The 30th anniversary of Tommy Boy was recently commemorated in Sandusky, Ohio, with the first Tommy Boy Fest. I was sorry to have missed this event since the schedule looked like a blast, complete with Q&A with Director Peter Segal and Julie Warner (“prettiest gal in Sandusky”), a comedy show with Kevin Farley, and a Tommy Want Wingy throwdown. Although Tommy Boy was filmed in Canada, the movie was based in the city of Sandusky and if this festival becomes an annual event, my family will definitely be traveling there next year.

My kids love Tommy Boy (and Chris Farley) as much as I do and after a recent re-watch of the 1995 flick, I kept thinking about some of the smaller scenes with big undertones, particularly regarding the management of Callahan Auto Parts and the emphasis on it being family-owned.

Early in the movie, there is a scene with Tommy’s father, an auto parts tycoon known as Big Tom (played by Brian Dennehy), and he is sharing his plans for a new brake pad division while walking down a hallway with a few businessmen. Ron Gilmore, the town banker (played by James Blendick), is walking alongside him and seems concerned about the sizable bank loan that will be needed for this new endeavor. Big Tom, in pitching his idea, declares “Don’t tell me the bank thinks we need to wait it out. Any business that tries to wait it out will be just that: out. In auto parts, you’re either growing or you’re dying. There ain’t no third direction.” And Big Tom is right. Complacency and competitive inertia are the surest ways to lose any battle over market share in the business realm. 

Big Tom’s statements are confident and convincing, but Gilmore is still concerned. “Tom, you’re talking about a huge loan. Maybe instead of borrowing, you should take on a partner.” An idea Big Tom quickly shoots down. “No, this always has been, always will be a family firm. My grandfather founded it in ’21. My father kept it running during the Depression. My Aunt Eileen ran it when he went away to war, and someday, my son will run it.”

In this short scene, several factors are at play, but for the sake of this article’s length, let’s just focus on the family business element. And to do so, some context is needed.

The Premise

Big Tom believed in the Callahan brand, and he lived well because of the success he achieved. Big Tom’s residence is one to behold: a huge mansion, gorgeous grounds, and a massive inground swimming pool (good enough for Bo Derek). And thanks to his wealth, Big Tom was able to support Tommy Boy’s elongated college education as well as guarantee him a job post-graduation. One of my favorite scenes in the movie is when Tommy receives his private office at his father’s firm, and Richard Hayden, an executive assistant (played by David Spade) alludes to the nepotism by sarcastically stating “You have a window! And why shouldn’t you? You’ve been here ten minutes.”

Other than a few quips from Richard throughout the film, employees at Callahan Auto Parts are featured as being unbothered by the family favoritism and don’t begrudge their employer’s lavish lifestyle. Actually, it is hard not to like the Callahan family. Big Tom is charismatic and appears to treat employees well, while Tommy is caring and kind, making it easy to disregard his mishaps and shenanigans. When touring the factory after returning home from college, Tommy greets all the workers by name and shows a genuine interest in the work they are doing. 

Overall, Tommy’s strength (we won’t go into his rather obvious faults) lies in generating interpersonal connections, and when he needs to take charge after the sudden passing of his father, Tommy is well-received by most of the employees despite the lack of competency he has for his new role.

The Perception

What is truly interesting about Callahan Auto Parts is how the business is presented and perceived. Big Tom ran a big business, and it being family-owned was a big deal. While I can understand a father wanting to see his legacy live on through his son, I am always a bit perplexed why consumers should care whether a firm is family-owned. Yet, for some reason, in American culture, family businesses have positive appeal, and businesses heavily promote familial ties. 

If you start paying attention to taglines, you’ll find that all types of firms market themselves as family-owned. One of my favorite examples is Sierra Nevada Brewing Co., which features at the top of its cans “Family Owned, Operated & Argued Over.”

When a successful business can be passed on to future generations, this is generally viewed as a good thing and something to be proud of. Some of America’s oldest and largest firms are family-owned: The Ford Motor Co., Koch Industries, Inc., The Kohler Co., S.C. Johnson, and Wegmans Food Markets to name a few. However, when a firm is perceived as being too big and too successful, those good vibes tend to fade away. Think the Waltons of Walmart or the Hiltons of, well, Hilton. 

When we perceive a company as being too powerful or a family as being too high status, we are less enthused about the family aspect. But we must remember that business owners generate their wealth by means of the success of their business. And the success of a business depends on its efficacy in serving the market and its ability to cater to consumer interests. Walmart didn’t get big overnight, and consumers weren’t forced to shop at Walmart stores. 

Moreover, some of the heirs of big businesses do great things with the wealth they have attained. Most notably and most recently, the Alice L. Walton School of Medicine inducted its first medical school class. Not only did the Walmart heiress, Alice Walton, fund the creation of a top-tier medical school, but, as featured in Time Magazine, she is also “covering tuition for the first five graduating classes.” 

The Point

The next time you purchase a product or put your trust in a brand, try to assess all the signals being sent your way. Does it matter to you if the business is family-owned? Does it matter to you if the business is big or small? And if any of these factors do matter, ask yourself why. Also, ask if you might feel differently if you were the business owner.

The ‘shop small’ and ‘shop local’ mantras sound great, but we should remember that a lot of value is derived from big businesses that were once small. And while supporting family businesses certainly sounds nice, in reality, there is no way to know what goes on behind closed doors. The family that owns a business could be made up of horrible people. Or the founders could be coercing future generations to forgo their individual dreams to sustain the family’s brand name. 

Just because a business is family-owned doesn’t automatically make it good, just as a business that is not family-owned isn’t inherently bad.

Fortunately for Tommy Boy, he came from a loving family, and he’s lucky that his father took great pride in the business being family-owned (since it’s unlikely Tommy could get a job anywhere else). And it’s a good thing for Tommy that his father’s company wasn’t the only big business competing in the auto parts realm. At the end of the movie (spoiler alert) Tommy is able to trick the owner of Zalinsky Auto Parts (played by Dan Aykroyd) into purchasing 500,000 brake pads. The big sale saves the company, and Tommy is able to return to Sandusky a hero. And, as stated at the start of this article, I look forward to visiting the real city of Sandusky someday since I know my kids would get a kick out of it. 

The experiences I take part in and the investments I make are based on my preferences, my aspirations, and the future well-being of my family. Although I may not be able to set my kids up with an inheritance comparable to the fictitious Callahans or the real-life Waltons, I am doing my best to ensure they can be proud of the wealth we have attained. 

I am also teaching my children that what constitutes wealth can come in a variety of forms, and it is up to them to determine what it is they truly value. And I’ll be reminding them that no matter their age, I will always be happy to re-watch Tommy Boy with them since there is always something to be learned from the energetic and entrepreneurial spirit present in this 1990s classic.

In 1956, a trucking entrepreneur named Malcolm McLean did something quietly radical: he placed 58 identical steel boxes onto a cargo ship in Newark and sent them to Houston. Those boxes, the first standardized shipping containers, didn’t look like a revolution. But they soon rewrote the logic of global commerce.

As economist Marc Levinson chronicled in The Box, this wasn’t just about saving space or time. The genius of the container was its standardization. No matter the cargo, no matter the destination, one set of protocols including fixed dimensions, stackability, and compatibility with cranes, trucks, and ports suddenly governed a previously fragmented industry. Costs fell. Transit times collapsed. Theft and spoilage plummeted. Global trade surged from $100 billion in 1960 to over $25 trillion today, largely because containers allowed goods to move frictionlessly through a universal system.

What the shipping container did for physical goods, stablecoins now promise to do for money.

The recent bipartisan passage of the GENIUS Act and the expected passage of the CLARITY Act in the next few weeks, is the policy equivalent of agreeing on the international container standard. It establishes a framework for dollar-backed stablecoins, digital tokens whose value is pegged 1:1 to U.S. dollars and backed by reserves held in cash or short-term Treasuries. Issuers must meet rigorous disclosure, audit, and consumer-protection requirements. In short, the Act sets the rules to make stablecoins not just safe, but also scalable and interoperable by defining basic regulatory guidelines.

That distinction matters. Because like early maritime trade before containerization, today’s financial system remains fragmented, expensive, and slow. Sending money internationally often takes days, involves multiple intermediaries, and racks up fees, especially for consumers and small businesses. Different ledgers, jurisdictions, and systems don’t talk to each other.

Stablecoins change that. They are programmable, 24/7, borderless instruments that allow dollars to move instantly across platforms, contracts, and geographies. They’re not trying to replace the dollar; they’re trying to standardize its transport, just as containers didn’t replace ships, they made ships dramatically more efficient.

Even before the GENIUS Act, the market for stablecoins was exploding. In 2024, stablecoins processed over $27 trillion in transactions, more than Visa and Mastercard combined. Over 90% of that volume was denominated in U.S. dollars. And, unlike cryptocurrencies like Bitcoin, these aren’t speculative assets. They are increasingly the infrastructure of modern financial exchange.

But just like container adoption required more than a clever box, it required regulatory alignment, international buy-in, and standardized protocols, stablecoins need legislative scaffolding to scale securely. The GENIUS and CLARITY Acts provide that scaffolding. This legislation sets a bar that serious, well-capitalized issuers can meet and ensures dollar-backed tokens are trusted, transparent, and functional at scale.

The benefits are profound. For consumers, it means faster and cheaper transactions. For entrepreneurs, it unlocks programmable financial applications. But for the United States, the biggest benefit is macroeconomic and geopolitical: the GENIUS and CLARITY Acts will increase global demand for U.S. dollars.

Every compliant stablecoin must be backed by reserves held in dollars or short-term Treasuries. As stablecoins are adopted globally, for remittances, trade settlement, and digital contracts, they become a continuous engine of demand for dollar-based assets. Morgan Stanley estimates this could generate trillions of dollars in new demand for U.S. government debt, strengthening Treasury markets and lowering borrowing costs.

It also fortifies dollar primacy. In a world where China is pushing a digital yuan and the EU is experimenting with a digital euro, the U.S. must export not just currency, but currency infrastructure. Stablecoins are the shipping containers of monetary influence. If we define the standard, the world will adopt it. If we hesitate, others will fill the vacuum.

To be clear, stablecoins aren’t risk-free. But their risks, such as liquidity mismatches, fraud, systemic exposure, are precisely the kinds of challenges that regulation is designed to manage. The current crypto legislation addresses them with measured oversight. It is neither overbearing nor permissive, it is infrastructural.

The true lesson of the container revolution is this: infrastructure wins not by invention, but by consensus. Once enough actors agreed on the rules, global trade scaled almost automatically. Stablecoins offer the same promise for digital commerce if we codify their standard.

Both the GENIUS and CLARITY Acts are not just about enabling crypto. They are about ensuring the U.S. dollar remains the base layer of global finance in a world that is moving, inevitably, toward digital rails.

The future of money needs a container. We have it. Now we need to standardize it and lead.

For decades, New York City prided itself on being the financial capital of the world. It’s a place where money, culture, and power converge. And yet, as has been seen in San Francisco, Chicago, and other locations around the US, New York is experiencing a steady exodus of millionaires and ultra-high-net-worth individuals. While some observers dismiss this as anecdotal or exaggerated, the facts paint a different picture: one with serious implications for the city’s fiscal health, social fabric, and attractiveness.

It is easy to forget that New York’s gleaming infrastructure, vast public services, and social programs are underwritten disproportionately by a tiny number of residents. Fewer than one percent of taxpayers account for more than 40 percent of all income tax revenue collected in the state, and a similar share in the city. Without those individuals, the ability of millions of ordinary New Yorkers to enjoy subsidized transit, robust public safety services, and cultural investments would collapse. In other words, and despite endless egalitarian rhetoric, the lifestyle of the masses is silently carried on the shoulders of the few.

The scale of the loss is becoming visible. Between 2019 and 2020, the number of New Yorkers earning between $150,000 and $750,000 fell by nearly six percent, while the number of true high earners — those making over $750,000 — dropped by nearly 10 percent, according to the city’s Independent Budget Office. This erosion matters because the city’s top one percent — about 41,000 filers — pay more than 40 percent of all income taxes. The top 10 percent pay about two-thirds. Which means the remaining 90 percent of taxpayers contribute only about one-third of the city’s income tax revenue. When even a small share of these high earners disappears, the impact is seismic.

Recent migration trends confirm the damage. More than 125,000 New Yorkers have fled to Florida in just the past few years, carrying nearly $14 billion worth of income with them, according to the Citizens Budget Commission. About a third of those movers — more than 41,000 people — went to Miami-Dade, Palm Beach, and Broward Counties between 2018 and 2022. Those escapes alone stripped New York City of an estimated $10 billion in adjusted gross income. When money and mobility align, no amount of political rhetoric can stop people from voting with their feet.

Into this fragile situation steps Zohran Mamdani, whose mayoral primary victory has been accompanied by a platform that includes a new “millionaire’s tax.” His proposal would tack on an additional two-percent levy for New Yorkers earning more than $1 million a year, raising the combined city and state top rate to 16.776 percent — by far the highest in the nation. Add federal obligations, and the total burden would rise to nearly 54 percent. That is not just taxation; it is confiscation. 

Wealthy New Yorkers wouldn’t even need to flee to Florida to avoid it. A short move to Westchester, Long Island, or across the Hudson to New Jersey would suffice. As the Tax Foundation has noted, “a high earner doesn’t need to give up the convenience of the city, they just need to move outside the five boroughs.” Developers are already banding together to oppose Mamdani’s rent-control platform, while Florida realtors report a surge in inquiries from wealthy New Yorkers looking to relocate.

Rather than acknowledge this delicate balance, policymakers in Albany and City Hall continue to treat the wealthy as inexhaustible resources. Each subsequent budget cycle seems to bring fresh proposals for higher levies, justified by a reflexive invocation of “fair share.” For the city’s most mobile taxpayers, however, there is a limit. They are increasingly concluding that enough is enough.

Not to worry, though. Other US states and cities are only too happy to receive them. 

Florida has no state income tax and a climate that, quite literally, feels like a bonus. Texas markets itself as a business-friendly, family-friendly destination where capital is welcomed rather than penalized. The Lone Star State is even planning its own stock exchange to fight against corporate ESG/DEI mandates, among others. Even Connecticut, once derided as a commuter’s backwater, now makes a pitch as a calmer, lower-tax alternative just a train ride away.

It’s not just states. Municipalities from Miami to Austin to Nashville are creating entire ecosystems — schools, cultural centers, financial services clusters — designed to attract, satisfy, and retain disaffected New Yorkers. And the migration data show that these efforts are paying off.

The most striking irony of this government-greed-driven exodus is that the very policies promoted as remedies for inequality are accelerating a new divide. On one side are jurisdictions with extractive tax regimes like New York, which are increasingly reliant on a shrinking base of wealthy residents. On the other side are “merely high-tax” or moderate-tax states that calibrate their revenue needs without driving out their most productive citizens. In attempting to punish the “haves” in the name of the “have-nots,” New York is in the process of creating an even sharper divide between places where the wealthy live and places they have left behind. The intended redistribution becomes a geographic one, with capital, philanthropy, and jobs following the departing millionaires.

Beyond dollars and cents, there is also a cultural cost. Wealthy New Yorkers are not just taxpayers; they are patrons of the arts, benefactors of hospitals, and funders of civic institutions. When they decamp to Florida, Texas, Tennessee, Wyoming, or elsewhere, they don’t merely take their checkbooks; they take their boards, galas, and fundraising networks. The very character of New York as a city of ambition progressively dims. A city that once attracted the world’s best and brightest risks becoming a place they leave once they have achieved the successes they sought.

The migration of millionaires is not an abstract threat. It is an early warning sign of the consequences of fiscal imbalance and political avarice. New York can continue to chase headlines with promises of soaking the rich, or it can recognize that prosperity depends on partnership, not punishment. If it chooses the former, the flight will only accelerate, and the city may wake up one day to find that its most valuable export is no longer finance or culture, but people. Wealth, like love, does not stay long where it goes unappreciated.