Bob Loudermilk | Tips on Living Your Best Life After 50

Contact Us

Bob Loudermilk | Tips on Living Your Best Life After 50

On this week’s episode of The Over 50 Entrepreneur Podcast, we speak with Bob Loudermilk, Founder of Second Half Events, Inc. 

The entrepreneurial drive grabbed a hold of Bob when he was just 13, leading him to start a neighborhood newspaper that he sold door to door. Bob says, “There was something in me that made me look for what businesses I could start.”

Since that time, Bob’s career has had many twists and turns, but at the heart of it has always been his desire to serve his community and help others succeed which led him to latest venture, Second Half Events, Inc. Second Half Events’ focus is on everything for the 50+ generation. We’ll talk to him about the upcoming Second Half Expo, as well as:

  • The 5 pain points of people 50+
  • The top 2 concerns for those over 50
  • 3 questions to help you find your next step
  • How to leave a lasting legacy
  • And more


Listen now…

Mentioned in this episode:


Voiceover: You’re listening to the Over 50 Entrepreneur, the podcast that’s dedicated to the business builders who are only getting started, when most are winding down. This is the place to discover how to create more freedom from your business while growing the value of your business. Now, here’s your host, Rick Hadrava. 

Rick Hadrava: Hey, guys, this is Rick Hadrava with The Over 50 Entrepreneur podcast. You know, I got to be honest with you, it’s been a while since we’ve, we’ve done an updated podcast, but I felt compelled, in light of what we’ve been through in 2020, the impact to businesses, many businesses out there, and more importantly, to the individuals or families that have been impacted economically, psychologically, medically, all the different ways over the last year and a half or so. And, you know, I think about, we like to spend a lot of our time helping small business owners create more freedom for themselves financially. And, and with time, however, we really are supportive of our entrepreneurial community. 

Because we believe that that is the backbone of our economy. It helps put people to work, it helps take care of families, and so many other things that we need to have a strong community. And I don’t know about a year and a half, two years ago, I met today’s guest, Bob Loudermilk. In he’s doing some amazing things in this space, outside of small business and entrepreneurial, necessarily, but I think as you listen to our conversation today, you’ll find that what the work he does, I think, has many boundaries that he’s overcome, in just trying to be a servant to other people in the community. And so, with that, I want I want to welcome my friend, Bob Loudermilk, to The Over 50 Entrepreneur podcast. Bob, thanks so much for taking the time to be on our on our show.

Bob Loudermilk: Thank you, Rick, it’s so good to be here. I’ve been real excited about your podcast for some time. So I’m glad to come on.

Rick: Well, I appreciate that. Well listen, like I always do with our guests. Let’s go back a little bit so that people can get to know a little bit about Bob Loudermilk, the entrepreneur. What’s your journey been up to this point?

Bob: Well, I don’t know how far back you want to go. But I’ll start at age 13. How does that sound? My first entrepreneurial effort, I actually put together a neighborhood newspaper slash magazine at about age 13. And would sell them door to door and this was back in the days of typewriters. And so I would actually go in and type with carbon paper because we didn’t have copy machines. And if I was such a perfectionist, if I made one mistake, I’d go back and start all over. And so we’d have neighborhood news and some fun stuff and sell them door to door. So that was the beginning of entrepreneurship, entrepreneurship for me. Then, my other compelling desire, which I still continued to this day was in ministry. 

And so at a young age, I went into full time work, church work and so forth, in Wichita, Kansas, and around the age, mid 30s. I tell people that I had to quit for health reasons that everybody got sick of hearing me. But but the truth was, Rick, I there was something in me that I wanted to continue that but I wanted to support myself. And so I began to look for what businesses I could start. And having no training in that actually started a marketing magazine, which was carried on for a couple of years, ended up selling it. And finally, I began an event business, which I own and ran for 19 years in Wichita, Kansas. And we produced events around the country, Rick. We did a lot of job fairs. We did an entrepreneurship conference and so forth, which tied me into a lot of people, job fairs all over the country. 

But I had the opportunity to sell it and didn’t so about six years ago. Moved to Oklahoma, where my wife was from Oklahoma City, with our two daughters. And I’ve lived what we put together because I began to ask what’s next? Too young to retire and my own mind and didn’t have a clue of what to do. I got bored. So I began to research and began to make connections here in Oklahoma City area, tons of connections, we ended up forming something called second half network. And I think you came Rick to a couple of our meetings, right? 

Rick: Yes.

Bob: I recall and Just started meeting all these great people in Oklahoma and Oklahoma City area in particular. And we began to discuss this huge sea of opportunity. And also kind of some scariness, Rick, of people that are above 50 people that as we began to research it and find out what what are your your problems, what are your pain points, we came up with five. And this is not new to you, of course, you’ve researched and lived this for some time. But the pain points of the 50 plus generation that we uncovered is the multiple decisions that people are having to make, sometimes in what’s called the sandwich generation, that they still have kids at home for some people, and then they’ve got aging parents, that they’re dealing with ageism in the workplace, people that are above 50, that can’t find work, because you’re too old, quote, unquote, here’s a big one, insufficient income to retire. 

I know, even at 65, you know, I don’t think I can make it. The other huge one was searching for meaning and purpose. And then the other one, the fifth one was needing the resources and support in order to make it through the 50 plus years. So Rick, we did a couple of forums, you came to one of them. And out of that, we narrowed it down even more, we did surveys in the top two from the people, and these were business leaders and business owners and entrepreneurs and people that work in the second half of life. Companies that serve them, in the top two concerns at our forums came out a sense of purpose, you know, how do I leave a legacy in my life? And the other one was money fears. Can I make it in retirement? So that’s kind of what laid the foundation of what I put together.

Rick: Well, Bob, you know, you and I’ve had conversations in your right, I’ve done a lot of research, and working on a couple projects right now. And the biggest alarming thing to me is we have a generation that will be in their second half of life here. They’re either entering it or they’ll be here soon. And the reality is, there’s very few outcomes for the core of this population to live the same standard of living that that they’ve become accustomed to. And we won’t go into it much but but I think he hit on it. 

And I think more and more people are starting to kind of step back in question that and see that and that that’s why I think the work that you’re doing is really important, because it’s going to take a lot of resources, and community and, and connections to do this. Let’s go back, though, before we move forward. A couple things that you said that were interesting to me. So you decided when you did this newsletter, when gone, really backs up? You said early, you pick marketing. And I’m just curious, you know, your background wasn’t necessarily marketing in, you know, you could have taken it many different directions. Why did you choose to do a newsletter specifically to the marketing community?

Bob: You know, you wonder sometimes are you hardwired to end up doing what you do? Or is that your environment and your upbringing? So I’m not sure exactly where that came. But I’ve always had a marketing mind, you know, from a very young age. And today, I drive my wife crazy, because everything that someone mentioned, my mind says, how can we market that? And I can’t help it, you know, it’s just the way it is. But I think with the magazine that we started in my, in my young 30s, the Wichita Highlighter, where we would go in and we would write stories on businesses, and it was a marketing publication, which was very successful for the businesses. I think it was just a matter of finding a need, you know, that companies needed the ability to tell their story, and to get the word out on what’s the secret sauce of your business and so forth. 

So I think it’s timing to answer your question more specifically. And the opportunity presented itself, that here’s a need, there’s not a publication like this in the Wichita market. So let’s create one, let’s do something. And that’s kind of been a theme that ran through my life that has driven me crazy a few times. Is finding a need getting excited about something having zero background in it, right, we’re going ahead and busting through the wall. Let’s see what’s on the other side of this wall. And it’s a scary way to live. But it’s what drives me and the same thing. When we started the job fairs. I had never heard of the job fair. I’d never been to one. Someone came to me and said we need one in Wichita, and before long we were doing them you know, and so, the marketing side of things, though, has, has ran through everything that I’ve done, from ministry, to the first magazine that we put together and heavily in the events that I’ve done. Helping companies market themselves through trade shows, and through the promotions that we do.

Rick: Well fantastic. And that’s just a testament to the ability to learn, continue to learn, find ways to help others and value always seems to find a way of getting compensated right when you when you bring value to the table. Bob we, you know, I get asked a lot of times are you guys M&A guys? Are, you know, are you broker business brokers? And I always say, no. We like to help businesses that are thinking about transitioning, get as prepared as they can, right. Like, I always say, we want to have you as ready for those conversations as possible. In some of the work we do. And I feel like we’d be missing an opportunity, if we didn’t highlight a little bit about the transaction you had with your business. And it’s always interesting to after the fact to talk to a business owner that sold the business curious, like, anything unexpected, positive, negative, that came out of it, anything you do differently, if you were going through that process over?

Bob: Yes. You know, when I think back on that, again, opportunity, someone said one time, and I love this quote, just one I think about a lot. And that is opportunities rarely come at opportune times. They normally come to continue the quote at the worst times. Times that challenge you. And then what you must do is stop, recognize the opportunity for what it is, and then rearrange some priorities to take full advantage of it. That’s a mouthful. But I’m telling you, Rick, that is a powerful, powerful quote. And I came across it in a book I read years ago. And so when you think about selling a business, sometimes opportunities come at inopportune times, you weren’t really aggressively trying to sell it. 

And an opportunity appears other times for probably for most businesses, you can tell me is probably something that they plan for, and that they have to be ready for. But specifically to your question, I had ran the business for like I mentioned, 19 years, and I began to see a shift. It’s specifically with job fairs. You know, the events were not as large as they had been. So I had to make a decision do I fully invest in the latest technologies and, you know, invest a lot of money into that. Or, as I was meeting with the local newspaper, the Wichita Eagle at the time, it dawned upon me and one of our conversations, and I said, well, how would you like to go ahead and just own the event? 

Because they’d been a major sponsor. And so that led to discussions. And before long, we negotiated a price and I trained their team and they took over. So there wasn’t, for me a lot of preparation for that, other than trying to run a good strong business, you know, trying to keep the financials up. Trying to show growth, but I wasn’t aggressively marketing. It just happened that they came along at the right time. And I was ready.

Rick: Good, good. Well, you know, it’s an interesting conversation, because you weren’t necessarily out there searching. And, you know, just like statistics on the household. from a financial standpoint, one of the things we really are passionate about is helping business owners build something that they can either run forever transition or sell. But the reality is the majority of the small businesses never get to where you have, you know, where they get into a position to be able to sell and be successful at it. And so I was curious, you know, your thoughts on that. If you had to go back and do it again, would you have done anything differently, Bob?

Bob: I just look back and think probably we could have commanded an even higher price, with the with the right kind of preparation. And, you know, with some support and help I negotiated the deal all on my own. So just if I had had someone with expertise that could have helped guide that probably we could have come out even better.

Rick: I understand, understand. Well, on this same theme. I’m curious one of the things we like to ask all our guests, because we we, you know, a lot of the work is around freedom in what we do. And I’m curious like, what what is freedom mean for Bob Loudermilk as an entrepreneur?

Bob: I think freedom for me is just the resources, financial, and especially time to do whatever it is. I I want to do. That, for me is the ultimate freedom. And that’s one of the things that helped drive my decision to start something new, which we’ll talk about, I think in a few minutes. But to have the resources available, and the resources for me are the two things, you know. If you’re strapped financially, and you’re retired, it limits your freedom. I mean, there’s only so many things you can do. 

On the other hand, if you’re bringing in plenty of income, and you’re in a retirement age, traditionally, but you’re, you’re so busy, and you don’t have time to do the things that you dreamed about or you enjoyed. That’s not freedom, in my mind. So the financial resources and the time resources to accomplish what you want. For me, that includes mission trips, and it includes vacations and spending time with family and grandchildren and leaving a good strong legacy when it’s all done.

Rick: Absolutely. We hear that time and time again, Bob. And so I appreciate you sharing that. Well, you talked a little bit about hey, well, you know, let’s let’s talk about the event that you’ve got coming up here in a couple months. And I’m excited about it, because it’s very unique. And I think it’s a huge opportunity for over 50 entrepreneurs, our second half heroes, whatever, you know, we want to talk about. But tell us a little bit about what you’re working on currently. And let’s just kind of share that with our audience.

Bob: Sure. Well, one of the things that that came out of the second half network, these forums and these gatherings that we were doing, and the surveys we were doing is, you know, pulling the community together. Community over competition. And so you’ve got all of these different organizations that serve the 50 plus generation. And it became clear that there was competition, and some of it was healthy. And some of it maybe wasn’t as healthy as it couldn’t be. So this forum and this group that we put together, really appreciated the idea of community over competition. And so out of that, we began to say, a couple of questions, you know, what could we do in this community? And then number two, what should we do? And then the third question is, what will we do? This came out of a book and a man that came to Oklahoma City years ago, back before the they used to call it a string of pearls. He came to Oklahoma City, when Oklahoma City wasn’t doing well. 

The chamber brought him in as a consultant. And they sit down and they asked those three questions. And out of that, Rick, this is probably been 25 years ago came a vision for Oklahoma City. We actually had him at one of our forums, we zoomed him in, and he asked questions to the audience and vice versa. So we got really excited about this whole concept of what could we do? What should we do based upon all of the opportunities that we have? And then what will we do? And those three questions led to putting together an event for Oklahoma City. And that’s the second half Expo. 

And, you know, a lot of planning, a lot of thought went into this. The whole philosophy of we’re faced right now with a huge sea of opportunity with the 50 plus generation. 10,000 baby boomers turning 65 every day in America. So we’ve got a huge sea of opportunity. But we also have what some people have described as a tsunami coming on our economy. You know, Social Security is there right now. But with 10,000, baby boomers turning 65 every single day, it’s going to have an impact. And so we thought, okay, how can we how can we impact this generation and other generations, with things like rich growth, meaning, security, income, wealth, opportunities, mentoring, family, all of these concepts come together in one event, and then what comes out of the event? 

So that led to the formation of second half Expo. And we have our website up now. We have the event scheduled for October 16, at the beautiful cowboy museum here in Oklahoma City. We’re looking at 150 exhibitors, and we’ll have speakers and entertainment and all kinds of fun things taking place. So that that’s the end result after asking, what could we do? What should we do? What will we do? So we drove a stake in the ground. And that stake is an expo, which is an annual event.

Rick: So Bob, that takes place, October 16, 2021. It’s a nine to four kind of an all day deal. And you’re going to have speakers. And I think there’s some health screening that’s going on some entertainment. There’s a bunch of exhibitors that have already signed up. But you’ve got space for that as well. So it’s a great opportunity for our business owners that are listening, that cater to that, that part of the population to maybe reach out to you. How can they do that on the website? How can an exhibitor do that?

Bob: Yeah, that’s probably the best way is go to secondhalfexpo and that word seconds is spelled out There’s a contact form, there’s all the details. It’s an easily navigated website that we put together. And a couple of the sponsors that are going to be a part of this is the Oklahoman newspaper, both in print, but also in all of their social marketing that they did social outlets. And then news channel four KFOR. They’re a big part of it as well. And then we have several of the local magazines that cater to the 50 plus that are sponsoring it. So we’re very pumped about this. There’s really, you know, you mentioned the health screenings and so forth. 

And I wanted to mention that there’s really two segments to this one are what I will call retired seniors. And Rick, there’s tons of needs there, whether people are looking for help for mom, you know, with some dementia, or dad or are they’re looking for retirement centers, or health care centers, or hospitals and so forth, all of that segment of retired seniors. But there’s another group in this that I have a feeling you’re in, in this category, as well as myself and tons of others that are probably listening. And that’s the people that they they’re around 50, they’re in their 60s, some in their 70s. And for them, retirement’s not on the radar, they’re not thinking about retirement right now. 

They’re active, they love what they’re doing. And so we’ve got a whole segment of this is going to be a part of the event rake and that includes things like wealth creation, investments, finding my 50 plus career, starting the business that’s always kind of lingered in the back of my mind, or helping getting my business sold. And I want to transition into something different. Someone said, don’t retire from something, retire to something. And I think that makes all the difference between a limited mindset, a fixed mindset and a growth mindset, you know, if you’re moving towards something, and so we plan to have, you know, a mini 50 plus job fair there and all of these resources, I think you’re even going to show up and speak for us if I remember, right?

Rick: It’s in my calendar. I’m planning on it. Well, you know, it’s funny, you say that, because there is an empowerment element to folks that want to redefine retirement, and maybe don’t want to give up in you know, sometimes that’s for profit entrepreneurs and business owners. Sometimes it’s not for profit, but it’s really the ability to move away from the things you no longer want to do. And figure out how do you delegate that out? or eliminate it from your lives? How do you get to spend the time in those things that really bring you joy, right? Because that’s, to me, that’s the definition of freedom. You’ve got the time and the financials to be able to do that you’re empowered. So sharing that is well loved it. It’s just a wonderful opportunity. The other thing is, I think for the general public that meets those criterias there is no cost if I if I remember right, right for people to attend. And that is huge for those that might be going well, what is this cost me right? So anything you want to just share on that, Bob?

Bob: Yeah, on the website, we have, they can actually RSVP for a free ticket. And it’s just a simple form a name and an email. And that way we keep them we keep in touch with them about the details of the event and what’s coming up. But absolutely free to all of the attendees. We are still looking for sponsors, the people that it makes sense that they want to be a sponsor of the event. The other thing that we’re putting together is we we plan to have 12 ambassadors for the event. This being the first year, these will be the founding ambassadors and so there’s some nice benefits and these will be community leaders and people that want to help us put the event together promote the event there. Social Marketing outlets, and the recognition that will come with that. We have their pictures on our website and several other things that we’ll be doing for our ambassadors. So anyone that’s listening that might want to be considered for that position, we’d love to talk with them as well. 

Rick: Fantastic. Well, listen, this has been great, I appreciate you spending a little time sharing your own journey. And then talking about this upcoming event. Again, it’s October 16. It’s an all day event. It’s it’s at the National Cowboy and Heritage Museum, or what is it cowboy and Western Heritage Museum, they’ve changed the names a few times over the years, but it’s a wonderful venue. And best of all, for attendees, it’s free, we’ll have the link in the show notes that people can have. And, you know, reach out to us if they want to learn more, reach out on the for details. Bob, before I let you go, any any last thoughts that you’d like to share with our audience today?

Bob: This time of life is so important, you know, when you hit your 50s and above, you start reflecting back and you think, how do I want it to end up? You know, where do I want my life to be someone suggested every person should write their own funeral speech. That seems a little eerie to me. But I think the point is well taken. What do I want people to say about me when I’m gone, when I’m no longer here in this life. And we have the opportunity right now at this age, to hit reset, to evaluate our priorities, and where we want to spend our time. And one of the most powerful things that came out of the book I read years ago by Stephen Covey’s Seven Habits of Highly Effective People. 

And it was a life changer for him. And that is that between stimulus and response, there’s a space. And that space is so powerful in that space is the ability to choose. Someone call it the last of human freedoms. And that came from the book Search for Meaning. Right, and you probably read that book. That when they took everything away from him in the Nazi camp, everything was stripped from him. And he realized and recognized the one thing they cannot take away is my freedom to choose. And so I think that’s the exciting part of this time in life, is it really, it doesn’t matter where we’ve come from, or what we’ve done, the first 50 years, were at halftime, and we can choose kind of where we want to go the rest of our life, and if nothing else comes out of this event. 

But that ability for people to recognize, to reevaluate, to think about what they want to do with the rest of their lives, it’s going to be extremely powerful, so that the entire event will be tailored around that theme, honoring our seniors, and recognize helping seniors recognize the power that they have to impact future generations to do the things they always dreamed about. But maybe they didn’t have the resources or the courage or whatever. And so that’s the part and that’s the message that I’d like to leave with your listeners is that you can choose, and you’re not a tree, you can move.

Rick: You can leave. Right now. I’m just Bob, great advice. Guys, if you’re able to attend this event in October, I’m doing a shameless plug. But one thing I’ve known coming out of the pandemic, is your network and your connections are vital, they’re critical to you, to your health to your business, just you never know when doors are gonna open. And I really think this might be one of those events. And the cost is nothing. There’s no obligation here. That’s why I’m comfortable, kind of pushing a little bit on trying to get our listeners out there. So share with your neighbors share with your friends. If you want to learn more, like I said, go to the show notes on this. 

You know, I really appreciate all the listeners, we’ve gotten some great feedback. And that’s important to me. They tell me it’s important for our ratings on iTunes and that but look, if you have a question, email me That’s I want to hear from you. What’s on your mind? What do you think of the show? Who would you like to have on the show? We always appreciate the support, check out our this podcast on iTunes. Also on our website at Until next time, as always remember, we’re only getting started.

Voiceover: The Over 50 Entrepreneur podcast is sponsored by Epic Business Advisory where we help entrepreneurs escape the owner’s trap, build businesses that can succeed without you, allowing you the opportunity to realize more freedom, think bigger and pursue next level goals. Download our freedom formula at And remember, we’re only getting started.

Share this post?