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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

    Mar 17 · twitter

    .@williamhockey is one of the least visible founders in tech relative to what he has created.

    He co-founded Plaid and is now building Column, a software company that owns a bank, and powers Ramp, Wise, Bilt, Mercury, and others. He funded it himself by borrowing against nearly everything he had in Plaid shares, and has never raised any outside capital.

    His story matters because so much of the value in our industry gets created through exactly this kind of extreme personal risk. He is maniacal about being the best in the world at his thing, and has spent his entire career betting on himself and doing whatever it takes to win.

    He also spends a lot of time outside the US (in places like Kinshasa) which has given him a rare perch on the power of the US dollar.

    We discuss:

    • Why emerging markets are often the most financially innovative
    • What owning 100% of his company allows him to do that VC-backed founders cannot
    • Getting margin called and nearly going bankrupt
    • Why the best founders are specialists
    • What it takes to be the best in the world at your thing
    • How Silicon Valley's consensus culture produces consensus founders
    • How the US dollar functions as an instrument of national security

    Enjoy!

    Timestamps: 0:00 Intro 9:19 Emerging Markets 14:03 Silicon Valley's Elite Consensus Problem 16:03 Rejecting the VC Hamster Wheel 21:45 Equity and Liquidity 26:03 Funding a Bank 29:45 The Necessity of Extreme Founder Risk 37:18 Finding Leverage 45:20 Longevity and Profitability in Banking 48:46 Matching Your Capital Structure to Your Business 51:44 The Unseen Power of the US Dollar 1:02:30 How AI Will Transform Legacy Banks 1:09:23 The Kindest Thing

    .@williamhockey is one of the least visible founders in tech relative to what he has created.

He co
    Mar 10 · twitter

    My conversation with Shyam Sankar (@ssankar).

    Shyam has spent nearly 20 years as the most important person at Palantir that most people have never heard of.

    We spend a lot of time understanding his worldview, which helps explain why he has devoted his life to this work. At the center of it is a belief in the primacy of people -- all meaningful change comes from a small number of builders willing to be heretics first.

    You will find few people who think as deeply about the relationship between technology and national power. In many ways, he is becoming the modern version of the heretics he most admires.

    We discuss:

    • What Alex Karp taught him about identifying superpowers and unlocking talent
    • Heretics + the components of American greatness
    • The origins of the FDE model
    • Ontology and chips – where value will accrue in AI
    • Why dual-use companies are the future of American industry
    • China and what it would take for the US to reindustrialize
    • His journey from Nigeria to Orlando and what his dad taught him about gratitude

    Enjoy!

    Timestamps: 0:00 Intro 2:23 Defining Heretics in US Military History 8:36 Shyam’s Personal Disagreeableness 9:49 Formative Experiences & Worldview 12:52 What Makes America Exceptional 14:48 What Does Greatness Mean? 15:33 Alex Karp 16:46 How to Unlock Talent 19:21 Identifying Superpowers and Kryptonite 22:54 The Gamma Ray Moment 25:00 Palantir's Next 10 Years 27:03 Forward Deployed Engineering 33:40 Explaining What Palantir Is 37:50 Military vs. Commercial Customers 39:00 The State of the US Military Today 47:01 How to Re-Industrialize America 51:06 Perspective on China as an Adversary 56:17 How to Get More Heretics in Government 1:03:53 Managing Rapid Pivots & Momentum 1:08:48 Where Will AI Value Accrue? 1:13:33 Reasserting the Legitimacy of Institutions 1:15:54 To Do or To Be? 1:16:31 Reflecting on Fatherhood 1:17:34 Kindest Thing

    My conversation with Shyam Sankar (@ssankar).

Shyam has spent nearly 20 years as the most important
    Apr 30 · Nasdaq
    3 Investing Podcasts Worth Listening To - Nasdaq
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    Let The Zombie Hunting Begin (NYSE:BEN) - Seeking Alpha
    Let The Zombie Hunting Begin (NYSE:BEN) - Seeking Alpha
    Sep 28 · prnewswire.com
    Patrick O'Shaughnessy's Venture Capital Firm Positive Sum Invests ...

    Related Questions

    What inspired Patrick O'Shaughnessy to start Positive Sum?
    How did Patrick O'Shaughnessy's background influence his approach to venture capital?
    What are some notable investments made by Positive Sum?
    How does Patrick O'Shaughnessy's podcast influence his investment strategies?
    What makes Positive Sum different from other venture capital firms?
    Patrick O'Shaughnessy, CFA
    Patrick O'Shaughnessy, CFA, photo 1
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    Location

    Stamford, Connecticut, United States