In this Business Blast podcast episode, host Tyler Wagner interviews Shelby Osborne, a U.S. Army veteran turned real‑estate investor, broker, and founder of Five Pillars Realty Group. Shelby shares a pivotal 2013 military story where she stepped into a senior HR role as a junior lieutenant, teaching her the power of leverage—using other people’s talents to achieve results. She then explains why real estate is a fast track to early retirement and passive income, and offers broad business counsel: take educated action to avoid analysis paralysis, focus on the 20% of activities that drive 80% of results, and pursue challenges you enjoy as a path to happiness. Shelby highlights the book Miracle Morning Millionaires, emphasizing the importance of systematizing and automating repeatable tasks. Her favorite quote, a Mark Twain line about questioning majority opinion, reflects her contrarian mindset. The episode closes with her online locations (Facebook, Instagram, LinkedIn, BiggerPockets) where listeners can connect with her and Five Pillars Realty Group.
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Alright everyone, welcome back to another episode of the Business Blast podcast. I'm your host Tyler Wagner and today's sponsor is Flipboard. Flipboard curates the world stories so you can be smarter in your work, life, and play. Choose from thousands of topics to personalize Flipboard and get the latest stories from the best publishers and experts delivered to you 24/7. So You can get started now at flipboard.com. And now let's jump into the episode. All right everyone, welcome back to another episode of the Business Blast podcast. I'm your host Tyler Wagner. Today I have Shelby Osborne with us. She is a US Army veteran turned real estate investor and broker. She's the founder of Five Pillars Realty Group and host of Fayetteville's real estate investor meetup, Pints and Properties, as well as the 2018 Keller Williams Fayetteville Rookie of the Year. So welcome to the show.
Thanks, Tyler. Thanks for having me.
Of course. Grateful to have you here. So Shelby, the first question we ask on this show is what is the best story from your life that has an underlying valuable message?
Okay, so I thought about this one for a bit, and I think the best one is back in 2013 when I was almost 23 years old. I was a lieutenant in the Army, so still pretty junior, and I was stationed out at Fort Lewis, Washington, and super motivated, high standards, all that. I was working at brigade level, which for those of you who are unfamiliar with the military, it's pretty high up there for a junior officer, and it wasn't the because I was worthy. They kind of just dump you there as a new lieutenant. You kind of end up where they put you. But regardless, I was working in the personnel management HR section, and the head of HR has 14, 15 years experience, and she had a baby. And so in the couple months of her admin or her absence, like when she was gone, I had to step up and cover her full-time job. My full-time job and then manage an entire section of individuals, which was about 10 people. So as a new lieutenant, this was a lot. And the most valuable message I learned from all of that is the power of leverage, which I still use a lot in my business today and using, capitalizing on other people's talents in order for the entire section to be successful. You don't have to do it all yourself.
Mm-hmm. And then what is the most valuable piece of information we should know that's within your expertise or industry?
Yeah, so real estate is the way to early retirement if you're into that, and can get you a lifetime of passive income paychecks.
Absolutely. Yeah, some of my friends are in real estate and they seem to be doing well. So I've been considering diving in at some point.
So So yeah, you should, you should.
Yeah, no, I think I definitely will. I just, I got my, my hands tied with book publishing and podcasting, you know. Yeah, you're kind of busy. So the next one is, what's your best piece of overall business advice? So not necessarily industry specific, right?
I would say taking educated action. So a lot of people will get that analysis paralysis. And I think that this is business-wide, not just in real estate. But as long as you do your research and your You're educated on a topic, take the action and go for whatever you want.
And then if you could give your younger self one piece of advice, what would that be?
That not everything matters equally. I used to try to do it all, but it really goes back to that 80/20 rule where, you know, roughly 80% of your effects come from 20% of your causes. And so it's really important to focus your energy on that 20% in order to maximize your productivity.
And then kind of going a little bit down a different path, in your opinion, what is the key to happiness?
It would be finding the challenges that you enjoy because life is going to have problems no matter how much money you have, businesses you own, houses, cars, all that. You're going to have problems. So to be happy, you just need to find which ones you enjoy solving.
I have not heard that. I love that. Find the problems you enjoy. That's good stuff right there. All right. All right. Next one is, what is the best book you've read and what's the number one thing you learned from that?
Yeah. Okay. So Miracle Morning Millionaires is my favorite book. It's by Hal— I don't even know how to say it, but Elrod, I think, and David Osborne. And I got so much from that book. I really did. But I think that the biggest takeaway I got was they emphasize systematizing and automating your world and anything you do repeatedly, build the system and then leverage it out. So that way it doesn't continually eat up your time.
And then what is your favorite quote and why?
"Whenever you find yourself on the side of majority, it's time to pause and reflect," by Mark Twain. Because if you're with everyone, you know, it's time to be like, hmm, usually I feel like I'm most productive when I'm going against the grain and kind of going to do my own thing, you know?
Hey, I can relate. That was kind of one of the quotes that made me want to drop out of school, actually, because I was like, I don't think this is for me. And then I went completely the other direction, ended up working out. So I can relate to that.
I love that.
So listen, thank you so much for coming on. The last one we got for you is where can our listeners find you online?
Yeah, for sure. So basically all the social media, Facebook, Instagram, LinkedIn, BiggerPockets for those real estate investors out there. If you search real estate with Shelby Osborne and Five Pillars Realty Group, you're gonna find me.
