Married to the Startup

The Exit Plan Nobody Talks About — Startups, AI, and Staying Married

Alicia McKenzie Episode 44

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In this episode, Alicia and George dive into two conversations that stopped them in their tracks:

  • AI & Privacy: Did you know ChatGPT conversations briefly showed up on Google search results? We unpack what that means for your data, why privacy settings matter, and how people are (mis)using AI as therapists, lawyers, and business consultants.
  • Life After the Exit: Everyone talks about how to position your company for sale—but nobody talks about what happens after. From identity shifts to lifestyle creep, George and Alicia get candid about what founders (and their spouses) should prepare for when the exit day finally comes.
  • The Billion-Dollar Doodle Boom: On a lighter note, meet Fitzgerald Graham, the newest addition to the McKenzie family. His arrival sparks a hilarious detour into the surprising economics of doodles, dog TikToks, and why Alicia is ready to launch her pup’s influencer career.

This episode is equal parts sarcasm, humor, and perspective—from AI glitches to puppy culture to navigating the emotional rollercoaster of selling a business while staying grounded in family.

If you enjoyed today’s conversation, please like, rate, and subscribe. Your support keeps us going!

Resources:

https://medium.com/how-to-profit-ai/your-chatgpt-history-just-went-public-on-google-heres-what-i-did-in-10-mins-to-fix-it-103c6b88c8ba

https://www.bloomberg.com/features/2025-doodle-dogs-billion-dollar-business/?utm_source=substack&utm_medium=email&embedded-checkout=true


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George McKenzie (00:00.298)

all the conversations I've ever had previous to thinking about this, a lot of people, it's all about the exit, how awesome it's going to be and how to make the money and how do you position your company for exit? How do you do all these? Not a lot of conversation of, okay, you as a person and your spouse and your family, how are you going to do this? I it's similar to winners, right? think most lottery winners have terrible lives because they don't have a plan for it, just euphoria of I won and then they go crazy.

 

Welcome to Married to the Startup.

 

I'm Alicia McKenzie, a wellness entrepreneur and digital creator. Alongside me is my amazing husband, George, the CEO who's always ready for a new challenge. We've been navigating marriage and running startups for over a decade, and we're here to share the real, unfiltered journey with you. Join us for insights and candid conversations about integrating love, family, and entrepreneurship. This is Married to the Startup, where every day is a new adventure.

 

And we are back. Welcome to episode 44 of Married to the Startup. I'm here. I know, 44. Who?

 

John Reagan's Former Redskin.

 

Alicia McKenzie (01:14.2)

Farmer Redskin. Yeah. Not a commander. Nope. Redskin. Yeah.

 

He played for them, not for the commanders.

 

He did. All right, we're going to jump right in because this is a topic that literally stopped me in my tracks. Your chat GPT conversations are showing up on Google. Could you imagine? No. Everything that I've talked about with chat GPT? Tea. Actually, personal. Yeah, me neither. Right? I think the only personal shit that I put into chat GPT are my labs.

 

I don't know, what have you talked about with Chat TV?

 

George McKenzie (01:42.934)

Yeah, that might have been controversial. Yeah, I just ask it to do remedial tasks for me. Shit, I don't want to do.

 

Brightly

 

Alicia McKenzie (01:51.118)

But there are some people that go deep with the chat GPT and I feel like that is just a whole different conversation. But the article that I read and I will drop it in the show notes basically said that for 72 hours there was a fault within chat GPT that allowed it to use your conversations with chat GPT and provide those answers as

 

actually provide the conversation as an answer to somebody's Google inquiry.

 

So Google could index it? Yes. Index those conversations and then serve them up as search results.

 

Correct. Way to say that more succinctly than I did.

 

Yeah, I know. Well, that's what I'm here for. Good job. Yeah, I do have a role.

 

Alicia McKenzie (02:38.99)

Yes, but it wasn't supposed to happen that way. Really? It was a huge, huge privacy issue. Huge privacy issue.

 

Yeah, I think it just scratches the surface on the deeper topic of using these LLMs and chatbots, AI interfaces, and that data, once you put it in there, it is not yours. It's run by OpenAI or Google or PickClaude or whoever is running it on the back end of the LLM of choice. And that data is now theirs. And if they make mistakes, they can provide it to other people. Or they can leverage that data.

 

in their own AI answers to other people. So when you ask questions, you provide marketing content or you provide what have you, you can't control where that data goes on the other end. Who gets served up to how it gets used and abused for ripoffs or stuff that looks just like it or sounds just like it. it's quite interesting. And then some of the challenges there, businesses do it and are leveraging these platforms and I know there's business licenses which have more containerized.

 

LLMs where it's just your data. But, you know, think the vast majority of people are paying the $20 a month to open AI and just use it. And there's no, I mean, some data protections, but as you can see in this instance, like you're 100 % outsourcing all that.

 

So raise your hands if you actually read the terms and conditions of any platform that you use.

 

George McKenzie (04:11.47)

I do not, but I have begun recently taking that and giving it to ChatGPT to read. Like anything legal that I get now, I go to ChatGPT and I ask it to summarize the risks. And then I take that same thing and give it to GROC and have it give me the risks. 99.9 % of the time, it's all the same. It'll tell you the same risks, are really stuff you're willing to accept anyway. But it's an interesting way to...

 

turned through all that day.

 

But most normal people are not doing this. So you have no clue what the T's and C's of any platform that you use is telling you. They could say, we're selling your shit to Russia. You would have no fucking idea.

 

Yeah, I think most of them just say we own it and you have no right to it. Yeah. Which means you can do whatever. And I think I read a quote by Sam Altman that was saying that a lot of that personal information on which you type in that you realize that, especially because people use it as a therapist or they use it as a lawyer and we should talk about this more, but none of that stuff is covered under client-patient privilege or legal privilege like

 

Anybody could subpoena your results or your conversations with chat GPT or with Grok or Claude or whomever, and you know, could use that against you.

 

Alicia McKenzie (05:30.222)

Right, that's the common misconception that everything that you're putting in to chat GPT is private. Right. It's not.

 

Yeah, so it's unlike other platforms which encrypt everything and will not give it to law enforcement or what have you. But someone could subpoena your conversation with OpenAI and say, I want to know everything that Alicia said about George in terms of whatever and use that in a lawsuit.

 

The comical part though is that I don't even use chat GBT in that fashion.

 

i don't but i know a lot of people that do

 

There are a lot of people that are acting as a therapist.

 

George McKenzie (06:07.858)

Yeah, and it's an interesting, I don't know. Maybe it provides access to people that maybe not have it or it provides them, know, maybe it meets a need where they are uncomfortable talking to people. So it's much easier to just type or have a conversation with someone you know is not human. So you're able to be more vulnerable and not being feared, you know, no judgment. You don't fear being judged by this cloud-based AI thing that you...

 

you can't see or won't see you walking down the street or you won't bump into it at the grocery store. So they're more willing to be open and honest. Yeah, I don't, I mean, I think there's good to it. I just, you know, we're not, you know, we're so far down the rabbit hole that you can't walk it back. But how do you create guidelines? How do you create those, you know, HIPAA constraints within the data? Like if I have that conversation with an AI pretend therapist, how is that data covered?

 

I don't know how I feel about that.

 

Alicia McKenzie (07:04.386)

Yeah, and I know that access is an issue, but I just, don't know if chat GPT is the answer.

 

Yeah, I don't know. Well, you remember that grog thing, like, you could have your sexy voice therapist talking back to you, saying everything that you want.

 

No, and when this whole thing came out, like the conversation showing up on Google, there was a setting within ChatGPT inside the privacy settings that you had to go in and like look and check and change before ChatGPT was able to fix the problem. do you even like, when's the last time have you ever checked your privacy settings on ChatGPT or Grok or Claude or?

 

No, I can say that I have not. I should probably do that. I might do that right after this pod.

 

considering your background, I feel like that's an easy fix.

 

George McKenzie (07:54.158)

Should be. I'm growing less paranoid. It's probably not a good thing. used to be uber paranoid. Now I'm getting less. I don't know why. Why that is. Maybe I'm just getting older. I just don't care as much.

 

No, it's not.

 

Alicia McKenzie (08:08.524)

What could happen? What's the worst that could happen? Maybe your anxiety is getting better. Maybe that's what it is.

 

Maybe it's puzzle. It is it's one of those 73 pills. I take a day is working All vitamins all that all nothing prescribed

 

Not true. But yeah, that was like a stop you in your tracks type moment, right? And it's not to say that I have anything personal on chat GPT, but I know some people do.

 

And it's the personal, but it's also like the business stuff. I know a lot of people that, I mean, I've used it to, you know, get me started, give me a skeleton sal for this or give me a skeleton, you know, response to a sal based on these three things. And, you know, get you started.

 

Yeah, and I know people who use it for PR. So there's a lot of PR contacts in there. And if all that is being indexed and with the possibility of showing up on Google, is that

 

George McKenzie (09:00.398)

Yeah, especially if you're using it. I mean I could see the value I've done it to do you know things I would do in Excel that take a long time of hey, let's do this, you know give it all to me in one column versus three columns and Cross reference it with you know this other database that I have and give me only the things that are unique and you can spit that out in seconds and can you imagine using that for like mailers like hey, here's this

 

you know, contact list of all my clients out of HubSpot. I want you to take this, massage it, and put it into a format that, you know, some other mailing tool uses for Eventbrite or whatever. And then now all those emails, people's names, all that, you know, stuff that you've spent time curating to get this contact list, if that was available to anybody, could grab it. Now, you know, the value of that list is watered down and maybe it's easier to other people to market to them.

 

They just go, Hey, give me all of, you know, customer context for next chapter. wonder if you could do that. I have to ask.

 

do that. Don't do that.

 

Yeah, well we can do others. Yeah. That'd be interesting.

 

Alicia McKenzie (10:10.062)

other people's company. Maybe we'll do C-Vent.

 

Yeah, C-Vent. C-Vent. Everybody. It would just be a list of the phone book.

 

Yeah. Anyways, back to this.

 

Yeah, no, just think it's, you know, we're just scratching the surface really on utility. And I think that it was interesting, like that study that 95 % of the AI projects being done today are, you know, are providing little to no value or are failing. And, you know, it doesn't, it hasn't slowed the funds going into these AI companies and chips like the billions and hundreds of billions that are going into these companies.

 

to start building their own chips now to be able to be more efficient to run these large Langley's models more efficiently to have more AI agents out there. So we're not slowing the investment in it, but yet we've gotten very little of the ROI in the business world. I'm confident we'll solve that problem, but it's just an interesting dynamic where.

 

George McKenzie (11:15.478)

I guess everyone's betting on it's going to work and then everybody's using it today for a variety of things without understanding really ramifications of where does the data go? Absolutely.

 

think that's the scary part is that this wasn't a user error. Right. This was a system error. This was a backend system error. OpenAI confirmed that there were technical flaws and then they went and fixed it.

 

Can you imagine how crazy it's like it's such a different world that we live in how fast it's changed like the way that Tesla just over the fly over the air will update stuff so and fuck that didn't work okay roll it back hey we're doing it live there's no QA testing QA is dead it's just roll it out let every let the world QA it and then we'll fix it

 

Yeah, I remember back in my CBD, my CBP days, CBD, you used to have to test everything on an environment that wasn't live.

 

Exactly like the production environment and then you would you remember burn in was the thing like they do all these used to do all these QA tests and yeah Now I feel like it's just roll it out live QA tested on the world and when someone complains then Fixed whatever they find because the world will QA it for you The world will find the problems faster than any five guys in a room. That's insane. Yeah But that's it feels like that's the world we're living the CICD pipeline is kind of you know, build it iterate roll it out

 

Alicia McKenzie (12:36.686)

main.

 

George McKenzie (12:44.642)

Build it, iterate, roll it out.

 

So I think bottom line is that you're using these AI tools, right? You're using Grok, you're using Claude, you're open AI. Stop putting your personal shit in there.

 

Right. Yeah. I know several people that use it religiously as like, hey, act as my therapist. And you have that chat window open, it remembers everything about you, and you just, to your point, go deeper. And you're like, getting psychoanalyzed by an AI chatbot. Yeah.

 

I don't need OpenAI to tell me about myself. I already know my flaws.

 

Well, some people don't. Some people are as self-observant as you.

 

Alicia McKenzie (13:25.39)

Oh no, I know exactly. I could name to the T.

 

You're false. None. Is that your answer? that your answer? I have none. Basically. Mine are. Name it. Flaw.

 

Perfectly perfect.

 

Alicia McKenzie (13:38.594)

whatever. Technology is great.

 

It's moving so fast.

 

But it's also like there, I feel like there are no guardrails on AI right now. And we're just kind of like going as fast as we possibly can to win the quote unquote AI race. But to what

 

And I think it's interesting that it used to be like the cycles of marketing and cycles of product development like you'd have the the early adopters and then you have everybody else and then it goes in the cash cow phase and it's just you know Everyone's using it becomes blase and people have moved on to the next thing Yeah, but I feel like we are the early adopters are like everybody It's not this fringe group of people that just want to be on the front forward leaning edge. Like everyone's doing

 

It's wild because like our nine-year-old is talking about chat GPT and using AI.

 

George McKenzie (14:31.672)

mean, they use Alexa all day and that's all they are.

 

Yeah, I guess. guess they've been ordering shit off Alexa since they could tell.

 

Yeah, and it's just that it's interesting the way in which we interface with computers has changed. Like for me, it's all keyboard, mouse. Like that's what I'm most comfortable with. You're probably most comfortable with tactile with your finger. For my phone. You're a touch screen. That's probably your preferred interface. mine is a keyboard and mouse. And think our kids' preferred interface is voice. Like that they would rather talk to it and get answers than touch and type.

 

I can run the world.

 

Alicia McKenzie (15:07.424)

very

 

But it's happened so fast. And I can see that, you know, the next leap will be the AR, right? Where you're interacting with the computer live on your face. I I played pickleball the other day with someone who had the Ray-Ban glasses on.

 

I can't, no way.

 

and he was videoing a serve and stuff and it's like. Who was it? I can't tell you. Not on the pod, but I'll tell you afterwards. I mean, you should be able to guess. So yeah, it's just interesting. everything's moving. Everything's shifting left. Yeah.

 

Quickly. bottom line, please, please. Don't ask OpenAI to analyze you.

 

George McKenzie (15:42.968)

Careful with what you put in there.

 

George McKenzie (15:50.478)

I might do that now, just to see.

 

Why? Because. What could it possibly tell you? could tell you you're a psychopath. Hmm. It could tell you you're a narcissist. Not. That's what I'm saying, but it probably could. It probably thinks everybody's a narcissist. Anyways, all right, moving on.

 

time.

 

George McKenzie (16:08.43)

part of Skynet's plan. It's gonna make us all feel bad. And then get us all to take the same drugs. And then it can control us.

 

Exactly. Rage against the machine. Rage against the machine. All right, moving on. Baby, what are we doing soon? What are we doing? I don't know. We're getting a...

 

Daddy's back.

 

George McKenzie (16:27.372)

having a baby?

 

George McKenzie (16:30.936)

No we're not. keep stirring up this false fake news. Fake news.

 

We're getting a puppy. His name is Fitzgerald Graham.

 

You're just laying groundwork so that when it happens, everyone thinks I agreed.

 

Exactly. So his name is Fitzgerald. And he is going to match our other puppy, who's Huck, and Olivia. We call her Olive, but in my mind, her name is Olivia. And he's rounding out the Scandal Trio. And he's so little and he's so cute. But that brought on me finding this article about the doodle boom. So we currently have two doodles. Our first doodle, her name was...

 

Grace and we got her. She was such a good dog. passed away the year Maya was born. But we found her randomly at a U-Haul slash.

 

George McKenzie (17:14.901)

dog.

 

George McKenzie (17:25.79)

bait and tackle slash puppy mill. was quite a unique smattering of items the mercantiles sold.

 

of illegal.

 

Alicia McKenzie (17:40.994)

Yeah. I'm pretty sure they were just laundering money.

 

Yeah, probably. Yeah, we were moving my parents into their first house. Yeah. And then fixing it so we went to go get a U-Haul.

 

Yeah.

 

Alicia McKenzie (17:51.276)

went to go get a U-Haul and we saw two puppies and a friend of ours was going through like some relationship stuff. So obviously we thought he needed a puppy.

 

We couldn't separate them.

 

and couldn't separate them, they're brother and sister, but we didn't want two puppies, so we made him buy one puppy and we bought the second puppy and her name was Grace. And she was a doodle and she was absolutely amazing. But apparently the doodle landscape, the doodle landscape is a billion dollar organization. It's a billion dollar industry.

 

Yeah, I think there's quotes from the scientist that kind of created the breed that wishes he'd never done it.

 

Yeah. But I don't know why. They're so sweet. So you have like your golden doodles, your labradoodles, your Bernadoodles. Everything doodle. And what's comical to me is that the doodle culture, they're really upset because who's the governing board of dogs?

 

George McKenzie (18:38.608)

everything doodle.

 

George McKenzie (18:51.894)

people at Westminster run that show.

 

AKC or something like that. I don't know. There's a governing board that determines whether or not you can be qualified as a purebred dog. And they have denied Golden Doodle that title of being a pure breed, which I mean,

 

much at every Thanksgiving.

 

George McKenzie (19:14.702)

That's a genetically manufactured dog, so I guess it can't be a pure breed. Are there any, though? I don't know, pure breeds.

 

But it could... What? Yeah. Yorkshire Terriers. All of the dogs that you see on Thanksgiving are purebred dogs. Right? They're only...

 

They were found in nature. They're all red.

 

They were bred purely with each other, which the doodle people were so upset that they were comparing the governing board as Hitler-esque because of their rules.

 

Yeah, I guess people really take it seriously. Why? They want a doodle to win, best in show? Is that the...

 

Alicia McKenzie (19:53.986)

They really take

 

Alicia McKenzie (19:59.358)

Yes, yeah, absolutely right they want to be recognized as a purebred animal

 

I want to be recognized as a king. And just, you know, why can't we all just have a dream? Maybe this doodle has a dream to be best in show.

 

I like that for you.

 

Alicia McKenzie (20:17.494)

No, but this whole like the doodle boom, the industry, they have conferences. They have conferences all over the place and it's like this whole culture.

 

Yeah, the older I get, the more I realize there's so many fringe cultures. are ways to make money for sure, but just interest people have. Like, I'm still fascinated that there's the, I'm sure you've seen the videos of people that do the like equestrian on the stick, like the horse stick. Like, I guess there's something for everyone.

 

Thanks.

 

Alicia McKenzie (20:50.91)

There's something for everyone.

 

these doodle people have come together in conferences.

 

They have conferences, they do it all. It's just this one big doodle community, but let's take it a step further. Let's look at the dogs of TikTok because from what's really, I'm sad at how TikTok has sucked me in. TikTok taught me, but there's dogs earning real money on TikTok. right, so the number one top earner on TikTok for a dog,

 

is a Pomeranian with 20 million followers pulling like $11,000 to $20,000 a post. About brands, it's like dog friendly brands or like just.

 

What's the post about dog food?

 

George McKenzie (21:36.556)

Here's my Pomeranian. She loves Louis Vuitton.

 

But then like cross platform posts are earning up to $25,000 a post. That is wild. That's wild. That's the number one top earner.

 

The only dog that should get any fame on Instagram or social media should be the dog that was in Deadpool 3. That one. That's the only one that's a true selection.

 

my-

 

I betcha he has a... I betcha he has a...

 

George McKenzie (22:03.47)

Thousand billion percent. It's probably how it got on there.

 

100 % has a TikTok. But you're talking about like the top

 

Or Beethoven. Beethoven should also have some.

 

You know who should have a TikTok page? The dog from Sandlot. was He's probably dead. stop.

 

Yeah.

 

George McKenzie (22:21.294)

He's like 30 years old.

 

You don't know that. Huck is going to live forever with red light therapy and peptides.

 

Okay, we'll see.

 

But I actually, my entire goal with Fitzgerald Grant III, he's going to have a TikTok page and he's going to live his best puppy life for the world to see. Since I don't like putting my kids on any social media, I'm going to put my dogs on there. Are you down for it?

 

I'm along for the ride and whatever you're do in life, baby. I'm here.

 

Alicia McKenzie (22:53.838)

All right, that was my fun little jargon. moving on. Jargon? Jargon? What is that noise?

 

be killer I don't know

 

Yeah, we have a big bee problem.

 

You better be leaving. That was good. think someone's vacuuming.

 

Okay. All right. Moving on. So the exit plan that nobody talks about, apparently selling a company and staying married is hard to do. this the thing? We did it a couple times.

 

George McKenzie (23:20.97)

Yes. Yeah. Yeah. I just think it's an interesting topic because I talk to people about this a lot. Like when you exit, it's really hard because you're caught up in the emotion of it, right? It's, it's normally a financial windfall. So you're super excited about, you know, the financial aspect of it, that most of your wealth is probably tied up or your net worth is tied up in the business. And now you're getting that.

 

Also.

 

George McKenzie (23:47.886)

So it's a relief and you chase it and you're kind of excited about it, especially if it's your first one. But it comes at an emotional cost sometimes, especially if it's one in which you exit the company. So if you exit, let's say, private equity, but you're still engaged, it has a different ring. But if you sell and then exit the business or it's a part of a roll-up or goes into a strategic, it can be...

 

almost as if you lost a part of your identity and who you are. And I think a lot of people aren't ready for that. So when you do that and then, you know, something you've cared about that was your a hundred percent drive for the five, 10, 15 to whatever, how many years you've been in it, it's been the thing that's driven you and the thing that you get up four in the morning and you're solely focused on. And then one day that's gone and you have a lot of money, hopefully. And that

 

Yeah.

 

You know, you can have that to show what you created, but what do you do next? And then I think that sometimes that's hard on marriages because then you're like, all right, I don't know who I am anymore. And I don't know what I'm supposed to do. And then the opposite being, you know, now that you have this wealth, you know, so that's the emotional impact side. And then the other side is, you know, you were grinding it out and you're living, you know,

 

probably below your net worth because most of your net worth isn't liquid, it's tied up in the business. And then now you have this liquidity event and you start to expand your lifestyle, right? And then some people have a hard time budgeting that or having this, being on the same page of the lifestyle you want now versus the lifestyle you had before. Change is hard for everybody. So that's more around the top.

 

Alicia McKenzie (25:38.678)

Interesting. So how do you think your mental picture of you and yourself and what you do, how did that change after first exit? Like DBS felt like our baby went to college.

 

Yeah, I used that analogy when we did it. But I think it was more of, you know, when I look back, it was probably more than that. It was like your, it's like your baby got married, moved to a different country and started its own family and didn't talk to you anymore. I mean, that's true, right? And it's, yeah. And then eventually you didn't want to be a part of it anymore. And it's crazy to think that. And then you still remember all the times.

 

You no say over it, though you sort of-

 

George McKenzie (26:23.618)

before and you want to go back to it. You're like, I wished I could go back to that time. It was great. Great. But it's hard to recreate the past. So it's interesting. It's just very interesting to think about that. for some people, it's not like that. I'm sure for some people, it's easy. It's, hey, it's an asset. So I created this asset. I sold the asset. I have the equity. I have the liquidity. And now I'm going to create another asset. I'm going to do something different. I'm going to do this, do that. And then everything's just asset creation versus

 

That was.

 

George McKenzie (26:53.816)

pouring yourself into it.

 

Do you think that the first one hits a little different though?

 

It depends. think it all depends. Some people like you raise capital even in your first one. So you know going in the plan is to exit. I didn't.

 

But you never raised capital. That's what I mean. think for DPS, your goal was never to sell. It was never to sell, even when you were still, even when you were fielding offers from companies looking to buy you, that was never in the cards until the numbers started getting bigger and bigger and bigger. And we're like, this might actually be a thing.

 

That's the start,

 

George McKenzie (27:35.906)

And then you had enough partners involved that, you know, the numbers got there and everyone's like, Hey, this, this makes sense.

 

It made sense, but that was never the goal. think that's the difference, right? If you go into a company with the goal being to sell, you look at it differently.

 

But I still, I'd be interested to talk to, and I've talked to some other founders that have sold and it's similar. Like you have this moment where, you know, everything happens and now you're not a part of it. And you just, you you've self-identified as that person. Like I'm the CEO of this. I bootstrapped it. I funded it or I created it and that's who you are. And I've talked to someone that had a really large exit years, probably 20, 30 years ago. And, you know, he had the similar thing. It's like all of sudden, like, you know, I had a big, you know.

 

big number of my bank account, but it's like a random Tuesday and I'm drunk out on the lake because like I don't know what else to do. Like all my friends are still working. You know, I'm just like here.

 

Interesting. I wonder if that's like a market though. It'd be a very small market. It could be something.

 

George McKenzie (28:42.414)

I just think it's interesting for a topic that a lot of people don't talk about. It'd be interesting, you know, to at least get it out there so people that are starting their own businesses that are kind of figuring out like, I'm just going to start a business and or I'm exiting a business that, hey, I should put some time and effort into my mental health post. Like, what is it going to be like? Like, it's really easy to convince yourself that it's going to be great because of a number. Yeah. Right. And same with like, hey, you know, I have some

 

Yeah.

 

George McKenzie (29:11.36)

hesitations with the person that's acquiring me, but yeah, the number is great. got to go. I'm going to do it. It'll be fine. I'll work it out. It'll be good. And you don't put enough emphasis on thinking about what's next.

 

Yeah, I think that's a big question because then you've got people like the Poppy founder who's like doing gross, cringey TikToks in front of her new private jet. like, it's just, that what you want to be?

 

Yeah, that's exactly it. who knows, maybe five years she'll live to regret it. But you just don't know because probably you didn't. It's hard to anticipate what you're going to do, but have a plan for it or at least think about it ahead of time.

 

I have secondhand embarrassment for that. It's just the things. And I get it. You made a ton of money. It's great. But act accordingly.

 

Right. But it could also be like there's, you know, it's not just the mental aspect, it's that lifestyle aspect that you get married and you both have common goals, but then when money comes in and then you make new friends and you move to new places and then you buy lots and lots of stuff and then, you you change over time.

 

Alicia McKenzie (30:15.288)

think we like nice things. I do not think, I think most of our money goes to travel.

 

I'm not saying us specifically, but I've seen other people that do it, that all of sudden you had a BMW and now it's, you you have five Porsches or you have Lamborghinis and then everything has to be designer and you, you you're going to be seen at these events and you want to do like all the, not who you were before, but now you're pretending you want to be this other thing. then in marriages, sometimes, you know, one person wants to be the way they are.

 

No.

 

George McKenzie (30:51.926)

and the other person wants to now chase this new thing. understanding or trying to get ahead of those things and have the conversations and think about, do we really want with the liquidity that comes from this exit? What do we want to be? What are we trying to do? Because I think that also impacts the mental aspect of it. All the conversations I've ever had previous to thinking about this, a lot of people, it's all about the exit. How awesome it's going to be and how to make the money and...

 

Yeah.

 

George McKenzie (31:20.874)

How do you position your company for exit? How do you do all these not a lot of conversation of, you as a person and your spouse and your family, how are you going to do this? I think it's similar to lottery winners, right? think most lottery winners have terrible lives because they don't have a plan for it, just euphoria of I won and then they go crazy.

 

So how would you grade us on a scale of A to B? A to B.

 

I think we've been B2C, depends. I think I learned a lot. I think we've learned a lot.

 

For sure. I think we've learned what we want and what we don't want over the last 15 years.

 

Yeah, exactly. think you go through cycles, but as long as you communicate and...

 

Alicia McKenzie (32:08.95)

But it's easy to fall into that trap, especially living in this area, like the Washington, DC area, DMV, DC, Maryland, Virginia. Like you cannot throw a rock without fucking hitting a millionaire. Like it's wild living here. But I think you and I have a pretty good agreement on what we want, what we're willing to spend money on. Like we spend money on experiences, right? Like Napa. Yeah. Beach houses. Like we want our kids to experience things. We don't want them to get used to

 

getting things, to have things, just to have it.

 

You're only on the planet for so much time. All that stuff you're not going to take with you and you probably won't even remember. So it's really, you know, what can I do? for me, I prioritize my time with you and my time with our family. That's what is most important to me.

 

Yeah, and your pickleball.

 

I like to hang out with friends and I like to, I want to have some sort of exercise because I want to live long enough to be a productive grandparent. That's my goal.

 

Alicia McKenzie (33:09.58)

Yeah. Cool. Yeah. So I mean, it's the exit plan that nobody talks about. Great. You sell. So then what?

 

Yeah, exactly. Now you've sold. What are you going to do?

 

Do you keep working? Do you want to do it again? Do you want to try to recreate exactly what you did? And plot to West, can't. There is no recreating your first company. It's not going to happen. No matter how much you try, the landscape is different. The economy is different. The technology is different. You can't do it. So I would say get that out of your mind. How do you move forward?

 

Yeah. And then, you know, have a plan with your spouse and family of like, what do you, what do you want to do afterwards? Is it, I'm going on a year long vacation or, you know, we're moving or what is it going to be? And, you know, making sure that you have, and I think it all goes back to that dialogue. Almost the chat GPT thing from the beginning of this pod is, you know, have the honest conversation. People are uncomfortable sometimes talking to other humans with, you know, vulnerability and exactly what you do want.

 

And we get too much into, what does this other person want me to say? So, be frank and honest. Why are you looking at me like that?

 

Alicia McKenzie (34:17.742)

I'm not watching it.

 

Yes, you are I can see it I could feel it

 

looking at me, swan. Yes. All right. Good talk, babe. Yeah. From the heart. Deuces. All right, we're out.

 

Hmm.

 

George McKenzie (34:29.794)

Strong power.

 

Peace.

 

Alicia McKenzie (34:37.388)

Thank you for tuning in to Mary to the Startup. We hope you enjoyed today's episode. If you did, please take a moment to like, rate and subscribe to our podcast. Your support helps us reach more people and keeps the conversation going. If you have any questions or topics you'd like us to cover, drop me a message. I love hearing from you guys. Until next time.

 

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