"TradeMe nearly failed... then we sold for $750 million" - Rowan Simpson on how to make millions in startups

There’s investing, and then there’s "Capital I Investing", the one that comes with big risk, and if it works, big reward. Today’s guest Rowan Simpson is someone who’s flown under the radar in that scene for a while, first working at some of our iconic tech startups, and then investing in them. Rowan Simpson started out by saving up $10,000 to create his own tech company, Flathunt.co.nz. He’s since gone on a journey that involves TradeMe, Xero, Vend, and Timely, iconic companies, and he’s got millions more than that first $10,000. Now, he’s a private and early-stage venture investor, keeping an eye out for that next great business that can take the world by storm. So how did he get from $10,000 to tens of millions… and what does he want the rest of us to know, before we try to copy him? Follow me everywhere! Facebook / https://www.facebook.com/FrancesCookNZ/ Instagram / https://www.instagram.com/francescooknz/ TikTok https://www.tiktok.com/@francescooknz Join the Money Memo newsletter for a free weekly money tip in your inbox each week https://www.francescook.co.nz/subscribe #makingcents #francescook #rowansimpson #trademe #investingforbeginners #entrepreneurlife Chapters 00:00 - Introduction 01:52 - Rowan’s First Startup 05:02 - Trade Me’s Near Death Experience 07:20 - Identifying Successful Ideas 11:39 - The Reality of Startup Life 17:00 - Learning from Mistakes 19:56 - The Role of Ego in Business 21:18 - The Compounding Effect of Success 25:56 - Private Investing 29:13 - Rowan’s Involvement With Companies 30:45 - How To Identify A Good Founder 31:53 - Angel Investors 35:29 - Diworsification 41:03 - Balancing Life With Startups 42:42 - New Zealand’s Business Reality 45:28 - Advice To Founders 47:26 - Pro Capital Gains Tax 52:38 - Reaching Financial Freedom 54:07 - Advise To Investors 55:35 - “How To Be Wrong” 56:49 - Conclusion