Anthony Casalena is the Founder & CEO @ Squarespace, the company that allows you to create a website, sell anything and market your business. To date, Anthony has raised over $948M for the company from the likes of General Atlantic, Index Ventures, Tiger Global; culminating in their IPO in May 2021. Despite the incredible size and scale of Squarespace today, Anthony started the company from his dorm room in 2003 and bootstrapped the business for many years to today with over 1,100 employees around the world. In Today’s Episode with Anthony Casalena You Will Learn: 1.) How Anthony came to start Squarespace from a dorm room and turn it into a public company with over 1,200 employees globally? 2.) Why did Anthony decide to bootstrap with Squarespace for over 6 years when the company was scaling fast and profitable? How was Anthony's mindset impacted by the efficiency of bootstrap scaling? How did Anthony's mindset change when Squarespace raised their first large round? How does Anthony advise founders today on raising venture vs bootstrapping? 3.) Why did Anthony decide to do the direct listing over the more traditional IPO or a SPAC? How does Anthony advise other founders contemplating the same exit choices? How does Anthony personally describe this chapter of the company? Does he enjoy being a public company CEO? What are the best elements? What are the worst? 4.) E-Commerce has been a massive driver for growth for Squarespace, how does Anthony feel about the future of e-commerce on Squarespace? Only 1% of Squarespace's $700M ARR comes from enterprise, does enterprise hold a meaningful position in the future of the company? What are the core challenges of moving into enterprise? How does the company need to change? 5.) With the growth of the company, how has Anthony changed his style of leadership? What are his biggest strengths? What are his biggest weaknesses? What are the most obvious breakpoints in the scaling of companies? Item’s Mentioned In Today’s Episode with Anthony Casalena Anthony’s Favourite Book: Thinking Fast and Slow

Keith Rabois is a General Partner @ Founders Fund, one of the most successful venture firms of the last decade with home runs in the likes of SpaceX, Palantir, Stripe, Anduril, Facebook, Airbnb, Nubank and many more. As for Keith, he led the first institutional investments in DoorDash, Affirm and has also led investments in Ramp, Trade Republic, Faire and Stripe. Prior to venture, Keith had the most stellar operating career, joining PayPal when their monthly burn-rate was $6 million; Keith joined LinkedIn, Slide and Square when they had no revenue. Fun fact, five companies Keith helped build are now publicly traded with market caps >$1 Billion. Three others have been acquired for greater than $1 Billion or are publicly traded IPOs. If that was not enough, Keith is also the Co-Founder and CEO @ OpenStore, acquiring small DTC businesses. In Today’s Episode with Keith Rabois You Will Learn: 1.) How Keith first came up with the idea for Opendoor? How a conversation with Peter Thiel led to the founding of the first iteration of the company? Why did it take Keith close to a decade to pursue the idea fully, post having the idea in 2003? 2.) The Market: What made Keith so excited to pursue Opendoor from a top-down market analysis perspective? What does Keith look for in markets he likes to invest in? How did Keith expect the market to change and evolve? What did the market do differently to how Keith thought it would behave? 3.) The Business Model: With debt being the oxygen for Opendoor, how many homes did they need to acquire before they could prove they could price homes accurately? What were Keith's lessons from the first homes they bought? What did not go to plan? Why does Keith disagree, if macro hits real estate, Opendoor's model is challenged? Why does Keith believe it is stronger then? 4.) The Team: What does Keith look for in the founding teams he backs? How does Keith detect diamonds in the rough? How can teams systematically de-risk an opportunity with their experience? With the benefit of hindsight, what would Keith have done differently with the team? 5.) The Funding: Was fundraising for Opendoor always easy? How did the seed round go down? How does Keith feel today about pre-emptive rounds where little company development has taken place? Why did Opendoor decide to SPAC? Why not a direct list? Was this the right choice? What makes for the best SPAC partner?