5 Ways Company Retreats Transform Your Business

In this episode of Entrepreneurship Simplified, host Mike Michalowicz and co‑host Amy discuss why company retreats have become essential for hybrid and remote teams. They begin with light‑hearted banter before moving into a story about a disastrous Colorado hike that illustrates what a retreat should not be. The conversation then shifts to the core benefits of retreats: rebuilding human connection lost in remote work, fostering community, and aligning values. They share concrete logistics – quarterly short gatherings versus an annual multi‑day retreat, choosing Airbnb houses versus hotels, and accommodating different personality types with downtime. Amy and Mike recount memorable retreat moments, from the “Great Pumpkin Blaze” and THC‑induced back‑pain relief to the “Dumb Olympics” games, highlighting how shared stories create lasting bonds. They explain how retreats surface and refine corporate “immutable laws” (e.g., “no dick allowed”) and evolve into inclusive values like the “No Bro Show.” The episode also covers structured creativity exercises such as silent paper‑riff brainstorming for book titles, and how virtual retreats can incorporate scavenger hunts and breakout chats. Finally, they touch on broader business insights about incentive alignment, using dating‑app models as an analogy, and tease the next episode on mental health. Throughout, the hosts emphasize that retreats are not vacations but purposeful gatherings that blend work, play, and community building to accelerate business growth.
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Entrepreneurship is hard, but the process can be simplified. You can achieve success faster, sooner, and easier. I'm Mike Michalowicz, and I'm on a mission to eradicate entrepreneurial poverty. My goal for this episode and every episode is to serve you on your journey. Let's start right now on Entrepreneurship Simplified. I wanna welcome our audience to Entrepreneurship Simplified, and, uh, Amy and I do feel like news reporters holding this.
I need my notes.
Do you ever notice there's like a news voice? Like, this is, uh, Johnny Storm, and I want to tell you there was an abandoned hiker that was abandoned by his group. Like, isn't that a funny voice?
It's a crazy voice, and I don't know why anybody would be, you know, drawn to that voice.
Do you think that they talk like that at home? Hey honey, uh, I'd like to get a—
I now have images in my head I never had before, but maybe that is how I'd like to get a martini with a twist, uh, before dinner this evening.
Is that appropriate? Uh, tell me, can you deliver by 5:30 PM? That's be funny.
That'd be crazy.
I'd hate to be married to a news reporter.
I know, me too. Oh my gosh, I bet Krista feels a little bit like she's married to a news reporter though, does she not?
Did you say a douche reporter?
No, I said a news reporter.
Oh, news. It sounded like she is married to a douche reporter. I also find it funny when a news reporter is speaking and they pronounce someone's name, but they go into the pronunciation in the native tongue of that name.
Yes.
So I can't do it, but you know, say it's—
eyes, R's or something like that.
Like, uh, we have a news report in. This, uh, gentleman, Rodrigo, from— you know, it's just very funny.
You love to say Rodrigo.
I love it.
Hey, you're a birthday boy today, mister.
I am.
How do you feel?
I feel 53. I worked out this morning.
Yeah.
I feel great.
Good.
I love it.
Good.
50s, you know, it's the beginning of the 50s.
Yeah.
Been good.
Yeah, they've been good.
Been good.
Good.
And I wonder if this is true for most people, that as you get older in general, does life, the decade get less tumultuous? I don't know.
I wonder. I recently had dinner with a bunch of friends from high school. Girls that I don't generally get to see. They're really more like friends of friends kind of a thing. So, but we all got together, all women, and I was like, so, 50s, what do you guys think? You loving it or is it kicking your ass? And, uh, half of us were loving it and half of us it was kicking our ass.
Interesting. So what were—
so this is what I came up with. So the ones who were loving it are not yet in a position where they're taking care of elderly parents. Uh, there you are. Or their parents may have both passed, or they are still independent and living well. Yeah, on their own. And, um, health for themselves is still quality, is still quality. And, uh, children, um, settled or doing well.
That makes sense.
So those were like the three factors, the three big factors.
And so let me just do the other side, the people that were not enjoying the 50s as much, their own health is degrading?
Yeah, or they had health challenges that they're overcoming basically.
Okay.
And had parents that— parents or even one friend had elderly aunts that she was caring for. And not necessarily even in her own home, it's just part of your energy expenditure daily, even if it's just mentally and emotionally, got to check on Aunt Eileen, how's she doing, da da da da, you know? Yes. Uh, that kind of thing. It's— I guess that's where the energy pulls are.
Yeah.
And that's the difference for people.
That's a great point. Yeah, that's a great point.
Yeah.
To me, just the, the '20s were more tumultuous. This felt more like a roller coaster. Now it's kind of longer.
Yeah, slides. Longer slides.
Yeah. And then yay for the longer slides. Yeah, exactly. And what I try to do is when you're on the up part of the roller coaster ride is try to really enjoy the views. And if you can, tell the operator, slow it down. You know, when you go—
don't make, don't make any moves.
And when I go down, let's go fast and get it over with, you know. I want to go back Yeah, so I love it.
That's true.
We're going to talk about today about retreats.
We are. But, uh, before we do that, I want to introduce you, Mike Michalowicz.
You are— I always cut you off. Sorry.
It's okay. It's all right. I just want to tell our audience who they're, who they're listening to. Yeah, who they're dealing with. You are Mike Michalowicz, the author of multiple business books and a great supporter of entrepreneurs. It's your mission to eradicate entrepreneurial poverty.
Entrepreneurs rock. Yes, I almost have, uh, such a lean toward entrepreneurship. I want everyone to be an entrepreneur, and that's not necessarily appropriate. Like, you're—
I've heard you say that to, like, my husband, you know, and I'm like, I don't even know what I would do.
I was thinking Chris, like, uh, he's made a job transition. It sounds like he landed the dream. He landed a dream job, and I wanted to call him up and say, dude, it's time to start today. Um, and it's not appropriate for everyone because, A, it may not be your style, but other times it's just not part of their life plan.
Yeah, or their makeup even. Yeah, like, and I keep thinking, is Mike trying to fire me? Is he trying to get rid of me? He never. Well, you know, that's where my brain goes.
I know, I know.
Mike's trying to fire me. He doesn't want me here anymore. He's telling me to get out, get on my own, support myself.
My visualization is like you trying to leave and I'm just clawing at your one foot and you're kind of dragging me along. My father, did your dad ever do that with you? I'd sit on my dad's foot and he'd walk.
Yes.
That was so much fun.
Yes, it was so much fun.
That's like the best thing, you grab under a leg and whoop.
Yeah. Hours of entertainment. And they had their crushed feet, the poor men. All right, yeah, so today we're gonna talk about retreats.
Yes.
And I don't know if you saw this news coverage, Mike, but there was a team of 15 coworkers in Colorado who went for a team retreat and did a hike. They left one of the team teammates to finish the summit push alone.
Okay, I heard a little about this story, but I don't know enough. So that means they were trying to climb to summit and they just all decided they were giving up?
Yeah, but they were kind of like, you know, 3, people together here, 2 people together here. They were all started off together, but you know, but some people— yeah, no, not exactly quit, but you know, the paces are a little bit different. Okay, so a bunch of them got to the top and were starting their descent. Another one was— had not yet made it to the top, and he was still heading up, and they kind of continued down the mountain thinking he would just be right behind them, kind of thing, I presume. We don't know anything about this company or what their intentions were or anything, so I don't want to say anything that's not kind to them. But the problem was he became disoriented coming back down because his co-workers removed the markers for the trail. He pin dropped his location to his coworkers around, and then a second pin around 4:00 PM. At that time, they're like, "Hey, hey, dude, you're in the wrong direction. Go back up and come back down the other path." Oh. In that time, he got disoriented, a storm came in, he lost cell service, and unfortunately, they did not report him missing until 9:00 PM. He spent the night on the mountain in the severe weather.
Oh my God.
He finally got cell service the next morning and was rescued the next morning. But can you imagine going back to work with those people the next— my God, the next day, or whenever it is that you return?
I bet she's all finger-pointing.
Oh my gosh.
I mean, he's pissed at them.
We thought he was with Sam. We thought he was with Lou.
Yeah, but like, dude, you know, you were supposed to be back by 2 o'clock in the morning. We, we called in at 9. You should be grateful.
Yeah, yeah, yeah, exactly.
Oh my God, that's a retreat gone—
yeah. So that's not exactly what you're after with a company retreat. That is not a great example of what happens at a team building exercise. That's the opposite of team building.
I hope everyone's in therapy.
I know, I hope everyone's in therapy now too. But we, we believe—
we're proponents of major proponents of retreats.
Yeah.
Uh, and particularly in the current or the new environment of business and how they operate. Yeah, post-COVID, predominantly. But it was interesting, pre-COVID, if I was an employee of a company, I desired or wanted flexibility in my work schedule. I desired or wanted the ability to work remotely. Post-COVID, I expect it.
Yeah.
And there's a lot of these news stories, and maybe we'll break into them, of how companies are trying to force people to come back to work and you got to be here. The question I always have myself is, why does Amazon or whomever, I'm just picking a random name, mandate employees come back to work. There is something powerful around human connection. There is rapport and trust that's built. There's an exchange of knowledge and ideas that if we are working in an isolated environment would never happen. What it used to be is we go into maybe our office and that was our isolated time, but then somebody could peek in And you have rapport, or it's the water cooler. What happens in those moments is trust is built. It doesn't, we don't have to always be talking about business. One of the moments I said, oh, our company's got it. This was a few years ago. I was walking in and I arrived late to work. You were here and so was Aaron and Jenna and Corday and Kelsey. I think Jeremy was here. It was a large group and everyone's talking about as a group, some social activity. Now the owner guy walks in, and what happened? Everyone says, hey, Mike. And the conversation continued unabated. I was like, oh, we got it.
Yeah.
It used to be I'd walk in, and now the cat's here, all the mice scurry. Oh, well, we were working.
Yeah, back at it.
And that's a problem. We need that social connection. Well, with it, we have the grease for the gears, right? And things just move. Without it, we don't really get each other.
Yeah, we get disjointed.
Well, in absence of having an office space where people are connecting, retreats are the new connection points, right?
Right.
So we do them. I believe in them extremely much. Extremely much. I believe in them extremely much.
I believe in them extremely much.
I much extremely believe in them. And the opportunity is just to connect with each other as humans. Conversely, it's not a party. It's not like, hey, let's just gather and vacation together. We have activities around the business so we can kind of centralize our thoughts and move the business forward as a unit. There's certain issues that everyone can give perspectives on and we bring those up, but we're also deliberately connecting and spending time together and breaking bread together, waking up in the morning and hanging out in the morning, cracking coffee. You see a different person too in those environments. So retreats are— So important.
So huge. Yeah, we've had, uh, quite a few. Um, just to jog your memory, we've been to Nashville, Tennessee. We went to Bear Creek Mountain Resort in Pennsylvania. We did a trip to Cape Cod, New Hope, Pennsylvania, Croton-on-Hudson, and Mount Kisco, New York, were the last two that we did. I've had some fantastic memories from those, like, um, flying to Nashville. That was great. We were a smaller company then, so it was not a huge thing to, to get us all somewhere with a little bit of distance. Um, but that was so great just to have like the different perspective and, you know, really be out of our, our typical zones. Um, Nashville, one of the first, uh, retreats we did was just so much fun. We had such a, such a great team and so much laughter between us.
Yeah, yeah. And Jeremy was able to show off his skills. Yes, I loved, uh The one in the mountain, it was a ski resort.
Yes, I was thinking of that one too. We were freezing.
Freezing. And we didn't ski.
No.
But I remember Liz there and we're doing that silly game where you hold the thing on your head and we're screaming at Liz. Like I said, horse or something, her favorite animal on the planet. We're like, "It's got four legs!" And she's like, "A dog!" We're like, "No! Bigger!" She's like, "A ferret?" "That's smaller!" Just these little stories come out.
Yeah.
What I found, the greatest form of human connection is shared stories. I call them the remember whens. Tracy's a great friend of yours. Judy is. Kristen, for sure. I strongly suspect when you get together with your friends, you say, "I remember when." Right? We do that as a team here. And retreats give you the opportunity to create those moments. There was one instance And there will be a drug reference here. So if that's a trigger warning, I want—
You want it out there.
I want it out there. So skip the next minute or two. We went to, it was in New York. It was on the river, I think. Right? And we went to the pumpkin.
Oh, we went to the Great Pumpkin Blaze. Great Pumpkin Blaze. On the Hudson there.
The Great Pumpkin Blaze. I tweaked, I said something with my back and I had difficulty walking. In fact, Jeremy and I were playing tennis and I couldn't even move.
I remember you were hurt.
I was hurt. And I remember a few times we're walking through this pumpkin blaze, I just had to kind of squat down and stretch my back. And my son was even there. Jake was there, I think.
I think he was, yeah.
Yeah. I'm like, dude, I need you to actually help me stand up. I can't. Jenna is like, oh, I have these THC things, the gummies with weed in it. She's like, take it. I'm like, that gets rid of the pain? She's like, yeah, totally. I pop it in. 5 milligrams is intense. This thing's like 25 milligrams. All of a sudden it's like, wow.
And you're standing amidst 10 hours of jack-o'-lanterns.
Oh my God, pumpkin's talking to me! What's going on? Admittedly, back pain was— I don't know, it's still there. I was oblivious to it. I'm like, yeah, whatever.
Yeah, there's pain there, it's okay.
Whatever. I am so lit up, and we're walking around. My son's there, thank God, and he's kind of guiding me through this thing. We get back to the car, and because there was enough of us, we needed 2 or 3 vehicles.
2 cars, yeah.
I get in the car And we're sitting there and one thing that happens when I have THC pumping through me, I lose the concept of time. Something that's like 30 seconds seems like an hour and an hour can happen in 5 seconds. So we're sitting in the car for perhaps 5 seconds. I'm like, why are we still sitting here? I'm like, it's so long. Let's just go right to Kelsey. She's like, we don't know where the other people are. I'm like, they already left. Let's just go home.
So let me tell you, I'm in the other group of people.
Yeah.
And we get out through the— because of course they funnel you through the gift shop as you leave. Of course.
Place.
And we, we get out to the parking area and I'm like, did they somehow get behind us? Are they still in there? We're waiting, we're waiting, and we're waiting. And no way in my mind at all did half of our team leave us without telling us that they left. This is like the mountain thing. This is our company's version of the mountain.
And there was one idiot who led the charge. It was me. Because Kelsey's like, no, we should stay. Whoever else in the car, like, no, we should stay. I'm like, no.
I think it was finally Aaron who's just I think those fuckers left us.
Yeah, and she's totally right. And I was the fucker. And so here's the other thing. We get back, so we laugh about it. We're all joking. It's like, oh my God, I was still lit up. Then we're at the campfire and I think everyone's stoned. I think I'm not the only person stoned. I think everyone is and no one else is because I had this THC. I'm like, you're wasted. And I start blaming people. Oh my God.
Hysterical.
Never again.
Never again.
It did help with my back though.
Oh God.
Yeah, and now my back is amazing, so maybe it fixed it.
Yeah, you might— that might, that might have been the trick. Yeah, the good thing about our retreats is though, like as you said, okay, so the retreat gives companies who are doing a hybrid or a remote location thing an opportunity to get themselves back together again, but it also— within the retreat themselves, there's this balance of work and play. Yeah, which, okay, so there's our play with the, the Blaze and the, and the game with Liz and her not getting the answer right. I laughed so hard that night. I found out what kind of person Lisa was. Our old colleague Lisa was at that one, and she's the most competitive the most competitive thing in the world, and she was teamed up with me, the least competitive thing in the world. And it was— I had tears pouring down my face.
Was this the Dumb Olympics?
This was— no, that was that game where you had to guess what the other person— and she was screaming in my face like a Marine drilled sergeant.
Yes, that's Lisa.
That's Lisa. Hysterical.
And so supportive too. We did the— I called it the Dumb Olympics.
Yes.
You came up with these things. And so one was put an Oreo cookie on your forehead and get into your mouth.
Yeah.
And Lisa, like, I am owning this.
Yeah.
And she did it.
She did it. She won everything. I think she took it all.
There was another one, like, with whipped cream.
Yeah.
I remember— I'm like, what is this?
Getting the bubblegum in the bottom of the— getting the piece of bubblegum in the bottom of a pile of whipped cream and chewing it and getting a bubble blown first.
That's right, right, right, right. That was the race.
Yeah.
I remember, like, an hour or two later, I'm like, what's that smell? It's like bad sour milk. My stink beard.
From all that whipped cream in your face.
Yeah. And I thought I washed it out because, you know, everyone wash your face. I didn't use soap. Oh my God, it was rotten.
Rotten.
So much fun.
It is.
So that builds connection. We also— you find the values. So talk about Lisa. She's got to be— she excels in a position of competition, um, but also she's not one of those competitors that like, if you don't win, you suck, right? She just wants to win.
She just wants to win in that moment. It's all good and fine afterwards, regardless of the outcome, right?
And so what we have to do as a team is say, where can Lisa express those values that she has?
Yeah.
You saw the matriarch skills that's inherent to you. Where can we use that to express in the business and so forth?
Right.
I saw that, you know, Kelsey was very clear. She's extraordinary organizing.
Yeah.
And ensuring that everyone's included and everyone is in a joyful state doing what they want. So it shows the values as individuals. We also identified our corporate values, and this is something I have to rescind. So in one of my books, I think it was in The Toilet Paper Entrepreneur, I talk about immutable laws. Now immutable laws and corporate values are synonymous. The only reason I used immutable laws is I wanted to point out that these are ever constant. They're non-changing. One of my immutable laws personally is no shit allowed is the term I use. And what that means is I'm not going to deal with people who are dickish, rude, take advantage, and so forth. And I won't accept that for myself. I've done some dumb things in my life, and I've fessed up and apologized. Yeah, that was a dick move. In fact, recently, Ron Greenberg, he's our wealth manager. Yeah, I made a joke to him and some other guys, uh, about Ron, and, um, it wasn't funny, and it was almost like a little bit on the dickish side. So I immediately I mean, next morning I text him. I said, "That's not my value." And I was trying to be funny. And as I reread this, it was kind of like meanish. So I'm like, "I'm really sorry. And I hope that this doesn't compromise our friendship." He's like, "Are you kidding me?" He's like, "That's like what we do." I love that. But I compromised an immutable law of my own.
Gotcha.
So lesson one here is a value that's so important to you that when you even violate yourself, you start kicking yourself over it. That's a value, an immutable law. What I said in the book is we need to build an organization around it. Well, I want to rescind that because if I find everyone that has the same values of me, we start getting a silo effect. At our retreat, I can't remember which one it was in particular. It was one I think where we did the cup races where there's cups and you had to get through.
Yeah, yeah, yeah. That was like 2 years ago.
Yeah, it was a beautiful location. We're there and I said, let— or Kelsey said, let's talk about the company's immutable laws. And I said, well, no dick allowed. And I think it was Jenna who said, can I say something? I'm like, yeah. She goes, that's kind of bro-y. Like, she goes, I know where you're coming from and I agree and it's consistent with me, but I'm not about the bro. And I was like, well, I'm not about the bro either. And it was like, oh my gosh. And it came to a new collective value we call the No Bro Show. It's on our wall here. Is that we're not those type of people. You're not gonna have the jet, the cheesy jet in the background and the Lamborghini.
Right.
You're not gonna see me, Occasionally I do flex. I do flex occasionally. But you're not going to see me wearing like, you know, you got to be strong and powerful and pumping some steroids. Right. You're not going to hear me saying you got to hustle and grind and compromise your family and just work like an animal. I don't believe any of that stuff. It's very bro-y. We now have a new set of values that represents our collection. What's interesting is I always thought, well, that would diminish who I am. But no, it's an ex— I don't— you and I don't change. Our values stay constant. But this is an expression of a collective. It's actually expanded who we are. Right. It triggers a more diverse notion and belief set. It makes us more inclusive.
Right.
So your corporate values will change. That's what I was wrong about. I thought they were constant forever. They will change and expand. And the more diverse your organization is, there will be this collective thing. Instead of building culture, we need to build community.
Mm-hmm.
We live here in Butte. This isn't like, oh, it's got to be people that are 50 years old that went to Butte High School. And you gotta be white. It's— we have all different religious beliefs here, different skin colors, different backgrounds, uh, different languages as your native tongue, people of all different ages, and we all have this common value. We love Boone. We care for this town. That's community. And because of the diversity, there's this richness here.
Oh yeah, multi-layered and deep.
And deep. There was the First Friday they celebrate. I remember walking through here, I'm like, yeah, yeah, I walked by there was a Mexican restaurant and they were doing all these traditional dances there and the music was blaring. It was actually distorted so loud. And you see people of all different backgrounds getting into it. And then you walk down, there's an Indian and then I think an Iranian place and a partying out. And just the stir of the pot was so rich and nice. Yeah, that's what I think we— I know now we need to encourage in our company. By shared values.
I love it.
Build community.
Yeah.
Creativity. We have some great exercises to brainstorm.
Oh yeah.
And honestly, I shouldn't say honestly, the reality is when we're working remotely or disparately, we have to work in our tunnels. But when we come together, we can tackle a big topic. We've created book titles. I remember Kelsey walked us through an exercise. It was a— this is a great brainstorm. You take a piece of paper. And you give it one piece of paper to per person, and it's a column or kind of sheet. And say the brainstorm is around book titles. You write down one book title on your sheet, and the person to your left writes one title. So each sheet now has one title on it. Then you pass the document to the person to your left, and they look at what the prior title was, and they riff off of it.
Right.
And you pass it around. It's this silent brainstorm, but there's this natural expansion.
Right.
And so we came up with with 8 people, 8 times 5, 40 or maybe more titles and variants, and one of them became our book title.
Yeah, yeah. It's a brilliant way to—
Really cool creativity.
It is really cool creativity. And part of— So a big part of our retreats is generally a brainstorming session. We're working on something, an idea for a new product, an idea for a new book, an idea for a rollout, whatever.
Yes.
Yeah, marketing. Um, and for me, there's a couple things. I love that we do that because my job generally doesn't entail those things. I'm not in marketing, you know, I've got my tasks that I'm, I'm working on, and you can get a little bit tunnel vision with what you're doing. And so for me to become aware of what another big overarching goal is for the company is really helpful. It ties me into what everybody else is working on. I kind of get the perspective of where their energies are going, where they may need support, you know, because I know that that's only part of Andrea's job, or that's only part of Jenna's job, you know, there's gonna— there might be something else that I might be able to take off her plate so that she can help roll this out or whatever. So it gets me out of this like very, very tunnel vision. Yeah.
Narrow space.
Yeah. Narrow space that I have. And the second part of that is that I really love how safe we make these brainstorming sessions because I'm not a creator. I don't, I don't flow creativity, you know, creatively like you do and Jenna does and Kelsey does. I think you guys can just like riff ideas off constantly. I mean, almost constantly it seems like you guys could come up with something new. That's not how I work. That's not how my brain works. And there are times when I've been part of brainstorming sessions and I've felt so It's like the first couple times I went and we had these, it's intimidating because like you want to contribute something of value.
Yeah, yeah, yeah. Don't be the silent George.
Don't be this. Yeah, exactly. But if, if you can't, or you just— I've been free to say, guys, I'm sorry, I just, I've got nothing on this one. Like, I'm just literally hitting a wall with this one. No problem. There's not even a blink, not even a, not a, not a look, nothing. It's just like, oh yeah, that's, that's how it is sometimes. And we and we roll on. There's no pressure. Yeah, it's, um, it's a very safe place to just be who you are. I think Aaron and I align a lot sometimes on what we feel like our, our strengths are. And it's funny, we're both like the admin positions. Like, give us a task and we'll go— don't tell us to make up a task. That's not the thing, I think.
So I have a different perspective. What I think is you and Aaron, in this case, contribute in such a unique different way. It's actually the best for the creative process. So you go through it perhaps more meticulously and more thoughtfully, where a Jenna or myself or Kelsey may be much more surface level, just yes and yes and, but it's very surface level. Um, and so what's nice about our organization is different minds process in different ways, and therefore you get different perspectives. It's much more expansive, right? So we have personal owner's manual under each person, and it talks about our styles of creativity, among other things, and the way we process stuff. And that diversity is a wonderful thing. I find also these retreats are very expansive in learning. One of my favorite retreats was in New York in that kind of glass house thing. Remember it had like that?
Yeah. Yeah.
And I think it was Izzy who gave us a training in photography on our phone.
Oh yeah, that was so cool.
So cool. And she's like, let's go out and take pictures. And I've taken pictures ever since radically differently, much better.
Yeah.
As a result of that, we learned something. Yeah. I used to make object in center.
Yeah. She's like, oh, rule of two-thirds.
Yeah, rule of two-thirds, right? Rule of two-thirds. Right, right. And, and, and blurring the background. These different techniques you could—
yeah, yeah. It's always been— it's always a learning experience too, which I've always appreciated as well.
Yeah. Let me just give some practical techniques to our listeners. We do them quarterly, but we do one extensive one annually. So quarterly we'll do there's a congregation, but usually it's at the office, or maybe we go out somewhere and we do a quick lunch, maybe an activity, right? But it's within the general facility of our office. Some of our listeners are purely virtual, so, um, you have to pick a location. But we do do them quarterly. Yeah, I think that's a good frequency. Annually we do an extended retreat where it's multiple days, right? Some businesses— I have a friend, Jason Snyder, uh, they have offices in the US and the Philippines, all over. Most people are still in the Philippines, so he'll actually fly to the Philippines and they'll spend a full week out there at a resort as a company once a year. And then their other retreats, because it's so expensive, are effectively done over Zoom. And so it sounds kind of weird to have a retreat, but over Zoom. We've done that with PFP out of necessity at times. But we integrate these activities, a fun activity, like a scavenger hunt. So it's like, for the next 10 minutes, run around and do this and come back and report. We had little breakout sessions where people were talking one-on-one about a life's experience. And yes, we do lose that one-on-one personal touch. Yeah. But it can invoke elements that don't come out of the traditional remote work environment.
Right.
So, right.
Well, for practically, I just wanted to, uh, offer this up too for business owners, entrepreneurs who are thinking about starting this with their companies. Um, some practical thoughts on, on how we do these. We usually leave on a Monday morning and we're back by midday Wednesday. It's not a huge ask of the employees. Most of our employees are moms, so it's a lot to, you know, leave your family for a couple days. And a lot of us are part-timers, so it's, it's a, it's a thing. It's a commitment, but you, you want to do it, and it's always worthwhile and valuable for all of us, not just for the company. It's really— it always ends up being a valuable experience for all of us. Um, we've started— we, we have stayed at hotels and and things like that. But we found that an Airbnb— we're a small company, so this is, this is feasible. Uh, we usually do an Airbnb that can accommodate us. As you said, Mike, it gives time for connection, uh, in the downtime hours. We get some nice homes. Like, we had a house with a tennis court, and, you know, we've had some beautiful kitchens. When Jeremy was with us, he was a professional chef, and he would do like a cooking class in the— and so a house in that regard offers up a lot of potential for connection, for other activities. We've some of our fun Olympics out in the lawns of these great houses and things like that.
So yes, yeah, we have 8 people in our company that go on the retreat, I think. And so we generally get an 8-bedroom or more house, so everyone has a private room.
Yep.
Um, that's not— if we— as we get bigger, that may not be doable, right? Um, I've been on retreats where, where guys shack up with guys and women with women.
Yeah, we had a couple of those.
So that, that can That can work too, but you gotta make sure people are, are comfortable with that.
Yeah.
And generally we've done everything on the East Coast, so we've done a couple flights, but generally driving distance from us.
Absolutely. And we try and keep in mind that it's, um, it's an energy drain for some people. We're not all extroverts, so that much time together, um, you do need to build in alone time, downtime. I know, like, that's a great point. We might work from 9 in the morning until about 3 breaking for lunch somewhere in there, so you get a little break there. Then maybe we quit around 3 or 4, and everybody gets a couple hours to like check in with home, journal, or go do what you want, or go find a place to hike, or whatever it is that you need to do. You can't, you can't have everybody tied to the, uh, yeah, to the business all the time.
It's too much of a drain. It was our last retreat, there was a, it was a mansion we stayed at, but it was out front, they had along the driveway like almost like a little meditation spot. Yeah, I found it and I went out there and I did my meditation practice. Like, this is amazing. All right, we gotta wrap things up, Amy, but we got news because we got a lot more episodes.
Yeah, that's what I'm saying.
And our GoPro is on fire. I don't— let me feel this thing.
Oh, look, feel at the bottom.
Yeah. Ouch. Okay.
Yeah.
So any news items?
Uh, yeah, we were talking about the dating app paradox. So we've got these dating apps, but, um, the problem for them is their goal and objective is to match you with somebody.
Yeah.
And make money from it. But once they match you with somebody, they're out the money because you no longer need to be on that, on that dating app anymore.
I was listening on the radio on the way home, uh, one day about doctors, and someone said something like, sick people make you money. And I sat and I was like, oh yeah, that's a good point. Do you know, this is true, in China you pay your doctor when you're healthy. When you're sick, you stop paying them because they— because you're not healthy.
Wow.
Right? Their job is to keep you healthy. It's interesting, in the US it's the absolute reverse, is you don't pay them when you're healthy, you pay them when you're sick. So interesting. Yeah, there— the question is, or the consideration is, is the client and the provider, the vendor, consistent in the rewards for the outcomes that is desired by the client.
Yeah.
If I'm being rewarded adversely to it, I may have a moral reason to be of service to you, but I have a financial incentive not to be.
Right.
We went through a situation where we needed lawyers, and, uh, I was talking to the lawyer and I said, listen, the longer this takes, the more money you make. And they said, "That is true." I said, "So what is the motivation to finish up?" He's like, "Well, our reputation. We want you to be happy with us." My conclusion is you want me to be moderately satisfied.
Right.
If I'm ecstatic, you didn't maximize the money you could make.
Right.
If I'm angry, you're not going to get a future client.
Right.
So how can you stretch this out far enough where I have just enough contentment? And I think that is where it goes. And I think these apps are the same. Yeah. Business owner thoughtfully structures their incentives to be consistent with the client wants, well, that's where your reputation excels and you're making money, right? So these apps, can they find a new way? Like, don't pay us until you find the love of your life, right? What if they did that, right? Um, maybe that's where the opportunity is. Now we're totally in alignment.
Yeah, I love that. Um, this— these notes point out that, uh, many dating apps like Hinge rely on a freemium model, offering free access with paid premium features. However, as apps Apps push for more revenue. Free users feel the experience worsens with desirable matches increasingly locked behind paywalls. So you got to pay for this next benefit, pay for this next benefit, to the point where you get to insidification of user experience. Who made that word insidification? Uh, let's see, uh, Cory Doctorow's concept.
I love it.
Insidification, yeah, where tech platforms initially focus on user experience to grow, but later degrade it in pursuit of profits.
Yeah. Yeah, that's the way it works. You know, to sustain a business, you must be profitable. So I get that, actually. I support that, right? You need to be profitable. But if you start off with a freemium model, which means your users can use for free, how you can— how you sustain that is by using— burning money that you aren't earning, right? So now you're going into debt. So now you gotta start making money, right? So you've seen this with Twitter, uh, and all these social media platforms that charge nothing, just more and more ads. They have to incentivize, right, so that they can make, uh, money. So again, I think the solution is what is the outcome the user wants, and can you align your incentives to be exclusively with that, right? Also, I think it's homogenization, meaning that these apps come out and they have a unique element. I remember we're preparing for this and Kelsey said it was a Bumble that was oriented toward women.
Yeah, I think she said Bumble was oriented—
unique, because everything's oriented to guys. There's a unique one, kind of kept their safety, uh, The women's concerns. It was perfect. And sure enough, over time, to sustain its business, it goes toward the general generic middle ground and it fades away. I will tell this, I will give you the opportunity here. If you're a small business owner, it's easy to be different because as a company tries to grow and sustain, the natural tendency, and we have to fight it, is to become more and more generic. So as a small business owner particularly, you have a great opportunity. That agility of yours allows you to really distinguish yourself in the market, but you also have the discipline then of clinging to that uniqueness.
Love it.
That's it today for Entrepreneurship Simplified. Amy, it's been a joy.
Thank you. Thank you.
Thanks for doing this. I want to ask our listeners, thank you for joining us, and would you be willing to subscribe to our channel if you haven't yet? Please, please, please, please, please, please. That helps us. And if you'd rate us and review us, uh, that helps us too. Uh, if you leave a comment, my God, then you're a god to us. So, so do that too. And no matter what, make sure you join us for next week's episode. What are we talking about next week?
Next week we're talking about, um, mental health. Mental health. Yeah, entrepreneurship and mental health.
That's gonna be deep.
Yeah.
All right, we'll see you all next week.
All right, bye-bye.










