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What is your Entrepreneurial Appetite? · Business Brain – The Entrepreneurs’ Podcast

• 0:00
  Dave Hamilton: Business Brain, episode 744 for Wednesday, April 15th.
• 0:06
  Dave Hamilton: It's tax day, folks. 2026. Oh, man.
• 0:11
  Dave Hamilton: Sorry.
• 0:13
  Shannon Jean: Dang it.
• 0:15
  Dave Hamilton: There's other cute things I could have come up with.
• 0:18
  Shannon Jean: That's true. It's tax day.
• 0:19
  Dave Hamilton: It's tax day.
• 0:20
  Shannon Jean: It's just fact. It's one of the two facts of life, right?
• 0:26
  Shannon Jean: That's good.
• 0:29
  Shannon Jean: It doesn't seem.
• 0:37
  Dave Hamilton: Greetings and welcome to Business Brain, the show where we take a few things,
• 0:41
  Dave Hamilton: we crunch them, we dissect them, we use them to tune our business brains and
• 0:46
  Dave Hamilton: keep on living our charmed lives.
• 0:48
  Dave Hamilton: Our sponsors for this episode include one new one and one returning one.
• 0:53
  Dave Hamilton: Our new one is WhatNot.com slash sell, where you can go and for a limited time,
• 1:00
  Dave Hamilton: WhatNot will match your first $150 sold in your first month.
• 1:04
  Dave Hamilton: So love that. and nerdwallet.com slash brain where you can learn about fundera
• 1:10
  Dave Hamilton: from nerd wallet a free and easy to use platform that lets you compare real
• 1:14
  Dave Hamilton: financing offers from trusted lenders and you can talk with a real person nerdwallet.com
• 1:19
  Dave Hamilton: slash brain we'll talk more about those in a little bit for now here in durham
• 1:22
  Dave Hamilton: new hampshire i'm dave hamilton.
• 1:25
  Shannon Jean: And I'm out here in Northern California still. I'm Shannon Jean,
• 1:28
  Shannon Jean: and I'm stoked to be here.
• 1:30
  Dave Hamilton: I'm glad you're stoked to be here. I'm stoked to be here, too.
• 1:33
  Shannon Jean: I love talking about this stuff, man.
• 1:35
  Dave Hamilton: Me, too. And a topic that I've had on the list for a little while is something
• 1:40
  Dave Hamilton: I have learned by experience. I was going to say the hard way,
• 1:45
  Dave Hamilton: and that is true, but I've also learned it the positive way.
• 1:50
  Dave Hamilton: Okay. And when we were looking to sell our first business that we had together that we were selling,
• 1:59
  Dave Hamilton: Deals on the Web, we were not actually looking to sell it. I should point that out.
• 2:06
  Shannon Jean: That's the best time to sell.
• 2:07
  Dave Hamilton: Which is another lesson, right?
• 2:10
  Shannon Jean: Yes.
• 2:11
  Dave Hamilton: It's like, I don't want to sell now. It's making a lot of money.
• 2:13
  Dave Hamilton: That's when you want to sell because that's when people want to buy.
• 2:16
  Dave Hamilton: And sure enough somebody showed up and i i still believe that it was it was
• 2:21
  Dave Hamilton: alan meckler it was he was running jupiter media at the time he had had meckler
• 2:24
  Dave Hamilton: media and internet.com and all the things,
• 2:27
  Dave Hamilton: and uh and uh they were they you know we went through the whole due diligence process they
• 2:32
  Dave Hamilton: approached us they're like we're doing a thing we might want to acquire and
• 2:36
  Dave Hamilton: they were a company that acquired they they acquired they grew by
• 2:39
  Dave Hamilton: acquiring things all the time made perfect sense it
• 2:41
  Dave Hamilton: all looked good the deal wound up falling apart as
• 2:44
  Dave Hamilton: falling apart as we've talked about on the show here uh just
• 2:48
  Dave Hamilton: be and and their stated reason which seemed legit and
• 2:51
  Dave Hamilton: i firmly believe was true is that they had an
• 2:53
  Dave Hamilton: opportunity to acquire something much much larger which turned out
• 2:56
  Dave Hamilton: to be media bistro uh and they needed all their cash to do that and so you know
• 3:01
  Dave Hamilton: dave and shannon were left hanging heartbroken heartbroken because that deal
• 3:07
  Dave Hamilton: fell apart we had a 21 day period from when the contracts were signed to when
• 3:13
  Dave Hamilton: the deal needed to commence.
• 3:16
  Dave Hamilton: And it was on day like 19 that it died.
• 3:20
  Dave Hamilton: All legit part of the deal. But.
• 3:25
  Dave Hamilton: It killed that business, not because the business was in trouble.
• 3:29
  Dave Hamilton: The business was thriving. It was because we had checked out.
• 3:33
  Dave Hamilton: And we had, in order to check back in, we had gotten committed to the sale, right?
• 3:39
  Dave Hamilton: So in order to check back in, we would have had to really double back down.
• 3:45
  Dave Hamilton: And we just didn't have a reason to, other than to keep the business going, right?
• 3:50
  Dave Hamilton: But we had decided we weren't going to stick around with the business,
• 3:54
  Dave Hamilton: right? It wasn't like some two-year transition period.
• 3:56
  Dave Hamilton: It was going to be maybe a two-month transition period.
• 3:59
  Shannon Jean: And we had owned it for 10 years. It had done really well for us.
• 4:02
  Shannon Jean: We just were kind of, someone else was running it. We had an operator.
• 4:05
  Shannon Jean: And it would have required a massive amount of energy to step back in to kind of boost it up again.
• 4:10
  Dave Hamilton: To boost it back up again. Right.
• 4:12
  Shannon Jean: Yeah.
• 4:13
  Dave Hamilton: And so we did not. We opted not to.
• 4:17
  Dave Hamilton: And we just kind of let it ride. And it made some money for a little while sort
• 4:20
  Dave Hamilton: of on autopilot as those kinds of things do. And then and then it stopped making
• 4:24
  Dave Hamilton: money for, you know, and that's just how it was.
• 4:26
  Dave Hamilton: And that was a decision at that point. That was the decision we made explicitly.
• 4:31
  Dave Hamilton: But the process of getting to it was at no point did we say,
• 4:37
  Dave Hamilton: you know, if this deal doesn't work, what are we going to do?
• 4:39
  Dave Hamilton: We didn't ask the question.
• 4:40
  Dave Hamilton: And we've had this conversation here on the show.
• 4:43
  Dave Hamilton: I had a similar scenario, let's say, last year. It doesn't really matter.
• 4:48
  Dave Hamilton: I guess last year would be the right thing.
• 4:50
  Dave Hamilton: We were looking at selling one of the other companies, not me and Shannon,
• 4:53
  Dave Hamilton: different group partners, selling one of the companies we had.
• 4:58
  Dave Hamilton: And the buyer,
• 5:00
  Dave Hamilton: Was, you know, we started putting things together and the buyer wanted a period
• 5:06
  Dave Hamilton: of time to really evaluate things.
• 5:08
  Dave Hamilton: And they offered the deal that I'm going to always look for in the future.
• 5:15
  Dave Hamilton: It was their idea because they wanted to do right by us.
• 5:19
  Dave Hamilton: They said, look, we were here, but we're our company's kind of in a weird spot.
• 5:25
  Dave Hamilton: So we want to learn more. Really, I think maybe the way to summarize it,
• 5:29
  Dave Hamilton: I don't know if this is entirely accurate, but it doesn't matter.
• 5:31
  Dave Hamilton: For the sake of this story, it might as well be.
• 5:33
  Dave Hamilton: Okay. The CEO was not the only partner in the business.
• 5:38
  Dave Hamilton: He was very aware of how we worked together because we were partners on like
• 5:42
  Dave Hamilton: they were a vendor of ours, which is a great type of business to find to sell
• 5:47
  Dave Hamilton: to because they know your business.
• 5:49
  Dave Hamilton: His partners did not know us, and I think they wanted some more time to learn
• 5:55
  Dave Hamilton: and be like, is this really the right thing for us?
• 5:58
  Dave Hamilton: He was like, dude, dude, let's buy it now. Let's buy it now. and um
• 6:02
  Dave Hamilton: so he they offered they
• 6:05
  Dave Hamilton: said look what we're gonna do is during that
• 6:09
  Dave Hamilton: that three months we're gonna pay for
• 6:12
  Dave Hamilton: a part of the the growth of the business that that they were gonna kind of that
• 6:17
  Dave Hamilton: they could have brought to the table anyway like as part of the the the new
• 6:22
  Dave Hamilton: like the new ownership structure right like once they acquired it you know everybody
• 6:26
  Dave Hamilton: finds a a synergy like with They had a thing that if they applied it to our business,
• 6:31
  Dave Hamilton: it would have, you know, would have done well.
• 6:35
  Dave Hamilton: Right. And that was their theory. And it was like, well, if I can share this
• 6:37
  Dave Hamilton: to my partners, then then the sale will happen.
• 6:40
  Dave Hamilton: And we did prove it out that the sale wound up not happening by no fault of ours.
• 6:45
  Dave Hamilton: Their business had, like I said, had been going through some changes and those
• 6:48
  Dave Hamilton: changes sort of amplified beyond a point where anyone had predicted.
• 6:52
  Dave Hamilton: What he said was, I want to do this and here's the deal.
• 6:58
  Dave Hamilton: If the deal goes through, then obviously it doesn't matter because we're going to do this anyway.
• 7:06
  Dave Hamilton: We're just kind of delaying when the papers are signed.
• 7:09
  Dave Hamilton: But if the deal doesn't go through, if it's his fault, if it's the buyer's fault,
• 7:16
  Dave Hamilton: all of that growth is free for you.
• 7:20
  Dave Hamilton: You don't ever pay on that. And it's like, OK, well, that's huge,
• 7:24
  Dave Hamilton: right? Because we do a lot of user acquisition that we're paying for.
• 7:27
  Dave Hamilton: And it was like, this is amazing. Now we don't, like our return on ad spend
• 7:31
  Dave Hamilton: is, it doesn't matter. The ad spend was zero.
• 7:34
  Dave Hamilton: It effectively became organic growth. But it was not.
• 7:40
  Dave Hamilton: And he was nice about it. He was like, but if you decide to kill the deal,
• 7:46
  Dave Hamilton: if we decided to kill the deal, then we wouldn't have to pay for 100% of it.
• 7:51
  Dave Hamilton: In fact, he said, look at what the value of it was to you and you tell us what you want to pay for that.
• 7:59
  Dave Hamilton: And there was, I mean, we put an agreement together that made it so that everyone
• 8:04
  Dave Hamilton: was incentivized to be reasonable with one another in a scenario like that. Sure.
• 8:08
  Dave Hamilton: But this concept of a cancellation clause and that where, where there's,
• 8:15
  Dave Hamilton: you know, cause you're going to head down a path when you start selling a business,
• 8:19
  Dave Hamilton: you're going to be in a scenario where your job is to sell the business.
• 8:24
  Dave Hamilton: Like, and it's not, it's not a, I mean, it is all a sales process,
• 8:27
  Dave Hamilton: but a lot of it's just pulling together paperwork and like all of this stuff
• 8:31
  Dave Hamilton: that's going to distract you from your day to day.
• 8:34
  Dave Hamilton: Even if you know that even if the sale doesn't go through, We're going to keep
• 8:38
  Dave Hamilton: running the business and all those things like this is going to be a job for
• 8:42
  Dave Hamilton: you now. And if and you've got to get paid for that job.
• 8:45
  Dave Hamilton: And so putting something in there that says, hey, we're committed to this.
• 8:51
  Dave Hamilton: We're at this point. We've already gone through enough of this to know that
• 8:55
  Dave Hamilton: we're going to do this deal.
• 8:56
  Dave Hamilton: Now that we're going to do that. OK, now we're moving down a path where like
• 9:01
  Dave Hamilton: reversing course out of this is going to cost us something.
• 9:05
  Dave Hamilton: So now everybody needs to be on the hook for that and you see this on big corporate
• 9:10
  Dave Hamilton: deals they say well yeah you know it's a billion dollars billion dollars yeah
• 9:13
  Dave Hamilton: yeah yeah right yep don't think that that's limited to just those corporate
• 9:18
  Dave Hamilton: deals folks uh you know it can you can do it on much smaller deals too yeah it.
• 9:24
  Shannon Jean: Totally makes sense and it also i think uh
• 9:28
  Shannon Jean: goes to incentivize to like keep the deal moving forward, right?
• 9:32
  Shannon Jean: To where, and in the beginning, I think it also can give you a indicator whether
• 9:38
  Shannon Jean: the company that wants to acquire you is really serious or not.
• 9:40
  Dave Hamilton: Yes.
• 9:41
  Shannon Jean: Right. It's like, Hey guys, there's a, there's a $50,000 cancellation clause here.
• 9:45
  Shannon Jean: If you cancel the deal or back out, because we're going to have to allocate
• 9:49
  Shannon Jean: all these resources to provide whatever you want.
• 9:53
  Shannon Jean: It's different if you're going to them pitching to sell your company.
• 9:57
  Dave Hamilton: That's very different very different if they're.
• 9:59
  Shannon Jean: Coming to you if you're the hottest girl at the dance and they want to dance
• 10:04
  Shannon Jean: with you well yeah you need you know there's
• 10:07
  Dave Hamilton: Why should i not why should i go why are we going to go steady right away put
• 10:11
  Dave Hamilton: a ring on it buddy yeah let's.
• 10:13
  Shannon Jean: Go we're going out to dinner you know
• 10:15
  Dave Hamilton: Whatever so there's some there's.
• 10:16
  Shannon Jean: Costs in there and i think that uh yeah i like i think the concept is great
• 10:21
  Dave Hamilton: I i it is i was just thinking about
• 10:23
  Dave Hamilton: it recently it was like gosh without that would
• 10:27
  Dave Hamilton: we have doubled back down on this
• 10:30
  Dave Hamilton: company or would we have let it like just sort of
• 10:33
  Dave Hamilton: languish and and ride itself into the sunset and
• 10:36
  Dave Hamilton: i don't know the answer to that question but i
• 10:39
  Dave Hamilton: do know that that we did not decide to let
• 10:42
  Dave Hamilton: it languish and run into the sunset and i think a huge part of that is that
• 10:47
  Dave Hamilton: we had some runway i like that like yeah like it was it was a thriving thing
• 10:51
  Dave Hamilton: that was that was being fueled up and it was like wait we don't have to pay
• 10:55
  Dave Hamilton: that bill that's exciting whoa yeah that is our books look so much better it
• 11:00
  Dave Hamilton: was motivated yeah it got us excited.
• 11:01
  Shannon Jean: Yeah yeah especially like if you're in a service business service industry of
• 11:05
  Shannon Jean: one type or another and some private equity companies coming wants to acquire
• 11:10
  Shannon Jean: you i mean that's just a great thing to negotiate into that contract you know yes those you know
• 11:16
  Shannon Jean: They're looking at the hard numbers. It's going to take your eye off the ball.
• 11:19
  Shannon Jean: There's no doubt about it.
• 11:20
  Shannon Jean: You may need those funds to help pay somebody else to get things going or all
• 11:26
  Shannon Jean: the administrative work you're going to have to do, whatever it is. Yeah. It's smart.
• 11:29
  Dave Hamilton: It's crazy. But it was really, like I said, it wasn't my idea,
• 11:36
  Dave Hamilton: but it's going in the toolbox for the next time. And I highly recommend you put it in your toolbox.
• 11:41
  Dave Hamilton: The other things that I highly recommend are our sponsors. The first one I want
• 11:46
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• 11:49
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• 11:52
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• 11:57
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• 12:04
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• 12:08
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• 12:12
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• 12:18
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• 12:23
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• 12:26
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• 12:30
  Dave Hamilton: You work with, you consult for some people that are WhatNot sellers, right, Shannon?
• 12:35
  Shannon Jean: I do. It's incredible, man. It's like you're in the ground floor of something
• 12:38
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• 12:43
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• 12:45
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• 12:49
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• 12:53
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• 12:58
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• 13:01
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• 13:06
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• 13:14
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• 13:19
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• 13:24
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• 14:36
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• 14:39
  Dave Hamilton: And our thanks to Fundera from NerdWallet for sponsoring this episode.
• 14:43
  Dave Hamilton: What's next here, Shannon? What do we got?
• 14:45
  Shannon Jean: Yeah, those are two awesome sponsors, by the way. I have this on my list for a while as well.
• 14:51
  Shannon Jean: And it's a question that we've talked about a little bit.
• 14:54
  Shannon Jean: It's what is your entrepreneurial age?
• 14:57
  Dave Hamilton: Oh, I don't like talking about that. This might not be my favorite topic, Shannon.
• 15:04
  Shannon Jean: No, but actually I think it could. It could be because I, well,
• 15:08
  Shannon Jean: that's what I want to discuss is I want to build a quiz.
• 15:11
  Shannon Jean: I want to ask questions to get people or to let people take our listeners to
• 15:19
  Shannon Jean: take this quiz that we can put up on the website where you can go through and
• 15:22
  Shannon Jean: answer some questions and it will give you some feedback on questions.
• 15:27
  Shannon Jean: Maybe if you're, are you ready to be an entrepreneur? Okay. It doesn't matter
• 15:31
  Shannon Jean: what your real age is, right?
• 15:33
  Dave Hamilton: Oh, I see.
• 15:34
  Shannon Jean: Right? So if it could ask questions like, do you need guaranteed income?
• 15:40
  Shannon Jean: Do you, we talked about the lot, right? Employer versus employee.
• 15:45
  Shannon Jean: Do you mind working on a Sunday night? You know, those kind of,
• 15:49
  Shannon Jean: and just kind of questions. but I don't know yet like how to phrase it in.
• 15:56
  Shannon Jean: It hasn't flushed itself out fully in my brain of what the value of finding that out is.
• 16:02
  Shannon Jean: Is it a test for people that are not in the business yet or do not entrepreneurs
• 16:06
  Shannon Jean: that think they might want to be, or is it a test?
• 16:10
  Shannon Jean: That's kind of where I lead. I'm leaning towards people to ask.
• 16:14
  Shannon Jean: And so I'm not even sure that's the right thing. What's your entrepreneurial age?
• 16:18
  Dave Hamilton: Age to me is for someone who is an entrepreneur, has been doing it for at least some amount of time.
• 16:24
  Dave Hamilton: Right. Otherwise, your entrepreneurial age is zero. Right.
• 16:27
  Shannon Jean: Which is what is your what is your entrepreneurial appetite?
• 16:31
  Shannon Jean: Maybe it's something along, maybe appetite isn't the right word, but it's.
• 16:35
  Dave Hamilton: Aptitude? I mean, what you want to create, what you're creating is an entrepreneurial aptitude test.
• 16:41
  Dave Hamilton: Now, if you, a sexy name might be appetite.
• 16:44
  Dave Hamilton: Yeah. I kind of like that. I like it too.
• 16:47
  Dave Hamilton: It's, you know, finding out your entrepreneur, I'm typing this in here too. Yeah.
• 16:53
  Dave Hamilton: Neural aptitude and preparedness.
• 16:58
  Shannon Jean: Yeah. How prepared are you? How do you handle things?
• 17:02
  Shannon Jean: What's your risk profile? So another thing I started talking about is there'd
• 17:06
  Shannon Jean: be great to have a scale that each of us could rate ourselves.
• 17:11
  Shannon Jean: Like what risk profile are you comfortable with? Are you comfortable burning
• 17:16
  Shannon Jean: the boats and rolling the dice for everything?
• 17:19
  Shannon Jean: Or do you're like, well, I need to keep my day job, but I want to build something
• 17:22
  Shannon Jean: on the weekend, everything.
• 17:24
  Shannon Jean: Because then you could give some guidance to them. Like, okay,
• 17:26
  Shannon Jean: go in this direction or go in that direction.
• 17:30
  Shannon Jean: So I think I could, let's see, I'm going to put that in there with your risk
• 17:33
  Shannon Jean: profile. That needs to be a part of it.
• 17:36
  Shannon Jean: And with some examples of, do you think this is very risky?
• 17:41
  Shannon Jean: Yeah. Or is this not risky? Like, I don't like roller coasters.
• 17:44
  Shannon Jean: I think they're incredibly foolish and risky and I can't go on them.
• 17:48
  Shannon Jean: Got it. But I don't mind risking a few million dollars if I can make another million dollars.
• 17:53
  Dave Hamilton: Yeah. But, like, I think the roller coasters versus a million dollars.
• 18:01
  Dave Hamilton: I'm just writing it down here because, like, that is a good thing.
• 18:09
  Dave Hamilton: So there's a question in there to ask people, but also that's kind of something
• 18:13
  Dave Hamilton: just to say to people and show them, hey, look, what kind of person are you?
• 18:19
  Dave Hamilton: You need to know the answer to this for yourself, for ourselves.
• 18:23
  Shannon Jean: It's for them. Yeah. Yes.
• 18:24
  Dave Hamilton: Right. Like, you know, because if you're not willing to risk,
• 18:28
  Dave Hamilton: I mean, maybe a million dollars is too much to risk. Yeah. Whatever.
• 18:31
  Dave Hamilton: Are you willing to risk? A thousand bucks to make a thousand.
• 18:33
  Dave Hamilton: You know, 10,000 would probably be the kind of minimum number that I would think
• 18:38
  Dave Hamilton: if you're going to get started with a business, but it might be 150,000 too, or it might be a million.
• 18:42
  Dave Hamilton: But if it's like, if you're not willing to risk whatever that number is, let's say 10,000,
• 18:51
  Dave Hamilton: if you're not willing to risk at least $10,000, if you are more comfortable
• 18:54
  Dave Hamilton: going on a roller coaster than risking $10,000,
• 18:59
  Dave Hamilton: being an entrepreneur ain't for you.
• 19:00
  Shannon Jean: Like, yeah, yeah, yeah. Right. Do you need a paycheck?
• 19:05
  Dave Hamilton: Do you need a paycheck? Yes.
• 19:07
  Shannon Jean: That's exactly right. Yeah. So I'm going to, I'm going to build this quiz because
• 19:12
  Shannon Jean: I, I talk to people a lot and I don't know, I think it would be a useful tool, um,
• 19:19
  Shannon Jean: to try to boil down their person's thought process. Cause one of the things that I
• 19:26
  Shannon Jean: Like I talk a lot about, you know, reselling, liquidate, all this,
• 19:30
  Shannon Jean: you know, that kind of stuff. We know.
• 19:32
  Shannon Jean: And I make it and I, and I, I love talking about, I never stop because I love
• 19:35
  Shannon Jean: talking about it, but you can, you can, you gotta be careful because I don't
• 19:40
  Shannon Jean: want to lure people in, uh,
• 19:44
  Shannon Jean: thinking that it's all, you know, gravy or everything's easy.
• 19:48
  Dave Hamilton: Yes. Your, your infectious optimism. Correct.
• 19:53
  Shannon Jean: I don't want that to skew. Yeah. I don't want it to be dangerous.
• 19:56
  Shannon Jean: I want to be able to give them a test like, okay, that's great.
• 19:59
  Shannon Jean: You think it's all good. I love it too.
• 20:01
  Shannon Jean: It's worked wonderful for me, but I don't mind, you know, answering or solving
• 20:07
  Shannon Jean: problems Sunday at 10 PM.
• 20:09
  Shannon Jean: That's just different, right? I've just, I've just built that way.
• 20:11
  Shannon Jean: So I want to build this test and I, and I, it's perfect.
• 20:14
  Shannon Jean: You helped me boil it down. What is your entrepreneurial appetite?
• 20:18
  Shannon Jean: So I'm going to build this test and we will share it here on the show.
• 20:22
  Shannon Jean: I have get some feedback.
• 20:24
  Dave Hamilton: Yeah. Well, yes, for sure. Make sure you listen to Friday's episode because
• 20:29
  Dave Hamilton: what you just heard here is something that I think is really important that
• 20:36
  Dave Hamilton: we need to talk about on Friday.
• 20:39
  Dave Hamilton: That's good. I love it. That absolutely feeds right into it.
• 20:46
  Shannon Jean: Yeah, if you have questions about or things you should think I should ask on
• 20:50
  Shannon Jean: this quiz, this entrepreneurial appetite quiz, send them to feedback at businessbrain.show.
• 20:57
  Shannon Jean: I'd love to hear it because I'm going to build this thing out and I'm going
• 20:59
  Shannon Jean: to use Claude to help me build it out. We're going to figure it out.
• 21:02
  Dave Hamilton: It's going to be great. It's going to be great. Love it. Keep a love of that
• 21:06
  Dave Hamilton: charmed life, folks. And we'll see you on Friday.