
About
Conversations with the best investors and business leaders in the world. Patrick explores their ideas, methods, and stories to help you better invest your time and money.

Patrick is the Founder and CEO of Positive Sum. He founded Colossus in 2020 to build on the success of Invest Like The Best.
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Invest Like The Best
Ep.355
A Conversation with Charlie Munger & John Collison
Charlie Munger was the vice chairman of Berkshire Hathaway. In this conversation with Stripe's John Collison, recorded last year, he shares the ingredients for long-term business success, his thoughts on American society writ large, and what makes Berkshire special.
12.05.2023

Invest Like The Best
Ep.427
The Gift and The Curse of Staying Private
Bill Gurley is a former General Partner at Benchmark Capital. We cover the breakdown of incentives that created over a thousand "zombie unicorn" companies, how late-stage venture firms have largely eliminated the need to go public to access funding and liquidity, and the investing implications if AI turns out to be the single greatest platform shift of our lifetime.
06.10.2025

Invest Like The Best
Ep.414
Investing At Lone Pine
Kelly Granat is the co-CIO and Managing Director of Lone Pine Capital. We cover the building blocks behind Lone Pine's investment decisions, why the market frequently misprices the ability to execute, and the investing industry's problems with aligning incentives and duration.
03.11.2025

Invest Like The Best
Ep.195
Investing in Dignity and Character
Jacqueline Novogratz is the founder and CEO of Acumen. We cover her move from Wall Street to philanthropic capital, how creating dignity plays such a major role in her investments, and how governments and businesses can work together to solve the world’s toughest problems.
10.13.2020

Invest Like The Best
Ep.194
Upside Down Markets
The pseudonymous Jesse Livermore is one of the most respected names on financial Twitter and a research partner at OSAM. We discuss upside down markets, fiscal policy, and how the stock market can be near all-time highs in terrible economic times.
10.06.2020

Invest Like The Best
Ep.193
Better, Cheaper, Faster: Why Companies that Reduce Friction Win
The pseudonymous Modest Proposal is one of the most respected thinkers on financial Twitter. We cover the frameworks he uses to analyze today's stock market, the impacts of COVID on businesses, and break down what makes InterActiveCorp (IAC) such a unique company.
09.29.2020

Invest Like The Best
Ep.192
The Modern Activist Toolkit
Lauren Taylor Wolfe is the co-founder and Managing Partner of Impactive Capital, an activist investment management firm. We cover the entire activist toolkit, dive deep on how the modern activist playbook differs from traditional methods, and explore how she helps create value for companies.
09.22.2020

Invest Like The Best
Ep.191
Moonshots and Marketing
Rory Sutherland is the Vice Chairman of Ogilvy & Mather Group. We cover how psychological moonshots can be successful and cheap, improving a company's business by using the magic of marketing, and asking dumb questions to reach intelligent answers.
09.15.2020

Invest Like The Best
Ep.190
Lessons from Thousands of Startups
Michael Seibel is a Partner at Y Combinator and the CEO of YC’s startup accelerator. We cover what he looks for in Y Combinator applicants, frameworks to identify problems worth solving as an entrepreneur, and what it feels like to find product-market fit.
09.08.2020

Invest Like The Best
Ep.189
Great Migration Public to Private Equity
Michael Mauboussin is the Head of Consilient Research at Counterpoint Global. We cover the reasons behind the shift from public to private investing, the most significant changes in capital markets, and the rise of intangible assets.
09.01.2020

Invest Like The Best
Ep.188
Open Source Crash Course
Jeremiah Lowin is the founder of Prefect.io, an open source software company. Chetan Puttagunta is a partner at Benchmark Capital. We cover the open source software business model, building an open source community, and future opportunities in the sector.
08.25.2020

Invest Like The Best
Ep.187
The Next Wave of E-commerce
Katrina Lake is the co-founder and CEO of Stitch Fix. We cover the next wave of e-commerce, how stakeholder focus is a shareholder focus, and the future of Stitch Fix and personalized shopping.
08.18.2020

Invest Like The Best
Ep.186
The Future of Crypto
Brian Armstrong is the co-founder and CEO of Coinbase. We cover the current state of the crypto industry, how crypto can build a more open financial system and bring more economic freedom to the world, and how he has built Coinbase into a company with 1000+ employees.
08.11.2020