Don’t Let Life Harden You: Staying Optimistic When the World Gets Cynical with John Gillen

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 mindsetFollow 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 - Zohran’s budget problem in NYC11:00 - Responsibility to speak on issues16:30 - Operating with Eternal Optimism30:00 - Don’t let life harden you39:00 - Are we all too jaded?