239 How A U.S. Army Paratrooper Went From Homeless to Successful Entrepreneur with Jaime Jay, Author of Quit Repeating Yourself


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By Christopher Lochhead. Discovered by Player FM and our community — copyright is owned by the publisher, not Player FM, and audio is streamed directly from their servers. Hit the Subscribe button to track updates in Player FM, or paste the feed URL into other podcast apps.
We hear a lot of talk about courage, grit, and being mission-driven. Well, imagine being a young man who decides to serve his country and become a US Army paratrooper, only to become homeless after his active duty. Now imaging finding a way out of complete desperation to become a successful entrepreneur, and now bestselling author. That is Jaime Jay, and he is our guest in this episode of Follow Your Different. Jaime Jay is the co-founder of Bottleneck Distant Assistants, and the author of the new bestselling book, Quit Repeating Yourself. Jaime and I have been working together for years, and he has helped me in most of my digital endeavors. This includes building Lochhead.com, as well as handling all of the technical issues with my podcasts and much more. What you’re about to hear is an inspiring story of how Jaime designed a legendary business and life with his partner, Sara. Pay special attention to how Covid19 almost destroyed Jaime’s business, and how a new category design helped it to come back from the brink and power the company to even greater heights. Jaime Jay in the US Army There is a special place in my heart for our vets, and even more so for those who have become entrepreneurs after serving their duty. So I asked Jaime about his military service. Jaime was part of the elite 82nd Airborne Division, and was trained as a paratrooper. He recalls how intense the training was to be part of such an elite organization, and be battle-ready for when the country needs them. “I was part of the elite 82nd Airborne Division, 2nd 325 Airborne Infantry Regiment and I had a blast. It was is fantastic. I was really proud to be part of that organization. They man, they run a tip top organization. And that was blessed to be be part of the 82nd. That's pretty cool.” - Jaime Jay Jaime Jay on Being Homeless Jaime shares that he has been homeless on two separate times of his life. The first one being related to his younger days, and the latter was after he had left the military. Yet he never let these circumstances weigh him down, and he continued to strive for a better life. He talks about these points in the book as well, not for people to feel bad for him, but to see that despite all of that, you can still persevere and live a good life. “By the way, the reason I tell these stories is not for people to ever feel bad for me or anything like that. But I want people to realize what all of this led to. I'm actually blessed that all this happened because all of this led to a better life where I appreciated so much more. The friendships like the friendship that I have with you, I will forever appreciate this for the rest of my life. I was able to find the woman of my dreams. And I appreciate it on such a different level, just the same way that I appreciate the work that we're doing. So the reason that I tell these stories in here is because I really want people to understand that, hey, it's possible to do whatever it is you're passionate about. So it's kind of motivating, but there's a method to the madness. “ - Jaime Jay Creating a New Category: Distant Assistants One of the things Jaime and I have worked on this past year was when we created a new category that deals with remote assistance. You might say we already have that, and it’s called virtual assistants. Though the problem with virtual assistants nowadays is that the category has been inundated with big corporations who deal more with technology rather than the human aspect of it. While there are merits to automated assistance run by AI and such, there is something to be said for having an actual person handling it for you, and that flexible decision-making that can’t be achieved by AI yet. “People are using a lot of AI and stuff to manage the calendar to send out emails, automation. That's all fine and dandy, and there are some great use cases for that. I'm not here to argue that, but I also think there's something to be said for having that human,

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