A Deep Dive with Justin Caffrey on Happy Pear Podcast @JustinCaffrey
A Deep Dive with Justin Caffrey on Happy Pear Podcast  @JustinCaffrey
Uploaded August 2022 | Updated September 2026, 1 day ago
This is the full interview I did with David & Stephen Flynn from the Happy Pear on their hugely successful podcast.

This is interview is available on Spotify, Apple Podcasts, Apple Music or wherever you get your podcasts.

00:51 psychological safety as a tool for high-performance

03:01 Find the capacity to be able to say what is needed

03:40 Speaking Truth to Power.

05:15 High-Performance teams and Psychological Safety.

06:16 Absolute Honesty (Candour)

07:02 You Have a bogey hanging out!

08:46 Vulnerability & Humility in Leadership

10:00 Young people are changing the workforce

12:02 Leaders either evolve or die

14:29 Being Authentically You

14:54 The power to speak up drives ideas

15:15 Pay is not the single determiner of staff retention

16:15 Psychological Safety Drives Profits!

21:00 Doing Less to accomplish more.

21:41 From Ruthless to Awareness

25:32 Meeting people where they are (Jurgen Klopp). High-performance Teams

26:40 Fight-Flight & Psychological Safety & Polyvagal Theory

29:45 Win negotiations through Breath & Mindful Awareness

36:45 Justin's back story without Psychological Safety (nobody coming to save you)

42:30 Joshua, his life and death

49:55 In tragedy, you have to find hope and meaning

56:19 Choosing the more difficult path (washing the dead baby) as a high-performance team or leader.

59:11 Running away from difficulty

1:06:09 The opportunity to change

1:08:36 If you don’t face the reality of your life, life will come and get you

1:14:19 Justin 2.0 the recipe & the arrest!

1:23:50 The bear story

We discuss my history and backstory.

Holding a Master’s in Psychological Interventions using Neuroscience and Mindfulness from University College Dublin. Justin is also trained as a Psychotherapeutic Coach, an Accredited Wellness coach from the Mayo Institute and a Certified Investment Fund Director. He is one of only a handful of Westerners to complete the gruelling Masters's Training with the Yamabushi in the remote mountains of Shonai in Japan!

In 2010, at the peak of his career as a dynamic CEO, having founded multiple investment firms, Justin’s son Joshua died – just before his first birthday. Business carried on as normal until 2014, when Justin had what turned out to be a panic attack in the middle of a crucial meeting. He had failed to grieve his son’s death.

In the year that followed his life and health started to unravel. The cause was not Joshua’s death, but the trigger. The CEO had lacked the psychological safety to speak about his emotions and vulnerabilities, no matter the situation.

It would be 2016 before Justin started talking about his vulnerabilities publicly. Fearing it would be a career-ending moment, Justin spoke about the psychological vulnerability he encountered after his son’s death and the constant barrage of negative self-talk. Awaiting judgment, he received only praise and gratitude. Colleagues, clients, and strangers all found something within his words.

Justin is a skilled storyteller narrating his professional and personal journey in a way that everyone from boardroom to kitchen tables can relate to . We all have difficult events in life, he shares how losing his son at the peak of his city career, was ultimately a blessing, and how we can all turn around any challenges we face in life.

Despite the tragedy of his son’s death, this episode will leave you feeling hopeful, broaden your awareness of what it truly means to feel safe in your personal and work enviroment, and of course for any founders, leaders and CEO’s out there, how to get the best out of your employees!

MEDICAL DISCLAIMER: This content (the video, description, links, and comments) cannot and does not contain medical/health advice. The medical/health information is provided for general informational and educational purposes only and is not a substitute for professional advice. Accordingly, before taking any actions based upon such information, we encourage you to consult with the appropriate professionals. We do not provide any kind of medical/health advice. THE USE OR RELIANCE OF ANY INFORMATION CONTAINED IN THIS CONTENT IS SOLELY AT YOUR OWN RISK. Read our full YouTube Disclaimer at: justincaffrey.com/legals

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A Deep Dive with Justin Caffrey on Happy Pear Podcast

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