He built 2 billion dollar companies. here's his one rule

How can you be the best CEO across every phase of your company?Get Jason's full founder operating system in our free newsletter: https://truewealthshow.com/download-guide/In this episode, True Wealth hosts Anthony Ng Monica and Fintan Costello sit down with Jason Cohen, founder of SmartBear and WP Engine, two companies that went on to become unicorns.But this conversation isn't really about building billion-dollar businesses. It's about how to be the best leader possible at every stage of a business’s growth.From how to make the best decisions, to building a company culture that matters, Jason shares his entire CEO mindset and strategy.He also confesses why stepping down as CEO of WP Engine was one of the best decisions he ever made, what most founders misunderstand about growth, and how to avoid wasting years on the wrong problems.You'll learn:- Why Jason stepped down as CEO of WP Engine- The 3 traps that lead founders into burnout- How to know if you're working on the right thing- Jason's framework for building high-performing teams- A simple hiring technique that reveals cultural fit- How to make better decisions under uncertainty- Why founder ego can become your biggest liabilityAbout Jason Cohen:Jason Cohen is the founder of SmartBear and WP Engine, two software companies that grew into unicorn businesses. He is also the author of A Smart Bear, where he has spent nearly two decades writing about startups, decision-making, leadership and entrepreneurship.Follow Jason:- Website: https://longform.asmartbear.com- X: https://x.com/asmartbear- A Smart Bear: https://longform.asmartbear.comFollow True Wealth:- Instagram: @truewealthshow- TikTok: @truewealthshow- Anthony on LinkedIn: https://uk.linkedin.com/in/anthonyngmonica- Fintan on LinkedIn: https://nl.linkedin.com/in/fintancostello- True Wealth website: —-link—-Book a direct call at Daily Body Coach with Anthony: https://www.dailybodycoach.com/00:00 He built two billion-dollar companies – here's how01:11 Your team works on the wrong thing – here's why02:16 The decision that changed everything at 80 people03:02 When you have a choice between money and time04:24 Why WP Engine could become multi-billion dollar05:46 Raising money isn't about growth – it's about freedom06:52 The fundraising strategy nobody talks about08:31 How to screen investors so they don't replace you10:44 Hiring for culture – the reference check technique12:41 The question that reveals who someone really is15:03 Testing for ownership in interviews17:46 The trap every talented founder falls into19:45 Why you burn out doing what you love21:39 The joy-need trap that destroys founders22:34 Burnout isn't weakness – it's a decision you made24:48 How to stop destroying yourself26:54 Bascamp's strategic choice most founders miss27:27 The CTO move that saved his life27:48 "I hate managing people" – and why that matters28:14 Company size changes everything – the rule of 3s32:00 Why difficult conversations get harder at scale33:32 The technique that makes hard conversations easier35:30 What they don't tell you about post-exit life38:09 Money solves money problems – nothing else39:00 The psychology of wealthy founders42:10 What billionaires actually spend money on44:33 The mistake founders make with wealth47:50 The 30-day ritual that changes how you see51:55 "Two big things but not three" – the real constraint53:42 Your company is your baby – brain scans prove it55:01 22 out of 23 founders experience this after exit56:50 What happens to founders who can't find the next thing59:53 SmartBear taught him about burnout – the hard way1:00:15 Culture is strategy – not soft stuff1:01:17 What he learned from each exit1:06:40 Find your unique intersection – that's your advantage1:08:26 Building a book system instead of a business1:14:21 The irrelevance clock starts ticking#wpengine #entrepreneurship #truewealth