Invest Like the Best with Patrick O'Shaughnessy Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS]
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Jun 27, 2025 
Charlie Songhurst, former head of strategy at Microsoft and prolific angel investor, shares invaluable investing insights from his experience with nearly 500 companies. He discusses the contrasting investment philosophies of the East and West coasts, emphasizing the importance of balancing quant and qual strategies. The conversation delves into navigating remote work while exploring cryptocurrencies like Bitcoin and Ethereum. Additionally, Songhurst highlights the complexities of investing, the influence of strong mentorship, and how hiring dynamics shape startup success.
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Key Startup Success Filters
- Startups fail at every stage due to distinct filters: team productivity, product-market fit, scaling management, and institution building.
- Managing declining labor productivity as teams grow is a crucial determinant between success and failure.
Managing Productivity Decline
- Declining productivity per person in scaling startups can be massive, sometimes destroying overall output.
- Great startups manage the organizational politics better, dampening internal conflicts to maintain high productivity.
Early Hiring Determines Culture
- Invest deeply in recruiting exceptional, synergistic people early as they multiply overall productivity.
- Avoid panicking to hire quickly, as early hires shape company culture and future recruiting success.
