From $50 to Millions: Investing Tips I Wish I Had at 17 💸
He flipped a coin on a café table and accidentally rewired how New Zealand invests. 🎧 Listen on:👉 Spotify – https://spoti.fi/4is21QI👉 Apple Podcasts – https://apple.co/42KZ2x1New Zealand entrepreneur Leighton — co-CEO of Sharesies, ex-Army trumpeter and accidental brewery founder — walks us through the wild arc from $50 teenage investment clubs to running an 800-thousand-user wealth platform. You’ll hear how a three-week basic-training stint, a coin toss, and a missed $2 000 Ethereum buy shaped a mission to “create one million millionaires.”Beyond the fintech origin story, Leighton drops candid takes on democratizing wealth, AI’s takeover of customer support, and why luck (plus ruthless execution) still beats perfect strategy. If you like your startup talk seasoned with brass-band anecdotes and beer-keg logistics, this one’s for you.Key Topics:🥇 $50 to Financial Freedom — teen investment clubs & compounding power🎺 Army Band to Boardroom — leadership lessons from marching drills🏦 Building Sharesies — fractional shares, regulation hacks & 3 co-CEOs🤖 AI & Customer Care — 85 % of support now LLM-powered📊 Democratizing Wealth — S&P-500 dominance, KiwiSaver gaps🍺 Waitoa Beer Pivot — scaling a brewery during COVID lockdowns🔮 Macro & Geopolitics — optimism, over-indexing and the US angst🔧 Founder Tactics — dollar-cost averaging, hiring through call-centres💡 Future Trends — why “problem first, tech second” still wins🤝 Connect with LeightonLinkedIn: https://www.linkedin.com/in/leightonroberts/🔗 Learn more about NZVC & HostsNZVC: https://www.nzvc.co.nzMark Pavlyukovskyy – https://www.linkedin.com/in/pavlyukovskyy/Hendrik Remigereau – https://www.linkedin.com/in/hendrik-remigereau-09a03067/⏰ Timestamps00:00:00 – Intro & Hawera childhood 00:05:12 – Dreaming of pilot wings and trumpets 00:10:30 – Army band life & leadership lessons 00:17:45 – $50 investment club genesis 00:24:20 – The coin-flip that led to KiwiBank 00:31:50 – Founding Sharesies: six co-founders, one vision 00:42:05 – AI takes over 85 % of support tickets 00:48:40 – Democratizing wealth vs “Robinhood gambling” 00:55:15 – Waitoa Beer, COVID pivots & side hustles 01:03:00 – AI, robotics and the next 5 years of startups 01:10:45 – Closing thoughts on luck, family & tech futures If this chat lit a spark, smash Like, hit Subscribe, and drop your biggest takeaway in the comments—let’s build those million millionaires together!#startups, #business, #NewZealand, #fintech, #AI, #robotics, #entrepreneurship, #wealth, #investing, #Sharesies, #KiwiTech, #startupstory, #VC, #innovation, #techpodcast, #founder, #bootstrapping, #leadership, #futureofwork, #financialfreedom
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