Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups

Josh Kushner graduated from Harvard College in 2008, worked briefly at Goldman Sachs, and started Thrive Capital in 2009 out of New York City. The first fund was $5 million, seeded by General Catalyst co-founder Joel Cutler. Kushner was 24 years old. He did not have a venture capital track record. He had a conviction about where consumer internet was going and a willingness to make highly concentrated bets on founders he trusted.

The low-profile approach was deliberate from the beginning. Thrive's early website featured a single sentence. The firm did not do press interviews. Kushner let his portfolio speak.

The Early Portfolio

Josh Kushner investments at Thrive's early funds showed a consistent pattern: consumer internet companies with network effects, backed at stages where the potential was clear but the outcome was not. GroupMe, a group messaging app, was acquired by Skype one year after Thrive funded it. Twitch, the gaming and live streaming platform, was acquired by Amazon for nearly $1 billion. Instagram was an early Thrive investment before its $1 billion Facebook acquisition. Warby Parker, the direct-to-consumer eyewear brand, went public at a $6.8 billion valuation in 2021.

These exits validated the thesis and funded increasingly large subsequent funds. By 2014, Thrive was raising $400 million funds. By 2023, a single fund was $3.3 billion. By 2024, Thrive IX closed above $5 billion, split between $4 billion for late-stage and $1 billion for early-stage. As of 2026, Thrive has raised $22.3 billion total and manages over $50 billion.

The portfolio across that arc includes GitHub, acquired by Microsoft for $7.5 billion; Figma, which Adobe attempted to acquire for $20 billion before regulators blocked it; Robinhood (public); Affirm (public); Nubank (public); Databricks, valued at $43 billion in 2024; Ramp; Airtable; Plaid; Anduril; and Kim Kardashian's Skims.

The OpenAI Arc

Thrive's most consequential position is in OpenAI. In 2022, when OpenAI was raising capital and receiving limited institutional interest, Thrive invested approximately $130 million at a $29 billion valuation. It was reportedly the only term sheet OpenAI received at that time.

In October 2023, Thrive led a tender offer financing of OpenAI shares at an $86 billion valuation. That same month, OpenAI CEO Sam Altman was fired by the board and reinstated five days later. The first call Brad Lightcap, OpenAI's COO, made when Altman was fired was to Kushner. Lightcap told Fortune that Kushner's response was not about the investment: "It was, 'How are you? How's the company? I'm here for you, I support you guys. What can I do to help?'"

In late 2024, Thrive invested approximately $1 billion in OpenAI at a $150 billion valuation and negotiated the exclusive right to invest another billion at that same valuation through January 2026, effectively a call option on the most valuable private company in history. By early 2025, OpenAI's valuation reached $500 billion. In February 2026, Thrive confirmed it had invested roughly $1 billion more at a $285 billion valuation, per CNBC.

Sam Altman said of Kushner in a public statement: "Extremely grateful to work with Josh. No one could ask for a more committed, more thoughtful, or harder-working investor."

Elizabeth Yin of Hustle Fund has observed that the investors who develop the most durable founder relationships are the ones who treat portfolio companies as people first, not positions first. Kushner's behavior during the OpenAI board crisis is the clearest illustration of that in recent venture capital history. Angel Squad members building founder relationships at the earliest stages start developing that same orientation from their first check. See how at hustlefund.vc/squad.

The Stripe Position and Concentrated Betting

Thrive invested $1.8 billion in Stripe at a $50 billion valuation in March 2023, one of the largest single venture checks written in that period. By September 2025, Stripe's valuation had reached $107 billion. Thrive's $1.8 billion position theoretically doubled in value in roughly 18 months.

The Stripe bet was an extreme expression of Thrive's concentrated portfolio strategy. Most venture funds diversify across 50 or more companies. Thrive intentionally concentrates into fewer, larger positions in companies they know well. That approach generates higher volatility but also generates the kinds of returns that make a $5 million first fund turn into a $50 billion management firm in 15 years.

Shiyan Koh of Hustle Fund has noted that Angel Squad members who understand portfolio concentration as a deliberate strategy rather than a failure of diversification are the ones who generate the most interesting returns over time. The Angel Squad community of 2,500-plus investors across 50-plus countries explores exactly these questions alongside Hustle Fund GPs. Find the community at hustlefund.vc/squad.‍