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Ep. 70 - Addiction, Sobriety, and Financial Freedom with Josey Orr

In this episode, Josey Orr shares his deeply personal journey from addiction to sobriety, and how that transformation paved the way for a successful business and a rekindled relationship with his high school sweetheart. He offers candid advice on dating, financial freedom, and the power of setting clear intentions.
Josey Orr opens up about his path to sobriety, starting with his mother's own recovery and his genetic predisposition to addiction. He describes hitting a spiritual bottom before finally surrendering in rehab, and emphasizes that the real work begins after getting sober, especially in navigating relationships and emotions. He advocates for radical honesty in dating, advising people to communicate their intentions early to avoid wasting time. Josey also shares the story of reconnecting with his fiancée, Katie, after years apart, and how living with her forced him to grow. On the business side, he discusses his mission-driven CBD brand, Hugs, which donates to addiction treatment. He challenges the zero-sum mindset about money, promotes conscious capitalism, and recommends starting with a goal and working backwards to achieve financial freedom.
00:00
00:00
Making a blind offer on a property in Vashon.
03:28
03:28
Expanders clear the way for something better.
16:32
16:32
Jessica introduces guest Josey Orr, highlighting his dating advice, business growth, and recovery from heroin addiction at a young age.
26:04
26:04
Addiction is a progressive disease.
29:27
29:27
I wasn't ready for sobriety because I hadn't hit a spiritual bottom.
39:37
39:37
He surrendered after realizing he had no other options.
45:47
45:47
Communicate intentions upfront to avoid wasting time.
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52:08
Just ask them directly instead of overthinking.
1:01:45
1:01:45
Personal growth comes from living with an independent partner.
1:07:46
1:07:46
A wedding and a funeral made me realize I wanted to marry her.
1:16:58
1:16:58
Financial freedom is achievable for anyone, even with small savings.