Invest Like the Best with Patrick O'Shaughnessy

Niki Scevak, co-founder of Blackbird Ventures, shares his insights on identifying 'wild ideas' in venture capital. He discusses the importance of passion-driven founders and how unconventional approaches attract top talent. Scevak highlights the power of small, innovative teams, using Zoox as a prime example. The conversation also delves into redefining long-term relationships with entrepreneurs and explores the impact of AI on customer acquisition strategies. Additionally, he offers a deep dive into Canva’s revolutionary approach to graphic design.

Todd McKinnon, co-founder and CEO of Okta, shares his entrepreneurial journey from leaving Salesforce to building a leading identity management company. He discusses the emotional and practical challenges of startup life, including the painful early years of Okta. Todd elaborates on the evolution of identity management and the importance of innovation in establishing a market leader. He also provides valuable insights into navigating growth, selecting software partners, and adapting strategies in a rapidly changing tech landscape.

In this engaging conversation, Jason Karp, the visionary founder of HumanCo, and Rohan Oza, co-founder of CAVU Venture Partners and branding guru, delve into the essence of great branding. They discuss the transformative journey from hedge funds to health-focused entrepreneurship. The duo highlights the power of storytelling and authenticity in branding, along with the impact of celebrity endorsements. They also explore evolving consumer values and the importance of finding a balance between flavor and health in product offerings, emphasizing that strong brands create lasting connections.

In this insightful conversation, John Chambers, former CEO of Cisco known for scaling the company from $70 million to $40 billion, shares his business wisdom. He discusses the invaluable lessons learned from GE's Jack Welch and reveals strategies behind successful acquisitions—emphasizing pattern recognition and structured playbooks. John reflects on navigating adversities during the dot-com bust and the 2008 recession, highlighting the importance of resilience. His thoughts on customer engagement and the evolving workforce in a digital age offer valuable perspectives for leaders and investors.

Anu Hariharan, a partner at Y Combinator's Continuity Fund and former investment partner at Andreessen Horowitz, shares her expertise in growth investing. She discusses the significance of evaluating growth-stage businesses through their models rather than industries, highlighting success stories like DoorDash and Airbnb. Anu delves into the exciting opportunities within international markets, particularly in tech and e-commerce, and explores the complexities of valuation during funding rounds. Her insights on the future of the internet economy are a must-listen for any aspiring investor!

Laura Behrens Wu, co-founder and CEO of Shippo, discusses her journey from e-commerce struggles to creating a shipping solutions platform. She delves into the challenges of streamlining shipping logistics and the intersection of digital and physical worlds. Laura shares insights on customer-driven platform evolution, the impact of major players like Amazon on consumer expectations, and the importance of partnerships in enhancing service offerings. The conversation highlights the innovative strategies transforming the shipping landscape for businesses of all sizes.

Brad Gerstner, founder of Altimeter Capital, and Rich Barton, co-founder of Expedia and Zillow, share their insights on navigating modern investment landscapes. They discuss the advantages of SPACs over traditional IPOs and how technology has reshaped e-commerce. The duo reminisces about their early careers and stresses the importance of creativity in branding. They draw parallels between effective leadership and 'The Wizard of Oz,' highlighting traits like courage and wisdom. With humor and depth, they explore how human connection remains vital in business.

Jason Citron, Founder and CEO of Discord, shares his journey of transforming a gamer-centric platform into a thriving community space for all. He discusses the evolution of Discord, highlighting its role as a potential 'third place' for online connections. Citron reflects on the challenges of scaling company culture and the importance of humility in hiring. The conversation dives into user engagement strategies and the significance of small acts of kindness in building relationships, offering valuable insights for entrepreneurs in the tech landscape.

Ben Gilbert and David Rosenthal, co-hosts of the Acquired podcast, share insights from their investment journeys. They analyze legendary corporate acquisitions, spotlighting the dynamics of high-value tech deals like Instagram's. The duo discusses the intricacies of startup competition and community-building while emphasizing the critical role of mentorship in overcoming career hurdles. Tune in for a blend of historical context and practical investing lessons, making it a must-listen for aspiring investors!

Leore Avidar, co-founder and CEO of Lob, shares his entrepreneurial journey in simplifying direct mail through technology. He delves into his passion for sports card collectibles and the evolving market dynamics. Leore discusses the challenges of running dual ventures and the importance of strategic partnerships. His insights on creating and selling 'superpowers' reveal how entrepreneurs can innovate and scale effectively. The conversation inspires budding entrepreneurs to embrace risks and cultivate a mindset for aggressive growth.