The Whiskey Test and Nine Other Things I Learned from a Guy Who Manages Centimillionaires' Money

Why the Smartest Families in America Have Trusted One Man with Their Money for Over Two Decades

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I’ve done something your financial advisor won’t: I’ve distilled 22 years of managing billionaires’ money into a single image you can actually understand.

Below is Will Finnerty’s entire framework in one picture. Study it. Screenshot it. Tape it to your bathroom mirror where your advisor’s glossy brochure used to be.

Here’s the thing: this infographic took me longer to make than it takes most advisors to explain why they underperformed the S&P. So before you scroll past and go back to pretending your wealth strategy is fine, subscribe if you haven’t. Share if you have. Consider it the cover charge for wisdom that usually costs 1.5% of assets under management.

Now for the full conversation. Pour yourself something aged.

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Will has three boys named after whiskey. Jack, Jameson, and Macallan.

I have four kids and named my only son Sterling. Not whiskey, but a metal I happen to love. Old Pappy 23 was just too many syllables for a first name.

Will Finnerty is the managing director and private wealth adviser at UBS, the Swiss bank that manages over $6 trillion and counts three out of four European billionaires as clients. Most of his families have nine-figure liquidity events.

He was the top finance graduate at Georgetown’s McDonough School of Business. His grandfather worked at Dean Witter for 67 years, which I believe is longer than some civilizations lasted.

I sat down with Will for my Fortunate Fishes podcast and came away with ten lessons that most financial advisors either don’t know or won’t tell you. Probably because they’re too busy being charming at cocktail parties.

1. Wealth Management Has Evolved to Life Management

Here’s the dirty secret of the wealth management industry: portfolio construction is now table stakes. You can buy an index fund at Vanguard and stick it in a drawer. You don’t need to pay someone for that.

“If all you’re doing is managing somebody’s money, if that’s what your adviser is doing, you need to find a new adviser,” Will told me. “That’s like warm food. You can get an ETF for that.”

The industry has shifted from stock picking to something far more complex: life management. Will’s team sits at the intersection of four disciplines. Sophisticated portfolio construction with an eye on risk management. Tax planning and structural alpha. White-glove service that’s become baseline. And the newest piece: family office support, which includes governance, shared values, and facilitated family meetings.

The advisors who only talk about returns are like restaurants that brag about having hot food. Congratulations. You’ve met the minimum requirement for existing.

2. What Wealthy People Actually Buy: Peace of Mind

I asked Will what his best clients think they’re actually buying from him.

“Peace of mind,” he said without hesitation.

His wife once told a group of girlfriends that if she had to put something on Will’s tombstone, it would be: “I’ll take care of it.” Because that’s what he says. Constantly. To everyone.

People buy on emotion and back it up with logic. They buy outcomes, not products. The families Will serves don’t want to lose what they’ve built. They want to grow it responsibly. They want to pass it on. And they want to have those difficult conversations with their children and spouses without screwing everything up.

If you’re paying someone to manage your wealth and you’re still lying awake at night worrying about it, you’ve hired the wrong person.

3. Time is “Temporal Capital” (The Only Asset You Can’t Create More Of)

This concept has been rattling around in Will’s head lately, and it should rattle around in yours too.

You can make more money. You can learn more things. You can get more experience. You can belong to bigger communities. You cannot get more time.

One of our R360 members calls it “non-refundable minutes.” You have the time that you have. That’s it.

Will made a game-changing decision recently: he hired a personal assistant for his home and family. Not for his office. For his life.

“She puts toothpaste on my toothbrush and sets it next to the sink,” he told me. “She takes the plastic off the dry cleaning. She prints my morning documents. She packs and unpacks my luggage.”

This sounds extravagant until you do the math. Every hour you spend on logistics is an hour you’re not spending on your family, your health, or the things that actually matter. If you have the means to delegate, delegate. You’re not just buying convenience. You’re buying time, which is the one thing money supposedly can’t buy.

Turns out it can. You just have to be willing to spend it that way.

4. The Only Free Lunch in Finance: Diversification

Economists love to say there’s no free lunch. They’re wrong about this one thing.

“The only free lunch in wealth management is diversification,” Will said. “It’s the only thing that’s going to lock in the idea that you’re not going to lose wealth.”

The problem is that nobody wants to order it. We’re all biased toward what we know. If you grew up in real estate, your portfolio looks like a strip mall. If you’re Finnish, you’re overweight Finnish stocks. If you built a tech company, you’re still clutching tech shares like a security blanket.

How do most clients lose their wealth? They don’t structure things properly. Divorce. Not necessarily their own, but their children’s. Concentration in a single asset class. The same bias that made them successful becomes the thing that undoes them.

5. Three Buckets: Liquidity, Longevity, Legacy

Will’s team organizes capital into three buckets. It’s simple enough that I understood it on the first pass, which is saying something.

Bucket One: Liquidity. Three to five years of living expenses in boring, safe stuff. Munis. Corporates. Nothing exciting. This exists because really nasty markets take about that long to recover. If the world falls apart, you don’t have to sell stocks at the bottom or cancel your vacation.

Bucket Two: Longevity. This is managed like a pension fund. What’s it going to take for you and your spouse to spend what you spend for the rest of your foreseeable lives? That money gets managed conservatively and cascades into Bucket One every year.

Bucket Three: Legacy. Everything else. This is money you don’t need. It gets managed like an endowment. More private markets. Longer time horizons. This is where the art collection goes, the third home, the watches. And this is the bucket that lets you actually plan your estate, give money away while you’re alive, and have a bigger impact on causes that matter to you.

The beauty of this system is clarity. You know what you need. You know what you’ll need. And you know what’s left over for the people and causes you care about.

6. How to Choose an Advisor (The Questions Nobody Asks)

If you’re interviewing financial advisors, here’s what Will says most people forget to ask:

First, are they a fiduciary? There are two ways to serve clients: as a broker-dealer or as a fiduciary. One is regulated by FINRA, which is basically self-monitoring. One is regulated by the SEC, and if you screw that up, you break the law. Wealthier families like the idea that their advisor is legally obligated to be on the same side of the table.

Second, check their U-4. This is their report card. It’s free. Go to BrokerCheck on FINRA’s website and look them up. If there’s a ding, it doesn’t mean they did something wrong, but you should ask about it.

Third, ask how many clients they have. More than 60 relationships for a relationship manager is a problem. You want to make sure people get back to you. Will’s team has a 24-hour rule. No exceptions.

Fourth, ask to meet their spouse. Go to dinner together. Can you learn something about somebody by breaking bread with their family? Absolutely.

Fifth, ask to see their portfolio. Not the numbers necessarily, but the allocation. Does it look like what they’re recommending to you? “There are lots of advisors that have virtually no liquidity in their portfolios because they’re not walking the talk,” Will said. If your advisor is recommending something he won’t buy himself, you have a problem.

7. The Post-Sale Identity Crisis Nobody Warns You About

I asked Will what entrepreneurs underestimate before they sell their company.

“The danger in not coming up with a detailed plan of what they’re going to do after they sell.”

When you spend your life building a business, you can pick up the phone and 5,000 people are anxious to jump at whatever request you have. Once you’re out and the new owner takes over, that goes away. For many people, this is a very difficult pill to swallow.

It’s a huge shift in identity. And if you don’t have a plan, the money finds its way into stupid places. Your buddy’s restaurant. Another friend’s deal. This happens constantly with celebrities and athletes. They don’t have a place to engage, so the capital drifts toward whatever’s in front of them.

Here’s the other thing nobody tells you: stuff gets boring in about 90 days. The new house. The new car. The new watch. You enjoy the anticipation. You enjoy the acquisition. And then somewhere around day 91, it’s just a thing.

But experiences? You enjoy them on the way up. You enjoy them while you’re having them. And you enjoy them when you reflect backwards. Prioritize experiences over things. The research backs this up, and so does common sense.

8. The House of Equilibrium

Will created a framework for his life after a disastrous early marriage that lasted about six months. He was young, didn’t have experience, got swept up in something, and paid the price. When he finally extracted himself, he sat back and thought: how did that happen? I’m a good guy. I do the right thing.

He realized he needed to organize his life to ensure it never happened again. So he built what he calls the House of Equilibrium.

The foundation is relationships. Family, friends, and faith.

The walls are health and personal development. Health is exercise, nutrition, and rest. Personal development is learning, documenting, and exploring.

The roof is your career. Love what you do, grow while you’re doing it, and get paid well for the value you bring.

The chimney is finances. What you make, what you save, and what you give away.

Will taught this framework at Georgetown for 16 years. He still uses it when he journals every morning. And here’s the kicker: when his former students reach out years later, this is what they want to talk about. Not stock tips. The house.

9. What Keeps Families Together: Shared Values, Not Money

There’s a hundred-year study on what makes families flourish across generations. Will referenced it, and I looked it up. Here’s what keeps wealthy families together over time:

A shared set of values. A family purpose beyond money. Honest communication. Shared history. A focus on philanthropy. Respect for individuals regardless of their financial contribution. Regular family meetings. Treating fairness as different from equality.

Notice what’s not on the list? Portfolio returns. Tax optimization. Asset allocation.

“If you haven’t done the work with your children, you’re burdening them with excessive wealth,” Will said. “You’re putting them at a disadvantage.”

Warren Buffett said it best: “I want to leave enough money to my children where they can do anything, but not so much that they can do nothing.”

Will’s family has posted values throughout the house. Triple GIC: Growth mindset, Gratitude, and Grit. Integrity, Curiosity, and Extreme Ownership. Whether his boys like it or not, they’re having these conversations.

10. Create Traditions, Don’t Wait for Them

When Will’s brother Michael was deploying with special forces, Will wanted to give him something. So he got him a gold coin. His thinking: no matter where you are on the planet, whether you need a cab or a place to stay, that’s going to work.

Michael carried that coin on all of his deployments. He’s now going to give it to his daughter. She’ll pass it to her son or daughter.

Will got one for each of his boys. They’ll receive them when they turn 18. When his sons turn 14, he takes them anywhere in the world they want to go, as long as they get good grades and are polite to adults. He found a 400-year-old samurai sword with one son in Japan. They spent two weeks together. When Will is gone, that sword will be his son’s, and then his son’s children.

“The thing about traditions is they have to begin somewhere,” Will said. “Create traditions. Don’t wait for traditions. Be the first.”

These gestures matter. They play into the story of a family and what it means to be part of one. With technology, you can speak into a camera. It doesn’t have to be some boring legal document. The two times people die: when you actually die, and when the last person mentions your name.

What’s far more important than the money is how it was built and the values of the family. Pass those along, and the money has a fighting chance of lasting.

The Unsexy Truth About People Who Have Their Shit Together

Will goes to bed at 8:30 and wakes up at 3:30. He has a 17-step morning routine. He takes a mini-sabbatical every quarter, three days alone somewhere he’s never been, to reflect on the previous 90 days and plan the next 90. His family’s theme for this year: Make it a masterpiece.

That’s the whiskey test, I think. Not whether you name your kids after scotch. But whether you’ve thought deeply enough about your life to know what actually matters.

Will has. And if you’re lucky enough to find someone like him to manage your family’s wealth, you’re not paying for municipal bonds.

You’re paying for someone who’ll take care of it.

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The Fortunate Fishes Interview Series

Friday I talk to rich people. Not fake rich. Not Instagram rich. Not “my daddy bought me a dealership” rich. Actually rich. The kind of rich where you need a guy. A money guy. A guy with a guy.

Will Finnerty is that guy. Twenty-two years at UBS.

You know what UBS stands for? Used to Be Switzerland.

Now it’s “U Better Subscribe.”

Will charges by the million. I charge less than a dollar a day. One of us went to business school. The other one went to war.

For less than a dollar a day, five days a week, this is what you get.

Monday, financial global markets. The analysis your financial advisor isn’t providing because he doesn’t know it.

Wednesday, politics. What the hell is Trump doing and what it means for your money.

Friday, people who figured out the game. Centimillionaires. How they actually think and allocate.

Saturday, the Mischief Library. Fifty books a year so you don’t have to.

Sunday, Dear Charlie. Reader mail. Everybody’s got an opinion. Most of them are wrong. The good ones make me think. The bad ones make me drink.

You know who else works five days? Nobody.

Everybody’s got a side hustle and a podcast about their side hustle and a newsletter about their podcast about their side hustle.

Here’s the dirty little secret. Ten percent of you pay. Ninety percent don’t.

You know what that’s called? It’s called church. Except I’m not promising you heaven. I’m promising you I’ll keep writing.

And bourbon if you’re in Daytona.

Join the Mischief Makers

May the mischief be with you.

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