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Patrick O'Shaughnessy, CFA
Founder of Positive Sum & Colossus
Patrick O'Shaughnessy, CFA is a prominent figure in the investment and venture capital world. Here are some key details about him:
Professional Background
Patrick O'Shaughnessy is the Founder and CEO of Positive Sum, an early-stage venture capital firm.23 He co-founded the firm with Sam Cates, and they invest across stages, particularly from Seed to Series B, in companies that are creating and reinventing categories.2
Investment Philosophy
O'Shaughnessy and Positive Sum focus on:
- Seeking win-win opportunities where all parties have a vested interest from the start4
- Taking calculated risks to create original and inspiring outcomes4
- Providing resources and tools to help creators stay focused on their goals4
- Embracing diversity in all its forms to foster true innovation4
Media Presence
Patrick is well-known for hosting the popular podcast "Invest Like the Best".1 This podcast features conversations with top investors and business leaders, exploring their ideas, methods, and stories to help listeners better invest their time and money.1
Other Ventures
In addition to Positive Sum, O'Shaughnessy is involved in several other initiatives:
- O'Shaughnessy Ventures (OSV): This entity provides grants and support for ambitious creators across various domains4
- Infinite Loops: A podcast and media platform for exploring transformative ideas4
- O'Shaughnessy Fellowships: A program offering $100,000 grants to creators looking to build something great4
Investment in Tegus
In September 2022, Positive Sum invested $20 million in Tegus, a leading research platform for institutional investors.2 As part of this deal, O'Shaughnessy joined the Tegus Board as an Observer.2
Patrick O'Shaughnessy's approach combines quantitative analysis with creative thinking, making him a unique and influential figure in the investment world.
Highlights
“Narrative is fear made conscious and conquered through action.”
“Things don’t happen to you. You act against obstacles. With knowledge comes power to affect the outcome.”
What makes @elonmusk iconic is his refusal to seek acceptance while pursuing something bigger.
"He's so unconcerned with the traditional hero trajectory — breaking societal rules to reach some platonic ideal that's worth more than acceptance."
He’s willing to upset people if it means pursuing a deeper truth he believes matters more than being liked.
"To live and espouse a worldview that is universally disliked. That's iconic."

