Overcoming the Darkest Lows of Entrepreneurship | Real Stories & Solutions

All right, so, uh, we were hanging out at, I think, the coolest bar I've ever— have you ever been to a bar like that, Rich?

Every year in Durango, that's our thing. Got to go to the speakeasy, man. We've been going there for 14 years now.

Oh, it's always the same place, huh?

Yeah, it's pretty awesome. Isn't it cool though? It's like, it looks like a barber shop when you walk in, and then you do the little secret password and behind the library I've never experienced something to that effect.

I've seen the cheesy ones like where you pull a book off the shelf or something. But I asked the guy there, I said, is this a functioning barbershop? He says, oh yeah, yeah, you can get a haircut. It's like, my God.

Yeah, yeah.

You say a secret password and you're in that space. And it was beautiful.

Of course, as you can tell, I've not taken advantage of their services.

So now, now, but, uh, we have taken advantage of is, is the, the network of folks there And, and the staff, like, I've never seen, I've never been to a bar where the staff comes running up to a patron and like, oh my gosh, you're back. How are you? How did you build such an affinity with those folks?

Yeah, that was, uh, you know, it's, I don't know if that's a good thing or, you know, if I get in that good with the bar, bar staff, is that a problem or is that a good thing?

I don't know. I don't know. They did know your drink. They did know your poison.

Oh, that was fun. Yeah, I love that place. I mean, they treat you right. Everybody's really sweet there. I mean, it's just, you know, the whole city is kind of that way.

And I think you even said you used to work in hospitality yourself, right?

Oh my gosh. As a younger man. Yeah, I was a big Marriott guy back in the day.

Okay, so you know what those hours are work like? You know what the customer experience is like?

Yeah. And no holidays when everybody else is enjoying time with their family.

Yeah, I totally get that. Yeah, that's when you got to double down on work.

Yeah, it's actually, you know, I thought becoming an entrepreneur would actually be less hours, but I was wrong on that too.

So yeah, I want— this is what we're going to explore today. I want to talk about your entrepreneurial journey, but unlike, I think, like a podcast or something where they say, well, tell me, uh, people don't know about you, I want to start right in the meat of it. So we're at that event, uh, we got into a deep conversation very quickly.

Yeah.

And you start sharing some stuff about your journey, and I want to start at that, that dark spot. You've been very successful and I want to talk about that too.

Yeah.

But you went through a deep struggle. Tell me about the, the down spot.

Well, that's one of the reasons I think you and I hit it off so well is because our, our struggles were so parallel, you know, the, the story was so parallel. I was, I kind of got chills. I remember them as if it was yesterday. It was, you know, in the '90s we had a software company. I was, I've been a software guy for 40 years since back in the day, right? And You know, I started my sort of first company in the '80s, built up some great successes, built up some what we used to call service bureaus. Now they call it the cloud, right?

Oh, I actually didn't know it was called a service bureau.

Is this a server?

What was that?

A bunch of servers in a rack, you know, you know, doing business for people so that they didn't have to invest in millions of dollars of equipment back then. So smart.

Yeah. And right now it's the cloud. Yes.

Yeah. So the, you know, it was very, very similar to what you went through. You know, I sold off one of my internet companies, made a bunch of money, thought I knew what I was doing. I was in my 30s. It was like, hey, first, you know, several million bucks in the bank, and it's like, hey, let's go for it. Let's— I can help others do this, right?

Yeah, yeah, yeah, yeah, yeah.

And, um, yeah, I mean, the, the term you used, you know, in, in your interviews, angel of death. It's like, man, I— it was like everything I touched just turned to crap. Now, I could use the excuse that, uh, the dot-com bubble burst and every one of my investments was technology and dot-com based, Yeah. And, uh, I could even go as far as, oh, well, you know, if you look at those businesses individually, they all had merit and they all, you know, today are, would have been awesome businesses. But anything with the dot com after it, just, you know, everybody just pulled their money out.

Yeah.

So, uh, you know, and I would be lying if I didn't say that I didn't have some fun with that money too. I mean, you know, we bought a house on the beach and we were flying in planes and we were, yeah, yeah, yeah. Cool stuff and making ourselves look even more important to the people that we were, you know, giving money away to. You know, I keep thinking it's like one of the questions I ask you, it's like, you know, first of all, how do we get through that dark phase? But then what is— what's inside of us that we feel that we have to seek the approval of people we don't even know?

What is that? So, so tell me about that phase of seeking approval. So you're giving money to people. What, what was the justification behind that, or the reasoning And what was the real emotion behind that?

Well, I'm sure that ego had a lot to do with it. You know, when we have a success, we've got lots of money in the bank, we've got assets, uh, we don't feel like it's ever going to end, right? Yeah. And, uh, we don't— and of course, at that time, at that age, I didn't have enough background to understand that, oh, it could all disappear tomorrow. Yeah. Um, I knew my industry, I knew it well, and I did good in that. But in terms of investing and stock markets and analysis and legal documents in terms of angel investing and venture capital investing, those were all brand new things that I was completely, you know, a newbie at. And it showed because my documents, or lack thereof, put me in positions where it was really difficult to get any of that money back or to continue to go deeper into the company or have any assets whatsoever. We were, as they say, subordinate to everything and everyone else. So So yeah, it was, but I don't know, man. I think it's, you know, some of it has to do with ego, I think, at that time in our lives. But I also think there's some greed involved too, because I'm thinking, oh, this is going to be easy money. If I, if I put a million here and a million there and a million there, I'm going to have, you know, $20 million a couple years from now, and then I'll never have to work again. So all those little things go through your head, and it all seems correct. And justifiable, um, until you actually put a spreadsheet to it, which is what I should have done. Yeah.

So, so you went— you were a multimillionaire in your 30s.

Yeah.

Uh, you lost it all, pretty much.

I mean, almost all, you know. And here's what made it even more— and this is the part that I wanted to talk to you about, the depression stage, because I, you know, I just sold the company. Yeah. Just had a brand new baby, first baby, lost my dad to cancer 2 months later, and then everything went to hell in a handbasket a year later. So I mean, within an 18-month period of time, it was this huge emotional roller coaster of selling company, new life, new family, lost family that was very dear to me at a very young age. Uh, because he was only like 63 at the time.

Oh my gosh.

And then, uh, and I, You know, that's what I— when that happened, I just lost track of the investments. I didn't get on the phone. I went into a depression stage. I didn't pay attention to the markets anymore. I just went into this dark place. And then I woke up one day and all the— I got calls and all the money was gone. Um, you know, so it was a very emotional, you know, roller coaster is an understatement. I mean, it was more like a, just a, a huge crash and burn. And, uh, I'm embarrassed to say you know, how much money just got pissed away. It was just, you know, embarrassing.

You know, you're— it's not embarrassing. And you're helping. There's someone watching right now who needs to hear this. And I want to contest, I don't know if it's because we're young. When I lost all my money too, I happened to be in my 30s. I don't know until you go through the experience that you really appreciate it. I think you can be, I don't know, in your 50s or any age.

Yeah.

And the first time that money comes, I remember my ego going, oh my God.

Yeah, yeah.

I've figured out all the answers to entrepreneurial struggles. I am a genius. And let me show the world.

Yeah, it's funny. Just, just for a moment, we were—

for a moment, were we really? Or were you and I in the right place at the right time and gifted and granted a lot of luck? White males.

Yep.

A group in, in the United States.

Yep.

You know, imagine living in, let's pick on North Korea. Imagine you and I were born in North Korea and yeah. You know, we wouldn't, so there's luck. There is grabbing that tiger by his tail. Like there's effort, there's no question about it.

Yeah.

There's the application. But then we lose. What's interesting is when we, when I lost it, I blamed it on, on purely me. I, I said the only reason I lost it is cuz of me. When, when I gained it, My ego says it was only me, but in retrospect I said, oh, there's a lot of factors.

Yeah.

But I still struggle accepting that my loss was, was not just only me. I, I'm, I'm struggling to say other factors.

I have that same problem. I mean, I'm like, you know, at a very young age I was taught accountability.

Yeah.

And, uh, the problem is I took that too far to the other way. I was like, everything is my fault. No matter what, whether it's good or bad or indifferent or relationship or business or whatever, I, I take accountability for everything. Yeah. And, um, you know, and I believe in all the manifestation stuff, good and bad. Sure. Um, so therefore that puts me in a very, you know, weird position because if things are going well and I'm manifesting well and I'm putting off good energy and, you know, all those things that we— the woo-woo side of the business world, right?

Yeah.

Um, then we feel like, ah, I must be vibrating at a higher level or something, right? Right. And then everything goes to crap and it's like, oh my God, I might as well be in a coffin. It's just, uh, it's just, it's terrible. It's terrible. And it's true, it just, it gets worse. It's like a whirlpool, um, you know, it's, uh, it's really hard. It's like a riptide, it's hard to swim out of it.

Yeah.

And, uh, you know, there's been news stories lately about people losing their lives in riptides, and I keep thinking, well, it's real simple for us to look outside looking in. Why didn't you just swim with the tide?

Yeah, yeah, go with it.

And I'm thinking to myself, it's like, well, first of all, do you really know you're in it? Sometimes you do, sometimes you don't.

Yeah.

Second of all, do you really know your own limits? As entrepreneurs, I don't think we do. We think we're limitless. We think we have all the strength in the world that we're just going to keep swimming and it's going to get better.

Yeah.

And so it really was a good analogy for me because it was like, you know, when do we, do we even know what moving off to the side is? And Kate, maybe pivoting is what we would call it in the entrepreneurial world. But I don't think we realize how tired we really are.

That's such a good analogy.

Yeah. Until we just drop or we lose someone or something, whether it's a person or a relationship or a business. We don't remember until the loss.

It's such a good— I remember I was at the ocean once. It wasn't a riptide. Yeah, I was just out playing in the waves as an adult, and the waves hit me and tumbled me, and that's when I realized this force I can't stop it. And a little bit of water went in my throat. I was like, I was like, I am seconds away from passing away.

Yes.

You know, once you're in it, you, you realize how fragile you are.

Yeah.

And I wonder in your business experience, the fragility of the cash you'd earned, and did you have any awareness around that? Like, when did you take that first gulp of water?

And then it starts this No, it's interesting that you say that because, um, and again, this is, you know, reliving the past. It's painful, but you're welcome.

You're welcome.

Yeah, I, um, I put a lot of money in places that I thought was safe too. I mean, I had enough to where I could blow a bunch. I had like 3 bank accounts. Okay. One was, I'm just going to blow it on having a good life because I just lost my dad and a brand new family. I needed something to keep my new family excited.

Sure.

And, um, or at least I thought, you know, and I thought that would help and it did there. I won't lie. It did. When you're sitting on the beach as opposed to in a dark room, it's, it's much better. But yeah, I agree. And then I had, and I had one bank account that was conservative. Let's put it in mutual funds, people that are smarter than me, they know what they're doing. And then I had one bank account that was the angel investing account, right? Where I would just, you know, help incubate all these different companies. And even the mutual fund account went to hell. I mean, this was the PIMCO days when they went out of business and there was all these lawsuits and every people going— I mean, it was just awful. Everything across the board just went away. Yeah. And, um, oh my God, just the, you know, so yeah, it was, uh, by the time it hit me, it was too late. I was already underwater and I knew that, um, this was it financially. Um, so I had to— you know, I had to start all over.

How long did this all go down?

So yeah, this was in— so I sold the internet company in '98, end of '98. Um, spent 99 doing the one-year thing before you can— you know, 1244 stock is a public company. You know, didn't do my tour of duty. Yeah, yeah, yeah, yeah, yeah, yeah, yeah, yeah. You know that story. I know. Yeah. And, um, got all my options vested, all that kind of thing. And then the early 2020— or excuse me, 2000, right after Y2K. My dad died on December 31st, 1999.

Oh my.

So, and I had already been involved in a bunch of Y2K stuff. Thankfully, we had already had it all worked out. Yeah. So, uh, I woke up the next morning and nothing was gone and exploded or anything other than my life.

I remember, I remember that day.

Yeah.

Watching the ball drop in New York saying all the lights are gonna go out in about 2 seconds.

I, uh, I remember being on the couch with my mom and we're both just sitting there sobbing together, you know. What do we— at that point in time, I wanted the world to end.

What did your father pass from, if I may ask?

Yeah, yeah, cancer.

Yeah, cancer.

And it was pretty brutal for the last couple of years, and then the last 2 weeks were even worse. And, uh, and I was— I had just spent 2 weeks in the hospital from, from Christmas to New Year's, before Christmas. Excuse me. And, um, you know, and I remember that night when I saw the ball drop, just like you did, I was like, you know, I hope all the work that I did to get prepared for this night all disappears and everything blows up. I remember— I remember saying that to myself, because then everybody will feel like I do. It was almost a— yeah, cry out for help, or, you know, something. Um, it was a pretty bad time. And then of course, you know, I just went into a spiral and, uh, shut myself off from the world and all the investments I had made. And I woke up a year later and everything had crashed and it was gone. And had I been paying attention, I could have got into the short games and I could have cashed out and I could have pivoted. There's so many things, you know, Monday morning quarterback that we go back and think about. Yeah, I even remember looking at documents as if it was yesterday that, that were warning me to get out. And I remember this yellow newsletter that I got in, in early 2000s, like it's telling me all these companies that are about to just tank and all these stocks that are tanked. And sure enough, a few months later, they're all gone. Like it said, they're all gone. And I could have remade millions if I had turned those investments around and shorted them all, right? Yeah. But, um, you know, I was a tech guy, so everything was like, hey, the companies I'm invested in They're solid, right?

They have product. And the irony is, yeah, they were solid.

I bet. And they were not pre-revenue. They had revenue coming in the door.

So revenue, solid tech. But the world said dot-com is on it. The bubble's burst.

Yep.

Now we're recording this. This is summer of 2024. This is 24 years later.

Yeah.

You're, you're still feeling the ripples. When we were sitting at the bar, uh, You know, we started hugging it out like it was— and I don't think you had a drink yet. I'm not drinking. And we're kind of hugging and crying like, oh my God, these guys are wasted. You tell me about today and how you're feeling even today.

Well, you know, that's a good question. I wake up every day grateful because I've been given another chance. That's what I look at the morning as. And when I hear people griping about Mondays, I'm like, don't gripe about Mondays. That just means you've been given another chance by the spirits, you know?

Yeah, yeah, yeah. Yeah.

So, uh, so I've really learned to practice hard on that. Yeah, part of it. But, and this is why, you know, why I think we had such a good conversation that night. It's like, I have— I don't believe that I've fully learned how to let go.

Yeah, yeah.

And I remember asking you that question. I said, Mike, because, you know, you went through almost exactly the same thing. And it's like, How do you finally let go of the shame and the regret and the pain and the what could have been and where I would be in my life right now had I not made those mistakes? I mean, I was reaching out to you for help because it was so— to this day, if I think about it, and that's why I told you I wasn't really sure I wanted to have this call because, you know, stirring up the past, it's, it's still, it's still an open wound.

It's still an open wound. It's still using—

there's bandages all over it. Yeah.

Yeah. But it oozes right through and the infection still exists, right? We haven't gotten rid of the infection. Um, it's so, you know, how do you let it go? And, and that's, that's why I'm so happy recording this. Uh, that, that's the big question. But I, I also found from my own experience is talking about it publicly and finding out no one cares. There, there was a famous saying from someone who said, the people who really matter don't care. And the people who care don't really matter.

Right.

You know? And so when I went public with, I lost my house, I lost our stuff. Uh, I didn't have, I, I call myself the temporary millionaire. I got, I made mil, a million plus.

Yeah.

And then taxes came and that was the first punch. I didn't even know that was coming. But, but when I had nothing left and I had, I had a, my wife coordinated, but we got granted a house, uh, Our friends went on sabbatical for 2 years and they said, you can use our house as house sitters for free, effectively. Um, the, the people who care, who matter, didn't, didn't care at all. Like, oh, you're still Mike. And, and the shame was gone because there was no one else to tell about it. And I, plus I put it in a book.

Yeah. For me, it was, I don't know, I'm, I'm having, I'm not as, that's why I'm asking. That's why I came to you because you figured out a way. I mean, for me, I still look at my wife and kid and think about, I mean, and they're doing great. I mean, my daughter's a nurse now. She lives in Salt Lake. That's amazing. My wife has her own business. She's very successful at it, changing the world, you know, one, one woman at a time. And, um, so they're doing great.

This bold question, and I ain't no psychologist.

Yeah, but it's just, it's a self-shame issue that I feel like I've failed them personally, you know.

Well, so here, let me ask you two questions as a psycho-psychologist, because I ain't one. Have you asked them, um, that question.

Yes.

I feel like—

you've not— it's what you said, the people that matter don't care.

Yeah. So I would add, I would maybe ask— I, I maybe— I would ask my wife and my daughter, say, I failed you. I define that myself. I need to know from you, did I fail you or not? And speak the truth.

Oh yeah, that's— I believe me, I have. And, and they assured me you've not— wasn't the case.

And step 2 is Have you forgiven yourself?

And the answer's no.

Yeah. Flamingo, flamingo.

It's like that. I've done enough hours of whatever you wanna call it, study, meditation, therapy, talking to people where I, that I can answer that question confidently.

No. So, you know, this is such a great conversation cuz Rich, I don't think many entrepreneurs get this is a big part of the entrepreneurial journey. Everyone talks about, yeah, grow your business, you know, make millions.

Yeah.

Like what about when the struggles present themselves, how do you manage it? And, and no one's coaching us on this.

Yeah.

The two things I did, and I'm curious if you try these, is I started journaling. I don't have it with me, but I just would write, not a journal like, oh, I'm successful or happy or gratitude. I would just write down whatever emotion was present, present. And it was cathartic. It was like the cheapest form of therapy on the planet to say what I wanna say. I was cursing out God undeservedly, but I was. The, the second thing was saying to myself, I forgive myself.

Yeah.

And I said it enough times now in my life that I've actually accepted that to be true. The first time I was like, okay, you said the words, but you don't mean it.

Right. You're right.

Maybe the 100th. And then it was, okay, this chapter's done. That will always be a chapter in the book, but it's done. And I suspect you have you haven't completed this chapter yet. Like, we haven't, and therefore we can't move on to the next chapter. That's what I'm sensing.

Yeah, no, you're absolutely right. And it's because, um, you know, some things have happened again after I built things up. It happened not quite as bad in the 2008 crash, but I had just conservatively saved up enough to make it where we're going to be okay and made some investments in the real estate. And yeah, I'm thinking, oh, real estate's a smart way to go since I screwed up everything else.

Yeah, did you screw up everything else? I don't think you did. You know, it's unavoidable. Like, 2008 is unavoidable.

You— yeah, yeah. But it's, um, but again, you know, for whatever reason, I blame myself because I didn't have to invest in real estate at that time, you know. And, um, and if I would have waited 3 more years, or if I could have waited 3 more years all those things went back up again, of course.

And funny is, what if, what if 2008, what if the stock market actually— it wasn't the dot-com bubble, but the dot-com double down, like it just expl— you would, dude, you would be like on the COVID of Fortune magazine saying, oh no, Rich McFarland, the smartest human on the planet. Like, we're, we're literally one event, not a decision, it's the same decision, one event from world fame to, to world shame.

Well, and I think that's one of my problems. I mean, when hearing you say that out loud helps because I think about, I always think about what could have been, which is the most dangerous thing you can do to yourself because I was just a few months away from being the 9-figure guy, which is a rarity in this planet, right?

Yeah.

And when it all goes away, it's like, you know, when I see guys around me who I was in YEO with back in the day, like the Mark Cubans of the world and Jeff Smiths of the world and those guys, like, like we were all struggling together back then.

Yeah.

But of course they made it, you know?

Yeah.

Yeah. He, he called it out just in time. Yeah. Yeah.

Yeah. So, so luck was in their favor, but yeah.

And, and I wasn't smart enough to do all of those things. Yeah.

I do. I got to challenge you here. Not smart enough. You're wickedly smart. You couldn't. Okay, so you can't. You're not Merlin. You kind of look like Merlin, but you can't predict the future. You can't predict the future. It's funny, I tell people, you know, those bullshit business forecasts and business plans and people, you know, year 1, this year 2, and by year 5 it's going to be this. I'm like, oh, you can predict one day in the life of business. Invest in the stock market. You're about to be a billionaire. No, no one can predict the future.

Yeah. I've never seen a pro forma yet that's worth its weight in gold. Yeah. Yeah.

So I will say that, uh, Michael Dell, whoever, Cuban, those people, they're smart people. I don't think they're smarter or less than you or me. I just think they also happen to be in the right place at the right time.

Yeah.

And Yeah, they were capable. If other people, opportunity presents itself, they're not gonna grab the tail. They did. I think we overinflate, and I'm the guy who does it. I'm like, oh my God, Elon Musk. Like, look at him over and over again. Yes, he's amazing. He's brilliant, but he's human too. Yeah. And the right opportunity presented itself. If he was born somewhere else or he experienced something else, if, if, if there was just one decision made, uh, that he didn't get the phone call he was expecting or whatever. It wouldn't have happened.

I know, it's funny you mentioned Elon because when they were doing PayPal back in the '90s, we were working on a similar type function for credit card processing systems over the internet, which was all new back then, right? And we had created this really cool automated system using old Microsoft FrontPage, if you can remember those days. Yeah, yeah, that's the front end. And, and then we had all the backend servers and systems to do all that stuff. And we, we had similar technology and we even had some revenue coming in the door, but we get the VC funding. They did. And right about then is when everything went to hell in a handbasket. So they got, they cashed out, you know, when I think it was eBay that bought PayPal back then. And, um, and then we, you know, we missed it by this much. And, and I think that's why, because we're watching these people today, 20 years later, um, getting motivated from them and how, what great things that they're doing in the world with their riches and their, and the value that they're bringing to the planet. And I think that's what, like, if I just, you know, if I went and got a job at a liquor store and didn't do anything else and didn't watch the news, I think sometimes some days I almost think I'd be happier. Yeah. I bet. Because when I see these guys 20 years later who have made it and all the good things they're doing, and it's like, that could have been me, you know, why wasn't it me? Yeah.

Yeah.

Yeah.

And then, and then the cliff begins, you know, I remember I ran into an old high school buddy today, literally today he was, he was working in our building. He's not the guy. There was other guys in our school. We had our reunion. Remember going to the 30-year reunion? And the popular kids are, as a general rule, miserable. Yeah, look like shit. Yeah, their life is— it's shit.

Yeah.

And what I realized at that event is, my God, they're still in high school. Like, they're still like, I'm the king of the prom. I don't know what happened. Sometimes that early success is our biggest, uh, bane. It's that chain. So we got to cut, we got to cut it out.

Yeah.

Um, and you know what? The dude working the liquor store is effing awesome. I got a guy down here, it's the nicest guy. He brings so much. I know, he sells spirits and brings spirits. Every time I see him, like, hey, what's up? He's like, hey man, how are you? It's like He's contributing so much to our community. It's because by loving on people.

Yeah.

I walk out with my non-alcoholic Coronas, which by the way are more expensive than regular Coronas and they've removed the alcohol. So I'm like, this is a rip.

Yeah.

So, so let, let's rewind now real quick and then we're gonna, we, we talked about the middle where you are. Let, let's step back. Tell me about the, the early business growth. What you were doing. Tell me about the high times.

Yeah. So, you know, being in the software biz, I started really, really young, uh, back in the late '70s, early '80s when PCs came onto the market. And so we got really good at that and we were— and then mini computers came, but mainframes were still filling rooms back in those days. So my first success was helping people, uh, get off of these rooms full of mainframe computers that were costing them millions of dollars a year onto this new minicomputer like IBM's AIX system back in the day. I remember. And so we had a whole company in just helping people downsize or right-size, as they say. And we had several customers that at one time were IBM's biggest minicomputer accounts. And, you know, in the financial world and the health space, even Arthur Young was a customer back in the day.

Oh yeah, I remember Arthur Young.

Wow. Yeah, I remember the AY days now. And then Ernst Whinney bought them out. It became EY, which is what it is today. So yeah, it was even before that. Wow. So yeah, we, we did really well in that space. And, um, it was exciting because we, we had a specific skill set that a lot of people didn't have, and we could do it for faster and cheaper because we were, you know, a group of guys that understood both the old way and the new way. And we could help people make that transition. So I've always been in that space. That's kind of every company I've ever started in the software world. We were always, my thought was, okay, who am I going to sell to in 10 years or 5 years? So we would write software around that. And it was usually in a dilapidated industry where there was, you know, big dinosaur companies that have been there forever and they're just milking the cash cow. And it's too expensive for them to rewrite and start over their product line. So we would come in, rewrite from scratch with new technology, new capabilities, faster, cheaper, etc. And you know, and then end up selling out to one of the competitors later on. They would badmouth us all the way. Of course, you know, as we were stealing their customers all the time, they would, you know, they'd tell everybody how awful we were and we don't know what we're doing. And then 3 to 5 years later, they'd buy the company. So yeah, yeah.

And that's classic, right? If they can't beat you, they buy you.

So I've always had that, like you say, right place, right time. But I've also, I love the creative part of the business. So I've always been able to see that trend farther down the line. And I think that's what makes it more painful on the financial side, because when I look at technology, it's never been a problem, you know. I've never had a doubt of, you know, everything I've ever thought was going to happen in the next 3 to 5 years out usually did, if not sooner. And if it didn't, we created it, right? Um, I never got that skill set in the financial world. And, um, because financial world doesn't really change that much. I mean, you know, you still have trends of what's going to happen. And like you said, if we all knew about the Black Mondays of the world, we'd all be billionaires. Yeah. But, um, uh, so you sell the company? The real answer is I didn't pay attention to the financial part.

Okay. And I would suspect because that wasn't your interest and passion.

That was exactly—

yeah, that's our— that's the biggest mistakes I've made. I, I'm like, oh, I'll do this because that's where the money is, but not where my mind is. And then—

yeah, that's what I love about, you know, I did some research on the Your Most Successful book, and it's like, it really puts people back in the zone of like, why am I doing this? Let's, let's talk about financially first.

Yeah.

And then that will free you up to make some of the later decisions later in life. So, I mean, it's a, it's a really good fit, you know, for this conversation. Yeah.

Yeah. And in that book, it's Profit First specifically. I think so many entrepreneurs are trained to look at the top line and we never think about the bottom line. We think it's magically going to present itself. Then we get blindsided.

But it usually has brackets around it.

Yeah, true. It's in red brackets. And you have a stern look from an accountant. So, okay, so you sell the business, you make millions and millions, you then go through this process of losing the money. Let's, let's forward to today. What is the path forward? Are you going to start working the liquor store or one more shot in you? Like, what's going on?

Well, I sold the last software company that I had. I sold in 2017 and I put in my time there. And right about the time COVID happened was the time that I realized I didn't want to be in this space anymore. Okay. And so I made a deal with the owners of that company, and they were very, very kind. And because there was a lot of crap going down those days, and they— I think they were just as happy to get rid of me as I was to leave. So it was one of those situations where it just made sense to, like, step back. So I thought I was retired, and I thought, hey, you know, I'm just gonna sit, you know, I'm gonna drive around the country, you know, when COVID was happening. And everything was shut down, I put 33,000 miles on my car just that summer.

Wow.

Just driving around the country, going to truck stops, trying to interact with other humans, because they were the only humans that were working, right?

Oh, that's a good point. Yeah, yeah.

And you're a social guy, you know, that they, that they were putting up with all that stuff. But, um, yeah, I picked up a lot of really bad habits in those 2 or 3 years because, like, you know, I, um, I got— I really like the idea of not working, you know, driving, talking to people, interacting, um, you know, doing hobby work, etc. So I really literally thought I was retired. Yeah. And then I got bored out of my mind. And this is why, you know, I'm actually thinking about, you know, helping others that are thinking, oh my God, I'm tired of my life, I'm tired of my work. Yeah. You know, because I know that feeling. And, um, retirement's not the answer either. You got to find something that gives you reason to live. And gives you a purpose for the day. You know, we talk about the books of why and the purpose and all these things, but it, um, those are, those are in my opinion, very difficult to define. You have to look, you just have to move. I mean, you just literally have to move. So I went out and bought some companies, I, you know, uh, and acquired a few companies. The problem is I think I bit off more than I could chew.

Okay.

I acquired way too many companies too quickly. And now I'm deep in the, in the crap again, trying to make those and turn those around and make them run.

Trying to pump life into them.

Exactly. Yeah. Because, you know, again, I know how to run a business. I know how to do financials. I know how to do software. I know how to do, you know, the product lines and I know how to do wholesale distribution and all these different knowledge things that I've learned over the years. You know, so I've, I'm realizing it's not a knowledge gap. It's not a knowledge problem. It's, um, I think it's an emotional or a control or a self-talk issue. And that, again, this is why we hit it off that night and why I asked you those questions, because I don't— I'm not having a problem with what do I do tomorrow and what do I tell people to do in terms of operationals. That's not the issue. It's, you know, how do I convince myself that I'm where I want to be?

Yeah, I, I, yeah, that's the grand question. And for me it was forgiveness. I remember this, that when I was in my depression, I went through it for 2 years.

Yeah.

I was like, I'm worthless. You know, we talked even about suicidal considerations. I gotta be careful about how I frame that. I was not suicidal, but I was definitely contemplating ways to do it if that was the necessary action.

Yep.

And I remember anytime I made a mistake or failed, I would jump on myself and say, there it is. You are an idiot, McCallowits. You did it again. That's the proof. And I was like, oh my gosh, it's an affirmation or confirmation loop.

Yeah.

I am actually seeking ways to prove I'm an idiot so I could do 90% things right or 100, 99% right, one wrong, and everything else was blocked out. Yeah.

I mean, you're, you're spot on about words and affirmations. You know, we, we, those things are spread all over the world in terms of, and they have been forever. I mean, back in the Wayne Dyer days, he always told us about those things, but it's, um, I've, you know, it's a dangerous space because I remember, you know, I, um, I had lost two very close friends to suicide and I'm still angry at them to this day because of the beautiful families they left behind. And, and I couldn't see myself doing that, but what I did starts, you know, when things were so bad financially, we still had life insurance. Wow. And I started thinking to myself, yeah, am I worth more to my family dead than I am alive? And financially, the answer was yes. Yeah. So I couldn't argue the fact, even though that's a terrible thing to say and a dangerous place to be, I couldn't logically debate it because it was true. Yeah. Now, only financially, of course, you know, and having such a wonderful wife and daughter and family is such a blessing because they're like, oh no, but what about this? And what about this? You know, they're giving me the reasons I need to stay around, you know, and thank God for that. But it's, they're giving the truth. Those words that we say to ourselves are so dangerous.

Entrepreneurs, we're so trained or groomed to talk numbers. And it's, it's ironically, it's, yes, it provides access to things easier. It does give access to certain comforts in a big way, but the essential things are always the free things, right? Love, health, all these things that we can care for, uh, usually without money.

Yeah.

Um, and yet we don't measure that.

Yeah. I wish we would.

Maybe that's the great lesson.

There's a product idea for both of us. Yeah.

Just, it's just about being human. It's funny. I think about some famous people have a great impact. Gandhi, Mother Teresa, these people, I presume, managed hundreds of millions of dollars of donations and so forth. It wasn't, they didn't represent themselves like, hey, I have $100 million. They weren't worth that, but they managed it and look at the impact they've had. Yeah, I can't say they were happy individuals. I don't know anything about their life stories. Dude, just after talking with you like this, this guy's— it's going to do something impactful, something big. And I don't know if it's an entrepreneurial venture, if it's— if it's just this one podcast that starts a cascade of you sharing what the real entrepreneurial journey is about, or if it's working at that liquor store and just loving on people. I don't know what it is, but I just— when we were talking, I was like, I got to get you on this podcast.

Yeah.

And I also think that the people who see this that are your friends, the ones who care, the ones who matter won't care. And the ones who— the few people who cared just don't get it, right?

Yeah. Yeah, no doubt. Well, unless they've been through a similar situation and that, you know, I got to tell you, I was— didn't sleep a lot last night because, you know, I know you were right in saying that the best way to get through, or at least get some assistance, is by saying it out loud and saying it publicly. All right. I had a lot of doubts about that all the way up until like about, um, an hour ago.

It's hard. Yeah. Is there anything else in the story that you wanted to share that we didn't touch on?

Yeah, I just, you know, I just, uh, I hope you're right. I hope that— I mean, if we can help one person.

Yeah.

You know, just feel better about this situation because it can get very deep and it can get very dangerous and it can get very ugly and dark. And, uh, you know, I don't want us to create a community of misery, you know, company, but I want it— I would love it if there was a community of, of help. Yeah, you know, of how do we, how do we get others to come out of this because I still to this day don't— you ask me the question, what do I do now? And it's, I still don't consider myself free. It's like, yeah, perfect analogy is I know people that, um, thankfully my body wouldn't let me do hard drugs, um, at any point in time. So I was very fortunate with that. But I have friends and acquaintances and family members of them who did, and they're, they're, they're terrible addicts. They went through rehab 2 or 3 times. They've lived just terrible lives. Yeah, you do anything to get another fix. Yeah. And then they finally get intervention and they finally make the change. And then 3 years, 4 years, 5 years, 10 years later, they're still sober, right? And whether that's alcohol or whether that's hard drugs or whatever. And I remember talking with them and talking to people who had been through the different programs. And I remember them saying, well, you're never really not an alcoholic. You're always, always an alcoholic. You just happen to be sober for 10 years because you, you realize, you admit to yourself that you, you're still that, but you found a way to control it. And I just, I thought, what a cool— and now I'm not cool, but I mean, what a perfect, what a perfect analogy is that I don't feel like I'm out of the woods just still to this day. Yeah. so maybe that's it. Maybe I am a functioning financial holic, you know, maybe.

Yeah, man, that's it. There you go.

And whether it's going good or bad doesn't matter. I still have to pay attention to that weakness of I've got to please other people. I've, you know, and, and by giving them money, maybe that'll do it. Yeah. You know, and, um, yeah, so it's, it's an ongoing battle. It's an ongoing conversation and That's why I believe I agree with you. You know, words are important. Words are very important.

And the ones we say to ourselves are most—

our internal words.

Yeah, totally. Hey, Rich, uh, thank you for this. Hang tight, I'm just gonna stop our recording.

Yep. Thank you.

And can share us out.

Yeah, hold on.

I sure you want to