024 - Real Millionaire Shit
How I lost a small fortune but gained priceless wisdom
In February of 2021, after several enthusiastic DM exchanges, Zoom calls, and a promising in-person visit with the founders that concluded with my tagging along on a tour of prospective Santa Monica office space, I was offered a job with a Los Angeles-based mobile tech startup that seemed to be onto something big.
I was living in New York at the time, but had long fancied a move to California — that prophet on the burning shore where I’d be knock knocking on the golden door. In fact, I had been making preparations to move to LA in 2017 — even so far as giving up my Brooklyn apartment — when I booked the HQ Trivia hosting gig, requiring me to about face and report to their office/studio in Soho.
Here I was: on sabbatical from my independent Big City lifestyle, waiting out the doldrums of the pandemic back in my suburban childhood home, when this intriguing opportunity serendipitously presented itself. It was an offer to join the company full-time as Head of Studio Production, and it came with an attractive compensation package: a six-figure base salary with full health, vision, and dental benefits plus a 0.2% equity stake — a helluva lot more than the $0 I was making at the time.
Under advice from tech friends more experienced in startup employment contracts and the assumption that a counteroffer is standard practice in any negotiation process, I replied with a request for a higher equity percentage: 1%, anticipating we would meet at 0.5% and seal the deal. I was even willing to come down on salary in exchange for the increased share of equity as good-faith proof of my conviction in the mission.
This would prove to be a $10 million mistake.
Instead of countering my counter, they pulled their initial offer and replaced it with a six-month “consulting agreement,” sans benefits or equity. If all went well after six months, they said, we could revisit a full-time arrangement. Already entrenched in my cross-country-move mindset and excited by the potential of helping to build what could be a billion-dollar business, I signed on the dotted line and packed my bags for LAX.
Two months later, with budget for the studio I was tasked with building not yet approved and the entire “original programming” initiative absent from the product road map presented at all-hands, it was determined that I had been brought on too early. Rather than keeping me strung along in a lame duck role, they mercifully released me from my contract while generously paying me out for the full term. I spent the next four months relaxed and vaxxed, chilling by the pool, collecting unearned checks: the sunburnt embodiment of “White Boy Summer” (coincidentally coined by my nepo baby neighbor in Marina del Rey).
In January 2025, the company announced it had raised a Series E funding round, bringing their total investments to $750 million and ballooning their valuation to $5 billion. Guess I was right in thinking they were onto something big! Guess I was wrong in thinking they needed my help.
Four years have now passed since that offer was floated to me. Four years also happens to be the customary vesting schedule for employee equity shares, meaning had I accepted it, no questions asked, and stayed with the company through this month, I would have been able to exercise my options and claim my 0.2% ownership stake.
If you’re wondering what 0.2% of $5 billion works out to, please refer to the $10 million figure, above.
Now obviously this eye-popping number doesn’t take into account potential dilutions at each successive funding stage, or the fact that I would have had to remain employed for all four years — a rather unlikely scenario given my meager freelance tenure. Nevertheless I’ve found myself dwelling on these ten million dollars that got away — even going to far as to imagine them as ten million $1 dollar bills filling a 15 foot dumpster parked in my front yard that I could Scrooge McDuckly dive into from the roof — if only as a metaphorical device for pondering what is most important in life.
I thought about the $10 million last week as I slipped into a 102 degree hot bath at a downtown day spa. For forty bucks I was allowed access to their thermal pools, steam room, and sauna. For another fifty I was able to tack on a 30-minute back and neck massage. There is no easier, more affordable way to feel like a millionaire.
Think about how you react when someone tells you they’re getting a massage: “Oh I’m sorry, I didn’t realize I was friends with THE GREAT GATSBY. Enjoy your bodywork, MR. KRAFT.” But the truth is, massage is a fairly accessible experience — a mere $15 could get you a 10 minute foot rub. I now invite you to ask yourself: How many massages have I gotten in the last year? In the last ten years?
Now ask yourself: How many tattoos do I have?
If you have more tattoos than you’ve had massages, YOU’RE DOING IT WRONG.
I don’t have any tattoos, but I’ve had, like, 40 massages. That may not sound like a lot, but — two massages a year for 20 years? That’s pretty good.
When I see people tatted up head to toe, all I can think is how much money they spent to permanently and painfully stain their skin, and how those funds might have been better deployed, say, on utter relaxation. A comprehensive, expansive tattoo design can easily cost five-figures to complete. For the same price of a full body suit, one could enjoy a full-body massage twice a week for four years.
And I’m talking hot stone massage: perfectly round stones popped in the microwave on high for 16 minutes, piping hot and electromagnetically-irradiated, sliding up and down your naked, oiled back. No matter what level of “completion” one reaches, getting a massage is inherently nice.1
Getting a tattoo, on the other hand, seems inherently distressing. If prepared to spend the same amount of money to lie still for the same amount of time, and given the choice of either a) being anointed with lotions and tenderly caressed and stroked to the soothing soundscapes of trickling water, chirping birds and soft, sustained piano; or b) being stabbed ten thousand tiny times to the screeching mechanical drone of the tattoo gun, the decibel of which you grow increasingly grateful for how it drowns out the escalating volume of regret at deciding on a string of Chinese characters purely based on their aesthetic appeal versus their indigenous definition (“toilet demon”), it BOGGLES MY MIND how many people happily choose the latter.
I won’t get tattoos, because clearly, I don’t get tattoos. You know another spot where you can display visual representations of people, places, and things that are most deeply, profoundly, and personally unique to you and you alone? Your phone. The wallpaper on your phone. Just as many people will see it, and you can change it at any time, depending on how you’re feeling in that particular moment. That way, you don’t have to have the name of the woman who took the kids and left you for the Tae Bo instructor inked across your forehead for the rest of your days.
All that being said, I’m not sure I’m doing massages right. First of all, you’re supposed to be loudly and obnoxiously exhaling the entire time, right? And aren’t you also encouraged to shout things like, “Oh yeah yeah yeah, that’s it, right there. Yep yep yep yep ahhhh yesssss that’s the spot” the entire time?
If I’m being honest, my massage history is spotty at best, riddled with as many groans of pain as moans of pleasure. Of my 40 lifetime massages, maybe 20 were actually pleasant? 50-50 is not a respectable ratio for massage satisfaction. I feel like my winning percentage for enjoyable massages should be closer to 100%. After all, IT’S A MASSAGE.
I would go one step further to say it should be ILLEGAL to render malignant massage services. There was no more glaring oversight by our Founding Fathers than failing to include even a single clause in the Bill of Rights relating to the guarantee of a non-agonizing massage. But even then, what recourse for international incidents? My ex and I got massages in Paris last year. I walked into the place perfectly fine; I walked out with a noticeable limp. I handed this guy a hundred euro for a herniated disc. I paid 100€ PLUS TIP to fuck up my back for two weeks.
How about when they tell you, “Oh you’re so tight, you’re so tight, you have so much tension…” Really? You felt I was tight? Maybe that’s because THAT WAS MY BONE. You were on my bone for most of the time. Maybe I was so TIGHT because my BONES are HARD with TENSION. I thought you’re supposed to massage the muscle, not the marrow.
To return to the point I was trying to make earlier…
Slumped in that delightfully scalding water, every cell in my body vibrating in rhythm with the buzzing compound molecules of hydrogen and oxygen that immersed me, I asked myself a very serious question: what would I be doing differently with $10 million? Could $10 million buy me better water? Wetter water? Could $10 million somehow enhance the full-bodied feeling of unadulterated bliss and total contentment that I was experiencing in that present moment?
This line of self-interrogation led to a beautiful realization: I don’t need $10 million. What more do I need that I don’t already have? How could I possibly be better off with $10 million when I was already living my best life without it?
Now $5 million, that would be nice. Could just park that in a money market account earning 4.2% APY and live off the interest. Yep, $5 million. That’s all anyone really needs.
I can only assume “Happy Endings” are real, because football players keep getting in trouble for them, but I have no first-hand experience to prove their existence. You heard me: I’ve never had a rub and tug. Not that I am necessarily opposed to the concept, if provided consensually — to be clear, I am very much opposed to the disturbing human trafficking element alleged to be so deeply entwined within the industry — it’s simply that I’ve never been offered! Not even once! What’s up with that? Is my dick that shitty? Is there a secret codeword I’m not aware of? Am I supposed to book the appointment under the name “Jack Mehoff” or “Wink Wink Martindale”? What am I missing???