About a decade ago, Tom Colicchio started writing checks. Not large ones at first, and not on his own thesis—he is the first to say he doesn’t have the wherewithal to evaluate a company. His method was to find people who did, watch what they were putting in, and ride alongside if the conviction looked real.

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That is how a friend told him about Bending Spoons.

The Milan-based technology conglomerate closed a $710 million equity round in October 2025 at an $11 billion pre-money valuation, making it one of a handful of European tech decacorns. Colicchio got in early, exited around that round, and walked away with what he says was roughly a 15x return.

“Essentially, Bending Spoons covered everything else that I’ve done, and then some,” he told me, sitting in his office above his flagship restaurant in Manhattan’s Gramercy neighborhood. The company is now reportedly preparing a U.S. listing that could value it at nearly $20 billion.

Bending Spoons is best understood as a software rollup: it acquires underperforming consumer apps—Evernote, WeTransfer, Vimeo, Meetup, Eventbrite, AOL—and aggressively re-monetizes them, typically with deep staff cuts and price increases. It is exactly the kind of efficiency-first operator that, in another setting, Colicchio will tell you has helped hollow out creative industries. He does not pretend the tension isn’t there. He just took the trade.

It is the kind of return that, in a normal year for American fine dining, would be a fun footnote in a chef’s biography. In 2026, for Colicchio, it is the part of the portfolio that is working.

“It used to always be fun. It’s not really fun these days”

Colicchio is direct about the state of his own industry in a way most operators aren’t. “Craft’s been open for 25 years, and last year was probably our worst year ever,” he said of his Flatiron flagship. “It is what it is. The restaurant business has never been easy, but it used to always be fun. It’s not really fun these days.”

The math, as he described it, is unforgiving. Food costs that ran comfortably at 34% of revenue when he started out now have to be held at 26%. “The only place to get that is to lower your food cost,” he said. “That’s one variable cost you can lower.” Fixed costs, he explained, you really can’t. Beef is up roughly 30% over the past 18 months. Olive oil from Italy has repriced sharply. Spirits and wine have been disrupted by tariff retaliation. “A lot of liquor went up because of tariffs,” he said. “Wine prices have gone up. Certain American liquors are not affected by tariffs. But they’re all affected because a lot of other countries pulled stuff off shelves.”

Bryan Hunt, Craft’s director of culinary operations, said the cost of some luxury ingredients “has just gotten so exorbitant” that the restaurant uses them only for special-occasion menus. “We might have one or two dishes that feature some of those things,” he said. “The stations have gotten a little smaller. I would say some of the dishes are not quite as involved, and there’s not as many touches on the dishes.”

Lunch near the 19th Street flagship has become nearly impossible to fill—a permanent consequence of hybrid work schedules that have thinned Manhattan’s midday office population to a fraction of what it was. Tuesdays are now the best night of the week, Hunt said, because that is when employees are back in the office. Thursday and Friday nights, once reliable, have softened.

The formula has narrowed in ways that go beyond the numbers. “So many restaurants are doing — it’s like the formula,” Colicchio said. “A cup of pasta, a pizza, some salads, and that’s it. Because no one wants to take risks. Taking a risk is expensive.” Diners, he argued, have become as risk-averse as operators. Back in the day, he claimed, he could put anything on the menu, and it would sell: squab, offal, whatever. “I put squab on the menu now, I can’t sell it.” He described a vicious cycle where diners and restaurants alike are less adventurous, and chefs follow suit. “You try to please everyone, and you end up being like the Gap.”

He connected this to a broader cultural compression he sees happening across every creative field at once, against an economy reshaped by AI anxiety and tariff disruption. “What’s interesting to me is that there’s more money sloshing around than ever before,” he said, “and usually you had people who were really wealthy who were the ones financing independent films and financing restaurants. And I just don’t know if that’s still happening.”

Which is, in a roundabout way, how Colicchio ended up an investor in 30 companies. He is too disciplined to call it a hedge against his own industry. But he is also a man who, at every fork in his life, has refused to bet on a single track.

The portfolio, built over roughly the past five to seven years, runs to about 30 companies: a Brown University–affiliated angel group focused largely on medical technology; a corporate food services p