DiscoverThe Pocket with Chris Griffin#80: He walked away from 2x million dollar businesses at 24
#80: He walked away from 2x million dollar businesses at 24

#80: He walked away from 2x million dollar businesses at 24

Update: 2025-07-14
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Description

From building two million-dollar businesses in his early twenties to walking away from it all for a life of freedom and meaning, Jai Howitt’s story is all about letting go of what feeds your ego so you can build what truly matters.




Key Discussion Points:



  • How growing up as one of seven kids shaped his drive

  • Building and losing businesses that looked good but felt empty

  • Letting go of ego and the need for validation

  • Designing a life you don’t want to escape from

  • How to fail fast, pivot, and keep moving forward




Follow Jai:


https://www.instagram.com/jai.journeys/




Art Of Mondays - get $500 off your annual membership:


https://www.artofmondays.com/chris




Follow Chris:


https://www.instagram.com/morechrisgriffin/






Timestamps:


00:00 - 04:45 Building million-dollar businesses and burning it all


04:46 - 10:12 The shark story


10:13 - 17:30 Growing up one of seven with something to prove


17:31 - 24:50 Early struggles with validation


24:51 - 32:15 Family road trip


32:16 - 39:40 The warehouse, ego, and identity traps


39:41 - 48:05 Letting go


48:06 - 55:30 Chasing validation


55:31 - 1:07:20 Designing a life you don’t want to escape from


1:07:21 - 1:19:00 Purpose and failing fast

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#80: He walked away from 2x million dollar businesses at 24

#80: He walked away from 2x million dollar businesses at 24

Chris Griffin