When you sell a business, the offers start showing up. Within months of the close, your name is on lists you didn’t ask to be on, and suddenly there’s a country club, a city club, a deal-flow social club, a private aviation card, and a family office intro service all pitching you at once. A listener wrote in this week: thirty-seven, just cleared $18 million after tax, and wanted a framework for sorting through it all. Here is the one we use.
The Pitch Will Find You First
Liquidity events are noisy. The legal filings are public, the brokers and bankers talk, and your name moves onto subscriber lists fast. Within six months you’ll get pitched on memberships, services, and “exclusive” opportunities you didn’t know existed. The first thing to internalize is that almost none of these came to you because you specifically need them. You’re a fresh deposit on someone’s prospect list. The burden of proof sits with the salesperson, not with you.
Start With What You Actually Want
The single best filter is your own life. Before evaluating any of these, write down what you actually want the next two to five years to look like. Are you traveling internationally for months at a time? Are you starting another business? Are you spending more time with your kids? Once that picture is real, most of these decisions answer themselves. Spending $85,000 to join a club you’ll never visit because you’re going to be on a beach in Portugal is not a wealth move. It’s a marketing win for whoever sold you on it.
This is also where it helps to have a fiduciary in the room. Feel free to blame us, your advisors, when you say no. We are happy to be the bad guys if it gets you off a sales call.
Country Clubs and City Clubs: A Values Question
Of the items on this list, traditional clubs are the easiest to evaluate honestly. The question is not “do successful people join these,” because the answer to that is yes and no in roughly equal measure. The real question is whether you’ll actually use it and enjoy it. We know plenty of people who joined a golf club because they thought they were supposed to, then wondered for years why they never went up there. If golf is a passion or the city club is a real piece of your social and professional life, the dollars can make sense. If you’re forcing the fit, the right answer is no.
The Social Club With the “Long Wait List”
Be skeptical when a club’s primary pitch is deal flow and access. Start with the underlying question: do you actually need more deal flow right now? If you don’t have a strategic reason to be sourcing private deals, paying to join a club that supplies them is solving a problem you don’t have. And the “long wait list” framing tends to evaporate the moment you express interest, which tells you something. If the wait list is real and there’s no fee to be on it, by all means add your name. Then keep living your life.
Aviation Cards: One Place Where the Math Is Easy
Private aviation is the one item on this list where the analysis is mostly numbers. Map out your realistic travel schedule for the next two years: how many trips, how far, when, and with whom. Then price three options against that schedule: business class on commercial carriers, an aviation card, and short-term charters. Ownership at $18 million of net worth is generally a stretch, because the planes that fit that budget rarely have the range you’ll actually want, and ongoing maintenance is a heavy fixed cost.
In our experience running this math, aviation cards rarely come back as a slam dunk. Business class often wins, and chartering covers the trips where it doesn’t.
Family Office Services at $18 Million
The last one is the easiest. At $18 million of net worth, you do not need a family office. The tax planning is manageable, the estate planning starts with a few well-drafted documents, and the investment work at this level is straightforward, especially when most of the wealth is fresh cash. If you grow into a family office later, that decision can be made then. Today, you’d be paying for the answer to a problem you don’t have.
Saying No Is the Highest-Leverage Skill You Can Learn
A liquidity event is one of the few moments in life when nearly every decision in front of you is reversible except spending. Memberships have buy-ins you don’t get back. Cards have minimums. Services have multi-year retainers. The most valuable skill in the year after a sale is the ability to say “not yet” without guilt. Sit on the cash, get clear on what you actually want, and let the people who need a piece of the $18 million wait. Most won’t still be calling in six months, and that itself is useful information.
This post is adapted from a recent episode of the Scholar Wealth Podcast. For more perspective on evaluating clubs, aviation cards, and family office services after a liquidity event, listen to the full podcast episode here.