Failing Up

Claire
  • 5.0 (2)
  • BUSINESS
  • UPDATED WEEKLY

Failing Up flips the script on failure and dives deep into the journeys of founders and entrepreneurs as they share their most pivotal setbacks and the invaluable lessons learned along the way. Failure is not a setback, but a stepping stone to success, offering insights that success often obscures. I explore the raw, unfiltered stories behind the most painful lessons.

  1. FEB 10

    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 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?

    1 hr

  2. JAN 7

    The Truth About Biohacking: What Works, What’s Hype, What’s Dangerous

    Biohacking promises better focus, stronger bodies, and longer lives—but where does optimization turn into obsession? In this episode, Anthony from Feel Better Lab breaks down what biohacking actually is, what’s worth doing, and where the ethical line starts to blur. From olive oil and breathwork to concentration studies and the question of living forever, this is a grounded conversation on upgrading the human system without losing your humanity. 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 1:00 - Olive Oil 3:00 - Where Anthony’s love for biohacking came from 11:00 - How biohacking has changed throughout the years 15:30 - Biohacks that are worth it 18:30 - Anthony’s concentration study 25:00 - Breathework/Sound science 30:00 - the line of ethics in biohacking 38:30 - Would you live forever if you could? 48:00 - Will biohacking make us “stronger?” #podcast #selfimprovement #failure #success #entrepreneurship

    52 min

  3. 12/18/2025

    Love, Loss, and the road to a purposeful life w/ John Gillen

    In this episode of Failing Up, I sit down with John Gillen, Co-Founder of True Capital, to talk about love, grief, ambition, and endurance. We explore why marrying for “logistics” is a trap, the real psychology behind heartbreak, how to tell whether ambition comes from passion or avoidance, and why love doesn’t have to be romantic to be meaningful. 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: 00:00 — Introduction 01:00 — Marrying for love and potential vs. “logistics” 11:00 — How to parse through relationship advice 18:30 — Lessons from previous relationships 21:30 — You can’t shortcut your way to a purposeful life 24:30 — The psychology and science behind breakup pain 30:30 — “I will love again. I will live again.” 35:00 — Love doesn’t have to be romantic 39:45 — Building a gratitude practice 48:00 — Ambition: avoidance vs. passion 56:00 — Detaching from outcomes 1:00:00 — You are capable of endurance and suffering 1:05:00 — Grief is learning how to walk with a limp

    1h 16m

  4. 11/26/2025

    #1 NYC Podcast Studio Owner: Be For a Few, Not for Everyone - Why Niches Win

    This week I sat down with Matt Marlinski - Founder of The Manhattan Lab - New York's fastest-growing podcast studios. Matt has hosted politicians like Bernie Sanders, top podcast hosts like Chris Williamson, and produces shows for James Sexton & Anthony Pompliano. A year ago, we recorded together, and we both had no idea where everything was going. Now, we're sitting in the chairs again - one year later - talking about: - Why you don’t need to quit your 9–5 to be a creator - The difference between passion and skill - Why most creators fail before they even start - The new reality of podcasting in 2025 - What it actually means to build for a small, loyal audience instead of millions - And how to grow without losing yourself in the process Watch On YouTube: https://youtu.be/CfflPh9qVlg Follow Us On IG: https://www.instagram.com/failinguppp/?hl=en Timestamps 0:00 — One year later: sitting back in the chair 1:00 — What changed since last year 4:00 — Want balance? Keep a 9–5 7:00 — Passion vs. what you're actually good at 12:00 — Content: the good news and bad news 17:00 — The evolution of podcasting 21:30 — Famous people are still human 27:30 — “Follow the light” philosophy 32:00 — What makes a great podcast 46:00 — Why you should build for a few, not for everyone 47:30 — Advice For New Creators: Take A Long Road #podcast #selfimprovement #failure #success #entrepreneurship

    51 min

  5. 11/21/2025

    Is gambling the solution to our broken financial system?

    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=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 — Welcome John Back To The Show 1:00 — $15B of shorts liquidated 3:12 — The changing culture around investing 13:00 — Everything you need to know about leverage 17:00 — The failure of the American educational system 19:00 — The gambling addiction in stocks 24:00 — Why do men gamble and most women don’t? 28:00 — Why it’s better if your customer needs your product 33:00 — We’ve automated our life into oblivion 38:00 — The opposite of addiction is community 44:00 — Debate on government privacy 55:00 — Thanks John For Joining! #podcast #selfimprovement #failure #success #entrepreneurship

    56 min

  6. 11/12/2025

    How to get a job in the AI economy

    The U.S. job market looks strong — but beneath the surface, everything’s shifting. Previous Wall Street reporter at Business Insider and Opening Bell Daily Co-Founder Phil Rosen breaks down what’s really happening behind the numbers: from “labor hoarding” ending to how AI is quietly rewriting job descriptions. In this episode, we cover: - Why companies are finally cutting after years of over-hiring - Whether AI is a short-term hype cycle or a long-term productivity revolution - The surprising jobs most at risk in the next decade - How to stand out in a market where one person can do what used to take a team - Why confidence and creativity — not credentials — are your new edge 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 - Welcome Phil Rosen! 1:00 - Labor hoarding is over 4:00 - When will stocks catch up to the job market? 9:00 - Is AI a fad or a long-term catalyst? 13:00 - Are blue-collar or white-collar jobs more at risk? 18:00 - What took a team now takes one person 27:30 - How to stand out in this job market 32:00 - Confidence comes from doing 34:00 - Leverage the internet to showcase yourself 38:00 - Thanks Phil For Joining! Like & Subscribe #podcast #selfimprovement #failure #success #entrepreneurship

    38 min

  7. 11/06/2025

    The FBI Agent Who Stopped a Spy Warns What’s Coming Next

    He caught one of America’s most dangerous spies, and now he’s warning the world about what’s coming next. Former FBI and cybersecurity expert agent Eric O’Neill spent years undercover to expose one of the most damaging double agents in U.S. history. Now, he says the next great threat isn’t coming from guns or bombs- it’s coming from AI, deepfakes, and cyber warfare. If you want to understand how the next war will be fought — and how to defend yourself in it — don’t miss this one. In this episode, Eric reveals: - How he helped take down a spy who betrayed the U.S. - The biggest cyberattacks in American history — and what we learned - How AI bots are reshaping the way we think and the way we act - Why social media has become a national security risk - What truth looks like in the age of disinformation - The rise of “romance fraud” and how to protect yourself Eric’s Book: Spies, Lies & Cybercrimes Website: ericoneill.net Instagram: @ericoneill.official Follow Us On IG: https://www.instagram.com/failinguppp/?hl=en Watch On YouTube: https://youtu.be/zar5Fw7wMno TIMESTAMPS: 0:00 - Intro 1:30 - Taking down a spy who betrayed the U.S. 05:30 - The U.S.’s worst cyberattacks and how we’ve adjusted 11:30 - How equipped is the U.S. to deal with cyber attacks? 20:00 - Why are other governments creating bots? 25:00 - Social media is a net negative 31:00 - Put your mind in a state of boredom 34:00 - How to find the truth in the age of deepfakes 41:00 - Countries should police their own cyberspace 44:30 - “Romance fraud” and how to stay safe from it 56:00 - Thanks Eric for joining the show! Like & Subscribe #FBI #SpyHunter #Cybersecurity #Deepfakes #AI #CyberWar #Espionage

    56 min

  8. 10/29/2025

    How the U.S. Lost Control to China — And What It’ll Take to Get It Back | Steve LeVine

    Steve LeVine, editor of The Electric and writer at The Information, joins to unpack how the U.S. became dangerously dependent on China and what it would take to unwind that relationship. We cover everything from the forgotten origins of this dependence to the geopolitical choke points defining the next global conflict — minerals, semiconductors, and influence across Africa. 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 - Welcome Steve LeVine To The Show! 1:00 — How the U.S. became so dependent on China 4:45 — The downside of $100,000 H-1B visas 10:55 — How “Not In My Backyard-ism” paralyzed American industry 15:00 — Is decoupling from China even possible? 20:00 — China’s dominance in Africa vs. the U.S. 30:00 — Why rare earth minerals matter most 32:30 — How China plans to outmaneuver the U.S. in semiconductors 37:00 — Why China has America in a chokehold 46:00 — The U.S. administration’s aggressive trade stance 50:00 — The real path to U.S. independence from China 1:07:00 - Thanks For Watching! Like & Subscribe #podcast #geopolotics #china #failure #success #entrepreneurship #technology #ai

    1h 7m
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Ratings & Reviews

5
out of 5
2 Ratings

About

Failing Up flips the script on failure and dives deep into the journeys of founders and entrepreneurs as they share their most pivotal setbacks and the invaluable lessons learned along the way. Failure is not a setback, but a stepping stone to success, offering insights that success often obscures. I explore the raw, unfiltered stories behind the most painful lessons.

Information

  • Creator
    Claire
  • Years Active
    2024 - 2026
  • Episodes
    32
  • Rating
    Explicit
  • Copyright
    © Claire
  • Show Website
    Failing Up