Josh Kushner - Concentration and Conviction - [Invest Like the Best, EP.459]
This is my second conversation with Josh Kushner, founder and managing partner of Thrive Capital.
I recorded this conversation in October after publishing the Colossus cover story about him and Thrive. Given the overwhelming response, we created some breathing room before releasing it.
Josh started Thrive in 2011. The firm now manages approximately $50 billion with a very small investment team. What makes Thrive different is how concentrated they are and how involved they get with their portfolio companies.
We cover the iconic investments that defined Thrive: Instagram, Stripe, GitHub, and spend a lot of time on OpenAI. Josh explains how Thrive thinks about investing today and the three categories they're currently focused on.
Josh also talks about building the firm, why they keep the team small, and what he's learned from A24 about enabling artists to do their best work.
He shares personal stories that shaped him, including his grandmother's experience surviving the Holocaust, and lessons from Stan Druckenmiller, Jon Winkelried, and others at formative moments in Thrive's history.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).
Timestamps:
(00:00:00) Welcome to Invest Like the Best
(00:02:43) Intro: Josh Kushner
(00:03:46) How Thrive Has Changed Since 2023
(00:05:18) Thrive’s Entrepreneurial Culture
(00:12:22) The Power of Small Teams
(00:13:35) Sponsors
(00:14:35) Concentration as Differentiation
(00:16:16) The Github Deal
(00:18:08) Lesson from Stan Druckenmiller
(00:20:37) Leading Stripe’s $50 Billion Round
(00:23:16) Instagram: Doubling an Investment in Days
(00:25:43) Isomorphic: Thrive as an Enabling Technology
(00:27:04) Thrive & A24
(00:28:19) OpenAI: The Product Josh Couldn’t Unsee
(00:32:09) Pricing the OpenAI Investment
(00:33:40) OpenAI and Power
(00:35:26) Finding Joy in Hard Work
(00:39:15) Inside View of the Tech & AI Landscape
(00:42:28) Three Investment Categories Thrive is Focused On
(00:44:37) Thrive Holdings: Inside-Out Disruption
(00:48:54) Competition in Venture
(00:50:49) Sponsors
(00:51:48) Thrive’s Immutable Values
(00:54:21) A Family Story of Survival
(00:56:43) The American Dream
(00:58:03) What Artists Can Teach Investors
(01:00:26) Never Compromise Your Values
(01:01:33) The Story Behind Josh’s Forever Watch
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman
Krithika Shankarraman was the first marketing hire at OpenAI and Stripe and led marketing at Retool. At OpenAI, she established marketing foundations for ChatGPT for consumers and enterprises, as well as their developer API platform. While at Stripe, she spent over eight years building and scaling their marketing function from scratch. An engineer turned marketer, Krithika brings a uniquely analytical approach to marketing. She currently serves as Entrepreneur in Residence at Thrive Capital, where she helps portfolio companies on all things marketing.
What you will learn:
1. Why do most marketing playbooks often fail, and what’s a better way?
2. Which marketing lever should I pull first?
3. Why is trying to be better than competitors usually a losing strategy?
4. How do I craft positioning that actually converts?
5. What makes messaging stick with developers, enterprises, and consumers?
6. What pricing experiments actually move revenue?
7. What is working at OpenAI really like?
8. Why does consistency and quality matter more than speed?
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Where to find Krithika Shankarraman:
• X: https://x.com/krithix
• LinkedIn: https://www.linkedin.com/in/krithix/
• Website: https://krithix.com/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Krithika
(04:22) Early marketing lessons from OpenAI
(11:17) Diagnosing marketing needs
(15:06) The DATE framework and why being cheaper is a race to the bottom
(17:11) Marketing strategies at Retool
(22:29) Insights from marketing at Stripe
(32:33) The importance of consistent marketing communication
(39:55) Criteria for hiring a marketing expert
(41:43) “Capital M” vs. “lowercase m” marketing
(43:05) ChatGPT vs. Claude: market dominance
(45:31) The future of AI and its societal impact
(47:09) Work-life balance
(48:41) Transitioning to Thrive
(52:35) Career advice for marketers
(55:00) The importance of taste and creativity in the AI era
(01:00:04) AI product pricing
(01:03:21) AI tools in marketing
(01:05:17) Failure corner
(01:08:46) Lightning round and final thoughts
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Referenced:
• OpenAI: https://openai.com/
• Stripe: https://stripe.com/
• Retool: https://retool.com/
• Dropbox: https://www.dropbox.com/
• Sam Altman talks about his business model: https://www.youtube.com/watch?v=pLnyjxgFxew
• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan
• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy
• Netflix: https://www.netflix.com/
• Stripe Connect: https://stripe.com/connect
• John Collison on X: https://x.com/collision
• Patrick Collison on X: https://x.com/patrickc
• Cristina Cordova on LinkedIn: https://www.linkedin.com/in/cristinajcordova/
• Hackpad: https://en.wikipedia.org/wiki/Hackpad
• Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg
• Wiz: https://www.wiz.io/
• Thrive Capital: https://thrivecap.com/
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• Claude: https://claude.ai/new
• ChatGPT: https://chatgpt.com/
• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics
• Databricks: https://www.databricks.com/
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai
• April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning
• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting
• Severance on AppleTV+: https://tv.apple.com/us/show/severance/
• Granola: https://www.granola.ai/
• Some people think AI writing has a tell—the em dash. Writers disagree: https://www.washingtonpost.com/technology/2025/04/09/ai-em-dash-writing-punctuation-chatgpt/
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Recommended books:
• Obviously Awesome: How to Nail Product Positioning So Customers Get It, Buy It, Love It: https://www.amazon.com/Obviously-Awesome-Product-Positioning-Customers/dp/1999023005
• Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327/
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Josh Kushner - Building Thrive Capital - [Invest Like the Best, CLASSICS]
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are N of one conversations with N of one people. This is a rare opportunity to hear from one of the best investors of the past decade—Josh Kushner, founder and managing partner of venture firm, Thrive Capital.
Josh started Thrive in 2010 and launched its first institutional fund in 2011. That first institutional fund was $40 million and, in it, Thrive led Warby Parker’s Series A, invested in Instagram, and incubated a business, which Josh co-founded, called Oscar. Their portfolio is stage agnostic and their track record includes many of the best known businesses from the past decade, including Spotify, Unity, Stripe, and Twitch among many more. Please enjoy my great conversation with Josh Kushner.
Subscribe to Colossus Review.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Follow us on Twitter: @patrick_oshag | @JoinColossus
Show Notes
(00:00:00) Welcome to Invest Like the Best
(00:05:14) Why do this podcast
(00:08:14) The development of taste and quality
(00:12:20) CS Lewis tweet; The Inner Ring
(00:18:14) Overview the founding story of Oscar Health
(00:25:18) Learning to identify good problems and creating a business to solve it
(00:27:43) The birth story of Thrive Capital
(00:32:14) Lessons learned from creating the first three Thrive funds
(00:39:44) Talent, recruiting and seeing potential in younger generations of people
(00:47:40) Investments he made during the early foundation of Thrive that had significant impact
(00:51:12) His analogy for investing in early versus late stage and styles of real estate investing
(00:56:22) The current macro environment
(01:00:57) Why he sold small stakes of Thrive
(01:05:10) His philosophy on what makes a good product
(01:10:10) His absence from crypto and why he refrained during the boom in 2021
(01:12:33) Thoughts about the opportunity set in FinTech today writ large
(01:15:39) Lessons learned from his time spent with Marc Andreessen
(01:17:43) Lessons learned from Stan Druckenmiller, Henry Kravis, and David Geffen
(01:22:09) Firm values he thinks are very important
(01:31:15) Vision as a key ingredient for founders
(01:34:19) His view of the investment industry in the world today writ large
(01:44:48) The kindest thing anyone has ever done for him
Kareem Zaki - Small Ideas Attract Competition - [Invest Like the Best, EP.392]
My guest today is Kareem Zaki. Kareem is a General Partner at Thrive Capital and has been at the firm for a decade. In an episode last year, Thrive's founder, Josh Kushner, told me he is the best healthcare investor in the world. Kareem has co-founded three healthcare businesses worth over one billion dollars. He also has expertise in financial services, where he's led the firm's investments in companies like Ramp and Robinhood.
It's a timely moment to have this discussion, with Thrive announcing a new $5 billion fund in August. We talk about how Thrive identifies category-defining companies, what concentration means to them, and how startups should approach the healthcare industry. Please enjoy this great discussion with Kareem Zaki.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest growing FinTech company in history and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. It’s also notable that many best-in-class businesses use Ramp—companies like Airbnb, Anduril, and Shopify, as well as investors like Sequoia Capital and Vista Equity. They use Ramp to manage their spending, automate tedious financial processes, and reinvest saved dollars and hours into growth. At Colossus and Positive Sum, we use Ramp for exactly the same reason. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.
Follow us on Twitter: @patrick_oshag | @JoinColossus
Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).
Show Notes:
(00:00:00) Welcome to Invest Like the Best
(00:06:02) Early Days and Consistent Strategy
(00:07:10) Personal Journey and Reconnecting with Josh
(00:08:36) Investing Philosophy and Strategy
(00:11:04) Building a Supportive Structure
(00:12:10) Generalist Approach and Market Trends
(00:13:45) Life Cycle Investing and Concentration
(00:16:16) The Builders Mentality
(00:17:52) Raising a Huge Fund and Its Implications
(00:20:40) Understanding Category Defining Companies
(00:37:48) The Changing Nature of Investment Categories
(00:49:03) Evaluating Business Durability and Market Quality
(00:51:30) Understanding Healthcare Challenges
(00:53:46) Approaching Healthcare Innovation
(00:59:18) The Role of Competition in Healthcare
(01:04:17) AI's Transformative Potential
(01:07:35) Advice for Aspiring Entrepreneurs
(01:09:46) Thrive's Investment Philosophy
(01:22:55) The Kindest Thing Anyone Has Ever Done For Kareem
Visa Follow-Up and Today’s Payments Ecosystem (with Gaurav Ahuja)
We’re joined by Imprint cofounder and Thrive General Partner Gaurav Ahuja to dive deeper into the modern payments ecosystem and Visa’s current place within it. Gaurav was one of our research sources for the Visa episode, and we wanted to bring his insights to you all too. We discuss whether Visa really should be worried about eroding interchange fees, the impact of realtime payments systems, opportunities for startups and whether the Visa / Mastercard duopoly could really be overthrown. Tune in and enjoy!
Links:
https://www.federalreserve.gov/paymentsystems/files/Avg_IF_by_PCN.pdf
Sponsors:
Sierra: https://bit.ly/acquiredsierra
Josh Kushner - Building Thrive Capital - [Invest Like the Best, EP.337]
My guest today is Josh Kushner, founder and managing partner of venture firm, Thrive Capital. Josh started Thrive in 2010 and launched its first institutional fund in 2011. That first institutional fund was $40 million and, in it, Thrive led Warby Parker’s Series A, invested in Instagram, and incubated a business, which Josh co-founded, called Oscar. Thrive has gone from strength to strength since then and now manages $15 billion with a small team of 9 investors. Their portfolio is stage agnostic and their track record includes many of the best known businesses from the past decade, including Spotify, Unity, Stripe, and Twitch among many more. Josh rarely speaks in public about the firm and their philosophy so it was a blast to do this with him. Please enjoy my great conversation with Josh Kushner.
Founders Podcast
Founders Episode 136 - Estee Lauder
Founders Episode 288 - Ralph Lauren
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Follow us on Twitter: @patrick_oshag | @JoinColossus
Show Notes
(00:03:14) - (First question) - Why do this podcast
(00:06:14) - The development of taste and quality
(00:10:20) - CS Lewis tweet; The Inner Ring
(00:11:53) - Founders being heroes and motivating quietly from the background
(00:16:14) - Overview the founding story of Oscar Health
(00:21:30) - Is a big business different from a small one
(00:23:18) - Learning to identify good problems and creating a business to solve it
(00:25:43) - The birth story of Thrive Capital
(00:30:14) - Lessons learned from creating the first three Thrive funds
(00:33:35) - Industry wide competition today and models for building a firm in general
(00:37:44) - Talent, recruiting and seeing potential in younger generations of people
(00:45:40) - Investments he made during the early foundation of Thrive that had significant impact
(00:49:12) - His analogy for investing in early versus late stage
(00:54:22) - The current macro environment
(00:57:52) - Giving AI companies computing power instead of money
(00:58:57) - Why he sold small stakes of Thrive
(01:03:10) - His philosophy on what makes a good product
(01:05:20) - What he thinks about the models like Mobile and Cloud
(01:08:10) - His absence from crypto and why he refrained during the boom in 2021
(01:10:33) - Thoughts about the opportunity set in FinTech today writ large
(01:12:04) - Other potential opportunity sets beyond what’s already been discussed
(01:13:39) - Lessons learned from his time spent with Marc Andreessen, Stan Druckenmiller, Henry Kravis, and David Geffen
(01:21:59) - Balancing magnitudes of capital between investment funds
(01:23:32) - Why founders choose Thrive
(01:29:15) - Vision as a key ingredient for founders
(01:32:19) - His view of the investment industry in the world today writ large
(01:40:19) - Other investment firms he would invest in
(01:42:48) - The kindest thing anyone has ever done for him
20VC: The OpenAI Memo: Why Invest? Is it too Late to Catch OpenAI? Are OpenAI's Models Truly Defensible? Does the Value in AI Accrue to Incumbemts or Startups - Application Layer/Infrastructure? What Happens with Regulation? with Vince Hankes @ Thrive
Vince Hankes is a Partner @ Thrive Capital where he has led the firm's investments in OpenAI, Melio, and Airplane.dev. He currently sits on the board of Airtable, Benchling, Lattice, and Melio. Prior to joining Thrive, Vince was an investor at Tiger Global where he learned the craft of venture from the legend that is Lee Fixel.
In Today's Episode with Vince Hankes We Discuss:
1. From Tiger Global to Partner @ Thrive Capital:
How Vince made his way into the world of investing with Tiger Global?
What are 1-2 of his biggest takeaways from working alongside the legendary Lee Fixel?
Why did Vince make the move from Tiger to Thrive? How do the two firms differ?
2. The OpenAI Investment: The Memo:
How did the OpenAI deal come to be? What were the round dynamics?
Market Evaluation: How did Vince and the team analyze the market top down?
Competition: Who did Vince identify as the core competitors to OpenAI?
Defensibility: How did Vince think through the long-term defensibility of OpenAI's model? Does Vince believe these models will become commoditised?
Price: How did Vince and the team get comfortable with the $29BN price?
3. AI: Hype or Generational Defining Transformation:
Trend or Transformation: Why does Vince believe AI will be the defining technology of our generation?
Startup vs Incumbent: Does Vince think the value will accrue to the incumbent or the startup?
Open or Closed: Does Vince think we will operate in a closed (one model rules them all) environment or an open-source environment with many models?
AI Talent: Where does Vince think the majority of the best AI talent will concentrate?
Speed: Why would Vince be scared if he were a startup today looking at the incumbents?
4. The Changing Investor: Lessons from Good and Bad:
How has Vince changed most significantly as an investor over time?
What has been his single biggest investing mistake? How did he learn from it?
What has been his biggest investing success? How did that change his mindset?
What has Thrive done in their org structure to allow them to make bets very few other firms can do?
20VC: Thrive Capital's Kareem Zaki on The One Rule That Drives Investment Decision-Making and Focus at Thrive, Why Every Large Institution Will Enter Venture Capital Over the Next Decade and How To Create a Firm Culture That Attracts The Best Young Talent
Kareem Zaki is a General Partner @ Thrive Capital, with a portfolio including Stripe, Instacart, Instagram, Nubank, Github, Glossier and many more, they have cemented their position as one of the leading venture firms of the last decade. As for Kareem, he is a co-founder and board member to Cedar, Nava, Scope Security and Cadence and has invested in the likes of Affirm, Lemonade, Ramp and Trade Republic. Prior to entering venture, Kareem spent 3 years in private equity with Blackstone.
In Today's Episode with Kareem Zaki You Will Learn:
1.) How Kareem made his way from the world of private equity to backing some of the most innovative next-generation companies with Thrive Capital?
2.) Portfolio Construction: What is the one rule that drives all decision-making at Thrive? How does Kareem think about maintaining focus with such a broad mandate? How do Thrive think about asset allocation internally with such a broad mandate? How does incubating companies also help Kareem be a better investor?
3.) Investing Style: How has Kareem's investing style changed over the last 10 years? What does he focus on now that he did not before and visa versa? How does Kareem assess his own relationship to price? Through what lens does Kareem approach market sizing and timing? Where do many investors make mistakes here?
4.) The Landscape: How does Kareem respond to the activity and cadence of Tiger? In what way does Kareem believe the venture landscape will have changed most significantly in the next 10 years? How do the existing incumbent firms need to change in the wake of this? How do Thrive respond to the pace and cadence of check writing today?
Item's Mentioned In Today's Episode with Kareem Zaki
Kareem's Favourite Book: How Will You Measure Your Life
Kareem's Most Recent Investment: Cadence
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