Jeremy Giffon - The Billion Dollar PDF - [Invest Like the Best, EP.481]

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Investing, Technology, Business

4.7 • 2.5K Ratings

🗓️ 7 July 2026

⏱️ 77 minutes

🔗️ Recording | Apple Podcasts | RSS

🧾️ Download transcript

Summary

My guest today is Jeremy Giffon. Jeremy has been on the show before as one of our most popular guests, and this conversation is every bit as enjoyable as the first. Over the last 18 months, Jeremy has had hundreds of conversations with founders and with the capital behind their companies. I don't know many investors with such a high rep count in the most interesting corners of private markets, so I asked him what he has learned. We talk about what those lessons mean for founders and investors, why everyone has become subservient to the poster class, the hidden intellectual history behind Silicon Valley and much more. Please enjoy my conversation with my friend, Jeremy Giffon. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠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. ----- 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠. ----- WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant. Timestamps: (00:00:00) Welcome to Invest Like The Best (00:02:02) Jeremy Giffon (00:02:34) Lessons from 18 Months of Founder Conversations (00:07:01) The Billion-Dollar PDF (00:08:13) The Unifeed & Rise of the Timeline (00:17:02) Power Law & Breakout Content (00:18:48) AI Algorithms Driving Content (00:20:38) Timeline-Native White House (00:21:09) Traits of Great Posters (00:25:27) Peak Guy & the Billionaire Priest Class (00:32:13) Billionaires Now Defer to Posters (00:34:52) Freedom vs. Relevance (00:38:53) AI & White-Collar Job Displacement (00:40:53) Stewarding Your Gifts as Moral Duty (00:43:18) Next Wave of Finance: Equity-First Firms (00:53:26) East Coast vs. West Coast Finance (00:55:34) Beating the Market Is Not That Hard (01:00:40) SPV Feudalism & Allocation (01:02:10) Egregious SPV Fee Structures (01:04:50) Simplicity vs. Complexity in Investing (01:07:15) Hiring: Attracting Differentiated Talent (01:11:00) Silicon Valley's Hidden Intellectual Traditions

Transcript

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0:00.0	Ramp is the only platform built to make your finance team leaner, faster, and better,
0:04.0	saving businesses 5% annually on average so you can stay focused on growth.
0:08.7	Ramp customers grew revenue 3.2 times faster than the average American business.
0:12.9	Visa, Versel, Cursor, Stripe, Notion, 11 Lab, Shopify, and 70,000 other businesses all run on Ramp.
0:19.3	Mind us too, and so should yours.
0:21.0	Learn more at ramp.com slash invest.
0:24.2	Felix by Rogo is a personal finance agent that turns a single prompt into finished
0:28.5	client-ready work using your firm's own templates, context, and standards.
0:32.4	Send Felix an email like, take these comments and turn them for me, or update my tracker
0:36.5	with the context of these
0:37.5	emails, or run the ability to pay math on this buyer, and Felix sends back finished PowerPoint
0:42.5	decks, Excel models, and sourced research. Felix works the way your team already does,
0:47.6	delivering work quickly and accurately around the clock. Learn more at rogo.a.ai slash Felix.
0:53.5	Open AI, cursor, anthropic, perplexity, and Versel all have something in common.
0:57.6	They all use WorkOS.
0:59.4	And here's why.
1:00.2	To achieve enterprise adoption at scale, you have to deliver on core capabilities like
1:04.3	SSO, Skim, Rback, and Audit logs.
1:07.5	That's where WorkOS comes in.
1:09.0	Instead of spending months building these mission-critical capabilities yourself, you can just use WorkOS APIs to gain all of them on day zero.
1:16.2	That's why so many of the top AI teams you hear about already run on WorkOS. WorkOS is the fastest
1:21.6	way to become enterprise ready and stay focused on what matters most, your product. Visit WorkOS.com
	...

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