FridAI - Priorities and Calendars
30 May 2025 · 25 min
Dave Hamilton and Shannon Jean discuss how a failed acquisition deal affected their business, then explore using ChatGPT to manage priorities and calendars. They share what went wrong and how AI tools helped them get organized again.
Business Brain, episode 653 for Casual Friday, May 30, International Hug Your Cat Day 2025. Greetings, folks, and welcome to Business Brain, the show where we take some ideas and we use them to tune our business brains so that we can each keep on living those charmed lives that we value so greatly. Our sponsors, which we also value very greatly, are shopify.com businessbrain, where you can sign up for a $1 per month trial period, and nordlayer.com brain, where you get 22% off a Nord layer and then when you use codebrain, another 10% off. So we'll talk more about all that in a little bit. For now, here in Durham, New Hampshire, I'm Dave Hamilton.
And in Lafayette, California, I'm Shannon Jean. Happy Friday, man.
Happy Friday, Shannon. You've known. I, I. There is a business that I have that I allude to on this show that I've, I've never really shared the name of and I'm not going to, but it, it, and, and there's no, the, the reasons are sort of a thing with my partners and that sort of. But it's fine.
No problem.
Yep. And we've had this business since 2018. It had spectacular growth sort of out of the gate. We put it up on the block. We've talked about all of that stuff. We had some deals that looked like they were going to come together and then when the economy kind of, you know, went into Covid. Post Covid. Yeah, the post Covid economy kind of went, went uncertain. Let's call it that. Yes, we, those deals sort of fizzled out, which was fine. We had one of our partners that expressed interest in acquiring a majority stake in the company. And that negotiation took a really long time, like 18 months or, or perhaps longer. And it was, yeah, there was no good reason for any of that, but it is what that took. And we were getting, I say we were getting very close to the, to the end of that. We expected that it would close by the end of this month and, and instead the deal died. It did not. Like I, we, we. I often say time kills all deals.
Yeah. Yeah.
And a lot of, a lot of.
Truth to that point.
I thought that this one would be the one that that was the exception that proved the rule. We all kind of did, but it was. The buyers backed out. I'm sure there was something about our business that wasn't perfect for them, although I can't imagine what that would be given how much they got to learn about it at this point, they did not say that that was their reason, but it's always smart to just say it's, it's, it's not you, it's me. Right. But the, the, the, the, the, the letter essentially that we got was like, yeah, look, we've had some major changes to our, to our specific business and there's some, you know, larger changes to the macro economy that we just can't do it. And so we're sorry, you know, we can still partner together, like everybody's still friends, all that stuff.
Great. Yeah.
The interesting part though was my noticing, my reaction to this because the moment I got that email, I was relieved and in theory I shouldn't have been. I mean it, like it wasn't. The whole idea was going to be that they acquired a majority stake in this and then we would become part of, they wanted their, their initial plan, which may have changed, was to acquire a bunch of different related companies, roll it all up, and instead of selling it for, you know, 2, 3, 4, 5X, once you get a company of a bigger size, you can now sell it for 15x. Right. And so that was the idea is roll it up and sell the whole thing. And we would get a second bite of the apple, as they like to say in the, in the business. But, but it was really interesting noticing how relieved and happy I felt when the deal died because in theory, I had worked really hard to put this together and we were going to get some, we were going to take some risk off the table. There was a not insignificant amount of cash that was going to be passed around and that's always good. But it also meant we wouldn't control our business anymore.
So maybe that was the relief that you felt or just, I, I don't know. Every, the dynamic would definitely have changed.
Right.
You, it's not like you would have had, you would have been working for.
Someone, but in a sense I've got somebody to report to. Yes.
Yeah, they had majority ownership. So maybe deep down that was a relief.
I mean, it was certainly there was relief that the process was ending because it's a huge distraction to go through this traction. And you and I learned a lesson a long time ago.
We have been through this. Yes. Ye.
About how not to get emotionally committed to the other side of it until the, the check clears, essentially.
Yeah. Until money's in your bank. Yeah.
And, and yeah, that's true. And so my partners and I learned from that lesson. Like I was able to share that with them in a, in a way that, that they, Even though they didn't really go through it like you and I did, but like, they. They understood it. And part of the frustration was we had several things major, pretty much ready to roll out with this business that we had held onto because some of it was like a major change to the way the website for this business works. And, you know, because we were getting so close to where this deal was going to close, we knew that Murphy's Law was, well, look, if we roll this out and then we find out we're closing in 48 hours, that's the moment that the web, the new website, even though we've tested it and everything's fine, it's going to go belly up for, you know, a day or two while we're trying to fix it. And is that going to scare them off of the deal and all this stuff? So we've been holding this stuff now for a long time, probably, you know, three, four, five, six months. So I'm excited to finally be able to, like, actually get back to work in this business as opposed to, you know.
Yes.
The process of hold. Yeah. Holding and trying to negotiate this deal, which there was not really anything left to negotiate. And so. But I think there was more to it than. I think part of it, and I didn't really think about this until a couple days later was, you know, if it took them 18 months to put a relatively small deal together.
Yes. Yes.
How long is it going to take them to put the roll up together.
Or just to make any decision?
Yeah. Yes.
Right.
Yeah.
I mean, we always. A part of our superpower, and I have. And I know you have this, too, is making fast decisions.
Yes. And I. And these people also can make fast decisions. Like, there were some things that were inexplicable in certainly in retrospect, because I know these people, we've worked with them for almost the entirety of our, you know, the longevity of the business, which is, you know, seven years. But there were just some. Some things where it was like, yeah, I don't. Like, I don't. I don't know. I. There certainly were moments where I was. The. The unknown of what it was going to be like once this happened, once this deal closed. I had to put out of my mind, like, you know, over the last month and a half, like, I would. I would get into my head about something and be like, well, once we're. What is that? And are we going to be out in a year? Because they only wanted to do one year's worth of employment contracts, why didn't they want to do two? Wouldn't they want us around? Are we going to be out? Like, is. Do we really not get to control. We still maintain the. The minority stake, of course, but sure, you know, do we not get to control our destiny at all? Like, oh, that. But as soon as I had that thought, it was like, nope, we'll figure it out when we get there. We're too close. Don't. Don't start. You know, don't, like, don't sour this thing now. So. But it was really interesting. Like, I was.
It is. I think it's stressful, too. I think it's just.
It is.
All those unknowns are introduced. Another layer of, oh, wow, I don't know what's going to happen. And I've got, you know, all that stuff. It's. It doesn't come without a cost. Right. There is a cost associated with selling all or part of your business.
A majority part. And there was a moment, and our. Our attorneys don't know the other party like we do, which. That makes perfect sense.
Yeah.
However, there was a moment, and this was like, 10 months ago. It was a while ago. The other people had the wrong attorneys that made this thing drag out for sure for a while. Then they got a great attorney and everything worked out great. Except it didn't. But we liked the attorney. And our attorney said to us, they're like, you know, you might just be selling your business for 60% of what it's worth, though, because we were going to sell 60% and keep 40.
Yeah, yeah, yeah.
And they're like, we've seen this before. And maybe that stuck in my head, you know, attorneys are. Attorneys are built to kill deals. Like. Like that. That is the profession.
Yep.
But it was. Yeah, it was interesting. It was an interesting. And it's. This only happened, I think it was a week ago today that, you know, we found out that this deal was dead. And, yeah, you know, we all. We all kind of went through our process, but then we met two days later, the three of us partners, and there was no negativity. It was like, all right, this is great. Let's go.
Yeah. One door closes, man.
Yeah, that was.
Another one opens up. So.
And. And no small part of it was the employment contracts. You know, we. We were. There was a fixed salary, if you will, you know, that we would get paid. And it was like, well, this is kind of weird. Like, what do we do? We don't get to control what happens with the profits anymore. Like, this is a decision we make with somebody else, huh? Yeah, I don't know. Anyway, it was an interesting, it was an interesting thing to go through, but, and you know, like you said, opportunity knocks and we're, yeah, it's, yeah, it's, I don't see it as a negative, other than the obvious thing of taking risk off the table. Means that the, there are, there are also unknowns in keeping it right. Like, you know, of course, obviously.
Yeah, there's, there's, you know, yes or no. There's repercussions.
Correct and correct. And you're, you don't get to know.
It's going to go. No, you don't get to know.
You don't get to know.
Don't. Yeah, no, no. It's amazing. Well, I think I, I, I bet you it'll work out well for you guys.
I think it will. I, I think it, yeah, I, I feel really good about it, as do my partners, which was I, you know, when I went into that kind of team meeting that we had on, on Thursday of last week, you know, two days after this thing, I was like, all right, well, do I need to be like the cheerleader here and like make sure everybody focused and everybody's situation is different? Right. Correct.
Yeah, that's good.
Correct. That's really great. Yeah, yeah. So, yeah, it's good. We have Friday AI to do. And the next thing I want to do is tell you about our two sponsors because look, if your business is growing fast and your tech stack looks like it was built during a caffeine fueled weekend hackathon, congrats, you're doing it right. But now you need NORD Layer, our sponsor, to keep it all secure without pulling you into it. Purgatory. NORD Layer is, is the network security platform built for modern businesses. It's your vpn, your access control, your compliance assistant, your threat shield, all wrapped into one neat toggle ready package. You can deploy it in minutes, scale it with your team and monitor who's doing what and from where. And it's based on zero trust, meaning you're not handing out skeleton keys to your entire castle. It's just enough access for the right people at the right time. Oh, and if you ever wanted to feel like you have a security operations center hidden inside your laptop bag, NORD Layer's built in threat detection and dark web monitoring. Kind of makes that happen. No cape required. Protect your business the smart way. You get up to 22% off Nord Layer's annual plans at nordlayer.com brain/10% more with Code Brain. So that's nordlayer.com brain Code Brain. Stay fast, stay safe, stay charmed. And our thanks to Nord Layer for sponsoring this episode. And you know that question that lives rent free in every entrepreneur's brain. What if it actually works? Right? That's the wild part. Because it can. But you need the right foundation. You need our sponsor, Shopify. Maybe you're thinking what if I don't know how to build a website? Well, Shopify gives you gorgeous templates, no coding required. What if I need to help writing product descriptions? Well, Shopify has got AI tools that'll do that with you. What if I launch and no one buys? Well, Shopify's built in email and social marketing tools help you find customers wherever they are scrolling. Shopify powers 10% of all E commerce in the US that's amazing. Not just side hustles and startups, right? But brands that you know and trust. And if Shopify can help a team launch a burrito themed sneaker line, yes, that happened. Then it can definitely help you. So stop with the what ifs and start building your charmed life. Turn your big business idea into Ka Ching. With Shopify on your side, sign up for your $1 per month trial and start selling today at shopify.com businessbrain go to shopify.com businessbrain again shopify.com businessbrain right. And our thanks to Shopify for sponsoring this episode. It's time for Friday. I Shannon, I have a. I love Friday. I. I have a quick one to start with.
Great.
I mean, I say it's going to be a quick one. Who knows? Lydia Davey, the co founder at Attentio PR said she posted on LinkedIn. She said work's been intense lately in the best way possible. And here's how. I'm using ChatGPT to stay ahead of the curve. I grab a pen and scratch every last task into my planner. Okay, fine. Then I snap a pic and upload it to ChatGPT with the prompt. I don't think there are enough hours in the day for me to do this work. How might I prioritize this client work that needs to get done today? And what might I be able to reasonably outsource? Block my time for me.
Can you give it access to your calendar?
I don't think so. That's interesting. But I mean it could certainly build a calendar for you. But yeah, you know, I mean. Well, at the very least you could take a screenshot of your calendar for the week showing your time that's blocked and unblocked and give it that and say, create my calendar with, you know, fill in the rest of my calendar. Right. You know, I like that. Knows you got business brain to record here and band practice there, whatever. Like, okay, great. Like, I put screenshots into chat GPT more often than not. When starting a prompt now. Or pictures. Pictures of some sort. But, yeah, screenshots, specifically. Yeah, yeah, It's.
I love it.
It's.
I'm asking it right now. I just took a screenshot of my next two weeks because it's. It's a hell mayhem of mayhem because I was gone on vacation. I'm gonna see what it has to say. Okay. So she writes everything down, just, like, takes her notes, what I got to get done, what I get done. Then she uploads it and asks it.
To block my time and prioritize the work. Right. Like the prompt. I'll say it again because it's. It's great. She starts by saying, I don't think there are enough hours in the day for me to do this work. How might I prioritize this client work that needs to get done? And what might I be able to reasonably outsource? Block my time.
I like it.
Right.
I just upload. I uploaded my two weeks, and it says, whoa, your calendar looks like it's nearing critical overload.
That's never a good thing when the robot can't handle what you've done to your life.
Yeah. And then it says, here are seven proven strategies to bring sanity back to your schedule.
Huh.
That's kind of cool.
I bet. I bet you could upload if you exported your calendar as an ICS file. You could upload the ICS file to Chat GPT and have it parse that. I don't see any reason why not.
It's not a bad idea.
Yeah, yeah.
It's pretty savvy. I mean, it's looking at, you know, what do you want to do? More deep work, more whatever. You know, that kind of stuff. Yeah.
I had an interesting. I was standing at south by Southwest waiting for a band to start playing, and I ran it. Tell me if this sounds familiar, because I've certainly told this story, but I don't think I've told you. And I was standing up near the front of this venue. It was a relatively small venue, and a photographer showed up, and they always make their way to the front, and they're very good at creating space where none exists. And. As was this guy, right? And he had a unique look to him. This, like, yellowish hair and Big and like, he had a, he had a look. I was like, man, we were chit chatting for a little bit. I'm like, I feel like we've met before. I'm like, maybe last year here or something like that. And he's like, maybe you live here in Austin. He's like, no, I live in Boston. I take pictures of bands all over the place. I'm like, ah, okay. I also live near. Right. You know, we. And it's like, okay, well, he's like, maybe I took pictures of your band. I'm like, that's possible. And so he's like, let me look. And he keeps on his phone, he has access to a Google Sheet where 1, 1 per year. He lists all of the events that he attended and shot and all, and the dates of it and all and the bands that were there. And he's like, what's the name of your band? I told him Bitter Pill. And yeah, I don't have it. And he looked at the years that he thought it would be and he's like, yeah, no, that wouldn't be it. Like, okay. And he was like, yeah, but you look familiar too. He's like, I don't know why? And I said, well, if only. I said we could use Chat GPT to solve this. Now we didn't, because in the moment, I'll explain to you what I was going to do, but like, we did not have devices that would let this happen.
Ah, okay.
But I like, if I had access to my computer, I would have. I thought, okay, well this is a perfect use case for Chat GPT. And a friend of mine was there. He's like, I got to learn about ChatGPT. I'm like, great, here's an idea. He has all of these dates in a Google sheet. I have all of the shows I've played and attended in my calendar. So if I export my entire Calendar as an ICS file and upload that to ChatGPT, and he takes his spreadsheets and saves those as spreadsheets and we upload that to ChatGPT, it can very quickly go through and find the dates where we were in two different places even though. Or to the same place, even though it's two different modalities of that data, right? Like, I don't have to take my calendar and turn it into a spreadsheet to match his. He doesn't have to, like, it will do all of that and, and just come back and say, yeah, here's the dates where you guys were in the same place at the same time. And we haven't done that yet. But. But like, but those are the kinds of things that are good to think about with chat GPT. Those, like the. The multimodal stuff, especially where it's like, all right, look, here's a screenshot of this one thing and here's what I getting from this other thing. I use it for tech support all the time and it synthesizes all that data into one blob for itself to then analyze or for you to analyze. It'll. It'll, you know, regurgitate it back to you.
But yeah.
Anyway, those are my. My two. My two additions for. I love.
Yeah, it's great. I. I'm going to follow some of these tips that after just uploading the snapshot on my calendar, I can already see you're.
You're like, you're finished with the episode and moving on because you've got.
Wait a minute. I gotta go get this done. Yeah. Oh, my gosh. Ridiculous. Yeah. Well, there's always a price for being on vacation. You just have to, you know, the first week back is always a challenge. But I have this. A Mastermind. This is $5 mastermind. It's all about reselling and everything. And one of the things I implemented on advice of my coach who helps me out was, hey, you should book a call with every one of those people that signs up because they will be leads and they will help you and you can learn. And I'm like, that's a great idea. Because when you're a coach, you always want new clients, right?
That's the whole gig, man.
Yep, that's the whole gig. So I'm like, great. And I love talking to people and everything else, but I had an explosion of new signups and we're almost at 500 members.
500 half hour calls is a lot. Or even 15 minute calls.
I only do 15 minutes and doesn't matter. Even though it doesn't matter. And yes, it does work. I have recruited clients from there. It's wonderful. I love talking with people. And there are folks.
That's 125 hours, right? 500 times 15 minutes. No, that's 500. 125. Yeah, yeah, right. Isn't that. So 500 people times quarter of an hour is 125. Yeah, yeah, yeah, yeah, yeah.
So I'm. I'm coming off of. Yeah, so I'm changed this morning. I changed what I did. One of the things that the AI suggested I do is block out the time and don't Let it. Yeah. Let people schedule. So I blocked out 90 minutes in the morning each day to take those kinds of calls, and that's it.
Yeah.
And that way. But. But inevitably, what I get is I went to your calendar and the first availability was a month out. Like, man. Yep. That's just the way it is. I don't know. So it's kind of. It's. It's.
It's.
It's a pro benefit, and, you know, it's like, oh, my gosh, when I only had 50 people in there, it was, okay, great, I'll do it. But, yeah, when we've scaled and doubled our. Tripled our members in the last month, it's. It's a challenge. Good problem to have. I love talking with people and. Yeah, it's great.
The consultant trap.
I'm working through it.
I know.
Working through.
No, I. Yeah, I know.
Yeah. System, you know, having never done it before, really developing the systems and the. I'm doing it manually at first, just like we talked about in the previous episode, and learning lots of great stuff by doing it manually. And now I'm automating systematizing and bringing better control into it. So it's a better experience for me and.
And for my clients and for your clients. Yeah, absolutely.
Yeah, definitely. Definitely. So it's great. Good stuff. Yes.
Yep.
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