How to Reinvent Yourself—Steve Olsher, America’s Reinvention Expert, Founder/Editor-In-Chief of Podcast Magazine

Have you ever needed to reinvent yourself? Maybe you sold your business and are starting new, or are at a new season in your life?  Or perhaps you’re franchising your business and starting in a new industry.  How do you go through that change and come out confident and strong on the other side?   

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Steve Olsher, is America’s reinvention expert. He is the Founder/Editor-In-Chief of Podcast Magazine, Creator of ClubPod (the largest podcast group on social media), NY Times bestselling author, keynote speaker, Original Founder of, and the host of the top-rated podcast Reinvention Radio.


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Tom DuFore, Big Sky Franchise Team (00:01):

You’ve worked hard to build your business. And now it’s time to grow. Welcome to the Multiply Your Success podcast. I’m your host, Tom DuFore, CEO of Big Sky Franchise Team and a serial entrepreneur. And the purpose of our podcast is to give you a weekly dose of inspiration and education to help you multiply your success. And as we open today, the question is, have you ever needed to reinvent yourself? Maybe you sold your business, or maybe you’re starting a new business, or possibly you’re at a new season in life. If you’re like many of our clients you’ve recently decided to franchise your business, and now you’re reinventing yourself as a franchisor, as opposed to just the entrepreneur, or the business owner of your current business. It’s a new reinvention that you’re going into.

Tom DuFore, Big Sky Franchise Team (00:52):

And how do you go through that change? And how do you come out confident and strong on the other side? Well, our guest today, Steve Olsher, is America’s reinvention expert. He’s the founder and editor in chief of Podcast Magazine, creator of ClubPod, which is the largest podcast on social media. He’s a New York Times’ bestselling author, keynote speaker, original founder of, and host of the top rated podcast, Reinvention Radio. And he’s built and sold many businesses over the years and had to reinvent himself. So it’s a great interview. You’re going to really enjoy it. So let’s go ahead and jump right into it.

Steve Olsher, Podcast Magazine (01:31):

Happy to be here. And I’m Steve Olsher. Right now the claim to fame is I am the founder and editor in chief of Podcast Magazine. We also run ClubPod on Clubhouse. We’ve got other things going on in the world of new media and social audio as well. Past life, I created, got a number of different endeavors from nightclubs to real estate to catalogs and dot-coms and the catalog, I guess, well, the catalog that became the dot-com claim to fame as we built up and sold and sold that to Barry Diller’s IAC in 2019.

Tom DuFore, Big Sky Franchise Team (02:13):

Wow. Wow. You’ve been involved in so many different industries and you, I love this reinvention expert is one of the things that you bring to things as America’s reinvention expert, I should say. So what is it that drew you to that, or inspired you to go that direction and reinventing and helping folks through that process?

Steve Olsher, Podcast Magazine (02:37):

Not intentional by any stretch from the standpoint of, I’ve just been forced over the course of my career to really reinvent my life. And so, like I said, with all the different iterations that I’ve had to go through, or chose to go through, or chose me to go through, whatever, however you think about that stuff. It’s just been a really interesting ride of trials and tribulations and turns and brain damage and success and failure. And as I looked at really what I’ve done at every turn there, it’s truly all about reinvention. And so that’s a phrase that, at least a mentality and something that I’ve been thinking about just in terms of how we all have the ability to reinvent our lives, literally on a dime. Just something I’ve been teaching and going through my own private Idaho with over the years. But in 2009, we launched the podcast Reinvention Radio. So, that’s at least how long it goes back with my teaching about this stuff.

Tom DuFore, Big Sky Franchise Team (03:39):

Wow. That’s amazing. And the fact that you’ve built your Podcast Magazine and so many things that seems to have spun out of starting that original podcast, would you say that’s accurate?

Steve Olsher, Podcast Magazine (03:54):

Yeah, look, obviously like anything else, there are things you can track and things you can’t track, but as you look back on your career, you can see how things line up and how one really works with and compliments the other, and then how other people have been impacted by your work. Those that have reached out directly and those that you see indirectly in terms of what they’re doing. So, yeah, across the board I’d say that it’s just been a really interesting track, both for me personally, and of course, professionally, and then for those I’ve had the opportunity to connect with over the years.

Tom DuFore, Big Sky Franchise Team (04:29):

Sure. Well, I’d love to just get for even just a high level overview for someone who’s maybe thinking of going maybe changing direction, maybe the folks who tune in here tend to be entrepreneurs, and maybe they’re looking to get into a new business. We help companies franchise. So getting into the franchise in their businesses, this new endeavors, and that they’re reinventing through. So is there a step or process that you’ve identified when you work with your clients, or helping people through this that you help guide them through?

Steve Olsher, Podcast Magazine (05:02):

Yeah, so it’s interesting. My grandfather actually started one of the original franchise businesses way back in the early 1940s. He had the idea to have, well, the company was called Foremost Liquor Store. So my family goes way back into the liquor business many, many, many decades. So almost a hundred years. And so they opened up a store called Foremost Liquors back in, the first door was opened in 1939. And by the mid forties, people were already talking to them about opening a Foremost Liquor Store.

Steve Olsher, Podcast Magazine (05:38):

So they started franchising way back then. And what I will tell you is, look, there’s two different types of businesses, two different types of entrepreneurial endeavors, at least in my way of thinking. One is what I would call commodity oriented business. From the standpoint of you see an opportunity, it makes sense to do something. And you decide to build out that business. From the standpoint of, I don’t think anybody wakes up and says, hey, as a kid, I want to make plastic glasses, or whatever it is. These are things that we need. We need forks, we need knives, we need spoons, we need glasses, et cetera.

Steve Olsher, Podcast Magazine (06:18):

I think anybody who wakes up as a kid and just goes, you know what? I really want to make better dishes. But the reality is maybe they figured out when they were older that they could build a decent looking cup. And it was two cents for each of those, and they could sell them for six cents a pop. And before they knew it, they had a pretty good business going, and they were making pretty good money, and that’s okay. We all need these things, you’re not going to get any awards for changing the world necessarily on creating these things, but it’s the engine, it’s the engine of economy that helps our world operate on a daily basis. So you have commodity oriented businesses. And then, of course, you have passion oriented businesses. You’ve got businesses where these are just things that you really love doing. This is something that puts fire in your soul. In my book, What Is Your What? I talk about how your what has chosen you, and it’s not that what you have chosen.

Steve Olsher, Podcast Magazine (07:14):

So maybe this is something that just chose you, and you can’t go to bed at night without thinking about it, and you can’t wake up in the morning without thinking about it. So you build a business around it. And that becomes who you are and what you do. So the point being, as you look at the world of franchising, as you look at the world of entrepreneurship, et cetera, if you can combine the two where you find something that you like to do, where you find something that you’re really good at doing, and you find something that you can make money doing. If you can combine all three of those elements, you really got a win. So in the world of entrepreneurship, or specifically in the world of franchising, if you can franchise out a particular business, or business model, that you really love the industry, and you’re pretty good at it, and you can make money doing it, then that could really be a passion business.

Tom DuFore, Big Sky Franchise Team (08:14):

Yeah. Yeah. Thank you. That’s fantastic. And I’d love to talk a little bit about your book, and What Is Your What? It’s a clever, the title catches my attention, at least, when I hear, What Is Your What? And so I’d love for you to talk about that and some of the inspiration behind it.

Steve Olsher, Podcast Magazine (08:32):

Yeah. So, the inspiration is, as I said, for a long time I’ve been talking about reinvention, from the standpoint of, I’ve always had that question in my life. Why am I here? Why am I one to do something in this world that can have any meaningful, potentially generational, potentially legacy type impact, and what am I going to do with these years that I’ve been given? And obviously these years aren’t to be taken for granted. I have a friend who is a very successful entrepreneur. He’s built up a company with a $2 billion valuation. And I just learned today that he was diagnosed with a brain tumor. And it’s just like, we just never know when this life is going to be taken from us. So how do we get really clear on doing something that truly puts fire in our soul?

Steve Olsher, Podcast Magazine (09:38):

And so the book was really a, it was really a reflection of my own personal struggle of trying to take the Myers-Briggs and the, What Color Is Your Parachute? And all of these different modalities that really left me with more questions than answers. And just saying, there’s got to be an easier way. There’s got to be an easier framework, something that we can absolutely just hang our hats on and find that it fills those three criteria of something we love doing and something that we’re good at, and something that we can make money at. And so that’s when I started thinking about, maybe there’s an easier way to figure out what that is. And so for years I worked on this what ultimately became the, What Is Your What framework. And I will say that, What Is Your What? I have been talking about that long before Simon Sinek talked about your whys, that’s a whole other conversation for another day.

Steve Olsher, Podcast Magazine (10:38):

But ultimately what I figured out is that if you can get clear on what your core gift is, maybe it’s communicating, maybe it’s teaching, maybe it’s enrolling, or protecting, or entertaining, or whatever those different gifts are that we’ve identified. If you can get really clear on what your core gift is, and this is something that lasts throughout your lifetime, it’s in your DNA, it stays with you from the moment you’re born to the moment you die. Get really clear on what your core gift is. Get really clear on the primary vehicle that you will use to share that gift, and get really clear on the people that you are most compelled to serve. Now we can hit the ground running and we can do something that absolutely provides a fulfillment and adds meaning to our lives.

Tom DuFore, Big Sky Franchise Team (11:23):

Yeah. Yeah. And that’s the whole premise, or general premise, I should say, for someone who’s listening in. So for an audience, a target person to maybe go after and read the book would be someone who’s trying to figure this out, or maybe who would be an ideal person to read the book, or go through that?

Steve Olsher, Podcast Magazine (11:46):

Look, at the end of the day, I think everyone should go through the book. I think it’s a good litmus test to really try to figure out where you’re at, and figure out if what you’re doing is in fact what you should be doing. And I’m not saying that if you come up with the answer of, okay, I need to be doing something else, I’m not saying that you have to go ahead and just quit your day job in this moment, but I am saying that you should at least be willing to enter into the transition where you begin moving slowly, like a recipe mixture. It’s like, well, right now a hundred percent of your income is derived from what it is that you’re perhaps not truly compelled to do, and 0% of your income is. There’s a lot of hours in the day, Tom.

Steve Olsher, Podcast Magazine (12:31):

So as we start to look at being able to take just a little bit of those off hours, maybe it’s, we watch a lot of television, we do a lot of streaming, we do a lot of internet stuff. We do a lot of TikToking, all this stuff. So maybe if we just take seven to 9:00 PM every day, and we start digging into bringing our what to fruition, maybe we take Saturdays and Sundays, maybe we take half of Saturday. Maybe we take a couple hours on Sunday, whatever it is, and start putting some pieces in place and getting in motion to bringing your what to fruition after you discover what that is, then that recipe mixture starts to shift. So now maybe you make your first sale. And so 1% of your income is now derived from your what, and 99% from what you’re currently doing. And then 90/10, and then 80/20 and 70/30, and so on and so forth.

Steve Olsher, Podcast Magazine (13:19):

And at some point you’ll figure out, okay, hey, I got enough money coming in. I got enough momentum here where I can actually cut the rope. But the reality is I think everyone should at some point in their lives, take inventory, uses as a litmus test, and really try to figure out, am I really tapping into my core gift? What is the primary vehicle I’m using to share that gift? And then am I actually serving the people that I’m most compelled to serve?

Tom DuFore, Big Sky Franchise Team (13:46):

Yeah. Yeah. That’s a great summary, and a phenomenal advice as well. And you had mentioned one thing early on here as we started the interview about using Clubhouse, and this probably comes up a lot. And it’s still an new medium here speaking. So you seem to have jumped right into it and have a lot of momentum behind it. Would you mind sharing, or talking a little bit about your experience with Clubhouse and how you’re using it, and how maybe others could get into it?

Steve Olsher, Podcast Magazine (14:23):

Yeah. So I started on Clubhouse back in December, of 2020. Right away as somebody who has been in the podcast industry for, well, almost over 12 years now, I just gravitated right towards it, to me, it just felt like a natural extension what I’ve already been doing. So I love the open format. I love the conversations. I love the ability to connect with people, literally anytime, anywhere from across the globe. And I love the fact that there’s a million different conversations going on about a million different subjects. So to me, it just absolutely makes perfect sense for somebody who likes to talk, for somebody who likes to connect with people, and somebody who likes to learn about other people and what they’re doing to consider social audio as a part of their mix.

Steve Olsher, Podcast Magazine (15:08):

So one of the things that we did really early on is we said, you know what? Let’s jump into the world here of clubs, and having thought about it for about half a second, I realized quite quickly that Clubhouse is going to live and die based on the quality of the clubs that they allow creators to create. And so really early on, we created a club called ClubPod, which obviously is about podcasting. And it’s quickly become the largest podcast club, not only on Clubhouse, but on all of social media, in terms of the group and the number of people that we have in that group. It took us about seven months to get to roughly 67,000 members in ClubPod on Clubhouse. And we use it every day to generate visibility, to generate leads, to generate revenue, and certainly to elevate status credibility and authority.

Tom DuFore, Big Sky Franchise Team (16:04):

Yeah. Amazing. And so, as someone who’s maybe just getting into Clubhouse, or just figuring it out, what advice might you give to someone to just, as they’re entering into it, maybe considering starting their own club, or what would you suggest?

Steve Olsher, Podcast Magazine (16:21):

Yeah. So step one obviously is you go in and you start listening, become familiar with the people who are leading conversations, become familiar with the conversations that are going on, become familiar with the clubs that are having these conversations, and just start diving in as an observer. That’s number one. Number two, you want to then go ahead and you want to start participating in some of those conversations. So that means raise your hand, come up on the stage, contribute in a way that adds meaningful value for those in attendance. Don’t think about it in any way, other than just adding value and just sharing your expertise.

Steve Olsher, Podcast Magazine (16:55):

After you get comfortable on stage, and you really could see the format, you can get a sense of how that world works, there’s nuances to every platform, you’ve got to get a sense of how that platform works. Then I would start thinking about opening up your own rooms, and start leading your own conversations and get some data and see how people responding, play with different titles and so on. And then think about opening up your own club. And once you open up your own club, to grow your club, that’s a whole other discussion and perhaps a little too granular for what we’re talking about here.

Tom DuFore, Big Sky Franchise Team (17:27):

Sure, sure. Well, that’s a great overview. Thank you very much for that. And I’d love to, at this point here, Steve, you’ve been sharing so many great pieces of information and insight here. Before every guest goes, we always make sure that we ask them the same four questions to hear what your responses are to our four questions. And the first question is, as you’ve been involved as a serial entrepreneur, starting, growing businesses, doing all kinds of things in your career, has there been a miss or two along the way that stands out and something you learned from it?

Steve Olsher, Podcast Magazine (18:03):

Oh God, so many misses, it’s not even funny. Where do I begin? So the first miss was honestly with One of the things that I should have done was I should have just owned that domain personally and held it and held it and held it. And just even in the acquisition, I should have just kept the domain. And I should’ve done a lease structure with Diller’s IAC and have a buyback in case of things going south or whatever, but I absolutely should never, ever, ever have let go of that domain. That’s a huge mistake. I’ve also made huge mistakes in real estate, when I was doing really, really well, I’ve developed over $50 million in property over the years. I ended up having to give four properties back to the banks over the years.

Steve Olsher, Podcast Magazine (18:45):

And so there were opportunities there that I missed in terms of being able to hold on to those properties and restructure and do things in a different way. So, just between those two things alone, I’d say is easily looking at 20 to $25 million that I’ve left on the table, just with those endeavors. I can keep going, but I’ll stop, because I’ll start crying here at some point. So I’ll just leave it at that.

Tom DuFore, Big Sky Franchise Team (19:12):

Sure. Perfect. Well, look, we’ll flip it, the sunny side up here now and talk about a make or two that maybe stands out along the way and a few you’d like to share.

Steve Olsher, Podcast Magazine (19:23):

Yeah. Look, the biggest make, although there’ve been plenty of those, and this is going to sound corny as hell, but I think the biggest win really is being married to an incredible woman. And we’ve been married since 1997. And so, being married to a strong opinionated woman who won’t let you just settle for anything less than what she believes you can be, or vice versa, obviously if you’re married to a man, and for him to push you to really become what it is that you can become, somebody who can really hold you accountable, keep you honest, and really be there to bounce your ideas off of, and to be that rock, I don’t know this to be true by any stretch of the imagination, but I bet there’s something to be said for the general wellbeing of entrepreneurs that are in healthy relationships. And they stay with that same person in a way where it’s collaborative, not in a way where obviously you grow and then you build this company and then you’re like, F this noise I’m out of here. And you get divorced.

Steve Olsher, Podcast Magazine (20:41):

I’m talking about the people that build and stay together, both the relationship and their businesses. Again, I don’t know this to be true, but I would venture to guess if we were actually to do health studies, I think we would find that those people that are collaborative in nature with their significant other are probably significantly healthier, both from a mental standpoint and probably from a physical and spiritual standpoint as well.

Tom DuFore, Big Sky Franchise Team (21:03):

Yeah. Oh, wow. Yeah. That’s fantastic. And I would tend to agree with you there. I agree. And well, how about a multiplier? The name of the show is Multiply Your Success. So we talk about folks using a multiplier. We get a great diversity of answers here. So I’m curious for you what that has been?

Steve Olsher, Podcast Magazine (21:24):

I would say that the multiplier for me, really more than anything else, has been taking a good, honest, hard look at the skills that I’ve acquired and then leveraging those skills across the different elements of business, and different endeavors that I’ve created over the years. In other words, the real multiplier is understanding what your core gift is, what your core strength is, and really playing to that. And what my core gift is, is enrolling. And so I’m a visionary and I can create, just like Podcast Magazine, or other things that I’ve done over the years. I’m really, really good at coming up with the idea and then enrolling people into that vision, whether that be through raising capital, or bringing on team, or volunteers, or whatever it might be. So the real multiplier, I believe then, is understanding what that core gift is, and then leveraging that through all of your initiatives.

Tom DuFore, Big Sky Franchise Team (22:24):

Yeah, that’s incredible. Well, and thank you for sharing that. And the final question we ask every guest is what does success mean to you?

Steve Olsher, Podcast Magazine (22:34):

Yeah. There’s a lot of great definitions of success. I actually happen to like Thomas [Chin’s 00:22:39] definition and he says that, “Success means having the courage, the determination and the will to become the person you were meant to be.”

Tom DuFore, Big Sky Franchise Team (22:50):

Yeah. Very succinct and well said there. Well, and Steve, as we bring this to a close, is there anything you were hoping to say or share that maybe you didn’t have a chance to?

Steve Olsher, Podcast Magazine (23:01):

No. Look, obviously whether it’s through franchising or through any other entrepreneurial endeavor, and the fact that you’re even thinking about going into business for yourself, or you’re already in business for yourself, it’s a fun track, it’s a scary track, it is a lonely track. And so listening to shows like this, knowing that you’re not alone, huge. Being a part of masterminds and getting involved with other entrepreneurs, and sharing in real meaningful, deep, open, vulnerable ways is super important. And what I will just tell you is that the best thing that you can do is say, I don’t know, and ask for help, because at the end of the day, that’s something that very few entrepreneurs are willing to do, especially aspiring entrepreneurs. And ultimately even those who are successful, there’s always someone who’s going to be another step down the path from you, and asking for help can almost never steer you wrong.

Tom DuFore, Big Sky Franchise Team (24:03):

Yeah. And well, and how can, if someone’s listening in, what’s the best way for them to track down your book, or learn more about you, or get connected to all the different things you’re doing?

Steve Olsher, Podcast Magazine (24:13):

Well, look, we talked about the book, What Is Your What? Discover the one amazing thing you were born to do. So why don’t we just start there? And I would suggest that people go to,, because there, they can grab a free copy of the entire book, or if reading’s not your thing, or maybe you’re more into podcasts, then I’ll give you a private backdoor link to grab a free lifetime subscription to Podcasts Magazine, which is really simple, and then /free. And that’s a private backdoor link I’m happy to share.

Tom DuFore, Big Sky Franchise Team (24:44):

Steve, thank you so much again, for being a guest and sharing your time and wisdom with us. And let’s go ahead and jump into today’s three key takeaways. So takeaway number one is when he talked about taking a good, honest, hard look at your skills and gifts, and focus on using and harnessing those. And if you can get clear on what that core gift is of yours, the vehicle you want to use to go through it and expand with it, and to get clear on the people you will serve with it, you have your recipe for fulfillment. I thought that was awesome. Takeaway number two is when he talked about one of the top makes he had, was finding a great life partner when he married his wife, someone who can hold you accountable and keep you honest. Takeaway number three, the best thing you can do sometimes is just to say, I don’t know, and ask for help. Say, I don’t know, and ask for help.

Tom DuFore, Big Sky Franchise Team (25:47):

And he talked about how very often, especially early on entrepreneurs, or startup entrepreneurs, don’t always ask for help by saying, I don’t know. And it’s really a sign of strength, not weakness. And now it’s time for today’s win-win. So today’s win-win is when Steve gave his definition of success and it’s a quote, or he quoted it from Thomas [Chin 00:26:17] and he says, “Having the courage, the determination and the will to become the person you are meant to be,” I thought that was a beautiful definition. And if you are pursuing that, it’s absolutely going to be a win for you and all of those people you’re impacting and affecting in your life. And so that’s the episode today folks. Please make sure you subscribe to the podcast and give us a review. And remember if you or anyone you know, might be ready to franchise their business, or take their franchise company to the next level, please connect with us at Thanks for tuning in. And we look forward to having you back next week.

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