Failing Up
Claire sits down with John Gillen — Co-Founder of True Capital and host of Milk Road Macro — for a conversation about responsibility, resilience, and staying optimistic when the world feels cynical. From New York City’s budget crisis to the pressure of speaking out on public issues, John shares why he chooses eternal optimism — even when it’s unpopular. We talk about: - why leaders have a responsibility to speak - how politics affects everyday life more than we admit - the danger of becoming jaded - why the hardest thing to protect isn’t money — it’s your mindset Follow Us On IG: https://www.instagram.com/failinguppp/?hl=en Listen on Spotify: https://open.spotify.com/show/3KMsmkqvycGgoXZDjoM6Py?si=6e40e75d54374c08 Listen On Apple Podcasts: https://podcasts.apple.com/us/podcast/failing-up/id1771458449 Timestamps: 0:00 - Zohran’s budget problem in NYC 11:00 - Responsibility to speak on issues 16:30 - Operating with Eternal Optimism 30:00 - Don’t let life harden you 39:00 - Are we all too jaded?
33 episoder
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