Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.colossus.com
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Jeff Horing, co-founder of Insight Partners, about building a successful technology investment firm. Jeff discusses Insight's sourcing strategy, involving a large team systematically contacting companies, and their contrarian one-fund strategy, w...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Sam Hinkie, former NBA executive and now venture capitalist at 87 Capital, about his approach to interviewing, evaluating talent, and building trust. Hinkie emphasizes understanding how people think and learn, using digital "breadcrumbs" to asses...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Sean Feeney, co-founder of Grove House Hospitality Group and owner of Lilia and Missy, two popular New York City restaurants. Feeney recounts his transition from a successful finance career to the restaurant industry, inspired by his neighbor, Mi...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Justin Ishbia, founder of Shore Capital, a private equity firm specializing in microcap businesses. Ishbia discusses Shore Capital's investment strategy, emphasizing a system-driven approach over individual stars, focusing on inefficient microcap...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Joe Liemantt, principal at Alpha School and founder of Trilogy Software and ESW Capital, about Alpha School's innovative approach to education. Liemantt explains how Alpha School uses AI to personalize learning, enabling students to master academ...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Mark Bertolini, former CEO of Aetna and current CEO of Oscar Health. Bertolini shares his leadership story, marked by a severe skiing accident and his son's cancer battle, which reshaped his perspective on healthcare. The conversation covers his ...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Peter Lacaillade, the Chief Investment Officer for Private Investments at SCS Financial, about private equity and wealth management. Peter discusses SCS's pooled vehicle structure, which allows them to compete with institutional giants for top-ti...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Andrew Milgram, founder of MarbleGate Asset Management, about his approach to distressed investing in the middle market and his concept of the K-shaped economy, where larger, well-capitalized companies thrive while middle-market businesses strugg...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Ramtin Naimi, founder of Abstract Ventures, about his unconventional journey in venture capital, drawing parallels between the art world and investing. Ramtin discusses his early experiences, including running a hedge fund and facing bankruptcy, ...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Brad Jacobs, a serial entrepreneur who has founded seven billion-dollar or multi-billion-dollar businesses. Jacobs discusses his investment strategies, focusing on scalability, M&A, and industry consolidation. He emphasizes the importance of inte...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Zach Dell, CEO of Base, about the intricacies of the electrical grid and the future of energy. Zach explains the grid's physical and financial infrastructure, its historical context, and the regulatory environment, particularly highlighting Texas...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Alan Waxman, co-founder and CEO of Sixth Street, an investment firm known for its flexible, multi-strategy approach. Waxman discusses his early days at Goldman Sachs, the importance of unitizing risk and return, and Sixth Street's investment phil...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Caryn Seidman-Becker, the chairman and CEO of CLEAR, about her journey of acquiring the company out of bankruptcy and transforming it into a leading identity platform. Caryn discusses CLEAR's vision as a secure identity platform beyond travel, em...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Jens Grede, co-founder and CEO of SKIMS, about the intersection of pop culture and commerce. Grede discusses the importance of understanding cultural trends, the shift from institutions to individual voices, and how SKIMS broke through a fragment...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Charlie Songhurst, former head of strategy at Microsoft and prolific angel investor, about his experiences and insights on business, investing, and people. Songhurst shares his framework for evaluating founders and startups, emphasizing the impor...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Alex Pall and Drew Taggart, known as The Chainsmokers, about their evolution from musicians to venture capitalists. They discuss their investment philosophy through their fund, Mantis, which mirrors their high-touch, relationship-driven approach ...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Jay Hoag, co-founder of Technology Crossover Ventures (TCV), about the current state of technology investing. Hoag discusses the increasing importance of macro factors like regulation, opportunities in consumer internet businesses, and the differ...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Dinakar Singh, the founder of TPG Axon, about his journey in investing and his personal mission to find a cure for his daughter's spinal muscular atrophy (SMA). Dinakar shares the emotional story of his daughter's diagnosis, his decision to leave...
In this episode of Invest Like the Best, Patrick O'Shaughnessy interviews Bill Gurley about the current state of venture capital. Gurley outlines key market realities, including the rise of mega VC funds, the prevalence of zombie unicorns, stalled IPO and M&A markets, LP liquidity issues, and the impact of the AI wave....
This is a special episode of the "Invest Like the Best" podcast featuring the "50X" series, hosted by Will Thorndike, focusing on investments that have appreciated at least 50-fold, with Season 2 featuring Asurion. The episode includes an interview with Will reflecting on his experience with Asurion, an early investmen...
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