But it’s that competitive landscape that has the ultrarich looking to go direct, said Arthur Bavelas, who organizes lunches in New York to facilitate direct investing. Companies looking for money pay him a fee to present opportunities, and he promotes the event to his list of 800 wealthy families, who attend for free.

“They want deal flow that’s ripe with opportunity and hasn’t been picked over by others," said Bavelas, who has held about four dozen such gatherings this year. While he doesn’t offer an opinion on investments, he has put his own cash into a handful of presenting companies, including one last year for Finix Solutions, a wealth-administration platform for alternative assets.

Other investors find deals through the more traditional route: wealth advisers and banks, who are adding direct investing to their white-glove services for the rich -- and getting lucrative fees. For a family with $100 million to invest, upper-end advisers charge about 40 to 50 basis points -- $400,000 to $500,000 -- annually.

Through a program called Morgan Private Ventures, JPMorgan Chase & Co. offers some clients -- typically those with more than $200 million to deploy -- a chance to invest in companies that are raising funding rounds, or with private equity and venture firms seeking to fill excess capacity in pools that invest alongside their funds. That’s led to client investments in South Korean e-commerce giant Coupang, restaurant delivery service Deliveroo and electric-bus maker Proterra Inc.

An investment into a young entity gives a family “a front-row seat on how that company is performing, the edge that that company’s technology or business model or product brings to the market,” said John Duffy, global head of institutional wealth management for JPMorgan’s private bank.

At Goldman Sachs Group Inc., private wealth clients with as little as $10 million got the opportunity to put money into Cadre, a real estate tech startup partly owned by Jared Kushner. The bank’s investors committed $250 million to buying properties on the platform, getting a small equity stake on top of that.

Conflicting Interests
Multifamily offices can bring their client base together for deals. Wesley and Paul Karger at Boston-based Twin Focus Capital Partners, which has more than $4.5 billion under advisement, encourage their 30 families to get to know one another. When one client asked if the company would want to pitch in on buying a $10 million office building in Massachusetts, Twin Focus helped them model the risks, get financing and close the deal. It also brought along two other families to help fund it, said Paul Karger, who leads the firm’s direct-investing efforts.

None of these arrangements is without conflicts. Banks, paid to raise money by a startup or seeking to curry favor with a private equity fund, have an incentive to fill the fundraising rounds they bring to market. Advisers who source deals from one client to offer to other families it works with have a vested interest in keeping the original party happy, said Lawrence Calcano, CEO of alternative-investment network iCapital.

“The bar is high for any adviser showing direct investments to their clients, and the bar might be even higher still if the source of that investment is another client,” he said.

And while direct investing may be all the talk at soirees like Tiger 21’s gathering in the Hamptons, Cascadia’s Herlihy offers a word of advice: “Most of what we do I don’t think people brag about at cocktail parties. There is a saying about good investments: ‘The more boring the better.’"