Doug Leone, former leader of Sequoia Capital, shares his journey of transforming a small fund into an $85 billion powerhouse. He reflects on overcoming early hardships, the importance of simplicity in investment strategies, and balancing toughness with care in leadership. Leone discusses navigating the venture capital landscape, recognizing talent, and common pitfalls investors face. His insights emphasize adaptability in a changing market and the value of transparent communication in building trust with investors.

Doug Leone, former leader of Sequoia Capital, shares invaluable insights from over 25 years in venture capital. He emphasizes the importance of clarity in decision-making and balancing tough leadership with compassion. Leone discusses common pitfalls in investing, particularly the need to focus on business fundamentals over mere technology trends. He reflects on building competitive advantage, the significance of resilience in the face of market downturns, and the power of simplicity in investment opportunities, leaving listeners with lessons on kindness and integrity.

Doug Leone, former Sequoia Capital partner, shares wisdom from his 25+ years in venture capital. He discusses the importance of keeping investment strategies simple and transparent, offering insights on go-to-market motions and trust-building with founders. Leone reflects on his evolution from leader to mentor, emphasizing resilience and the value of genuine relationships in navigating the ever-changing investment landscape. He also highlights the critical choices between venture capital and entrepreneurship, advocating for alignment with one's strengths and passions.

Doug Leone, Global Managing Partner of Sequoia Capital, shares his journey from an immigrant in America to a leading venture capitalist. He reflects on pivotal moments, including the firm's successful investments in companies like Google and the lessons learned from missing out on Facebook. Leone emphasizes the importance of patience and ethical decision-making in venture capital, as well as the commitment to supporting entrepreneurs through financial challenges. His candid anecdotes reveal the evolution of Sequoia Capital as a respected force in the global investment landscape.

In this engaging discussion, David Vélez, the Founder and CEO of Nubank, shares his unique journey from Colombia to revolutionizing Brazil's banking system. Alongside co-founder Cristina Junqueira and Sequoia Capital's Doug Leone, they detail their battle against a banking oligopoly that imposed high fees on customers. Their story of resilience and innovation reveals how Nubank transformed the financial landscape with a strong focus on ethics and customer care, achieving over 100 million users and marking a significant milestone in fintech.

Doug Leone, Global Managing Partner at Sequoia Capital, discusses the nuances of pricing in venture capital. He emphasizes when it might be wise to pay more for certain companies while maintaining price discipline. The conversation delves into investment strategies, the balance of risk, and the critical role of market leadership. Leone highlights the importance of adapting to changing dynamics and building relationships with founders. The episode also critiques current market trends that can cloud rational investment decisions, advocating for a disciplined evaluation approach.

"Sequoia Capital is the greatest venture capital firm of all time. It's indisputable." - Jason  Jason chats with Sequoia's Doug Leone, a leader who shepherded the firm for four decades. They discuss great founders, governance, Sequoia's global expansion, mentoring the next generation of investors and more. (00:00) Jason intros today’s legendary interview w/ Doug Leone of Sequoia Capital (01:14) When Doug Leone got his start (11:00) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/TWIST (12:23) The impact selling secondary shares has on founders (15:43) “The founder’s job is to make the receptionist rich” (21:14) First Republic Bank - Discover what a long-term financial relationship can do for you. Visit https://firstrepublic.com/startup today to learn more. (22:15) Mentoring the next generation of investors (30:51) Linode - Apply to their Rise program for founder-led, early-stage startups and get 3 years of discounts at https://linode.com/twist. (31:58) Sometimes incredible companies make the founder (34:07) The greatest founders Doug has worked with (46:30) Providing companies with a running start, but not doing too much (53:10) Investing in China (57:15) Entrepreneurship in Europe (01:11:06) “Hope is not a plan. Let’s make a plan. Check out Sequoia: https://www.sequoiacap.com FOLLOW Doug Leone: https://www.linkedin.com/in/douglas-leone-a2714/ FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

Doug Leone, Global Managing Partner at Sequoia Capital, shares his 33-year journey in venture capital. He reflects on the pivotal meeting that led him to Sequoia and the evolution from COO to a more inspired leadership role. Leone discusses the importance of team culture over familial bonds in business and offers insights on navigating international expansion, particularly in China and India. He also candidly talks about the highs and lows of his early investments and how to recognize the qualities that lead to success in the venture landscape.

Frank Slootman, the former CEO of ServiceNow, and company founder Fred Luddy share their compelling journey of resilience and innovation in tech. Luddy, who started over at 50 after a bankruptcy, discusses his vision for a cloud-based IT platform that transformed into a $150B enterprise. Slootman reveals the early challenges of scaling and the fear of checking emails during high-pressure times. The two recount the risky decision-making process that nearly led to a costly misstep in selling the company, ultimately emphasizing the importance of a long-term strategy.

In this insightful discussion, Doug Leone, a partner at Sequoia Capital, explores the rapid ascent of Tiger Global in the venture capital world. He emphasizes the need for a shift in venture terminology, contemplates the enduring craft of venture alongside rising competitors, and analyzes the impact of hedge funds entering the space. Insights from other VC leaders like Bill Gurley and Michael Eisenberg highlight the challenges of increased competition and the strategic advantages of substantial capital in today's evolving market. This conversation unpacks the future landscape of investment.