Invest Like the Best with Patrick O'Shaughnessy

Jeff Lawson, Founder and CEO of Twilio, shares insights into building successful platforms. He emphasizes the importance of APIs in modern software development and explains how non-tech businesses can transition into this space. Lawson also discusses the significance of company culture and the concept of 'drawing the owl' as a metaphor for creative problem-solving. Additionally, he highlights the crucial role of customer intimacy and collaboration in product development, advocating for a workplace where values foster connection and innovation.

Niko Canner, founder of Incandescent and former member of Bridgewater's management committee, shares insights on becoming the perfect instrument for personal and professional growth. He emphasizes aligning actions with long-term aspirations and explores how businesses can cultivate distinct cultures for success. Niko discusses the inspiring story of Aravind, which revolutionized cataract treatment in India, and highlights the importance of mentorship and effective decision-making to enhance operational effectiveness.

Brent Beshore, an entrepreneur and investor specializing in acquiring smaller businesses, revisits the podcast to share insights from analyzing over 12,000 deals. He discusses the nuances of financial deal structures and the importance of tailored strategies in business acquisitions. Brent also dives into the unique profitability of pet crematoriums and the challenges of the HVAC industry. Additionally, he explores innovative investment structures, the dynamics of property management investments, and strategies for scaling investment firms, offering a wealth of practical knowledge for aspiring investors.

Chetan Puttagunta, a general partner at Benchmark Capital, sharing insights from his impressive background in early-stage software investing. He discusses the evolution of databases with MongoDB as a case study, emphasizing agility and innovation. Key topics include empathetic product design to foster customer trust and the crucial role of recruiting exceptional talent. Chetan also highlights collaborative investment strategies and the transformative impact of AWS on cloud business models, offering a wealth of knowledge for aspiring software entrepreneurs.

Rebecca Kaden, a partner at Union Square Ventures, shares insights into thesis-driven investing and the evolution of USV’s strategy. She discusses the urgent need to reform the education system and bridge the gap between education and job preparedness. Kaden highlights innovative companies reshaping learning and challenges in capital access. The conversation also touches on digital marketing, unique tech solutions for education, and the importance of community in healthcare, all while emphasizing the vital role of consumer behavior in today’s market.

Matt Clifford, co-founder of Entrepreneur First, shares insights on talent investing and fostering entrepreneurship. He emphasizes finding ambitious individuals and forming teams with 'proto ideas.' Matt discusses deep technology's potential and the global shift in entrepreneurial hotspots, highlighting cities like Paris and Singapore. He critiques traditional early-stage investment practices and advocates for sustainable management. Finally, he explores the intersection of ambition, kindness, and innovation in the startup ecosystem.

Peter Buffett, a musician, composer, author, and philanthropist, dives deep into the essence of life beyond business and investing. He shares how moving to a nature-centric community transformed his perspective on safety, connection, and individualism. Through heartfelt anecdotes, he emphasizes the importance of celebrating those around us and fostering curiosity and authenticity. Peter advocates for community-driven initiatives and discusses the significance of vulnerability in creating meaningful relationships. This insightful conversation encourages listeners to find their own unique note in life.

In this engaging discussion, Ben Savage, a partner at Clocktower Technology Ventures, dives deep into the dynamic fintech ecosystem. He highlights how technology is reshaping investment strategies, making previously non-investable assets accessible. Ben shares insights on the evolving landscape of asset management and the impact of innovations like blockchain and cryptocurrency. He also explores opportunities for startups to disrupt financial services with low-cost solutions. Throughout, he emphasizes the need for strategic focus to thrive in this fast-changing market.

Join Jeff Ma, a data scientist and author known for his role in the MIT Blackjack team, as he dives into the fascinating world of decision-making with data. He discusses the evolution of sports analytics and its impact on gameplay strategy, contrasting qualitative and quantitative insights. Jeff shares insights from his career at Twitter and how data influences hiring practices. Plus, he explores the psychology of gambling, the importance of understanding biases, and the transformative role of analytics in both sports and business.

Vaughn Tan, a Harvard PhD and former Google employee, dives into the intricacies of quality and innovation. He shares insights on embracing uncertainty for personal and organizational growth, emphasizing how 'productive discomfort' can spark creativity. Discussing his research in restaurants, he explores how diverse viewpoints enhance innovation. Tan also critiques conventional success metrics, advocating for introspection in our career paths. Tune in for a thought-provoking perspective on fostering excellence in various fields!