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Ryan Levesque

Ryan Levesque

Author

Oct 7, 2026

4:55
[chuckles] Tell us about that.
4:56
[laughs] Yeah.
4:57
Um, you know, I think there are ti- If I look at my life, there are times in my life where most of the people around me said, "What are you doing? You're completely crazy." And, uh, I think the first few times it really shook me, like when I was a younger person.
5:14
I'm, I'm, I'm middle-aged now, but when I was a younger person it w- really shook me.
5:18
Um, like for example, when I was in college, I was studying neuroscience.
5:21
I was going to me- go to medical school.
5:23
I was gonna become a, a neurosurgeon.

31 MINS LATER

36:51
[laughs]
6:22
Okay.
6:22
So as entrepreneurs, we get less reach than we used to have on platforms like Instagram.
6:28
Um, as, uh, human users, we can't tell whether the content we're experiencing is AI generated, if it is by a real human, and we increasingly get served what I would describe as, uh, the, the, the, the internet of TV, uh, which is just all forms of internet has become short-form video across every platform.
6:48
Um, and that is a sort of la- last ditch, late stage attempt at these platforms keeping users addicted to the platform.
6:59
Zombified, just scrolling endlessly, and becoming a one-way form of consumption instead of what the promise of social media was when it first started, which was an interactive medium.
7:09
So I believe we're seeing the start of that, and there's data and signs to suggest that we are already on the way.
9:58
Yes.
9:58
And what's our business here today? Um, our business here today is, um, is one where we, um, offer services, marketing services to different businesses.
23:56
Yeah.
23:57
And so I, I recognized that I was in this window of opportunity, and I wanted to make the leap anyway.
24:03
Um, and I kinda had this moment where it was like, if I had sold the company, what would I have done with the money? And it's I would have, you know, moved my family to live a life immersed in nature and start a farm together.
24:16
And I kind of had this sort of second thought, which was, "What the heck is stopping me from doing that now?" Mm.
24:23
And the answer was nothing.
24:25
Now, on the surface, yes, there's all sorts of things.
24:27
We had schools and doctors, and I'm leading a company, and all these things.

19 MINS LATER

43:04
Yeah.
22:56
Yeah.
22:57
and so i had been building a company that was in hyper growth mode and i'd really spent about a decade of my life on this decade-long sprint and i built a seven-time inc 5000 fastest growing company generated well over a hundred million dollars in total revenue over that time And I woke up one day story that I share in the book and had a conversation with my business partner and said, I, I think we should sell the company.
23:25
Let's sell the company.
23:26
I'm, I'm, I'm, I'm feeling burnt out.
23:28
Like I want to, I want to get out.
23:30
And he was in agreement.
23:31
And so we work with the broker, got an offer for the company and, They changed the terms at the 11th hour.

22 MINS LATER

45:58
So can you talk a little bit about what your current business model is just so folks can get some inspiration about what a really viable, successful business could look like that is not based on more, more, more, more, more, more, more, more, more.
10:26
And I kind of
10:26
had to have this moment of, all right, this is not how the story was supposed to end.
10:30
And it led me to kind of pull this thread that I just couldn't let go of, which is the fact that, look, I'd spent my entire life as a technologist building companies, living in technology, living in front of a screen.
10:42
Was I insane to be starving for something different? Was I alone in this desire, in this quest, or was there something bigger showing up in the world? And what it led me is to continue pulling this on this thread.
10:53
And I read books on philosophy and futurism.
10:55
I studied behavioral economics and I studied history and found that in every major technological shift, like we're experiencing right now with the advent of AI, There has been a counter movement that's shown up in the world in response to that shift.
11:11
And what it means is that there's a craving that exists in the world right now.
15:51
We
11:37
Everyone's heard these stories, right? But when it comes to what is my voice, what am I the expert to talk about, how do you recommend people approach that question or, like, yeah.
11:49
You know, so I think it's, like, if we go back 10 years ago, even a, even pre-AI, people used to pay for information.
11:58
People no longer pay for information.
11:59
What people will pay for is insight.
12:03
Perspective.
12:03
And I'll give you a very real example.
12:05
So, um, I have a client who is an attorney, a lawyer, and we were having this conversation about where to shift the focus of the business.

7 MINS LATER

19:10
Please, yeah.
12:26
What did it feel like to send that confession emailed to your list?
12:33
It was not easy.
12:36
Because I felt like in some ways, even though this is standard practice in the industry, you have a team of writers.
12:41
If you're the CEO of your company, it's not uncommon that you've got a team of writers that are writing content in your name.
12:46
They're ghostwriting that content and they're signing that content with your name.
12:51
And for me, it became this sort of this death by a thousand paper cuts, where at first I was reviewing every email that went out by my name.
12:59
And then, of course, there's a time where things get a little too busy and you're like, it's probably fine.
15:49
What's the mechanism? Like, you know, real's a word that everybody banters around, but like, what's the mechanism? You know, is it trust? Is it scarcity? Is it something else?
20:30
You, that, you must find that fascinating.
20:32
Well, I'll, I'll, um, I'll say a few things to that.
20:35
So, um, yes, there's a tremendous amount of, uh, data that we have, uh, around the connection between oxytocin and storytelling and the connection that it actually creates between us, the bond that it creates between us, the, the writer and the reader or the creator and the viewer.
20:50
Um, but I'll speak just from personal experience, 'cause I'm not, you know, uh, preaching from the mountaintop as the, you know, the person who made no mistakes.
20:56
I, I made all the mistakes in the book.
20:58
Um, and so two years ago, I actually sat down, and I, I wrote an email that I titled The Embarrassing Confession.
21:04
Um, and in this email to my audience, I basically said, um, "I have an embarrassing confession to make, and it's, um, it's this.

24 MINS LATER

45:22
Yeah.
18:22
Did you make a good stake from that or was that a minority stake?
18:31
And so a few years later, I decided to write a book.
18:37
The book is called Ask.
18:39
And it really revealed sort of the methodology that I had developed and that I was implementing in all these different markets.
18:45
And surprisingly, the book went on to become the number one bestselling book in the country the week it launched.
18:52
Not in a category, not in like a random subcategory, the bestselling book in the country.
18:57
It just took off.
23:45
What was that conversation like when you said no? What words did you use? And then how did they react?
6:26
You are such an astute observer of the moment that we're in and when i read your analysis in your newsletter i'm just like that is right and nobody else is saying that so could you just kind of give us an overview of this moment and why it's unique and sort of what are the dangers and the opportunities
6:44
i think the narrative of the day is that there's one force that's radically transforming the world right now and that is ai and ai is touching every corner of business it's touching every corner of our lives But the reality is it isn't just one force that is transforming the world that we live in.
7:00
There's three forces that I believe are colliding all at once to create a singular moment in history.
7:05
AI is one of them.
7:06
The first is what I describe as an economic reckoning.
7:10
And so if you study the work of Ray Dalio, and he's not the inventor of this idea, he's the retailer of this idea, the world historically has operated in economic cycles, that empires rise, empires fall.
7:21
And this has been true for thousands of years.

41 MINS LATER

48:01
Oh my gosh.
133:04
Okay, so obviously I have to know, what are the seven factors?
133:08
So when it comes to choosing the right market and starting the right business, there are seven factors.
133:13
And I'll talk about a few of them right now.
133:14
So one of the things that we discovered is that every single one of the most successful markets have what we call the five market must haves.
133:22
These are five factors that if you want to be successful, you want to make sure your market has.
133:26
I'll go through them.
133:28
The first is what we call an evergreen market.

15 MINS LATER

148:44
Do you think everyone should do this? How is it broken down for you?
5:31
Right.
5:32
That is a better indicator of what you'll pay for your next backpack than the answer to the first question, what would you pay? Because you're actually asking people to access different parts of their brain.
5:43
A part of their brain where they're speculating into the future versus a part of their brain where they're looking at past behavior.
5:49
And if you have this conversation with someone in person, you actually see this.
5:51
They have tells.
5:52
You can see how their eyes move, how they look up and to the left, how they look up and to the right when you're asking these questions.
6:00
Most of the time, we don't have the luxury of asking it in person.
6:59
question,
0:35
Why do we do what we do? And why do we buy what we buy? Or why, if you're a seller, why do you sell? How do you get people to buy or to stay and serve other individuals? Or how do you make changes with your kids? Where do we start with this?
0:49
You know, I think it's first and foremost to start with how the brain responds to change.
0:54
Now the brain, whenever it's faced with any sort of change in life, perceives that change as a threat.
1:01
Now what's interesting is the change can be negative, it can be also positive.
1:05
And the brain's job is to keep us safe.
1:07
And it wants to preserve the state that we're in.
1:10
And so that's why whenever we're presented with an opportunity to make some sort of change in our life, We oftentimes, it elicits the fight or flight response in the limbic system, in the amygdala, in our brain.
3:13
Okay, you have to say that one more time for people listening.
19:04
Any others come to mind, Ryan? There's like
19:08
a group of episodes that come to mind for me.
19:11
And that would be the ones that we did at international conventions, including the one in Mashantucket that we talked about where we first met.
19:23
We haven't done that together.
19:25
Even when I was still doing the podcast with you, it had been a while since we'd done one.
19:29
But those were always so fun.
19:30
We'd go to the convention, we'd set up a table and be interviewing.

9 MINS LATER

28:11
It seems to work most of the time.

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