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In 2024 Brad Jacobs wrote the book How to Make a Few Billion Dollars.
In the book Brad explains how he built 8 separate billion dollar companies and other lessons from his 40+ year career as an elite entrepreneur.
In the two years since Brad has made a few MORE billion dollars and so the sequel to his first book is: How to Make a Few MORE Billion Dollars.
In this episode I share some of Brad's ideas on raising tons of money (Brad has raised over $50 billion), mastering his integration playbook, ideas for organizational integration, org chart design, and how Brad keeps his mind centered and in a positive place to handle the inevitable ups and downs of building great companies.
Episode sponsors:
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Collateral transforms your complex ideas into compelling narratives. Collateral crafts institutional grade marketing collateral for private equity, private credit, real estate, venture capital, family offices, hedge funds, oil & gas companies, and all kinds of corporations. Storytelling is one of the highest forms of leverage and you should invest heavily in it. You can do that by going to https://collateral.com
Bill Gurley spent years on Wall Street, built his career as a partner at Benchmark, worked through Uber’s hypergrowth era, and now serves on the board of the Santa Fe Institute, where he studies complexity and systems thinking.
In this episode, Bill shares the mental models he returns to most, including systems thinking, second- and third-order effects, and the importance of understanding both the bedrock of your field and the bleeding edge.
He explains what separates great founders, why storytelling and product instincts matter, how he uses AI across different models, and what he sees coming in open source, China, stablecoins, tokenization, payments, and venture capital.
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Timestamps:
(00:00) Key Mental Models
(02:02) Investing Journey and Key Players
(05:21) Knowing the Bedrock of the Industry
(08:50) Obsessive Learning in Founders
(10:04) The Silent Edge
(11:44) Surprising AI Use
(13:13) The Future of AI Models
(14:17) Global AI Regulation
(18:12) Impacts of AI on Investing
(19:53) Are There Limitations on Training AI Models?
(23:04) Would You Sit in the Back Seat While Your Tesla Drives?
(24:15) Non-Consensus Opinions
(24:53) Are We Overfunding this Buildout?
(29:40) The Role of Retail Investors and Tokenization
(34:26) What is a Stablecoin?
(37:58) Competitive Mode: Visa and Mastercard
(39:55) AI and Debt Analysis
(45:05) The Craft of Storytelling and Writing
(48:07) Founder Advantage: Product Instinct
(50:12) Real World Lessons from Working With Uber
(52:10) Inside Benchmark’s Success
(59:42) What is Success for You?
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Newsletter: The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter
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Follow Shane Parrish:
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LinkedIn: https://www.linkedin.com/in/shane-parrish-050a2183/
Follow Bill Gurley
LinkedIn: https://www.linkedin.com/in/billgurley/
X: https://x.com/bgurley?lang=en
Check out Runnin’ Down a Dream: How to Thrive in a Career You Actually Love
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In this commencement address to Columbia University's Fu Foundation School of Engineering and Applied Science Class of 2015, Ben Horowitz challenges some of the most common advice given to graduates.
Rather than urging students to “follow their passion,” Horowitz argues that people should focus on developing their strengths and making meaningful contributions to the world. Drawing on stories from his own time at Columbia, the founding of technology companies, and investments in startups like Airbnb, he explores the importance of independent thinking, conviction, and pursuing ideas that others may initially dismiss.
Along the way, Horowitz discusses technological progress, entrepreneurship, opportunity, and why he believes today's graduates are entering a world defined less by unprecedented challenges than by unprecedented possibilities.
ee
Resources:
Follow Ben Horowitz on X: https://x.com/bhorowitz
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Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.
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What if everything you were taught about wealth was designed to keep you stuck?
Lewis Howes spent his mid twenties broke, sleeping on his sister's couch with no degree and no plan. He turned that into The School of Greatness, a podcast nearing 2,000 episodes, and three New York Times bestselling books. He says the real block between you and wealth was never effort.
He walks you through the shift from trading hours for income to building systems that pay you while you sleep, plus the exact kind of room you need to sit in if you want money to start feeling normal instead of stressful.
He also breaks down why one income stream is basically a financial emergency waiting to happen, and the one unexpected money move every wealthy person he has ever interviewed swears by.
By the end you will see exactly why, and how to start applying all of it over the next 30 days.
Lewis' books:
Make Money Easy
The School of Greatness
The Greatness Mindset
The Mask of Masculinity
In this episode you will:
For more information go to https://lewishowes.com/1950
More SOG episodes we think you’ll love:
George Kamel
Jaspreet Singh
Vivian Tu
Get More From Lewis!
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Ed Catmull is the co-founder of Pixar and the former president of Disney Animation.
He grew up in 1950s Utah wanting to animate for Disney. Convinced he couldn't draw well enough, he studied physics and computer science at the University of Utah instead, landing in one of the great talent incubators in computing history. In 1972, he animated his own left hand—one of the first 3D computer renderings ever made. Since childhood he had carried a single ambition: to make the first feature film animated entirely by computer. Reaching it took more than 20 years.
George Lucas hired Catmull in 1979 to build a computer division at Lucasfilm. When Lucas needed cash, Steve Jobs bought that division in 1986 for $5 million and spun it out as Pixar. For years it sold imaging computers and lost money while Catmull and John Lasseter made short films to keep the dream alive. Jobs sank roughly $50 million of his own money into it. In 1995, Pixar released Toy Story, the first feature animated entirely by computer, and went public days later. Finding Nemo, The Incredibles, WALL-E, and Up followed. Disney bought Pixar in 2006 for $7.4 billion and put Catmull in charge of both studios; he revived a faltering Disney Animation with films like Frozen.
Catmull cared about the conditions that let creative work survive its own fragility. Every original idea, he argues, starts out ugly and broken, and management exists to protect it long enough to get good. At Pixar that meant the Braintrust: a room where directors got blunt feedback with no authority attached and the conversation stayed on the problem, never on who was right. He laid it all out in Creativity, Inc.
Show notes: https://www.davidsenra.com/episode/ed-catmull
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Chapters
(00:00:00) Most Companies Are Full Of Shit
(00:04:28) The Brain Trust Mechanism
(00:10:13) Why Steve Jobs Was Banned From The Braintrust
(00:17:48) Your Job Is To Manage The Dynamics
(00:23:27) Betting The Company On Toy Story
(00:24:35) Engineering Eisner's Worst Nightmare
(00:36:51) Bob Iger's Crappy Hand
(00:38:44) Why Disney Never Asked What Pixar Was Doing
(00:43:48) Take The Hard Problem
(00:44:38) The Director Can't Lose The Team
(00:48:48) Quality Is The Best Business Plan
(00:52:32) What Walt Disney Taught Him
(00:59:25) George Lucas And The Motion Blur Problem
(01:08:48) Now What's The Point Of My Life
(01:13:31) How Much Of This Was Me
(01:16:10) George Lucas Wanted The Whole Industry Healthy
(01:25:11) Refusing To Let Anyone Feel Second Class
(01:32:38) The Truck In The Building
Morgan Housel breaks down the exact framework he uses to build wealth, minimize financial stress, and buy freedom.
While most financial advice focuses on how to get rich, Morgan explains why the skills needed to stay rich are completely different.
You will learn why "boring" investing beats complex strategies, how to avoid the social traps that destroy wealth, and the specific equation for finding contentment.
Morgan Housel is a partner at Collaborative Fund and the bestselling author of The Psychology of Money.
Enjoy!
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Approximate Timestamps:
(00:00) Trailer/Introduction
(00:58) What Drives You?
(04:50) What Can Money Do For Us?
(07:22) Happiness vs. Satisfaction
(11:45) Becoming Financially Independent
(14:40) Survival and Contrast
(20:16) Ad Break
(21:05) Investing: Can You Beat the Market?
(22:32) When Is The Right Time To Buy a House?
(26:45) Housing Affordability and Equity
(28:39) Step by Step Investing
(35:08) Eras of Life and Spending In Those Eras
(43:50) Raising Kids With Money
(48:46) Social Media: Expectations and Comparison
(55:46) Lessons From the Vanderbilts
(01:01:21) Learning From Others Spending Habits
(01:07:51) Lessons From History: Depressions, Panics, Downturns
(01:11:40) Net Worth in Cash
(01:14:20) Passive Income and Financial Independence
(01:25:58) Massive Success: Doing It All Again
(01:32:27) What Should You Optimize For?
(01:38:24) What Do You Splurge On?
(01:40:38) What Can History Teach Us About Inflation?
(01:47:46) Index Funds Allocation
(01:53:36) What Is Success For You?
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This episode of the Knowledge Project is for informational purposes only. The views and opinions expressed by Shane Parrish or our guests are solely their own. Nothing in this conversation should be considered investment advice, financial guidance, or a recommendation to buy or sell any security. Always do your own due diligence or consult with a qualified financial advisor before making investment decisions. It's time to listen and learn.
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Psychology of Money: https://geni.us/my3K
Morgan Housel
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Newsletter: The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter------
Follow Shane Parrish:
X: https://x.com/shaneparrish
Insta: https://www.instagram.com/farnamstreet/
LinkedIn: https://www.linkedin.com/in/shane-parrish-050a2183/
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Thank you to the sponsors for this episode:
Granola AI, The AI notepad for people in back-to-back meetings: https://www.granola.ai/shane
Check out the Granola Notes here.
Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.
We discuss:
1. Why “extraordinary results demand extraordinary efforts”
2. Why you should deliberately understaff projects, and how to know when you’ve gone too far
3. Matt’s transition from COO to CPO and what surprised him about leading product
4. The “high alpha, low beta” framework for evaluating people, processes, and products
5. When founders should quit their startups (hint: much earlier than VCs want you to)
6. How to fight entropy in your organization through relentless energy and intensity
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Brought to you by:
Google Gemini—Your everyday AI assistant: https://ai.dev/
Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny
GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny
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Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths
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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation
—
Where to find Matt MacInnis:
• X: https://x.com/stanine
• LinkedIn: https://www.linkedin.com/in/macinnis
• Email: [email protected]
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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 Matt MacInnis and Rippling
(04:38) The importance of extraordinary efforts
(08:37) The challenges and rewards of relentless effort
(10:11) Your job as a leader is to preserve intensity
(12:39) You learn far more from success than failure
(16:34) Transitioning to chief product officer
(19:54) Fixing product management at Rippling
(25:27) The “high alpha, low beta” framework
(28:55) The PQL framework
(35:16) Hiring frameworks and team dynamics
(36:52) A helpful interview tactic
(40:00) Leading as a COO vs. a CPO
(42:34) The reality of product-market fit
(46:38) The problem with venture capital
(49:29) When founders should quit their startups
(41:48) The immutable market
(54:13) Lessons from Notion’s success
(57:43) Investment strategies and narrative violations
(01:00:42) The power of compounding, power law, and entropy
(01:07:02) Maintaining intensity and fighting entropy
(01:11:33) The importance of feedback and escalations
(01:14:31) Rippling’s vision and success
(01:17:48) AI’s impact on SaaS and business software
(01:23:42) AI corner
(01:26:23) Final thoughts and lightning round
—
Referenced:
• Rippling: https://www.rippling.com
• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman
• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill
• Carvana: https://www.carvana.com
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad
• Inkling: https://www.inkling.com
• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari
• Notion: https://www.notion.com
• Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law
• Seeking Alpha: https://seekingalpha.com
• Dennis Rodman’s website: https://dennisrodman.com
• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle
• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick
• SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html
• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1
• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits
• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling
• Workday: https://www.workday.com
• Matic robots: https://maticrobots.com
• Wall-E: https://www.imdb.com/title/tt0910970
• Conviction: https://www.conviction.com
• Mike Vernal on X: https://x.com/mvernal
• Sarah Guo on X: https://x.com/saranormous
• No Priors: https://linktr.ee/nopriors
• Gemini: https://gemini.google.com
• ChatGPT: https://chatgpt.com
• Claude: https://claude.ai
• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier
• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c
• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker
—
Recommended books:
• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595
• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020
• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557
• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
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Lenny may be an investor in the companies discussed.
John Mackey is the co-founder of Whole Foods Market, where he also served as the company's CEO for 44 years (1980–2022). More recently, Mackey is the co-founder of Love.Life, a wellness company focused on a holistic approach to health. He is an entrepreneur, author and advocate for conscious capitalism who spent over four decades building the natural foods industry.
Under his leadership, Whole Foods grew from a single store in Austin, Texas, in 1980 to the world's largest natural and organic foods retailer, with over 500 stores across North America and the United Kingdom before its acquisition by Amazon in 2017 for $13.7 billion.
After dropping out of the University of Texas at Austin, Mackey opened SaferWay Natural Foods in 1978 with Renee Lawson Hardy. He merged SaferWay with Clarksville Natural Grocery in 1980 to create Whole Foods Market. He became known for pioneering high-quality natural foods retail, championing stakeholder-oriented business philosophy and popularizing the concept of conscious capitalism.
His accomplishments include building Whole Foods into a Fortune 500 company, co-founding the Conscious Capitalism movement with Raj Sisodia, serving as CEO of Whole Foods for 44 years until his retirement in 2022, co-authoring "Conscious Capitalism: Liberating the Heroic Spirit of Business" in 2013 and "The Whole Foods Diet" in 2017 and launching Love.Life in 2023 to focus on longevity and integrative medicine.
Episode show notes: https://www.davidsenra.com/episode/john-mackey
Made possible by
Ramp: https://ramp.com
Function Health: https://functionhealth.com/senra
Eight Sleep: https://eightsleep.com/senra
Chapters
(00:00:00) Fanatical Entrepreneurs: Why Work Feels Like Play
(00:02:18) The Missionary vs. Mercenary Co-Founder Conflict
(00:06:16) The Shirtless Hitchhiking Hippie and Johnny Rockefeller
(00:08:12) Entrepreneur Confidence: Solving Puzzles and Cracking the Code
(00:10:19) Flying Under the Radar: How Supermarkets Ignored Whole Foods
(00:10:52) Venture Capitalists Are Hitchhikers With Credit Cards
(00:14:03) Builder Entrepreneurs vs. Serial Entrepreneurs
(00:16:31) Time Is the Only Filter I Trust
(00:20:52) How Walmart Accidentally Fueled Whole Foods' Success
(00:24:01) The Jaw-Drop Effect: When Customers First Walked In
(00:27:17) Growth Through Acquisition: Building Geographic Platforms
(00:29:19) Secret Allies: The Natural Foods Network
(00:33:17) Mrs. Gooch's and the Revelation of Scale
(00:34:52) Missionaries Sharing Financial Statements and Building Friendships
(00:38:10) Never Competing Head-On With Friends
(00:41:22) Going Public and Creating Liquidity for the Network
(00:42:00) Continuous Learning: The Michael Dell Principle
(00:44:10) Steve Jobs and Spotting Markets With Second-Rate Products
(00:46:50) The Joy of Watching Team Members Become Millionaires
(00:48:09) Capitalism: The Greatest Thing Humans Ever Invented
(00:55:59) Cult Brands Are Built by Evangelists
(00:58:01) Passion Is Infectious: The Reality Distortion Field
(01:00:08) From Busboy to CEO: The Resume of an Entrepreneur
(01:02:57) Learning From Near-Death Experiences
(01:04:05) Money Means Freedom: Early Work Ethic
(01:05:25) Shoe Dog as the Benchmark: Belief Is Irresistible
(01:09:16) Documenting Time: Why Chronology Matters in Memoirs
(01:11:14) Rockefeller, Bezos, and Musk: The Master Strategists
(01:14:39) Using Doubt as Fuel: The Slow Burn of Proving People Wrong
(01:20:04) Daniel Ek and Having No Ceilings
(01:23:09) How His Father Shaped His Ambition
(01:25:52) Firing His Father From the Board: The Hardest Decision
(01:28:01) His Mother's Deathbed Wish and Lasting Regret
(01:34:47) The Ceremony of Forgiveness
(01:36:17) MDMA Therapy and Breathwork: Accessing Deeper Consciousness
(01:38:54) The Entrepreneurial Journey as a Spiritual Journey
(01:40:45) Conclusion
In this episode of How to Take Over the World, I do something a little different. Instead of breaking down one life, I share my top 10 leadership lessons drawn from every episode I released in 2025.
00:00 Introduction and Overview
02:19 Communicate Clearly at Scale
06:17 Define Your Myth
10:12 Seize Your Moment
13:28 Be Alone to Think, Collaborate to Build
16:33 Antis Inspiration
18:58 Make Extreme Decisions Quickly
24:31 Decision-Making Frameworks
28:06 Going a Little Too Far
31:20 The Power of Knowing What You Want
34:58 Being Competitively Playful
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Sponsors:
David Senra Podcast
Zashi Wallet
Speechify
The Classical Society
Premium Version
The Life of Jesus as told in the book Jesus: A Biography of a Believer by Paul Johnson.
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