Patrick O’Shaughnessy

On September 12, 2016, the investing interview podcast Invest Like the Best, hosted by O’Shaughnessy, released its first episode, featuring hedge fund manager and author Jeff Gramm on the history and current state of shareholder activism and on Gramm’s approach of taking large positions and often board seats in undervalued companies. Early episode pages were hosted on InvestorFieldGuide.com.⁠[1][1][1]

In March 2017, he interviewed his father, Jim O’Shaughnessy, on the show, introducing him as one of the pioneers of quantitative equity research; both have written extensively on factor investing.⁠[2][2]

O’Shaughnessy was then working at O’Shaughnessy Asset Management. In September 2019, he noted in show notes that the firm did not buy IPOs; in January 2020, he said the firm had built an investing platform called Canvas and described Benchmark general partner Chetan Puttagunta as his key guide to understanding the world of enterprise software, whose advice had been critical to Canvas’s early success.⁠[3][4][4][4]

On September 22, 2020, O’Shaughnessy announced on the show that, after years of building, operating, and investing in software, he was launching Positive Sum, a new early-stage equity investing firm. In December 2021, he said he had invested through Positive Sum in the new company of Doug Colkitt, who had worked first in Citadel’s high-frequency trading group, then traded for himself, and then turned to building the decentralized exchange CrocSwap.⁠[5][5][6][6]

On December 21, 2021, in the show notes for his interview with Franklin Templeton President and CEO Jenny Johnson, O’Shaughnessy wrote that he had met Johnson as the two firms explored a partnership, and that three months earlier they had announced that Franklin Templeton would acquire O’Shaughnessy Asset Management. By this time, Invest Like the Best was a property of Colossus, LLC.⁠[7][7][7]

In the fall of 2022, Positive Sum invested $20 million in the investment research platform Tegus to support the expansion of its products; O’Shaughnessy described himself as a longtime user and advocate of Tegus. Tegus was later acquired by AlphaSense.⁠[8][8][8][9]

On August 6, 2024, episode 383 of Invest Like the Best featured Conviction founder Sarah GuoSarah GuoSarah Guo is a venture capitalist, founder and managing partner of Conviction, an early-stage investment firm focused on artificial intelligence, and previously a partner at Greylock.Open the full entry, discussing the challenges and rewards of leaving Greylock to start her own firm and her views on the frontier of artificial intelligence.⁠[10][10][10]

On April 30, 2025, the financial AI company RogoRogoRogo is an artificial intelligence platform company serving financial institutions such as investment banks, private equity firms, and hedge funds, co-founded by Gabe Stengel, who serves as its CEO; it uses models and agents tailored for finance to handle work such as research, modeling, and deal documents, raised funding from its seed round through its Series D between 2024 and 2026, and has received strategic investment from several global banks.Open the full entry announced a $50 million Series B led by Thrive Capital, with new investors including O’Shaughnessy’s Positive Sum Ventures; Positive Sum participated again in the $160 million Series D that Rogo announced on April 29, 2026.⁠[11][12]

On January 20, 2026, Invest Like the Best republished an interview of O’Shaughnessy by David Senra, host of the Founders podcast. He said he does not plan to be interviewed often; the conversation barely touched on investing or interviewing techniques, instead covering finding an organizing principle for life, undiscovered talent, and the idea that “the reward for good work is more work,” as well as the principles behind how he builds Invest Like the Best, Colossus, and Positive Sum, including the origin of Invest Like the Best and why he started the Colossus magazine in 2025.⁠[13][13][13][13][13][14]

On September 1, 2026, episode 489 of Invest Like the Best interviewed Sarah Guo again, discussing the AI frontier, compute independence, robotics, and her experience raising a fund; Colossus managing editor Dom Cooke also wrote a profile of her, “Sarah’s Wager.” On September 22, episode 492 featured Gabe StengelGabe StengelGabe Stengel is an entrepreneur and the co-founder and CEO of the financial AI platform Rogo.Open the full entry, co-founder and CEO of the financial AI company Rogo, discussing how Rogo evolved alongside frontier models, outcome-based pricing, and how AI will change the way capital is raised, assets are priced, and deals get done; Rogo was one of the episode’s sponsors.⁠[15][15][15][15][15][16][16][16][16][16][16][17]

Colossus covers the frontier of business, investing, and technology, publishing a digital magazine and a quarterly print magazine, and its podcast network includes Invest Like the Best, Founders, and Business Breakdowns; its name is inspired by Tim Urban’s 2017 post “The Human Colossus.”⁠[18][18][18]

Positive Sum’s mission is to back founders pursuing their life’s work; as of October 2026, its portfolio highlights include Etched, Cognition, Base Power, Imprint, Modal, Rogo, Neko Health, Physical Intelligence, Vanta, Bending Spoons, Ridgeline, Eight Sleep, and ID.me, among others.⁠[9][9][9][9]

Positive Sum: Official website: https://www.positivesum.com/ (opens in a new window).⁠[14]

Colossus: Official website: https://colossus.com/ (opens in a new window).⁠[18]

X: Public account: https://x.com/patrick_oshag (opens in a new window)⁠[9]