AI WON'T REPLACE YOU - LACK OF ORIGINALITY WILL

On today’s episode of The Business Game, we’re sitting down with Jonathan Aberman, Founder and CEO of Hupside, a venture capitalist turned entrepreneur who has spent more than 25 years helping launch over 40 technology companies and advising founders on what separates good businesses from truly exceptional ones. 

LEVEL 2: $1M-$3M Dollars. First Teams, First Systems 

After decades investing in innovation, Jonathan returned to the founder's seat with a bold mission: to prove that in a world increasingly powered by AI, the greatest competitive advantage isn't artificial intelligence, it's human originality. 

We asked him whether AI is really replacing people, why originality is becoming the most valuable business asset, the common traits shared by successful founders, why self-awareness matters more than confidence, and what it takes to build a company that stands out instead of blending in. 

Let's dive in,  
With Jonathan Aberman: 

• Why AI is becoming a "sameness engine" for business 
• Why originality will become the biggest competitive advantage of the AI era 
• The founder trait Jonathan says every successful entrepreneur shares 
• Why self-awareness beats confidence every time 
• The biggest reason great business ideas never become great companies 
• Why timing matters just as much as execution 
• Why entrepreneurs need people who tell them the truth 
• The hidden downside of wealth that nobody talks about 
• Why building on top of AI platforms could be a dangerous strategy 
• How Jonathan is trying to build a company that changes the future of work 

If you're a founder, entrepreneur, business owner, or anyone trying to understand how AI will reshape business over the next decade, this episode is packed with practical insights, thought-provoking ideas, and a refreshing perspective on why humans still matter most. 

Connect with Jonathan Aberman:
Website: https://www.hupside.com
LinkedIn: https://www.linkedin.com/in/jonathanaberman/ 

The Business Game is proud to partner with HighLevel, the all-in-one CRM and marketing platform built for growing businesses High Level’s software will drive your customer retention and your profits through the stratosphere - so click here for your 14-day free trial:
https://www.gohighlevel.com/?fp_ref=ribu88 

This episode contains affiliate advertising. The Business Game Group is a GoHighLevel affiliate. If you sign up through the link in the show notes, we may earn a commission at no additional cost to you. 

Transcript

0:00

Success is an intoxicant for certain types of personalities. We gloss over all the moments where we're sitting in a dark room going, "Oh my God, what have I done?" So it creates this impression that, that somehow we had it all figured out. A lot of startups fail, not because the idea is bad, but the timing's wrong. There are a lot of reasons why you fail, and it doesn't mean you're a failure. Success and extreme old age are the two places in the human journey where people become who they truly are. Put somebody who you're thinking about going to business with into an uncomfortable situation and see how they perform. And until you've done that, don't trust them. You can like them, but don't trust them. Welcome to The Business Game, the show that breaks business down into real levels from zero to over $50 billion so founders can see exactly where they are and what comes next. Today's guest is playing at level one, which sits in the zero to $1 million bracket, the founder's startup and survival stage. At this level, you're proving the model works. You're validating demand, refining positioning, and fighting for consistent revenue. The challenges? Doing almost everything yourself, hiring your first team member, and stepping from practitioner into CEO. The goal? Turn expertise into traction and build momentum that's repeatable, not accidental. Welcome to The Business Game. I'm Kaleena Steno. I'm Steve Plummer. Be sure to like and subscribe to the show wherever you're listening. Today, we're joined by Jonathan Aberman, founder and CEO of Hubside. Over a career spanning more than 25 years in venture capital, Jonathan has helped launch more than 40 tech companies, giving him a front row seat to what separates good founders from truly exceptional ones. Now today, Jonathan is back in the founder seat, building Hubside, a business that helps organizations identify, measure, and leverage the uniquely human qualities that create competitive advantage in an AI-driven world. Rather than focusing on what I- AI can automate, Hubside focuses on what humans contribute that AI cannot easily replicate, things like originality, insight, creativity, judgment, opportunity recognition. Let's dive in with Jonathan Aberman. Well, you've nailed it. I think that, uh, it... I really appreciate that you've taken the time to actually think about what I'm doing, you know? Because, uh, th- there's no greater flattery and, uh, sense making than you can create with any entrepreneur, particularly a founder, when you start the conversation by acknowledging what they're doing, right? Because it's such a personal experience being a founder, and, and it's so... It, it becomes your ego. It becomes... It, it's so much, uh, more than just, uh, uh... It's... There's no experience like it. So, uh, thank you for giving me such a, a great way to start talking a- with you about these topics. Yeah, pleasure. It's wonderful to be here. Oh. I, I, I'm looking forward to it too- I... Yes 'cause it's, it's such a counterintuitive thing that you are doing. You know, everyone's AI, AI, better prompts, et cetera, et cetera. You're actually humanitizing, if that's even a word- Yes. Yeah, no, I- AI, so I can't wait to dive into this one. Yes. We've, we've been sort of chatting before we jumped on. Yeah. Mm-hmm. Really looking forward to this conversation, Jonathan. Yeah. So thanks so much for taking time out to share this new journey that you're on with us. Hm. Hm. So- Absolutely Jonathan, let's start from the very beginning. Okay. If we rewound the clock to your childhood What are the key chapters of your life do you think that eventually led you to sitting here on The Business Game today? Wow. Okay. We have an hour together, right? I won't give this to you in one question. No, I won't. Um, y- I think that, um, when I look back at, at my childhood, uh, I think it's fair to say that there was an awful lot of mayhem. Uh, and I think it's true for a lot of entrepreneurs. I, I think that, uh, one of the reasons why people tend to become entrepreneurial is they are motivated to try to control their environment, and I grew up in a very chaotic, uh, family. Um, a lot of chaos. And interestingly enough, both my parents and my grandparents were entrepreneurs. So I grew up in a, uh, a family where the bills were paid with the success or failure of the business. My grandparents were both immigrants. One was a tailor and his own haberdashery, and the other was a furniture salesman and had his own furniture store. And, uh, my parents ultimately owned their own businesses. My father owned a commercial fishery, and my mother owned an art gallery. And so if you can imagine what my childhood was like going from people that smelled like lavender to people who smelled of, uh, lobster and tuna. So when I say chaotic, I mean chaotic. And, and so, um, I think that I always wanted to, I always wanted to matter, you know? I was in a family where everybody was the star but me. I was everybody's caretaker, so I was very driven by wanting to make a difference in a lot of ways. And, um, fast-forward through uni, um, I started out in the States. I ended up going and studying overseas in, in England, uh, for most of my higher education. And I remember when I was, uh, uh, interviewing for a place, uh, at Cambridge, where Anthony ultimately studied, the senior tutor listened to my story of my life and he said, "You're gonna have a really interesting challenge." And I said, "What's that?" And he said, "You wanna be rich and you wanna be good." And he said, "Your entire life is gonna be how to balance those two contrary tensions." And it's, that was the most insightful thing I think anybody had said to me to that point. And when I look at the last 30-so years of my life, going from being a service provider and investment banker, lawyer, uh, partner at a law firm, to becoming a venture investor, and now, uh, a founder- I've also teach. I was a dean of a business school. I'm involved in politics. And what it all has in common, including this company which we're gonna talk about, is, um, I want to make the world better for me being here. And, uh, I, I do that as all the ways I can. Do that in my personal life, my friendships are very important, my marriage is very important to me, my children have been important to me, teaching. It's all about salience to me, right? And we'll get to this in a moment, but the punchline really is the company, which we'll talk about. It, it... but the punchline is almost like, uh, it's almost like a capstone project in a way. You know? In a lot of ways. Yeah. It's, it's, uh, you know, everything's leading up to this moment. In some perverse way, as I sit here talking with you today, it, it, it actually has been like that. Yeah. Wow. Yeah. Mm. What a incredible... Yeah, I... All those little things that you've mentioned even in that, of wanting to be good and, but also be wealthy, that's something I think a lot of entrepreneurs, not all, but there are those that... And that it can be a real challenge when you've got those values that are guiding you as well. So I'm really excited to pull that apart. Yeah. All right. Let's, let's fast-forward to today then, Jonathan. So can you give us the, I guess, the layperson's version of what Hubside does so our listeners know where you're coming from? Absolutely. So the layperson's view, and actually it's not much complex than this- Is that there's a fundamental problem with artificial intelligence now that's not being spoken about clearly. There are many problems, but the biggest problem is it's a sameness engine. It structurally creates similarity. It has to because the way it works. Which means that for most of us, we look at AI and say, "Wait a minute. W- what about me? What about, what about novelty? What about specialists? What about me?" And the way that AI is being deployed right now, I call it the replacement story. They're deploying it as a substitute for human labor. Well, I reject that. I reject that as a humanist, I reject that as a businessman because if everybody has the same tools, Business School 101 says everybody's the same. So how do businesses differentiate? The answer is they differentiate through novelty. So what Hupside, the insight that caused me to form Hupside was I met two scientists at a local university, and they had invented a technology that could take human performance of a task and take AI and perform the same task, and they could mathematically locate the two of them and measure the distance between them objectively. So the more distance, the more originality. So if I give you a, uh, you can play the Hup Checker game right now. You can go and play and answer a question like, "You just met a talking cow. What would you say?" Believe it or not, AI has answered that question. So if you answer that question, your originality is how different it is. Or a product that we're gonna introduce maybe before your, by the time this, uh, segment runs, called Hup Mapper, that can take a piece of content and can identify what's original on top of the AI baseline So, so right. Wow. And it seems so obvious that the world needed to have a way to say, "Humans matter. Hello." But I realized that in the world that we were in, if I wanted to be good and I wanted to fight for humans, I could have a conversation all day long about is it ethical to have a business that's trying to expropriate knowledge to turn it again- you know, to, to make money off of what we all have done? I reject that philosophically. But as a venture capitalist, as an entrepreneur, I said, "I can create a commercial business that can allow you and everybody listening to say, 'Hey, you know what? I have value.' You know how? I took this test, I used this test, and I can demonstrate that I can give you something AI can't give you." And that's what Hubside is commercializing. And as I'm sure you can imagine, it's a big obligation to get this to market because this is a new way to approach AI. Yes. Yeah. And can say, great, be efficient. Be as efficient as you want. We love it. But you know what? If you actually wanna create something special, people are gonna do that. Yes. Okay. And then we can train them how to do that. Yeah. So now you can see how it all fits together, right? You know, the mission, and it's, it is, literally it's capstone project for me, 100%. So can I play devil's advocate here for a moment? Mm-hmm. Why... And I, I guess I'm thinking why, as an entrepreneur who wants to make money and grow and scale and all those sorts of things, why, why should I really care about that and, and not just that the bottom line is, is that AI's making it more efficient, it's cutting my overheads, et cetera, et cetera, et cetera? Why does this originality piece matter? Well, so first of all, the... it's very interesting, and again, I define this. I have a book coming out as well called The Originality Dividend that unpacks this. Silicon Valley in particular has created a narrative called the replacement narrative that has different aspects to it, but fundamentally has to tell the story that AI will replace human labor because the only place you can get enough margin to justify the valuations in this current bubble is making everybody unemployed. Yes. It just doesn't work other- Yes the math doesn't work. Yes. Oh. The problem is that, the problem... So the replacement narrative is very powerful for a lot of reasons, political, economic, business, excitement, bubble, right? The fundamental issue is that the models structurally, and I can tell you this because my scientists, the models fundamentally have a, a flaw architecturally, every single one, up to Sonnet now. They fundamentally all embed the same way, meaning that they all create sameness at scale. It's just the way they work. So, so at the end of this- Process will have a lot of efficiency, but the only jobs that the AI will be able to do well are jobs where repetition matters, where differentiation doesn't matter. And I don't think at the end of the day, that's a world that people want to live in, and people buy stuff, not AI. So my argument is the engines will undoubtedly get more efficient, but, you know, the human mind and the ability to imagine Will continue to have value, economic value. Um, I d- I don't know if it registered over, uh, i- in your newspapers, but over the last few days, uh, w- w- you know, in time where we were when we recorded the show, which would be a while ago now, um, Ford Motor Company came out and said, "You know what? Uh, we just spent a lot of money on AI for quality control, and turns out we need to hire back people." Yeah. Because only people can add that extra insight necessary to truly have good quality control, and they announced it proudly. Um, PricewaterhouseCoopers just did a survey of, uh, jobs in the United States, million jobs. What they're seeing now is that where you have a job where there's a high level of human judgment required on top of AI, those jobs are growing very fast right now, and the wages are going up 60%. Wow. So corporate America's already s- figuring out that the margin for differentiation is in people. Now, we have huge problem with young people and people who don't have experience, which I probably talk on. It's a big social challenge, but the story is far from certain, in my opinion, that AI's gonna take everybody's jobs for all those reasons. Yes. Mm. I, I ag- I agree. Yeah. I, I think... We talk about that often, don't we? Yeah. Yeah, yeah. So, so can I summarize that then that what you're saying is businesses won't win because they have the best AI or the best prompts. They'll win because their people, and it's the human element, are able to see the opportunities, solve the problems, and create value in ways that competitors perhaps won't. Is that a, a good summary? It's, it is a good summary. I wanna add an additional layer to this, which is where original intelligence comes in. Original intelligence is the objective measurement of output, meaning does the process, does the work product, does whatever it is that the company or not for profit or politics, whatever it does, is it different from AI? Okay? Now, I said, is it different from AI, meaning that human talent can use AI to make things that AI on its own cannot make. So really what I'm getting at is that in the world that we will live in, the, what I, the original intelligence story, AI and humans will blend into an augmented co-working that's true co-working, where some people will be naturally gifted, some people will be good at using prompting, some people will be good at using AI as an augmentation and a... That's gonna be the world that we're gonna live in. The, but the human ability to use tools, just like... Listen, if we're successful as a species- Five years from now, we'll think about AI the way you're thinking about your laptops. Yeah. Wow, okay. That, that, that's a- It, it just, it's... Right? Yeah. It's just a tool that you just use. Yeah. Yes. Yeah, w- okay, what if someone says, "Ah, look, this guy's just anti-AI"? What, what, what do you say to that? I'm not anti-AI at all, and I, I, I'm... What I'm anti is, is a replacement story that's creating a narrative that we're all freely substitutable for technology. Oh, yeah. Yes. Wow. Yeah. Yeah. We've never done that before at, ever in, in m- in mankind. Look, I, I was a, I had a ringside seat in the internet bubble. I had a ringside seat. I was one of the leading venture capital lawyers on the East Coast. It was, uh, right in the middle of it. Um, I lived through, uh, the mortgage banking thing. I, I've watched bubbles come and go, right? And I'm an economic historian. That's where I did my, my master's is in economics. We have never ever, as a species, had a tool that we've created this cult-like interrelationship with that somehow the tool is more important than the person. Yeah. And, and, you know, the wheel was unbelievable. The w- computers are unbelievable. Machines, it's all unbelievable, but at the end of the day, humans always find a way to adjust because the tools are basically what we build to make our lives better. And somehow we've lost our way on this one. And so I'm not anti-AI. What I'm an- I use AI all the time. As I say, I'm, I'm in the middle of writing a book. I generate content all the time. I use Claude like my best research assistant. I use Claude as my best thought buddy. But you know, before I send out anything that's a written product, I always... It's mine. It's, it's, it's mine. Is it better because I work with Claude? Absolutely. Of course it is. But it's... Whose product is it? It's mine. Is Claude in there someplace? Sure. Absolutely. But Claude's not the one who's adding the va- Y- you see the difference? Yeah, yeah. Yes. It's- A- and- It's not a purity thing. It's, it's an, it's a hybrid thing. That's where we need to get to, is a happy hybrid outcome. Yeah. Mm. And, and it's yours because it's your original idea that's been, I don't know, supercharged perhaps by Claude or... Absolutely. Yeah. Okay. Yeah. Like, listen, we're, we're together, we're, we're, we're sitting here having a conversation across the globe, right? Um, as humans using technology to share information based upon our thinking, and it's gonna be different than it would be if somebody had taken our script and thrown it into NotebookLM and made a podcast. Yes. Right? Yeah. Yeah. Okay. Yes. There's something, there's something about, about this that's gonna differentiate, hopefully. Yeah. And people... Y- you follow me? Yeah, yeah, yeah. That's what we're getting at, is that doesn't make me anti-AI. I'm not anti-AI at all. I'm, I'm, I'm doing this company because I wanna make money for my investors. I mean, I'm not completely, like, I'm not Dali- the Dalai Lama. But, but, but, but, but I am against a narrative that has shifted the window so that when people talk about AI the conversation begins with, "Well, it's gonna take all our jobs. It's gonna be super intelligent. It's the Terminator," and disables any reasonable conversation about, well, how do we take this tool that could be a really great thing to make humans better, and make it an adversary thing? Because it's not gonna be productive. Yeah. Yeah. And, and so experiences like this with our humanness and our mistakes- Mm and all those sorts of things is, is the richness of it that AI simply can't give humanity. Yes. I... Listen, I think what's gonna happen to our society, and we're already starting to see it, is there are actually gonna be two kinds of originality that are gonna be valuable. There's gonna be originality of authorship, just on its own. Did a human do this? And, and we already see universities, for example, are really into this right now. Did a student do this or did AI? Now, I think that that's important. But the different originality, the originality of outcome, the originality of does somebody find this valuable, is ultimately the originality that's gonna drive our society. So to your point, we're being original together. Ultimately, what gives this value is a listener is gonna say, "This was great content." Right? "I learned something from the content." I mean, the three of us sitting around talking by ourselves, we're original, but original intelligence is the outcome of influencing somebody and saying, "God, I'm glad I listened or watched that show." That's what I'm getting at, and that's what we do, and ultimately I think humans are gonna wanna consume that from people rather than AI, and I think they will pay a premium for that. Yeah. Okay. Yeah. Actually, just on that and people traits- Mm can we just zoom out for a moment? I know Colleen has got a, a, a burning question in a second. But you've worked- zooming out, you've worked with, with so many founders across lots of different industries. And so on that humanness, are there a few specific traits that consistently showed up- Mm-hmm in the people who built companies that truly lasted? Absolutely. Listen, um, I think that there are certain attributes that, uh, that they all share, and then there are a couple of, uh, uh, nuances. The one thing that, uh, I think they all share is mental health. And what I mean by that is the, the, uh, entrepreneurship is incredibly dynamic and very exciting with highs and lows. It attracts people that are mentally well, but also attracts people that have pathologies like narcissism, uh, or sociopathy. Because, you know, when you're a founder and you're hot, y- you know, being fearless is an incredibly useful thing. Yes. Yes. But the problem is that, uh, ultimately a sociopath or a narcissist can't deal with it when facts change, and they... You know, and ultimately, if you're an entrepreneur, facts change. Yeah. Yeah. So, uh, you know, so, so number one for me has always been, does this person have the ability to abstract, to, to think about themselves in the broader sense of things and gather data? Otherwise, or other words, self-awareness. I believe that self-criticism, self-awareness is the most important attribute I've seen in every successful founder, 100%. I've never seen somebody be successful long-term without that because any startup business is not a linear curve. It's a waveform and it's mayhem, which is what attracts people who are mayhem wired. Yes. Yeah. Like my parents. Right? I mean- Yeah they were entrepreneurs, 'cause they were, God love them, they're both deceased now. They were, like, they were crazy. They just were. You know, they were fundamentally... They loved it. They lo- I, you know. So, so what- So- So what does self-awareness look like then? If, if, you, you know, there's, well, she's self-aware, he's not self-aware. What, how does that show up in, in those founders, the successful entrepreneurs? So generally it turns... So the, the biggest tell in my opinion for self-awareness is the ability to take data and change behavior. Ooh. Ah, gotcha. That's, that's the be- And, and it can be a little thing or a big thing. You know, uh, uh, I will, uh, for example, use, uh, in, in pitch meetings over the years I've, I've used, uh, I've used being unpleasant sometimes as a way to see how they handle. You know, throw a fact at them, throw a situation to see how they react. Or go out with them to a restaurant and see how they treat the water boy, right? Something, just something to see how they handle themselves. Now, you'll hear people say, "Oh, what you're really talking about is empathy." And, and I would say, yes, empathy is related to self-awareness because you can't really be empathetic if you don't know how you would feel. Yes. Right? Yeah. So to me, it really does come down to people, people tell you how they are when they don't realize they're telling you how they are. Yes. Right? So you learn more about a person when they're under stress than you will ever learn from them when things are good. You'll learn more from them by seeing how they treat somebody who they don't think they owe anything to than you'll ever get them... Y- you know, it's- People reveal themselves very quickly, and if they reveal to me that they have the ability to abstract and think about how their actions affect others, that to me is the most important thing for a founder, 'cause a founder has to orchestrate a startup. Yes. Yeah. Wow. You know? The other attributes that I've seen that are also really important is, uh, a fundamental ability to fail upward. You know, it- entrepreneurs have the ability to take a failure and learn and, and progress upward. I've s- generally see that. Um, if you remember, uh, when we were younger, Thousand Acre Woods and Winnie the Pooh and, and Tigger. You know, the Tigger's the entrepreneur, you know, being irrepressible. Um, people think and say extroversion. I don't think so. I know successful introverts. People say risk-taking, and I say no. Entrepreneurs don't take risks, they take qualified risks. They're risk managing all the time. So those are the things that I've seen be successful, but the, the ability to be agile comes from self-awareness, and I've never seen a successful founder who didn't have the ability to modify their behavior long-term. And what about... So with those, those traits we sort of just touched on, they're all things that you learn over time as well. Like, yes, you're born with them to a, to a degree, but would you say that there are some strategies around, you know, self-reflection and how to fail upward and those sorts of things in your own personal experience, or what you've witnessed? So I think that, um, what I tell, uh, people that I'm mentoring, and I still do that a lot, is that, um, you really have to be willing and able to look stupid and just get over yourself. So true Because, you know, it gets us a lot. And so I'm a, an executive residence with a wonderful university in Rome called John Cabot University. It's a, a little gem of a university. It's a business school, liberal arts school in the middle of Rome, but it's all in English 'cause it's American accredited, so I can teach there. And I, I meet a lot of 20, 21, 22-year-olds there, and they're in such a rush. You know? They're in such a rush. "Oh my God, I'm, I gotta..." You know, like the Italians say, "Piano, piano." You know, slow down. Slow down. You know, just take a breath. You got some time. Make some mistakes. It's really, really hard, I think, because if you get advice from what I call Victory Lane entrepreneurs, people like me, who look like me and sound like me, a lot of us have the tendency to talk about our success like it was foreshadowed and it was gonna happen for sure. We gloss over all the moments where we're sitting in a dark room going, "Oh my God, what have I done?" Yeah. Right? Yes. So it creates this impression that, that somehow we had it all figured out. And what I always tell my students is the reality is that everybody around you who's not psycho is also terrified. You know? Thank you, Miss Fran. Yeah. That, that makes me feel better, yeah. Yeah. No, but you know what I mean? I mean, that's the thing. If, if you don't have the imposter syndrome, then you're probably a sociopath or a narcissist. Yeah. There you go 'cause if you're self-a- right? 'Cause if you're self-aware, you're going to be, I'm like, listen, I have moments. I've been at this for a long time, but this is a software startup. This is the first time I've been the product guy, right? I've been advising people for years. This st- this technology was so important to me, and I wanted to commercialize. I wouldn't trust anybody else to do it, so I left my fund to start this company as a founder. That's how important this was to me. But I have moments where I'm sitting with my engineers and thinking, "Good God, I'm desi- you know, I'm, I'm developing these products." I'm looking to the right and looking to the left. I'm like, "Oh, no, nobody has a better idea." Maybe I shouldn't say this on the air. I've just, I just undermined credibility with my entire team, but, but you know what I mean. It's, it's... If you don't have those moments, there's something wrong with you, I think. Yeah. Yeah. Yes. I have a, a question. Um, it's, it actually is als- also stems from a personal experience, so I had a really great i- we sort of talked about this briefly- Mm. Yeah before we jumped on. We were that excited to speak with you, Jonathan. We were- Oh, thanks talking about all these Yeah. Great. Um, so across all of your years in experience, what would you say is the single most common reason a genuinely good idea never becomes a great business? So- Oh. Mm-hmm for, for reference, I had a business. I, you know, I went to my friends, some family. Everyone said, "Yes, go for it," and I, I, I believed- It's a great idea. Great idea It's a great idea. I believed in it. Yeah. I built this community, and then when we finally launched, no signups. So th- then that's not a, that's not, that story's not just, you know, singled out to me. There are people tuning in all across the world listening to that going, "Yeah, I've been there." So what is it that you've seen that is a differentiator there? Wow. There's, there... Look, I mean, Steve Blank talks forever about product market fit. You know, it's almost to a, to, to a cult, right? So the short answer is product market fit, which, again, is a great Victory Lane entrepreneur advice for thanks a lot, uh, if- Yes. if you could tell me how to do that. I know. I've heard that statement. Anyway, right? Oh, that's the answer. No, it's- Right. Yes. Oh, yes. Yeah. Product... Damn it. Yeah. I, I should've done- Yeah. So, um, so I think there are, there are a number of, um, reasons why that happens, uh, that are, I think, important to think through. Uh, I think the first one is, you know, sometimes a great idea doesn't necessarily arise at the right moment. So for example, just to push a little bit of spoiler to myself, I think, and you think from our conversation, that what Hubside's doing with its products is a great idea. But dependent upon how the world feels about the AI replacement narrative, I might not get enough oxygen to raise enough money to make this a big enough business to last long enough. You know, there's timing with any startup. You can be right about the idea but wrong about the market timing, and I think that that is something that, frankly, you can't really know- If you're doing something that's truly new, you can't know because the market doesn't know your technology exists, so how can you possibly know whether or not the market's ready? So, so a lot of startups fail not because the idea is bad, but the timing's wrong. Okay. Right? Yep. Uh, so that's number one. Number two, startups fail, uh, because execution's really hard. Yes. And, and there's no shame in that. It's just, it's hard. I mean, there have been a lot of mistakes that I could have made over the last year that I haven't made because of experience. If I was a less experienced founder, I... There are a lot of mistakes that I could have made that would have been... You know, for example, uh, early on I was interviewing an engineering team and, um, uh, to, to build my first prototype, and they sent me a contract that was just absolutely ridiculous. And, and, and somebody inexperienced wouldn't have thought about the IP provisions, you know? I immediately knew that they were trying to steal my intellectual property. So I, I, I shut it down, but if I was inexperienced, I might have given away my technology before I had a chance to develop it. I could go on, but you see what I mean? Yes. It's, it's, it, it's just there are a lot of reasons why you fail, and it doesn't mean you're a failure. Yes. It just means that- That's that getting over yourself element for whatever reason, the play wasn't right. So just speaking of that, I mean, you've gone from experience of, of, of building businesses, being an investor, and now you're, you know, back at level one in that- Mm-hmm precarious almost founder stage. So- Yes what has that complete flip of, uh, an experience been like for you, and what have you learned about yourself in the process? Well, I've learned that, uh, I, I can't stop myself- from taking on new challenges. And I, and I think about my tutor back at Cambridge with Wright and, uh, and Rich, but Good and Rich. You know, the more granular answer is the funny thing about being a really good coach is when you become a player again, uh, 'cause I've been a player before, you find yourself talking to yourself a lot You know, I, I mean, it's sort of like I'm, I'm coaching myself is a b- and this is what I get to self-awareness, you know? Um, having said that, there are some amusing moments. Uh- Um, my wife Veronica, uh, Kane is, is incredibly accomplished woman and, and a great lawyer, very s- very smart, and she's been my partner f- in all this stuff for years. She's a ringside seat, and she's been watching me mentor the startups. And I had a moment about six months ago where I was raising the first round, and I was just like, "Damn it. People aren't calling me back. They're not calling me back," and I'm starting to rail. And, and she looked at me, she said, "You know, who's your Jonathan?" I said, "What do you mean?" She said, "This is what you do all the time with your entrepreneurs. Who's your Jonathan? Who y- who, who, who's doing for you what you do for all these entrepreneurs?" And I said, "You?" She said, "Oh, no." So I think that that's probably been the biggest thing, realizing that, um, even though I'm really experienced, I need to have a, a, a few people that I can confide in when I'm having these moments. So I've built a little bit of a kitchen cabinet around myself of people that I can be honest with and say, "Oh, Christ, I don't know what to do. What do I do?" And be able to work it through with them without, uh, feeling embarrassed. That's probably been the biggest thing. Yeah, so th- that's interesting. Is that a, a mistake that... Well, maybe it's not a mistake. Maybe it's an oversight even in the hustle of everything. Is that an oversight/mistake that a lot of entrepreneurs make, they don't have a support network where they can ask questions and not feel silly? Absolutely. It, it comes back to the feeling stupid before, and this is again the, the mistake we get from listening to victorially entrepreneurs to teach us how to be entrepreneurial. Because you get the impression that they did it... Look, I know so many successful people because I've been at the investing game for a while, I've been around entrepreneurship for a long time. Success is an intoxicant for certain types of personalities. Yeah. Yeah. They can't believe anything other than, "I was destined to be a success." So that when they're asked how it happened, they tell the story of the single combat warrior. It was me. It was me, me, me, me, me, me, me all the way, and we see that now in the tech bro culture on the West Coast. It's not just Sam Altman or it's not just Elon Musk. I mean, there are, you know, like hundreds of people, thousands of people doing their thing, making them who they are. But you don't hear that. So the, the- so it's the cult of the individual. The, you know, in the United States, the man on horseback, the cowboy. That's the way... So, so there's this macho, and I'm gonna use it not masculine, but this I can do it all myself. So to show weakness undermines the entrepreneurial image. So yes, I think it's a mistake to buy that myth. But the other side of it is, is that understand that just because you want someone to be your, uh, your mentor doesn't mean that they wanna be. Yes. Nor will they necessarily be any good at it. So, and this is the other s- mistake I, I see entrepreneurs go from I don't need anybody to I need a, I need a mentor. I get this a lot. People come inbound, "Oh, do you have time to mentor me?" It's like, "Honestly, no. I don't know you, and I don't have time. I, you know, I'm sorry." Uh, and they, you know, they look... It's, it's sort of like, you know, an orphan looking for parents. It's not a good, it's not a good look. So to me, the best way to find good mentors is if you're in a tech ecosystem or an ecosystem, find people who have grown businesses like yours and reach out to them and see who truly is self-aware and engages with you in a real way Right? Not, not in a, "Oh, yes, I'm wonderful. Thank you for talking with me," but really engages. The one person out of 10 who actually engages, those are the people you should surround yourself with, and that's where your entrepreneurs come from. Maybe your first angel investor. Probably not a venture investor, because they have to make money for their LPs, although they can be useful. Maybe an old professor, maybe a friend who was successful. But you're gonna need some people that you're gonna be able to be vulnerable to. And by the way, every startup is a family business. If you have a significant other, they're in the business whether you admit it or not. The ups and downs are gonna affect their lives, so don't make pretend that you're separate from the family, because everything you do affects them. Understand that they're putting as much into it as you are, even if it's not seeing you as much, or doing more... You know, whatever they're doing. Yes. It's a family business. Yeah. Absolutely, yeah. And I'm glad you mentioned that about... It isn't... I think people go, "Oh, I should just, I just need to get a mentor." But it's actually a bit of effort to find that person, to find the right fit. It's, it, it takes a bit of getting your- putting yourself out there and trying to find someone that's actually gonna fit the mold with you and your lane and where you're headed. Or, or a support team. Timing. Yes. Yeah. Or a team. Yeah, yeah. One of the things that I do, maybe I shouldn't give this away becau- But, well, I generally, if somebody gets through the f- the filter, as it were. I mean, getting through the filter is not sending me a message on LinkedIn saying, "Can I pick your brain?" I mean, no. That, um... Or, or, "I, I'm looking for a job, can I talk with you?" That is not getting through the filter. That is basically telling me that you wanna create a transactional relationship, and I don't need a transactional relationship with a stranger. I have more than enough transactional relationships surrounding me already, right? What tends to work, and I see works really well, is somebody who comes inbound with an interesting problem or interesting challenge, and manages to communicate that they're really just looking for some, some advice, right? Or they come inbound with a really well-framed reason why they want my advice. Or I, I'm at an event and somebody comes up to me and says, "You know what? You're doing something that I think is really interesting. I'd like to help you do that, and here's what I can do to help you." Or, "You know what? I just wrote a book I think you should read," or, "You know what? I just thought of you for an article." But in other words, look at building a relationship as building a relationship, not as a transaction. And because if you, if you approach somebody like it's a transaction, then it's like, "Well, why? I, I'm sorry. I..." But, you know, people who I... And 'cause I've, I, I do have a fair number of people that I mentor professionally and just for fun. What they all have in common is somewhere along the way they communicated to me an understanding of my worth to them, and they gave me a sense of their worth for themselves, and I saw a way that I could actually have a relationship with them that would be interesting and enriching for me as a person. Yeah. Yes. And you can't do that by saying, "Hey, I need your advice," or, "Hey, I, I need a job." Yes. Yeah. It's a human element, right? Yeah. Yeah. It gets back to that human element- Yes that we spoke about. Yeah, right. Absolutely. Yes. Yeah. Absolutely. Which again, AI will never be able to do. I'm sorry. That's right. Yep. No, I totally agree with you there. The Business Game is proud to partner with HighLevel, the all-in-one CRM and marketing platform built for growing businesses. With CRM funnel, website, and course builders, marketing automations, email builders, and so much more, HighLevel Software will drive your customer retention and your profits through the stratosphere. And HighLevel is fully white label, which means you can brand the platform and mobile app with your logo and company colors, and then resell it to your customers for a monthly subscription. Ready to go HighLevel? Click on the link below to begin your 14-day free trial. Um, so back to, just circling back to that level one, um, that Steve spoke about. Um, so you're sort of in that startup and survival stage, which is really that period where you're still, you know, in active validation mode. Mm. What is the hardest thing that you're trying to figure out right now? Me personally, or just in general? Whatever it comes to. I- I, I think i- in terms of- Well, I, I- HubSpot I think at the end of the day, um, the best way to think about a startup is a startup s- doesn't, isn't a business when it starts. It really is a customer discovery activity. It's a customer discovery activity. Then, um, it's an initial prototype activity while you're doing market discovery. What turns a market, what turns a s- a product discovery startup into a business is customers. Until you have customers, you don't have a business. Stop. Until you have customers that are repeatable, you really don't have a business, 'cause until you have that, what you have is, frankly, a hobby, at best. You know, in the United States, tax law, if you have something that you do for a few years, you don't make money, the presumption is it must be a hobby. 'Cause why would anybody do something for an extended period without it being, uh, profitable in some way, you know? So, um, if you're doing a startup and you can't find, once you have a product to show, within some period of time, months, six months, whatever you wanna give it, you don't have people saying, "Oh my God, I want this," then it's not a business. It's a hobby, and it's time to do something different or to ask yourself why. Um, and I think that's probably the most important thing. And, you know, entrepreneurs will say to me, "Well, how much revenue do you need to have before I raise VC?" Hear that a lot. And you know, it's not a number, it's momentum. It's not a number, it's is this replicable? You know, you can have two customers, but if those two customers love your product, and there are 100 like them, and you're already in touch with 50 of them, you can probably raise money, 'cause an on- you know, an investor can say, "Oh yeah, there's a plan." But two customers that are isolated that you can't repeat, you don't have, you, you haven't demonstrated something scalable yet. So it's customers and scaling. It's the, um... You know, best way to think about it for me is money is an asset to scale a business where you have the infrastructure to scale, and you just need money on the balance sheet to scale by acquiring resources to take what you see in front of you and grow it. In other words, growth is more people wanna buy your stuff that you currently have available. Growth pulls you forward. You don't create growth by raising money. Growth pulls you into money, and that's, I think, the biggest mistake that entrepreneurs make is, "Oh, I gotta raise money because X." No. You raise money because you have customers pulling you into needing to raise money because you have more customers available and you have money on your balance sheet to satisfy. And getting to that point is where most startups fail, actually, 'cause that's hard. You know? That's hard. That's the hardest challenge. Yes. Yeah. C- can we dive in a little bit here to the, again, the human side of things, the, the, the personal part of your journey? Yeah. Um, yeah. So you were around founders, ambitious, um, entrepreneurs, et cetera. So has being surrounded by those sorts of people, has that, I, I guess, almost changed the way you see success or happiness in your own life? Well, uh, it's interesting. What I have seen in my life is that, um, success and extreme old age are the two places in the human journey where people become who they truly are. Wow. Because when you're very, very old, you just frankly, for a lot of reasons, the... All the artifice disappears. You are... You know, it's like I am who I am. Yeah. Yes. Like me or not, I am who I am. Yeah. When people become financially successful to the point where they don't have to worry about eating, what I have seen is that the people who were jerks before become spectacularly spectacular jerks. Spectacular. Just spec- I mean, you just... They do things that just like how can you be that ungracious about what life has given you? But they, they can't stop because they were mean and angry before they became wealthy, so they're still mean and angry. The people who are, uh, driven by a sense of community empathy tend to just become more who they are. So great example, years ago, uh, one of my early deals, two founders. Um, and, uh, uh, one was... They both had grew up in underprivileged backgrounds. One was just incredibly paranoid, always felt like the world was trying to screw him. Very driven by status. The other was just driven by mission and just wanted to do good things. And they became spectacularly successful. One became a CEO of, uh, and board member with a private jet. Just he did all this thing. The other guy quietly funded a charter school in, in New York and put hundreds of kids through university. Oh, wow. You know, quietly when the earthqua- when the, uh, hurricane hit Puerto Rico, got a couple desalinization trucks and power trucks and just shipped them to the island so people had water and power. Never talked about it, ever. Oh. Wow. I could've told you before they got rich what they're gonna be like now. I could've told you. So money is an intoxicant. It just is. And so that's the biggest thing I've learned. And the other thing I'll tell you is that the other reason why money is an intoxicant is it becomes harder and harder and harder to make friends once you have money. Yes. It's really, really interesting. And you might say, "Well, poor boohoo. You know, I should have that problem," and I understand that, but it's important if you want to approach entrepreneurs to be mentors or wealth people, understand that they are surrounded every day with people who are asking them for something. Their lives... I see it, you know, because I've been working with this family office venture fund. I see it. People expect that a rich person... What's $250,000 to you? What's $10,000 to you? It's, it's... You know, they're, they feel like, uh, their cow's being milked. You know, and, and I'm saying this humbly, just not to say you should feel sorry for them because it's like millionaire tears, but just understand the mindset that I've, I've probably seen really, really good people get really, really sad from money because they lose the ability to meet strangers and feel trusting enough to start a relationship because in the back of mind they're wondering, "What does this person want from me?" And it takes away one of their big life joys, which is just being a regular person and just getting to know people. It's really interesting. Yeah. Wow. Mm. That's some huge insight, isn't it? Mm. Yeah. Mm. So outside of business and tech- Mm what do you do that completely switches your brain off? I'm interested to know this. Well- I, I can move the, I could move my chair and you could see all my guitars. I, I'm a musician. Oh. I, I play in a band here in the States called Two Car Living Room. Um- Two Car Living Room? I, uh... Two Car Living Room. Wow. That's a great name. So, you know, there's, we, we have the phenomenon of garage band, right? Yeah, yeah. You know, maybe they have it over where you are as well. You, you know, when you're a kid, go out in the garage. Yes. Play in the garage. Yeah. Well, when you're an adult, the band rehearses in the house. Yeah, totally. Not in the two-car garage, Two Car Living Room. So- That's great um, you, you, you can actually find, I've got a couple of albums if you look on Spotify. And, uh, um, music is my, is my thing, and, um, that's what I, that's what I do. I've got a band and we play every couple months, and it's, it's my thing. I love it. And, uh, yeah, I do. I really do. Just love... There's nothing as good as playing a solo and getting to the end and somebody saying, "How'd you do that?" And I say, "I have no idea." It just happened. Wow. Yeah. That's cool. It's magical. Yeah. That's- Oh, yeah. Yeah. Oh, yeah. And do you feel like that really fuels that creative for you? Especially when you're bogged down in that, like, level one, you're really, like, you know, you're doing the nitty-gritty stuff, do, are you finding that that's, like, a really nice creative outlet for you to sort of- reaching yourself You know, I, I, it, uh, absolutely is an outlet. There's no doubt that, uh, you know, playing Purple Rain is a lot of fun- and it brings me out of myself. There's no doubt. But the truth of the matter is that when I look at my life, you know, I almost took a run at being a professional musician, and I realized a number of years ago, one of the things I loved about being a musician was being in a band. You know, the shared experience, the creative experience. And what I realized is I've been putting bands together my entire career. Yeah. Yes. That's what venture capitalists do. That's what professors do. That's what, that's what CEOs do. I have my band now. I have my band. I've got my technical founders. I've got my, my c- you know, Dan and Adam. I've got Eric, my, my founder who's the sales guy. I've got the tech team. I've got my band. I'm the, you know, I'm the lead guitarist in, in a band called Hubside. And, um, so it, it's more of a continuum than you would think it would be. It's just different manifestations of creativity- Very cool which is why I started a company to fight for creativity, not surprisingly. Yeah. Yes. Very cool. Yeah, so Jonathan, just on that, you, I, I guess as you mentioned, you touched on it, you, you've built a career around spotting potential in people and bringing them together. Was, m- for you, was there someone early in your own life who saw something in you before you saw it in yourself? Well, I mentioned John Hopkins, my, uh, my tutor from Cambridge. I, you know, it's a very interesting thing to unpack that moment a little bit. So if... I was, uh, working in London in the investment banking industry, and, um, my dad had been a lawyer and, uh, so I always kind of thought I'd be a lawyer, too. And one day I sat down with a colleague at one of the big banks and I said, "You know, I'm, I think I'd like to go to law school." And he said, "Well, if you wanna go to law school you should talk to a friend of mine." And he gives me this guy's name and a cell phone number, and I call him up, and I literally... This is before the internet, that's how old I am. I didn't know who this guy was. It was just, "Call my friend John Hopkins and go and see him." So I call up Mr. Hopkins and he says, "Oh, yes, please, come and see me," in that wonderful Brideshead Revisited accent that only a, a, a Cambridge don can master. I'm gonna try to, uh, imitate it. So one day after sch- you know, after I finish up work, I get on the, the train, I go up to Cambridge, and I'm, I'm sitting in this man's office and the fire's going and we're drinking some, some port, and he's just asking me about, you know, um, my life. I just thought he was an interesting person. He was a friend of my friend. We're just talking for 45 minutes, and he gets to the end and he looks at me, he says, "Right, you'll do." And I'm thinking, "I'll do what?" You know. He said, "Well, you'll do," and I said, "What do you mean?" He said, "Well, I assume you'd like to come here." And I said, "Who wouldn't want to study law at Cambridge University?" And he said, "Exactly. It's settled then." So, you know, I mean, my God. And, and so I'm there literally gobsmacked in the moment thinking, "How the hell did this happen to me?" And then that's when he said, "But I wanna warn you that if you do this, you're going to be going on a life journey that's gonna challenge you in a way that you're not thinking about, which is how to balance being good and being rich." And, and so, you know, there have been other people along the way. I mean, my wife, uh, Veronica, has been an unbelievable mentor to me over the years. And, you know, um, uh, my current co-founders. Um, I, I could go on. I've been very lucky. People have invested in me along the way But if I was gonna identify one person in my entire life who set off on a new trajectory and really got me, it would be John Hopkins from Cambridge. That guy changed my life. Mm-hmm. Yeah. Absolutely. Yeah. Wow. That's incredible. Mm. It really was. So what problem are you, as a founder, trying to solve within the actual business of Hupside at the moment? I know I sort of asked that before, but I feel like I didn't really quite get an answer- No I was looking for, so I'm circling back. I hope that's okay. The, the, the technical problem or the bus- or, or, or my stage problem? Um, I... Let's do both. Yeah, yeah. I think that'd be interesting. Yeah. Well, so let's... They're, they're, they're related, and, uh, so here's the interesting challenge that this particular business and I and, uh, we have. Okay. Which is that this literally is Kleenex when the entire world has a cold. It literally is. I mean- Love that if, if you buy my worldview, and a lot of people are starting to buy it, if you buy my worldview, our technology is literally the only way right now to see whether or not a human's creating original content that exceeds the AI baseline. Only one. You know? It's patented. It's, it works. Well, it should literally be everywhere. Yeah. Well, I am sitting with my team, you know, Don Quixote and his wild, you know- Viscount Viscounts, trying to, to per- you know, get a standard that could change the world out into the world in a very short order, right? So, so my biggest, um, fear is that we won't achieve enough ubiquity quick enough to give us all a way to push back against the replacement narrative. That's what keeps me up at night, if that makes any sense at all. Back to Mr. Hopkins, want to be good or want to be bad. I want to s- I want to see this everywhere as fast as possible. So the technical challenge is, how do you accomplish that when you don't have $100 million? And the answer is, we're doing it by building the products that we can build quickly with a small team. So the first product we built was Hupcheck, which is a really cool game that, by the way, I encourage you to, if you go to the website hupside.com, you'll see you can try it and see and, and get your own IOQ score. Well, so we built that, and we built a, a way to deliver that to enterprise. Depending upon when your show airs, we will have introduced or will be introducing a second product called Hupmapper, which will be a consumer-focused app that will allow you to go to the site, put up to 2,000 words in it, and immediately see how original it is compared to AI. Ooh. Wow. That's cool. Right? Wow. But both of those products ultimately are products that should be scaled into big enterprise- infrastructure, which I can't do with the money I have available right now. So, so it's, it's really, um, I'm trying to take what should take five years- Mm and I'm trying to almost... Do you remember Shrek? Yeah. Remember the movie Shrek? Yes. Remember Donkey in the back going, "Pick me, pick me, pick me"? Yeah, yeah, yeah. We're, we're basically Donkey. Yeah. We're, we're, we're, we're jumping up and down saying, "Pick me." But, and, and, and what I'm hoping is that over the next few months it becomes obvious that the world needs this solution, and larger companies, financial investors give this thing the $50, $100 million it needs to become ubiquitous so I can satisfy my mission. That's where we are as a business, and if you wanna know the truth, that that's what, when I wake up at 3:00 o'clock in the morning, that's what I'm worrying about. Not worrying about whether or not the product works or my team. I'm worrying about whether or not I'll be able to deliver to these wonderful people this crazy outcome that, um, ain't gonna, you know- Tell, well, tell your friends. Everybody who's watching, go try the product and tell your friends. Help a brother out. Yeah, absolutely. Yeah. Well, I, I think it's a, it's a really interesting thing, though, this... Is this the next wave of AI, right? Is, is this the next part- Yeah of what humans need to do to, to use the AI tools better, is to, is to find out the originality of things? And, and in so doing so, it's that whole, you know, y- where your attention goes, success follows kind of thing, in that if you're doing more about originality and so forth- Yes um, using this tool, then you potentially will become more original in your work. Yes. 100%. So in my, in my book, um, The Originality Dividend, um, I actually come up with a really simple paradigm that I basically call the originality loop, which is a five-step loop that it's not complicated. You know, think. You think first. You just think, and then you write... Yeah, you write down, and then you write down a draft of what you're thinking. And once you've done that and you looked at that and you think, "Yeah, okay, this is what I want out of the AI," then you go and you ask the AI to challenge what you wrote. You don't ask them to do it for you. You challenge what you wrote. "Okay, how do I work with you? Okay, look at that. Look at that. Does that make sense?" Use the AI as a sparring partner. Yes. And, and then once you've got that and you've pushed it and it's pushed you, then you take the work product and you own it. You own it. You, you do the finishing work, and you own it, and when you hand it out, it's yours. You did it. That, you were the creative. That is a- Yes. You know what I mean? That, that is to me that, what I call the originality loop. That is so bog simple, but yet if we could just get students, if we could start evaluating students on, "Don't... I don't care whether you use AI or not. Knock yourself out. Did you give me something that fundamentally I couldn't have gotten out of Claude? Yes or no? If the answer is no, go back and try again, because when you leave here, if you can't give me something I couldn't get out of Claude, you are gonna be... You're not gonna get a job, and you're probably gonna have a very unhappy life, right?" But the good news is that when you look at it and you look at people, I'm not talking about g- I'm not talking about genius creativity. I'm not talking about Liberace. I'm talking about something as simple as, "Where do we go get coffee today?" Or, or, um, "Let's talk about this with the customer a little bit differently." Little novelty moments that we all do on a daily basis. That's what I'm getting at. We all have that. We all have that. Absolutely. Mm-hmm. And I imagine the pressure that you're feeling with getting this to market is also gonna be being pushed by AI is moving at light- you know, lightning speed. Mm. So you've gotta keep everything moving quickly to get ahead of it, or just to keep up. Well, yeah, I think that's true, but again, be careful, you may be falling into the replacement narrative. Yes. No, thank you for pulling me up on that. Yeah. Which is, which is, is this idea that we are rushing towards a singularity. We're running out of time. And don't forget that some of the people that are promoting the replacement narrative basically do have an almost religious view that AI is the next life form and, and I mean, Elon Musk has actually referred to humans as bootloaders. You know? Sure. He has, on record, and I mean, more than once. So, um, y- you know, I think that the reality is, is that, as I say, yes, there are generational improvements, yes, Claude gets much more competent, they all get more competent, and so forth. It's really important to internalize the fundamental structural architecture of the large language models has not changed. They are sameness engines at scale. Now, you might say, "Well, Jonathan, maybe they'll change the architecture." Maybe they will. Maybe they're, they're trying different things now. It will be something different now. Maybe they'll figure it out, maybe they won't. But why do we assume that once they figure it out, that originality generated by a computer is gonna be more desirable to humans than originality created by humans, if we're ultimately the consumers? Absolutely. Mm. Yep. Yeah. Uh, you may have already answered this question, Jonathan, but if a founder came to you today and said they want to build a company that creates value rather than just riding the current AI wave- Mm what's the first question you would ask them to stress test whether they actually have something differentiated or not? 100%. The first question I would ask them, if you wanna go, is, and, and I see this a lot with entrepreneurs now, if you wanna go into the AI industry to w- to, to, um, try to participate in the bubble, um, and your plan is to basically build a service layer on top of one of the large models, go do something else. Because the, in order for, in order for OpenAI and, and Anthropic, and the rest of them to justify their valuations, they're gonna have to keep accreting whatever they can accrete in the value chain. Whatever they can automate, they're gonna try to automate. So if you're gonna create a process, uh, where you're using underlying their tools to do a service layer, make no mistake, they will try to figure out a way to accrete into it. You won't have something protectable. You just won't in the long term. So, um, whatever it is that you wanna do, um- It needs to be something that fundamentally the big companies can't take from you. Listen, number one question that excited me about the technology of Hupside, the number one question I asked when I was thinking about being an investor before I became the founder, God help me: Is this technology independent from all the large language models? Is it independent? Would it operate without it? And the answer is, it's a brand-new model. It's completely self-contained. We don't use anybody else's technology at all, and if they all went away, we could still operate our model. So it's original, right? So, uh, there are some AI companies raising money now that are coming with new types of models. Great. So, but now pull it back. There's a lot of money to be made by being the service layer on top of AI, meaning being a consultant, being a value-add person using AI well. There's gonna be a lot of opportunity, just like there was when the automobile popularized. There's a whole industries that'll get created. But if you're asking me if I was gonna be a tech founder, do an AI company, unless you have something that cannot operate unless you are... have access to the gen AI models, and you're planning on doing a venture-backed deal, don't do it. It's too late in the cycle. They're too entrenched. Yeah. That's great advice, 'cause I, I'm sure there's lots of people going, "Oh, cool, there's an opportunity here," and it's not actually yours. To be fair, again, there is an opportunity, but the opportunity is to think for the next cycle. See, that's the advantage of having lived longer. I watched the internet. You know, the internet bubble went like this, and then it ended. Everybody's like, "Oh, it's done." It's, it wasn't done. What was done was the financial bubble. The, the ca- the, the dark fiber was there. The technology was there. Google, Facebook, Web 2.0, I mean, it was all there. The bubble ended. You know, Cory Doctorow's written about this, uh, a lot, and he is unapologetically saying the bubble will end. I agree with them, the bubble will end at some point, but AI is here forever. Yes. Yeah, it doesn't disappear. Mm-hmm. Yeah. Yeah. It won't disappear any more than the internet disappeared. That's right, yeah. Yeah. Um, looking across the 40-plus companies that you've helped launch, what does a founding team that consistently underestimates the importance of culture and human insight actually look like in the early days? And what are the early warning signs to, to look out for? Oh, geez. So I, I, I actually had one startup that came to pitch me and, um, there were two of them, and they started to talk about the technology and I thought, "Wow, this sounds really interesting. Tell me more." And they told me more, and I thought, "Oh, maybe I'll invest some money." And I said, "So who owns what?" And one guy said, "We're 50/50," another guy said, "We're 70/30." I was like, "What?" And they looked at each other and said, "What?" And I said, "Guys, who owns what? Is- I'm 50/50, you're 70/30." I said, "Listen, I think you guys need to kind of have a conversation." So I, I, I walked out of the room and I left them in the conference room. Uh, and I walked out and I'm standing there with my, uh, my, my assistant, and they're yelling at each other, and then one of them picks up a chair and literally destroys it on the, on the, on the conference table and storms out. And I turned to my assistant and I said, "I guess we're not doing that deal." Right? Yeah. So, you know, it's a great story and it, it highlights that what generally happens is the founding team- Unless they come together and really have honest conversations about who's doing what and who owns what, and tries to gloss it over, the stresses will show relatively quickly. And, and once the stresses start to show, a company will blow up. So, um, that's the first thing. So that means that when you start with founders, you really have to have an honest conversation about equity commitment. You need to put in place vesting arrangements so if people don't honor their commitments you can get their shares back, so you don't have shares on your cap table that are dead because the person's gone off to, you know, uh, surf someplace in Hawaii and you're left doing the work. So, so that's where you find the first culture explosion. If you get past that, the next place where you see it is, is going from three or four people who have a shared sense of culture and identity that's unspoken to the next five to 10 people. Because if you don't have a very clear understanding of why everybody's coming to work and what you're about, the culture fails. Because, yeah, and, and culture needs to be intentionally done. You need to tell people, "Look, if you're not interested in working eight hours, you know, uh, if you don't wanna work, you know, seven days a week, this isn't a place for you." Or if, if, if, if you're a person who wants to be able to see your family, I agree, that's what weekends are for. Or, you know, you need to be honest. Is this a, is this a, is, is the stock valuable? Is cash valuable? And, and get people who buy off on that. Um, and then once you get past that, that's when the ch- founder us- usually has the biggest challenge, because the skills necessary to bring people together that you know, and that next layer of people, you can manage them and communicate culture because you see them. But going from 15 to 20 to 50 to 100 requires institutionalization of culture, HR practices, compensation practices, mission statements, offsites, all the stuff that makes people understand why they're coming to work. Most entrepreneurs don't know how to do that Unless they've been a CEO before. And so that's where it's really important that they're self-aware, in my opinion. To take the advice, to say, "You know what? I need a chief operating officer who knows how to scale. I need a s- an HR person who knows how to scale. I need a CTO who knows how to scale." So when I say self-awareness, it's putting together the first team, getting the first group of people, have to be self-aware, be a good leader, but knowing when to let go and let other people help you scale. That's where most entrepreneurs have the hardest time, in my experience. Yes. Mm-hmm. Yeah. Yeah. Um, just before we get to our quick-fire questions, we, we often ask our guests, um, for some shortcuts or a cheat code- Mm of some sort. So you, you, in your vast experience, uh, Jonathan, what's something you wish someone had have told you earlier that would have made the difference that you can pass on to our listeners about entrepreneurship? So, um, I was a venture capital lawyer, I, I think I mentioned or I didn't, during the internet bubble. And I was, uh, involved in a lot of really good deals, very successful and great at it. And I decided I wanted to be a venture capitalist, own my own f- own my own firm. So I went out with a fellow who was one of, uh, the, uh, most important people in what was called America Online. And, uh, I had, was sitting there at lunch and he said to me, um, "Why do you wanna be an entrepreneur?" And I said, "Well, um, I wanna be rich." And he looked at me, he said, "That's the wrong answer." And I said, "Well, what do you mean?" He said, "No. You, you, you wanna be an entrepreneur because you love the journey." And I thought, "Okay, dude. Whatever. You know, you're a victory and an entrepreneur. It's easy for you to say whatever." And I went back home and didn't think any more about it. And then, um, about a month after that, I went out with, um, another good friend who's a very successful VC, and I- and he said to me, "Listen, you know when you're gonna be an entrepreneur?" I said, "When?" He said, "Because you're gonna be going home from work one day, and you're gonna look at the last email for the day, and you're gonna realize that you cannot possibly be more screwed than you are at that moment." He said, "Okay, you w- you with me?" I said, "Yeah." "Imagine that feeling." I said, "Okay." "Imagine you wake up the next morning feeling you're completely and utterly screwed, and the first email you see makes you realize the night before you were feeling optimistic." He said, he said, "If you feel in that moment that you are happy with the choice you made, then you're an entrepreneur." And, you know, it was really interesting because I, I kinda listened to him, but again, I was overcome with the excitement of being a VC, raising my fund. And I had a reversal during my fundraising about six months in where a big anchor commitment didn't come through. And it didn't come through, and it really disappointed me. And then, and a bunch of my other commitments went away because I lost my anchor. So I went from having a fund basically ready to close to not having a fund. And I thought to myself, "I cannot possibly be more screwed than I am right now." And then I woke in the morning and I said, "God darn it, I'm gonna show those people they were wrong." And it took me a year to raise the fund, but I raised it, and that's when I realized that, uh, it's not a shortcut as much as it is Until you've really f- failed, don't tell me you're an entrepreneur. Yeah. Yes. Wow. You know what I mean? And it's, and, and that's what I was talking about failing upwards. So that would be one cheat code. The other short cheat code would be, and I think I've revealed this, put somebody who you're thinking about going into business with into an uncomfortable situation and see how they perform. Yes. Mm. Find a way to do that. And, and until you've done that, don't trust them. You can like them, but don't trust them. Yeah. Wow. Yeah. Great advice. Yeah. All right. Mm. I think it might be quick-fire time. Quick, quick-fire questions. Oh, sorry. I'm, I'm shifting in my chair. Are you? Yeah. All right. Bring it on. All right. Let's, let's, let's get ourselves sorted. Everybody, everyone readjust. Yeah, yeah. All right, so, um, Jonathan, to get to know our, the person behind the microphone a little bit better, we ask each of our guests 10 quick-fire questions. So we'll fire you, them at you alternately, and we ask you to answer them in a sentence or less. So do you wanna go first, Colleen? Oh, I'm glad you gave me- I'll, I'll- Okay. It's a good thing you gave me that instruction, 'cause you, we've, it, I certainly haven't done that so far. Yeah. No. Okay. I'm ready. All right. You ready to go? Yep. Ready. All right. Let's go. Are you ready? Okay. Uh, office or work from home? Uh, both. Depends upon whether I'm working with other people, but I work here in my home office a lot. Mm-hmm. What was your first job? Huh. My first job was delivering, um, things for a pharmacy, and I didn't steal anything, I swear. We have that on record now- Yeah, yeah, yeah right? So... Yes, you do. I've... Exactly. I mean, it's, it's... Yeah. Exactly. What's your go-to productivity hack? Put it on some really good music. I have a really good stereo here in the office. It really helps me focus. Yeah. Are you an Android guy or an iPhone guy? Oh, I'm both, but I must admit I'm locked into iPhones as much as anything because I have 20 years of photos, so- Yeah I just- That's how they get us Yeah. I'm an iPhone guy. Yeah. Uh, what's your coffee order? Uh, generally a no-foam latte Mm-hmm. If you weren't doing what you're doing now, what career would you choose? I would've been a musician, 100%. And you know, 100%. I, I... You'd be seeing me right now in some, uh, sleazy bar playing Free Bird probably. Fun. Yeah, didn't see that coming at all actually. I feel like we wanted known that answer already. Yeah, didn't see that coming at all, right? Yeah. Yeah. Sorry. No, it's great. Um, what's the best investment you've ever made? Financially or, or personally? Um- Let's go personal my, my wife. Oh, good answer. Correct answer. I mean, honest to God. Correct. I wouldn't be w- So it's true. I mean, I, I, you know, I wouldn't be where I am without... Look, when I told her I wanted to start the venture fund, at the time I was a very financially successful partner at a major law firm. And I said, "You know, I wanna do this." And she said to me, "I don't care if you make a dollar. I'll live in a tent in Montana as long as you're happy." Aw. And she meant it. Oh, wow. Wow. So, but that's the best investment of my personal energy that I can imagine making. Um, investments, I don't know. I mean, uh, I think upside is, is where... I, I mean, like, like this is the biggest binary up and down thing. I mean, this is gonna be epic or it's not. But if it's epic, um, you can have me on the show and you can say, "So are you still a nice person?" We'll bring you back in like in a year's time. Yeah. So, so what's, so what's Money Junction done for you, Jonathan? Exactly. Yeah. Yes. Great. All right. Are you an early riser or a night owl? It depends upon how stressed I am. Uh, I generally am very good at going to sleep, but as I've shared with you earlier, I, I, I'm, uh... I get up early when I'm, when I'm anxious. Mm. Yeah. So. Yeah. So right now I'm, I'm an early riser. Yep. Yeah. Right. Startup fight, right? Yes. So, yeah. Exactly. Yeah. Such is the story. Yeah. Um- Yeah one piece of tech that you couldn't live without? At the moment, funnily enough, Claude. Yeah. Mm. There you go. See what I mean? I'm pro AI. Yeah. And Claude is- Claude's great Claude's terrific. Yeah. I mean, open it... I, I use it a lot. Yeah. Yeah. What's your book or podcast recommendation? I really like Cory Doctorow a lot. I mean, his most recent book, I just find that he is, to a fault, critical of so many of the things that we take for granted in the tech industry. I find reading him is always a really good palate cleanser, so I think Enshittification is, uh, is really worth reading. I love reading, reading history. I'm reading a book about, um, Sparta and Athens right now. Oh. By, uh... That's... I, I like history too. History... Look, you can't live in the United States right now and not read history, trust me. Yeah, see, I- You gotta read history right now. There's no problem with it. Oh, okay. And the final question before we close out the interview, if business truly is a game, Jonathan Aberman, what's your definition of winning? I think I talked about it earlier. I'd love to be in a situation which I'm driving to where I can make money for my family and my investors, uh, and put a technology forward that's going to make the human condition truly better. That's the mission I'm on right now. If we, if I accomplish that, that will be, uh... Honestly, that'll be the win of a lifetime. Yeah. Fabulous. Mm-hmm. Um, and where can our listeners find you and your business online? So the company's called Hupside, Human Hupside, and, uh, definitely go and website's there. As I said, you can play the game. The Hup Mapper should be there by the time your program, our program airs. It's there to be used. Figure out what kind of originality you have. Um, I'm on LinkedIn. You can find me, follow me there. Um, those are basically... I, I try to be very diligent about LinkedIn because, uh, I find that being consistent in one place is a good way for people who wanna follow you, so I don't spread it around, you know? Um, and so that's pretty much where you'll find me other than just- Asking AI what I'm up to. Google seems to do a pretty good job of stalking me. Yeah. There you go. Yeah. Oh, well, thank you so much, Jonathan. Yeah, thanks, Alison. This has been an incredible conversation. Yeah. I've learned so much, um, and I hope we can bring you back on the show, um, a few months down the line- Either way just, yeah, check in- Listen and see where you're at. Either way, we can do a check-in. Yeah. It'll either be, uh, you know, this time next year I'll, you know, I'll be living in a cave someplace and, you know, have spotty coverage, and I'll just be getting a digital hug, or you can say, "So Jonathan, are you still a nice person?" And we can talk about, you can run the tape back and- Yeah you know, we'll see. I look forward to that. I promise you I'll still be me. Yeah. I promise. I promise. Yeah, look forward to that, and I also like the uncertainty of it, right? This was fun. Yes, yes. And that's, that's the world we live in, so yeah. Absolutely, yes. Absolutely. Yeah. Thank you so much, Jonathan. No, this has been a lot of fun. Yeah. Yeah. Thank you. Oh, absolutely. Thanks for having me. It was just wonderful. Yeah. Oh, great. Yeah, appreciate it. All right. Well, that's all we've got time for. If you enjoyed this episode, make sure to subscribe to The Business Game, and check out the playlist for the level of business you're currently playing. Because every founder is somewhere on the game board, from zero all the way through to $200 billion. Choose your level, and we'll see you next time.