Chance Sweat: The Bet Before The Bet

We pull a thread through three standout stories and lay out the hidden work that happens before a big risk pays off. We argue that smart bets come from pre-framing reality, auditing your own fear, and validating with real-world tests instead of vibes.  
• shifting the show format and introducing “the bet before the bet”  
• Justin Maxwell’s COVID SPY decision and why it was a framework, not a guess  
• how compound experience creates conviction under pressure  
• Bobby Davidowitz catching a “safe” plan that is really fear  
• Brody’s lesson on pre-selling and validating before you build  
• why you don’t have to burn your boats to prove commitment  
• managing downside and regulating emotions like a long poker game  
• golden handcuffs as money, community, and identity  
• the “time in the desert” and why hustle beats standing still  
You should go check it out the full episodes! 

ABOUT PERSONAL BETS

Person Bets is a podcast for the people actually running the business, not the investors, not the board, not the consultants on the sideline. Hosted by Chance Sweat, business broker at FitzGibbon Alexander, Inc. and founder of Sweat Equity Advisors. 

🔗 Personal Site: chancesweat.com
🔗 Brokerage Site: fitzgibbonalexander.com

🔗 Coaching Site: sweatequityadvisors.com
🔗 Follow Chance: @itschancesweat

Transcript

New Format And A New Thread

SPEAKER_02 0:00

Hey guys, happy Friday. It is Chance Sweat, business broker with Fitzgibbon Alexander, owner of Foundry Leadership, and we are back with a new episode of Personal Bets, but new style this week as we shift into the new format. Every other week, you're gonna be getting a new interview from one of my esteemed guests. And then every other week, so in those off weeks of the interviews, you're gonna get me in this beautiful mug. This week, I got something interesting I want to do. I want to go through and talk about the bet before the bet. So gonna pull out some clips from some of our best podcasts so far, the ones that have performed the best, also the ones I've gotten the most text messages and calls about, and go through and try to unpack and pull at a certain thread. So I feel like every mainstream narrative that you hear about an entrepreneur and entrepreneurship, it always seems like there's this big jump, right? They quit, they have this big epiphany of an idea, um, someone fires them, right? Or they just decide to burn the boats and go all in. And that might happen, right? That definitely is something that we've seen and we've heard about. It happened with me, right? I lost my job, and then, you know, I thankfully have been working towards, I guess that's a kind of a good point. I was already working towards my real estate license in order to become a business broker after selling my business. So for me, it wasn't as big of a jump. But you hear about it a ton in mainstream medium media where someone just goes all in, they commit, and that's it. But I feel like across the three guests I'm gonna talk about today, it's kind of a different pattern that starts to show up, right? They seem to validate before they leap, or at least they check themselves before they leap. And they kind of do a self-audit or assessment. So, um, and and they've really only gone all in once they've kind of done this pre-work. So I feel like that's something that I really want to tease

Justin’s COVID SPY All In Bet

SPEAKER_02 1:55

out here today. So let's start here with one of my best friends, Justin Maxwell, Mr. Money Maxwell, and I want to talk about his COVID spy bet. That's COVID as in COVID-19. SPY is an SPY, the SP 500 ETF index. So let's talk about how he made that same bet on Google.

SPEAKER_01 2:14

Because, like, either we're going to all die in a nuclear fallout, whatever it's called. See, that's what school gets you. Um, whatever that's called, or we're gonna live and they're gonna overreact. So I was like, hey, if zombies are really coming, I mean, we are washing our fruit and vegetables with Clorox wipes, so like maybe they are coming. But I was like, I'm just gonna make the same bet that I made on Google. I'm just gonna make it on SPY, the SP 500, the largest 500 companies in the United States. So I'm not gonna tell you the amount of money that I put into SPY, I don't think that's relevant, just doesn't matter. But the amount of money that I put in was all of my savings again. I'm like, hey, if the top 500 companies of America go out of business, you got a bigger problem. Money's not gonna be a problem. And within um, I think it was seven or eight months, we had a V bottom recovery, and every all the experts said there's no such thing as a V-bottom recovery. There's never a V bottom recovery, there'll never be a V bottom recovery. There was a V-bottom recovery, and I made double my salary from that one bet in the stock market than I ever made working this, I would say 40 hours, but it's more like 60 hours a week that I was I was in all the stress. I was like, I don't need lab corp anymore when I have the stock market, when I have other passive income streams. Because the thing about money, and it's it's horrible to say, but when you get money, it's so much easier to make more money. You get so many more opportunities. You pay to get into rooms that you normally wouldn't pay to. And a lot of people can't understand this. And like, hey, I don't, I can't pay my bills, and I understand, but if you can start cutting out certain expenses and you can start buying assets that build you more assets, like SP 500 or whatever it is, like business loans, whatever, you can start building the passive income that everybody wants. They might want a lake house like this one day, and that's how you can be here on a random, I don't even know what day it is, Tuesday, a random Tuesday, and it's Tuesday. Yeah, you can be here on a random Tuesday and say, hey, somebody wants to be on a podcast. You want to be on a podcast? Sure.

SPEAKER_02 4:15

So let's unpack this. This is COVID-19. The stock market is in the absolute crapper. It is down, down, down, lock limit down every single day. And Justin had previously made a bet back in college where he took his entire life savings, which, you know, in terms of the time was a lot of money for him. But for someone else, you know, five, six thousand dollars may not be a ton of money. It's a ton of money to me right now, right? It's a ton of money to a lot of people, especially in this economy. But Justin had been this, been through this before. He took a calculated bet on Google and he figured, what's there to lose, right? But this experience gave him something different that other people wouldn't have had at the time. He looked around and he saw the irrationality, uh, if that's even a word, of everyone in the market. There was so much fear and uncertainty and doubt. But then he was looking at this and he was thinking, if the top 500 companies in America, in the world, really, we should say the world, right? It really is a global index. Apple is everywhere, Google is almost everywhere, right? There's certain countries that don't allow Google and YouTube and whatnot. And he said, if all these companies go to zero, I've got bigger problems than my retirement account. At the time, he still had his job. And so he took his entire life savings, which even though he's one of my best friends, I don't know how much that was, but I I know it was a lot of money. And he put it in the market. He bought the 500 largest companies in the US in the world by buying the SP 500 index. And I guess it I wouldn't call it a YOLO, right? But people on Wall Street Bets would probably call it a YOLO and win all in. And I think why this worked for him, one was because everyone was panicking and there, you know, people were wearing. Do you guys remember watching those videos of the people in the grocery stores and they were wearing like the big plastic boxes and the fish tanks on their heads and like anyway. But the reason that it works is that Justin didn't bet on this blindly, right? He had been in the market, he had had exposure to it before, he had a safe job, and he had this pre-framing that removed not all the fear, right? I mean, you're putting all your money in the stock market, that's kind of scary, but it removed some of the fear. And he just thought to himself, right? If this goes to zero, well, then none of us are gonna have money, so I haven't lost anything, right? I'm still on a level playing field. And there was that mental structure that let him hold when everyone else panicked because he didn't buy in at the bottom, and you never buy in at the bottom, right? And I don't think this was reckless. I think it was a framework that he had built, and whether or not he recognizes as a framework, it was a framework. And he built this and built this and built this over his years of exposure in the market. And he kind of talks about that compound uh experience, right? And I think compound experience is so, so important.

Compound Experience Beats Panic

SPEAKER_02 7:06

So next up, I I want to talk about Bobby because he had this idea that no one's gonna come to save me, right? And I think Justin didn't say this explicitly, but no one was gonna come save him in the market, right? He he he was betting on the Tim Cooks and you know all the the big CEOs of these Fortune 500 companies, but none of them were specifically coming out to save him. He was making a bet that would potentially save himself. But I want I want I want you to hear this from Bobby and what his mindset was where he caught himself rationalizing

Bobby’s Brutal Self Honesty Moment

SPEAKER_02 7:46

where he didn't need to be.

SPEAKER_00 7:47

I read and then I reached out to some professors that I had, and I was really just like hoping for a lifeline. And I think that this is where the placing the bet on yourself when when I realized like nobody's coming to save you. You know, I was talking to people and I was trying to figure it out and I was freaking out, but at the end of the day, nobody was coming to save me. I had to figure this thing out, like what I was gonna do. So um, in that process, I really thought about getting my master's, but I realized that it was a cop out. Like I was just scared. And and if I would have gone back to school, I would it would have just purely been because I didn't have the balls to figure out what I really wanted to do. So uh funny enough, I I wasn't working for a little bit. I was living with my mother, and the first job I had after college, after graduating with a 4.0, was being a bar back at a club. Like that's the first thing that I did. And the other thing I had a big fear of that I, you know, business to me sounded boring. Like, no, like I said, nobody really taught me about business. All I knew is that my dad never talked about his job, and my mom never seemed excited about working. So it just seemed like this that sucks, right? And then like my dad used to go by Bob, and I'm like, dude, I'm gonna be some guy 40-50 years old in a cubicle named Bob, like miserable, you know, like, and so everything in my mind was not even thinking business world. Um, and then you know.

SPEAKER_02 9:09

So I love that he caught himself because if he wouldn't have, Bobby might be Bob sitting in a cubicle in his 40s right now. And there's nothing wrong with that, right? People are really good at their job. And we've heard from Jimmy, we've heard from Bobby, we've heard from other people on this podcast that don't see themselves necessarily as an entrepreneur, but they see themselves as an entrepreneur, right? They were at the right place at the right time, they had the right experience, they got in and they looked at their company and the business and they said, This is what I'm gonna do, and this is how I'm gonna fix it, and this is what I'm gonna build within a pre-existing structure. I did this in my corporate job, right? I built teams, I built new systems and processes, and I I loved and I I I fed on that, right? But no one was gonna come save me in my corporate job. No one was gonna come save Bobby when he was making this decision. He could have stayed happy and safe with his friends and you know, girlfriend, I think at the time, and went and got his master's degree, but it it it wasn't what he wanted to do, right? There was something inside of him that was telling him that this wasn't where he was meant to be. He, you know, is a super personable person. He needed to get out of there. And so when he caught himself mid-rationalization about trying to make a safe move, he realized that I gotta have some brutal self-honesty here, name the fear, and then realize that I gotta get out of this. I gotta move on, I gotta, I gotta do whatever's next, I gotta keep moving. And that was the first bet, right? He put a chip on the table, and that's all it took, right? But it happened before any external move. Next up, we we gotta go back to

Brody’s Rule: Pre Sell First

SPEAKER_02 10:50

Brody. We had such an amazing conversation, and I I'm not gonna give any prep for this one, I just want you guys to listen to this.

SPEAKER_03 10:56

They were kind of like getting a lot of funding and getting off the ground, and he had worked on a couple other startups, and he had moved to Jacksonville, where I lived at the time, from like Silicon Valley area, and he sat down and heard my idea, and he was like, You're building the app before you build the business, like you have it backwards. So his advice was don't build an app, build maybe a website first, but more importantly, just focus on getting the jobs, getting the contracts, and actually making money in the business. He was really telling, like, kind of teaching me like a crucial lesson at the time, which was pre-sell the thing and actually validate the business model before you sink all this money and time in, and maybe you're wrong. And so I had heard that and I hadn't it hadn't really sunk in like what does that mean and what do I do about it yet? But a couple months later, in the Facebook group that we had all these chefs in, we started hearing about these little projects. Like, hey, we need seven chefs here, we need ten chefs here, we need 20 chefs here, and we're like, what if we became kind of the the arbiter of that? So the model basically started to evolve to maybe we're gonna be a staffing company instead of a private chef placement company. And then all of a sudden we heard about this giant government contract actually on like uh I forget, I think it was in Indiana, if I remember remember right, where they basically needed um, they had all these Afghan refugees that were like on the base, and they needed all these chefs to come basically serve them food. Um, and so we realized, okay, there's an opportunity for us to bid on this and maybe win this big contract worth a lot of money and really get ourselves started. And we basically failed to get that contract because there's a lot of stuff that we didn't have in place. But a week later, we heard about another contract up at Northwestern University in Chicago where they basically like did not require all that stuff. There's a lot of like government contracting stuff we didn't have in place, so we were like, hey, I don't think we were wrong with the thinking, we just weren't ready for this contract. So let's see if we can get this. And we actually did get that one. And so all of a sudden it was like the models changed, but we have this huge contract worth a few hundred thousand dollars over the course of like the next rest of the semester. And if we can just deliver on that and figure that out, then we can really get this started and go find other contracts from there.

SPEAKER_02 13:18

This is so good because so many people, I see it with so many of my friends who want to become entrepreneurs or they have an idea, they want to quit their corporate job, they think, Well, I gotta build the YouTube channel first. Oh, I I gotta start um, you know, I gotta build my business cards first, I gotta buy the website domain. You're looking at a guy who owns 15 different website domains for ideas he's had over the last five years that he's never executed on. Just putting that out there, okay? Sometimes you just have to go. You just have to do it, right? And I think, you know, he says it here, right? The the most the most quotable thing from from Bobby is that you you're doing it backwards, right? You gotta pre-sell here. So what what am I trying to get at, right? What's the what's what should I take away from these three uh geniuses?

Pre Frame Then Audit Then Validate

SPEAKER_02 14:10

And the first thing is you gotta pre-frame what's going on. You gotta sit down, look at the landscape, and map it out. And it this doesn't have to be some super complex thing. It can be as simple as Justin looking around saying, people are wiping down their groceries with Clorox wipes. There's an incredible amount of fear in the market right now. And for an option trader, an option seller, that's what really matters to him. But then you have to do the internal audit, right? Am I seeing this fear in the market because I want it to be in the market? Am I seeing this opportunity in the market because I want there to be opportunity for this idea that I've already built up in my head? Or am I not going to take this next step because I'm telling myself I can't do it, right? Even when reality, you probably can. So you got to do that internal audit, right? Bobby did this when he looked around and said, Hey, I'm gonna go back and get my master's, and really it's just because I'm scared. And you can't. I mean, the some fear is good, right? Some fear is very good. I would say a fear of heights, which I have, is very good because it keeps me away from edges that could be otherwise dangerous. But sometimes fear holds you back. And then you have to validate it, right? You gotta you've done that pre-framing, you've looked at the landscape in front of you, you've done your internal audit. Am I seeing things the way that I'm seeing them because I'm afraid of them or because I want to see them that way? And that's important. And then you have to validate it, right? This is where I go to my friends and I ask them, hey, I have this idea, what's your thoughts? And you know, of those 15 website domains I I own, Justin, my wife, and my wife and other friends have told me on so many of them, hey, it's a cool domain name, but that's not what you need to be focusing on. And so they sit in my GoDaddy cart and we move on. But the you don't have to burn your boats to prove your commitment. The real burn happens as you go through the process, right? For me, my burning of the boats was really kind of just drilling holes in the bottom of them. As we got closer, and I looked at all the signs on my landscape, and I realized this probably isn't gonna be the place for me. And then I got the validation when I got a call weeks before my actual termination saying, Hey, I don't think I have a spot for you on the team. Start looking. What was I supposed to do? I sped up my plans that I had already been working on, which originally were just gonna be a side hustle and a slow transition out. Instead, I've got to get moving, I've got to get my license, I've got to get you know qualified with a qualifying broker. I need to move up my timeline and built the business around that. If I had started six months sooner on building a YouTube channel and a newsletter and everything else, I don't know if it would have helped me. I really don't. I don't think it would have. Right. I'm doing that now because it's fun and creative and it's a creative outlet, but it it wouldn't have helped me in the moment.

Big Bets Need Emotional Control

SPEAKER_02 17:13

So let's go back to Justin's uh podcast for just one minute. I'm not gonna roll a clip, but I want to talk about later in the episode, he talks about making a very sizable bet on Facebook. And I think at the time it was so called Facebook, it was recently gonna be changed to Meta or had changed to Meta. But Justin and I are in New York City, we're there for a trading uh show or walking around New York City, we're on the Brooklyn Bridge, and he looks at his brokerage on his phone, the app on his phone, and sees he's down fifty thousand dollars and he just held. So many people, so many people would sell, thinking, all right, we're going to zero. I've got to get out of this trade right this minute. And he's put his phone back in his pocket and kept on walking. Why? Because he hadn't bet his whole life on this one, right? He knew the landscape he was in, he had done the self-assessment, he realized that the fear and uncertainty in Meta wasn't like the COVID. It wasn't like his conviction with Google. So he made a sizable bet, but not something that would cause him to lose the proverbial house. And he still had a W 2 at that time. Or he might have just left his W 2, if I remember correctly. So, you know, there was some fear there, but he knew what the floor was, right? It can only go to zero. And then he still would have money on the other side. So the lesson there is, you know, sometimes you got to push all your chips in, but you don't always have to push all your chips in. There's nothing more that I hate than when I'm playing poker with friends, and you got that one person at the table on every single hand, they go all in. That person never wins. Sometimes they double up, triple up, but they never win because they can't regulate their emotions to get through the game. And that's what's important here. You see this with Justin, you've seen this with Bobby, you've seen it with Brody. They regulate their emotions, they make smart bets. Sometimes they're losers. Sometimes you lose on a hand, sometimes you lose on a trade, right? Sometimes you lose on an investment. Sometimes you lose on an idea, right? But you're still in the game. And then I want to talk about the idea of golden handcuffs

Golden Handcuffs And Identity Loss

SPEAKER_02 19:15

here. Because we see this, I think, in two examples. We see this in Justin's example, and we see it in Brody's example. But, you know, Brody said I he was almost in one of those spots where he has the he has these golden handcuffs, right? Uh, and he's not doing anything because what he has right then is too good. And if you don't realize that, you don't do that pre-framing and then validate your feelings or invalidate your feelings, you can get locked in for a long time. Would I have been happier the last year if I had jumped out of corporate America sooner and became a business broker and started my consulting company? Hell yes. Last year sucked. Every bit of a reorganization in a corporate company sucks. Right. And the problem was I had these golden handcuffs on. I had a very large, sizable check come in every single week. I had quarterly bonuses that I was hitting. And outside of that, all my friends were there, right? It's been almost a decade at this company, and I really built my entire life and persona around it. When I left that job, I was mourning, not because of the money I lost or the opportunity I lost, because well, that was gone, but it was the person that I had built, the persona I had built my life around that company. Those are my golden handcuffs, right? All the friends that I thought I had are still working at that company. Well, plenty of them have left since then, but still working at that company. And I don't get to talk to them all the time because I'm not online with them. And we're not actually, you know, as great a friend as we thought, because the version of me that they were friends with died at that company. So that's so important to realize that you have to continually look at the scans landscape, look at the cards on the table, and keep validating or invalidating how you feel about it, and then decide whether or not it's time to make a move.

The Desert Season And Hustle

SPEAKER_02 21:10

So Brody also brought up this great example about the time in the desert. And you know, off camera, Justin and I talked about this as well. And you see this in Bobby's story, right? When he gets out of college, when he's trying to figure out who he wants to be and who he's supposed to be, right? Because sometimes those aren't the same people. And that time in the desert, it sucks. And I I know this is supposed to be a very upbeat idea of a podcast, but I I want to say that sometimes you have to go through this suffering, this crushing in order to come out the other side built into a new person. You've got to be refined into who it is that you're supposed to be. And for me, it was this idea of doing everything right, being super successful in sales, building a career out of it, building teams, hitting metrics, and then just to get kicked out the Door. And I truly believe that that was a God-inspired event because I I don't think I ever would have left. I think this will always have been such a side hustle thing that I never would have had the guts and the courage to jump out. And I'm learning from these guys and these people I talk to all the time with their businesses, both for the podcast and not for the podcast, people who are looking to sell, people who are looking to buy, that if you're not constantly doing this process of pre-framing where you're at, validating or invalidating it, and then testing the waters, right? Um, if you're not validating that and doing the internal audit, then you're gonna you're gonna stay where you're at. There's actually a great clip. Um, I'm gonna I'm gonna see if I can put it in here. It's from Casey Neistat. He made a movie based on a Twitter uh post, and I'm gonna put it right here. One second. Here we go. I found the clip. It's called Life Explained in 27 Seconds. So for those listening, Casey's walking on one of those automated walkways in like an airport. Life is like going the wrong way on a moving sidewalk. Walk and you stay put, stand still, and you go backwards. To get ahead, you have to hustle. And then he starts running on the moving sidewalk. And this was inspired by the Fairley brothers. He put this movie out almost 11 years ago. It's got 11 million views. That is insane. But you gotta hustle, right? You gotta hustle. So, with all that said, what I want to say is that you have to identify the questions that you're not asking yourself, right? Maybe I'm better working within a system, right? And being an entrepreneur. I would say that I'm kind of both. Actually, I'll take that back. I'm definitely an entrepreneur, right? I did well in corporate America because there was overarching systems in place. I did really well uh when we owned the Pep Boutique because the business was already there. I purchased something that was already existing, and I just came in and created the systems alongside my wife that allowed us to grow it and exit. And, you know, in business brokerage, the brokerage already exists. I work for a fantastic brokerage, Fitzgibbon Alexander, amazing human beings, amazing business brokers. The system's already there, the license stuff is already there, the training's already there. I just have to come in and execute and make it my own. Now, my consulting business, that's completely new to me. Had to learn that on the fly, but I'm embedded within my clients' businesses, and I can take the systems I know and apply it there. So definitely more of an entrepreneur. So maybe it's asking that question, you know, am I better to do this or do that? Look at the landscape that's in front of you, right? Identify things that are holding you back, and then validate whether or not those and inter um and what's the word I'm looking for? You know, validate that internal audit that you have to do. And then I you gotta

Stress Tests And A Simple Call To Act

SPEAKER_02 24:56

run the stress tests, right? You gotta look at all the options that are available to you, find your cop-outs, eliminate them, and then just start to build, right? Just do something. I made a video this week on YouTube. You should go check it out. It's stupid. I was gonna make a video about what it looks like to do a remote closing, and it was gonna be an unlisted YouTube video. It was gonna be out there for my uh, I was gonna send it via email to my buyers and sellers before closing day, especially if they have a remote selling, on what the day looks like. It was gonna be a very simple day in the life vlog, and I was gonna walk them through all the steps and things they can or cannot expect. And instead, I got a phone call from my wife that we might have a rat in our house. And you should go watch the YouTube video because it's kind of funny. My wife's Italian, she drops the F-bomb a ton. And I made the video because I just kept filming throughout the day and it was fun, right? And so I'm building something there that probably becomes nothing, right? And maybe my YouTube channel just becomes educational content for buyers and sellers and those trying to grow their sales teams. But it was fun, right? And it wasn't a cop out because I kept myself working. So anyway, I hope you guys have a great uh week. I'm excited to come back with a new guest next week. I hope you enjoyed this version of the podcast. Go back and listen if you can, if you want, to the podcast with Justin Maxwell. He's building an amazing coaching business for those that are interested in taking their finances into their own hands when it comes to investing. Bobby Davidowitz, I mean, the commercial broker king of Orlando. I'm gonna give him that title right now because he's growing into it. An amazing team with Alliance at EXP. He's got a culture center that's about to open, a one-of-a-kind place. And Brody's just buying up every small service business in Central Florida. This guy is just doing amazing work. I I love these guys. I love being held accountable by these guys. You should go watch their podcast. You're gonna learn a ton from them, and that's it. That's the thought.