Invest Like The Best

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 O'Shaughnessy Host Patrick O'Shaughnessy

Patrick is the Founder and CEO of Positive Sum. He founded Colossus in 2020 to build on the success of Invest Like the Best.

Investors

Leaders

Invest Like The Best

Ep.196

Lessons on Early Stage Investing and Getting Acquired

Ben Gilbert and David Rosenthal are investors and the duo behind the Acquired podcast. We cover some of the greatest corporate acquisitions of all time, discuss what makes acquisitions successful, and talk over the investing lessons Ben and David have learned across their careers.

10.20.2020

Play

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

Play

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

Play

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

Play

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

Play

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

Play

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

Play

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

Play

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

Play

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

Play

Contact

Get in touch at help@joincolossus.com