📖 Venture Chronicles - October 2025

Colossus published a great portrait of Josh Kushner who founded Thrive Capital. - Colossus

• “In 2010, Thrive’s first fund was $5 million, and included companies like Kickstarter and GroupMe; by 2023, its eighth fund was $3.3 billion, including a maniacally concentrated $2 billion investment in Stripe at a $50 billion valuation, and a $150 million check to OpenAI at a $29 billion valuation.”

• “Along the way, Thrive’s bets on Instagram, Spotify, Warby Parker, Skims, GitHub, Slack, Robinhood and other companies had become conspicuous for being prescient, aesthetic, and exquisitely timed (among its mostly vindicated admirers), or for being absurdly priced, momentum-chasing, and too highly concentrated in dysfunctional businesses with unproven returns (among increasingly sheepish critics).”

• “it was a stage-, geography-, and sector-agnostic venture firm that would concentrate all its investments in a very small number of companies; that it was not only an investment firm but also itself a company; that it incubated its own companies as well as invested in others; and that it didn’t just invest and incubate but functioned as a service provider, product creator, and embedded operational commando unit for founders.”

• “As a child, I was surrounded by the impossible. Just this group of people who came from the ashes and built a beautiful life.”

• “Kushner was a freshman at Harvard when, in the fall of 2004, Mark Zuckerberg dropped out to work full-time on his company, TheFacebook.com. Initially a major in government, Kushner became part of the wave of students who started companies in their dorms. His junior year he started Vostu, a social network for users in Latin America. After graduating, he took a job buying distressed debt at Goldman Sachs, then went back to Harvard for his MBA, all of which confirmed his suspicion that he liked building companies and disliked banking and school.”

• “Kushner said that he wanted to start two new companies, Oscar Health and Thrive Capital, and didn’t want to also remain a student just to mail it in. “Anybody who’s crazy enough to think they can start two companies at the same time is already doing one thing too many.””

• “I went to the HBS library, and sure enough it was empty except for one person. It was Josh. He was working on Thrive and Oscar, and we connected and chatted about this idea of building as well as investing, which has always been part of our DNA.”

• “They discussed how the internet, software, data, and design seemed to be transforming nearly every industry except for healthcare, perhaps the most important sector to consumers from both a human and financial standpoint, and which in any case accounts for nearly a fifth of US GDP.”

• “Kushner, with no prior experience in health insurance, built a company that by 2025 had 1.8 million members and $12 billion in revenue.”

• “Part of the answer can be found in Thrive, which Kushner started at the same time as Oscar, when he was 24.”

• “Josh was told he’d need to convince Joel Cutler, the startup’s main backer at venture firm General Catalyst. After meeting Kushner, Cutler gave him $1 million to seed Thrive.”

• “Kushner pitched him on his seemingly unwieldy idea for Thrive: an opportunistic vehicle agnostic to stage, sector, or geography, which viewed itself as an enabling technology for the world it wished to see, and which had the capacity to not just invest in companies but to build them.”

• “The idea of having a fund that could build companies, invest in companies, invest in them early or late, and inside or outside the US, it was just deeply unconventional.”

• “He decides to seed Thrive with $10 million, and then another $30 million shows up, and before you know it we have $40 million for our first institutional fund.”

• “Between Kushner’s initial vision in 2010 and Thrive’s ninth fund, which closed in August 2024, the firm made good on its promise of making very large, very infrequent investments in a very small number of companies—a portfolio featuring a dizzying ratio of misses to hits, the latter including Instagram, Twitch, Stripe, GitHub, Slack, Robinhood, Hims, Skims, Anduril, OpenAI, Wiz, A24, Databricks, Cursor, and Isomorphic Labs, with Thrive partners on the boards of many. By 2024, the firm reportedly managed $25 billion in assets.”

• “Many of Thrive’s earliest victories bear Kushner’s distinct imprint, such as its early $12 million investment in a growth round of Instagram, 72 hours before Facebook acquired the company for double its $500 million valuation—a ruthlessly competitive allocation the nascent Thrive only won as a result of Instagram founder Kevin Systrom’s belief that Kushner was harder working and more independently minded than other, much larger VCs fighting to get in.”

• “There was the 2012, $6 million investment in a growth round of the Stockholm-based Spotify out of a $150 million fund, an allocation Kushner had regarded as a favor until learning, nearly a decade later, that Spotify’s CEO, Daniel Ek, was in need of exactly $6 million to close the round.”

• “Many spoke of their recruitment, a nine-month courtship that ended with them suddenly working at Thrive without quite knowing when it had become official.”

• “They make investment and most other decisions as a team, and that no individual name gets attributed to any deal.”

• “Grimshaw became Thrive’s best “bottom-up” thinker—the one who likes scraping company websites, court documents, and obscure historical investment memos in his free time—helping build up, among other things, its portfolio of developer tools.”

• “In early 2015, when Grimshaw was 23, he saw GitHub as a potential crown jewel in the portfolio, and began pushing it at an 11pm investment meeting.”

• “By mid-year, they’d decided to invest 7% of Thrive’s $400 million fund into the company. Shortly after they wired the money, Chris Wanstrath, GitHub’s founder and CEO, fired the CFO, head of product, and head of marketing in the wake of a sexual harassment scandal. The immediate consensus in Silicon Valley was that the company was not just a slow grower but a dysfunctional dumpster fire and not going to make it. Thrive’s phones were ringing off the hook with LPs asking if 7% of the fund was going to zero.”

• “Thrive immediately dispatched Mallick to GitHub, which no longer had a CFO, head of product, or head of marketing, but still needed to finalize its budget, set up analytics, and operationalize its go-to-market strategy. During his first nine months at Thrive, Mallick flew back and forth between New Jersey and San Francisco and effectively served as GitHub’s interim CFO.”

• “In the process of setting up its analytics and finalizing its budget, Mallick had more of a front-row seat to GitHub’s business than anyone, and concluded that despite its recent troubles, the company wasn’t just growing but that the growth rate was accelerating. Less than a year prior, Thrive had bought shares of GitHub at a $2 billion valuation; after Mallick’s time embedded with the company, they invested another $120 million across two tranches at a 25% discount.”

• “We’d already been investors in Stripe since 2014, we knew the business really well. But that was how the largest check we’d ever written started. It was nearly $2 billion, and we helped them raise another $5 billion”

• “Zaki helped realize Thrive’s early aspiration to be sector- and geography-agnostic, demonstrated by investments like Nubank and Robinhood, and the three unicorns he co-founded and incubated at the firm: Cadence, Rightway, and Cedar.”

• “The idea that you could make money backing a new brokerage, bank, credit card company, or health insurance company was a foreign concept. We were early to the idea that tech wasn’t this sector isolated from commerce and services.”

• “By 2023, Stripe’s earliest employee options were approaching expiration; if the company didn’t raise several billion dollars or go public, its employees would face a tax bill to the tune of $2–3 billion in ordinary income taxes on $5 billion worth of shares.”

• “Over dinner in Paris, Kushner and Hankes asked Collison to lay out his conundrum. When he explained the quantum of capital Stripe needed in order to avoid going public—something approaching $7 billion—Kushner and Hankes said they’d anchor the round with nearly $2 billion from Thrive and its LPs, then help raise the rest. Shortly after, Kushner and Zaki flew to Patrick Collison’s home with the term sheet, which Hankes referred to as one of Thrive’s “formative investments.””

• “We’re never out there talking our own book,” Hankes said of also having to raise the extra $5 billion. “We do our own work, we get to know the team really well, we have our own conviction, and we invest and do our own thing. But this time, we had to go pitch all these investors to raise several billions of capital.”

• “John Collison’s response was decisive: he took over as CFO, and within 12 months brought Stripe from break-even to nearly 20% margins. “John in that period was founder mode before founder mode.””

• “Thrive’s bet paid off quickly. After burning cash and growing slowly throughout 2022, Stripe cut costs and grew over 25% in 2023; secondary shares that were trading at $50 billion started trading at $65 billion. By September 2025, Stripe was valued at $107 billion.”

• “After quickly deciding they wanted to invest [in Wiz], Kushner and Clark flew to Israel 48 hours later. Due to active hostilities in the country, including ballistic missile attacks on Tel Aviv, the country’s airspace was closed, which required them to fly to Paris, then Cyprus, then take a puddle hopper to Tel Aviv. Arriving at 7pm, they went directly to a four-hour meeting with Rappaport and his co-founder, where they agreed on a deal.”

• “There were no other venture investors in Tel Aviv at the time, because why would you go to a war zone?” Clark remembered. “But our viewpoint was if our founders are there, we should be there, so that’s where we’re going. Josh always had a line to me when I joined Thrive, which is that the people who win deals are the ones who want to win them most. The deal resulted in a $1 billion stake for Thrive after leading Wiz’s final two rounds—one at a $12 billion valuation, the other at $16 billion in an employee tender—before the company was acquired by Google, a year later, for $32 billion.”