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?

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

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.

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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

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

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

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

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

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

Dating today is broken. In this episode, Dini, co-founder of AI matchmaking app Sitch, joins Failing Up to talk about how we got here — from OkCupid to Hinge to whatever comes next and why it might finally be time to reinvent dating altogether.

We explore the paradox of choice, the gender wars,  what healthy conflict resolution in relationships look like, and why so many people chase chemistry over compatibility. Dini explains how AI could reshape human connection by removing ego, bias, and the endless swiping culture that’s left so many people burned out and disillusioned.

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 Dini To The Show!

1:00 - Dating Today - paradox of choice

4:00 - We had OkCupid, then Hinge, and now ????

7:00 - B2B AI SaaS your love life?

12:00 - Compatibility & Connection

18:30 - The gender wars

22:00 - What guys vs girls do wrong (expectations and practices)

31:00 - Why is there a stigma attached to dating coaches?

38:00 - Couples should always have separate bathrooms

40:00 - What we all misunderstand about love and what’s really important

46:00 - The keys to good conflict resolution

50:00 - Thanks For Watching! Like & Subscribe

In this episode of Failing Up, John Gillen joins Claire Barthelemy for a deeply human conversation about losing faith in politics — and finding balance in life. We what it means to stay grounded in a divided world, the cost of being the “sane voice,” and how forgiveness, gratitude, and listening can rebuild both our personal and collective sanity.

From the chaos of political discourse to the quiet lessons of love and self-awareness, this conversation reminds us that balance isn’t found in certainty, it’s found in understanding.

Follow Us On IG: https://www.instagram.com/failinguppp/?hl=en

Watch On YouTube: https://youtu.be/IZSD7xVO5hU

Timestamps:

 0:00 – Introduction

 1:00 – Zohran and the repercussions of winning as mayor of NYC

 11:00 – The alternative realities of the right & left

 21:30 – Fallout after Charlie Kirk from both sides

 25:00 – Appreciating both sides of the spectrum

 27:00 – Listen to understand

 31:00 – The consequences of trying to be the sane voice

 37:00 – Individualism vs collectivism

 39:30 – 69% of young adults ending relationships due to “toxicity”

 44:30 – You can’t love someone into changing

 51:00 – Balancing self-love & relationships

 54:30 – The importance of boundaries

 1:00:00 – Forgiveness as alleviating revenge

 1:05:00 – Gratitude & joy for the little thing

#podcast #selfimprovement #failure #success #entrepreneurship #politics