Losing $40 Million Changed How I See Success (Anthony Vicino)

I had personally guaranteed $40 million worth of real estate. And listen, that money's, that money's gone. It's gone, gone. It's not coming back. Holy crap. You need this thing. You can't just ignore it. You can't just pretend like it doesn't matter because money doesn't solve all your problems, but it solves all your money problems. There's a lot of problems that revolve around money. And I had to learn that the hard way. Anthony Vicino, an author, creator, and entrepreneur who built a million-dollar window washing business, co-founded a climbing gear company and went on to raise $40 million in real estate.

So what is it like to go from that high high to all of a sudden watching these things fall apart?

There was a 6, 7 month period there from October through about March of last year where it was just real dark days. As you both navigate the reality of, holy crap, we have a sinking ship here, how do you forgive yourself? I'll pause there because it's a lot. It's not about what you own, it's about what you— There was just, over the last year, there was a period of time where the universe was definitely saying, here are the lessons that you need to learn now, and you're going to learn them in the most, um, most uncomfortable way that you can. And there's so many lessons. The biggest one though is There's a confidence shift that comes once you realize you have the ability to make money. Then it's a skill that can't really be taken from you. And for the first time in my life, that's when I felt like nothing can ever break me financially again because I know I can always make it back. It's interesting given everything that's happened this year.

What do you wish you could go back and tell yourself or that would have helped you? Welcome to Money Stories, where we have conversations with founders about money, meaning, and what makes a truly rich life. Today I am joined by my dear friend Anthony Bassino, who, content creator, writer, has a holdco that is focused on companies that help people improve their life ROI. Very cool mission and tagline. I'm excited to dive into this conversation. I've got a lot of respect for the content that you create, the views you hold, and I'm excited to dive in. Welcome to the show.

Thanks, thanks, dude. I, I told you this before we went on, is like, I don't do many of these anymore. And so I'm partially nervous and excited because they're like, they're sister emotions, right? Because we get to talk about some stuff that people don't talk about when it comes to entrepreneurship, like the hard parts, the scary parts, the parts that we prefer to keep hidden. So I'm really psyched.

Yeah, same. I mean, that is kind of the fundamental reason I created this show is entrepreneurship is beautiful. It helps people create dream lives, employees. There's, there's a lot of upside, but there's also a lot of dark sides.

Yeah.

And, uh, I think it really is important to, to just shed light on that part of it because, you know, so many founders are suffering in silence. And so I'm, I'm excited to dive in. And on, on that note, let's start at the beginning. How did you grow up with money and how did that drive you to become successful?

Money is interesting because I grew up in a, a pretty well-off family, I would say. My dad was military. By the time he got out, he was a major. So we lived like military base to military base. Money didn't really factor in, right? Because we were fine. And it wasn't until my late 20s that I started to realize that money was this thing that was actually quite important in life. Because up to that point, I had just been Peter Panning my way through like my 20s. I, I have really severe ADHD. I can like point to that as being very problematic, but I just had this really hard time connecting what I do in the moment to the consequences it's going to have in the future. Right. And money, if nothing else, is like this store of value so that you can use it later. And but for somebody that just is perpetually living in the moment and doesn't realize the value of that, I didn't treat it with any kind of respect or desire even. I just was kind of just going through the motions, accruing debt, using credit cards to subsidize my lifestyle. And it was working for a long time until it didn't. And then it really, really didn't. I was probably 27. Yeah, it's 27 because I was dating this woman that I wanted to ask to marry me. And up to that point, I'd just been a dirtbag rock climber. Like, I can look back and say I was a professional rock climber, but like, that doesn't mean much. Like, I didn't have like 2 nickels to my name. And I went to her family and I sat down with her mom and dad and I asked for their permission to marry their daughter. And her mom was like this Type A super CEO type, like boss, boss lady. And she looks at me like dead in the eyes and she asks, what are you going to do to provide for our daughter? And she didn't say it with like a softball. She wasn't like, go get them, Anthony. Tell me your great answer. She was like genuinely like, Why should we let you marry our daughter? Like, who are you? I left that conversation with a chip on my shoulder for the very first time in my life. It's the very first time where society's expectation of your earning potential tied to your value as a person. And I walked away from that being like, I'm going to show you. But I didn't have like any skills at that point. Like none that were like useful. But I like, I went into my mind of like, okay, who makes money? And the first person that came to mind, no joke, Stephen King. So that next day I decided I'm going to be a science fiction fantasy author.

Perfect. Perfect. Yeah. She was like, I'm sure that was very impressive to the CEO lady.

I mean, if I could have pulled it off, she might have been, but like, so I, but I committed to that and I said for the next year I sat down every single day. I wrote 3,000 words every day, which is after a year was a million words. I published my first novel a year and a half later. But that is a slow path to building wealth and also a very uncertain one. And about a year later, my fiancée and I, she just out of the blue called it off. She was like, yeah, this isn't working for me anymore. And suddenly my author career hadn't taken off. I still had no money, was still a rock climber, and I had no idea what to do. So I had $2,000. My dad tells me, go buy a van off of Craigslist. Just live in the van for a couple of months. Get on your feet. So that's what I did. And while I was in that van, a guy came into my life and he's like, dude, this is really sad. Your life is really sad. We need to do something about this. So he, he introduced me to a different game to play with my life, which was the game of entrepreneurship. We started a window washing company and that changed everything, like everything. But it's just funny because like money up to that moment, it never factored in. It didn't matter to me until everything had fallen away. And then I realized, holy crap, you need this thing. You can't just ignore it. You can't just pretend like it doesn't matter because money doesn't solve all your problems, but it solves all your money problems. There's a lot of problems that revolve around money, and I had to learn that the hard way. Yeah.

And I wonder, I mean, being a military guy myself, you know, the military is a great leveler, right? Everyone makes— you know exactly what everybody else gets paid.

Yep.

And so it does sort of remove money from the conversation in general, right? Especially you live in base housing, like everybody has the same stuff.

Yep.

And you know, in some ways, what a cool way to grow up, right? With it not even being a factor until it comes to bite you later.

Yeah. And I think a lot of people go through that, right? Where they— people have interesting relationships with money, and I see it now having you know, over the last 12 years really evolved in my understanding of and having the opportunity to help others that are kind of going through a similar thing is that there's— you can't opt out of this game. And a lot of people think, oh, I'll just opt out and it doesn't matter. And it's like, it does matter. And God, I was— it was probably 2 years into building that business. And at that point, money still really wasn't my motivating factor in like a primal way. It was like, oh, I do need to make money. I do need to learn this game. And there's rules to this, and if I can learn it, I can do better. But it wasn't until a couple years later, our cat got sick. Like Christmas Eve, he eats something that he shouldn't. We take him to the vet, and the vet's like, yeah, we can do a surgery and save him, but it's gonna be $5,000. And at that moment, I didn't have $5,000, and he's just a cat, but like, he's this thing that I love very dearly, and I like It was our responsibility to take care of him. And so like, to then have to do the mental jiu-jitsu of like, what's the dollar value of a loved one's life? And I had to do that for this cat. And then I thought, oh my God, what if I ever have to do that for my dad or my brothers or my sisters or my partner? Like, and then it became like this, holy crap, you have an obligation to play this game better, not for yourself, but because there's people around you. Like the impact that you can have as the person who has these resources, what you can do with that to make an impact on your family and your community, like, you have a— you almost— you have a moral obligation. If we're operating within like a moral paradigm, you have a moral— like a moral prerogative to do this game as well as you can. And so that was like a big shift for me.

Yeah. And take me back to the emotion of having to make that choice, because as a cat dad, a ridiculous cat dad myself, uh, I mean, my cat brings me a ludicrous amount of joy, like outsized. And I can't imagine having to make that choice.

One side of it was feeling, this is so trivial. What a trivial thing to, to have create so much trauma in my life. This thing that we could just fix if we had that money. And then there was, there was a tremendous amount of shame associated with, I, took you into my life and I made a promise to do the best that I can by you. And I can't do that now because of this thing that I didn't take seriously before this moment. It was, it was really brutal. Um, for the listeners at home, I don't want to leave them on a sad note. We, here's the, here's the crux of entrepreneurship is that you will have to face these moments where cash is low and you have to lay somebody off or you have to have a hard conversation or You have to go hungry for a while, or like you have to, you have to find, you have to do something that you don't want to do. And what will dictate your success or failure is not your access to resources, it's your access to resourcefulness. And so my partner and I, we're sitting there like, we don't have $5,000. We could go ask everybody for money, but I was like, I'm not prepared to do that. What else can we do? And so we left, this was literally Christmas, like the day, like the day before Christmas, we're at our families and we just started calling every vet in the city and we were like, here's the situation, what can you— is there anything that we can do? And until we finally got one that was like, you know what, we can do this for $2,000 if you can get him in here in the next 3 hours. So like, we left the party, we went, got the cat, we took him over there and they were able to save him. And so like, just because somebody tells you it's going to be this, doesn't mean it has to be that. And that's a big lesson for entrepreneurship is like, don't just accept what somebody tells you and find the solution. Find an answer that does fit with what you're trying to get to. And like, we'll get to this story too, is like, I've had a big, big business failure this last year and it revolved around not doing that because I, I took my eyes off of that.

So yeah, we'll definitely put a pin in that one. Yeah. And I can't wait to get there, but Walk me through the window washing business. What was it like starting your first company?

It was so easy that I took— like, it spoiled me. It truly did. Like, it's the curse of the beginner's luck where everything just worked from the beginning because window washing is great in that there's very little overhead. We just went and bought some cleaning supplies. We didn't know what we were doing. I didn't have a clue, actually. We just started knocking on doors and talking to people and saying, hey, do you want us to wash your windows? Until some people said yes, and then we would do it. And in the meantime, I was living in my van, so I had no overhead. So the days where we would make sales, I was like, huzzah, that's awesome. And the days that we didn't, it wasn't like the end of the world for me. But over time, we started to, to hone in on like, okay, when we knock on doors and we pitch this way and we have these conversations or when we wash the windows in this way, we can, we can do better, right? What we started to realize was like we actually had a really unique advantage in the marketplace because we were rock climbers. And there's this, this middle ground of buildings that need windows washed that are too tall for a ladder, but not so big that they can justify like elaborate rigs, right? Like that you would see on a skyscraper. So we were washing these mid-sized buildings because we were really good on ropes and we could do them in a fraction of the time that other cleaners could do because we're more comfortable on the ropes. And so we'd, we'd plow through these buildings. We were like, oh yeah, we have a unique edge here. So then what we came to realize is in that business model, the hardest thing isn't the window washing. It's your, your recruiting company for good blue-collar workers, which is— we have a manufacturing company. I'll tell you, like, that's the hardest thing to hire for. But what we found was all of our friends were also rock climbers and they're all dirtbags that wanted to get paid under the table and they wanted to go on climbing trips. So they wanted flexibility. And we're like, we can be flexible if you can be dependable. Like, if we have a job and we give it to you, you get it done, we'll be flexible. And so next thing you know, our buddies are washing windows for us, and it's like, they're really good on ropes too. And so it's not a complicated skill set, which then allowed me to get out of the window washing and start focusing on the other parts that were really cool, which was like marketing and growth. And so everything just worked until like a year and a half later we had cracked a million dollars of windows washed, which was like a lot of windows. And so that, that was a good thing. But then I carried like so much hubris into the next business that I started that I didn't even realize how lucky I got on the first one, how like the pieces had just fallen together.

Yeah, I share a similar path. My, my first business was successful quickly and while that's awesome, I carried what I call the Midas touch syndrome from that business, thinking that everything that I did would end up that same way. It turns out it's a tough lesson to learn. So how did you figure out that maybe you weren't King Midas?

So the next thing that I went to do, I actually did something else and it, that also worked. So my first two things worked, the third thing didn't, and that one really didn't. I think it's more interesting than the successes for a lot of reasons, but I moved back to Minnesota. So I had been in California up to this point and I moved back to Minnesota. My friends, they had this, this climbing gym that was focused and catering towards, um, like Olympic level, national caliber competition climbers. And so actually the 2020 Tokyo Olympics, one of the two women climbers came from our gym. Like she's, she was our athlete since she was like 12. The problem was the business model was fundamentally flawed. And so I had come off these string of successes and they're like, can you help us? And I was like, well, yes, this is easy. I had no business and I got in there and I, it, I, I did not have the, the touch. I, I learned a lot of things suddenly about the hubris of believing that you have the answers, right? Or the hubris of thinking what worked over here will work over here and just saying, oh, it's an easy plug and play. And then the thing that really got me at the end was feeling as though the pressure of my friends saying, can you help us? And me saying yes, feeling like I had to figure it out on my own and wasn't open to asking for help or getting other perspectives. And so I just flew the plane straight into the ground for everybody because I was like, they relying on you. You're supposed to be the one that fixes this. And I think a lot of entrepreneurs suffer from that problem where they're like, this isn't going well, but I have to keep it to myself. I can't share it with the team. I can't outsource and get other people's perspectives because they'll think I'm weak or they'll think I'm an idiot and they won't believe in it. And then it just becomes a self-fulfilling prophecy at that point. So it's like asking for help is not weakness. It's actually requires a tremendous amount of strength, and I didn't have it at that time.

And take me back to the moment where you knew it wasn't working. Like, what, what, what's the pivot point here?

Well, for that business, we did a complete 180 of the business model we had. We were running really low on cash flow at this point, and we're like, okay, we can't maintain this, this entity as a private club. That's how it was really structured, is like this high-end premium experience for for really high-end climbers. But, um, Minneapolis is not a great demographic for that business model because we don't have a lot of rock, so we don't have a lot of people attracted to climbing. There's actually— our main competitor is here in Colorado, right? And so we were drafting off a lot of what they were doing. But fundamental problem, which is like market dynamics matter, right? Like, yeah, where's the best place to sell hot dogs? It's like outside of a stadium full of hungry people. Not in the middle of a field with nobody, which is what we had. So we opened it up, we made a pivot. We said, okay, we're going to grand open this and we're going to invite the community into the gym or sell memberships and we're going to pivot the model. But we had waited way too long for that. At that point, it was like this needed to be done 6 months prior for it to have any hope. And so we just— we made the pivot and the decision too late. It's like you're driving towards the cliff and then 100 feet from the edge, you decide we need to turn. It's like, yeah, but now you're in a skid and you're still going off. And so if anything, it's like the lesson there is you need to— when you decide to pivot matters, and the sooner is usually better.

Yeah, definitely. We have a phrase in the Navy called being behind the power curve that has been adopted in entrepreneurship. And the reality is, you know, if you realize you're too low coming into a carrier landing, and you can go engines full, you know, go into afterburner, but you're never going to catch and be able to, to rejoin the glide slope. And it puts you in a really dangerous situation. And this happens so much, right? In entrepreneurship is the best time to make cuts in a failing business were yesterday.

Yeah.

And the next best time is right now. And it's, it's really hard to recognize when you're actually behind that curve.

Totally. Yeah. We did a piece of content a couple of years ago, so going into 2020, of like, okay, we're in crisis mode. What, what do you need to do as an entrepreneur right now? Because you don't wait until you've started bleeding out. You need to make the cuts before you see the bullet coming. You're like, okay, I'm going to get hit by that. And you need to start making the cuts. You need to start having the cash reserves. You need to start making those hard decisions before they're forced upon you. Because if you wait until they're forced upon you, you're already behind that power curve, as you say. And it's like once you're behind the eight ball, You don't get in front of it. You usually, you just, you just don't.

Yeah, definitely. And what are the emotions going through your head or, you know, as you're facing that, the proverbial cliff, what's that like?

That one was really difficult because everything that I had done in my life up to that moment was really me-centered. Right? And it's one thing when you fail and it's your thing, but in that particular instance, I felt as though I had been entrusted with my friend's dream, that they recognized they didn't have the skill, the capacity to fix themselves, and that they were asking for the help. And I told them that I could, and in reality I couldn't. And that was one of the— probably the very first times in my adult life where I felt I had really let down people who loved me and were relying on me. And it was— it did a lot of damage to that friendship. Like, one of my closest friends, I was the best man at his wedding. It did a lot of damage to the relationship for a long time, not because he was angry, not because there was negativity, but because I carried so much shame that it made it very hard for me to connect again in the relationship. Because when you, when you look at somebody that you love that you feel that you've wronged or you've hurt, like, they become a mirror for you. And so every time you see them, they reflect back to you that your failure. And so you can either run towards that and stare hard in that mirror and say, I can't fight the dragons that I refuse to acknowledge, and say, I need to look at this until it no longer causes that, that pain and process it. Or you can do what most people do and what I did for a period of time, which was let me just ignore it and go this way. And like, our lives just kind of drifted apart and they've drifted back together now and we're very close many years later. But it was just self-inflicted wounds. Like there was the— there's the initial wound, right? Like as they say in Buddhism, or there's the— there's two arrows. The first arrow is the event and you don't get to decide what that is. It hurts. But the second arrow is what you decided to do about that. And I decided that I was going to take that second arrow and just like shove that in my gut for good measure. And it didn't help. Yeah, it didn't help at all.

Yeah. How do you recover from that? What does your next venture look like?

So there's, there's two aspects to that one, which is the, the relationship side that just took time. That took a lot of self-work. Like entrepreneurship, I think, is the best personal development program in the world. It's, it's great if you choose to stay in it long enough. Like you can't grow unless you grow. You are always the big constraint in the business. And so thankfully, for whatever reason, the universe put me on that path of like, learn how to grow through this process of entrepreneurship. And so that eventually brought me back to my friend and brought him to me as well. But the next endeavor was actually— it's really interesting. At that same time, my best— one of my other friends, he had another business that was also in the climbing space. This is the manufacturing company that I'm like still very involved with all these years later. And he— I don't know, like some people are just— they're just like put in your life, I think, at the right time for the right reasons. To, to teach you whatever it is that the universe wants you to know. And he was like, he brought me into his, this thing. He's like, hey, come help me with this thing. I was like, you literally just saw, like, because we were in the same building. The gym was here, the manufacturing gym business, they were not connected in any way besides that they're in the same building. I was like, you literally just saw me drive this into the ground. He's like, yeah, yeah, but let's do this thing. I was like, okay. And what that allowed me to do was actually to heal through this relationship with my other friend who had seen me go through this, didn't judge it, and also helped me realize like that it's okay. It's okay to fail. Like that's, that's just part of the game. So the next thing that I just jumped into was the manufacturing e-com. We produce like rock climbing holds, rock climbing equipment. And honestly, I probably wouldn't still be in entrepreneurship if not for my partner in that business, because he is like the most truebred entrepreneur I've ever met. Like, he's the type of guy who's just like walking down the street. You'll see a baseball glove on the side of the sidewalk and he'd be like, I bet I could sell that. And you'll just like, he'll sell it like an hour later. You're like, what the heck? He just like, He has that skill and I didn't. I wasn't really that. I was playing the game of business and it was working at times, wasn't working at others. But having exposure to him really gave me a new perspective of what it means to like fail forward and not like, as Winston Churchill says, to go from failure to failure without loss of enthusiasm. And I was like, holy crap, if he can do this, I can do this. And like, that was— it was pivotal for me at that moment.

And where are you from a financial perspective at this point? Was the gym loss devastating to you from a personal perspective?

No. From a financial perspective, I had no incentive with that one. I was really helping them. I didn't take equity or anything. I took a salary. But at that point I had— I'd sold the climbing— I'm not climbing the window washing business. I had for me at that time going— you have to understand, like when you go from living in a van with like $1,000 to you, if you'd never had more than $1,000 in the bank account, The day you have like $100,000 hit, you're like, I'm a rich man. I never have to work again. And so I left with a little bit of money from the first, that first business feeling like I don't have to do anything. I'm good, right? And so with the gym, I had no financial stake. So when it failed, I didn't lose anything, which the other side of this too is like, in hindsight, don't trust somebody with your business that doesn't have like a financial motivation. Like incentives, as Charlie Munger says, is everything. You show me the incentives, I'll show you the outcome. And my incentives, they weren't aligned enough for me to take it as seriously at that time as it needed to be. So then when I went to the next business, my partner and I, we, we came up with a good equity split there to recognize the work that he had done up to that point. And then for me coming in, like if we add growth, what slice of that do I get? And that was like, that became big money for me where I was like, holy crap, now we're, now we're no longer talking about 6 figures. Now we're talking 7 figures. And like, that's becoming, that's truly transformational for me at that point.

And what was it like coming into that amount of money? I mean, it, you know, obviously with, with van life, you've, you've learned, uh, to live, uh, quite simply. What changes for you as that, as that amount of money comes into your life?

It's interesting because everybody, I think, has a number in their mind. Like, when I hit that number, it's going to be okay. Any number above that, you stop paying attention to it. Like, we talk about money thermostats. Like, you have a baseline number that you consider normal. When you go to a steakhouse, you go to steakhouse and you're like, oh, it's a $20 steak. That's— I'll pay that every time. Some people go to steakhouse and they're like, $70 for a steak? That's way too much. Some people are like, $1,000? Sure. Right? We all have a number in all different domains of our life that we consider normal, that above that normal, above that number, it becomes uncomfortable. Below that number, you don't even think about it, right? It just becomes like, it's, yeah, whatever. Yeah, $5 for that bottle of water, easy. For me, that number really was like, for whatever reason, $100,000. Like, as soon as I passed $100,000, money no longer became like this really macro interesting thing. So from $100,000 to $1 million, it became Oh yeah, that's cool. Just another, like, more money, but like, doesn't functionally change my life because I don't— I haven't— I don't have a lot of material needs. And then when I hit a million, there was an identity shift that occurred where I was like, oh, I'm not that person that I was before. And that was like the big transformation was now thinking of myself as not the person who has accrued money, but the person who can accrue money. And that was like there's a confidence shift that comes once you realize you have the ability to make money. Then it's a skill that can't really be taken from you. And for the first time in my life, that's when I felt like nothing can ever break me financially again, because I know I can always make it back. It's interesting given everything that's happened this year.

Yeah, I, I also share that, that idea. It turns out it's hard sometimes.

Yeah.

Well, let's— you mentioned personal development. What led you to the path of personal development and how was it arising at that time in your life?

That's a good question. A lot of my personal development at that point was geared around learning tactical skills that could be deployed inside the business. How do I market? How do I, you know, deliver an amazing product or experience to a customer? So it was like very tactically driven. But a lot of that stuff requires you to deal with other people, right? Like a business really only exists in relation to another human being, your ability to deliver a value to them. And so if it's just you and the bears out in the forest, there's, there's no need for commerce to occur. There's no business. And so we ha— I learned a lot about psychology and human behavior, but in that pursuit of trying to understand human behavior for the sake of like trying to deliver something, I started to see, oh, holy crap, these are like my recurring things. These, this is my baggage. This is me. And it became very, it became more enjoyable to focus on the, the sides of personal development where it's not so definable. You can't see it. It's the soft stuff where internally you're like, oh, how can I, how can I learn to maintain poise through this conversation with an employee? Who for the third time has not delivered this thing in the way that we talked about, hasn't followed the process. I have to have this hard conversation with him. How can I not attach emotion to this? And like, slowly but surely, those little, um, opportunities for growth within the business were starting to impact me individually. But then they became like this almost like spiritual transformation which starts to occur where And we talked about this, is that there comes this point when you, you start getting really woo-woo with everything because you start to see that the whole point of all of this, like not just the business, but like this conversation, this, this life that we're living is like really in pursuit of like exploring the limits of your own capacity and potential so that you can use that in a way that makes this a better experience for everybody, right? And so I started getting really into that world of like Buddhism, of Zen, of Stoicism, and really just the philosophy associated with, um, with success, as we'll call it. Because, you know, Maslow's triangle of hierarchy of needs is like— it, it's not super accurate from a purely psychological perspective, but It's like the trajectory of truth. So it's very helpful as a model of understanding, like, once you have these base things met— your shelter, your food, your security— you can start focusing on these bigger issues of, like, meaning, of purpose. Like, what are we doing here? And, like, as I started growing through the business, like, I was spending more and more time there, which is why— and you probably experienced this too— is, like, all of the most successful people I've had relationships with over the last, like, 5, 7 years, they're, like, very philosophical. About what they do and that it's— and I think that's the highest calling for all of us is to get to that point of like, how do you deal with everything low on the triangle so you can focus up here higher?

Yes, it's sort of diving into that philosophical path. I do think, as you said, like entrepreneurship is the greatest school of personal development because it comes by necessity. But at some point you are your own limitation and the business will never grow beyond that limitation. So most of us, in my experience, start to approach it from a performance perspective. Like, how do I get better at this thing?

How do I get better so I can make more?

So I can make more. And then it does sort of over time, the deeper you go down that rabbit hole, you sort of do reach this spiritual place of like, wait a minute, it's not about me. When was that shift for you?

I don't know if there was like a singular moment that I could point to as much as just it's a gradual process. And I don't even know if I'm like fully there yet. Every day is like another level of exploring to what depth that truth is true, right? And that's actually become the more fun part because when you— some people get really excited about the deal in business, like chasing the deal, closing the deal. And I found that wore off really quickly for me. Like, it really wasn't a strong motivator. I love tracking stats. I love tracking dashboards. I love that stuff. Don't get me wrong. Like, yeah, I'm a gaming nerd, so let's run up the numbers. But like at a certain point it becomes just, it becomes really hollow. And so if you want to keep playing the game, you keep waking up every day and like, why do I choose to play this game today? Is, is the reason I came up with yesterday still true? And that got me into, that gets us into some trouble sometimes where sometimes the reason that you decided to play the game evolves, it changes. And if you're not paying attention to it, because it— every year, every 2 years, every 6 months, depends on the rate of growth, depends on what's happening in your life. Like, that ain't— the answer can change, and your identity changes with it. And so yeah, I don't know if I would say that there was ever like a definitive singular moment, as much as over time there's just been this gradual— I feel best the more time I spent in that mind space. Rather than just in the tactics, the day-to-day of the business.

Definitely. And it's definitely an evolution rather than an on-off switch. Right. And as I say often, right, the universe will continue handing us lessons until we learn the lesson and actually make the shift to implement.

What do they say? Floggings will continue until morale increases.

Yeah, exactly. Exactly. So we've put a pin in the recent stuff. Let's, let's, let's dive in. Tell me about what's been going on.

Yeah. So in 2018, you know, as, as I started making money, it's one thing to make money. It's another thing to, to know how to manage the money. What do you do with it? And so I went to my mentors in like 2014, 2015, '16 era, and I was like, okay, I got money now. What do I do with this? And they're just, they all told me invest in real estate. Like, cool. So that's what I did. I started buying triplexes, little duplexes, and little things just with my own money and house hacking them and like built up a nice little portfolio. And I was like, real estate's great. In 2019, I met my partner, a guy who I'd go on to partner with, and we formed a private equity fund and we raised about $40 million over the course of a couple of years and acquired about $100 million worth of real estate that we were vertically integrated. We managed in-house with our own team and things were going great. Things were going as fricking gangbusters. Life is wonderful until about this time last year, about almost exactly 12 months ago. I discovered it was all a lie. Effectively, my partner had just been misrepresenting everything from the financials to the operations. And it set off this cascade of events that ultimately culminated with me filing a lawsuit against him to hold him accountable for the partners and for the investors involved, but then passing everything over to new management, new ownership, and then filing a bankruptcy. And because I had personally guaranteed $40 million worth of real estate and there's a lot behind this, but effectively there was just no money left in any of the accounts for any of the assets. And they weren't, they were all bleeding cash. And so it was just, there was a 6, 7 month period there from October through about March of last year where it was just real dark days. As you both navigate the, the reality of holy crap, we have a sinking ship here, but also the feelings of betrayal. And anger. And not just anger at a person, but anger at yourself of like, how did you let this happen? How could you be so stupid? And it's so easy in hindsight to be like, here's all the things you did wrong, Anthony, obviously. At the time, it's easy to justify and put on the blinders and be like, oh no, this is that, this is okay, and this is whatever, right? And so there was just— over the last year, there was a period of time where the universe was definitely saying here are the lessons that you need to learn now, and you're going to learn them in the most, most uncomfortable way that you can. And so here we are. I'll pause there because it's a lot. Yeah.

I mean, take, take me through the emotional piece, right? I mean, here you are on top of the world. You've stacked some business successes. And, you know, just earlier you said like, hey, you know, nothing can ever affect me again. Yeah. You know, from a financial standpoint, roh roh, not necessarily the case.

The universe is like, how true is that? Let's find out.

Yeah. So, so what is it like to go from that high high to all of a sudden watching these things fall apart?

It's interesting because, you know, Diametrically opposed ideas can both be true simultaneously. You can both simultaneously know everything's going to be okay, and also to be like, everything is not okay. And from that experience, the hardest thing was, I know that there's nothing that can happen to me in life that can stop me from getting to where I ultimately want to go. I, I have that belief, but there were other people involved in these deals, other people that got hurt that don't have that ability, or they do, but they don't realize it yet. Right. And that's a different thing. Everybody has like so much potential, but especially when it comes to money and the, and people had entrusted us to do right and to take care of their money. And like, you've, you've been in that situation and you know, that's a burden that It's one thing to lose your money and say, oh, it's okay, I can get it back. I have the skills. It's another thing to lose other people's money. Lose my friends, my family, my girlfriend, my dad. Like, all of them had money with us and I had to sit down with them and be like, listen, that money's, that money's gone. It's gone, gone. It's not coming back. And that was the hardest for sure. Like bankruptcy, losing my stuff, like it, that doesn't even faze me. And we can talk a little bit about a piece of really good advice I got back in 2012 when I first started on this journey, which was it's not about what you own, it's about what you control. And that actually saved a lot of my, my bacon in this last year. That one concept, we can circle back to it, but it didn't help the people that were in those deals that lost money. and that's something that I have to, I have to own. I have to do, I have to live with that until I can somehow make that right in life for them. And that's, that's a long road.

How do you reconcile that? Where do you start?

It's interesting. I have this belief. Don't know if it's true. I have a belief that we are fragments of the infinite, of the, of the universe's desire to experience itself. and that you and I are just fragments of that. And our, our mission here is to just try to make it better. Like, we are a tool for the universe's own self-improvement. And that's a very vague thing in general, but this has been a very focusing, uh, event to say, this is how you can make it better. This is a direct way you can fix this. You can make it better in the, in the future. But in the short term, it's, it's sharing it, right? It's sharing the stories and sharing, like, not hiding and pretending like it didn't happen and, and trying to cast, um, an unrealistic expectation for others that are maybe following in similar steps and saying, hey guys, like, this is a hard path and you're probably gonna get kicked and it's gonna be okay. So like right now, just sharing this story. Is the path to fixing it in a, in a weird little way.

Yeah. So what do you wish you could go back and tell yourself, or what do you wish that people could take away from this experience that, that would have helped you?

Maybe the biggest one is there's so many lessons. The biggest one though, is you can't fight the dragons you refuse to acknowledge. If you don't go to the mirror and look into it, and you don't look at the problems— like, the problem isn't the problem, the problem is refusing to acknowledge the problem. And that's what got my partner into trouble here. Like, he's a— I don't think he did anything maliciously. I think it was a series of, of good intentions that went way off track. And at a certain point, it becomes so hard to admit that, that you just, you just take the train right off the tracks. And for my part, there are things, and, and when things go wrong, they don't go wrong in a vacuum. They don't just come out of left field. They didn't just happen like a bolt of lightning. There are a series of events and there's a series of conversations and a series of moments, pivotal moments that you could have done something. You could have noticed, you could have had a conversation. And for whatever reason, whether you were willfully blind or just choosing to be blind because it's easier than having the hard conversation and abdicating, outsourcing your confidence to somebody like that was for me. I allowed my confidence to be outsourced because it was easier for him to carry the weight rather than myself. And so when he would make a decision, I'd be like, okay, that sounds right. You sound like you know what you're talking about and you're the professional. I'm like, okay, that's just, that's abdicating responsibility in a lot of ways. I did that because I wanted it to be true. I didn't want to have to do, you know, in entrepreneurship it's so hard when you're the founder that everybody comes to you to have the answers. And sometimes what's nice about partners is you can say, hey, in these domains you have the answers, in these domains I have my answers. And I, I chose to stay in my lane and put on like the Chinese firewall and say, everything good over there? Oh yeah, yeah, everything's good. Okay. And not, not going actually over the wall to look around and be like, wait, this place is on fire, dude. What are you talking about? It's okay. Like, this isn't okay. And so you can't, you can't fight the dragons that you refuse to acknowledge. You have to look at them.

Yeah. In the Navy, we call that trust but verify.

Yep.

Right. There is a certain level of responsibility and having been in my own failed partnerships, I think where we get into trouble is if our default is to act with integrity, we assume everyone else is also going to do that.

Yep. Right.

Which is a beautiful way to— it's a beautiful lens to view the world.

It's a good way. It's a better default than the alternative.

Totally. And there's a shadow.

Yep.

And when we believe that everyone is acting with everyone else's best interest, we open ourselves up to things like this. And it sounds like there was, there were a lot of lessons here in, in that verification. And I love this concept of willful ignorance. Where do you think that came from? Was it, was it, you know, people pleasing, just trying to, to, you know, do right by, by your investors? Or where did that come from for you?

I think it was, it was actually conflict avoidance. You know, I think all the growth you could ever want in life and in your business is on the other side of a hard conversation. That could be a hard conversation with your partner, an employee, could be a hard conversation with yourself. Right. And a lot of times we don't have those hard conversations because it's easier just to go with what's happening. And for whatever reason, in other domains of life, I haven't had that same level of conflict avoidance. But with this particular partnership, I did. And I think a lot of it was because he had so much more domain experience in finance and in real estate than I did. And I was more of the marketing investor relations arm. And so it became very easy to say like, okay, let's not make a fight out of this. He obviously knows what he's talking about over here. Default to that because I wanted to avoid the conflict and maintain the status quo. That's something I can't go back and redo it. And I don't know exactly like in those moments what I would have done differently knowing what I know now. But I know that, that those were the pivot moment. Pivot points, so to speak.

What strikes me is it takes a tremendous amount of courage to look yourself in the mirror and say, damn, this was me. I was being conflict avoidant. Yeah, I wasn't the cause of the problem. I wasn't the first arrow. Yep. But I certainly made it worse by not acknowledging the actual situation. How do you forgive yourself?

Forgiveness is a really interesting concept. You, you shared a book, um, When Things Fall Apart by—

is it Pema? Yeah.

And forgiveness is simultaneously one of the easiest things to talk about, like, conceptually, but an entirely different thing practically. And it's what I'm working on right now is forgiving my partner, forgiving. And that, that's not to say condoning. That's not saying like I'm letting you off the hook, or just— it's saying I understand you, I'm not going to let this affect me and consume me. And it's a whole other level than to look at yourself and say, how do I forgive myself? And a lot of people is interesting is like a lot of us as like Type A entrepreneur hard chargers won't even stop to contemplate that question of like, how do I forgive myself? A lot of guys won't do that. And it's— I don't have an answer. Like, it's, it's a process every day of like recognizing intentions matter, actions matter, that you can do everything right and you can still lose. That's not weakness, that's life. That's a Star Trek quote. And And, and at the end of the day, like, all you can do is the best that you can do. And the, and the thing is, like, okay, did I do the best that I could do? No, I could have done better. Can I change that now? No, but I can change how I go forward. And so it's not letting go of the past as much as taking the lessons that serve you and moving forward stronger because of it and not letting the dead weight from that hold you back. Because there comes this point of, like, the self-flagellation, the blaming, the guilt. It doesn't serve you. It doesn't help you. And if it doesn't help you up the mountain, you need to let it go. If my goal is to, you know, make things right someday for investors and help them, like, in the way that I can, I can't do that if I'm also trying to lug up all of this excess baggage that in a lot of cases is self-induced, right? Because, like, it's easier for me. It's easier for me to forgive my partner in a lot of ways than it was to forgive myself. In the same way, one of the things that like really broke me up is when I told investors last— it was probably last November that I really started to like— I brought in some third parties to like take a look at things and be like, I think some things are weird here. And I started sharing that with investors. And the thing that like really was the hardest thing for me to accept was their understanding. They were so much more understanding than I was of myself and forgiving. And it was actually like, it was the only time during that entire period that I ever like cried. It was, it wasn't the, the bad thing that was happening. It was the nice thing that the people that were getting hurt were saying. About it. And like, I guess the lesson there, if there is one, is just forgiving yourself is the hardest part.

Yeah, but yeah, what a beautiful reflection. And yeah, it sounds like you had some amazing people investing in your project.

Oh yeah. I mean, we only let the most amazing of people into the deals. I mean, you know, this too is like the, the money you don't take is more important than the money you do. Right? Like you don't take the wrong people's money. Um, you want to work with people that you want to work with. And for the most part, like, I think what makes this experience so difficult, and you've had bad part— you had partnerships that have gone awry, is like, you don't let this turn you off to that. As I've had nothing but great partnerships in every other domain than this. Right? And so, but I'm not going to let this— doesn't define what moves forward.

Yeah. I mean, you have two options, right? You can, you can close your heart and never trust anyone again, or you can open yourself more fully and say, this really hurt and I'm willing to do that again. I'm willing to go through that pain.

Yeah. Yeah. Because like one of the, one of the things that you probably got this question frequently when you're, you're working with investors, like as you're raising capital, one of the big questions people ask is like, Give me an example of a time something went wrong and how'd you react? What'd you do? Like all that stuff. And like people give like the soundbites and whatnot. Right. But like, this is, it's, this is the reality of entrepreneurship. And I hope by sharing the story that others don't have to experience it on the same level that I have, but they will experience it. They will experience the employee who they trusted and they stole, they stole from you. They will experience it with the partner who. Things just go south real quick, right? You will experience it. It doesn't mean you're doing anything wrong. You're navigating the best that you can with the information that you have and the skills that you have at the time. Right. And just know that the water is going to be choppy and sometimes the boat will sink, but just have like faith and confidence that you have the ability to swim back to shore, build another boat and keep going. Because like the alternative is that you just What, you're gonna spend the rest of your life like on that secluded little island and never, you know, set sail for brighter shores? Like, it's not an option for a certain type of person. And if you're listening to this, you're probably one of those types of people.

I love that. So on the backside of this experience and in totality, what does wealth mean to you now?

Wealth has always been a much more holistic approach rather than— because money again is just a tool, and money is a terrible way to keep score. It's the easiest way to keep score, but it's a terrible way to keep score because it's just a tool. It's a store of value. And so what, like, what's your goal? Is it just to accumulate as much value as you can, like Smaug the Dragon, and like hoard it? No, it's to bring those resources in so that you can do amazing things with those resources out in the world, and you can, you can have an impact. And so if, if money is not a tool for increasing your impact in the world, whether that's for your family so you can spend more time with your kids or your, your wife, or spend more time working on yourself, or spend more time in the gym, or spend more time pushing yourself in the mountains, or push your— spend more time with your community and giving back, like, then you're, you're, you're, you're playing the wrong game. You're running up the wrong scoreboard. And so wealth is like, for me, is the desire to accumulate as much as I possibly can. Not talking about money necessarily, but experiences, skills, competency, capacity so that I can go out and like turn that back out, fill your cup so you can dump that out and like fill everybody else's cups. Like that's what wealth is. And the ability to do that on a day-to-day basis on the timeline in the ways that you want that motivates you the most, like doesn't get better than that. If you get to wake up every day and choose what you work on, that has like meaning and purpose and impact on the world, you're winning. You're winning regardless of how much money is in the bank.

I feel that. Yeah. And now that you have that definition of wealth, what would you go back and tell the dirtbag climber living in a van?

He had it right. No, no, no. So it's interesting because as I accumulated more financial resources, my life took on more and more shades of the same life that I had when I was in my 20s. I love, like, my girlfriend and I, we spent a month and a half this summer in a van traveling through the mountains, being a dirtbag. I, it's, it was, it was the right external environment. Like the materials didn't matter, but what I was missing was at that time I was so self-focused. I didn't have skills. I didn't have any value to offer to the world. I was just going along. I was just a leaf on the river and just being pulled along. But I didn't have any agency. I didn't have the ability to make an impact. And so now it's like, oh, I love being a dirtbag, living in a van out in the world. But what if I can do that and simultaneously have impact in the world? That's beautiful. That's what I'm after. But I didn't— what do they say? Like Jordan Peterson talks about how It's not virtue if you can't defend yourself, right? Like, it— to choose to not inflict violence is not virtue if you don't have the ability to inflict violence. So a bunny rabbit doesn't have virtue for the fact that he's passive. He just can't do anything, right? In the same way, it wasn't virtuous of me just Peter Panning and not actually giving anything back to the universe.

I was just—

I was just sponging it. I was taking it. And now it's like, oh, I can live that life, but I need to be the sponge that's consistently being like wrung out and poured back into the world. And so that's— I would tell him, I go back to that dirtbag and be like, keep doing this, but you need to get better. Not for you, for the world, for the people around you. And you don't see it right now, but like someday it's going to become the most important thing and the only thing that you care about. So you might as well start now.

I love that. It's a, it's a beautiful reflection, right? It's like what I'm hearing is that you had it right from a material perspective.

Yeah.

But from an inner wealth perspective, there was something missing. Yeah. And it sounds like you've done a whole lot in order to create and cultivate that inner wealth. What is— what does impact look like for you now?

So much of the world, I think, is— I think the main thing that limits people is themselves standing in the way. I believe everybody has a seed of greatness in their heart, and the only thing that stops that seed from blossoming is them standing in the way of their own light. And so if we can help people realize two things— one, you do have that seed, and two, all you have to do is get out of the way of your own light and let it shine— like, amazing things happen. And so, so much of what we do now when we talk about helping people maximize their return on life or helping people step into their greatness is because if, if we can help you step into your greatness, then the downstream impact that you have that I can have as an extension of that is just, it's, it's otherworldly, right? And I, I, I, I believe entrepreneurs are world changers. Like they, they have an idea, they manifest it, they make it reality. And if it's a good idea, it makes the world a better place and people are better served for it. And so anything that we can do that helps other people, and right now that looks like just sharing the story, right? Literally just like impact looks like sharing your story of the times that were good and the times that were bad. Because the times that were bad, somebody's going to go through that and they're going to realize, okay, somebody else went through this, I can get through this. Because like, one of the— dude, I can't tell you, like, one of the craziest things is when all this was happening in the last year, all of the people that I reached out to that are like a similar or higher level of success, you know, with big air quotes, they're all like, dude, I've been— I went through something similar. Not exactly, right? Like, history doesn't repeat itself, but it always rhymes. And they're all like, I've been through something similar. You're going to come out the other side better. But what I realized was I had never heard those people share those stories. A lot of people shared things behind closed doors that I had never heard outside of it. And I was like, I wish I had known that. And so Impact Now is like, let's share those stories of the wins and the losses. So that other people don't feel so alone because it's a hard journey. Like the best personal development program in the world, but it's, it's fricking hard.

Yeah. And it really is, I think, important that, that people know that because it can be very lonely.

Mm-hmm.

Well, Anthony, I, I really appreciate you being on. I'm excited. To spend the weekend doing some outdoor things. It's going to be maybe diving into some more stories here, but I just really want to thank you for, for sharing because it's so easy to put up that veneer of success and what you shared isn't easy.

I appreciate it, man. I hope if anybody is like going through something like they, that they don't just consume this information, but if they need help, that they ask for it, that they reach out, that if anybody's listening to this and they, they want a conversation, just slide in my DMs or something. Cause like anybody that's got, and you, you know this too, is like anybody that's gone through the darkness is like all too willing to turn around and shine a light. Like, just let me know if you're back there too in the tunnel, like happy to help.

Cool, man. Where can people find you?

Uh, find me on Instagram, @theanthonyvacino. Just shoot me a DM over there. Like, start a conversation. Don't be a lurker. Don't be weird. Social media. Be social.

Cool. I love it. Well, thanks for, uh, coming on. Appreciate you.

Thanks, dude.