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?
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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