouldn’t necessarily venture off into entrepreneurship for the sole purpose of being free from a boss. A great deal of autonomy is achievable as an employee of the right company.
I am going to cautiously cite Malcolm Gladwell here. Two of my wife’s friends illuminated what I had already sensed about everyone’s favorite cherry-picking pop social scientist. I read Outliers years ago and liked it enough to not be opposed to reading his other books. I haven’t gotten around to it though. Something doesn’t feel quite right about how he presents information and conclusions, and part of me wants to be a hater.
This sentiment crystallized when my wife’s friends informed me Gladwell seems to be listed on every Tinder profile as favorite author. That is so douchey I can’t take it.
I make a good honest effort to be a bro and intellectually elite at the same time. I appreciate the challenges and try to be better every day. These impostors are spoiling it for me. Gladwell artificially makes C students feel smart, which is nice for them but a disservice to the rest of society.
Tinder Bookworm Bro, I know it feels good to understand scholarly-like concepts and find them mildly interesting. But if you were behind the curve in 8th-grade social studies class, no one should have to listen to you talk about Gladwell. You laddered up beautifully in the evolution chain from tribal tattoos, and this should be commended but not inflated.
Anyway, in Outliers, Gladwell articulates the cleanest explanation for job satisfaction I’ve heard to date. I immediately committed it to memory and can readily recall it years later. He says meaningful work boils down to three things: autonomy, complexity (which I translate into always having something to learn), and connection between effort and reward.
The criteria works pretty well for me. And it explains the allure of entrepreneurship, which essentially maxes out all three attributes.
To get that max contract though, you have to be a max player (unless you’re negotiating with the Knicks). Self-awareness grows with age, and I feel less and less like a max player with each passing day.
Here’s an example of a max player. I was researching the ice cream phenomenon Halo Top for work, and the founder’s story captivated me. A former disillusioned lawyer, he created this low-calorie ice cream brand now reportedly flirting with a $2 billion acquisition price.
It took a double scoop of pint-sized testicles to get there. Here are some financial highlights:
- The founder started his business still owing $350,000 in law school loans.
- He and his business partner raised $500,000 from their personal network.
- At one point, he had to max out five credit cards for $150,000 to keep afloat.
- At another point, desperate for $35,000, he applied for a predatory loan at 24.9 percent. And got rejected. His business partner took it instead.
Anyone want to spot me a Benji so I can get some cool lights for my fry truck?
This is not me. No thank you. I just spent significant time over multiple days deciding on and executing a move from AT&T to Sprint. I am an expert at hyper-analyzing small decisions and rushing through big ones so I don’t have to think about them, only to second-guess myself to the brink of insanity.
I prefer to offload risk onto my employer rather than absorb escalating amounts. I prefer not to think about health insurance ever. I prefer the ability to clock out on some level, emotionally and task-wise.
There is a noteworthy dichotomy when it comes to days of the week for entrepreneurs versus employees. If you’re an employee, walking out of the office on a Friday at 5 p.m. feels like you just got laid 1000 times. It’s because no matter how hard you work and like your work, you don’t really care about the business.
But sometime around 5 p.m. Sunday, you start dreading Monday morning. It’s because no matter how hard you work and like your work, you don’t really care about the business.
For a budding entrepreneur, I imagine Sunday dread isn’t so low, but Friday elation isn’t so high.
I like my weekends. I like time to be detached from people and work. And Mondays never turn out to be as bad as the anticipation.
If I made $10 million, I would stop. That’s why I will never make $10 million. The people who wonder why anyone would keep working with that much in the bank don’t have the right makeup or motivation to get there in the first place.
Now, I’m not saying the successful entrepreneur has to make eight figures. If you can turn a hobby or passion into a decent living without spoiling the fun, I would say that’s worth more than $10 million.
There are different ways to play the game besides trying to be a max player. There are different ways to win. A little honesty about yourself, what you’re looking for, and the tradeoffs you’re not only willing but happy to accept can help you avoid putting all your chips into a fry truck.
An ice cream truck though… now that could work.
Writer’s note: If you spend any amount of your finite time reading the absurdities in this blog, we are either friends or highly compatible strangers. Thus I feel close enough to ask for your email address below. The only email you will ever get from me is one blog post per month for the rest of my life, until you click Unsubscribe. Thank you.