051. From Homeless to Helping Through Vulnerability with Jaime Jay

At the core, Jaime Jay is a connector of personalities and brands. He constantly challenges himself to be a better human being. He is also an amateur hockey player and starter good who truly enjoys helping his clients rediscover themselves, their companies and how to realize their “Why.” He has worked with clients across the world, co-founded and run a publishing company, virtual assistant service company, and hosts the popular “Culture Eats Strategy” podcast – a top 100 podcast in the Business category on iTunes. He is the recipient of the Army’s Achievement Medal for Meritorious Service.

Beyond all of that, he is an amazing, humble, giving person. The reason why is rooted in his life story, which started with homelessness, and a rollercoaster experience from there. Jaime shares that story, the lessons he learned and a big piece of himself in this episode of the show.

Key Points from the Episode with Jaime Jay:

  • Embracing vulnerability and being true to yourself helps so much in your personal growth and in business. Jaime goes on to talk about how important it is to be selfish, but in a different way than people may think. He means it positively, in terms of taking care of yourself since you can’t take care of others if you aren’t ok.
  • This sense of needing self-care started in childhood when Jaime dealt with homelessness when his adoptive father moved the family for a job that didn’t materialize. Jaime and his little brother watched an auctioneer selling all of their stuff as they lost everything and lived out of their car for months.
  • He got a job at McDonalds to help support the family, and he would have his family go through the drive-thru so he could give them extra food. He also would take leftover food and give it to his family and other homeless people.
  • Through the homelessness, he struggled to meet requirements at school and had repeat a year and ultimately had to get his GED so he could join the Army.
  • We talked about the timing of this experience given that he was in the midst of his teenage years – a time when most kids struggle with figuring themselves out anyway. Obviously, that only complicated things.
  • Another common issue people deal with after coming back from homelessness is one of the scarcity mindset, which he says has been very much alive in his business decisions. It has impacted him positively around his sense of what being content and ‘having enough’ really means.
  • Jaime shared that his family actually was homeless twice as his father was arrested for embezzlement. It lead him to try very hard not to be a burden on his mother and brother, which is part of why he joined the Army.
  • On top of the issues with his adoptive father, who also made Jaime feel stupid an incapable so much of the time, Jaime’s biological father left when he was five and was a bad drunk.
  • I had to call out the interesting way Jaime has kindness, calmness and gratitude that you might not expect given the tumultuous life he had. He said it stems from his strong desire for no one else to feel what Jaime has felt, so he may go far on the other side of the coin.
  • Jaime shared how his brother got addicted to drugs while Jaime was in the Army. Given how inseparable they were, this hit him hard.
  • He left the Army to be with his wife at the time, with whom he had a child. When he left the Army, he came home to his wife asking for a divorce, leaving him homeless and penniless again.
  • He spent the next decade never really feeling confident or secure, with this unhappiness and fear of what will go wrong.
  • From the age of 21 to 30, he was married and divorced three times.
  • On August 23rd, 2005, his brother was hit by a semi truck and killed when Jaime’s sister-in-law was pregnant with their second child. That devastated Jaime, and threw him into a backward spiral. That day in August is always so hard for him.
  • He started a successful advertising agency in 2006, which was hit hard in 2008 when the economy fell apart. And he was drinking and not saving at that time, which added to everything ending in 2008 with Jaime becoming homeless again, and he had to move back in with his mother at age 38. His perspective at the time was very much one of “The world is doing this to me. Why me?”
  • Sharing his story is tough because he doesn’t feel good about what he did or what happened. He is concerned with what people might think about him. But looking at this through the self-care lens, it helps him tremendously to be open about it, and it serves others through those who identify with his story and find inspiration in it for how they can move forward.
  • Today, he’s been on a different, empowering and gracious path. He’s surrounded himself with the right people who share his positive, kind values, including his girlfriend of seven years, who has been a crucial part of Jaime’s better life.
  • Jaime gave us a challenge. When we feel like someone is a jerk or is behaving badly, look at yourself and your behavior. Did you perhaps provoke that behavior in them? Often, we miss the trigger we are responsible for.


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