Josh Kushner is the founder and managing partner of Thrive Capital, which he started in 2011. The firm now manages approximately $50 billion with a deliberately small investment team. Patrick O'Shaughnessy is the CEO of Positive Sum and host of Invest Like the Best.

This conversation covers Thrive's iconic investments including Instagram, Stripe, GitHub, and OpenAI, exploring how the firm's concentrated, high-conviction approach has defined their success. Kushner discusses his investment philosophy influenced by Meditations by Marcus Aurelius and THE FOUNTAINHEAD, and how Peter Thiel's concepts from Zero to One inform their thinking about monopolies and scale advantages.

The discussion delves into Thrive's culture of small teams, their three-category focus for AI investments, and the creation of their holdings business for AI transformation. Kushner shares personal stories about his Holocaust survivor grandmother and formative lessons from mentors like Stan Druckenmiller and John Winkelried.

Building Culture Through Concentration and Small Teams

Thrive maintains a small investment team despite managing $50 billion, believing 'the only way to have a team is to have a small team, and the only way to have a small team is to have a group of people that everyone mutually respects.'

Drawing from Meditations, Kushner emphasizes being 'the same man in both good times and in bad times,' maintaining consistent values regardless of external validation or criticism.

The firm looks for people who are 'either first-generation at Thrive or from the most hated state in the country, New Jersey' - those with a chip on their shoulder but who've transitioned from proving something to others to genuine passion.

Iconic Investments and Concentration Philosophy

GitHub investment in 2014 for $20 million became formative when Thrive was the only buyer of founder shares during leadership transitions, eventually owning about 10% when Microsoft acquired the company.

After Instagram's quick exit, John Winkelried called with advice: 'I'm going to give you the greatest lesson that you'll ever get from me, which is never believe your own bullshit' - Josh put this on post-it notes on every employee's computer.

Stan Druckenmiller's guidance on concentration during market criticism: 'That's always the right decision. You just better fucking pick right' - reinforcing Thrive's high-conviction approach.

Stripe investment of $1.8 billion at $50 billion valuation was viewed as obvious long-term bet: 'It's much easier to predict what is going to happen in the long term than it is in the short term.'

OpenAI Partnership and AI Investment Strategy

Kushner's ChatGPT preview moment: sitting at kitchen table at 1-2 AM, showed wife Carly and said 'this was going to change the world' - led to leading OpenAI's $29 billion round.

OpenAI criticism focused on 'LLMs would get commoditized, the world would move towards open source, all the value would get created at the application layer' - Thrive believed the opposite.

Thrive's three AI investment categories: AI-native businesses (labs, domain-specific models, applications), infrastructure that benefits from AI (Databricks, Stripe, Wiz), and holdings for AI transformation.

Sam Altman called Kushner at 2 AM for engineer recruitment help - Kushner got on phone with IC engineer at 2:30 AM, candidate signed, demonstrating 'willing to do whatever we need to do to be in service.'

Holdings Strategy and Competitive Moats

Holdings represents Thrive's attempt to build defensible advantages: 'If we are a company and we have a product, what are the products that we can create that make us look more like the businesses that we ultimately invest in.'

The insight that 'disruption will happen from inside out' rather than outside-in, because 'you need both the data that is proprietary to the company, but also the experts that exist at the company to fine-tune the model.'

Created permanent capital vehicle to buy and transform businesses with AI, holding them forever: 'if you actually have a differentiated, unique lens and cost of capital around these businesses... you ultimately want to hold on to them forever.'

Personal Philosophy and Formative Influences

Kushner's Holocaust survivor grandmother Ray escaped Belarus ghetto by digging 600-foot tunnel with spoon, lived with Belsky partisans: 'nothing I will ever accomplish in life will be greater than what she pulled off.'

THE FOUNTAINHEAD influence: admires Howard Roark's unwavering commitment to craft and values, particularly the trial scene where 'he's asked to defend himself and he refuses to... totally unwilling to compromise his values.'

Perspective from grandmother's story: 'nothing I will ever go through in life will be as hard as what she went through' - provides context for handling business stress and difficult situations.

The watch story: robbed in Guatemala, thief returned his cheap Swatch after examining it - 'I'll never wear another watch' - symbol of staying grounded regardless of success.