Jon Callaghan is a founder of True Ventures, one of the West Coast's leading early stage funds with a portfolio including the likes of Fitbit, recent unicorn Peloton, Automattic (makers of Wordpress) and more amazing companies. Jon also led the deals and sits on the board of Fitbit, Brightroll, Peloton and Glu Mobile, just to name a few. Prior to True, Jon founded 3 of his own companies, the first being in 1986 with Mountain Bike Outfitters Inc. Following several years founding companies, Jon made his move into VC with Summit Partners and then enjoyed roles with AOL's venture incubator, CMGi's Venture group and Globespan Capital. In Today’s Episode You Will Learn: 1.) How Jon made his first forays into the world of VC and came to co-found True with Phil Black? 2.) How does Jon look to straddle the divide of "founder/VC"? Why does Jon believe it is crucial to have an entrepreneurial mindset as an investor? 3.) Why does Jon believe VCs biggest bias is loss aversion? Why does Jon always believe that the role of the VC is to maximise risk? What 1 thing must all prospective investors get good at very quickly? 4.) How does Jon view reserve allocation? True invest -1% per deal in each company, how do they look to efficiently deploy reserves? What must the communication be between founder and VC with regards to attaining follow on funding? 5.) Why does Jon believe that current board meetings do not serve startup founders? What are the characteristics of the best board members and how they conduct themselves? What is the single biggest problem boards bring to founders? Items Mentioned In Today’s Show: Jon’s Fave Book: Moby Dick Jon’s Fave Blog: Dave Pell: NextDraft Jon’s Most Recent Investment: Brava As always you can follow Harry, The Twenty Minute VC and Jon on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. Pendo delivers the only complete platform that helps companies create great products. The Pendo Product Experience Platform enables product teams to understand product usage, collect user feedback, measure NPS, assist users, and promote new features in-app – all without requiring any engineering resources. This unique combination of capabilities helps companies improve customer satisfaction, reduce churn, and increase revenue. Pendo is the proven choice of Salesforce, Cisco, Optimizely Citrix, BMC and many more leading companies. Start a free trial at http://go.pendo.io/harry Treehouse is an online school where you can learn how to build websites and apps. Their course library has thousands of hours of content, where you can learn all sorts of topics, including Javascript, iOS, Android and more.  With high-quality video instruction from real industry experts teaching you all you need to know, and quizzes and code challenges keep you engaged and on track. Learn on your own schedule and go from beginner to pro. Go to teamtreehouse.com to start your free trial.