307 Michael Guimarin

Jeffrey Feldberg: [00:00:00] Welcome to the Deep Wealth Podcast where you learn how to extract your business and personal Deep Wealth. 

I'm your host Jeffrey Feldberg. 

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Michael Gimarin has an eclectic career at the intersection of technology and cognition, from web scale engineering to enterprise sales to startup angel investing. One of Michael's passions is academic work around how to curate your information environment for better outcomes.

Welcome to the Deep Wealth Podcast. Well, you heard it in the official introduction. We have a fellow entrepreneur in the house, but not just any entrepreneur, angel investor, [00:02:00] thought leader, someone who's out there with AI and really making a difference. But I'm going to stop it right there. Michael, welcome to the Deep Wealth Podcast.

An absolute pleasure to have you with us. And Michael, there's always a story behind the story. What's your story, Michael? What got you from where you were to where you are today?

Michael Guimarin: Hey, Jeffrey. Thank you for that intro. That's great. I like that. The story behind the story. I think since I was really little, I really liked learning. I had an insatiable curiosity. And then once I had that curiosity, I loved explaining what I had learned to other people. And so I've set up my life as like I like to solve problems.

And if I can get enthusiastic and excited about a problem, Then I want to solve it. And so it started in school. I learned computers by myself, taught programmer. So then I went to school and learned psychology because I wanted to learn about the intersection of technology and people. And then my first job was in engineering and it was very difficult and it was there were a lot of problems with, which hadn't yet been solved.

And then [00:03:00] my second job was more like engineering slash dealing with people. And then now I've worked more on the people side for the last, five, eight years. still with that same theme, right? The intersection of technology and people and the, problems that emerge there and do we best solve them?

So that's the story behind the story. And then there's a bunch of examples from my career that I can give.

Jeffrey Feldberg: And so Michael, if we take a step back for just a moment, talk about a perfect storm. So you have this insatiable curiosity. And from there, you took that, you put that into programming and then psychology and then engineering. I mean, Wow, what a mix. Coming through that and looking back now, how did that change how you perceive the world, how you process things, what you don't do?

Michael Guimarin: it's very interesting because I think everyone at 16, I felt like I had figured everything out and knew everything. And there was this very strange Experience that I've had, which many people have also told me is very common which is the more questions, when you seek to answer a question you sometimes you [00:04:00] get the answer but every time you seek to answer a question, you end up with more questions than when you started.

And so if you do that for like a decade or two decades. Where I'm at, then all of a sudden, you have only questions and very few answers. And so, even though I would say I'm vastly more experienced and understanding than I was at 16, I feel like I know nothing, whereas back then, I felt like I knew everything.

And so that, excitement of continuing to uncover more questions has been, a huge driving force in my career. And I think. It's intimidating for a lot of people. They like to stick in one area and become like a master of that area. And what I've learned is it's the intersection of different areas where there's a lot of frontier and open space and things that have never been done.

And then, of course, More questions. So that sort of loop of curiosity gets fed and gets faster and gets bigger. And again, I feel like I don't know anything now and [00:05:00] I know a lot. So it's it's bizarre.

Jeffrey Feldberg: Michael, as you're going through that, it reminds me, and hopefully I won't botch it too much, Albert Einstein said something along the lines that the more I learn, the more I know, the more I realize how much I don't really know. And it really takes someone who can be humble and open. To be able to say that.

And so when you're looking at this, when you're looking at your journey and Michael, you're into all kinds of interesting things and we'll get there, but looking back today, and this may change tomorrow. It may change a year from now, 10 years from now. Is there a defining moment that really made the difference for you?

Michael Guimarin: When I was freshman in high school, my grandmother had come to live with us and she had been in the world. For a long life, and she related to me when she moved here, the story of my family and all the people that had come before, great grandparents, great great grandparents, all the different sort of archetypes, her father, her mother, and at the end of [00:06:00] this relation, she turns to me and she goes, so what exactly is it that you're going to do to add to this podcast?

You know, I wouldn't say legacy because there was a language gap. English was like her seventh or eighth language, but it was functionally like, what are you going to do to add to this legacy? And so from a very young age, 15, 16, I was like, okay, I want to be very deliberate about what I am doing with a very clear value system that I'm employing so that I, as I move through all of my life, It's a continuous, singular picture.

And so the way that I describe it to folks is I view my life as a big art project. And I am both the only artist and the only viewer of that art project. So a lot of the things that I'll do, you know, like some people will do things because they want a great story. I do things because I think it will make an interesting memory for myself.

And I relate that to learning, and so there's just a lot of [00:07:00] esoteric curiosity that then gets, driven towards, because for me, it's like, well, this is just me filling out a corner of my art project. That is my life. And so that's, been the sort of simple to explain theme through this whole time.

And it happened because of that, challenge from my grandmother, right? What are you going to do to add to this legacy?

Jeffrey Feldberg: Wow. What a grandmother, what a terrific question, but seven, eight languages. I'd be terrific if I had two, maybe three, but we're talking so much more than that. And it sounds like that question, and now you're viewing your life as an art project, but just for yourself, it's really you up against you.

And can I be better today than it was yesterday? And I know as of late, you've been doing something really interesting, particularly on the technology side. On the AI side, do you want to share with our community what's been going on with that and what you're doing?

Michael Guimarin: Yeah, so I've been an angel investor since 2017. And so I've been investing in companies, some successful, some not. And The thing that I have continued to learn is that if you really want to understand something, you need to [00:08:00] be at the ground floor of it and you need to be in the weeds. And so about a year and a half ago, a friend of mine came to me and said, I think that AI is going to put me out of business.

And I'm really curious how to put myself out of business using AI first, and is this something that you could help me with help me build this product, like I help people sometimes build apps, and so I said, actually, it's not just putting you out of business, it's really changing the entire relationship with the product.

of information, management, and sort of knowledge work. And so I'd really like to start a business with you, actually, and we want to solve this problem. And we just went and started tackling it. And I've learned so much, all bootstrapped but I've learned so much. By building technology and selling it in AI.

So our app is called the WordOut app and it is a workflow management software. So we're using AI to tackle the entire marketers workflow. So instead of, you might think of AI today as like you ask it a question and it writes you an [00:09:00] essay. Our understanding of it is more like. There's a workflow that a marketer needs to go through in order to drive sales for her business.

What is that workflow? And where can we use AI and technology to accelerate that workflow? And then after we do that, how does that workflow fundamentally change? And to explore that from a first principles perspective is really giving me a lot of depth of insight into, what would happen. And just to give you guys a very concrete example that is not so much a ha, I was right situation so much as.

You need to be very careful in technology. A year ago, I went to a conference that was put on by Jasper AI, which is a generative AI writing company that had received over a hundred million dollars in funding. And I was sitting in the back of the conference with the employees of That company, who again, had raised 100 million, and here it was a 2, 000 person conference in [00:10:00] San Francisco, and they were talking about it, and it was quite successful, and it was very interesting, and one of the finance guys and the head of marketing, they turned to me as an audience member, and they said like, Wow, isn't this so amazing?

Next year it could be like 20, 000 people and everyone started ricocheting around 20, 000 people and I said, yeah, probably more likely 20 people next year than 20, 000 and they looked at me like I was on the moon and there is no conference. For them this year, and they literally spent probably 10 million of the 100 million they raised running that conference.

It was a beautiful conference, supposed to be the next Dreamforce, and a year later, it didn't exist. And that's how insanely fast technology disrupts and accelerates an industry. That even the people who are at the bow wave of that can get completely wiped out. And that company is totally pivoted. And, all of the questions that I was asking at that conference, they were very [00:11:00] from our thesis perspective, very prophetic because a lot of them, there weren't answers.

I was asking the customers for that company and that company itself, what are you doing about X, Y, or Z? Oh no, that's not going to be a problem. And then, here we are, and they're not even hosting a conference for 20 people. And so I think that this is why you have to be very careful about VCs and why I I think we're seeing something like 70 percent reduction in VC funding for startups year over year I believe that to be true or at least directionally accurate by an order of magnitude, simply because I it, the level of disruption is so crazy.

Jeffrey Feldberg: And so, Michael, that's interesting because as you're talking about that, it's a terrific segue as an angel investor, as an entrepreneur, as really someone who's looking into the future, as we all do, but in different ways. So what's your philosophy as an angel investor? So here you are at this conference.

Ten million plus dollars, give or take, went into this. Everyone is talking about next year, how great things are going to be. And you're the contrarian saying, I don't think so. You may not even be here. And a year fast [00:12:00] forward is exactly what you said. So what was going on in your mind? What was the mental chatter?

What was your purview that gave you some hints of that?

Michael Guimarin: Yeah, thank you, that's a great question. What I have observed, so I was in Silicon Valley in the 90s what I have observed in other technology disruptions is that when the cost of a particular activity that was previously a bottleneck goes to zero, which is what happens when software digitizes something, the demand for that Activity seems to go exponential, but actually it goes in an S curve, and most humans have a very difficult time even moving from a linear extrapolation to an exponential extrapolation, and even fewer understand the nature of S curves.

And so what happens is not we get infinite music listening because anyone can use Napster to download, more music than they could listen to in a lifetime. What happens is that the value accrues in a different [00:13:00] bottleneck in the system. And so it was clear to me that even though the bottleneck in marketing and, marketing teams had been generating content.

That once that was no longer the bottleneck, then the entire way that the team would be organized and the activity that the marketing team would do in order to drive value for the business would change. And it would actually shift towards an entirely different set of bottlenecks. And that's ultimately where the value comes.

Because anytime that you take a process and you digitize it, the value of that process goes to zero. And I think that is a very difficult concept for people, especially those who are Gen X and older, because they're used to a technology or tool reducing the cost of a product. problem and therefore seeing demand increase to offset supply even greater than linear, but they don't really grok that consumption doesn't go to infinity.

And so they're not able to see beyond that. And that was exactly what happened there is the bottleneck went from content [00:14:00] generation to content curation which really put struggle on our thesis, which was the marketing workflow, not on, if I can produce. A unique content generated asset for every single customer, then of course they're going to buy, because that's not actually the signal that they were buying in the first place.

Turns out they were buying competence, and you're just evaluating the competence of the solution provider's ability to create content, not actually the content of that content, but really the context of that content. And I think people missed that, and we saw half a billion dollars evaporated in the market in six months.

Jeffrey Feldberg: And really, as you think about that, Michael, for most people, we hear half a billion dollars. It's difficult to comprehend and really compute and a half billion dollars, it's such a gigantic number. But let me ask you this, because I know in our nine step roadmap, step number one, the big picture, we're looking for inflection points, what some people call blind spots.

One of the questions that we're asking, hey, where is there a change in the [00:15:00] marketplace that if I don't do anything about this, one of two things is going to happen. It'll put me out of business. Or if I can hop on this quick enough, if I can take the right actions at the right time, I'll be the one to put myself out of business.

Into a bigger business. And this is exactly what you're doing. So for our listeners, what would be a strategy or a takeaway with really your outlook as an angel investor, as an entrepreneur, someone who's been in Silicon Valley, and you've had that experience now for quite some time. What's something that they could be doing or questions or actions they could be taking to prevent exactly the kind of situation that you just described from that conference of 2000 people, forget 20, 000 people, not even 20 people the following year.

Michael Guimarin: Yeah. I think it's very difficult. First of all it's exceedingly difficult because it gets to sort of the core of who we are as people and our identity. And so you have to de center your identity from your work. And it's very difficult for people to do that because their work comes to define who they are, especially here in the West and the United States.

And then you [00:16:00] have to consider what Upton Sinclair said, which was, it's hard to get a man to understand something when his salary depends on his not understanding it. And what I think that this means in this instance is that. When you evaluate your business from first principles and I hate, maybe you say that's overused, but I really like it as a mental model with this new technology, it could be that your business no longer exists.

So, like, I'll give you a real world example of this. Right now, there are a lot of small medium sized businesses that are operator owned. That's it in the boomer generation. And so there's all these articles about how these businesses are going to transfer to the millennials. And this is going to be the greatest transfer of wealth ever.

And if you could just buy 1 of these businesses, it's going to be great. And, there's all these mid level, private equity, small level, private equity opportunities to do these businesses. And 99 percent of those businesses are going to get wiped out. And the reason why they're going to get wiped out is the same [00:17:00] reason why they exist today, which is they never deployed technology.

So today, a business is not just one guy. It's also the entire ecosystem of all his providers. And so it's not the case that you're going to take a old business that never used digital software, come in, add digital software to it, and then just Increase the business's output like you would in a traditional turnaround model with private equity.

And that's because the business exists in an ecosystem of other boomer businesses that also operate on a paper-based system. And so as soon as one business transfers over, so do all the others, and so then the entire ecosystem changes because they are now all en enabled by software. And so you actually get.

Entirely different dynamics. And so I see all these people talking in the market about, oh, we're going to buy these private equity businesses from our parents and look at our parents. Ha. They don't know what they're doing. their entire businesses like Bob and Tim, who are also the same [00:18:00] age, who are their supplier or customers.

Not knowing that those businesses as an archetype will also get softwareized, digitized. And so the entire value chain in that model changes fundamentally to the point where most of those businesses won't exist. And then, of course, you get on the other side, which is there's still going to be a guy that owns a business that rents porta potties at a 50 percent gross margin.

So you do have to think of it like, okay, what is actually the customer problem that's being solved, not the business that's currently solving that customer problem. So I think maybe that's the takeaway.

Jeffrey Feldberg: And speaking of takeaways, and it's interesting, hey, yeah, it sounds great on paper, but Likely not as easy as you think, and hey, a heads up, you can't keep on doing what you're doing, and even if you try to transfer it and go along that path, there's so many moving parts that it's not going to be as easy as you think.

Again, very contrarian. I want to reach you part of a post that you put on X, formerly Twitter, And perhaps he can walk us through that and talk about that because it's right in the middle of [00:19:00] AI. It's with you really as an investor that's involved in this. And the quote is somewhat controversial. And you say, when I looked at education across the country as part of the synthesis school, it's clear that the mainstream education system, both public and private, was in complete collapse.

And I'm fast forwarding a little bit. You go on to say, rich people are doing this. Everyone is doing this. It's millions of students, not just religious fundamentalists like Gen X and millennial homeschoolers, these students with engaged parents used to keep the classroom on some level of normalcy competence.

And then you go on with your thesis or your insights. So what's going on with this school, AI, online homeschooling is a whole, I don't know if I want to call it a trend, but it's really a. New direction that's taking place. What happened with this and where's it going, Michael?

Michael Guimarin: Yeah, I think it's very interesting. We've had data since Project Follow Through in the 60s. That the school system provides no benefit whatsoever above baseline but for [00:20:00] reasons in our society, we never really wanted to evaluate that data, so like, the conclusion of Project Follow Through is it doesn't matter what educational system you use, the children will learn just the same, unless you use direct instruction, which is a call and response system, in which case, children will learn like three to five times faster and better.

Than any other system but for reasons of, like teacher retention, we never implemented direct instruction in any school system. And with the pandemic and all of these competent women who previously were on the PTA or whatever, seeing how incompetently their children were being micromanaged from afar, like on the Laptops basically decided hey, I can do this better myself, and we're all stuck at home anyway and then they just didn't go back, and the real problem for the education system as it exists today is that these engaged parents were the ones who were actually driving the outcomes, and Now that they're not in the education system, you're just watching the outcomes get worse and worse in all of these [00:21:00] systems.

And I've seen it. used to send my kids to private school. I went to private school. In fact, I sent my kids to the same private school I went to where I met my wife. And like watching the kids in real time fall behind our child who's homeschool because they're not. Doing anything real. It's really crazy.

It's like really the most insane thing I've ever seen. And like, as a millennial, so I was born in 87. I think the statistic is there was something on the order of 65 to 85, 000 homeschooled kids in 1987. And today in 2024, it's something on the order of like four and a half million. And that's not due to population growth, you could even say let's say the population of the US doubled, which didn't.

You would only see a hundred and, you'd see 200, 000 homeschooled kids, and instead we see four million. And my experience as a wealthier person, as an investor in San Francisco and in the Bay Area, is that very competent people pull their kids out of school. And not just the public schools, but also the private schools, and they're building their own school systems, and they're using the [00:22:00] internet to swap curricula, and they're finding out that it requires 10 to 20 minutes a day of instruction to beat The public school systems, and then they're giving their kids, you know, up to two hours a day of instruction, so their kids are graduating at 14 years old with a GED, and they're ready to go to community college.

it's kind of like the most amazing thing ever. So you have this, again, internet driven bifurcation where the small group of people let's say the engaged moms was 5 percent of the population, their returns for their children are just skyrocketing with the internet. And the other 95 percent they're getting pushed to the bottom.

It's kind of like this observation that we have more obese people than ever in the United States, but we also have more fit people than ever. And that's just something that internet drives is it pushes people towards the extremes. And so like one of the questions we actually have in the community here is what are we going to do, not that our kids are going to be so much more educated than all the other kids, it's what are we going to do with the society of all these people that [00:23:00] can't read, can't do math, have no critical thinking skills.

You can't run a society that way, so it's it's an interesting conversation.

Jeffrey Feldberg: It's changing societal values and certainly a lot at stake. And let me ask you this. So with homeschooling, picking up momentum, I'd imagine as we look forward to this, to the future, AI and technology, and really the dream of educators has always been, I'm going to get Michael or Jeffrey, their own tutor, who can adjust to their learning style, go at their speed, talk about what's interesting to them, but still have them achieve the learning outcomes that are desired.

Technology, AI, it's now within grasp, it's within reach. In fact, you can even say it's actually happening. So what's going on with that in that whole community and with AI technology, you as an investor, where do you see that going? What's happening there?

Michael Guimarin: Yeah, so I think it's a broader thesis, which is the digitization of The first three kinds of information, which is propositional, procedural, and perspectival [00:24:00] information it has changed the value from creation to curation. So we actually don't care so much about creation anymore. It's not valuable.

It's free. And so we're focused on curation. And so what you're seeing is It's not the case that humans specific, like AI is going to shift the entire distribution, but the moms that are curating what the AI gives their children, their kids are going to do even better. And so it's not the case that we're going to remove humans from the loop.

It's the case that You know, we are just gonna see AI accelerate the entire distribution and where the engaged moms are helping their children, they're gonna win. And in education in specific, there's this secular trend where women have decided at a high level that the education of their children is more important than their professional career.

And so, it's not stated anywhere, but it's functionally what's happening from an outcomes perspective. And so there is again, like this basically return to [00:25:00] the home or whatever you want to call it. And that is also, or like shifting their work from a full time nine to five schedule to a part time, small business.

Kind of thing, where they are spending the required couple hours a day with their kids with AI to make them even better. Now that, in terms of like, does the 10th percentile student learn how to read with AI, I would argue probably not because it's not so much you can give them an iPad and then, but they don't even sit in their classroom.

Right. They just spend all the time, chatting on their phones or whatever. So unless something fundamentally changes, like the educational outcomes for the vast majority of people who are not engaged in becoming educated, they'll just continue to get worse. Like the AI doesn't solve the problem of the kid wants to learn.

If the kid wants to learn, sure, you'll be really smart. You can already go online and get every single MIT lecture for free. So the cost of a really world class education to anyone with a smartphone is functionally zero at this point. And so the value of that [00:26:00] education now is not having access to these classes, it's which class should I take in which order and what are the set of problems that I need to overcome in order to gain the participatory knowledge, which is that fourth class of information to really be valuable to myself and to society.

Jeffrey Feldberg: And so, Michael, what you're saying is really interesting because correct me if I'm on base or off base with this, what I'm hearing you say. The better technology gets, the more sophisticated AI becomes and integrates into our lives. That's all fine and good, but the real difference, it comes down to the creation or the curation.

And so in your case, if it's a part time or stay at home mom with a child who's curating what that child's going to see or in the workplace, we're curating how we're going to leverage that AI into what we're doing and what we're looking at, because now it's become, as you're With so much information out there, it's available for free and we can access it.

There's more than we could read in a lifetime is what are you reading or what are you looking [00:27:00] at that's then going to go on to have you take that next step? So it's the curation, what I'm hearing you say, that's where the magic is happening. How am I doing with that?

Michael Guimarin: that's exactly right. And the simple example is, would you like a USB stick of every book ever written, which you can get, or would you like a USB stick of every book that Jeff Bezos ever read and the order that he read them in, which is more valuable? And most people would choose the latter you can carry around Wikipedia. I remember in 2000 or whatever, like people, nerds in my group would be like, Oh, that's so great. We have access to all this information, like all inequality and injustice in the world is going to disappear within a generation. And I was like, yeah, that's good. And we already see the thing that matters is the curation of it, right?

Like today you have a very limited number of people that are managers. Tomorrow, everyone will be a manager, and instead of managing employees, you're gonna manage AI agents. And so, again, the skill set that everyone needs to have is that curation skill set, not the creation skill set. So we don't care whether or not [00:28:00] you can write a great sales letter.

We're going to have the AI write the great sales letter. The question is, which sales letter should you actually push into the market? And it's not going to be the case because attention is a reserved resource, which I mean to say is it's finite. It's not going to be the case that you're going to push every single sales letter you could possibly write into the market and see which one sticks.

Because people are going to use AI on the other side to read what's in the market. So there's going to be an entire buffer between you and the customer in the marketing context. And again, I'm using that example because it's easier for people, but it's really in every context. And so you're actually going to have to exercise discernment in what you should put out into the world, which, again, the best influencers, which is a form of curation, already do.

And I want to say one other thing before we go. I know we still have some time, but I think this is a really important point, and I think a lot of older people miss this, and I think you should pay attention here, which is, they say something dumb in the 1960s, people were a [00:29:00] lot better off because if you asked an 11 year old, what do you want to do when you grow up?

And they say something like, I want to be an astronaut, or I want to be the president of a company, or I want to be the, president of the United States, or the CEO of a company, right? And then you, and then they're like, yeah, wasn't that amazing? We had this great thing. And then you ask kids today, what do you want to do?

And the 11 year old tells you, I want to be a YouTube star, an influencer. And then the incorrect conclusion that people draw is that the kids have gotten dumber. And actually, it's the adults that have gotten dumber, because in a limited information environment, the emergent structure that you get is a pyramid, like it has to be.

And so the top of that pyramid is the astronaut, right? Three astronauts go to the moon, there's 60, 000 engineers who put them there. The top of that pyramid is the CEO that has a 20, 000 person organization. The top of that government pyramid is the president who makes, the executive who makes all of these decisions.

That's an [00:30:00] information scarce environment. In an information abundant environment, we don't create pyramids. We create fabrics that look a lot more like a brain network, a neuronal network. And in that case, you actually want to be the most central node. You want to be the thing through which all decisions go through, which is a curator, which is to say an influencer.

And so when people observe oh, we're getting worse because the influencers, like they're actually revealing their ignorance because the kids already understand what the most valuable thing is. And the most valuable thing is not to be a president or a CEO or an astronaut, which is why the relative prestige of those positions and the quality of people seeking those positions has gone down.

The most valuable thing is actually going to be the curator and whatever information flow there is for somebody. So I think this is something to think on as we're looking at this transition.

Jeffrey Feldberg: Michael, as you're talking about curation, and by the way, I couldn't agree more with what you just shared. If you go to curation, let's take technology out of it [00:31:00] for just a moment. You remind me of a story, believe it or not, of Henry Ford. Back in the early 1900s, and back in the day, there was an editorial, I believe it was the Chicago Tribune, that said, basically, Henry Ford is not the smartest guy around, and Henry Ford went to sue the Chicago Tribune, and they brought all these lawyers of or armies of lawyers, and they're asking all these questions, when did this happen in history, when did that happen in history, And Ford is patiently listening.

And at one point he says, and it gets to your point of curation. It was just at a different time with different technology. He said, why would I want to fill my mind with such useless information on my desk? I have this box, I push a button and I can ask any number of people, whatever question I have, they're the subject matter expert, they'll bring me the information and then I decide how I want to use it.

And so if you take that concept and you fast forward today and it's with AI or the internet or technology and this curation. It hasn't changed. Perhaps we've gotten a little bit more sophisticated or access to more information. We don't need a room [00:32:00] full of people with a push button anymore to ask the question, but it's a whole leadership style of knowing who's going to be in your circle, what you're going to be asking, what you're doing, and specifically what you're not doing, that's going to help accelerate how you're going to get to where you want to get to.

And that really leads me to my next question for you. You've been again, in the startups, angel investor, in the entrepreneurial role. So when it comes to leadership. And I use the word leadership very specifically because leadership in my mind is very different than management or being a manager. What's your philosophy?

So as a leader, what principles are guiding you or how do you approach to leading yourself or the teams around you in terms of really helping everyone get to the end goal? What does that look like for you?

Michael Guimarin: I'm probably newer at this than most of the people that you are working are listening. I basically have only been doing this for about 10 years leading teams both, individual teams where I was a manager, and then a team of teams sort of approach. And the way that I think about it is that my [00:33:00] role as a leader is to figure out where it is that we're going to go and communicate that in the broadest possible way.

And then enable the team, you know, basically invert the pyramid, if you will, enable the team to go and achieve those. So, like, when I hold one on ones, the question that I always ask is, what bottlenecks can I remove so that you can be more effective? Is there a piece of software that you've come across that you think we should deploy for you to get more leverage, right?

The focus is always How can I help the people who are working with me, or under me, or whatever, the people that I'm leading to meet the individual goals that they've set, and I view myself as really good when nobody above me really understood what does he actually do? And I was like, oh, I sit on all my time, make sure that we're in alignment, we're aligned, and you know, there's accountability.

So I just focus on accountability and alignment. And making sure that people are enabled to achieve. And basically I always [00:34:00] tell everybody my greatest gift in life would be to enable you to such a degree that I have to fire you because you've grown out of our ability to provide an appropriate level of compensation for how good you are as an employee.

And people are a little bit weirded out by that initially, but then eventually they're like, I completely understand. I was like, yeah, we can only pay X amount of dollars for this problem to get solved. And now you're able to solve problems that are like, 10 times more gnarly. And so, like, here, let me write you a letter of reference for this area.

Jeffrey Feldberg: I absolutely Love that. You know, It reminds me of my own personal philosophy. Most people, when they came onto the team, likely not all the time, but likely they needed the company more than they needed or rather they needed the company more than the company needed them, but over time, like you're saying, they get better and it gets to the point where the company needs them more than they need the company.

And it's really the sign of a superb leader. And so let me ask you this, as you think about leadership and you think about where we are today. Really the work life harmony, and I [00:35:00] use harmony, not balance because I don't believe balance exists. I think it's a concept for Hollywood or a fiction book. How do you figure out for you, for your team, that work life harmony?

What does that look like? What are you doing?

Michael Guimarin: Well, I like startups. I like problems where we have a lot of leverage. And so I believe that when we are solving a problem, we'll get into a blitz scaling situation. And I tell people that you don't really get many opportunities in life to go into such a scale situation. You're going to get scar tissue and you're going to get burned out and trying to tell people in advance.

And you're going to learn something crazy, experience something that you haven't had. I've been really grateful that I've been able to maneuver myself into position two or three times in my career where we went through an experience like that and it's transformational. You really learn who people are.

When everything is breaking because it's scaling so fast, and you wake up in the middle of the night, and I know as an entrepreneur, I've had [00:36:00] this as well as a founder, you're, basically coughing up blood for, you know, as a metaphor, because you're just crushed by whatever it is, you know, in the morning, it's great, in the afternoon, it sucks.

It's just this insane, crazy rollercoaster of And my thing is basically you just gotta survive to the next day in these blitzscaling situations. And everybody talks about work life balance or, I know you're trying to get away from that word. But from a Harmony perspective, what I say is like, your goal is to be, like, an elite athlete where you want to only sprint for your race.

But then you're, like, always training and you're always preparing mentally for that race. But then when you get in that race, you're just in that race. That's what we do. And I remember at one of my companies, I did onboarding or interviews where I have done all the interviews. Actually, I've always done interviews for whatever reason.

And I always would tell people, especially if they came from a large company background, I said, Hey, You know, one of the things that I see, and it's true, it's not even something I made up, one of the things that you see with people from a big [00:37:00] organization is they don't understand what it's like to be in an organization where everything is broken and on fire and there's no structure and there's no help and no one's coming to help you.

And so I think the way that I approach Harmony to answer your question, and this is very circuitous, but It's basically to tell people in advance you're joining a total shit show. And the question is is this something that you're aware of? Everybody knows every company is super incompetent, but like startups that are doing well, it's like a clown car that falls down a gold mine.

And so if you can mentally prepare yourself for that, I think it limits the amount of permanent damage that you do to people. And I think where the challenge comes in is when you ask people to grind. On something like a death march, if you will, and there's no, success at the end of the rainbow that they're going for.

They don't even understand why they're doing what they're doing because they're being cynically exploited or whatever. And so I do get a lot of people like that as well, who say oh, I already did this, treadmill at my other work and I want to, [00:38:00] clock off at 5pm and I kindly tell them that maybe startups isn't for them and that's okay, 

Jeffrey Feldberg: sure, it's all about mindset and speaking of mindset, particularly in a startup, but even in an established business, we're not always going to win the day. Things happen. A so called quote unquote failure comes onto the scene. How are you personally dealing with that, Michael, and things don't go your way where it took your moonshot, didn't happen from the outside world.

It's a big failure. What's going through your mind? How are you dealing with that? A

Michael Guimarin: Yeah, I try to reframe it as what did I learn? So like, again, all the opportunities that I'm pursuing, there's a learning component of it, which is how I measure success. Success is also measured by sort of dollars in the bank, but I don't really spend them, so it's not itself a measure. I try to help people with that too what are we learning for this?

I think the other thing is, early in life, I did a lot of sports, and one of the things I think you learn in sports is how to lose and still keep going. And I did individual sports and team sports, and in both [00:39:00] cases, you lose, and like, how do you, you know, there's no team that wins every game and then wins the championship.

So if you want to win the championship, you're going to have to learn how to overcome losing, and I think it's the same in business. It's like I've lost many, many, many, many more times than I've won and those losses, however you want to account for them, but I always think of them like there's a learning opportunity.

Like in sales, for example you can do this thing where you can calculate the average year closing rate for how many cold calls you make and all that kind of thing. And then you can assign a value to every cold call that you have, even when it's a loss. You can say like, okay, I called that person, they said no, but a no is worth 50 to me.

So I need to make, another hundred calls before I get one yes. And that yes is worth, the sum of all those no's because it's a statistical thing.

Jeffrey Feldberg: little bit of a gamifying there. Absolutely love that. Other things that I've heard along those lines is okay. If pick a number here out of every 20 people that you speak to, one says, yes. Okay. That was my eighth so called failure or my eighth hang up or [00:40:00] my eighth. No, 12 more to go. And I'm there. So let me just get through the no's quicker and I'm going to get to the yes.

Michael Guimarin: Yeah. Like I've never met a business where you couldn't 10X revenue by 10X ing the number of inbound. You can always increase the amount of sales activity that you're doing to generate more revenue.

Jeffrey Feldberg: And whether it's through technology, Michael, or it's just how you're looking at things. So let's talk about 10X for just a moment. Lots of people talk about the 10X and the 10X could go really both ways. How do we 10X revenue or how do we take our cost of sale as an example and 10X it the other way? So if it's costing, I'm making up a number, 2, 600, let's 10X it.

So it's 260 when you're approaching those kinds of challenges. Again, what's your mindset or what are you bringing to the table for what the seemingly impossible is that it becomes I'm possible.

Michael Guimarin: Yeah, I think that really gets, so like on costing, your question is does this business have economies of scale, supply [00:41:00] side economies of scale, or demand side economies of scale? So, to make a 10x reduction in your costing. You're not going to rely on supply side economies of scale, right? So what I mean by that is, if you sell widgets and the input is aluminum, and aluminum costs 10 per unit in raw materials, you're not going to reduce it to a dollar by selling more widgets.

There's a limit to how much cost you can take out of something when you're subject to a supply side economies of scale. Whereas on demand side economies of scale, which would be something like that has a network effect the bigger the network that you create, the cheaper your cost is going to be.

So, for example, at Synthesis, a lot of the activities that we were engaged in were not linear, we're going to make Google ad purchases. It was basically, like, how do we make sure that kids are successful going through the program and then they're recruiting all their friends? Because I'm not paying for them to recruit all their friends.

They're doing it because There's some status value associated with them, right? Their parents buy the product, that's great, they pay for it, but I need the kids, [00:42:00] in that case, to tell their friends hey, if you do this product with me, it's like, we looked a lot at playing cards, right?

the value of Magic the Gathering or Yu Gi Oh or any of these card games increases with the number of players because you can just Pull out your card deck at lunchtime, at school, and then there's other people that are playing it. Well, the more people that have card decks in their backpack, the more valuable it is for you to have a certain card deck.

And so the question was, how do I enable our end user, in this case, the child, who's not the customer, right, the parents, the customer, how do I enable them to recruit their friends? And that's how we reduced our customer acquisition cost.

Jeffrey Feldberg: And speaking of synthesis, you've done something really remarkable there for the benefit of our listeners who haven't heard of this. They don't know what it's about. What's the quick bird's eye view of synthesis and what you brought to the table and where it is today.

Michael Guimarin: Synthesis is an amazing AI education technology company, and when I worked for the business, it was focused around their Teams product, which was how to help kids overcome and navigate uncertainty [00:43:00] as a group in the face of a learning game. And it was very fun for the children. They loved it.

There were some costing issues on the backend for enabling the games, and so there was a limit, actually, to our ability to service at some, level. But before we hit that limit, I grew the business. Extremely quickly. I don't know if the numbers are public, but like it's a ridiculous rate of growth and like more than doubling in a month kind of deal, like for sustained period of time.

So it was like a lot of growth very quickly changed the entire trajectory of the business. But the big thing there was to focus again on having the kids recruit their friends and now Synthesis, they have a Teams product, it's still going great, but their focus has shifted entirely to an AI, an individual AI tutor that helps kids 8 to 14 learn math and I think they're working on some other STEM subjects like maybe chemistry or physics next, but yeah, I have my seven year old daughter does it and she's, she's doing it.

[00:44:00] Very advanced in math. It's a good supplement for homeschool kids or for kids at school who are not challenged by the curriculum yeah, it's been, it's been pretty awesome.

Jeffrey Feldberg: Michael, what's interesting about the example that you shared is you took a look, let's just call it your ecosystem, the business ecosystem. Okay. We have the traditional customer in this case, it's the parent. We have the end user, which in this case, it's the student or the children. And if we're open about it, most people would say, well, you know, the children, sure they're the customer, but not much value.

Let me see other ways I can do it. But you approached it unconventionally, you said, okay, how can I have the kids talking to the kids to bring their friends? Word of mouth, as we all know, it's the best way to grow and get things out there. And again, let me go back to your thought process, whether that's as the psychologist or the engineer or the programmer.

How did you approach that you had that eureka moment? Hey, let me speak with the kids. Let me give them something to talk about. So they bring their friends and those friends bring their friends and we exponentially grow the business.

Michael Guimarin: Yeah, it's basically comes from evaluating every single channel the business [00:45:00] is currently selling into, right? So, we had You know, our direct email list. We had Google ads. We had Google search. We had Facebook ads. We had all of those businesses. And what you learn when you run all of those areas in your marketing team is it's important to be in all of those areas, but there's only ever going to be a linear growth rate.

If you really want that exponential or that S curve growth rate, you have to use word of mouth. It has to be because of organic and in a business that You really need to understand, so I had worked in sales previous to this, so I understood the concept of the person that the software is sold to is different from the person the software is used, because I've used this absolutely horrific piece of software called Salesforce which is great for managers and terrible for salespeople absolutely like the worst piece of software, and I could just go on and on about that, but it's I had that very visceral experience, and so I was like, okay, when we're looking at our [00:46:00] business, how can I not sell to parents, which would be like selling to executives.

How can I sell to the kids and what are the steps that we can do? So we tried all kinds of things. We did gear, we did direct mail, like they would get a box. So it's completely virtual product, but they'd get a box in the mail there was like an AR like token, like a POG, if you will, where you put your phone over it.

And there's like a little character that was in the game. And, we tried all kinds of stuff to try and get the kids. To refer their friends and

Jeffrey Feldberg: just goes back to looking at mindset, how things are different. How can I really extrapolate perhaps to the unexpected? Yes. Let me ask you this before we go into wrap up mode, is there a particular question I didn't ask or a topic we haven't discussed or a message you want to get out there to the community?

Something that you feel would be of value for them?

Michael Guimarin: I think the big secular change is from creation to curation. I think understanding who are the people that are curating in your business today and what does it look like for every [00:47:00] person to be that person in your business in the future? I think asking that question is.

Super critical. I think related to that is to think about the four P's of information, so I already described them. The first one is propositional, so that's information like, A squared plus B squared equals C squared. There's procedural information, which you could think of a recipe or like a book that helps you to put together the IKEA or the LEGO set.

And then there's perspectival, which is video of somebody putting together the LEGO set or doing the recipe. Those three kinds of information which exist in your business, they're free to digitize and to distribute. And so, as a result, the value of people who are only focused on those three kinds of information is going to go to zero.

And the value then shifts towards participatory information, which is actually the experience of putting the Legos together and making the dish on the recipe. And so you have to ask yourself okay, we're going to shift from creating information to curating information. And we're going to [00:48:00] focus all of our attention on what's scarce, and that's going to be participatory information.

And so how does my business look from first principles when I think about it that way? And to make it really clear. The three professional schools that we have, law school, medical school, and business school, are entirely about communicating propositional and procedural information, right? You learn all the models in medical school, or in business school, or in law school, and you learn how to put them together.

There's no value in that at all, which is why those professions are going through such tremendous pain and suffering right now. The value is in the participatory information of the experience of operating on patients or the experience of dealing with patients. Any patient now and any doctor can use Google or these AI systems to diagnose better than anyone who went to the best medical school.

We all know it. We don't really talk about it because the entire system is upside down in terms of how it's [00:49:00] created. The same in business school, right? That's why people give it a bad rap because we don't care about learning such and such management model. I can learn at JIT with a, again, a laptop at the point that I need it.

The value is in the experience those professionals have and how quickly they have it. I have a friend who has done more than a hundred trials. Okay, it's very rare in business to go to a trial, and most people they settle as a lawyer, and so his information that he has is sort of like what to do if you have to go to a trial, and so then that's like his niche, and he makes quite a bit of money.

As a result of that. And so I think my big takeaway message is we're in this major secular shift from creation of information to curation and from propositional procedure and perspectival information having any value. They have zero value now. They're necessary, but not sufficient for profit.

All profit is now going to derive from participatory. And if you can figure out what I said and how it applies to your business. And move to [00:50:00] where the new equilibrium point will be in your industry, you'll make all the money because basically like, as everything becomes digitized, everything becomes subject to demand side economies of scale or network effects.

And so every business looks like Google, not like Alcoa, even if you have a plumbing business or whatever. 

Jeffrey Feldberg: It's all about the creation, it's fascinating. I'd be remiss if I didn't ask one other question before we go into wrap up mode. 

We spoke a lot about technology, specifically AI. You've been there in the very early days and you're seeing it now come to fruition. And again, what you're going to say today could be at a date tomorrow or a week from now or a month from now.

Where do you see AI? Let's call it in the next year to three years, where is it really going to be? We hear all these doom and gloom, or it's going to be utopia, everything in between. Michael, where are you on that? What does it look like?

Michael Guimarin: I Think it's going to be this situation that we have today where all the people that suffer are sort of out of sight, out of mind. We're individually suffering at the task level, you know, as things get taken away. But [00:51:00] more or less, it'll be like all technology, it'll be a tool that gets deployed and it'll, change over time.

So the diffusion of that tool through the Ecosystem is slow, right? There's still businesses today that operate on paper if you go to the guy that does your clothes, the tailor, oftentimes, it's all on paper. There's no system there. There's no digital system, right?

Computer system would make that more efficient, but it's not deployed. The same will be true of AI. It will be very efficient in some instances, but it will take a generation or two to fully deploy into every business. And so what we'll see is basically, there'll be a lot of worrying and hand wringing right now, and for the most part the impact will be amazing, and yes, there'll be a lot of displacement, but it will not be like this very stark, end of history kind of projecting that people have, right?

I'll give you an example. For decades and decades, we had media from Ex Machina to The Terminator to everything about what's called the Turing Test, which is when a computer is [00:52:00] indistinguishable from a human can't determine a computer versus another human in talking to it.

We had all this media and all this hand wringing about how crazy that would be. We passed the Turing Test like two years ago and nobody noticed. you can't even watch, like, all these people being really upset about the Turing test 10 years ago, 15, 20 years ago like, oh, my God, it's going to be crazy when computers can trick people, and people can't tell that it's a computer, and we passed it two years ago, and nobody noticed, or cares, and that's functionally like, what we're seeing with All of these I'll give another example. So that guy, Mele, who's the president of Argentina, he gave this speech at the World Economic Forum and setting aside the content of the speech, there was a guy who uploaded a video on X of that speech being translated into English in the accent of Mele, live, and then changing the guy's his face.

Like digitally, so that it, there was, it was perfect from a lip reading perspective. That is the most amazing technology that I have seen in my entire life. For like that kind of [00:53:00] manipulation in terms of the universal translator. And again, like hours after that happened, it was like, it was a no brainer.

It's like, nobody cares.

But like Star Trek, there's entire episodes of Star Trek about that capability. we don't even care.

Jeffrey Feldberg: So something that was a fanatical fascination back in the day to a ho hum today, what's behind that, do you think? What's going on with the human condition? Well, you're saying the Turing test back in the day, it was a big deal. Hey, if we ever get to this or we get past this, wow, stop the presses. Let's talk about

this huge implications. And.

Michael Guimarin: Yeah, they're just cognitive singularities. So there are things that you can't think beyond because it's it's where the S curve falls off,

Right? So people lose their mind making linear or exponential extrapolations. It's kind of like 1984 and Brave New World, and people will argue which one is really, better about our world, and then they'll say oh, this one came true or this one didn't, but neither of them saw user generated content. Right? So the idea of like Facebook or Instagram or YouTube [00:54:00] is totally like not a thing in any of those future paced science fiction. And it completely upends the entire idea of surveillance and the panopticon as it was described. and it's just a function of who could say that Napster would lead directly to Uber 12 years later.

It's like very difficult to make those kinds of discontinuous predictions. And yet there's a clear line that connects. Napster and Uber. And so it's just very difficult and I think people get turned up about it 'cause they can't see through a singularity. And there's a ton of 'em.

Like I have one that I have, which is I think that artificial wounds are gonna be the end of the human race, but my sense is that when we actually get artificial wounds, like very little will actually change.

Jeffrey Feldberg: Interesting. Again, the human condition, love it or not, it's always there and always full of surprises. Well, Michael, each one of the things that you just said right now could be another episode in and of itself, but we're into wrap up mode. So let me ask you this. It's really a tradition here on the Deep Wealth Podcast where every guest is asked this question.

It's a fun one. Let me set this up for you. [00:55:00] When you think of the movie Back to the Future, you have that magical DeLorean car that will take you to any point in time. So, Michael, the fun part, it's tomorrow morning, and you look out your window, not only is the DeLorean car there, but the door is open, it's waiting for you to hop on in, which you do, and you're now going to go to any point in your life.

Michael, as a young child, a teenager, whatever point in time you choose, what would you tell your younger self in terms of life lessons or life wisdom? Or, hey, Michael, do this, but don't do that. What would it sound like?

Michael Guimarin: Yeah. So I reject the ring of power and I would get out of the DeLorean and not go. And the reason why is because if I went into the past. Any point that I'd want to go would be before my children are born, and so literally any change that I make would result in the children that I have being fundamentally different, and so I would come back into the present, and they wouldn't be the same kids, maybe different sex or completely different, and I just, I couldn't do it.

So I've already had this thought experiment for years, and then when I realized [00:56:00] after I had kids that they would change fundamentally, I was like, nope, can't do it and then the answer is, you There was a moment when I was laying in my bed as a senior at Princeton that I would go to, or there's the moment that I got my acceptance letter to Princeton as a senior in high school that I would go to. But I know that if I went to either of those positions, I would fundamentally whatever. And what I would say, cynically and hilariously, given, remember what I said at the beginning of the podcast about not knowing anything now versus then what I would tell myself, my younger self, is you are right. that I was totally wrong, but it's just it's totally, because it wouldn't, I wouldn't want to change really anything about my life, actually. That's actually one of the most beautiful things my grandmother gave me through that conversation of what is it that you want to do with your life is I wouldn't want to change a single thing.

Jeffrey Feldberg: And so not to oversimplify or to put words in your mouth, what I'm hearing you say is really enjoy the journey. You're exactly where you need to be as you need to be at where you need to be and go along [00:57:00] for the ride. Enjoy it. Make the most of it. How would that Yeah, I think, yeah, I think it's good. That to me seems rather hedonistic as a perspective, but I think if you think of it like in a, so like on one side you get like into determinism, is the world deterministic, and so it doesn't really matter what I do, and I don't really fundamentally believe in that.

Michael Guimarin: Like I do believe in choices that we make, but I think what's interesting is being able to make a choice and then to be able to go back and see, whether you were right or wrong. And again I view the entire human experience as a big art project, and so the idea that our choices are actually what defines us because more or less we have the same experience as every other person who's ever lived.

I think that is, again what comes down to really interesting. So, I would say, go back and say you were right. So then I would stop stressing about whether or not I was right. And then I would continue to focus on making really fun and interesting choices in the present.

Because, remember, there is no future without the present. And there is no past without the present. So, [00:58:00] really, there is no future, there is no past, there only is the present.

Jeffrey Feldberg: we have this present moment and to say in oversaid kind of saying that's why it's the present or it is a present, absolutely terrific advice. And Michael, as we wrap things up here, if someone wants to find you online, they have a question, want to learn more about what you're doing, they want to reach out, where would be the best place?

Michael Guimarin: Yeah, I'm great on X. Go to at Michael Gimarin on TwitterX. You'll mostly see me commenting about fourth and fifth generation warfare, which is information warfare. I find it totally fascinating, and it seems to be a topic that people care about. That's the best place to find me, and then you can always go to theinfodiet.

com if you want to look at some practical examples of my academic work around how to construct information environments. And so, I think once you've made the mental switch from creation to curation, the next question is like, Well, how do I curate the best environment for myself? And that's the work that I do not pro bono, but it's not, doesn't make me any money, but it's [00:59:00] extremely valuable and people love it.

So I recommend it.

Jeffrey Feldberg: Terrific. And for our listeners, as always, it doesn't get any easier. It's a point and click. It's all in the show notes. It'll all be there. Well, two things, Michael, firstly, congratulations. This is a wrap. It's official. And as always, may you continue to thrive and prosper while you remain healthy and safe.

Thank you so much.

Michael Guimarin: Thank you, Jeffrey. 

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Jeffrey Feldberg: Are you leaving millions on the table? 

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