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Failing Up

Is gambling the solution to our broken financial system?

21 Nov 2025

Description

I sit down with John Gillen — Partner at True Capital and host of Milk Road Macro — to break down how modern investing is shifting from long-term wealth building to dopamine-driven risk-taking.They talk about the rise of leverage, why gambling behavior is exploding among retail traders, how automation has rewired discipline, and why the opposite of addiction isn’t willpower — it’s community. We also debate one of the biggest questions of our time: Should the government have access to your data — and where is the line between safety and surveillance?Follow Us On IG: https://www.instagram.com/failinguppp/?hl=enListen on Spotify: https://open.spotify.com/show/3KMsmkqvycGgoXZDjoM6Py?si=6e40e75d54374c08Listen On Apple Podcasts: https://podcasts.apple.com/us/podcast/failing-up/id1771458449TIMESTAMPS: 0:00 — Welcome John Back To The Show1:00 — $15B of shorts liquidated3:12 — The changing culture around investing13:00 — Everything you need to know about leverage17:00 — The failure of the American educational system19:00 — The gambling addiction in stocks24:00 — Why do men gamble and most women don’t?28:00 — Why it’s better if your customer needs your product33:00 — We’ve automated our life into oblivion38:00 — The opposite of addiction is community44:00 — Debate on government privacy55:00 — Thanks John For Joining!#podcast #selfimprovement #failure #success #entrepreneurship

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