Patrick O'Shaughnessy

Founder of Colossus and Positive Sum, venture capitalist, and host of the 'Invest Like the Best' podcast.

Claims

As speaker

Mentioned in

Key positions and views

Media as a Core Business Driver: Believes that high-quality content, such as podcasts and long-form profiles, is a central pillar of his business that drives network and opportunity, predicting his written content arm will become larger than his podcast.

Synthesizing Expertise is Key: Actively seeks out and applies specific ideas from proven leaders in different fields, such as Daniel Ek for building software and Chathan Pudagunta for selling it.

Bet on Proven Talent: Advocates for hiring established, great leaders rather than betting on potential, echoing Charlie Munger's advice, and applies this lens to identifying future great investors.

Long-Term Holding Philosophy: Has articulated an investment strategy focused on buying and holding businesses for the long term, which he has termed 'permanent equity.'

AI as a Democratizing Force for Building: Views emerging AI tools like Claude and ChatGPT as transformative technologies that significantly increase the ability of both technical and non-technical people to build software.

Podcast consensus on O'Shaughnessy

Points of consensus

▶O'Shaughnessy's media ventures are highly influential and a core part of his business strategy. His podcast 'Invest Like the Best' provided the initial investment education for Spotify's Daniel Ek, and his company Colossus was able to attract talent like David Senra based on its reputation.Apr 2026

▶He demonstrates a pattern of rapid and decisive execution in his business ventures. He notably launched his first venture fund in the summer of 2020 within a single month of being approached by Sam Hinkey.Apr 2026

▶He is aggressively expanding his media company, Colossus, into long-form written content. This is evidenced by the launch of a magazine-style profile division and the hiring of a top editor, Jeremy Stern, with the explicit goal of making it a larger business than his successful podcasting arm.Apr 2026

▶He consistently learns from and applies the ideas of other successful individuals. He credits Daniel Ek and Chathan Pudagunta for software business ideas, Brett Victor for design principles, and Charlie Munger for hiring advice.Apr 2026

Points of debate

▶O'Shaughnessy's commentary presents a contrast between achieving impact through broad scale versus deep focus. He discusses Bill Campbell's model of coaching a small number of key executives to achieve massive impact, which contrasts with the mass-market scale sought by many tech companies he analyzes.Apr 2026

▶There is a nuanced tension in his hiring philosophy. He cites Charlie Munger's advice to hire already-great CEOs rather than for potential, a conservative approach that contrasts with the typical venture capital model of betting on promising but unproven founders.Apr 2026

▶His investment philosophy appears to span different time horizons and structures. He has termed a long-term buy-and-hold strategy 'permanent equity,' while also launching a venture fund, which typically operates on cycles of investment and eventual exits.Apr 2026

▶His approach to business building seems to prioritize the synthesis of existing ideas over pure invention. He explicitly credits others for the core concepts of building and selling software in a previous business, suggesting a focus on best-in-class application rather than origination.Apr 2026

Key themes

▶Media as a Venture FlywheelApr 2026

O'Shaughnessy strategically uses media, including his influential podcast and new long-form profile division at Colossus, to build his network, source opportunities, and attract talent. His podcast educated Daniel Ek on investing, and his company's reputation attracted David Senra, demonstrating how content directly fuels his venture and business activities.

This integrated media-venture model creates a powerful competitive advantage, where his content platform generates proprietary deal flow and insights, while his investment activities provide content, creating a self-reinforcing loop.

▶The Synthesizer's EdgeApr 2026

A core pattern in O'Shaughnessy's approach is the identification, synthesis, and application of ideas from a diverse set of experts. He explicitly credits Daniel Ek for software building ideas, Chathan Pudagunta for sales strategies, and Brett Victor for design principles, applying these external concepts to his own ventures.

His primary value-add may not be pure invention but rather his skill as a 'curator' and 'integrator' of best-in-class ideas, making him an effective operator who can rapidly adopt proven models.

▶Identifying and Backing Elite TalentApr 2026

O'Shaughnessy shows a distinct focus on identifying and elevating top-tier individuals, whether as investment subjects, business leaders, or employees. He predicts Jesse Beirutti will be an all-time great investor, hired editor Jeremy Stern based on the quality of a single article, and studies the habits of exceptional figures like Karim Atiyeh.

This suggests his investment and operational thesis is heavily weighted towards the 'jockey over the horse,' believing that backing exceptional individuals is the highest-leverage activity.

▶Bias for Rapid ExecutionApr 2026

The claims portray O'Shaughnessy as an operator who moves with speed and conviction. He launched his first venture fund within a month of a key conversation and is building a new media arm at Colossus with the bold expectation that it will quickly eclipse his established podcast business.

Investors and partners should expect him to capitalize on opportunities quickly, indicating a high tolerance for calculated risk and a preference for action over prolonged deliberation.

Source episodes

Sentiment over time

Not enough data for timeline

Changes over time

Pre-2018

O'Shaughnessy's podcast, 'Invest Like the Best,' gains significant influence, serving as the initial investment education for prominent figures like Spotify founder Daniel Ek.

Summer 2020

He enters the venture capital space with speed, launching his first venture fund within a month of a pivotal conversation with investor Sam Hinkey.

Post-2020

His company, Colossus, expands its media footprint and influence, successfully recruiting 'Founders' podcast host David Senra, who turned down a competing offer to join.

Recent

O'Shaughnessy launches a new media arm at Colossus focused on long-form, magazine-style profiles of founders and investors, hiring Jeremy Stern to lead it and predicting it will become the largest part of the business.

Recent

His public commentary focuses on analyzing hyper-growth companies like Ramp and discussing the transformative impact of new AI technologies like ChatGPT and Claude on software development.

Suggested prompts

How does O'Shaughnessy's media strategy at Colossus directly influence the deal flow and due diligence process for his venture fund? &nearr;To what extent does O'Shaughnessy's reliance on the wisdom of established figures like Munger and Ek shape his own investment theses, and where does his original thinking diverge? &nearr;Analyze the potential conflicts of interest and synergies that arise from operating a venture fund alongside a media company that profiles founders and investors. &nearr;Based on his commentary on Ramp and AI tools, what are the key attributes O'Shaughnessy looks for in a hyper-growth technology company today? &nearr;

Key concepts

Venture Capital Strategy 5 ep Media & Content Business 4 ep Leadership & Hiring 3 ep Software Business Models 3 ep Company Analysis (Ramp) 3 ep Learning from Experts 3 ep Artificial Intelligence 2 ep Investment Philosophy 2 ep

Notable quotes

“will go down I would predict as one of the great investors ever”

Patrick O'Shaughnessy · My Conversation With Patrick O'Shaughnessy, Founder of Colossus & Positive Sum | David Senra

“I suspect it won't be long until that's much bigger than even the podcast, which itself is very, very big.”

Patrick O'Shaughnessy · My Conversation With Patrick O'Shaughnessy, Founder of Colossus & Positive Sum | David Senra

“Patrick O'Shaughnessy launched his first venture fund in the summer of 2020 within one month of being approached by Sam Hinkey to invest in Hinkey's own fund.”

Patrick O'Shaughnessy · My Conversation With Patrick O'Shaughnessy, Founder of Colossus & Positive Sum | David Senra

“Ramp is one of the fastest companies to grow to over $1 billion in revenue, achieving this milestone in five to six years.”

Patrick O'Shaughnessy · The Anatomy of Ramp's Hyper-Growth | Karim Atiyeh Interview

Report last updated: Apr 21, 2026

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