Jessica McKellar | Pilot - On building billion-dollar companies, why founders should never stop selling, and the power of being an outsider

Aaron Epstein | Y Combinator – On what makes great founders, the lessons of failure and focus, and building opportunity for others

Vanessa Larco | Premise VC - On leaving NEA to build her own firm, spotting outlier founders, and the next wave of consumer tech

Alda Leu Dennis | Hawktail VC — On building a new kind of venture firm, lessons from Thiel and Tan, and why boldness attracts the right allies

Stan McChrystal | McChrystal Group - On character, the choices that define a life, and the great lessons along the way

Samara Hernandez | Chingona Ventures - On breaking barriers, using the unknown as a catalyst, and never taking no for an answer

Nitish Maini | WorldQuant - On democratizing opportunity, why big risks aren’t as risky as you think, and the two-year rule for growth

Brad Feld | Foundry - On what real leadership looks like, how to show up through crisis, and the joy of long arc characters

Finn Meeks | South Park Commons - On going from -1 to 0, finding world class community, and redefining your identity

Chris Olsen | Drive Capital - On building a $2B firm outside of Silicon Valley, always accepting responsibility, and giving founders more than just money

Dan O'Connell | Front - On driving a ~$100m ARR startup, the evolution of pricing, and how some people never change

Mike Miller | Liquid 2 Ventures - On going from nuclear physicist to the early Y Combinator days, selling a startup to IBM, and launching a different type of VC fund

John Mannes | Basis Set - On going from government and to venture, how curiosity breeds alpha, and sometimes we just need to focus on what's right in front of us

Mario Schlosser | Oscar Health - On how AI will make healthcare better, his journey from upstart to IPO, and why you need to do things 100%

Greg Lippmann | LibreMax Capital - On the 'Big Short,' finding mentors through hard work, and understanding the value in setbacks

Songyee Yoon | Principal Venture Partners - On why gaming is the frontier of tech, why tomorrow's biggest companies are starting today, and why it pays to have a thick skin

Barry Ritholtz | Bloomberg & Ritholtz Wealth Management - On 'How Not To Invest,' being both a specialist and generalist, and turning his ADHD into a superpower

Ron Biscardi | iConnections - On convening over $50 trillion in AUM, building culture and conviction in a remote world, and how action beats analysis

Stacey Gerber | Sequoia Capital - On creating community with intention, understanding the value of preparation, and how helping others is the key to helping yourself

Jon Bradford | Dynamo Ventures - The 'Godfather of European Accelerators' on advice for founders, scaling teams, and the future of American manufacturing