¶ Business Brain – The Entrepreneurs’ Podcast #653 for Casual Friday, May 30th, 2025
Business Brain, episode 653 for Casual Friday, May 30th, 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 slash BusinessBrain, where you can sign up for a $1 per month trial period, and NordLayer.com slash Brain, where you get 22% off at NordLayer, and then when you use code Brain, 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, there is a business that I have that I
¶ A deal died…and I liked it?
allude to on this show that I've never really shared the name of, and I'm not going to. Yeah. But, and there's no, the reasons are sort of a thing with my partners and that sort of thing. 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 went into – Post-COVID. Post-COVID. Yeah, the post-COVID economy kind of went uncertain. Let's call it that. Yes. 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 perhaps longer. And yeah, there was no good reason for any of that. But it is what that took. Yeah.
And we were getting very, I say, we were getting very close to the end of that. We expected that it would close by the end of this month. And instead, the deal died. It did not, like, I often say time kills all deals.
Yeah, yeah.
A lot of truth to that, boy. I thought that this one would be the one 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 not you, it's me, right?
But the letter essentially that we got was like, yeah, look, we've had some major changes to our specific business and there's some larger changes to the macro economy that we just can't do it. And so we're sorry. We can still partner together. 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 uh 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 two three four five x once you get a company of a bigger size, you can now sell it for 15 X.
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, uh, as they like to say in the, in the business. But, um, um, 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 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.
Yeah. So maybe that was the relief that you felt or just – I don't know. So the dynamic would definitely have changed, right? It's not like you would have been working for someone,
But someone else. 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, certainly there was relief that the process was ending because it's a huge distraction to go through this. And you and I learned a lesson a long time ago.
We have been through this, yes.
Yep. About how not to get emotionally committed to the other side of it until the check clears, essentially.
Yeah. Until the money's in your bank.
Yeah. 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 way that they – even though they didn't really go through it like you and I did, but like they understood it. And part of the frustration was we had several things, major things that we have pretty much ready to roll out with this business that we had held on to 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, the process of 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 rolling things out. You also can make fast decisions. Like, there were some things that were inexplicable, certainly in retrospect, because I know these people, we've worked with them for almost the entirety of our, you know, longevity of the business, which is, you know, seven years.
But there were just some like some things where it was like oh yeah i don't like i don't i don't know i 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's really interesting like i was it
is i I think it's stressful.
Too. I think it's just all those unknowns introduce another layer of, oh, wow, I don't know what's going to happen. I've got all that stuff. It doesn't come without a cost. There is a cost associated with selling all or part of your business.
A majority part. And there was a moment. And 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. 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 uh but it was yeah it was interesting it was an interesting and and it's this only happened uh we it was i think it was a week ago today that 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 it well 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 um 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, the, there are, there are also unknowns in keeping it right. Like, you know, keeping, of course, obviously. Yeah.
There's, there's, you know, yes or no, there's repercussions.
Correct. Correct.
And you're, you don't know which way it's going to go. Nope. You don't get to know.
You don't get to know.
Yeah. No, that's amazing. Well, I think, I bet you it'll work out well for you guys.
I think it will. I think it, yeah, 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 uh 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's focused and.
Everybody's situation's different right yeah that's
Good correct that's really great yeah yeah so yeah yeah it's good uh we have a friday ai to do and uh 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
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¶ Lydia Davey-FridAI idea for capturing and prioritizing client work
It's time for Friday. I Shannon, I have a.
I love Friday.
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 attention 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. Hmm Ah Can.
You give it access to your calendar? Yeah
I don't think so. That's interesting. But, I mean, it could certainly build a calendar for you. But, yeah, you know. Yeah, okay. 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? I like that. If it knows you've got business brain to record here and band practice there, whatever. Okay, great.
I put screenshots into chat GPT more often than not when starting a prompt now. Or pictures. I've been doing that. Pictures of some sort. But yeah. Screenshots specifically. I like that. Yeah. Yeah. I love it.
I'm asking it right now. I just took a screenshot in my next two weeks because it's a hellscape of mayhem because I was gone on vacation. I'm going to see what it has to say. Okay, so she writes everything down, just like takes her notes of what I got to get done, what I got 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 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 today and what might i be able to reasonably outsource block my time i like it right it's i just 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 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. Oh, that's kind of cool.
I bet, though, I bet you could upload, if you exported your calendar as an ICS file, you could upload the ICS file to ChatGPT 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,
¶ Multi-modal uses of AI
waiting for a band to start playing and i i ran it if tell me if this sounds familiar because i've certainly told this story but i don't think i've told you and uh i i was standing up near the front of this venue it's 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 and as was this guy right and uh he had a unique look to him this like yellowish hair and big and like he had a he had a look and 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 i'm like 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 like 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 one one 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 uh he was like yeah but you look familiar too he's like i don't know why and i said well if only uh i said we could use chat jbt 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 uh okay but i like i 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 chat GPT. 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 chat GPT, and he takes his spreadsheets and saves those as spreadsheets, and we upload that to chat gpt it can very quickly go through and find the dates where we were in two different places even 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 yes 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 we haven't done that yet but like but those are the 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'm 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 two my two additions for uh i love it yeah it's great.
I i'm I'm going to follow some of these tips after just uploading the snapshot of my calendar.
I can already see. That's awesome. You're like, you're finished with the episode and moving on because you've got these things. Wait a minute.
I got to 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. Yes. But I have this mastermind. This is a $5 mastermind. It's all about reselling and everything.
And one of the things I implemented on the 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,
¶ AI to manage your time
you always want new clients, right?
That's the whole gig, man.
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.
I only do 15 minutes and doesn't matter even though it doesn't matter yeah uh and yes it does work i have recruited clients from there it's wonderful i love talking with people uh and there are folks that's
125 hours right 500 times 15 minutes no that's 500 125 yeah it'd be.
125 hours yeah right isn't
That so 500 people times point a quarter of an hour is 125 yeah.
Yeah yeah yeah so i'm i'm coming off of uh 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, let people schedule it. So I blocked out 90 minutes in the morning each day to take those kinds of calls and that's it. And that way, but inevitably what I get is I went to your calendar and the first availability was a month out. I'm 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, uh, 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 when we've scaled and doubled our, uh, tripled our members in the last month, it's a, it's a challenge. Good problem to have. I love talking with people. Um, and, uh, yeah,
It's great. The consultant trap.
I'm working through it.
I know. I'm working through it. No, I, I, I, yeah, I know.
Yeah. Systemation, you know, having never done it before, really. Yeah. Developing the systems. Yeah. And I'm doing it manually at first, just like we talked about in the previous episode. Yep. 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 for my clients.
And for your clients. Yeah, absolutely.
Yeah, definitely. Definitely. so it's great good
Good stuff yes.
Yes yep all right uh that's good that's all i got all right today i'm happy to yeah it's a good thing but i do want to remind you if you're listening we're giving away a macbook and so far we only have a handful of people that
¶ Business Brain 653 Outtro
have entered to win so your odds are incredibly in your favor way high so go to businessbrain.show slash review and leave us a review. And every time you post a review, you'll be entered to win. And we're going to give it away. And so far, I think maybe we have 10, 12 people.
I think it's probably closer to 30. But, you know, still.
Well, you know, directionally. Yeah. That's good. But so, yeah, go leave us a review. Plus, it helps.
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