Meet Jonathan Aberman
Jonathan Aberman has spent more than three decades around startups, capital, and innovation from almost every angle.
He’s the co-founder and CEO of Hupside, an AI company focused on measuring “original intelligence.” Before starting Hupside, Jonathan worked as a venture capital lawyer, investment banker, investor, business school dean, and policy advisor on innovation at the federal and state level.
That gives him a rare 360-degree view of the startup ecosystem. He’s helped founders raise capital, evaluated companies as an investor, taught entrepreneurship, shaped innovation policy, and now sits in the founder seat himself.
As Jonathan said on Startup Success, “I’ve looked at innovation and entrepreneurship from just about every direction I think a human being can.”
That broad perspective makes his view of the current AI moment especially useful for founders. The market is noisy. Capital is concentrating. Investors are excited, skeptical, and cautious at the same time. AI tools are making it easier than ever to build, but harder than ever to stand out.
For founders, that means the real question isn’t simply “How do we use AI?”
The better question is: What can we build, know, understand, or create that AI alone cannot commoditize?
The AI Bubble Is Real, But So Is the Shift
Jonathan doesn’t sugarcoat the current moment. In his view, AI is in a bubble.
But that does not mean AI is a passing fad. The dot-com bubble didn’t end the internet. The social media bubble didn’t end social media. Bubbles can burn capital, inflate expectations, and create painful resets, while still leaving behind a major technological transformation.
AI is likely following a similar pattern.
The financial bubble is real because not every company attracting AI dollars will become a winner. Some startups will raise too much, too early, with too little defensibility. Some will build features that larger platforms quickly absorb. Some will discover that being “AI-powered” isn’t enough to create a durable business.
At the same time, the long-term adoption of AI isn’t going away. Jonathan compares the current moment to starting a company in the early 2000s without understanding the internet. A founder could do it, but ignoring the platform shift would limit the company’s ceiling.
The same is true now. Even companies that aren’t “AI companies” need to understand how AI will shape their markets, operations, customer expectations, and competitive dynamics.
If you’re building in SaaS, life sciences, fintech, consumer products, professional services, or almost any other category, AI will change the playing field. It may affect how you acquire customers, how you support them, how quickly competitors can copy you, and how investors evaluate your ability to scale.
The founder’s job is to see past the hype without missing the wave.
Thin AI Wrappers Are a Dangerous Place to Build
One of Jonathan’s strongest warnings echoes a theme we’ve heard from several recent Startup Success guests: founders building thin service layers over large language models need to be very clear about what makes their companies defensible.
In the early rush around generative AI, many companies were able to create useful products by wrapping workflows around models from OpenAI, Anthropic, Google, Meta, or other major players. Some of those products may become valuable businesses. But for many, the defensibility question is getting harder.
Large AI platforms aren’t staying neatly in one lane. They’re moving into workflows, enterprise use cases, agentic tools, partnerships, and vertical integration. As they expand, the major AI platforms are turning many once-promising startup wedges into built-in functionality.
That creates a serious strategic question for founders:
If a major AI platform can copy your product with a small engineering team, what protects your company?
If you don’t have a way to create something in the AI environment that the major platforms can’t easily take away, be careful.
That doesn’t mean every AI-enabled product is doomed. It means founders need to be honest about what they are really building. Is the company a feature, a workflow, a distribution wedge, a proprietary data asset, a network, a regulated solution, a trusted brand, or a deeply embedded system of record?
Investors are asking those questions, and founders should be asking them first.
“If you are trying to differentiate against these big guys, you better be very, very proprietary and special.”
~Jonathan Aberman
VC Is Powerful, But It Has a Specific Job
AI has made the fundraising environment more complicated. More capital is flowing into a smaller number of highly visible AI companies, while many other startups face a more selective market.
That can be frustrating for founders, especially those building strong companies outside the center of the AI frenzy. But Jonathan’s advice is grounding: fundraising shouldn’t be treated as an essential validation.
“The mistake a lot of entrepreneurs make is they confuse fundraising as a validation event rather than what it really is, which is just a step along the way.”
~Jonathan Aberman
A funding round is useful when it supports a business with real demand and a credible path to growth. It becomes dangerous when the company starts contorting itself to fit the capital source.
Venture capital is an excellent fit for some startups, especially those with the potential to grow quickly, dominate large markets, and generate venture-scale outcomes. For many Burkland clients, VC is the right path.
But it’s still a specific tool.
Jonathan’s view is that founders should begin with the business, then decide what capital the business actually needs. If there’s more demand than the company can serve with current resources, and if additional capital can accelerate growth in a large market, institutional funding may make sense.
If the company is earlier, narrower, more services-led, or less likely to produce a venture-scale outcome, other funding paths may be better. Angels, friends and family, state economic development funds, SBIR grants, customer revenue, SBA-backed loans, and product crowdfunding can all play a role.
Crowdfunding can be especially useful for product companies because it doubles as market validation. When customers prepay for something that doesn’t yet exist at scale, founders learn whether people want the product badly enough to put money behind it.
The key is capital fit. Good financing supports the strategy. Bad financing distorts it.
Investors Are Looking for Trust Before Upside
Founders often prepare for investor meetings by tightening the deck, polishing the TAM slide, refining the product demo, and memorizing traction metrics. All of that matters.
But Jonathan says something more basic happens first.
Investors are trying to decide whether they trust the founder.
Before they can get excited about upside, they need to get past fear. Fear of being misled. Fear of backing someone who can’t handle pressure. Fear of investing in a founder who’s charismatic but not self-aware.
That’s why over-polish can hurt. A slick pitch with no real connection can make investors uneasy, even if the slides look great.
“You over indexed on slick, and you under indexed on connection.”
~Jonathan Aberman
Jonathan says investors are often looking for self-awareness and coachability. Can the founder answer hard questions without becoming defensive? Can they acknowledge what they don’t know? Can they listen? Can they adapt without losing conviction?
This matters even more in AI, where the market is moving quickly and many founders are pitching into uncertainty. Investors know the technology will change. They know competitors will emerge. They know today’s advantage may not last.
So they’re evaluating the founder’s ability to learn.
The strongest founders don’t pretend every risk is solved. They show that they understand the risks and are capable of navigating them.
That kind of grounded confidence stands out in a market full of AI gloss.
AI Is Making Sameness Cheap
Jonathan’s deeper concern about AI isn’t that machines will replace every human contribution. It’s that generative AI makes competent-looking output incredibly easy to produce.
That has benefits. Founders can move faster. Teams can research, draft, prototype, summarize, analyze, and automate at a speed that would have seemed impossible a few years ago.
But there’s a downside.
When everyone has access to tools that can produce polished content, polished content stops being a strong signal.
Jonathan describes generative AI as a “sameness engine.” It can synthesize enormous amounts of existing information and produce smooth outputs. But because it’s trained on patterns, it often pulls toward the average. The result may be fluent, useful, and fast, but not necessarily original.
“We have access to information we never could have gotten as easily before. It’s tremendous, but the downside is they’re sameness engines.”
~Jonathan Aberman
That creates a new kind of competitive pressure for founders.
If your website copy, sales emails, product strategy, investor narrative, and customer experience all sound like they came from the same AI-assisted middle, you become harder to remember. You may look competent, but not distinct.
And in a crowded market, distinct matters.
Founders need to use AI without letting it flatten their thinking. The challenge is to pair AI’s efficiency with human taste, judgment, context, and originality.
AI can help you move faster. It can’t decide what your company should uniquely mean in the market.
Signal Collapse Is Changing How Founders Earn Credibility
One of Jonathan’s most important ideas is “signal collapse.”
In a pre-AI world, certain signals carried weight. A polished article suggested expertise. A sharp investor memo suggested thoughtful analysis. A well-written email suggested care. A beautiful deck suggested effort.
AI weakens those signals because it makes them easier to fake.
Now, a founder can produce a polished thought leadership post in seconds. A competitor can generate a credible-looking outbound campaign overnight. A job candidate can submit a clean writing sample that says very little about how they actually think.
That doesn’t make all AI-generated work bad. It means audiences are becoming more skeptical.
Investors, customers, employees, and partners are all asking the same quiet question: Is there a real human mind behind this?
Jonathan argues that this is where originality becomes valuable. In a world of abundant polish, people will look for signs of real insight, lived expertise, specific judgment, and genuine care.
“People are the differentiators in our society, not AI. People consume novelty, not AI.”
~Jonathan Aberman
For founders, this has practical implications.
Your investor pitch needs to show a specific understanding of the market. Your product needs to solve a real pain with depth. Your content needs to carry a point of view. Your customer experience needs to feel considered.
Signal collapse raises the bar for authenticity.
The founders who stand out will be the ones who can show the thinking behind the company.
Originality May Become the Next Major Startup Advantage
Jonathan believes the next phase of AI will place a premium on originality.
That doesn’t mean founders need to be eccentric or contrarian for effect. Originality means creating something that reflects distinct human intelligence: a novel insight, a better question, a sharper interpretation, a more useful product decision, a more resonant way to solve a customer problem.
Originality is what makes a company harder to reduce to a prompt.
In a market where AI can generate acceptable work instantly, acceptable work loses value. The premium moves toward work that feels specific, thoughtful, and new.
For startups, originality can show up in many places:
- A product wedge based on an overlooked customer pain
- A dataset competitors can’t easily access
- A workflow insight that only comes from deep domain expertise
- A brand voice that customers actually trust
- A hiring model that identifies adaptive thinkers
- A go-to-market motion that breaks category convention
- A founder narrative rooted in lived experience, not market buzz
This is where AI can become a paradox. It makes it easier to build, but harder to matter.
Founders who understand that paradox will build stronger companies.
Why Jonathan Built Hupside
Hupside grew directly out of Jonathan’s view of the AI market.
After investing in companies with real customers that were using AI to make their offerings stronger, Jonathan became increasingly focused on the human side of the equation. As machine learning became more capable, he began asking what humans would still do better, and how those capabilities could be identified, measured, and valued.
That led him to Hupside.
The company is built around the idea of “Human Upside,” which is also where the name comes from. Hupside’s technology is designed to identify originality compared to AI across different types of work.
Its first product, Hup Checker, includes the OIQ Challenge, a short self-test that helps people understand how likely they are to create something original in an AI environment. The company is also working toward tools that can evaluate content in real time, almost like a spell checker for originality.
The broader vision is to help people and organizations understand where human originality exists, how it shows up, and how it can create value in a post-AI economy.
Jonathan sees Hupside as a company positioned for what comes after the first wave of generative AI adoption. Once teams have access to powerful tools, the next question becomes: who can use those tools in a way that produces something genuinely valuable?
That is the space Hupside wants to measure.
What Founders Should Do Now
The AI bubble won’t resolve neatly. Some companies will soar. Some will disappear. Some will be acquired. Some will discover they were features, not companies. Meanwhile, AI itself will keep moving deeper into how businesses operate.
Founders can’t predict every twist. But they can build with sharper intent.
That means understanding where AI strengthens the business and where it creates exposure. It means knowing whether the company has a defensible edge or a temporary interface advantage. It means using AI to increase speed without sacrificing originality. It means communicating with investors in a way that builds trust rather than hiding behind hype.
Most of all, it means remembering that AI doesn’t remove the need for human insight. It raises the value of the best human insight.
The founders who win this next phase will be the ones who combine AI fluency with original thinking, market depth, customer empathy, and the discipline to build something that can’t be easily copied.
Thank you to Jonathan Aberman for joining Startup Success and sharing your perspective on AI, originality, fundraising, and what founders need to understand now.
To learn more about Jonathan and Hupside, visit Hupside.com. Jonathan also shares his thinking on LinkedIn.
Brenda Hernández Jaimes: Podcast Producer & Talent Coordinator, Ellas Media
Angela R. Chong: Audio Editor & Post-Production Producer, Amplify Podcasts
Speaker 1 00:00
Welcome to Startup Success, the podcast for startup founders and investors. Here you’ll find stories of success from others in the trenches as they work to scale some of the fastest growing startups in the world. Stories that will help you in your own journey. Startup Success starts now.
Kate 00:18
Welcome to Startup Success. In this episode, I sit down with Jonathan Aberman, co-founder and CEO of Hubside, and longtime investor and advisor to early-stage startups. We explore what makes a startup truly stand out to investors, the common mistakes founders make early on, and how the rise of AI is reshaping what it means to build a differentiated company. Jonathan also introduces the concept of original intelligence and shares how founders can use it as a competitive advantage in an increasingly AI driven world. Well, welcome Jonathan. Thanks for being here.
Jonathan Aberman 01:02
Absolutely, I’m glad to be here. Thank you for having me.
Kate 01:04
I’m looking forward to this. So, why don’t you walk us through your background a little bit? You’ve worked with so many different companies, and you know, been in all the different areas of the ecosystem. I think that would be interesting for listeners.
Jonathan Aberman 01:17
Well, I certainly have a 360 degree view of being involved in startups.
Kate 01:22
You do.
Jonathan Aberman 01:22
Yeah, I’m a founder now of an AI company. In my past life, I’ve been a venture capital lawyer. I’ve spent time as an investment banker. I’ve been a dean of a business school. I’ve helped to do policy making at the federal and state level around innovation. So, yeah, I would say over the last 30 years I’ve looked at innovation and entrepreneurship for just about every direction I think a human being can. And yeah, I certainly have a pretty informed perspective, and yet I keep doing it. So, what does that tell you?
Kate 01:49
That tells you something. And I want to get into your AI startup a little later in the show, because it’s super interesting. But let’s start with the basics. We have a lot of first time founders listening, and you know they just some advice on how to approach, you know, investors, how to talk about their story, what investors are looking for I think would be helpful.
Jonathan Aberman 02:13
Wow, there’s a lot in that we could spend the next hour. So let’s start, let’s start with the most important thing, which is that I think that the mistake a lot of entrepreneurs make is they confuse fundraising as a validation event rather than what it really is, which is just a step along the way. You know, I see this particularly when I look at how people treat venture capital. You know, the reality is that the significant majority, I mean, well, north of 95-99% of startups never raise $1 of outside capital, other than their friends and family, or, you know, their own bootstrapping. (Wow) Well, it’s true. I mean, if you look at the Inc 5000 list, for example, you’ll see that a lot of companies on that list never raise $1 of outside capital. I think when I used to teach entrepreneurship, the statistic that I used to use was the average amount of money raised in Inc 500, 5000 companies was roughly $50,000. So we have this tendency when we think about innovation to get really excited about the what I’ll call the single combat warrior view of entrepreneurship, which is, you know, the hero, the person who raises $100 million, $200 million billions of dollars, and has that spectacular exit, and that, that has the result of basically I would say, in some ways, perverting and changing the output of how most of us look at it. So, number one, venture capital is a very narrow financing tool that’s only suitable for a really small subset of startups, so if you start out thinking I’m going to raise venture capital, you already are putting yourself in a pathway where most of the time you’re not going to succeed. And nobody talks about that, because if you’re in the venture industry, as I have been, you want people to come to you and you want everybody to think you’re useful, so the whole industry, TechCrunch, and all the blogs are all designed to encourage you to think venture capital is the best way to go. So put that aside. (4:08)What do venture capitalists look for? Well, frankly, venture capitalists look for the same thing you should be looking for, which is, do I have a sustainable business that’s growing? And again, entrepreneurs who tend to think about this standpoint, Oh, I have to raise their venture capital, will say, Well, what do I have to have in the way of revenue to get a Series Seed? What do I have to have in the way of revenue to get a Series A? And you know, and they don’t understand that really the revenue number isn’t meaningful. What’s meaningful is, do you have more people who want to buy your stuff than you currently have the ability to deliver? Is there unaddressable demand? You know, is there a demand that can’t be funded with coming in the cash flow on your balance sheet, and if the answer to that is yes, then you’re a growing company, and then it’s a question of how fast. If you’re growing really, really fast and you have the potential to dominate a market that’s grow really fast, then you’re suitable for VC. So I think that there’s too much focus, frankly, on, Oh, I need to raise money to have a business, and instead it should be I need to have a business, and how to raise money to support that business.(5:08)
Kate 05:09
That is a great approach. I appreciate the fresh perspective on this show, because so many of the people on this show that come on are all about, you’re right, getting the VC investment, and that’s like the validation, right? What kind of round did you raise. And in this market, where it’s so tough, where so many dollars are just going to a few companies, what are some other ways then that entrepreneurs can do it besides VC funding?
Jonathan Aberman 05:36
Well, I think the first thing that I would encourage everybody to do when you’re thinking about starting a business, is understand why the money is pooling in the economy, and whether or not you have a way to play in that. You know, there are a lot of people right now who have raised a lot of money and are running to try to do quote AI companies.
Kate 05:56
Right.
Jonathan Aberman 05:56
(5:56)And the issue with a lot of AI companies is that fundamentally they’re at best a service layer over the large language models, at best.
Kate 06:04
Yes.
Jonathan Aberman 06:05
There’s nothing proprietary about them, other than they’re a service layer. And the biggest problem, the reason why you’re seeing this pooling of capital, is this the first time we’ve seen technology companies that are leading the trend actually trying to vertically integrate. You know, if you look at the internet bubble and social media bubble, these companies were quite happy to dominate a particular part of the ecosystem, you know, social media, advertising, but if you look at what Open AI, like as recently as what they did of last week or two and Anthropic, where they’re now partnering with banks and private equity firms, and you know, to push engineers to the edge the way they’re increasing capability, they’re really competing with most of the AI startups that have been formed the last couple years to take their business opportunity away from them as fast as they can. So the first thing to say is, (6:53)if you don’t have a way to create something within the AI environment that Open AI or Anthropic or Google or Meta can’t take away from you by getting some engineers, don’t. You know don’t, just don’t, because this is now a game that’s being played at the level of billions and billions of dollars. It’s winner take all to become the dominant monopolies in the AI trend. So, so let’s just start there. Doesn’t mean you shouldn’t do AI business, but if you want to do venture-backed business, the money understands that if you are trying to differentiate against these big guys, you better be very, very proprietary and special. (7:31)So you know, so that’s number one. Number two, (7:33)because a lot of the money is getting sucked into AI, it raises the question of what do you do as a startup, right? Yeah, the answer is that A) businesses and markets always cycle. We’re in the middle of a bubble, like the internet bubble, like the social media bubble. It’s a bubble, but you know, bubbles take time to work their way through, and it’s a financial bubble, because not everybody that’s investing is going to win, but the long-term trend is going to remain. So, if you’re starting a business and you don’t want to be an AI business, understand that the world you’re going to be operating is going to be heavily reliant on AI. It would be like starting a business in 2005 or 2003 and not having a plan to be a strong business that uses the internet and social media.(8:19) You follow me?
Kate 08:20
Good point. Yeah.
Jonathan Aberman 08:21
So, if you don’t, if you’re not, if you don’t have a plan for that, (8:26) if you’d have a plan for how to compete in the AI economy, your business is not going to grow big. In which case, it’s not going to be a business for investors, it’s going to be business maybe for you to do. So, for example, you could be a really, really great teacher of how people could use AI well. That’s that’s a skill a lot of us need. That’s a great consulting business. It could be a great business. It’s not a venture business. (8:44)
Kate 08:45
no.
Jonathan Aberman 08:46
Right now, so then you got the issue of, well, if I’m in life science, or you know, if I’m in plain old software, SaaS, I think that the answer is that markets are imperfect, but I’ve never in my life, literally, I’ve never in my life seen a business that didn’t have compelling growth characteristics, not find capital. So, it comes to me, it comes back to, to be blunt, if you don’t have people buying your product, you’d have people buying your service, it’s not a business that’s suitable for you to do, much less get money from outsiders, and that’s hard truth. A lot of people don’t want to hear that, because it’s like, you know, but you know this is one of the advantages of seeing it from 360.
Kate 09:29
Yes,
Jonathan Aberman 09:30
I’ve seen some really, really, really good friends of mine waste, you know, 123456, years or more of their lives pushing this, you know, this up uphill. And it’s their right as entrepreneurs to do that, but we should understand that at some point markets speak.
Kate 09:49
Yeah, yeah, you are speaking the hard truth. I like it, though. It’s great.
Jonathan Aberman 09:54
I’ll tell you a funny story. Well, I used to, when I used to teach, one of the things that I point out when I teach about corporate finance and entrepreneurship, is that the reason why VC money is so expensive, is because they have to get compensated for all the risks they’re taking. And I’ll draw a map through the capital markets line, I’ll say down here is government debt, private equity, VCs up here, you know, way up here, really, really risky. And I’ll say the only thing that’s more risky than that is, is the mafia lending you money, right? Like, what do you mean? They said, well, think about it, if you’re borrowing from the mafia, you clearly, you’re a risk, right? And, and so, so inevitably a student will say to me, well, you suggested that the VCs are like the mob, and I’ll say, now you understand, now you’re getting the point. No, I don’t mean the mob. I’m a VC. I mean look, I’ve been a veteran of the business for 25 years, but understand, the money is really expensive for reasons.
Kate 10:49
Right. It comes with a lot of costs, I think.
Jonathan Aberman 10:53
Yeah. So, so I mean, we’ll talk, I will now talk if you want about some of the ways you can raise money, but I thought it was really helpful for your listeners just to have some loving, you know, honest observations about if you’re not raising money, it doesn’t make you bad, and why it’s hard to raise money.
Kate 11:10
No, I think that was really helpful. Yeah, I mean, any other, you know, the ways you can share besides VC money, I think would be helpful.
Jonathan Aberman 11:20
Well, (11:20)I think that at the end of the day, raising money from people that know us is the place to begin, because they’re the ones that are going to be able to look at it from the standpoint of not a financial investment necessarily, but from one an investment based upon some level of trust and then some level of willingness to share the entrepreneur’s view of risk. So frankly, the reason why friends and family and angels can be better financially for you is because they invest their own money, and so the psychological connection they can have with you, the trusting of you, will make a difference. It’s not surprising that most people raise money from people they know or angels that they’ve met, because it’s their money, so they can take a chance.(12:01) You know, many states have financial incentives, they have venture funds where they invest in promising companies to do economic development. Most states do these days. Again, they’re not really risk-based investors, then we’re interested in growing companies to put people to work. So if you’re in a state like Virginia or Maryland or Pennsylvania, and many others, they’re state venture capital and business assistance organizations that provide $50-$100,000 to start businesses if they look promising. The federal government has a plan, a program called the Small Business Innovation Innovative Research Program, which you may have heard about SBIR, you know, that pumps a couple billion dollars a year into startups to develop technology that could be of interest to the federal government, and that has other advantages as well. So, for me, the way the tiering works is (12:49) you always start a business on the on your own back, you know, you, if you’re not willing to take the risk, if you’re not willing to take some financial risk, and I don’t mean mortgaging your house, I mean just like working nights and weekends, or going without salary, but unless you’re willing to take the risk, nobody else should take the risk.
Kate 13:04
Well said. Yep.
Jonathan Aberman 13:06
You know, just it’s a fact. And, but once you’ve sort of signaled that, then if you need additional money, and you’ve sort of maxed out your charge cards and done the obvious things, then it’s friends, it’s family, it’s state and local economic development, it’s federal funding. Those are the general ways that people sort of bootstrap to their first customers or customers, right. And then it’s a question of whether you’re going to finance through customers, you know, we would like actually grow your business by selling stuff, or whether you get to the point where it looks like it can scale rapidly enough that you can go to strangers who won’t invest in you because they like you, but will invest in you because you help them make money(13:45) , i.e. angels you don’t know, professional investors, or you might get to a point where you have enough predictable cash you can borrow from a bank. You know, I mean, a lot of people grow businesses, family businesses, and make a lot of money and support the families really well by doing SBA guaranteed bank loans.(14:02)
Kate 14:03
Yes.
Jonathan Aberman 14:04
You know
Kate 14:04
It’s true.
Jonathan Aberman 14:05
So, so to me, the way it looks is every business I’ve ever seen starts the same way, the founder sees a problem they want to solve, or a group of founders see a problem they want to solve, they then get enough money or sweat equity together to get to a prototype or get to initial service offering, right. Get in the market. How do people react? If you need some money to start to do the other things you need to do, then you’re credible. You borrow money from your uncle, you know? Maybe you meet somebody at school, maybe you go on AngelList. I don’t know, but you know, you raise some money. Oh, the other thing I forgot, because I’m so old school, is don’t forget crowdfunding, particularly, particularly when you’re crowdfunding a product. You know, I really, I really, really think that going and using the crowdsourcing, not for equity, I don’t like that as much, because then you’re dealing with individual investors that aren’t very wealthy, and that can really mess up your long-term capital structure. But getting people to prepay your product, you know. What better product market discovery is there on the map. Give me 1000, 2000 or 5000 people to say, “You know what, if you deliver that, I’ll buy it.”
Kate 15:10
Right.
Jonathan Aberman 15:11
And they actually give you the money ahead of time, so you basically finance the construction of their product, with their order. That’s a phenomenal way to start a product company. I completely forgot about that.
Kate 15:21
That’s a good call out. They also can give you good feedback, right, on tweaks to your product and whatnot.
Jonathan Aberman 15:28
Yeah, absolutely. Now, just to go complete the cycle, what do people look for? Not what do investors look for, what do people look for? It’s a little known fact, I think, that most people actually, before they get greedy, actually have to get over their fear of being embarrassed. And nobody will give you money unless they’re convinced you’re not a criminal. Nobody will give you money unless they’re convinced you’re trustworthy, and so you have to get over the fear of embarrassment, of the fear of being lied to, before people can get greedy. And I don’t think entrepreneurs really understand that. So, they go into a meeting, and they’re all flashy and all excited, you can’t lose, and they come across really sleazy and slick. And then there’s no trust that’s developed, and “I don’t understand, the meeting went great. Why did nothing happen?” The answer is because you over indexed on slick, and you’re under indexed on connection.
Kate 16:17
Yeah.
Jonathan Aberman 16:17
You know, the best way to describe it is (16:19)psychologists have pointed out, and most venture investors know this, that anybody who’s an entrepreneur is in some ways crazy. It’s, but we are, I mean, we are. Think about it. We wake up and we’re like, Oh, I’ve got an idea, I’m going to do x. It’s not like everybody sitting around saying, Oh, Jonathan, please, I hope you started a company. My life was empty before. Everybody’s getting along just fine.
Kate 16:41
Yes,
Jonathan Aberman 16:42
but yet, but you wake up and say, I’m going to do something that’s going to make people change their behavior. That is, in some ways, shaking your fist to status quo. We would define that some ways as crazy, not crazy in a and insane way, but crazy, like, how dare you be that, right? But the difference is, everybody’s got to be crazy enough to be an entrepreneur, but some people are truly pathologically mentally unstable. They’re narcissistic, they’re sociopathic, they’re manic, and unfortunately, or fortunately, entrepreneurship draws people with those type of pathologies to them.(17:14)
Kate 17:15
That is so true,
Jonathan Aberman 17:17
Right? So, believe it or not, when I, when I’m an investor, the number one thing I want to get a handle on quickly is whether I deal with somebody who’s crazy enough to be an entrepreneur or somebody that doesn’t have mental stability. And so what I look for is I look for self-awareness, because generally, and again, this is backed up by science, if people are self-aware, they are able to manage their demons, they are unlikely to have a pathology that’s consuming them, like you could talk with a narcissist all day long about your feelings, and they will look at you like you’re insane, because they’re not self-aware. So, if you get the sense that somebody wants to take you for dinner, or wants to take you for coffee, or ask you some really hard questions to see how you react, whether they will acknowledge it or not, what they’re really trying to figure out, is are you coachable and self-aware, and are they able to connect with you. And there are a million ways to do that. Great slides, great cover letter, showing up for meetings on time, but if you imagine, if you imagine raising money is like dating, it can’t think of anything else, just think about dating. How do you get somebody to actually like you? You listen, you, you are, you’re open, you don’t try too hard, you’re friendly, you don’t, you’re not clingy and creepy. I mean, all these things, right? Dating really, if you can’t think of anything else, think about how you handle yourself in the world where you’re trying to make friends, and use those skills to get people to give you money, because then you’ll be authentic, and you’re much more likely to succeed.(18:43)
Kate 18:45
So true. As you were describing talking it through, we are all.. I was thinking of so many founders I know that don’t have that self-awareness, right? And that’s one of their downfalls: they can’t take the feedback, they end up fighting with investors, they don’t get along with their founding team. We’ve all seen that story.
Jonathan Aberman 19:03
Well, I think that what’s interesting is, again, remember, if you know the industry indexes, and people can come in and – look at Steve Jobs. I wouldn’t say that Steve Jobs was the most, from what I’ve heard, from friends who worked with them by far, he was not a very empathetic person with standpoint of people skills, but what he had was tremendous empathy of understanding what customers wanted from a product. And as a result, he, the biggest difference between Steve Jobs when he got thrown out of Apple and Steve Jobs when he came back, is either he realized or the people around him realized that he needed to be surrounded with people who, when he was abusive, would say it’s just Steve, and they go back to work. And that’s why he was so successful the second time around, and he was a genius. The industry will be tolerant, we know, I’m sure you do too. Some really successful entrepreneurs who are narcissistic, sociopathic, and manic. It happens because life is also about luck, and sometimes, frankly, people are so talented, they could overcome the negativity associated with with their faults.
Kate 20:05
Right.
Jonathan Aberman 20:06
You know, but if we’re giving advice to your listeners, if we’re giving advice to people in an academic setting or at an event, you know, I tend to give bell curve advice. You know, there’s always gonna be an outlier, you know. Outliers can succeed, but if you’re asking my advice as the mentor, the middle of the envelope advice is you’re much more likely to succeed if you’re self-aware, coachable, and connect with people.
Kate 20:30
Yes, agree, agree, that’s so spot on. So, let’s talk about this market, how you’re feeling about this AI world, because you’ve seen a lot of these bubbles, like you talked about. And then I want to get into where Hupside fits into it.
Jonathan Aberman 20:45
Well, it’s interesting, is Hubside, and why I’m doing it, very much relates to my view of the market, because I’ve been around software for a long time. And I’ve been watching the development of machine learning, which is really what’s happened for a long time. And I’d been more and more concerned about the issue of humans, and what humans are going to do as machine learning got more and more competent. That’s why I took time out from being an investor to be a dean of a business school. We merged the computer science and the business and the art and design schools into a single college, because I wanted my students to be exposed to creativity and, and problem solving in a holistic way, right. So, when I left there, and I went back to investing, most of the investments I was making at Ruxton Ventures were not large language models, they were businesses that had customers that were using AI to make their offerings better. We called them small language models. And it was a very, it’s a very good portfolio. The companies grow very nicely. They’ve, for the most part, raised downstream capital because they have customers. And so my view of the market is very much shaped by that experience. (21:48)I look at what’s going on now with the rapid commercialization of Gen AI models, and what we’re seeing is that they have unbelievable benefits, which is they allow us to stand on the shoulders of giants. We have access to information we never could have gotten as easily before. It’s tremendous, but the downside is they’re sameness engines. They create commoditized information and experiences, and as they leak more and more into the economy, what’s happening is they are capturing efficiency gains for themselves, because ultimately you know you become more and more reliant on gen AI tools, you’re going to pay tokens. So they’re knitting themselves into the economy and making AI an integral part of the economy overall, which is why you’re seeing all the investment and the stock market boom. The implications are that at some point the tendency for monopolization, which is natural. (right) The issue is, are they going to take so much value out of the economy, you know, that’s there’s nothing left for other people to do. Or there’s not enough for people to do to add value, that the economy literally suffers, and it collapses under its own weight. That’s that’s the, that’s the big million dollar question, billion dollar question. (23:05)So, when I look at the, that look at AI, I look at it from a standpoint of the number one thing that nobody’s talking about right now is signal collapse. And what I mean by that is, we, and you can feel it, you know what I mean, it’s this feeling that Wait a minute, I used to be really respected for my education, or I used to be really respected for my content, I used to be really respected for what I did. How do I signal my competence to the world where AI is hyper, hyper smooth and appears polished? (23:32)Or I just got another fricking LinkedIn post, what a load of crap. This was written by AI. How do I separate what’s, you know, so it’s signal collapse. (right) We’re struggling with what’s true, what’s real. And, and I think that the same way that the internet bubble had its leg and came down, and then the next leg was social. I think that what’s going to happen is this desire for commoditization, for effectiveness is overdone. And as this ends, the next thing is going to happen is people are going to say, “Wait a minute, AI is great, but there are things AI can’t do well.” You know, people are the differentiators in our society, not AI. People consume novelty, not AI. For people, and by the way, there are a lot of jobs that AI software can’t really do. So, so I think there’s going to be a much greater premium on what, what I call, and my partners call originality. (24:27)
Kate 24:30
Yes!
Jonathan Aberman 24:30
Right. And so we think the next big leg is going to be all right, we have the tools, how do we create value add in a post AI economy? And I think that’s the next biggest wave, and I, and I think it will not just be a software wave, I think it’s also gonna be a way for creativity, creative performance, artists, great plumbers, really good teachers, I could go on and on. Point is that there’s gonna be much greater understanding that humans, and what humans can do, is actually going to be worth a lot. And so that’s how I view the world. And I’ve always been a futurist. I always look five years ahead. That’s why I like the venture industry. And that’s where I see it going, which brings me to Hupside. So, why did you Hupside? Well, if you understand that’s my worldview, and I’m making investments. Well, I found a group of scientists that had invented the world’s first engine to be able to identify originality compared to AI in any task. And literally in anything, it could be a piece of news, it could be an article, it could be anything. And so we’ve been working for the last less than a year to start to commercialize products so that people can see what’s original, so our first product’s the Hub Checker. And Hub Checker, and by the way, anybody who’s interested in this, you go to the website Hupside.com You can find out your own originality competency by taking the OIQ Challenge. It takes five minutes. What it does is allows you to see how likely you are in an AI environment to create something original. How does your brain work? So that’s product one, that’s Hub Checker. What we’re working on now, and we’re going towards is the ability to take a piece of content and be able to look at it in real time, almost like a spell checker, and say Yeah, there’s originality in this, there’s something here you couldn’t get out of AI. And you know, we think that if we have those two products available in the market, we’re now in a position for the next trend, which is the trend of originality. We’re in a position to basically be the umpires for a new kind of game.
Kate 26:31
Yeah, I think you’re 100% correct. Like, we’re seeing it now. In the beginning, it was all just generate AI blogs, case studies, all this stuff. Now it’s swinging back. Get the human touch in there, make it a little more original. Take the AI content, and then have a human rewrite it. It’s already starting to swing, so you’re, I think you’re absolutely right. And it’s just going to get more so as more AI slop, as they call it, is out there.
Jonathan Aberman 27:00
Well, it’s interesting, you know, again, talking with my friends that are, that are professionally psych, you know, or psychiatrists, or people who understand clinically human behavior, you know, they’re really only – they’re only two primary drivers for all of us, our behavior. One is the desire for safety, and the other is the desire to matter. Seeking novelty. You know, see what makes me special. What makes you special? What do we exchange that makes us attach? It’s something special. I worked for a Japanese company as a first job, and if you could imagine being a middle-class kid from Philadelphia, suddenly in London, all my colleagues were Japanese, and so I learned a lot about a lot of subtle things. And my boss one day took me out for lunch, and he said to me, said Abermann, son, I need you to understand the secret to success in this world. And I, I said, okay, Mr. Nakamy what is it? And he said to me, it’s kindness. And I thought to myself, huh, I, that wasn’t what I expected. I mean, there was nothing about working in a hierarchical Japanese company was kind at all, so I said, and he said no, no, no, and he said, you’re stupid, because he loved me. He said let me understand, let me explain, he said kindness is is giving me a memo without typos in it, or me giving you a bonsai tree as a gift, or you’re seeing a really cute Mickey dog, he said, How does it make you feel, and I said, Well, in each case it makes me feel like it’s special to me, and I feel respect, and I feel like somebody spent some time preparing it. And he said exactly. That’s what makes society go, is when we are kind. And I realized what he was really getting at is what we would now call novelty.
Kate 28:38
Yes.
Jonathan Aberman 28:39
So that’s why we react so badly to word slop. It’s like, why am I reading this? You didn’t even write it.
Kate 28:45
Right. Exactly
Jonathan Aberman 28:47
Right?
Kate 28:47
Yeah. No, no, you’re really, you’re really on to something. I’m actually happy to hear that, because that’s, you know, something we’re all a little worried about. We’re actually at time. I can’t believe it. I really enjoyed this conversation a lot
Jonathan Aberman 29:00
Me too.
Kate 29:01
I can tell you must have been an excellent professor. You have a good way of explaining things.
Jonathan Aberman 29:03
Oh thank you.
Kate 29:05
Where can listeners go to learn more about Hubside?
Jonathan Aberman 29:08
Yeah, so it’s Human Upside, Hupside.com Human Upside.
Kate 29:13
Human Upside. So that’s where the name comes from? Hubside. I like that. Okay.
Jonathan Aberman 29:18
Yeah. Well, the good thing is I have a great marketing company called REQ and you know, I – I had a different name, and they said no, no, no, you’re gonna name the company this, and it’s working out. (I like that.) So, Hupside.com there’s lots of information. We’ve, we’ve made available free versions of the self test, and also there’s a version of the product called Hub Checker, where you can shake it and use it as a way to learn about 10 of your friends or 10 coworkers and learn about how they approach problem solving. It’s really, really cool, and it’s AI proof, but that’s the thing, you can’t cheat it.
Kate 29:52
That’s great.
Jonathan Aberman 29:53
Really, really cool. And then I’m on LinkedIn, you can find me there. That’s the place where. I tend to do my most social. I’ll probably launch a Substack soon, but right now, anything I’m thinking about is on LinkedIn.
Kate 30:03
Awesome, I really enjoyed this. Please come back in a year or two, get an update.
Jonathan Aberman 30:08
Anytime. All right, well, I will. Thanks for letting me share with your audience. It’s always a pleasure.
Kate 30:13
Thank you.
Outro 30:15
You’ve been listening to Startup Success. To make sure you don’t miss out on future episodes, subscribe to the show in your favorite podcast player. Like what you hear? Tap the number of stars you think the show deserves in Apple Podcasts. For more tools and resources for your own startup success, check out burklandassociates.com. Thank you so much for listening. Until next time.