Invest Like the Best with Patrick O'Shaughnessy

My guest today is ⁠Gokul Rajaram⁠, Founding Partner at Marathon Management. Gokul is one of the most prolific product builders and investors of the last twenty years. He has built the core ad and product businesses at Google, Facebook, Square, and DoorDash, working at each company during its most formative scaling periods.

Alongside his operating career, Gokul has invested in more than 700 companies, giving him an unusually broad view into how products are built and scaled.

This conversation is about how product building is changing with AI. We discuss the one thing Gokul believes is truly future-proof in AI, why companies like Zendesk and Slack are more exposed than Salesforce or NetSuite, and the only sources of defensibility. 

We also talk about everything Gokul has learned from helping build the most important ads businesses, including the only three ways an ad business can make money, how those constraints shape product decisions, and what consumer behavior change threatens every major platform.

Gokul shares lessons from working closely with Larry and Sergey, Mark Zuckerberg, Jack Dorsey, and Tony Xu.

Please enjoy my conversation with Gokul Rajaram.

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. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus.

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠Vanta⁠. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠. 

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This episode is brought to you by ⁠Rogo⁠. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at ⁠Rogo.ai/invest⁠.

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This episode is brought to you by⁠ ⁠WorkOS⁠⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠ ⁠WorkOS.com⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months.

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠.

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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

(00:00:53) Meet Gokul Rajaram

(00:02:05) How Product Development is Changing with AI

(00:07:32) Philosophy of Product Management

(00:10:19) What is Future-Proof in AI Era

(00:11:25) Building AI Applications Today

(00:15:03) Systems of Record vs Agent Companies

(00:16:58) Which Legacy Software Companies Are Most Exposed

(00:22:15) Stickiness in the AI Era

(00:24:10) Learning from Larry Page and Sergey Brin

(00:28:15) Learning from Mark Zuckerberg

(00:31:31) Learning from Jack Dorsey

(00:35:40) The Art of Great Product Design

(00:36:49) Weekly CEO Communication

(00:40:27) Three Ways to Succeed in Advertising

(00:44:27) What Should Scare Major Ad Platforms

(00:48:24) North Star Metrics

(00:50:09) Self-Serve Products

(00:54:50) Careers in the AI Era

(00:59:03) Stay Long Enough to Have Impact

(01:00:10) Founder Authenticity and Superpowers

(01:02:21) Navigating the Idea Maze

(01:03:42) Role of Boards

(01:06:31) Excellence in Customer Acquisition 

(01:09:11) The Kindest Thing

This week is a special episode. Only David Senra could get me to be on the other side of the mic. Because I don’t plan on being interviewed often, I wanted to share this conversation, which I so enjoyed, with our audience.

It went in a very different direction than I expected. We barely talk about investing or interviewing. Instead, we talk about finding an organizing principle for life, undiscovered talent, and the idea that “the reward for good work is more work.”

We also discuss the principles that guide how I think about building Invest Like the Best, Colossus, and Positive Sum.

This conversation was originally recorded and released on David Senra, and I wanted to share on the Invest Like The Best feed as well. Please go follow what he’s doing, there’s no one like David.

Enjoy!

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. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus.

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest. 

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This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at Rogo.ai/invest.

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This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months.

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com.

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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

(00:04:26) Intro

(00:05:14) The Joy of Championing Undiscovered Talent

(00:07:33) How One Tweet Changed David's Life

(00:10:16) The Upanishads Passage That Shaped Patrick's Worldview

(00:15:32) Growth Without Goals 

(00:17:24) Why Media and Investing Are the Same Thing

(00:33:05) The Search for True Understanding

(00:35:36) The Daniel Ek Dinner That Launched David’s Podcast

(00:39:02) Making Your Own Recipe From the Ingredients of Great Lives

(00:43:46) The Privilege of a Lifetime Is Being Who You Are

(00:52:06) Bruce Springsteen

(00:57:23) Clean Fuel vs Dirty Fuel: The Source of Your Ambition

(01:01:43) The Unfair Advantage of Podcasting

(01:04:12) Relationships Run the World

(01:11:10) The Origin Story of Invest Like the Best

(01:12:45) Building Colossus: Why Start a Magazine in 2025

(01:18:42) People Are More Interested in People Than Anything Else

(01:22:12) Hiring Through Output

(01:26:23) Learn, Build, Share, Repeat

(01:30:01) The Daisy Chain: How Reading Books Led to Everything

(01:33:15) Red on the Color Wheel: Sam Hinkie's Observation

(01:40:17) Finding Your Superpower and Becoming More Yourself

(01:45:06) Repetition Doesn't Spoil the Prayer: Teaching as Leadership

(01:48:11) Life's Work: A Lifelong Quest to Build Something for Others

(01:52:00) The Ten Roles Game and What Matters Most

(01:59:12) Husband, Father, Grandfather

(02:01:52) The Kindest Thing

My guests today are Tom Digan and Greg Stewart. Tom is the co-founder of Ladder, and Greg is its CEO.

Ladder was my first angel investment. What followed over the next seven years is one of the most unlikely and dramatic business stories I’ve been a part of.

Today, Ladder is the number one grossing fitness app in the App Store, approaching $100M in ARR with more than 300,000 paying members. But the path from near death to dominance involved debt collectors, leadership changes, and a full reset during the pandemic.

Tom and Greg built Ladder by being relentlessly empirical about their customers, ruthless about prioritization, raising money wherever they could, and doing whatever it took when most founders would have quit.

We cover the messy early years when survival meant negotiating creditors, how they found PMF by reading thousands of app store reviews, and how they built a TikTok growth engine with no performance marketing experience.

They share their long-term vision for becoming the category winner for health and fitness and the impact of AI and GLP-1s on their business.

This is a conversation about how hard it really is to build something valuable, told by two people who lived through all of it.

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. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus.

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest. 

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This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at Rogo.ai/invest.

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This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months.

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com.

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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 

(00:04:26) Episode Intro

(00:05:45) Ladder: The #1 Fitness App

(00:09:28) The Messy, Early Years

(00:14:47) Sponsors

(00:16:20) The Darkest Point

(00:18:17) Why Greg Joined Ladder

(00:19:45) The Turning Point: Ladder 2.0

(00:21:57) The Key to Negotiating with Creditors

(00:23:16) Fundraising Challenges and Strategies

(00:25:50) Developing Ladder Teams

(00:31:31) Listen to Your Customers

(00:32:57) Launching Nutrition

(00:38:53) Sponsors

(00:39:31) Don’t Listen to Investors on Product Feedback

(00:40:18) The Cave Process

(00:43:13) Crossing the Chasm

(00:43:53) How to Crack TikTok

(00:51:10) The Content Frontier

(00:52:07) Controlled Bets at Scale

(00:54:19) Why you should Build a B2C Company

(00:57:37) The Impact of AI and GLP-1s

(01:02:32) Sponsors

(01:02:53) Staying Focused on the Core Product

(01:05:00) Building the System of Record for Health and Fitness

(01:09:45) What It’s Like Talking to Investors Now

(01:12:32) The Kindest Thing

My guest today is Reed Hastings, the co-founder and former longtime CEO of Netflix.

Netflix is an example of two ideas that everyone talks about, but are extremely hard to do in practice. The first is finding a simple idea and taking it extraordinarily seriously. Reed talks about how even the DVD business was nothing more than a stepping stone toward streaming, which they envisioned from the company’s inception in 1997. The second is talent density, and what it actually takes to set and sustain an exceptionally high bar over decades as a company grows. 

We talk about how those ideas shaped Netflix’s culture and strategy, what Reed learned from mistakes like Qwikster, and why Netflix treated content like a venture portfolio.

We also discuss Reed’s work today. He shares how he’s thinking about AI, what he’s learned from serving on the boards of Microsoft, Meta, Anthropic, and Bloomberg, and what excites him about Powder Mountain, the ski resort he acquired after Netflix.

Please enjoy my conversation with Reed Hastings.

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. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus.

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest. 

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This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at Rogo.ai/invest.

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This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months.

-----

This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com.

-----

Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠).

Timestamps

(00:00:00) Sponsors

(00:03:33) Welcome to Invest Like The Best

(00:04:29) Intro

(00:05:43) Sponsors

(00:07:16) The Concept of Talent Density

(00:11:19) Evaluating Talent

(00:13:47) Managing on the Edge of Chaos

(00:14:51) Why Netflix Gave Large Severance Packages

(00:16:37) The Keeper’s Test

(00:17:07) The Qwikster Mistake

(00:19:15) The Informed Captain

(00:20:39) How to Come Up with Good Ideas

(00:22:32) Transitioning to Streaming

(00:23:05) Being on the Board of Facebook, Microsoft, Anthropic & Bloomberg

(00:26:25) The Role of a Board Member

(00:29:37) Sponsors

(00:30:15) Why Netflix Had Open Compensation

(00:32:04) Netflix’s Content Strategy

(00:37:52) Competing with YouTube and Traditional TV

(00:39:23) Creating Hit Content

(00:40:02) Impact of AI on Netflix

(00:41:24) Innovations in Show Formats

(00:43:23) Sponsors

(00:43:44) Netflix's Technology Backbone

(00:45:29) Expanding into Gaming

(00:46:06) Lessons from Failed Projects

(00:47:30) Financial Strategy and Capital Allocation

(00:50:27) Stepping Down as CEO

(00:50:52) Powder Mountain

(00:56:08) Focus on Education and AI

(00:59:00) Risks and Benefits of AI

(01:00:56) The Kindest Thing

(01:02:56) Sponsors

Today, I am replaying my conversation with Nick Kokonas, one of my favorites from the show.

Nick is the co-founder of 3 of the best restaurants and bars in America - Alinea, Next, and The Aviary as well as the co-founder and CEO of Tock, a comprehensive booking system for restaurants. He majored in philosophy before becoming a derivatives trader and is now one of the most well-known names in the hospitality industry.

In this conversation, Nick shares his experience of bringing a business mindset to the restaurant industry. I'll remember it for why it's so important for a business to really know what it's selling and then actually sell it.

Nick also pulls back the curtain on why restaurants and even book publishers can be great businesses if you do them the right way. I felt like this conversation could have gone on for hours and I hope you enjoy it.

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. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ramp.com/invest to sign up for free and get a $250 welcome bonus.

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform.

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This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster.

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Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠).

Timestamps:

(00:00) Welcome to Invest Like The Best

(03:58) Intro to Nick Kokonas

(4:36) – Why it’s so important to own something

(6:09) – Make decisions that have outcomes

(8:34) – His interest in the restaurant business

(10:28) – Why restaurants are so tough

(13:39) – How their business mindset changed their running of the restaurant

(16:09) – Words they would avoid in the restaurant

(17:53) – Asking the right questions in the restaurant business

(22:14) – Importance in taking the right risks

(23:36) – Coming up with innovative strategies for ticketing, selling meals ahead of time, and dynamic pricing

(31:42) – Can dynamic pricing be extended to other businesses

(32:54) – Origin of Tock

(37:51) – Early days of Tock and identifying the right customers/challenges

(43:07) – Importance of the first customer

(45:56) – The typical restaurant business model

(50:57) – Lessons from Tock and the importance of knowing what you’re selling

(55:21) – Lessons from publishing

(57:18) – Other aspects of business that people know but do nothing about

(1:01:53) – Their response to Covid and lessons learned

(1:09:17) – The real impact to the food delivery companies

(1:10:58) – How businesses communicate their end processes to their customers

(1:15:41) – The Kindest Thing