Ryan Deiss Built a Business Empire and His Wife Said "You Can't Pretend This Is For Us Anymore"

He had 3 companies on the Inc 5000 list. He couldn't remember his last vacation. Then his wife gave him an ultimatum. ================== Ryan Deiss is a serial entrepreneur, author, investor, and founder of Digital Marketer and Scalable.co He's built, acquired, and invested in multiple B2B media, service, and software companies, and created Traffic and Conversion Summit, one of the biggest digital marketing conferences in North America. In this episode, he shares how having three companies on the Inc 5000 list nearly cost him his marriage, why he now takes 30 days off every year and his business grows faster because of it, and why most founders stuck between $2M and $8M are following the exact wrong advice. 👉 Brought to you by Prosperum Digital. If you want to add AI to your business without the tech overwhelm, start here: https://prosperumdigital.com.au ================== Connect with Ryan: https://scalable.co/⁠ ⁠https://www.ryandeiss.com/⁠ ⁠   / @ryandeissofficial   ⁠  / ryandeiss   ⁠  / ryandeiss   ================== 👉 Looking to add AI to your business or build a marketing engine around your brand? We help experts and business owners systemize, automate, and scale with digital solutions without the tech overwhelm. Let's have a chat: https://prosperumdigital.com.au/zoomw... ================== #sheefanshow #business #founders #YouTube #entrepreneurship #scaling 00:00 Introduction 01:07 Why Most Business Advice Falls Into Two Bad Categories 04:22 Not Everybody Is Meant to Be an Olympian 06:02 The Night His Wife Held Up a Mirror 10:30 Two Commitments That Changed Everything 13:46 Why Less Time Made Him More Productive 15:14 From Two Weeks Off to 30 Days Every Year 17:40 90 Day Sprints Over Annual Planning 19:09 30 Projects Greenlit, 3 Got Done 21:34 How the Scalable Operating System Was Built 23:30 No Man's Land: The $4M to $6M Trap 28:34 Why You Should Stop Trying to Hire A Players 30:34 Your First Hire Should Not Be an Assistant 33:47 Build a Company That Does Not Require Rockstars 35:36 Invert Any Business Advice and See If It Still Holds 37:58 How to Think About AI Without the Hype 40:15 From Toy to System: The AI Shift 46:42 Why Choosing Your Competition Is a Strategic Decision 53:34 What Is Next for Ryan Deiss