My guest this week is a good friend and a business mentor of mine. Chetan Puttagunta is a general partner at Benchmark Capital and has a remarkable track record of investing in early-stage software businesses, including several like Mulesoft, MongoDB, and Elastic that went on to be public companies. Chetan has been my key guide for understanding the world of enterprise software as we at O’Shaughnessy Asset Management have built an investing platform called Canvas. His advice has been critical to our early success. In this episode, we explore the history of software and software investing, and go into the details on how to build and grow new software businesses. We discuss product, sales and marketing, recruiting, scaling, and everything in between. Please enjoy this great conversation with one of my favorite business and investing thinkers. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:34 – (First Question) – How Chetan found MongoDB and decided to invest in it 8:01 – The evolution of databases in the growth of technology 16:19 – Market penetration of this space and what investors should be thinking about 21:46 – Advice how companies can build software effectively 25:12 – Tactics to effectively implement empathy led product building 30:33 – Companies asking users what to build vs telling users what they want 34:26 – The need for the right capital, and patient capital in particular 37:55 – Creating the perfect customer experience 44:37 – Common reasons they don’t invest in a company 48:48 – Lessons on scaling, especially in sales and marketing 52:47 – Best recruiting pipeline strategies 59:56 – Pitfalls of unit economic traps 1:00:23 – The Dangerous Seduction of the Lifetime Value (LTV) Formula 1:01:34– The Hierarchy of Engagement 1:02:18 – What has changed for Chetan in his time working with the team at Benchmark 1:06:009 – Later stage life cycle business considerations and Amazon’s AWS 1:13:29 – The business model of open-source software 1:15:54 – Being default open 1:17:53 – Kindest thing anyone has done for Chetan Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag