MBA1305 Q&A Wednesday: Should I attend a mastermind retreat that costs $5K?
2 Feb 2026 · 10 min
Hubie is deciding whether to spend $5,000 on an entrepreneurial mastermind retreat. Omar walks through the decision: who else is going, what's the total cost with travel, could you get the same value cheaper, and what's the ROI from access to people and expertise. The real payoff is the relationships you actually follow up on afterward.
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If you have a question you want to ask, just email me over@omarr.net Today's question is from Hubie and Hubie asks, I have the opportunity to attend an intimate entrepreneurial mastermind retreat. The people that will be attending are high caliber and it seems like it's going to be a lot of fun, but the price tag is 5000DOL. Any advice on how to make a decision on whether to attend or not would be greatly appreciated. Thanks Hubie. Great question, Hubie. Because often we have opportunities to go to events, go to masterminds, go to retreats like these. Then we look at the ticket price and we're like, whoa, how is this so expensive? Why is it so expensive? The good news is that you do recognize some value to this retreat. So in today's lesson, I'm going to try to give you a framework to make this decision. This will help you to decide whether to attend not only this retreat, but any other experience or event. So let's get into it. Let's get down to business. So Hubie asks, should he spend 5k for this mastermind retreat that he's been invited to? Before I get into sharing a matrix, a framework of making a decision on something like this, I want to mention that I've attended some several mastermind type of retreats with a small number of entrepreneurs. And I've had really good experiences and I've had bad ones, too. And it all boils down to one thing, who's going to be there. That's the bottom line. These retreats are really designed for you to get to know and connect with people that you can really learn from, people that can really inspire you, people that you just want to get to know as friends. And if those connections are not worth it for you, the people there are just not people that you're interested in connecting with, then it's just not worth it. So I highly recommend you have a general understanding of who's gonna go, who's gonna be there, what other entrepreneurs are attending. The retreats that I've been to that were really beneficial were the ones where I was surrounded with entrepreneurs that I admired, that I wanted to learn from, that are in a position that I wanna be in very soon, that are also just good people. So I just want to start off with that. That really makes the experience. The people you share it with, the venue. It's a plus. You know, if it's a nice, exotic place or you're doing some fun activity like diving or snowboarding or whatever it is. But it's really about the people. And in my opinion, don't pin your hopes on, you know, one or two people that are going to be there. Like, you might be saying, hey, the person that's organizing this thing is somebody I really want to get to know. Maybe one other person, but I'm not sure about everybody else. I would try to at least have, you know, four to five people that are going that you really want to get to know on a deep level. Why? Because the organizer is going to be busy and you're pinning your hopes to get to know one or two people. What if they're occupied? What if they're busy getting to know other people? What if it just doesn't gel? Maybe you don't have a chemistry as, you know, as friends. So it's always good to have, you know, some numbers, you know, not pinning your hopes and spending all this money and, you know, obviously spending this time and, you know, more money to get there and all that kind of stuff. Having, you know, more people you're interested in getting to know, the better. Okay, so let's talk about the money. Okay, it's $5,000. It's not an insignificant amount of money. There's lots you can do with that $5,000. To help yourself as well as help your business. This is a business expense. You are improving yourself as an entrepreneur, as a leader. This is a work trip, right? Yeah. It's going to be fun, and it's going to be maybe at a nice location. But this is not really, you know, R and R. This is not friends and family trip kind of thing. You're gonna have your business brain on, right? So you gotta see this as a business transaction. And when we have a number like $5,000, we have to think, what are the opportunity costs? Like, what other things can I do with that $5,000? If I just gave you $5,000 right now to spend on your business and it wasn't going to be spent on this retreat, what would it be? You might think, oh, I can spend it on Facebook ads. I can spend it on maybe hiring a freelancer to work on a project to improve my business. I need some office equipment, whatever it is. Right. Think about the things that you can do with that money. Now, I'm just using the number 5k. But you also have to include the other costs involved. You know, your travel costs, if you have to pay for your accommodations, things like that. Right. So the total cost of this trip. So if that equals, you know, $8,000 after everything is said and done, then look at that. What can you do with that amount of cash in your business? This is important because you're going to be comparing the benefit you're going to get from this retreat versus the benefit you can get by spending it on something else. Now, I'm the first to tell you that, you know, money is relative. You know, $5,000 to one company may sound like a huge amount for another that's making, you know, $100 million in profit every year. It doesn't seem like a huge expense. So how much does that burn really matters? How much does that actually weigh in your own business really does matter. If you lost $5,000 right now, how much would it affect your business, your growth? That's something you need to consider as well. If you parted ways with that money and it was an unsuccessful trip, how much regret? How much trouble would your business be in? If there's any sense of risk of like, wow, my business is going to go down or my business is not going to do as well, or I could really use that money to do something essential in my business, I would not do this. I would not go to the retreat, because obviously this is not disposable income you can spend. Yes, it's a business trip. Yes, it's something that will help you in some way, even if it's not a total disaster, you know, but if it's that tight, I would not. Next, I want you to list down what you really want to achieve by going to this retreat. I want you to put aside any kind of like personal enjoyment or fun or things like that. That's a bonus. That's great. But. But business wise, what are you looking to achieve? Build relationships with people, maybe partner with them, maybe do some business together, maybe learn from them, maybe have a chance to follow up later on and continue to learn. And a good way to kind of put a number on these things is like, you know, some of these people are consultants. Some of these people that might be on this business trip or on this retreat charge by the hour for their advice. Maybe like $2,000 an hour. So if you can, you know, get to know them, become friends, and getting on a call with them is no big deal, and they're happy to help you out with no charge, then that's a pretty good return on investment. You know, being able to do that. Don't rely on that because they could charge you and that's their right. But even just at the retreat, you might have some discussions that are going to be worth gold. But the thing about this is that you don't know for sure. This is why I'm saying that. Make sure that you can part with this money comfortably. Now another thing I want you to consider is, can you reproduce this experience to some level for less money? If these people are super hard to access, if these people are not going to be together in the same space ever at a conference or at a dinner or something like that, then it's going to be hard to reproduce. But for many situations, you know, if not all, some of the people that will be attending this retreat, this event might be going to a major event in your market space. And what if you bought the most expensive ticket at that event Instead of spending 5k for this mastermind, you spent a thousand or even 1500 and got like the VVV VIP ticket, right? And got to have dinner with them three times during the event and had like a private Q and A. You know how these like event tickets include all this, like intimate time with the speakers? So yeah, this is another alternative. Think about how you can actually reproduce this experience for less money. If it's a stretch and it's hard to do, then make sure you write that down. Make sure that you actually come to that conclusion. Now giving you some sort of framework to work with. I want to kind of give you a conclusion of my own experiences. When the people are great, when the people are there that you want to be around, that you want to kind of aspire to and maybe be in their same position soon, that makes a big difference. And a lot of times it's worth the money if it doesn't burn too much, if it is something that you can part ways with. I'd recommend actually speaking to somebody who has attended this event before, if it's not the first time they've done it and get their perspective. Was it worth it? Did you enjoy it? What did you get out of it? What are their biggest takeaways? This will give you a clear understanding of the ROI you're going to get at this retreat.
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To wrap up today's Q and A, Wednesday's question from Eubie. You gotta weigh it out and see what return on investment you're gonna get. You gotta see this as a business transaction. Look at the opportunity costs, what else? You can spend that. Then you guys just make it a clinical business decision. I know we're inclined to kind of be like, hey, this is gonna be fun. This is gonna be great. I'm gonna feel great. Try to put that aside for a moment and see if it's worth it for your business. Now having said that, I want to mention that if you don't get out, if you don't make relationships, if you work from home, if you're an online rat and you're just on the Internet, totally. And you don't have real life experiences or real life relationships with other entrepreneurs on a regular basis, whether they're conferences or meetups, then your need for this might be a little bit higher than others. So consider that in your decision. This is why I mentioned can you reproduce this in another setting in a meetup and an event? Another thing to consider is that maybe you can go to three or four events that are less expensive and have more consistency if they give you a return on investment. Thanks so much for listening to the $100 NBA show hit subscribe right now so you don't miss a beat by hitting subscribe on whatever you use to listen to podcasts, whether it's Spotify, Stitcher Radio, Apple Podcasts, Overcast, you never miss an episode. As soon as it's available, it gets downloaded right to your device. Before I go, I want to leave you with this in person connections are super valuable. I've known and met people online for years, and then when I meet them in person, it just solidifies things. It's like we become really deep friends really quickly. There's nothing like that real connection in real life. But I also want to mention that if you make a connection, if you actually meet somebody in real life and you have a good time together, you have a good experience, capitalize on it and make sure you're consistent with it. Speak to them on the phone, email them, and try to see them in real life again in the near future. Relationships need nurture. Can't just neglect them once you've made an investment. Thank you so much for listening and I'll check you in tomorrow's episode. I'll see you then. Take care.
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