“I’ve been a collector forever,” the founder of venture capital firm BoxGroup said from his Meatpacking District office, surrounded by an assortment of whimsical collectibles. The crown jewel of Tisch’s collection, however, isn’t so easily displayed on a shelf: Tisch and BoxGroup were among the very first investors in AI coding startup Cursor, which this month was acquired by Elon Musk’s SpaceX for $60 billion, the largest VC-backed acquisition of all-time.

The returns are staggering: BoxGroup first wrote a $750,000 check to Cursor CEO Michael Truell, plus two follow-on checks, ultimately proffering a return that should shake out to around $1 billion, a source familiar with the matter told Fortune.

It’s the kind of home run most VCs dream about their whole career and, for Tisch, there are all sorts of throughlines. For one, investing is a form of collecting—from portfolio construction to placing your bets—and Tisch, 45, sees a parallel between investing in startups and the sports cards of his childhood. “Especially in early-stage investing, you’re buying something, someone, at the earliest stage, and then you get to see their careers play out.”

For Tisch—warm with a sardonic edge and, yes, a scion of one of business’s most famous families—the Cursor acquisition also affirms the strategy he’s been chasing all along: That the person you’re backing matters most. And Cursor was sourced by then-principal Claire Smilow (now a partner). So, back in 2022, it was a bet by Tisch on both a young investor and a young founder who, at the time, seemed like he was off-point.

“Michael’s original idea was to do AI for CAD [computer-aided design],” Tisch said. “The decision to get excited about investing in Cursor was never about AI for CAD. It was always about the people.”

Over the last 15 years, venture capital’s gotten bigger by the numbers, and louder by pretty much any metric. Firms and their VCs tussle for relevance, ownership, and board seats. Money is everywhere: A billion-dollar fund now is de rigueur. Tisch, meanwhile, has zagged: He doesn’t talk to reporters much, doesn’t have a podcast, backed off tweeting in 2015, doesn’t take board seats, has no interest in raising a multi-billion fund, and is viscerally uncomfortable with any startup narrative where an investor is the protagonist. It’s a contrarian take that, in this environment, is out of vogue, at best. But Cursor’s blockbuster buyout suggests, against the odds, that Tisch’s vision of a restrained, people-first model for venture capital can work in a world dominated by trillion-dollar companies and multi-billion funds. 

“David and BoxGroup are sort of the last stalwarts of highly collaborative investing,” said Jack Altman, Benchmark partner who’s known Tisch since 2020 (and yes, Sam Altman’s brother). “It used to be that VCs could collaborate a lot more easily. Then, over time, as VCs got much bigger, it got more competitive—there are only 100 points on the cap table. But Box has taken the view of ‘we’re going to invest in a ton of companies, we’re going to do it super collaboratively, so we can always come along with other investors. That way, we can share and receive deal flow from everyone.’ All the VCs who scaled up, they sort of gave up on that strategy. And Box is the hold out.”

That restraint, that desire for collaboration, isn’t just philosophy. It’s core to BoxGroup, which arguably has its origins in Tisch’s childhood fascination with the Internet, with early message boards and chasing baseball (and hockey, and basketball) cards online. 

“In the sports card world, if I buy a rookie and the rookie fails, I never met him, I don’t care. I’m sad for me,” said Tisch. “Whereas in startups, you’re investing in a person you build a relationship with, and you might watch them go through a life‑changing success—or a life-changing failure.” 

“I started with dial-up”

Tisch came of age attuned to the dawn of our digital world. And he wants you to know: He was here at the start.

“I started with dial-up Internet, the actual sound,” he emphasizes with comic timing. “There’s kids who started at the end of the dial-up era, and there are kids who started at the beginning. I’m the beginning.”

Tisch is characterized by his disarming, self-deprecating humor, and he makes me think of that Italian word sprezzatura—it describes someone with genuine skill that they’ve learned to make appear deeply casual. The humor and casualness, one has to imagine, are both nature and nurture. As an Internet-loving kid in Scarsdale, he came from an illustrious family—his grandfather, Laurence Tisch, was co-owner of the generational Loews Corp. conglomerate, and the Tisch family (known for its high-profile philanthropic endeavors, and prominence in both business and politics) is said to be worth over $10 billion. The family’s success in business didn’t mean, however, that they “got” Tisch’s love of sports cards or the Internet.

“My grandfather, who was instrumental in my life, thought it was the dumbest thing he’d ever heard of,” said Tisch of Laurence, who with his brother built a 20th century empire that spanned hotels, movie theaters, financial institutions, and the Bulova Watch Company. “He was a businessman and entrepreneur—though I didn’t know that word at the time. He thought cards were dumb, and made that very known. I loved cards, but he was adamantly [against it]. Looking back, he was wrong, and it was bad advice.” 

Back then, there was no eBay, and deals got done with snail mail money orders. AOL and message boards were a funny, fraud-riddled place for a kid (Tisch vividly remembers online-buying a fraudulent rookie card of someday-baseball hall-of-famer Mike Piazza that never showed up). He was always drawn to where the offline and online worlds met—the town of Larchmont once hired a 14-year-old Tisch to help build an online town directory—and he was always tracking real-time technological change.

“I grew up in an analog world, but watched digital happen,” Tisch said. “In college, freshman year, 23 of us were in a fraternity class. Two people, not me, had a cell phone. By junior year, all 23 of us had cell phones. In an 18-month period, cell phones went from random and rare to 100% adoption.”

He may have been paying attention to the internet, but he chose a traditional path to start his career. Tisch went to law school, eventually landing (with some restlessness) in real estate finance at Vornado Realty Trust and then at information services company KGB. Then came the Great Financial Crisis.

“I got fired, I’m sitting in my house, depressed,” said Tisch. “And I became intellectually obsessed with accelerators. We’d spent two years trying to launch something within [KGB], and nobody knew what to do. Then, I’d read about Y Combinator and Techstars, which had started in Boulder, expanded to Boston, and announced Seattle. And I’m like: What about New York? Is this going to happen in New York?”

So, at an event, Tisch chased Techstars founder David Cohen and, in relatively short order, he was managing director and a cofounder of Techstars NYC. It was a wild time—tech in New York was finding its legs, the rollicking IPO of Facebook was near, and Bloomberg even stood up a short-lived reality TV series about Techstars NYC, complete with cameras following Tisch. Around this time, Kareem Amin, now CEO and cofounder of $5 billion company Clay, was working on his first startup and met Tisch through Techstars.

“He’s quite charismatic, was then and is now,” said Amin. “He’s a larger-than-life character. One thing I think he really does is give permission. That’s something you really need in entrepreneurship—and he will just do things and say ‘here’s what I think.’”

Tisch made his first investment before Techstars, writing an angel check with family money into early social media platform Boxee in 2008. 

“I needed an entity to put on the cap table,” said Tisch. “So, I created an LLC called Box for Boxee. I thought it was the single investment I was ever going to make.”

Boxee, of course, was the beginning of BoxGroup. At Techstars, Tisch did his own deals, meeting hundreds of young entrepreneurs and learning to recognize the ones that had potential. 

“At Techstars, you got to see the beginnings of a dream, the beginnings for these raw founders with ambition who wanted to create something from nothing,” said Tisch. “And what we do today is the exact same thing: we’re meeting people at the very beginning of their journey. Sometimes they’ve built something, sometimes they have customers, sometimes they have revenue. But a lot of the time, it’s just the people.”

“Always the beginning”

Tisch spent years figuring out if BoxGroup could work, first taking the leap from Techstars to do deals with family money. He’s very aware that made those early days possible. 

“[Family background] gives you opportunities, and that’s factually going to involve opportunities that other people don’t have,” said Tisch. “To not acknowledge or appreciate that is aloof and bizarre. At the same time, that privilege also doesn’t automatically allow you to do something on your own.”

BoxGroup’s first three family-backed funds kicked back returns and winners, including ID.me, Warby Parker, Plaid, and Zipline. Finally, in 2019, BoxGroup raised its first institutional fund (and its fourth fund overall) of $82.5 million with a follow-on fund of another $82.5 million.

The firm’s strategy cut against the traditional VC approach from the start. “Our early-stage portfolio, for each one of our funds, is 120 to 150 companies,” said Tisch. “The traditional venture fund’s about 30 companies, so we’re taking a different approach to how we build portfolios.”

Now, in the mid-2020s, venture seems to be all about big numbers and board seats, fighting tooth-and-nail to defend ownership in hot startups. But BoxGroup’s skipping all that. 

“Our win motion is making it easier to get to a yes on both sides,” said Greg Rosen, partner at BoxGroup. “We don’t peg to ownership, because all that matters is being in the right company. There have been examples where we’ve written 50k checks.”

Cursor, perhaps, is slam-dunk proof that being first and right is most of the battle. And how the deal happened is telling: Claire Smilow, who had taken a break from BoxGroup to go to Harvard Business School, met then-MIT sophomore Michael Truell in 2019. She’d interviewed him for the student VC firm Dorm Room Fund, and thought he was “insanely special.” When she returned to BoxGroup in 2022, Smilow insisted the firm back Truell before anyone else. Even though Truell was then chasing an esoteric idea around AI for CAD, Tisch and the partners at BoxGroup listened. 

“It takes a really special collaborative culture to be able to say, ‘We trust you, and we’re going to make this decision together,’” said Smilow. “If people had said, ‘I don’t buy that idea, are you sure he’s good enough?’—if I’d had to defend him in a room of really critical senior investors who had all worked there for ten years—it’s possible I could have caved.”

While Cursor’s original parent company Anysphere raised an $8 million seed round in October 2023, BoxGroup made its initial $750,000 investment in Truell in June 2022, in a deal that was among more than 100 investments in BoxGroup’s fifth $127.5 million fund. Though it’s a moving target, pending SpaceX’s performance in the public markets over the next few months, BoxGroup’s return is likely to amount to more than all the LP capital the firm’s ever raised. 

BoxGroup has other winners in the pipeline, like Ramp, Baseten, Plaid, Rogo, Factory, Mach Industries, and Clay. Clay, the AI sales and data startup, is now valued at $5 billion. The company got off to a rocky start, but Tisch’s bet was on Kareem Amin, who he’d known from their days at Techstars. As Amin tells it now, Tisch was among the first to see Clay hit its hockey-stick-moment, and sign on for the ride. 

“What David did better than everybody else: when you’re in a hot company and something’s happening, the biggest fights are usually about pro rata,” said Amin, referencing an investors’ right to invest more money to retain their ownership. “David was like, ‘Hey, I want to make it as easy as possible for you, go get that great lead and you tell us what our pro rata is.’” 

How someone invests says something about who they are. So, this investing approach is BoxGroup, but it’s also Tisch, said Mindy Isenstein, an a16z Perennial partner who’s known Tisch since they were teenagers: “David’s acutely aware of who he is and where he fits.” 

Indeed, in Tisch’s own words, his purpose is clear. 

“My job today is to take money from investors and give them back a lot of money,” Tisch said. “There’s that purely capitalistic expectation of what you sign up for as an investor. So, when you ask me about how venture’s changed, I don’t think about that. I think about finding the next person that hasn’t started a company yet, who will create something that matters.”

It’s appropriate, perhaps, that Tisch and I had this conversation in his office surrounded by his collections, from colorful Grateful Dead memorabilia to a wall of bears. (Bearbricks, to be specific—a fanciful, bear-like Japanese collectible that’s vinyl and comes in infinite colorways, from camo to watermelon. Tisch estimates he has about 600.) Tisch, like all of us, is in many ways the person he always was.

“I still think I’m an internet investor,” Tisch said. “I like that word better than VC.”

He, in fact, doesn’t like the term VC at all. It has connotations of self-importance, he said, and he bristles at the label. Investing, for Tisch, is especially an exercise in timing. The beginning, after all, is why we start.

“I’ve always loved the beginning and only the beginning,” Tisch smiles. “The middle and the end are someone else’s problem.”