Every three weeks on a Monday morning, Nat Turner flies from New York to Orange County, California to start a work “sprint.” He’s up at 4:30 AM local time the next day — jet lag is his ally — and talking to startup founders on the East Coast by 5. Before 6:30, he relocates to the offices of Santa Ana-based Collectors. By 7, he’s on the phone back to New York, attending the weekly partner meeting of his new venture capital fund, Operator Partners.
Two hours later, Turner starts his day job: CEO of Collectors, the sports collectibles authenticator he purchased for $850 million in February and took private with other investors. As recently as this spring, Turner wasn’t planning on a quick return to the corner office. The 32-year-old had just stepped down from his role leading Flatiron Health, the electronic medical record company he co-founded, after three years of running it for Roche post-acquisition. Over the summer, however, he got sucked in as his plans proved impossible to implement ad hoc. “It got to the point where they were like, this is your vision, this is your problem,” he says. For a typical venture capital investor, a full-time gig running a 1,000-plus person company across the country from your Manhattan office would mean a quick transition to partner emeritus, or an adviser role. Not at Operator Partners, the fund Turner cofounded with his Flatiron Health collaborator Zach Weinberg and two others last year. At Operator, Turner’s double duty is normal, part of a fresh approach to investing that they claim provides a competitive edge.
In 2020, after years of personally investing in startups, Turner and Weinberg teamed up with two friends, former AdTech entrepreneur Amit Avner and Gil Shklarski, the ex-CTO of Flatiron, to start Operator. They each plunked down enough of their own money to invest a combined $20 million to $25 million in early-stage startups each year. So far, they have written checks to more than 100 companies, across the tech spectrum, but excluding – somewhat ironically — AdTech. They hired two rising stars of the New York venture community, Zach Goldstein and Olivia Benjamin, both Forbes Under 30 alums, to keep the trains running and grow the firm. With no outside capital and few rules, Operator Partners is making waves as a new type of VC firm, where board seats don’t matter, and ownership stakes are flexible. In this financial fringe, billion-dollar funds are friends, not behemoth foes; multi-taskers are valued at a premium.
In 2010, Turner and Weinberg sold their first startup, an ad tech company they’d launched as college students at the University of Pennsylvania’s Wharton School called Invite Media, to Google for $81 million. Both 24 years old, they suddenly had the money — and track record — to find a welcome anywhere in New York’s small tech startup scene, a place where fledgling enterprises like Foursquare, Warby Parker and WeWork were just getting going. Turner and Weinberg began investing in friends and friends-of-friends’ businesses one $25,000 check at a time.
There was little strategy. Gravitating to highly technical, unpolished young entrepreneurs, Turner and Weinberg made early bets on high-growth startups including pet toy subscription service Bark & Co, skilled labor workforce manager Workrise and Medicare provider Clover Health. (The latter’s CEO, Vivek Garipalli, invested in Flatiron and served on its board as a close adviser; he went on an expletive-filled tirade to Forbes in February and has faced an investigation by the Securities and Exchange Commission.)
In 2013, Weinberg heard from Avner, whom he’d befriended at an advertising conference, about another young entrepreneur named William Hockey, who was crashing on Avner’s couch. Hockey and his cofounder Zach Perret’s idea revolved around credit cards; they passed. But a few months later, Hockey and Perret returned to pitch software connecting other online services to someone’s bank accounts, called Plaid. This time, it took Turner and Weinberg only 30 minutes to invest at a $10 million valuation. When Plaid raised fresh funding at a valuation of $13.4 billion this past April, their holding stood at a 1,300x unrealized gain. “We’re stupid sometimes,” Weinberg jests about initially passing. “A lot of early-stage startup investing is just doing it, just being there.”
Then, they mostly stopped. The reason: the rigors of running Flatiron Health, the startup they launched themselves in 2012 as a dashboard to sit on top of electronic health records at hospitals and doctors’ offices. In 2014, they took the bold step to acquire their own medical-records company, expanding Flatiron’s employee base from 17 employees to 135. Investors including GV, BoxGroup and First Round poured in $130 million to help fuel the purchase. With so much now at stake, diverting precious hours to other people’s startups didn’t seem right — to the founders they backed, nor their own investors and employees. When they sold Flatiron to Roche three years ago for $1.9 billion, however, Turner and Weinberg decided they were ready to jump back in — this time with more money, more cachet and, as young fathers, a better handle on how to multitask. They reconnected with Avner, an Under 30 alum from the class of 2014 for his social audience startup Taykey, which he sold in December 2017. After a few months of skiing and traveling, Avner was in negotiations with a handful of established venture capital firms about joining them as an investor — a prospect Turner and Weinberg were also considering. The three chose a different option: To join forces and play by their own rules, to be the kinds of investors they would want themselves as entrepreneurs.
Adding Shklarski, who knew Avner from their time together in the Israel Defense Forces, the four partners settled on a few guiding principles. They’d be investors that founders could contact at any time or hour. They’d make a constant stream of introductions to potential customers and hires they knew or met.
To bring some traditional VC firm rigor to their process, they tapped Benjamin and Goldstein, both 29, and already rising stars at Bain Capital Ventures and Union Square Ventures. Their marching orders: “bottle up the magic” of Operator’s highly successful, but unorthodox, founding partners, even as they unabashedly pursued other projects.
In an industry famous for irregular schedules, Operator pushes the envelope. Aside from a weekly team call, Operator’s partners function semi-independently, checking in over WhatsApp, Telegram and Zoom. Entrepreneurs don’t book time with Operator’s partners through executive assistants — they just text, learning first-hand what types of questions merit an instant response. Turner and Weinberg read pitches during lunch and over the weekends to keep their evening two hours of no-phone time with their young children sacrosanct. Asked his weekly routine, Weinberg demurs: “It varies wildly, which is actually the interesting part.”