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#408 How to Make a Few MORE Billion Dollars: Brad Jacobs
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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27 Jul 2026TRANSCRIPT
Mental Models That Change How You Think | Bill Gurley
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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Check out Runnin’ Down a Dream: How to Thrive in a Career You Actually Love
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12 Jul 2026
Don’t Follow Your Passion | Ben Horowitz’s Advice for New Graduates
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.
Inside a recent episode
Mental Models That Change How You Think | Bill Gurley
Published 27 Jul 2026 · Transcript excerpt
[…] I wonder about the role of retail investors in this. If you tokenize some of these assets, they might be competing with VCs in some way to fund some of these startups. How do you think about all of that playing out? Well, first of all, there is zero lack of fund availability right now. That's not the bottleneck. But the pricing would change, right? There's no constraint. I mean, this is kind of played out in the public markets. I mean, I think you look at obviously like stocks like GameStop, but I think most people believe Palantir is a stock that retail investors really love and take it to a valuation that it's very hard for institutional investors to get their head around. […]
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