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My guest today, Bob Pittman, has had one of the most interesting careers I’ve ever come across. Today, he’s the CEO of iHeartMedia, the country’s largest operator of radio stations and podcasts. Bob also created MTV, was the CEO of Six Flags and 21 Century Real Estate, and the COO of AOL and AOL Time Warner. He’s the Dos Equis man of business. In our conversation we discuss why convenience is king for consumers, his lessons from building MTV into one of the most iconic brands and media properties in the world, the rise of user-generated content platforms, and the future of media. We also ..read more

My guest today is Sam Hinkie. Sam worked for more than a decade in the NBA with the Houston Rockets and then as the President and GM of the Philadelphia 76ers. And now, after years of personal investing, he has launched his own venture capital firm, Eighty-Seven Capital. Every conversation I have with Sam is alive with insight, and this one is no different. We explore the idea of studying the “breadcrumbs” that someone leaves behind as a way to track their progress and trajectory, finding and attracting the right people into one’s orbit, and the lessons from the NBA that most shape his invest ..read more

My guest today is Michelle Zatlyn. Michelle is the co-founder and COO of Cloudflare, a now $25 billion dollar business which she helped take public last year. Cloudflare helps businesses make their websites faster and more secure, and over 25 million websites are running Cloudflare today. In our conversation, we discuss the catalyst for starting CloudFlare, explore the layers of the internet and the future of distributed storage and computing power, and discuss how and why Cloudflare operates its network across 200 cities globally. We close with the importance of finding and working ..read more

My guest today is Danny Meyer, the founder and CEO of Union Square Hospitality Group, which compromises some of the most acclaimed restaurants in New York like Gramercy Tavern and Union Square Café. He’s also the founder and chairman of Shake Shack, which began in New York City but is now a publicly traded company with hundreds of locations worldwide. Our conversation focuses on how great hospitality leads to a great business, regardless of what sector its in. We discuss why hospitality is the starting point for Danny’s business philosophy, why first impressions matter, Danny’s concept of ABC ..read more

My guest today is Zac Bookman. Zac is the Founder and CEO of OpenGov a budgeting and financial management software for local governments. Before he founded OpenGov Zac was an Advisor to U.S. Army General H.R. McMaster in Afganistan, a law clerk on the Ninth Circuit Federal Court of Appeals, and earned a Fullbright Fellowship studying corruption in the Mexican government. This conversation is one of the most unique and wide-ranging of any I’ve had on the show. We cover how Zac built a world-class sales organization, the power of selling momentum, and the role capital efficiency still ..read more

My guest today is Daniel Gross. Daniel is the founder of Pioneer, an extremely unique company which he describes as a “fully remote startup generator” that helps talented people around the world figure out if their idea has legs. You can learn more about it at pioneer.app. Our wide-ranging conversation covers the art of asking great questions, the use of predictive modeling and psychometrics to identify talent, and why psychometrics are probably overrated and not that scientific. We then dive into exciting new frontiers for tech investing ranging from GPT-3 to satellites. I really enjoye ..read more

My guest today is Emmett Shear, founder and CEO of Twitch. Twitch is the world’s leading live streaming platform for gamers, which was acquired by Amazon in 2014. We talk about how Twitch empowers streamers to monetize their audience, the necessity of picking a customer early in a business, and the lessons Emmett learned scaling Twitch from an online reality TV show to a global brand inside Amazon. We also discuss how Twitch has helped create a new language in the internet age with emotes, a topic I am fascinated by. I hope you enjoy this conversation with Emmett Shea ..read more

My guests today are Raju Rishi, Nikita Singareddy, and Jason Black of RRE Ventures. RRE is a New York-based VC firm investing in early-stage start-ups with more than 400 investments over its 25 year history. Raju, Nikita, and Jason focus their time in the world of healthcare investing, a topic I haven’t explored much personally or on this show. We discuss the current landscape for healthcare investing, the variety of stakeholders in the healthcare value chain, the opportunities for founders and investors in the space, what excites them most about the future of the space, and the impact COVID ..read more

My guest today is Nick Kokonas, the co-founder of the 3 of the best restaurants and bars in America – Alinea, Next, and The Aviary as well as the co-founder and CEO of Tock, a comprehensive booking system for restaurants. This was one of my favorite conversations in the history of the show. Nick is a philosophy major turned derivatives trader that is now one of the most well-known names in the restaurant and hospitality industry. We cover so many topics I can’t list them here, but I’ll remember it for why it’s so important for a business to really know what it’s selling and then actually sell ..read more