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The Calum Johnson Show
The Teacher Who Invested In AI: How To Become A Millionaire On A 9-5 Salary (Painfully Simple!)
⏱ 78 min video · 4 min read18 May 2026Worth watching
TL;DR
Troy (co-founder of Earn Your Leisure) shares how he turned $100,000 into $1.3 million in 10 months by investing in tech ETFs during the pandemic, and argues that AI represents the greatest wealth transfer of this generation. The conversation covers his Jamaican immigrant upbringing, financial trauma, and a practical framework for how anyone — even with just $50 — can start investing using AI tools like ChatGPT and Claude.
Key points
1
Troy invested $100,000 split equally across three tech ETFs (SMH, XLK, XLY) in June 2020 and watched it grow to approximately $1.3 million in 10 months — roughly 1,200% average appreciation across each position.
2
He argues AI is the greatest wealth transfer of this generation, comparing it to the industrial and internet revolutions, and warns that those who do not participate financially and technologically will be left behind permanently within 2-3 years.
3
His $50 starting point framework: spend $19.99 on an Anthropic (Claude) subscription, $19.99 on OpenAI (ChatGPT), and use the remaining money to buy a book, then systematically prompt these tools to learn investing fundamentals — ETFs, index funds, dollar cost averaging, brokerage accounts.
4
Financial trauma is a real barrier: Troy recounts how his parents refused to refinance their mortgage during COVID-19 even though it would have saved them $300/month, because the trauma of losing their home years earlier left them paralyzed with fear.
5
Wealth is built through two primary vehicles — appreciating real estate and appreciating business equity — and the AI era is making it possible to build multi-million dollar companies with one or two people, which means traditional employment is shrinking fast.
Actionable insights
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Start with $50: use ~$40 on ChatGPT and Claude subscriptions, then spend weeks prompting them with beginner investing questions — brokerage selection, ETFs, index funds, dollar cost averaging — before committing any capital to the market.
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Use multiple AI tools simultaneously (ChatGPT, Claude, and free Gemini) as three independent sources of financial education, then cross-reference their answers to build a rounded understanding before executing any investment.
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When building a business, ask AI: 'How do I create a business with low overhead but high profitability that can scale?' — then drill into whichever option interests you with follow-up prompts on scaling, partners, and finding clients.
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Connect Gamma to ChatGPT (via Settings > Apps > Add More) to generate a visual 30-day investing learning plan — useful for people who are visual learners and want a structured roadmap rather than open-ended prompting.
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Treat AI participation as urgent: Troy argues the window to get on the right side of this wealth transfer is roughly 2-3 years, after which the gap between participants and non-participants will be too large to close.
Notable quotes
“$50 is more than enough.”
“I watched fear paralyze you and I don't want to do that and I don't want to become that. So I'm gonna take chances and I'm going to live carefree.”
“The people who are creating the prompts, the people that are creating the agents in the large language models, they don't look like us. They don't sound like us. And they're creating it in their language.”
Worth watching?
✅
Worth watching the full video?
Watch if you want Troy's full emotional storytelling and the energy behind his conviction — the key strategies and frameworks are all captured here, but his delivery adds real motivational weight that the summary cannot fully replicate.
Saved you some time? The creator still deserves a like.
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