I wanted to wait until I could get a few Product-related things published before I posted something like this, but I recently stumbled upon a video from food youtuber Internet Shaquille about sports betting that really got me thinking. (You can watch it here if you’re curious.) The gist is that sports betting is surprisingly detached from sports knowledge, relying heavily on stats and probability. More alarmingly, it’s a largely unregulated space where platforms can ban you for being too good. If you’re active on one of those platforms for more than a few weeks, it’s because you’re likely to lose money than win anything of significance.
Shaq’s concern is that this is being pushed on people so effectively that we may not be aware of the societal problem until it’s too late. This reminded me of tech (and I mean “tech” broadly, from engineering teams at United Airlines to Instagram), where individuals often have little chance against the strategies of large companies. Think about dynamic pricing or customer retargeting – complex topics with potential regulatory pushback. They’re also things I’m not fully qualified to talk about.
But today, I want to focus on something different: the human side of what we do with our money after we’ve earned it. If you’re reading this, you’re likely in your peak earning years (25-50), but that doesn’t always mean smooth sailing. Perhaps you’re stuck in a job that pays the bills but slowly drains your soul. Or maybe you’re facing the uncertainty of unemployment, navigating the stress of job searching and financial insecurity.
Forget the usual platitudes (”time in the market vs timing the market,” “index funds, rest and vest,” etc.). Let’s really dig into the motivations behind how people spend and “invest” their money – especially when the stakes feel higher than ever.
Whether it’s you or friends you’re seeing dive into sports betting, crypto, or individual stocks, or you’re watching the next generation grapple with these choices, it’s our money, and in times like these, it’s especially important to talk about it. After all, wealth is like good thyme... always well spent! (my one and only forced dad joke, I promise)
I see three main categories, though there are definitely more:
1. Lack of Market Context: Bull Markets Make Fools of Us All
There’s nothing like the feeling of refreshing your portfolio and seeing you’re $5,000 richer than when you went to sleep. That optimism is intoxicating.
This next section may seem obvious to you, as it did to me, but the truth is, when you’re in it, it’s almost impossible to pull yourself out. We know the following in theory, but it’s worth exploring anyways.
If you’re under 30, the 2008 Financial Crisis is probably just a chapter in a history book. And if you discovered crypto during the pandemic boom, you haven’t truly felt the sting of a crypto winter. (Unless you’re actively building in the Liquidity, Treasury, Wallet, Brokerage, or Transactions space - if so, then you know more about crypto, and most definitely more than I know about crypto.)
I know – everyone says “just DCA, set it, and forget it.” It sounds so simple, right? But speaking from experience, there’s nothing like the feeling of refreshing your portfolio and seeing you’re $5,000 richer than when you went to sleep. The optimism is intoxicating – you start thinking, “I’ll be another $2,000 richer by tomorrow!” No one is immune from the sports betting tendencies we talked about.
That’s the bull market talking.
I’ve been through four cycles since 2007, and each one has taught me a somewhat painful lesson. Bear markets are brutal and watching it happen to someone else on the news will give you no real context. You don’t know when they’ll start, how long they’ll last, or if you’re going to be the genius “buying the dip” or the idiot who didn’t know when to quit. Volatility only helps if you’re making controlled, almost algorithmic bets over a long timeframe (and maybe with a tiny bit of leverage, but that’s a dangerous game). Otherwise, it just crushes your mood (at best) or your net worth (at worst).
2. Building Antifragility: Navigating a World of Disorder
Our risk tolerance changes as we go through life. What seems like a great idea as a young, single adult just starting out in a tech job with nothing too lose might not be so appealing when you have a partner, a pet, or children to think about. Likewise, losing a chunk of your portfolio after having built so much can shake your confidence for years.
They’re convinced you’re one lucky trade away from early retirement. It’s like thinking you can win a Michelin star by microwaving a frozen dinner.
But enough people I know in life have successfully side-stepped the rat race with a crazy amount of discipline. Nassim Taleb calls this “Antifragility” – the ability to not only withstand external shocks, but to benefit from them. It’s about avoiding trends, not blindly accumulating risk, and being ready for asymmetric opportunities. It’s often a boring strategy of doing business as usual until it’s time to act decisively.
Think of it like this: one group of investors opens five trendy poke bowl restaurants, taking on debt, a large staff, and perhaps franchise royalty payments. They’re riding the wave of the latest food craze. But as demand slows down...they’re forced to close - immediately and violently. Another family runs a local, beloved Ethiopian restaurant, serving classic dishes passed down through generations. They own their building, have a loyal customer base, and weather every storm because they’re not chasing the latest fad.
But they don’t just survive those storms – they thrive. When a new wave of health-conscious customers arrives, they highlight the naturally vegan and gluten-free options in their cuisine. During an economic downturn, they offer discounts to community workers becoming an even more integral part of the neighborhood. And when a nearby restaurant struggles, they conservatively acquire the failing restaurant’s assets at a discounted price, expanding their capacity and reach without taking on excessive risk.
Now, I’m not suggesting you go out and start buying restaurants (unless you have a passion for injera!). The point is that adopting this mindset of measured, opportunistic growth can be beneficial in other areas of your life. It’s about building a foundation that can withstand shocks and then strategically capitalizing on opportunities when they arise.
3. The Empathy Gap: Your Comfort Number Isn’t Everyone Else’s
You might be tempted to skip this section, thinking, “I already know what’s best for me.” But before you do, consider this: in our increasingly isolated world, it’s easy to lose sight of the diverse financial realities people face at different stages of life. With fewer “third spaces” to connect and share experiences, we often struggle to understand perspectives beyond our own.
Those who achieve financial success often unintentionally impose their worldview on others, sometimes for better, but often for worse.
So, resist the urge to skim. Invest the next few minutes in stepping into someone else’s shoes – even if they seem radically different from yours. It might just challenge your assumptions and help you adjust your own risk profile. These are all friends of mine, but the age and titles have been slightly adjusted to respect their right to privacy so you can’t reverse engineer them from my LinkedIn profile.
We all clutch our pearls (or wallets) at different numbers – $50k, $500k, $2 million. But the moment that happens, a switch flips, and it’s less about aggressive growth and more about preservation. And while there’s nothing wrong with that, it’s important to remember that your “comfort number” is just that – yours.
But here’s the catch: those who achieve financial success often unintentionally impose their worldview on others, sometimes for better, but often for worse. This leaves those in the middle without a clear gauge of whether they’re on the right track.
So, before we dive into specific scenarios, let’s just take a breath and acknowledge that we all have blind spots. Our own experiences inevitably shape how we see the world, and that includes our financial perspectives.
Scenario Breakdown
23, Fresh Out of School, Less Than $50k Invested: They’re living on instant ramen and dreams, glued to r/wallstreetbets, convinced they’re one lucky trade away from early retirement. It’s like thinking you can win a Michelin star by microwaving a frozen dinner. Not happening, boss.
Financial Priority: High-risk, high-reward investments with the goal of quick gains (and paying off those student loans...eventually).
Fragility: Highly vulnerable to market downturns and bad financial advice.
Antifragility: They’re treating every “YOLO” trade as a learning opportunity after the last two years. Documenting wins and losses, analyzing mistakes, and using that knowledge to develop a more informed investment strategy.
28, Director of Product Marketing at a Series D Startup: Hustling 60+ hours a week, drowning in VC buzzwords, and secretly wondering if “democratizing AI-enabled ERP solutions” is actually making the world a better place. Also, secretly terrified of the Patagonia Vest Recession finally catching up to them.
Financial Priority: Paying down student loans, keeping up with rent in a HCOL area, and pretending they’re not living paycheck to paycheck.
Fragility: Heavily reliant on a single job, no way to get a line of credit based on equity position in the company and very vulnerable to layoffs in a currently volatile industry.
Antifragility: They started a “f#%k you fund” – only promising to do 40 meaningful hours at work and instead will focus on a side hustle or investment account that generates enough income to get the freedom to walk away from a toxic work environment. They’re basically building their own personal parachute.
35, Great Job, Medium/High Cost of Living: Staring blankly at their laptop screen, fantasizing about quitting to backpack through Southeast Asia, learn pottery, or finally write that novel. (But $3,800 in rent is due next week...)
Financial Priority: Saving enough cash to escape the 9-to-5 grind, even if it means sacrificing long-term investments (and ignoring the nagging feeling that you’re falling behind).
Fragility: Dependent on a single source of income and vulnerable to burnout and dissatisfaction.
Antifragility: Instead of quitting cold turkey, a friend of mine has started experimenting with “mini-retirements” – taking a week or two off to pursue your passions and see if they can turn them into a viable income stream.
42, Principal at a Management Consulting Company, Two Kids in Elementary School: Spending weekends reviewing client decks, attending partner meetings (virtually, of course), and secretly wondering if you’re actually making a difference in the world, or just helping corporations become more efficient at extracting value.
Financial Priority: Maximizing firm profits, securing new clients, and ensuring a comfortable retirement.
Fragility: Dependent on the firm’s success, vulnerable to economic downturns, internal politics, and constantly battling burnout from demanding clients and travel schedules.
Antifragility: They’re leveraging their consulting expertise to write a book on a niche topic within their industry and investing in couple of early-stage companies that are specifically disrupting the consulting model. They’re basically creating a “put option” on their career which I thought was really freaking smart.
58, Empty Nester, Mortgage Almost Paid Off: Finally has some breathing room, but now they’re obsessing over optimizing their 401k, terrified of outliving the savings on hand, and wondering when they should finally take those extended vacations with their partner to another country.
Financial Priority: Catching up on retirement savings after years of putting the kids first, and desperately hoping Social Security will still be around when you need it.
Fragility: Overly focused on financial security and potentially missing out on opportunities for joy and fulfillment.
Antifragility: This isn’t happening just yet, but they’re hoping to “un-retire” soon – they’re hoping to find a part-time job or volunteer opportunity that allows them to use their skills and experience to make a difference in the world, but can drop things on a moment’s notice when its financially opportunistic to drop their work and ship off to that country for a couple of months.
So, there you have it. From YOLO trades to exit strategies, everyone’s cooking with different ingredients.
The key? Let’s ditch the tunnel vision. Maybe take a little antifragility from someone else’s phase in life and it might do us all some good.