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A
When you manage procurement for multiple facilities, every order matters. But when it's for a hospital system, they matter even more. Grainger gets it and knows there's no time for managing multiple suppliers and no room for shipping delays. That's why Grainger offers millions of products in fast, dependable delivery so you can keep your facility stocked, safe, and running smoothly. Call 1-800-GRAINGER Click grainger.com or just stop by Granger for the ones who get it done. You're listening to the Travis Makes Money podcast presented by GoHighLevel.com for a free 30 day trial of the best all in one digital marketing software tool on the planet, just go to gohighlevel.com travis. What's going on, everybody? Welcome back to the Travis Makes Money podcast, where it's our mission to help you make some more money on this episode. My producer is here in studio. What's up, Eric?
B
Kenny Rogers once said, you gotta know when to hold them and you gotta know when to fold them. And I want to talk about that today here on the Charles. Next time. Why are you laughing? That was a good intro.
A
Okay, maybe I don't know what you're introing yet, so.
B
Well, I want to talk about poker. When are you gonna be serious? Are we gonna. We're gonna fool around. I'm sick of you fooling around on these. I want to talk about when you should say yes to something, when you should say no to something on your entrepreneurial journey.
A
Okay.
B
Because we talked about today recording. We talked about in and out, saying no to doing deliveries. We talked about Miles Teller saying yes to a big, fat, juicy exit from a company. And I want to talk a little bit about, you know, when you should say yes, when you should say no, that sort of thing. Okay. What's a time that saying yes to something that seemed like a good opportunity has cost you an immense amount of money or peace of mind?
A
Probably a couple of the businesses that I've started that I felt were great moves at the time. And it's hard to say I regret it because I don't, because I learned a ton of stuff from it. And it, you know, it's that old trope, like I wouldn't be the person that I am today if I didn't have these failures in my past. But also it's true. So it's a kind of a cliche for a reason. So there's been a couple different things like that where I've just started something and then like three months in, basically was like why did I do this? I did not have to say yes to this thing. And it just brought in a ton more stress and anxiety for not a lot of reward. And then it was like, I'm not even. I'm not fully taking advantage of the thing that's working right now, and I'm distracting myself with all these other things because they sound fun and cool, but that's sort of the. The entrepreneurial, you know, struggle is the shiny object syndrome, which I've always had. So there's been several of those on
B
the say yes to side of things. Have you ever been in a period where you feel like you've said yes to absolutely everything?
A
Yes.
B
Do you regret doing that? Do you recommend people. Do you recommend people ever have a period like that where they say yes to absolutely everything? What made you stop doing that?
A
Yeah, there was definitely a period, because what happens is, like, when you're first getting started, you. All you want is opportunity. So I. I was like an opportunity hunter, and I was. I was looking for opportunity. And then you start building a little bit success or a little bit of notoriety or a little bit of confirmation that you're capable of doing things well, then opportunities start coming to you a lot more frequently and a lot more often. And then some of them seemingly are really good opportunities. So for a little while, I was just like, yeah, let's do that. Sure. Yeah, let's partner on this thing. Let's do this thing. Let's do that thing. And I started looking at. It's like, man, I got, like, six irons in the fire and all, and five of them are distracting me from, like, the core thing that I should really be focusing on. And so eventually I had to basically be like, I gotta stop saying yes to all of these things. Even when it's. Even. Even when the opportunity seems to be a really good opportunity, it's. It's still required. It requires more discipline at that point to be able to be like, no and then not have a reason for it. I think that was what got me to say yes to everything before was just like, why would I say no to this? Like, there's no reason to say no to it other than the fact that I've already said yes to this other thing. And so I didn't have. Since I couldn't really articulate a great reason as to why I was turning it down, I would just say yes. In retrospect, what I've learned more recently is that you don't have to have a reason. You don't have to try to justify the decision. You just have to basically just say, no, it's not a good time, you know, and.
B
Right.
A
And be okay and be comfortable with that. Just you. You don't feel like you have to justify your nose, you know what I mean? You can just say no.
B
Yeah, let's talk about. Let's talk. There's so many jokes. A little time. Let's talk about. So the flip side of this. People say yes to everything. There's also people who say no, and it hurts them in the long term. I don't know if you know anybody like this. So let's talk about people who, you know, think about the context of deals. Knowing when to leave something, knowing when to quit. You know, there's a lot of people who stay way past their prime or their business's prime or an opportunity's prime because they're so scared of, like, what if it gets bigger again? Or what if I don't wait till the perfect moment? I'm going to try to time this. What do you kind of weigh out when you're. Well, first of all, do you know of anybody like that? Like, how many stories have you talked to people where they go, like, they held on too long?
A
A lot of those people, like, the first problem that I described is probably less common than this problem. I would say that most people have difficulty letting go and moving on to something. My struggle has always been the dead opposite of that. Like, I. I have sometimes I. I have struggled historically with sticking with one thing long enough to be able to get the result.
B
Yeah.
A
When I start, when I. When I stop, like, feeling super interested in the thing, I'll just. I'll just. It's really hard for me just to be like, just gotta keep going. Just gotta keep going. Just gotta keep going. If I don't really enjoy it at all, or if I've seen behind the curtain, that's been. That's been probably more detrimental to my ability to stick with things than anything else is, like, behind the curtain and seeing sort of how. How the sausage is made and then being like, I actually don't really like a lot about this industry, or I don't like some of the people that operate in this world. And I don't want to become like them, nor do I want to hang out with them, nor do I want to do business with them. So I'm just gonna go do something completely different. My mistake probably was that I always did something completely different. Like, I wouldn't just be like, hey, I don't like, you know, I don't like the way that the, whatever the coaching industry works. So instead of just being coach and being okay with that because there are good ones, I would just be like some. Follow the noise. Bloomberg follows the money. Because behind every headline is a bottom line. Whether it's the funds fueling AI or crypto's trillion dollar swings. There's a money side to every story. And when you see the money side, you understand what others miss. Get the money side of the story. Subscribe now@bloomberg.com like screw that whole thing. I'm gonna go start a software company.
B
Yeah.
A
And it's like what? These are two, like these are not adjacent at all. And now I just have to go learn a brand new thing and search some of the skills transfer over. But not all of them do. And there's other skills that I'm not even aware of that I have to develop into this world. So you. I sort of maybe started at the starting line too often rather than starting on the 20 yard line. And instead. So there's been a couple things like, but I would say by and large, probably most people struggle with the, with what you just said versus what I struggle with, which is that they, they tend to stick in things too long and are not nimble enough or flexible enough to see writing on the wall or, or just to like they, they, they have their head buried in the sand about the truth. And, and sometimes the truth is going to hurt. The whole thing about the truth will set you free, but first it'll piss you off and you're not willing to see the truth. Meaning that like you, maybe, maybe you're doing good like the company that you started or something, but it's in a shrinking market. So you're, you're fighting like economic trends in order to stay in this thing because you started it 12 years ago and it's all, you know, so I just, I just got to keep doing this and, and we just got to adjust our strategy and it's like, sure, yeah, and there's some things that you could probably do, but if the entire market is just getting smaller and smaller and smaller and smaller because of the economy or because of, you know, AI or because of this new technological advance, you know, like if you're in print magazines, you know what I mean? Like, probably just not a great space to be in even if you feel like you're doing good work. But it's like, oh, our revenue shrinking. It's like, yeah, because the total market is shrinking. Like that's just not a good place to be spending all your time and energy. You know, it's like 10, 10 out of 10 skill set. You might have a 10 out of 10 skill set, but you're in a 4 out of 10 opportunity, like a 4 out of 10 vehicle. So it's like, well, can you make it work? Yeah, ish. You know, or you could just pivot and pick a different segment of a market that's adjacent to that one and try to learn more about that one and be in a growing market and learn how to do it from this perspective instead of this old school thing that's no longer working. So I think people, like I said, turn a blind eye to the truth too often because they know that it. They don't want to accept it as truth. They just want to be like, well, I heard. I heard, you know, from whoever, Kobe Bryant, that you should never quit. And so I'm not a quitter. You know, like, mom didn't raise no quitter, so I'm just gonna stick in this thing. It's like, okay, but it's not like it's. It's not. You're not quitting the game.
B
Yeah.
A
You know what I'm saying? Like, there's a difference between just taking yourself off the court and benching yourself versus just pivoting and you're still in the game. It's not. You're not quitting. You're just moving directions. And that is that good entrepreneurs do is they see the writing on the wall, they understand the truth of the situation, and then take that information and make a new decision and then move in that direction. And then if they run against that same obstacle or similar or different obstacle, then they move in a different direction. You know what I mean? So it's not that it, like there's. There's a. The hustle culture has vilified all forms of quitting and then made it seem like if you quit this exact path that you started down, then you are now a quitter. And it's like, well, that is just not true. It just means that there might be success in a different path for you. You know, I just had this girl on the show who was trying to be an actress when she was younger and she got a. Landed a role in a movie, and she did a couple Broadway things and did a couple TV shows, but just, like, things weren't clicking, you know, and then she got recruited to do this one infomercial when, like, the infomercial stuff was first starting to come on the Scene like early days, you know, a couple decades ago. And, and she crushed. And then all of a sudden, another company wanted her to do an infomercial for them. And then she got tied into this, like into QVC and all these online shopping things. And now she sold like two and a half billion dollars of products on national television. It was like, it's acting adjacent. It's like, of like, if you would have, if you would ask her, she'd probably be like, of course, I would rather have the career of Julia Roberts or whatever. But also she's made a fantastic living for herself and has. And now one of the, one of the products that she was selling on TV basically was a company that was, wasn't going downhill. It just was kind of stagnant. And the guy who owned the company was like, hey, if you take this TV spot and you sell X number of units, I'll give you the company. Like, you can, you can have it, basically. And so she did that. And then now she owns this company that sold, you know, hundreds of millions of dollars on national TV spots. And she was the main spokesperson for it. So it's just like she still gets to do the thing. She still gets to go to these high production places and be on national television and be the talent in the room. And like, all the things that she really wanted to do, it just wasn't exactly in the vehicle that she wanted it to be in, but also, like, you know what I'm saying? Like, it's not, it's not. You can't look at this pivot as a failure in life. It's just more like this was the available opportunity. I actually figured out that I kind of enjoyed doing this. And I get paid really, really good money and get to provide this amazing life for my family doing it this way. And that's, that does not mean that I quit. That just means I chose a different path along the way. After I got enough feedback to tell me that this was something that wasn't going to work in the exact way that I wanted it to work.
B
Well, especially in realms where, like, you want to be a serious actor. And then it's like I'm doing an infomercial, but it's like, again, you're weighing out what's the actual win? Like, is this a win? Is this just something I didn't expect it to be? I actually interviewed someone. Her name's Sarah Priebus and she's, she's an actress and she had a story she shared on one of my shows years ago. What year was this? Three years ago. Oh, God. So long ago. But she. She kind of shared a story that followed a slightly similar path. But I'll play it really quick because I think it's interesting.
A
Could not believe this was a real product. There's nothing better than feeling clean and confident. But are you really as clean as you should be? Not unless you've taken care of a very personal area that requires special attention. Now there's a solution. It's my shiny hiney to easily access that difficult to reach spot.
C
You know, I shot this thing. I did. It was like, no one's ever going to see it. It's whatever. Then six months later, the producer from the infomercial texts me a link to the Ellen show from that day. And, like, she and Kristen Bell are literally showing my infomercial, talking smack about it. You got to create your own opportunities, really, in this industry. So much so I wrote on Ellen's Facebook wall, you know, you guys might be making fun of me, but my butt's been cleaner than all of yours for months now, or whatever I wrote. Sure enough, the next day, I got a call from a producer over there. They're like, we don't know how this happened, but somehow turn into shiny. Honey, we. We want to fly you out here. And, yeah, amazing experience.
B
It's like something that works.
A
Like, any week on Ellen, you could
B
be like, oh, this. My career is over. Yeah, this is ruined me. Or you can be like, let me
A
own this and find the silver lining in the situation. Yeah. Yeah. But I do think, is it. No, that was a different person. I'm trying to. I'm blanking on the name of this author who wrote a book on quitting.
B
Oh, yeah, I saw it today on
A
Jordan Harbinger's show
B
is in the book.
A
I'm thinking Angela Duckworth.
B
Annie Duke.
A
Annie Duke.
B
I have a little free library by my house, and I was perusing it, and that book was in there.
A
Really?
B
And I literally was like, oh, we should talk about that.
A
Yeah. No, I did not. Full disclosure to not read the book. But I've read. Listened to probably two or three of her interviews when she was doing the press tour, and I think she's got a really great framework for deciding when you should, you know, like. Like Kevin o' Leary says on Shark Tank, you know, he's just sometimes like, hey, look, man, sometimes you just got to take an idea behind the barn and shoot it. Because you see some of these guys on Shark Tank that are just. They're like, Seven years invested into this thing. They've leveraged their home. They're $20 million in debt. Yeah. And they've sold nothing. And it's like I, I understand the idea of just like, I'm not gonna quit, I'm not gonna quit, I'm not gonna quit. But also sometimes you should. And it's not again, to me quitting, like actually quitting means that you just like give up on all forms of your dream, like all forms of entrepreneurship or all forms of acting or all forms of. And you're going to go do this soul sucking desk job that you hate. Like that to me is more of like what quitting looks like. But even that could be for a period of time. It's like, okay, so you have this company that you're a half million dollars in debt on. You've leveraged your home and you, and you're not selling any units and you're been pushed to the point of exhaustion and it's destroying your life essentially. You know, you, you have those types of situations. Well, maybe for a few months you do go back to the soul sucking job that you hate so that you can get back into a good financial position and, and start feeling some momentum and creating some wins in your life and then you get back out and, and get back onto the court and start playing again. You know what I mean? Like, it does not mean that you have, that you're a quitter. I guess what I'm trying to say, it's just sometimes hard to know the difference between those because then you have the stories of like, you know, the pursuit of happiness type where Will Smith famously portrayed that the guy who bought all this, all this equipment and couldn't sell it and then, but then worked hard enough to be able to sell some of it and then became, you know, multimillionaire on Wall street type of a thing. When, when after he was in living in bathrooms and sleeping in, in bathrooms like a homeless person with his son. You know what I mean? So there's some of the, you see some of those stories and you go like, I just, I just, I can't quit, I can't quit. I can't quit. It's like, well that I think we have two different definitions of, of the word quit there. You know, pivoting does not mean that you're quitting. It just means that you're collecting feedback and using that feedback to make a decision that is more likely to bring you the result that you ultimately wanted to get when you started this venture in the first place.
B
Yeah. One last thing on the, on the nos. Sometimes a no is a not yet. Have you ever felt like you missed out on a major opportunity because you hesitated too long or waited too long to think about it?
A
Yes.
B
Solar. Here comes a solar story.
A
Oh, that, that's actually, that's the one
B
I thought you were going to say is not jumping a solar center.
A
Yeah, I was not thinking about that one. But that is, that isn't, that is one for sure. There's been a couple things like that where I've just like maybe that'd be kind of cool. But then I just didn't, I just didn't do it or like that one in particular though I feel, I feel fine about it at this point just because I'm just like I, I just didn't know what I didn't know at that time. It wasn't even something that was in my mind. Like I did not, when, when I was in my life I was not thinking like I could start a solar company and then I chose to do something else. It was just like it was not even on the radar, not even in my brain to think about being like the owner of a solar company, negotiating my own deal with a distributor and things like that. Which if I had done that at that time or had that mindset at that time, it, you know, could have gone very well for me. But I just wasn't thinking like that. I was thinking like a commission sales guy. So I was just like, who can pay me good commissions and I don't have to worry about six week turnaround times on solar installations, whatever. But, but there's been more, there's been other things like, like just different interviews that I've had for the show that I've, that I've, they were like, hey, you know, this person's a high profile person and they'll do an interview if you buy, you know, X number of copies of their book for their book launch or they just launched this product. So you know, buy a bulk order of this thing and we'll give you this interview. And at the time I balked at it and was just kind of like, ah, I don't know if I want to do it like that or, or you know, I, or I don't have the money, you know, frankly to do it. So I sat on the sidelines and watched the opportunity pass me by and then later realized that it was like, oh my gosh, like this was not that much money and could have been a great like, like value add for them, a good, supportive thing for me to do. I would have gotten that interview, like, six years ago that I'm still. That I still have not been able to land organically since then. And then if I tried to pay them now, it'd probably be five times what they would have charged back then to do this bulk buy of their book or whatever. So there's been. There's been a few things like that, which is one of the reasons we ended doing this dinner party shoot with Shaq, because I was just like, I just want to. I'm going to fully take advantage of this opportunity that's in front of me because I have no idea if or when it's ever going to come back around. So try to learn from those things. And then also just weigh it out from the perspective of, like, the death bread, that deathbed regret thing of, like, will I regret not doing this? And if the answer. If the answer is yes, I will regret not doing this, then I feel like I owe it to myself to do it and just figure it out.
B
Don't eat the death bread. You'll regret that.
A
I don't recommend it.
B
Okay, I'm gonna have you. I'm gonna give you some this or that. I want you to tell me what you think. Okay. Would you rather have a big brand or big bank account? And here comes the question, how big is a big bank account?
A
That's a very relevant question. It's a very relevant question.
B
Let's say tomorrow you can wake up with a million dollars in your bank account or a million dedicated followers to your podcast.
A
Million million followers to the podcast.
B
Okay. Would you rather have slow stable money or one giant payday? How big is the giant payday and
A
how big is the slow stable money?
B
Slow stable money or one giant payday? I'll put it this way. No, I won't put it that way, because that'll change the answer.
A
I typically would take the big payout.
B
If you won the lottery, would you be the monthly payments or just pull up?
A
Okay, yeah.
B
Would you rather have full control over a company or just have less control but get the big investor checks again?
A
Sort of depends on the company. Like, do I want. Do I like it if I don't? If I don't. If not, if I'm not a big fan. I just like the numbers. Then it's just like, I would rather just cut a check and then get some reports. But if I really like what the company's doing, I'd be like, okay, yeah, I'd love to be involved in this on a regular basis.
B
Would you rather have a smaller business you love or a bigger business that you kind of hate?
A
A smaller business I love.
B
Would you rather say no and sleep really well or say yes, add a little bit more stress, but be a
A
lot richer for the sake of this game? I will say I'll say no, but it depends. It would really depend on what that situation, again, because, like, again, stress is going to come with all forms of self improvement to some degree. Like any. Any. Any type. You're. Anytime you're taking a big swing or there's a big risk on the table, it's obviously going to come with some increased stress, increased anxiety, but I'm okay with that depending on if I really. If I really want to take advantage of that opportunity or not. But, like, again, for the sake of this game and just saying, like, would I rather have peace of mind and say no or more stress and anxiety with a little bit more money, then I would. I would typically say no and just keep things simple.
B
Fair enough. All right, well, go ahead and let's say no to making this episode longer than it needs to be, huh?
A
Yeah. And one more time, it was Annie Duke. Annie Duke. Yeah. That's. Yeah. If you enjoyed this conversation. You want to go deeper on some of these things and you're thinking about you're maybe in a position like this right now, which I know a lot of people are in the weird economic times that we're in, then go pick up a copy of Annie Duke's book, and I'm sure you will get a lot from that.
B
I started her book, but I quit halfway through.
A
Well, that's it for this episode of the show. Remember, money only solves your money problems, but it's easier to solve the rest of your problems with money in the bank. So let's start there here on the Travis Makes Money podcast. Thanks for tuning in. Catch you guys next time. Peace.
Podcast: Travis Makes Money
Episode: CO-HOST | Make Money by Knowing When to Say Yes (and When to Walk Away)
Host: Travis Chappell; Co-host/Producer: Eric
Date: May 2, 2026
This episode centers on a crucial success skill: discerning when to say yes to new opportunities and when to walk away. Travis and Eric dig deep into personal failures, the cultural stigma around quitting, opportunity costs, and the emotional intelligence required to make pivotal decisions in entrepreneurship and life. They share candid stories, reference expert perspectives, and offer actionable frameworks for listeners wanting to make smarter, braver money moves.
The “Yes to Everything” Trap
Transitioning from Opportunity Hunter to Gatekeeper
Knowing When to Fold
Emotional Barriers to Quitting
Infomercial Success (14:10-15:30)
The Shiny Hiney Story [13:34 - 14:32]
On Justifying Saying No:
On Opportunity Overload:
On Stubbornness vs. Strategic Pivoting:
On Handling Embarrassment as Opportunity:
On Regret and Opportunity Cost: