Something funny happened after I spent $3,000 fixing up my 2015 Range Rover Sport. A 2026 Range Rover Sport in the same black on black with 905 miles became available. It was the perfect setup, because buying a brand new car is a serious waste of money. When you’re the family’s financial provider, your goal is to retain and make more money, not incinerate it.
New, the car cost about $98,000 before tax. This one was selling used for $89,000. The previous owner had it for two months, decided he wanted the larger version, traded it in, and took a small bath.
I wanted the car. But I had just spent $3,000 fixing a coolant leak and an inoperable rear right window and door. So I shelved the idea and figured I’d reconsider after returning to Hawaii a month later.
When I got back, the car was still available, but the price had been lowered to $85,000. Now we’re talking. Still, I needed to drive my car for at least another week to confirm the coolant was truly no longer leaking before making an informed decision.
A week later, my car ran without a problem. And the car I wanted dropped to $80,000. Oh, the temptation as I struggled between cost, safety, and pleasure. But I resisted.
Then a week after that, the price dropped to $75,000. Sweet! Maybe I could walk in with a cashier’s check for $68,000 plus taxes and fees and they’d take it on the spot.
At the same time, I was staring down a $1,100 decision on two new 22″ front tires. So I rationalized that if I could haggle the newer car down far enough, it was worth buying, despite the $3,000 I had spent two months earlier.
Then It Was Gone
Just as I was about to email the salesperson who let me test drive the car, I noticed the listing link no longer worked. Noooooo.
I finally had liquidity thanks to newly distributed SpaceX and VCX shares sitting in my brokerage account. I was finally mentally ready to move on and waste a lot of money on a depreciating asset. After 10 years of driving and taking care of my car, I deserved it.
Alas, the salesperson confirmed it was no longer available. And after a full day of second guessing my second guessing, something unexpected happened.
I felt relieved.
There was now only one path. Spend $1,100 on two front tires and keep driving the car I already own and have meticulously maintained.
After all these years of disciplined saving and investing for a brighter future, the future made the decision for me to save and invest some more.
Investing During The Downturn
Back in 2022, the S&P 500 declined about 20% after a euphoric +18.4% in 2020 and +28.7% in 2021. The tech-heavy NASDAQ was even more violent, up +42.6% and +20.7% those same two years, then down -33.5% in 2022.
I tried to keep investing in public equities in 2022. But I would be lying if I said it was easy to invest the same percentage I had during the good times. My portfolio was tech heavy and getting beat up. When you’re losing lots of money, it’s natural to want to clutch whatever cash you have left.
That year, I was offered access to a tier 1 venture capital fund’s 2022 vintage through their friends and family round. I had invested in its 2018 vintage but somehow never got notified about the 2020 vintage, so I said yes.
It felt good to reduce my mental load and let someone else decide when to buy the dip. At the time I was preparing to market my WSJ bestseller, Buy This Not That, while taking care of my 2.5-year-old daughter who was home with us full-time.
So I committed $400,000, with $200,000 to the early stage fund and $200,000 to the growth stage fund. I estimated the VC would call about 25% of the capital the first year, or $100,000, which is more or less what happened.
Now I was tied to the mast. Even if I chickened out on buying the public equity dip, at least $100,000 was going to work. Taking part of the decision out of my hands felt wonderful, and worth the fees.
When Your Net Worth Becomes Your Self-Worth
Here’s the part nobody warns you about when you become the family’s provider and de facto investment manager. Your sense of self gets welded to a number you don’t entirely control.
When income is up and the portfolio is compounding, you feel like a good husband and a good father. When there’s a drawdown, or you hold something you should have sold, or you sell something that then triples, you don’t just lose money. You feel like you failed the people counting on you.
Nobody in the house says that, partly because they likely have no idea about all that’s going on with the investments. You say it to yourself, in the shower, going for a walk, while resting in the hot tub, quietly and sometimes, in great detail.
$100,000 Swings Before Breakfast
Now contrast my traditional venture capital investment in 2022 with my public venture capital investment in early 2023 through VCX.
I felt a similar calm when VCX was private and I could dollar-cost average in, quietly building exposure to AI names that are changing the world. Then it listed on the NYSE three years later, and suddenly I was riding out a lockup like a startup employee whose company just IPO’d. So many hopes and dreams, and none of the ability to act.
To decide what to do with my shares once the lockup expired, I spent hours modeling VCX’s estimated NAV for 2026, 2027, and 2028. Then I had to handicap the odds of retail mania returning as we edge closer to the IPO of the fund’s largest holding, Anthropic.
The temptation to take profits is high, given my entry point of between $10 and $18.97 a share. But my model says VCX can reach $60+ based on current data and expectations through year end. So even though I could sell 3,000 shares and buy myself a new Range Rover Sport after tax, I resist.
The wealth I’ve built to achieve Fat FIRE came from patience, discipline, and crunching the numbers. Unless new negative data emerges, I will not sell a single share under $60. And so I endure $100,000+ daily swings in one position alone, which quietly grinds away at me.
So I distract myself with more writing and pickleball. The goal is to push those swings into the background so I can focus on my actual life. Easier said than done. As the manager of our household finances, I never get to forget. Too much money is at stake.
Don’t Take Your Financial Provider For Granted
After 13 years of grinding in finance, I had forgotten what living pain-free felt like. I only remembered what it was like to wake up feeling normal about three months after I engineered my layoff.
Missing out on that car reminded me how nice it is to have a financial decision taken out of my hands. Because for the 11 years since my wife left her day job as well, I’ve been the primary one navigating the financial waters, making sure we don’t sink. And when the storms come, and new lives arrive to protect and feed, that weight can feel immense.
Is there any wonder why so many men and women are opting out of marriage and parenthood altogether? It’s hard enough to build financial security for yourself without The Bank of Mom & Dad. Add children and the pressure to provide climbs to a level that’s hard to explain until you’re in it.
I don’t blame any man for wanting to be a stay at home boyfriend or a stay at home husband. Who the heck doesn’t want to be provided for.
I realized back in 1999, when I graduated college, that there was nobody I could depend on for financial security. My parents were already thinking about retiring from their modest-paying government jobs. So the only solution was to save and invest aggressively enough to one day generate the passive income to break free.
If you have a partner who is the main or sole financial provider, please do not take them for granted. They are likely carrying more stress than you’re aware of, and possibly more than they’re aware of themselves.
As the household finances hopefully grows, the stress often grows with it, because more is at stake.
Close The Loops You Can
Here’s what I’ve come to understand about providing. The money is one thing, but the open loops are a constant strain. Every unresolved decision, every position you haven’t trimmed, every year of tuition you haven’t funded stays open in the background, quietly burning energy your family only experiences as you being a little distant at dinner.
So build decisions that close by themselves.
Automatic investing every month. A written target asset allocation. A capital call schedule from a fund that doesn’t care about you mood. A target price to buy or sell to help reduce emotion from your decision. The point of a rule isn’t precision. The point is to stop having the same argument with yourself every morning.
And if you’re not the provider in your household, the ask is simple. Ask them what they are worried about. Not the balance. The worry, and then let them know they’re doing a great job and how you can easily adapt to a lower standard of living, like a cheap and tiny house, if things go sour. They might finally open up, and feel lighter for it. You might even save their life.
Meanwhile, I’m still driving the same 2015 SUV, soon to have two fresh front tires. But if that black on black 2026 comes back at $70,000, we’re going to have a problem.
Reader Questions
If you’re the primary provider or the one managing your family’s investments, how do you disconnect your sense of self-worth to the rise and fall of your household’s net worth? Has anyone in your household ever asked you what you’re worried about?
What financial decisions have you deliberately taken out of your own hands, and did outsourcing them actually reduce your stress or just move it somewhere else?
Have you ever felt relieved to miss out on a big purchase you thought you wanted?
And for those of you who aren’t the provider, how do you support the person carrying the load?
Get A Free Financial Checkup
If you have over $100,000 in investable assets, take a moment to get a free financial checkup with Empower. Half the burden I described in this post comes from not knowing whether the plan actually holds together. The other half comes from knowing, but never saying it out loud to anybody.
A checkup solves for both. You get a second set of eyes on your asset allocation, your fees, and your retirement projections, from someone who isn’t emotionally attached to the positions you picked. I’ve run my own numbers through Empower’s free dashboard for years to track my net worth, x-ray my portfolio for hidden fees, and stress test my retirement plan against different return assumptions.
There is no cost or obligation to speak with a financial professional. Just don’t be surprised if they find a 401(k) fund quietly charging you 0.75% a year for the privilege of underperforming the index.
Empower is a Financial Samurai affiliate partner. The opinions expressed here are my own.
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