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Steve Olsher: The Wild West Internet, Reinventing & Discovering Your What

My guest is a guy that got started selling on CompuServe’s Electronic Mall back in 1993.

His story goes further than that, but that is what catches the eye.

He's also The New York Times bestselling author of What Is Your WHAT?.

He's an international keynote speaker and he is the Chairman and Cofounder of Liquor.com and an all-around great guy.

We shall talk about the Wild Wild West internet days of selling online and building up Liquor.com and losing it.

We’ll also talk about reinvention and how that is critical to the process in a new spin, a new angle on reinvention that you're going to want to know.

We’ll also get into discovering your what, not your why.

We’ll get into that and a whole lot more with the sprinkle of some real estate investing and developing.

With that said, let's get to it.

Dustin
It's 1993, you're hanging out online on good old CompuServe in the Electronic Mall. You get the idea to launch what would become
Steve
We started as a catalog company, which was called Liquor by Wire.
Dustin
Was it like catalog as in direct mail catalog?
Steve
You bet. Liquor by Wire was FTD for wine and champagne spirits. We would get an order that order would then be sent out to a local retailer. The local retailer would deliver that. We took a little margin on that and called it a day. Up until that point, catalog businesses were operating through 1-800 numbers. We used to call it the WATS line way back in the day.
Dustin
Why is it called WATS?
Steve
I have no clue. I am sure there is someone smarter than I am that will tell you why it’s called the WATS line. It was around the time when you would go to the grocery store, you would see the CDs and you have your choice of AOL, Prodigy, CompuServe. I was like, “This is cool.”
Everybody at that point started getting the computer thing going. I didn't know what to do other than maybe create a Word doc or an Excel spreadsheet, whatever. I was like, “This is pretty sweet. Let me check this out.” AOL had a pretty decent headstart but CompuServe was right there with them at that time.
I had a buddy who was doing pretty well on AOL. I thought CompuServe had a pretty good chance of making it happen. I was like, “Let me explore what's going on there at CompuServe and sure enough, they had something called the Electronic Mall.
It was very much in its embryonic stages. These are the days of dial-up modems. To load the picture of a bottle of wine as an example, you would have to sit there for about a minute for the photo to load.
It's 1993, so I'm 24 years old and you're looking online doing these things a 24-year-old kid would do. It got to the point where if I was looking for a picture of a pretty girl, it would start loading line by line. By the time it got to her eyebrows, I knew if I wanted to sit there for the next few minutes and wait to see the rest of whatever that was showing.
This was pretty embryonic stages. We decided to go to Columbus, Ohio, which is where CompuServe was based and go through the whole training of launching a store on their Electronic Mall for our business, which at that time was called Liquor by Wire.
Dustin
This wasn't risky to you because you had a buddy that was doing this on AOL because I'd be thinking double down on direct mail or whatever the old school method was. Was there anything else there that you recognized that online is the future?
Steve
It was one of those things where you go back to the old Gretzky term, “Where's the puck going?” To me, it was clear as day that whatever number of users they had at that moment, it was going to continue to grow. There was no other choice. We did fairly well on CompuServe Electronic Mall and launched a fully functional eCommerce site in ‘95.
Dustin
You weren't taking orders online yet. Weren't you driving them to the phone from online?
Steve
No, we were taking those. At that point, because it was CompuServe Electronic Mall, there was a commerce platform built into their platform. We could take orders from people, put in their credit card numbers and the whole nine. Once we got those orders, then we manually had to input all the orders.
Dustin
People were pretty bold. I know a lot of people for a long time were skeptical about putting credit cards in, but these were early adopters in that and you were making a mint from this.
Steve
At that point, it wasn't even done where we had any online interface even to process the orders. We would go to a desk where the terminal sat on the desk and we would punch in the numbers, “Is credit card present? No,” and punch in all the numbers and the expiration date.
They didn't care about the CVV code, whatever it is. They didn't care about any of that. It’s, “Is a card present?” “No.” “What's the card number and the expiration date?” We'd run it straight from there. We were probably paying 5% as a processing fee or something like that. It was pretty pricey.
Dustin
There’s no regulation at this point. You said you were sending the orders to retail, so you weren't necessarily selling a bottle of alcohol and shipping it.
Steve
Technically, we were a marketing agency. We had to sue the State of Illinois. We're based in Illinois at that point. I lived in Chicago for the first many years of my life before I got smart and moved to San Diego. I have nothing against Chicago. I love Chicago but I loved the weather here better.
We ended up having to sue the state of Illinois because they tried classifying us as a liquor retailer. We ended up winning that argument. It costs us way too much money, but we physically never took possession of the product. All we were was a marketing agency. Our local retailers handled all those deliveries.
Dustin
Was the model to sell it first and then call up somebody in that state, a distributor or a company selling on the ground and saying, “We got an order, can you fulfill it?”
Steve
That's how it went. For a period of time, we were somewhat the largest retailers’ largest customers because that's exactly how we did it. Anything that we put an order through for, there would already be payment on.
There was a period of time where we were in the top ten by volume of all companies because we weren't a liquor store, but liquor stores would be in that list there including clubs and restaurants and so on. There was a point in time where we were in the top ten on that list. I say this only from the standpoint that we didn't technically make a list because we weren't licensed, but I knew where the numbers were.
We were selling more Dom Pérignon than almost everyone else in the country there. There were a handful of people that were moving more Dom than we were.
Dustin
Can you do this model now?
Steve
For sure, I have no interest in selling booze.
Dustin
Not you but in general, a lot of people may say, “That guy was first to market and that doesn't work now.”
Steve
There are companies that are doing that now. Interestingly enough, Amazon has a retailer in LA, a very small retail shop that they're only using the license to be able to ship from that location. They also opened one in San Francisco.
Dustin
It's a matter of time, right?
Steve
Yeah, they’re in that game.
Dustin
How do you feel about that? I know that's not where you're active and spend most of your time, but what do you see coming?
Steve
I am still involved with Liquor.com on the board level. I’m one of the larger shareholders still. I don't have any active day-to-day with it. There is no winner when there's a race to the bottom. If you're competing on price and you're in a commodity-oriented business, you lose.
Who do you lose to? Amazon, all day long. If Amazon wants to destroy you, they will destroy you. Anytime you're selling a commodity or a product that has a face, a name, a brand and a price, you’ll lose if they want to get into that game.
Dustin
Is
Steve
I hope that we exit and we're talking to a couple of companies now. We've been fighting the fight now for about a decade. There are a lot of good things going on there, don't get me wrong.
The management team that I put in place are doing some good things. We don't sell a single bottle of booze. As a matter of fact, we don't sell anything much to my chagrin. This is an argument I've been having with the management team.
Dustin
What do you mean by that? Is it just ads?
Steve
We don't sell anything, nothing, zero. You cannot put a credit card. You can't even buy a glass on Liquor.com.
Dustin
What's the purpose of that?
Steve
I have no idea. You go there for recipes and information. Four million people have signed up for the database. I don't even know how many are active at this point. Three million to four million people come month after month to the site. The traffic is there. We’re number one, number two in SEO in almost every category and we don't sell a thing.
Dustin
I want to take it back. Let's talk about your exit from day-to-day. You mentioned you are still a big shareholder but you're not actively running it. How did you get to that point to decide you were going to move on? What advice do you have for others to not get trapped? That was me in my previous thing.
Steve
It's an interesting story and there's a lot of hair in this deal for me. If you go back far enough 1991, I should preface all of this by saying that Liquor by Wire was originally a very small piece of our family business. My grandfather started Foremost Liquor stores in Chicago back in 1939. My family was in the business already.
I had opened up my own nightclub. I had DJ’ed for years. I had done all that fun stuff. When that burnt out a little bit and I was ready for something next, my mom who was actively running the company since ‘77 said, “Why don't you come in and figure out if there's something you can do here with the business?”
It’s very near and dear to my heart and liquor by far was a small piece of that puzzle. If we were doing an order a day when I came on board, it would have been a lot. It didn't become Liquor.com until we bought that domain in ‘98. It was a stretch at that point. We bought Liquor.com and Bourbon.com for $7,500 back in ‘98. That was a great deal in hindsight but at the time I was like, “This is a stretch.”
Dustin
How did you sell the idea of, “Let's jump into this?”
Steve
Grandpa died in ‘94. It was just mom and me at that point. This was a once in a lifetime opportunity to grab a category killer domain in that space. We had been doing pretty well and dot-com hype was starting to take hold. In my mind, I had the vision of let's take this thing public because you remember crazy days of ‘98 to ‘99.
The ideas on a napkin were being funded like people slide napkins across the table going, “Fund this,” and they get funded. By the time ‘98-ish came around or so, there was already enough momentum there in the space. I was like, “Let's grab this.” It was a stretch. That's $2.5 million now.
Dustin
$7,500 is $2.5 million now?
Steve
Something like that, whatever that translates to. Even back then, it was still a lot of money, especially for a small business. I thought there was a good opportunity there. I'm like, “Let's go out on a limb and try to do what we can do here.” Sure enough, it helped tremendously. We ended up ramping to about $3.5 million in annual sales by the time ‘99 came around.
The domain helped. Not like you would imagine. It wasn't like a million people decided to show up on-site, but it helped. We've got a great domain. All of the heavy lifting is done. We've got the infrastructure in place. We need marketing dollars. “Let's raise some money. Let's try to bring in some marketing dollars. Let people know we exist.”
We had the S-1 filed in March of 2000. In March of 2000, NASDAQ was at 5,500 and then everything tanked. We couldn't get out. Like an idiot, signed away management rights to the company because Wall Street wanted to see the CEO, the CFO, the CTO, the WTFs and all these lettered saviors. We signed away management rights being completely blinded by dot-com light.
We couldn't get out and it was pretty much the downfall from that point forward, so much so that I left the company in August of 2000. That would be a few months after we were scheduled to go public. I couldn't get along with the CEO and the whole nine. The rule was, “Don't sign away your management rights.” Don't give away your baby.
That’s a takeaway, write that one down. What was interesting though is the domain was in my name. I didn't lease it to the company. I didn't sell it to the company, but it was in my name. I had registered the domain but I quit, walked away and for a few years it was out of sight, out of mind. I never gave it a second thought.
I was walking the dogs in 2005, 2006, whatever that year was. I was carrying The Wall Street Journal. Back in the day, there used to be something called a newspaper. I was walking the dogs carrying this newspaper and the headline read something to the extent of, “Domain name prices breaching pre-bubble burst values,” or something like that.
I was like, “Whatever happened to that Liquor.com domain?” I didn't know. It was out of sight, out of mind. I tracked it down to a guy in the country of Panama. We went back and forth for a long time in how did he get the domain, lots of questions. I didn't threaten legal action but it was pretty clear that he came across it perhaps in some shady way.
It was almost Christmas Eve of 2006. I get an email from the guy and he's like, “I've given this some thought and I want to give back your domain.” I was like, “Sure enough but I had no idea how to do that.” He's like, “Go here, open an account, send me this code and I'll transfer it.” I'm like, “That sounds shady but fine.”
I've got nothing to lose. I was going to get my name and address. I do that and sure enough, he transferred the domain and I had given him my password because I didn't even know what to do. I'm like, “Go in and do whatever you’ve got to do.” I put it in, went in and the domain is there. I change the password and immediately put it up for sale. It ended up with a number of offers on it.
Dustin
Would it have been weird for you to go back to the company that you were no longer part of, but have a share and say, “I want to lease this to you?”
Steve
That company didn't exist. It disappeared. It fell off the face of the Earth. The Liquor.com did not exist. I put it up for sale. It ended up with a number of different offers. The top offer was $4.25 million. Needless to say, I accepted it.
The guy made the first few payments and then bailed on the rest. Contractually, I was able to keep the money and keep the domain. I was pretty burnt by that point. Here I am, I've got this great domain but I don't want to be running this company.
If you're familiar with TechCrunch, back in the day, it had an event called TechCrunch 40 I think originally, where they would feature 40 companies. People would have an opportunity to see what they were doing and potentially invest in them. They had something called a demo pit, which is where other companies could display what it was that they were doing.
Hopefully, some investors would walk by and be like, “I love what you're doing. Let me throw some money at you.” We ended up in the demo pit of that TechCrunch event and there were a couple of guys who were running a small boutique consulting firm.
I knew if I was going to do this again, it would need to be with people out of San Francisco and Silicon Valley because it's such a Silicon Valley phenomenon, this whole dot-com world.
The agreement was we'd partner with these two guys and we'd have a 50/50 split. Those guys would build the company and we'd get 50% for contributing the domain. We, meaning I brought in one very minority partner to help a little bit with some of the collateral and some other things.
That's how it worked out. We brought them in. The deal was I'd be chairman, which is just a BS figurehead, meaning nothing of any sort, at least after the first period of time there.
Once again, I ended up clashing with people that I brought in. Imagine that, I am the common denominator. That was the deal. They would build the company. I would contribute the domain and that's where it's been to this day.
They have done a lot of things well. They just have not moved into commerce and I think that's left a lot of money, whether it's a membership program or selling a t-shirt. They don't even sell booze, sell the fork and something, anything.
Dustin
I'm waiting for when you get the knock at the door as I've seen in all the Steve Jobs movies where it's like, “We kicked you out of Apple, but now we want you back.”
Steve
I've tried but they don't want me because I'm a bull in a China shop. I will be the first to admit that. My ideas might be great, but my presentation sucks. I don't hear the great ideas through the shitty presentation.
Dustin
I was trying to go to
I want to ask you though. I've been to sites of other alcohol, Budweiser or whatever you insert your favorite drink of choice. They have the little date thing on there. It's ridiculous. Why did they do that? We're getting litigious and whatnot.
Steve
We have relationships with the biggest brands in the world. That is one of the things that our CEO and the team has done well.
Dustin
Not just yours, I’m saying all alcohol sites in general. Was this a speed bump in your industry in terms of when that was mandated that you ought to do that for all the sites?
Steve
I don't know what the current rules and regulations are. We had a news crew from Philadelphia show up at our office with cameras running. How could you sell a bottle of booze to a twelve-year-old? They did some BS thing where they went on all these sites and they had a twelve-year-old order with their mother's credit card or whatever it was. A lot of that stemmed from those concerns and fears and whatnot.
Dustin
You were the phenomena before the Alexa phenomenon where kids were ordering. Do you remember that?
Steve
You live and learn. Hopefully, the final chapter will be written in a way that is positive. At the same token, it's business and things can change on a dime. We could end up with a nine-figure offer on this thing and I will buy dinner next time.
It's also the nature of the beast where if all the brands pulled out and all the ads went away and everything, does the company survive without anybody supporting it? No, in any business, you need customers. What happens if all the customers go away? Hopefully, that will never happen. The point is that the final chapter is yet to be written.
Dustin
I want to move us into real estate because we're an investing show here at the Get WealthFit Show. You got real estate in your background. I'm curious as to the deal that started at all. How did you get into it?
Steve
I started officially doing real estate development in ‘98. That was my first purchase of a piece of real estate where I was like, “This is pretty cool.” It wasn't until the Liquor.com stuff blew up. The next big thing was real estate after that. I was like, “There's an opportunity here. We might be able to get to that.”
The first real estate deal that I did was when my wife and I were looking for our own home. The idea was let's see if we can buy a multi-unit building and live in one of the units, have enough rental income being generated so that we can keep our costs down and maybe even make some money.
That was the first deal that I did. It was a four-unit building on the northwest side of Chicago. It was one of these huge A-frame buildings that had four units, a garden unit, first floor, second floor, attic, third-floor unit and there was a four-car garage in the back that was rented out to one guy as well.
When we bought it, we were able to occupy about 1,400-square-feet, three-bedroom and one-bath unit on the second floor. There was enough rental income being generated from the garden unit, the first floor, the attic unit, and the four-car garage. We were making $700 to $900 every single month.
Dustin
What about the headaches though? What are the crazy stories?
Steve
It's funny. I talked to a friend of mine who was in real estate as more of a broker, but he also had a two-unit building. He and his family lived in a duplex and they rented out one of the units in the building.
I asked him, “What is it like being a landlord? I want to do that. It's got to be a pain in the butt. You get toilet issues. You get refrigerator issues and all that stuff.”
He's like, “Honestly, the number of calls that you get are so few. I wouldn't even worry about it.” I was hesitant to be a landlord for sure. Sure enough, there are always going to be an issue two or three there but nothing crazy.
Dustin
We're doing the same thing, my wife and I. You know the story. We moved and we've got that going on. It's a little more interesting when you're not there on site. Nonetheless, It's a wise thing. It's interesting that you got started with that. You're developing big projects. You mentioned a big project that you had developed in Chicago. Do you care to share on that?
Steve
In March of 2000, we filed the S-1 and we want to go public. The whole thing implodes and I walked away from the company. At that same time, real estate was blowing up. I didn't put any money away. For a few years, 1991 to 2000, Liquor.com, I didn't put any money away.
Everything went back into the business. I had nothing but the house. I come home and I'm sitting on the front porch and I think I don't have a lot of time to wallow in this. I’ve got to figure out what to do with a quickness because we got a kid, I’ve got to take care of the house and the whole nine.
Fortunately, our overhead was very minimal because we had money coming in every month. I knew I had to do something. I remember it was about maybe a week or so before that when I was in a gas station. This was before they started doing the credit card swipes at all the pumps in the gas station.
I'm waiting in line to put down my credit card to fill up on one of the pumps there. The Indian clerk is talking to one of his Indian buddies and one guy says to the other, “I bought this condo. I had it for about a month. I flipped it. I made $50,000 on it. This is something you got to do brother.”
I'm overhearing this conversation and I don't consider myself to be the smartest guy in the whole wide world as evidenced by a lot of the stories that I've already told. I consider myself to be smart enough, “If you can do this, I can do this.” I was like, “Let me look more into doing development here and let me see what can be done.”
What I ended up doing was at the time, there were a lot of apartment buildings that people were converting into condominiums. That was the big thing in that. I started looking around and I found a seven-unit apartment building on the northwest side of Chicago not terribly far from where we lived.
The idea was I'm going to convert these units into condominiums. We'll sell them, we'll make a lot of money and everybody will be happy. I had no clue how to do that. I knew I needed a loan so I was going to have to figure out how to do an acquisition and construction loan and I needed money.
How am I going to do this? I have never done any development, don't have a plan, never seen a plan, never written out of proforma and I need to raise money around this. Needless to say, I had to dig pretty deep. I tried to be as resourceful as I possibly could.
I ended up writing a pretty crappy plan and a pretty crappy proforma. It wasn't until after I did my first deal that I realized by seeing someone else's proforma that you could write in a line item for a developer's fee. There's an idea and you can get paid throughout the whole development process.
I ended up raising some money. I don't remember how much we raised. It might have been about $500,000 or whatever it was at that point. There were some pretty aggressive deals like maybe you had to put down 15%, might have been 20% something like that. I bought it, rehabbed it and I kid you not, the day before our model unit was set to open, 9/11 hit.
People got a lot more cautious. Fortunately, it wasn't a long downturn. We were able to sell out. When all was said and done, I ended up making about $125,000 on it. It's a lot of work for $125,000 at least in this world now if you're a real estate flipper and developer.
That was the start I went on and I did about $50 million in real estate development. 2008 to 2009 got hit hard and I had lost three good properties. I had lost a 50,000-square-feet office building that was a herder. I lost a phenomenal corner location mixed-use building like main in Chicago.
Dustin
Is this like hand keys back to the bank?
Steve
Yeah, and then I went through hell on another one because after I moved to San Diego, we were trying to negotiate with the bank. I thought my attorney back home was still negotiating with the bank to try to come to a resolution. It turns out he wasn't even showing up in court.
The bank ended up suing me. No one showed up and I ended up taking a non-recourse loan becoming recourse fully. I was in the middle of a big online project, a big product launch. I woke up one day I got a call from my partner who was like, “The wire that we had sent out to one of our vendors got returned.”
This was like an anomaly. It didn't make any sense to me. It turns out that because my attorney in Chicago had done nothing in so far as representing me in this issue and trying to resolve this with the lender, they’ve got the personal judgment against me.
That took a non-recourse loan turning into full recourse and then they were able to get a full monetary judgment against me personally. I had no representation. Because of that, they were able to enforce that judgment against me here in California. They hired a receiver to freeze all of my assets and put all of my bank accounts on lockdown.
Dustin
That's a lot of work to nail you.
Steve
They thought we were trying to screw them because they thought I was disappearing. I was trying to screw him somehow. That's a story for another day. Long story short on that one, that was a herder because that was one of my favorite buildings. I still have some holdings and we'll be getting into some development here in San Diego again with a lot of lessons learned. I guess if you don't live, you don't have stories to tell.
Dustin
That's why we exist and you exist in the realms that you exist is to educate people and to share the story and then provide education in the ways that you and I do that. Despite all of that, I don't want people to be scared, you're still investing in real estate. You still have holdings.
We're having a conversation, which I think is relevant to put in here. We talked about unfortunately people die, but it's a thing. There's a whole business around that and that's a conversation for another show. The other thing that's an evergreen category is real estate.
People have to live somewhere. Whether people want to have the American dream, the white picket fence or the new crew coming out, the Millennials and whatever they're called now, you’ve got to have shelter over your head.
Despite all those crazy things that happen, you're a big proponent of real estate. The idea is not to get scared here but to educate, pick up a couple of stories and maybe prevent yourself from a few stories. Steve, let's get into reinvention. I've come to embrace this word as I've gotten older.
It seems inevitable before when I was a younger buck. It was like, “That's a cool word.” I didn't understand what it meant. You've already shared some stories that make it seem obvious in terms of your reinvention. You are known as the world's foremost reinvention expert. Why?
Steve
I'm a poster child for reinvention. If you think about all the lives I've had, I should be dead. I've had near-death experiences more than I cared to admit.
Dustin
Was it like disease dead or jumping off cliffs, extreme sports, putting yourself in the face of death or both?
Steve
Three bad car accidents and because the insurance company was being a pain, let's rebuild this thing from the frame up accidents. That was an interesting, $28,000 brand new Chevy Blazer. They’ve spent $24,500 rebuilding. That's an interesting decision right there.
At every junction there you're like, “I better wake up and smell the roses and do something different with my life.” It’s like a wake-up call there. What I've come to realize is reinvention has nothing to do with changing anything about who you are. I believe that it is truly about getting back to the core or to the essence of who you were naturally born to be and how you're naturally wired to excel.
The more we shed the shackles of those personalities, those outfits, those expectations that the world has of us, then we have an opportunity to get back to the essence of who we truly are.
We make a lot of distasteful sacrifices over the years, some conscious choices, most unconscious. That whole realm of reinvention to me boils down to let's take a closer look at who we are. Are we in alignment with how we're naturally wired to excel and what puts fire in our soul?
Dustin
That lands in about a few years I've shared it on the show, putting everything into a prior company in and not going the way that I want to do. You're right along the way. At least for me, I went down this path and made sacrifices and made decisions that weren't who I am.
I love your definition of that. I'd never heard this before. Getting back to who you are because I feel I'm more of who I am meant to be here at WealthFit and doing that. I'm curious, I know you're big on reinvention. Are there any people in society that don't need reinvention or where this doesn't apply? I know you teach a great deal on this.
Steve
I taught a live workshop called The Reinvention Workshop for years. Ostensibly, what I taught at The Reinvention Workshop was reflective of what I created in terms of the, “What is your what?” framework that's featured and shared in that book, What Is Your WHAT?
What I know in terms of the people that I've worked with is that there are some people who have a solid sense of how you would answer all three questions. When you think about the What Is Your What? framework, it's a little bit like a tripod.
There are three core elements of the What Is Your What? framework. They very much work hand-in-hand. The first piece of that puzzle is understanding what your core gift is and having clarity around that. That could be a gift of communication, teaching, healing, entertaining, enrolling, protecting or whatever that core gift might be.
The second piece of the What Is Your What? framework understands the primary vehicle that you will use to then share that gift with the world. The third piece of the puzzle are the people and having clarity around the people that you're most compelled to serve.
What I have found is that there are very few people who have clarity around what their core gift is, what the primary vehicle is it that they will use to share that gift and who the people are that they are most compelled to serve.
If you are able to answer those three questions, then I would say you're probably not in need of any reinvention. If you are unclear as 99.9% of the population is on the answers to one of those questions, let alone all three, then probably reinvention is afoot.
Dustin
I'm going to have fun with you here. I'm a truck driver in Wichita. I don't know why that just came in my head. I'm here in this show. I don't know that my core gift is delivering trash. How do I find what that is?
Maybe I've had this career because it was the only thing I could get. Maybe I've been doing it for a few years out of school. How do I tap into that gift? I know this a crazy scenario but how do I find my gift?
Steve
It's a completely legit scenario. I think Amazon finally removed it, but there was an interesting thread that went along with the book, What Is Your WHAT? The headline of that original thread was, “Who will take out the garbage?”
The point for this person was like, “It's all well and good. Everyone should be happy and everyone should be doing exactly what they want to be doing. Everyone should be making all of this money doing what puts fire in their soul. If that was the case, then who would take out the garbage?”
I think what has to come before that question is, “Is that person unhappy? Does that person even need to be reinvented or to reinvent their own life?”
There are plenty of people who are perfectly content going and doing whatever that 9 to 5 is. Punching out, going home, doing whatever that hobby is, spending time with their family, getting that paycheck, getting that pension, having Social Security, whatever it is and they're perfectly content.
If you ask those people if they needed reinvention, the answer would be, “No, we're fine.” At the same token, it's like a light switch. The light switch is on or the light switch is off.
If the light switch is on where you've gone from off to on and you've become very clear that, “I'm not happy, I'm not thrilled, I don't love what I'm doing, it doesn't put fire in my soul,” then you've got to start looking at the answers to these questions. Once that light switches on and you're like, “I want to discover what my what is, I want to figure out my gift, my vehicle, my people,” it's hard to turn off after that.
Dustin
I love that analogy of the light switch on or off. It reminds me of another one. You're either pregnant or you're not. There's no in-between. I'm with you. I want to ask you this as a little side tangent here. I find interesting people that have other passions. I don't know, I love this game. I think you're of that cloth. You love entrepreneurship. You love building. The 9 to 5 doesn't apply here.
Steve
There are a lot of people who feel that way. The entrepreneurs are like, “Maybe I just go get a government job.”
Dustin
Are people bred this way? In your experience, is it environment? Is it a learned thing to be a 9 to 5 or using that moniker if you will here?
Steve
First of all, we can look at the educational system. The educational system itself breeds 9 to 5ers. They want you in the system to attain a skill that gives you the opportunity to get a job. There's nothing wrong with that. You're ultimately not going to be an entrepreneur if you're going to take that skill.
There are exceptions to that rule, but for the most part, you're going to take that skill. You’re going to go out into the workplace and you are going to get a job. Frankly, we're now starting to see conversations around the dinner table where dad doesn't have a 9 to 5. That's a fairly new phenomenon for dad or mom not to have a 9 to 5.
You can look at some of the communities out there. I'm good friend with Russell Brunson over the years and you can look, for example, that ClickFunnels community. That whole idea of being able to not work 9 to 5 and have an online world that you sell products or programs or services from.
That is reflective of how technology has evolved. As technology has evolved and even podcasting, from this standpoint of I liken podcasting to being the new broadcasting. If you think about radio, it only can reach people within the realm of that signal. Podcasting can reach anyone anywhere in the world at any time. This is a fairly new phenomenon. That's why you see people making a living with podcasts.
That couldn't even happen unless you were syndicated or unless you had a huge audience locally. It’s hard to make a living in radio as an example. The point being, technology has evolved to the point where you with a computer can make a phenomenal living.
Therefore, now you can have a conversation with your children and say, “This is what mommy does, this is what daddy does, this is how you can avoid having to be at the same place every day doing the same things.”
At the same token, they may look at you and go, “I like the idea of being in an office because I like people, dad. I know you hate people. I like people and I want to be around other people.” I think that part of what we see here is that evolution.
Dustin
It was tricky for me to ask you that question. It wasn't as clear to define it, but you helped me define it. I came up in my head that with 9 to 5ers are content doing their thing and then going and doing something else.
Whereas I love the game and don't get me wrong, I love my family but I discovered in this question. I said that entrepreneurs want something more and it's more in a different way. That's what I equated it to.
Steve
At the same token, if you look historically at some of these privately held and even publicly traded companies, you've got people who are doing pretty well going in and not being the entrepreneur. You can look at the number of millionaires that have been made working for Microsoft.
You can look at the number of deca-millionaires that have been made working for Apple, the centi-millionaires being made working for Amazon. There’s a lot to be said for helping to bring an entrepreneur's vision to fruition. Everyone has a role.
Frankly, there are plenty of businesses where the employees financially are doing better than the founder. It's to each his own and even walking around here and seeing this whole operation. I had 30-plus employees and I had the payroll in ‘09 and there's a lot of pressure that goes hand in hand with that.
Not everyone wants those pressures, “Pay me and in this day and age, give me some shares, give me some equity and let's roll this dice together and see what happens.”
Dustin
I want to go back a little bit on What Is Your WHAT? That is your New York Times bestselling book. I wanted to ask you, why is it such a big thing? At least it was at the moment in time, your advocate is “What,” more important or is “Why,” more important?
Steve
They're both super important. We had Simon Sinek on Reinvention Radio, which is one of the podcasts that I do. That was interesting because we had that whole conversation with the why versus the what. He'll tell you it simply it’s semantics issue.
To me, I believe that the biggest differentiator between the two is that your why is something that you choose. It's something that is external. It's something where you do this for your family or you do this because you want to help starving children in Africa. You want to provide clean drinking water for people in third world countries, whatever it is.
It's something external. It's something that you choose. Whereas if you look at the cover of What Is Your WHAT?, you'll see that the only graphic element we have on there is a DNA strand. Why? Because to me, your what is internal. It is already in your DNA. In my way of thinking, your what has chosen you. It's not that what you have chosen. You can choose your why, but you can't choose your what.
Dustin
Does this transform as you reinvent yourself?
Steve
Here's what ends up happening. If you go back to the What Is Your What? framework that it gives the vehicle and the people, your gift is set. You're an entertainer, you’re an enroller, you're a healer, you're a teacher, you're a communicator, whatever that gift is set throughout your life.
You may have a couple of gifts and that sort of thing. Maybe one is 60% and one is 40% but there is always going to be one that's slightly dominant over the other. As things happen in your life, Brendon Burchard talks about how only two things happen in our lives.
Either there are new things come into our lives like maybe someone dies or maybe something happens to you or something of that nature or something new comes out of you. As these new things happen, the vehicle that you may choose to share that gift can evolve. The people you're most compelled to serve, that can change.
What I like to say is that your gift is static. That is always going to be the same throughout your life, but the vehicle and the people are more flexible. Those can evolve over time. Either as new things come into your life or something new comes out of you.
Dustin
What is your what?
Steve
It's an interesting question and it's a cop-out answer. At my core, I am a teacher and second to that, I'd say communication is a second gift. The cop-out here is that my what is helping people discover, share and monetize theirs.
Because of the entrepreneurial experience that I've had and because I consider myself to be a fairly decent marketer, not an exceptional marketer, I can help people share and I can help people monetize their what.
Unlike a lot of people who have the skill and being able to help people share, let's just call it marketing and monetize. I also have the framework of helping them discover it. In author land, they say you write the book that you most need. This is the book that I needed.
Dustin
Cop out, I could see how the masses or naysayers or whatever you want to call it, could see it. I think it takes a special gift or a special talent to be able to piece that all together. Marketers that are great at marketing sometimes are not the best teachers in the world.
Steve
One of the reasons why I wrote the book is because I knew there had to be an easier way. I did the Myers-Briggs. I did the What Color is Your Parachute? It’s like, “What color is your parachute? Okay, great.” There are four conversations in the room. It's like this room, they were talking about business. This room, maybe they're talking about sports.
All I'm thinking is like, “Where's the door? Get me out of this room.” All of that exercise stuff or whatever, it's all well and good, but none of it provided a practical, “Let's hit the ground running. Let's do something tomorrow with this information,” type of approach.
Once you're clear on what your gift is, once you're clear on the vehicle that you use to share that gift, you may lack clarity on the people that you're most compelled to serve, but you can still go into different worlds and figure it out. Be a volunteer or an apprentice, get yourself immersed in that world and things will start happening.
Dustin
It's obvious we love podcasting. We're on a podcast here at Get WealthFit. You too love podcasting. You got
Steve
We've been doing Reinvention Radio since 2009. We took some time off. One of those being way too early to the puck kind of thing.
Dustin
What did you see in 2009? It was hanging around with you, Gretzky.
Steve
You need to hang around me but do what I'm saying to do and then stick with it and you'll be all right. I happened to be too early and then I give up when the traction doesn't hit. That's the downfall. The best way to put it is I've always had a love for radio. I DJ’ed on the radio when I was in college. I opened my own club. I didn't want to be a radio DJ per se, where I'd have to be there every day.
I have the horns and do the morning zoo stuff and all that silly stuff. Radio has always been the Holy Grail for me. Podcasting was fairly early at that point. Having been online since ‘93 and reading the publications and being involved with TechCrunch and all those different worlds and so on, you see the technology.
I remember reading an issue of WIRED. It must have been around 1996 to 1998 or something like that. There was a small, maybe a third of a page article about Burning Man. It was way back when. Now, it's a big thing. I don't feel like spending days in the desert. It doesn't sound like fun to me. Maybe I'll go at some point.
The point being is had I gone then and been a part of that Burning community, which I was like, “Maybe I should check this out,” and never did. I would have been in the embryonic stages there too. It was the same thing, reading WIRED and TechCrunch, all those stuff.
It was like, “There's a germ here of a pretty interesting idea, a pretty interesting way to communicate." There are people who will tell you that podcast had been around for a lot longer than that, like a decade or two before that. Whatever the original data, it doesn't matter.
It was still fairly early that very few people were doing it. I felt like it gave me an opportunity to create this platform where I could interview interesting people who were also reinventing their lives. That's where Reinvention Radio came from.
Dustin
You weren't thinking monetization. That wasn't the game back then.
Steve
It wasn't. It’s just that the Holy Grail for me was radio. It was, “I'm going to buy my own radio stations called a podcast.”
Dustin
Why Beyond 8 Figures?
Steve
Beyond 8 Figures is a fun show for me because as an entrepreneur, I'm always curious in terms of how entrepreneurs are wired to excel, how they do what they do and how they got from point A to point B.
We exclusively feature entrepreneurs who have either exited for more than $10 million or currently run businesses that gross more than $10 million. They bring a unique perspective to the table.
The average guest has either a business that generates or an exit in excess of $300 million. We could call it Beyond 9 Figures just based on the average. The point is it's all about starting, scaling and exiting a business in some cases.
I've always been curious what was that leap? What's the difference between the five-figure business and the eight-figure business? What's the difference between the six-figure business and the eight-figure business, the nine-figure? Is it the key hire? Is it the key initiative? Is it the key endeavor? Is it plain dumb luck?
What happens to make that leap is, believe it or not, pretty rare air. That's what we try to do on the show is getting to the bottom and we don't let them sit. I asked the hard questions. I ask the questions that you want answers. I want to know specifically how much money you make. Where's that money coming from? What are your margins? What did you do? Who did you hire? What mistakes did you make? The whole nine.
Dustin
I'm self-interested and I'm asking you to do the impossible, which is give us a cliff note of all the guests that you've had on the show. What is one thing or if that's too hard, two or three things that stick out to you to get to eight or even nine figures. Have you identified any patterns?
Steve
There's one key pattern which is, and this will not be rocket science and I'm sure your audience here knows this, but the bottom line is you can't do everything by yourself. You won't be able to grow a meaningful endeavor if you've got your hand in every pot.
The way to best think about this is the analogy of a salesperson. One of our guests had talked about how their growth was directly reflective of building their sales team. That's obvious. It's not so obvious from the standpoint of he finally accepted the fact at some point early on in the journey that, “If I put somebody out to sell, they're not going to be as good as I am.”
They don't know as much as I know. They don't have the same passion as much as I have. They’re probably half as good as I am. They go in, knock on ten doors. Maybe they close six. Whereas if I knock on ten doors, I closed twelve. They’re half as good as I am.
What does that mean? What it means is that if you've got one guy on the street, you're now one-and-a-half acts. It's what you're doing plus what they're doing. If you've got two guys on the street, you now have two of you on the street.
Even if they're both half as good as you are, it's the equivalent of having you on the street. If you hire four of those people, now you're to 2X. For a lot of them, it was the realization that they may not be as good as I am, but even if they're half as good, if I put enough of them on the street, it's exponentially more powerful than what I could do on my own.
Dustin
I wish I had that realization earlier in the game. You've got to stay true to it because it's easy to go and start that and then have false starts or whatever and be like, “Screw it. I'll do it.”
Steve
The other thing that I'll say is they were willing to break what was working. What works when you're running a six-figure company will not work if you're trying to run an eight-figure company. You have to go in and be willing to break what is working. That for most is hard to do.
Dustin
I want to ask you about the
What's the story of putting this together? What's the play for you? It doesn't seem scalable. What's your ulterior motive?
Steve
The New Media Summit is an event that we've been doing since September of 2017. It’s a unique event. I've done other events in the past. This is a unique animal from the standpoint of we give 150 attendees the opportunity to take the microphone at center stage and we give them time to pitch 40 top podcasters along with the entire audience.
Dustin
Do you give them coaching ahead of time or you let them go cold?
Steve
We give them coaching. We do four pre-event training sessions to make sure that they're ready. We create one-sheet and we do the coaching and the whole nine around that. It's unique from the standpoint of every attendee takes the stage.
They have the opportunity to pitch the podcasters along with everyone else in attendance on who they are and what they do. They get booked on the spot. The core promise of the event is you will come to the New Media Summit and you will leave with bookings on podcasts in hand. We fulfill that every single time.
The reality is we have a 100% track record of people coming to the summit and getting booked on shows. The average attending gets booked on twelve shows. It's interesting and your question is well-taken in terms of why I'm doing it. First of all, it's a revenue generator. I'm not going to sit here and share that it's not a revenue generator. We charge a fair price for it, but we also deliver quite a bit for them.
They walk away with results. They walk away with a media one-sheet. They walk away with training on how to leverage and monetize the power of new media. If they want to start their own podcast, we have the Launch Your Podcast Program. If they need an online funnel, our team can build their funnel.
There are services that we offer in conjunction with everything that we're teaching at the event. It’s definitely a revenue generator, but it's also a credibility and authority positioner for me in terms of I'm not Joe Rogan. I'm not going to be Joe Rogan. It's not going to happen. I didn't come with another platform that I could then move people into this world. I'm not Ron Burgundy.
How do I make my own dent in this world that I love so much? This is an opportunity for me to sit at the epicenter of some very smart professional podcasters because we bring in 40 top podcasters and position myself as an expert in this industry scale. Because we give everybody the microphone, we have to cap it at 150 people.
The only way to scale this event is to do more of them. Here's what I say about Reinvention Radio and Beyond 8 Figures, they are not the biggest shows in the world. You will not find our show sitting next to the Joe Rogan show in terms of the number of downloads. It just doesn't happen.
I have the number of downloads that I need to support the lifestyle that I want. It's the same thing with the event. We're able to make enough money or profit from that event to be able to support the lifestyle that I want. We do it a couple of times a year. I develop real relationships with all of the attendees, all the podcasters and eventually, who knows.
Is it a saleable event? Maybe. It's not called the Steve Olsher Show. It's the New Media Summit. Would this work in Australia? Would this work in the UK or Europe? I don't see why it wouldn't.
Dustin
I think so because there are events out there, but the fact that people are walking away with an actual tangible booking on a show versus going to an event, learning how to pitch the media like they're walking away. I think that's a unique thing that is here.
I want to fast forward maybe a couple of years, it's New Media Summit. Obviously, podcasting being it, but do you think about YouTubers and new media?
Steve
That is one of the ways that our event is for sure scalable. Intentionally named New Media Summit as opposed to Get Booked on Podcasts, Get Booked or the Podcast Summit or whatever it is, because there are a lot of interesting developments in the world of new media.
As a matter of fact, in the next New Media Summit, we have a couple of people who dance in that world in terms of doing Facebook Lives and getting some big audiences that tune-in and watch their interviews. We could end up with different rooms and more attendees. You pick which medium you are most interested in from a new media perspective. It'll be interesting to see how it evolves for sure.
Dustin
What's the future look like? What are you working on? You've got real estate in the background, New Media Summit is rocking. You've got the shows going and probably umpteen other things going. What are you most excited about? What's the future look like for you?
Steve
I've been in a state of neutral, a coasting state for a while. I only work three days a week. Tuesdays, Wednesdays and Thursdays are the main days that I work. Occasionally if things come up, I'll do whatever I need to do. I do Reinvention Radio and Beyond 8 Figures on Thursdays. I do most of my interviews on Tuesdays. I do what needs to be done on Wednesdays.
My kids still don't know what their dad does. They've got no clue of it. They see me and I work out of the house. I don't even have any full-time employees. I've got one, three-quarter times. She runs the Steve Olsher brand so to speak including the New Media Summit.
The point being, even though I've got my hands in a lot of different pots and doing a lot of different things, Liquor.com is you don't have any day-to-day with it.
In the development stuff, I've got management companies that run those properties and partners who run those properties. I don't have any day-to-day with that. The residuals are there. The Steve Olsher brand so to speak, I've got my right-hand person who runs that. I plugin as needed. We still have the bandwidth and I need more going on.
I'm a little bored right now. I hate to say that, but I'm ready and willing to do some development here in San Diego. I've been kicking around a new idea. I don't even know how I would describe the concept in terms of it's not a dot-com. The long story short with it is it's called Latatud.
If you think about Software as a Service where you pay a monthly membership fee to get access to software, Latatud is housing as a service. It combines a lot of my real estate development background with my background in tech.
For one set membership fee, members will have access to Latatud-owned and fully-furnished and beautiful locations. They'll be able to move from locations as often as every 30 days. They'll have that flexibility.
These are private units so they will have privacy. There’s no co-living or shared bathrooms, kitchens, etc. They'll have privacy and then they'll build equity as if they're a homeowner without the headaches of homeownership. It's creating a new category of real estate that I'm calling flexible housing.
There will be a lot of work that goes into getting that off the ground. If that idea of creating Latatud with me is appealing, reach out because I'm looking for partners right now to help bring that to fruition.
Dustin
You're going to have to raise for this, do you think?
Steve
There are two phases to this. There's the, “Let's get some hands raised phase. Let's build out the website and do the marketing.” My goal is to get 1,500 people to raise their hand and put down a small deposit to say, “I’m in. When you guys launch, count me in,” knowing that 90% of them aren't going to say yes when it's time to launch.
We'll get those people lined up. We'll get them in place and then after that, we'll move into the actual acquisition of the real estate. That will be phase two. The reality is with 150 members, it's a Unicorn all day long. This is not something I'm looking at massive scale on, but with the average door being $500,000 per door, it's a lot of real estates.
Dustin
We've covered an incredible amount of ground. We talked to
Steve
I certainly would suggest that if you're interested in discovering what your what is or you know somebody who should be discovering theirs, start at WhatIsYourWhat.com and you can grab a free copy of the entire New York Times bestseller there.
That will also get you on the mailing list and that will keep you posted on all the fun stuff that we're up to. Outside of that, listen to Reinvention Radio and Beyond 8 Figures. Those are great things to do.
Dustin
Thank you for being on the show and for what you're up to in the world.
Steve
I appreciate you having me on.

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