Marketing School - Digital Marketing and Online Marketing Tips

Lessons From A Private Founder's Retreat

26 min
Feb 23, 2026about 2 months ago
Listen to Episode
Summary

Marketing School hosts discuss lessons from a private founder's retreat in Palm Beach, covering reflections on business growth over the past decade and future predictions. The conversation explores the importance of targeting large markets over niches, the impact of AI on jobs and universal basic income, and insights from successful entrepreneurs at the retreat.

Insights
  • The same energy required to build a business in a niche market versus a large market makes it worthwhile to target bigger opportunities
  • Most job losses currently attributed to AI are likely using it as a convenient narrative rather than actual AI displacement
  • Private founder retreats with consistent peer groups provide valuable long-term perspective on business and personal growth
  • AI and automation will likely create downward pressure on pricing, making goods and services more accessible
  • Premium brands can command extraordinary prices through scarcity and brand association rather than just product quality
Trends
Universal Basic Income implementation timeline predictions vary widely among business leadersAI productivity tools are making software development significantly more cost-effectivePost-COVID luxury membership prices have increased dramatically due to supply constraintsShort-form social media content can achieve massive reach even for older entrepreneursCompanies are using AI as a narrative for layoffs regardless of actual AI implementation
Companies
HubSpot
Mentioned as example of AI tools helping businesses use more of their data effectively
Crazy Egg
Neil's early company used as example of building features vs. full products
Google
Acquired Urchin which became Google Analytics, making web analytics free
Salesforce
Used as example of large TAM market with high-value customers
Zillow
Rich Barton's company mentioned in context of targeting large markets
Expedia
Another Rich Barton company illustrating the large market strategy
Glassdoor
Third Rich Barton company example of consistent large market approach
Heineken
Example of company claiming AI-driven layoffs of 9000 employees
Microsoft
Used as example of large organizations that move slowly on AI adoption
Coca Cola
Another example of large corporation that adapts slowly to new technology
Perplexity
AI company founder stated most job losses aren't actually due to AI
Anthropic
AI company founder agreed job losses are using AI as scapegoat
People
Tony Conrad
Early investor who taught Neil about importance of large TAM markets
Rich Barton
Zillow/Expedia founder who shared baseball analogy about market targeting
Syed
Retreat organizer who led the 'Then Now Later' reflection exercise
Walter
Marketing expert at retreat who got 21 million views on Instagram content
David Henzel
Attendee at the founder's retreat mentioned among the group
Genevieve
Mutual friend attending the Palm Beach founder's retreat
Yaniv
Long-time associate who organized conferences and attends retreat
Peter Thiel
Investor whose moderate AI viewpoint Neil agrees with regarding job impact
Quotes
"The riches are not in niches. They're after a really small market. No matter how much energy you spend marketing, it's roughly the same effort."
Neil
"The energy it takes to hit a single versus a double or triple or a home run is the same energy... so might as well go for a home run each and every single time."
Rich Barton
"Most of these job losses have nothing to do with AI. Everyone's just using AI as a scapegoat."
Perplexity and Anthropic founders
"You're paying 700 grand for the privilege. And don't get me wrong, it's a really nice tennis court, but that's a whole supply and demand thing."
Eric
Full Transcript
3 Speakers
Speaker A

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0:00

Speaker B

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0:01

Speaker A

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0:04

Speaker C

Today,

2:01

Speaker A

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2:07

Speaker B

All right, guys, we're going live. It's another episode of marketing school. It's 4am where Neil is. It is 7am where I am in Florida. And I'm here in Florida for a. For a founder's retreat. We're in Palm beach right now. Actually, Neil, the hotel I'm in, let's just say it is a rip off for what it is. I'm not going to name the hotel, but it's a nice hotel.

2:33

Speaker C

You're in the Surfside? Is that what it's called?

2:56

Speaker B

No, no, no, no. I'm in Palm Beach. Surfside is where Surfside is. That's north of Miami. But we're here for a retreat. You know, some of our mutual friends are here, like, you know, Saya, Genevieve, a couple other people at Al. Al. Don. Quilt guy. And so, yeah, it's David Henzel. I think he met him as well. So, yeah, it's a good group of people. We've been doing this retreat since 2018 or so. So we actually did a fun reflection. So actually, Syed was the one that, you know, planned this out. So it's been amazing. And, you know, he had us do a YPO exercise, actually. And I'll kind of talk about the retreat. You can ask questions around it. We'll talk about AI as well. We'll talk about marketing. I'll reveal what I can without revealing any confidential information. And we could talk about the retreat first. There's some other stuff to talk about

2:58

Speaker C

this week, but let's first go to the exercise that Syed had you guys do.

3:50

Speaker B

Yeah. So the exercise was. And this will be fun if you do it. You're not the type of person to do this, but it'll be fun if you do it.

3:54

Speaker C

Okay.

4:01

Speaker B

And I don't think he was actually the type of person to do this exercise before either. So it's called Then now and Later. So you basically reflect on 10 years ago and then. So 10 years ago, like, what were you doing? Where were you in your life? Like, how are things going overall? Am I making sense so far? Yeah. Okay. When you look at now, it's like, okay, how are things going out? Like, you're. You're 40. I'm 39 years old. We're around the same age. Like, you know, is our life. Did it turn out the way we expected it to be? How. How's it going now? You're married with kids. Right. And all that. Then you do 10 years out. Like, what's going to be happening in 10 years? Right. Are you doing like $2 billion in revenue, $3 billion of revenue, whatever.

4:03

Speaker C

Right.

4:37

Speaker B

And so it was really interesting because some people shared a lot of pictures, and I realized mine didn't have any pictures in it. And so everyone had reflected on their pictures. Cause you just look at your Apple photos, right? And I looked at mine. You know What's Interesting, Neil? 10 Years Ago, you, Yaniv and I were speaking at his conference. And at the time, yeah, there's a lot of things that were going really well, I think, in all our lives, but I think things were going really

4:39

Speaker A

well at that time.

5:05

Speaker B

I'm not gonna go into details, whether it's on the personal side, whether it's on the business as well. I think we're all on the very right track, and we just never knew where life would take us.

5:05

Speaker A

Right.

5:15

Speaker B

I'll just leave it at that right now without revealing anything. So I thought that was a great exercise because people really got to reflect. And the one thing I'll share with you, and then we can talk more about the retreat itself because, you know, literally I'm supposed to be playing tennis right now, but, you know, we're recording podcasts, so that's how committed we are to you guys. So, you know Walter, who's a really smart marketer, very good with copyright. I don't think you've ever met him before, but he has an amazing family, amazing kids. And this is public already, so this I can reveal. He's been recording these short form clips and posting to Instagram. One of them got 21 million views. I gotta send it to you. One's really funny, and the other ones were he's playing his kid basketball and his kid ends up beating him. Right. This is where the son surpasses the father, but he always makes sure to integrate his family and everything with everything. And, like, faith is first, family second. Right. That. That type of stuff. And so anyway, it just proves to you that, you know, despite you being like 40 years old, 45 years old, or whatever it is, exactly, you can still play whatever game you want to play. And he proved to his kids that daddy can get lots of social media views. They're like calling him, like, oh, you don't know anything about this. You need to have a good hook. He's like, bro, like, are you serious? Like, I'm a marketer, right? So I thought that was really fun. And then a lot of. A lot of NBA players, a lot of basketball players actually reached out to him after he put up that video. And everyone's like, man, that really brought me back. And so all that to say is like, that I think the Lesson for everyone here is like the then, the then now, later is a fun exercise. The other piece is if you can somehow, if you have kids, if you can do social media and really participate in your kids lives and try to bring them along with you, I think that's the ultimate reward. And I can see that with him.

5:16

Speaker C

So yeah, I've never done the, what is it called? Then now, later later, but I've done something similar. And I actually do something similar not every single day, but multiple times a week where I think about all the mistakes I've made from 24 years ago when I started as an entrepreneur to even 10 years ago or five years ago. And I break down what I would do differently to be much further off 10, 15 years from now.

7:02

Speaker B

Okay, so do you want to reveal anything?

7:39

Speaker C

Sure. Like any lessons, Some of the big lessons that I've learned over the years and I'll start really broad and then I'll get really specific. The first big lesson that I learned was from an investor named Tony Conrad. And Tony Conrad was one of my early investors. Uh, I think he was on the board of WordPress, which is automatic, right? The parent company is automatic. Uh, he sold a company, I believe to Yahoo. He sold a company to aol. He is al. Was also invest. He's a, he is an investor, but he's done well as an investor. I think he's been like uber peloton, you know, blue bottle coffee and the list goes on and on and on. And I remember Tony Conrad used to always tell me, you need a big tam. You need a big tam. And we would just shove it down our throat. Okay. And I remember some of my earlier companies I believed were companies like for example when we started Crazy Egg, it was a heat map tool and it would just show you where people click where they don't. And Tony would always say, you know, like, hey, you need a big tam. You don't want to just build a feature or two. And when you look at that product, at least the original version, it was just a feature. It wasn't pure web analytics. And back then there was a lot of detailed web analytics companies out there, including Google, bought Urchin Urchin, ended up turning into Google Analytics and they ended up making it free. But one little feature isn't a product and the bigger the market you go after. For example, when you think about market, most people think about quantity of people that it's applicable to. That's one version of tam. Example of that is toilet paper. Another example is, you know, CRM and being Salesforce, it's not applicable to everyone. But the people who it is applicable to can spend a lot of money on it, and it's worth a lot of money for. So from a dollar perspective, both toilet paper and CRM are big markets, and you can make billions and billions of dollars doing anything that's big. If you go after a niche, it's really hard to make money because the riches are not in niches. They're after a really small market. No matter how much energy you spend marketing, it's roughly the same effort. And I remember speaking on a panel with Rich Barton, you know, the Zillow founder, Expedia founder. I don't know what else he did. I think a glassdoor, it was his as well. And I remember Rich saying, if you're gonna, you know, whatever market you go after, it's pretty much the same effort, right? So if you're going after a niche versus a really big, broad market, it's pretty much the same effort from a marketing perspective. And the analogy that he used is the energy it takes, and this is a baseball analogy, the energy it takes to hit a single versus a double or triple or a home run is the same energy. You're still going up to the plate, you're still swinging, giving it your all, so might as well go for a home run each and every single time. And I personally agreed with it. And that taught me to stop building businesses in niches. And because all marketers are like niches, riches are in the niches, and it's just a big misconception. So that was the first big lesson that I learned. But it took me probably 12, 13 years to really understand and figure that out a little bit too long.

7:41

Speaker B

So what Neil's saying in business is absolutely right. The same energy goes into a business. You might as well go for a home run. But in physics, in actual baseball, it does take a little more energy to hit a home run than a single. So, yes, just wanted to flag that. But you know what's interesting, Neil? So I guess I'll reveal where I'm staying, because there are some lessons around where I'm staying right now, I think, from a marketing standpoint and the supply and demand standpoint. So we're staying at the Breakers Hotel in Palm Beach. So, you know, famous hotel, been around for a while. This. Is this a Flagger. Flagler family, I think, owns a lot of the properties around here. It's not a cheap hotel. So why. Why is it that the hotels are what's not cheap?

11:16

Speaker C

What's the cost?

11:54

Speaker B

So, I mean, it's public, but it's. So for the room that I'm in right now, I'll tell you the room I'm in and then I'll tell you the cost. I think this is like a 300 square feet room. Okay? Like, look, don't get me wrong, it's. It's a, you know, it's nice room. Like, look, they put Icelandic water in here and like you to put like they give you these Pellegrin water, right? For free or do you gotta pay for the water? It's free. It's free. You know, cocoa floss, the 15 floss that I use.

11:57

Speaker C

The.

12:20

Speaker B

Really?

12:21

Speaker C

Yeah.

12:21

Speaker B

So they have that in there. So they give you like nice things and all that. It's 2200 a night night for this room.

12:21

Speaker C

Okay.

12:27

Speaker B

For like 300 square feet.

12:27

Speaker C

Water.

12:29

Speaker B

No water view, dude. I have like, I can see like the courtyard. Okay, so that is expensive, right? Yes. And I thought I would get like a four season surfside view where it's like water view. It's huge. It's super modern and all that. Now I'm like, okay, guys, like, why is it so expensive?

12:30

Speaker C

Right?

12:46

Speaker B

And it's because it's a very legendary. It's the brand. Like, you know, you look at the people walking through, it's very. Have you seen Palm Royale on Apple tv? It's all about Palm Beach.

12:46

Speaker C

Have you seen it? I only saw like 10 minutes of

12:55

Speaker B

it and I couldn't keep it. So it is literally Palm Royale where it's like people are wearing like, you know, those really nice sweaters, you know, draped over them. And then like everyone's dressed really nicely. You know, it's totally that, like Yaniv and I were talking about. We're like, dude, this, this is so Palm Royale right now. Let me tell you this. The tennis court that we go to, we're like the membership pre Covid for the tennis court was 200. You pay 250 grand for the privilege, okay. Of paying 35 grand a year. So you don't even pay 250 grand for the membership where you can sell it later. You're not buying equity. Okay, for the privilege. Now how much do you think that membership is post Covid?

12:57

Speaker C

500.

13:32

Speaker B

700 grand? You're paying 700 grand for the privilege. And don't get me wrong, it's a really nice tennis court, but that's a whole supply and demand thing because, you know, with breakers, people want to be associated with the brand. It's legendary and all that. Right. And then the tennis court, because the supply is so low down, everyone wants to play tennis, they want to play pickleball and all this. That's how much it costs now. Right. It's no different than the LA Country Club that, that you and I have talked about.

13:34

Speaker A

Right.

13:58

Speaker B

The prices for these things, because they're scarce, just keep going up. But the difference is in la, you can sell it. You can, you kind of get to buy equity there.

13:58

Speaker C

I didn't know that you could sell it at LA Country Club.

14:04

Speaker B

I don't know about la, but the tennis club, my friend bought in for like 8,000, like pre Covid and then now it's worth like 50 grand and he could sell it.

14:07

Speaker C

Oh, that's good.

14:15

Speaker B

Yeah. So anyway, all that to say I, I thought that was interesting. But you know, there's, I think we did do a lot of presentations where people were talking about their business. So usually the agenda for these things, just so everyone knows, because I think live events, we've been talking quite a bit about live events. I think this is the type of live event that people should be considering because I think it's if whether you're in business or you're working for someone, it's good to have a peer group. And so our agenda for this one is tennis. I'll tell you the agenda today. I'll just make it simple. Seven to nine is solo activity. So typically I'm playing tennis with Yaniv and Walter and we have a tennis coach, right. And then at 9, we typically start 9 to 12. We do exploration. So Neil, you might be presenting on like a business problem and we maybe we go for an hour or so and we kind of go around sharing, you know, our experiences in the room. So everyone gets a problem to solve, right? And then, then we have lunch and then we go back and we do AI shares for about an hour or so. And then we play either pickleball, basketball or today we're playing cricket, which is, I guess, you know, your country plays that quite a bit. Right. So we're playing cricket today at Syed's house, right. And then we're going to have dinner and then we're basically done at 7pm every day. And you get alone time. Today it's a little more leisure. Like, you know, we'll go like, we'll hang out, but today we get to do some massages, we go to Syed's house. But that's how it's structured and it's like a three day thing and Then we try to go to like a different place every year. But I highly recommend that everyone, like if you've never done events before, you want to know how to do events, you should start something like this. Because this is when I did the then, now later exercise. This group was started basically 10 years ago or so and eight years, let's call it. And it stayed consistent. And it's really fun to see how people have grown over the years. So I'll just leave it at that. And I'm happy to share around the AI stuff too, but.

14:16

Speaker C

Yeah, but before we go back to you and I discussing some of the marketing lessons we've learned over the years. When you did your then now later, what are some things that you reflected on for the last 10 years that you did that you may would have done differently from a marketing aspect or business aspect?

16:08

Speaker B

I'll give you one from the personal aspect. First there was a lunch we were having. It was your now wife. Myself, you know, there was a gal with me.

16:27

Speaker C

Should have married her more like 4pm, 5pm in Arizona.

16:36

Speaker B

Yes, yes. And then Yaniv was there too. So at least one of my personal lessons should have just married her.

16:40

Speaker C

Right.

16:45

Speaker B

For me, that's one, I think, lessons wise also. I mean, obviously I learned to focus a lot better. Right. I think that that's a big one. I think had. Had. You know, actually I'll just leave it on me. Had I stayed focused, I think, you know, things would be different. I'm still happy with the outcome in terms of, you know, what I've learned over time. And I think it's really th those two things that stuck out to me. And then also, like I will say I had a lot of pictures of the office that we got back then. Having people in person, it's very difficult to beat that. Especially with some of the topics that we'll talk about today with AI and all that. We did have a fun discussion. So that's the then. But Neil, I'll throw you something that maybe we could come back to sayed brought up. We had a debate point around this on one universal basic income is going to happen for the majority of the population. How far do you think that is away, Neil?

16:46

Speaker C

Extremely far, because we can't afford it. We have issues getting budget approval for anything right now.

17:43

Speaker B

Pick, pick, pick. Like a range like 3 to 5 years, 5 to 10, 15 plus, 20 plus. What do you think it is?

17:49

Speaker C

I don't think it's going to happen.

17:55

Speaker B

Okay. Zero percent chance.

17:56

Speaker C

I don't know for certain but if I had to pick a number, I would say it's not going to happen at all.

18:00

Speaker B

Okay. It's really interesting because everyone across the board had different answers. And then obviously some people are way more opinionated than other people, so they'll like, put their opinion down way. But it's interesting. Like, I can see that answer coming from you and, you know, we'll see what happens overall. But even when I put a poll up on Twitter yesterday, it's like all over the place. Like, nobody really knows. My guess is five to 10 years. Syed says 15, which is actually pretty fast still. And then everyone else was actually. Some people were actually more aggressive than I was. Like three to five years. I don't know about that. Yeah, yeah. Yaniv was actually three to five years, so.

18:04

Speaker C

Oh, wow. Yeah. I look at AI as more of the change we had from things like agriculture, manufacturing, and humans in general. Yes, a lot of them lost jobs, but then we adapted and there was new jobs that were created. I look at AI as the same thing in which. And I'm a big believer in Peter Thiel's camp. And Thiel talks about how a lot of people talk about AI and all this stuff it's going to do. And then you got the dooms people that talk about how it's not going to affect anything. He's somewhere in the middle. I'm with him. I'm not saying he's right or wrong. I love his viewpoint because he is an investor in a lot of these AI companies. So for him, he actually makes more money if it succeeds. But for him to state that a lot of it's overblown from a job perspective. And I do believe it. Like when Heineken says we cut off 9000 employees because of AI. I'm not saying AI can't impact employees. I doubt Heineken actually cut 9000 employees because of AI. From a marketing perspective, that's a great narrative to pitch to the market. If you pitch the narrative of, hey, we had all these employees, we weren't able to perform and we weren't doing well, so we had to terminate them, that's probably going to make your stock tank because people are like, you're not doing as well. Using the AI narrative is much more advantageous. And I remember CNBC was at a conference, or there was a big AI conference or a tech conference. Cnbc, Bloomberg was all there. And they're interviewing a lot of these founders, both the Perplexity founder and the Anthropic founder, and both of them said most of these job losses have nothing to do with AI. Everyone's just using AI as a scapegoat. That doesn't mean AI won't impact jobs in the future. But as of now, when people are like, yeah, we're at Heineken, we're in manufacturing, and, you know, we have all these people in the back office, these big organizations move really, really slow. I don't know if you've seen any organizations the size of Microsoft or Heineken or Coca Cola move extremely fast like a startup. Eric, I don't know if you have. I haven't.

18:39

Speaker B

Yeah, I'll take that as he hasn't either. Yeah.

20:54

Speaker C

So I doubt that they adapted that fast and they were able to eliminate 9,000 jobs. But. So I just believe that universal basic income is probably not going to happen one, because we can't afford it as the United States. And I'm assuming when Eric asked this question to Pearset, I'm assuming you guys mean mainly United States because some other countries already have universal basic income.

20:57

Speaker B

I think everyone means the United States. Yeah.

21:20

Speaker C

Yeah. And I think the United States, being more capitalistic, is probably not gonna do it. But I could be really, really wrong here.

21:22

Speaker B

So I'll give you my take on it. So, wait, did you finish it?

21:30

Speaker C

Yeah, go for it.

21:34

Speaker B

Okay. So my take on it is, I think in the long run, we're going to be okay, I think.

21:35

Speaker A

But

21:41

Speaker B

when you look at the industrialization or when you look at when we move from kind of most people being farmers to most people becoming factory workers, that change took about 30 years. And there was definitely job displacement time. I don't think it's going to take 30 years this time. But to your point, people are slow. I think these things happen. I mean, there's going to be job displacement. Maybe that job displacement happens for a couple of years or so, then I think we even out. But during that time, maybe, you know, people realize maybe there does need to be UBI because there's going to be so much job displacement. Right. And the reason why I'm saying this, too is because we kind of went around the room and nobody's actively hiring right now. We'll just put it that way.

21:44

Speaker A

Right.

22:21

Speaker B

If anything, some people are looking to cut. And I think that that's kind of what we're seeing across the board right now, and even with, like, other friends that I talk to, too. So that's why I think it's five to 10 years. Because to me, this is. This is bigger than anything I've ever seen. Like the Internet was already pretty big. I think this is bigger than the Internet. And like even the things people were showing, like some people, like everyone's at different levels on the AI side over here in terms of the shares. But I think that's kind of where like my take is, yes, there's going to be some short term job displacement. And then I do think UBI is going to happen too. Because why? Because America, I don't think the money printer ever turns off. And so, you know, and I do think this is going into a little bit of politics, but I do think that, because we were talking about worldviews and I'll just give you one of mine, I do think we're going to see like the rise of socialism, like really, really push in the next couple of years. So I think. And what do people want in that situation? People want ubi, Right. And so the government, you want, you want people to run on a ticket where it's like, oh yeah, we're going to give UBI to everyone. Right. That's a president that can win to appease the majority of people.

22:21

Speaker C

So I agree the majority of people would probably vote for Universal Basic Income. I think the majority of the US would be very happy with that. Even though there'd be drastic consequences for us to just print that much cash.

23:29

Speaker B

Yeah. And Neil, one more thing. I think like this stuff, like, okay, let's say this costs like what if you were to buy it retail, maybe like five bucks or something like that at a hotel?

23:42

Speaker C

Icelandic water, One can. Or are you talking about a whole case? Just one can, A dollar, two dollars.

23:51

Speaker B

Okay. So I think because of AI and robotics and everything, I think that's going to bring downward pressure on pricing. And so maybe the price itself doesn't come down. But your, if you're making 35 grand a year, it goes a lot further because you can, you can do more with that money. That's, that's my point.

23:56

Speaker C

Yeah, I definitely agree with you. I think the Icelandic water example is maybe not the best example because companies like that, with manufacturing, a lot of it is pretty automated. I do see AI helping in the back office. But with a lot of those companies, their real cost is just manufacturing. And most of that stuff is already using robotics and automated and it's pretty cheap. But if you take that same example, what Eric's talking about, and you implement it with things like building SaaS products, right. Which are very labor intensive and the people that you're paying for engineers, I don't know what engineers go for, Eric, these days, but hundreds and thousands of dollars sometimes, you know, 2, 300 for really amazing people. It's very rare that you're hiring good engineers for 50 grand. I'm assuming you agree with that statement. He's nodding his head. You know, you give them cloud code and cursor and let's say improves their productivity by double, triple.

24:14

Speaker A

Right.

25:11

Speaker C

It's now way cheaper for you to end up making these SaaS products, which then makes it easier for you to give it away for cheaper or even freemium or even free. And that starts pushing a lot of downward pressure and just makes the whole market more competitive.

25:11

Speaker B

And we will see you.

25:28

Speaker C

We'll see you next week.

25:29

Speaker A

Goodbye.

25:30