Failing Up

Failing Up
Podcast Description
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.
Podcast Insights
Content Themes
The podcast explores themes surrounding entrepreneurship, resilience, and personal development, with episodes touching on topics such as the challenges of starting a business in a small market, the implications of AI in various industries, and the importance of forgiveness in personal life with examples from guests like Jack Kuveke discussing crypto ventures and Naomi exploring domestic abuse survival.

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.
John Gillen left BlackRock to launch his own crypto fund — but this episode goes way beyond markets.
We talked about the political shift around crypto, why it shouldn’t be a partisan issue, and whether Bitcoin could realistically hit a $50 trillion market cap.
John also opened up about his personal philosophy — on time, consciousness, free will, and the emotional complexity of modern relationships.
We also explored:
— The Christian model for forgiveness
— How betrayal fractures trust and identity
— The role of emotional intelligence in both connection and conflict
— Why good friends can change how you love
— Whether time is a real phenomenon — or just a perceptual bias
A wide-ranging, thought-provoking episode that blends crypto, consciousness, and self-awareness.
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TIMESTAMPS:
0:00 – Welcome John Gillen To Failing Up?
2:00- Working at Blackjack versus being an entrepreneurship in crypto
6:00 – Is what the Trump administration for crypto permanent or reversible?
8:00 – Why John thinks crypto should not be a “partisan issue”
11:00 – Crypto/Blockchain uses in real time
13:00 – Bitcoin market cap predicition: 50 trillion (is this viable)?
16:00 – Time is real but it is a cognitive perceptual bias
21:30 – Consciousness and how other religious teachings can be applied towards consciousness
26:00 – the Christian Model for forgiveness
29:27 – Betrayal trauma is like your head getting smashed into glass because the wounds go in all different parts of yourself
35:18 – It takes a lot of violence to be this gentle
41:00 – How to maintaining integrity while dating
45:00 – Where John thinks emotional intelligence comes from
46:30 – Good friends show you how you should be treated in a relationship
49:00 – Two people look at a painting, one cries, one asks “what time is lunch?”
#podcast #selfimprovement #failure #success #entrepreneurship #technology #ai

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