#83: Chip Conley, Founder at Modern Elder Academy — Using regret as fuel; how and why founders need to shift their identities; how to manage people older than you; and his favorite interview question (Repost)

#82, Gary Vaynerchuk, Serial Entrepreneur and Chairman of VaynerX — The importance of kind candor, how to get over your insecurity, and why you need to embrace social media (Repost)

#81: Colin Bryar, Co-Author of "Working Backwards;" former Chief of Staff to Jeff Bezos — How Amazon built its processes, the birth of the 6-page memo, and how to instill psychological safety in a competitive culture

#80: David Heinemeier Hansson, Co-Owner of 37signals— Creating with first principles, acting with courage, and working in a world with no managers

#79, Shegun Otulana, Founder and CEO of Harmony Venture Labs—From Nigeria to unicorn founder; bootstrapping a profitable business; learning to embrace feedback

#78: Jake Schwartz, Co-Founder and former CEO of General Assembly—Navigating startup chaos, what a startup and the Beatles have in common, and the wisdom of looking back on the journey

#77: Jake Kloberdanz, One Hope Winery Co-founder — Building “Girl Scout Cookies” for adults, building community, and scaling philanthropy

#76: Susan McPherson, Founder and CEO of McPherson Strategies — Investing in dormant ties, networking superpowers, and converting nerves into strength

#75: Jeff Shiner, CEO of 1Password — Earning the right to lead, how to thrive while bootstrapping your company, and how to hire senior executives

#74: Seth Godin, Author and Marketing Strategist — showing up for yourself, creating conditions for your best work, and how to deal with massive rejection (Repost)

#73: David Savage, Group Technology Evangelist at Nash Squared and host of TechTalks podcast — How to become an "intrapreneur," the importance of consistent behavior over vanity metrics, and how to learn to trust yourself

#72: Kim Scott, Author of Radical Respect and Radical Candor — Building your team’s muscles to address discomfort, cutting through workplace politics, and why you need a purple flag

#71: Matt Reustle, CEO of Colossus — Lessons from a first-time CEO, how to analyze a career pivot, and the art of a great question

#70: Mike Michalowicz, Author and Entrepreneur — The right way to hire; practical exercises for team retention; and how to come back from rock bottom

#69, Rahul Vohra, Co-Founder and CEO of Superhuman — How to craft core values, tactics for implementing culture to help you achieve company goals, and the importance of moving quickly

#68, Gina Bianchini, Co-Founder and CEO of Mighty Networks — The secret to building communities, managing self-worth as a CEO, and why humor is a leadership superpower

#67, Gary Vaynerchuk, Serial Entrepreneur and Chairman of VaynerX — The importance of kind candor, how to get over your insecurity, and why you need to embrace social media

#66, Mary-Catherine Lader, COO of Uniswap Labs — How you know you're ready to take on more risk, why you should create anti-values, and the importance of community

#65, Gregory Galant, Co-Founder and CEO of Muck Rack — Pros and cons of bootstrapping, building a scrappy culture, the importance of building a network

#64, Kristi Herold, Founder and CEO of JAM — Pivoting during a crisis, leading through playfulness, and creating joy in the workplace