As a four time entrepreneur over more than 15 years, what are the biggest lessons learnt in management, levelling up as a founder and coming up with business ideas? Jason Cohen from WP Engine talks to us about why he decided to raise funds after bootstrapping successfully in the past, and how he comes up with business ideas. We also talk about evaluating your managers, how managing your executive team is very different from managing other members of the team, how the role of a founder evolves over the years and the different ways that you can level up as one. ⏱ What you’ll find and when: 00:00 Intro 07:33 Reasons to raise funds after being a successful bootstrapper 12:50 Jason’s thoughts on financial reporting 23:45 The best way to evaluate your managers 30:05 Acquisitions: impact, challenges, successes 38:18 Coming up with $1B business ideas 44:36 How the role as a founder evolves over time 51:25 Levelling up as a founder 57:52 How to successfully manage an executive team 69:33 Where you can find Jason 🔗 Connect with Jason: Twitter: https://twitter.com/asmartbear Blog: https://blog.asmartbear.com/