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When? 📆 Saturday, September 19th

What I’d Do Differently With My First $500,000

Between 2013 and 2018 I deployed $530,000 across nine investments while I was still working full time in tech. It worked. That capital paid me real income from the first year, and it became the foundation of the portfolio that now generates around $200,000 a year.

It also took far more work than it needed to.

I’ve put millions to work since then, and I’ve watched which decisions hold up across cycles and which ones only worked once. Standing at that same crossroads today, with the same $500,000 and the same goal, I’d build it a completely different way: fewer investments, fewer operators, and a lot less of my own time.

In this video I walk through the original deployment in detail, what each piece returned, and the five principles I’d follow instead if I were starting tomorrow. The shift that drives all five runs against everything my tech career taught me about what makes something valuable.

If you’re sitting on capital you want to turn into income, this is the framework I wish I’d had in 2013.

This is education, not advice. Let’s keep building.

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Disclaimer: This newsletter is for informational purposes only and does not constitute financial or career advice. Always consult with qualified professionals before making any decisions based on the information provided.

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