The Dart Board with Daniel Dart

Meet Mario Schlosser, co-founder and CTO of the publicly traded health insurance company, Oscar Health (OSCR:NYSE). In this conversation, Mario shares the personal story that led to the founding of Oscar Health, discussing the challenges and triumphs of navigating the healthcare industry, and the imminent impact of technology and AI on all aspects of health and treatment. From his transition from gaming to healthcare, his experiences in leadership, and the importance of prioritizing mental health, we cover the best and worst advice he's ever received and how sometimes what we think are pivotal moments are just part of growing up.

Meet Greg Lippmann. In this episode, we dig into his journey from public schools, working at summer camps, to his first day on a trading floor, and when he knew the 'Big Short' was actually going to break his way. From a challenging start in finance to becoming a prominent figure in the industry, to launching his firm LibreMax, which now manages north of $12 billion. He discusses his time as an emerging manager, the strategy of getting started, the lessons learned from the financial crisis, and why working hard is beneficial for more than just career growth.

Meet Songyee Yoon, one of the most inspiring tech leaders and investors around today. In this conversation, she shares her remarkable journey from growing up in Korea to getting her PhD in computational neuroscience at MIT to becoming the President and Chief Strategy Officer at NCSoft, one of the world's biggest gaming companies. She discusses her transition from academia to industry, the evolution of gaming technology, and why understanding it is essential to understanding the future. And why she made the jump to launch a new venture capital firm, Principal Venture Partners, which focuses on investing in AI native companies. Throughout the discussion, she shares valuable lessons about overcoming adversity, why it pays to have a thick skin, and why there is no single type of perfect founder.

Meet Barry Ritholtz, the founder, chairman, and CIO of Ritholtz Wealth Management, as well as a long-time contributor at Bloomberg Media. In this episode, he shares his journey from a trading desk to establishing a successful wealth management firm. He discusses his new book, 'How Not to Invest,' which explores the pitfalls of investing and the importance of understanding behavioral finance. Barry emphasizes the balance between being a specialist and a generalist, the challenges of starting a business, and how writing helps him clarify his thoughts. He also reflects on his personal journey with ADHD and how it has shaped his approach to work and life.

Meet Ron Biscardi, founder and CEO of iConnections - a platform that connects and convenes asset owners and managers that collectively control over $50 trillion in AUM.In this episode, we discuss Ron's journey from engineering to entrepreneurship and the lessons it taught him about taking action, as well as the evolution of iConnections as a capital introduction platform that was initially built as a solution to a problem he faced himself.We dig into the challenges and successes of building a remote team, as well as insights on hiring strategies, company culture, and why people should avoid overanalyzing and just get into it.Ron also shares how he learned through loss how every day is a blessing, and how we can all turn profit into purpose.

Meet Stacey Gerber, partner at Sequoia Capital, where she leads operations and experiences. In the episode, we delve into the distinctive role of operations in venture capital, the significance of community, and the value of being prepared for both the big and little things.Stacey shares insights on creating meaningful connections, the concept of a 'through line' for all experiences, and how in-person gatherings are the key to building genuine community.She closes with powerful lessons on growing through tough times and offers valuable advice on giving and why it's the most powerful way to win.

Meet Jon Bradford, Managing Partner of Dynamo Ventures, a leading supply chain-focused seed stage venture capital fund based in Chattanooga, Tennessee.In this conversation, we discuss his journey from accountant to “The Godfather of European Accelerators”, how access to information makes now a great time to be a founder, and why the best salespeople come from Utah.We also discuss scaling teams, how Dynamo Ventures thinks about its tech stack, and what the rebirth of American manufacturing might look like in the age of AI.

Chris Farmer, the founder and CEO of SignalFire, discusses his journey in venture capital and how his firm has grown to manage around $3 billion in assets. He shares insights on leveraging AI to sift through 80 million opportunities, the importance of vision for budding VCs, and strategies for building ‘structural advantages’. Farmer emphasizes the need for differentiation in a crowded market and highlights the critical role of mentorship and developing lasting relationships for long-term success.

Henry Ward, CEO and co-founder of Carta, shares his inspiring journey from a failed startup to leading a thriving unicorn that supports over 40,000 companies. He discusses the challenges of scaling a business in a non-hype sector and the evolution of Carta from simple cap tables to comprehensive financial services. Henry emphasizes the importance of effective team management, the emotional complexities of leadership, and the balance between customer focus and mental health. His insights on resilience and empathy in personal growth make for a thought-provoking listen.

Meet Nolan Bean, chief investment officer at FEG Investment Advisors, an investment advisory firm managing and advising on more than $90 billion in assets on behalf of foundations, endowments, healthcare, systems, and other institutional investors.In this conversation, we discuss his 20-year journey from associate to CIO at FEG, how baseball informs his investment process, and tactical advice for emerging managers seeking their first institutional LP.We also discuss his philosophy on firm culture, the importance of ‘anti-fragile’ portfolio construction, building lasting professional relationships, and why the client isn’t always right.