Mario Schlosser is the Founder & CEO @ Oscar, the startup that makes health insurance easy. They have raised over $700m in funding from some of the world's best investors including the likes of Founders Fund, Google Capital, Thrive Capital, Lakestar, Khosla Ventures and Jim Breyer just to name a few. Previously, Mario co-founded the largest social gaming company in Latin America and held roles with the likes of Bridgewater Associates and McKinsey. Fun fact, as a visiting scholar at Stanford University, Mario wrote 10 computer science publications, including one of the most-cited computer science papers published in the past decade. In Today’s Episode You Will Learn: 1.) How Mario made his way into the world of healthcare and Oscar from founding Latin America's largest social gaming company? 2.) Why is insurance one of the most complex spaces in tech? Why is there a chance for companies, not governments, to cut costs and innovate on the current system? Does Mario agree with Brian Singerman, "once we go to a single player, innovation ends", thesis? 3.) Oscar has raised over $700m, to what extent does Mario believe that too high a valuation can be a liability? How did Mario look to select his investors? What are the challenges of raising funds for a category-defining opportunity? 4.) Oscar now has over 600 in the team, where have been the inflection points in the scaling of the company? Where have things broken? How does Mario look to rectify and observe these inflection points ahead of time? 5.) How does Mario look to optimise team composition? How does he look to balance athletes with heavy domain experts? Does Mario believe that too much domain expertise can prevent innovation due to a lack of naivety? Items Mentioned In Today’s Show: Mario’s Fave Book: Herr Lehmann Mario’s Fave Blog: Spiegel As always you can follow Harry, The Twenty Minute VC and Mario on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.