Omar Haroun: “Outsized Impact is Incredibly Rewarding”
Episode - 60
Omar Haroun: “Outsized Impact is Incredibly Rewarding”
In this conversation, serial entrepreneur and exited founder Omar Haroun reveals the hidden emotional cost of success, the identity collapse many founders experience post-exit, and why wealth alone often fails to deliver fulfillment.
Omar Haroun is a multi-exit entrepreneur and investor who has spent years studying the psychological and emotional realities of life after selling a business.
He reflects on the philosophy of life after success:
how wealth gives safety but not security, why progress is really about trading old questions for better ones, and how many people quietly waste their freedom by staying comfortable.
We explore:
• The moral responsibility that comes with capability
• Why regret is a better compass than ambition
• How founders get stuck using old success models in a new life
• Why contribution, not accumulation, becomes the real measure
What We Discussed:
00:00 – Introduction & serendipitous first meeting
03:07 – Selling an AI company before AI was mainstream
05:00 – Convincing major corporations to trust AI
06:07 – Vision: making legal services accessible through AI
07:26 – Post-exit emptiness: when money isn’t enough
09:31 – Why mission matters after exit
10:20 – Childhood, ambition, and the drive to make money
12:55 – Achieving the exit—and feeling empty
14:10 – Aristotle and redefining success
16:33 – Founder motivation beyond money
18:41 – Healing and integrating the old self
20:14 – Health, relationships, and family repair
21:52 – Family trade-offs and starting again
23:01 – Regret minimization as a life framework
24:52 – Structuring life around children
27:52 – Using AI to multiply personal productivity
30:54 – Building a personal AI operating system
32:49 – Why philosophy helps founders post-exit
37:05 – Living with contradiction and moral trade-offs
39:05 – Learning philosophy in the AI age
42:50 – Intuition, spirituality, and big decisions
45:31 – Creating markets, not just products
48:54 – Duty, talent, and responsibility after success
51:29 – Why permanent leisure fails
53:59 – Mission, Maslow, and self-transcendence
56:27 – Modeling purpose for children
57:26 – The meaning behind “Eudia”
58:44 – How Omar wants to be remembered
59:10 – Closing reflections & farewell
-
Anastasia Koroleva:
[00:00:01 - 00:00:09]
Hi Omar, thank you so much for joining me today. I am really, really excited about this conversation. As you know, a lot to dig into.
Omar:
[00:00:10 - 00:00:11]
Excited to be here.
Anastasia Koroleva:
[00:00:11 - 00:01:02]
Do you remember our first meeting, how we were at this event and we ended up in one kayak together, just you and me. And I remember like literally minutes into the trip, you started telling me about this amazing AI company you had just sold in the legal space. And I was just sitting there thinking, oh my God, here I am, someone completely obsessed about the whole post exit journey. A former M and A attorney and a tech founder in this boat with you of all people. So I thought it was a sign from gods and I really think it was because since then you've been such an inspiration and source of wisdom and I'm just really grateful for that moment that brought us together.
Omar:
[00:01:03 - 00:01:07]
Yeah, I'm a big believer in serendipity. Definitely felt like that.
Anastasia Koroleva:
[00:01:07 - 00:01:28]
Exactly. Me too. Exactly. So one of the things that I found super impressive about our conversation back then is the fact that you had already sold an AI company and a massive and complicated one before it was even a thing. Can we start with that? Tell me more about it.
Omar:
[00:01:30 - 00:03:00]
Yeah. So I never really, I think on the one hand what lawyers do is really analyze language and generate language. And so language models have obviously been around for a while and I think it felt like a very good fit with what they could do. At the same time, lawyers are very risk averse people and law firms bill by the hour. So even if there is technology that can significantly reduce the hours, law firms in particular never really from first principles, felt like they were kind of the right customer. So we actually were one of the first companies, my last company, and even this one, to sell to the general counsel and the in house legal team who has the same incentives. And ultimately my last company was very much reducing risk, not even focusing on efficiency by using AI to find very sensitive communications in the context of litigation, typically. So if a company's going through a lawsuit, they're often required to hand over millions of emails and documents and our AI would in like five minutes discover that the CEO is having an affair or something was going on that they really wanted to know about and that was at risk, risk of being missed before it went into the public record. And so it was a pure risk reduction play. But for a risk averse buyer, once they saw what it could do, they had to have it. And then we kind of had a good exit in 2021.
Anastasia Koroleva:
[00:03:00 - 00:03:17]
How did you manage to persuade some of the largest companies in the world to actually trustyou with their data. Because for me that's just mind blowing. Especially given my background in law and knowing how risk averse and protective of data lawyers are and have to be.
Omar:
[00:03:17 - 00:04:06]
Yeah, definitely. I think a lot of it is. I mean, obviously from a privacy security standpoint, there's a lot you have to do, which is at the extreme end of what most startups would never do. But even after that, I actually firmly believe that trust is actually a human to humanexperience. And part of why with that company and even this one, I'm living on a plane and traveling so much, is you really just need to build that trust. Once you have obviously broken through and you have a set of customers who have now seen that using this technology was obviously not only safe and secure, but actually a career enhancing move for the individuals who brought it in, then it starts to shift from being risky to being an opportunity. But you're absolutely right, the bars probably couldn't be higher than it is legal.
Anastasia Koroleva:
[00:04:07 - 00:05:24]
Exactly. Because today many more companies appreciate the need for AI. But back then also it's really impressive that you managed to persuade clients to trust you. And then of course on that amazing kayak trip, before it was over, you invited me to come and stay at your family house with my husband, which I later did. And then we had another mind blowingconversation when you shared your vision for the future with me. And you were saying it's great to enjoy life, to enjoy my family, but I really have this vision and I have to go after it. And the vision that you described to me at the time was that you wanted legal services to be accessible for everyone and AI would help. And there was so much passion and spark in your eyes and so much conviction and I was like, oh my God, it's actually happening. He is going to do that. So can you take me through that moment when you just had this brilliant idea to what is happening today and how you ideated how you had that certainty? Because it's really impressive where you are at the moment.
Omar:
[00:05:26 - 00:07:31]
Thank you. Yeah, so after selling my last company, I and I think we'll probably talk a lot more about this, but I went through what I was very surprised by, but you're obviously creating a podcast to show it's not that uncommon, but this very, very sort of unusual experience where I felt the exact opposite that I expected to feel and then that set me off on this journey and as I was reflecting, I think a big part of it was even though we had had a good financial outcome, we didn't really do anything to actually change the legal industry. And legal, I would argue, is competing with healthcare for maybe the one industry where these very, very complex and perverse economic incentives and this whole ecosystem that's really built on top of these incentives being in the wrong way are actually preventingconsumers from. I mean, 90% of people who need a lawyer can't afford one. Most Americans are a single legal event away from bankruptcy. And then you look at businesses and companies, like even my current company, I think we spent $75,000 on our series A legal documents. Right. And anyone who's in the AI world knows that actually most of this work you can. Now, whether you can automate 80% of it, 60% of it, I mean, we could debate what the percentage is, but it's very, very high. And so the technology's there. We proved that with my last company, even before ChatGPT. Now it's obviously even more accessible than it ever was. And yet there's almost no adoption of actual AI. And so, yeah, when I really reflected, and we can get a lot more into the details behind that, but it felt like whatever I did next, I really wanted it to be something that had a deep mission attached to it and where it wasn't just about building a business, it was actually about changing a whole industry and really leaving that kind of legacy on the world, which was very, very motivating.
Anastasia Koroleva:
[00:07:31 - 00:08:16]
Yeah. And that's exactly what I saw back then in you. You were literally lit up with energy and conviction. But I do want to go deep into that, because I think this is actually the most challenging thing in the post taxi journey is to find that next thing that actually pulls you, that that is a mission. And I'm very, very saddened by the fact that so many people don't, you know, they give up and they settle for something that's comfortable. I'd love you to share a little bit, like why you didn't settle, why you kept looking for it, and maybe when this idea popped into your head, and most importantly, you know, if you were financially set, like, why bother?
Omar:
[00:08:17 - 00:08:17]
Yeah.
Anastasia Koroleva:
[00:08:17 - 00:08:19]
Why mission was so important for you?
Omar:
[00:08:20 - 00:14:33]
Yeah, maybe I'll start with that last one and then kind of work backwards. So I think for me, it's funny, from the time I was a kid, I had parents who were immigrants. They worked extremely hard. They were basically living paycheck to paycheck to be able to put me in the school that I went to. And I'm very grateful. It was a very good school. Uh, but it was a school where every Other kid was wealthy pretty much because it was a really expensiveschool. And so even though we weren't like poor or anything, you know, a lot of the research in economics has shown that happiness is all on a relative basis. So people tend to compare themselves to whoever they're around. So if, if you're in a $1 million home, but everyone around you has a $10 million home, you feel poor. Whereas if you're in a $1 million home and everyone around you has $100,000 home, you feel. I was definitely always felt very kind of left out because everyone that was around me was going on these fancy vacations and their parents all knew each other and my parents were these immigrants who were working all the time. And so it really actually made me quite motivated to actually just make a lot of money. And that became my goal. If I'm being totally honest, I also happen to be relatively entrepreneurial and when I looked around I just saw the people who had really life changing kind of money were basically founders. Obviously the risk is much higher, but I've never been risk averse and so decided to basically go for it and set a goal that I wanted to be able to retire by the time I was 35. And this is kind of in high school. And then long story short, went through a lot of twists and turns, but ultimately, after a lot of years of pain and suffering, I would say ended up with this at the age of 35, suddenly getting this nine figure cash opportunity to sell the company and took it. And then I felt very, very again super empty, like the day that the transaction closed. And that really then set me off on this journey of self reflection, I would say. And probably when I met you in the kayak, I was towards the end of it, but. But you know, I think a lot of it was I really started by just questioning why don't Ifeel better than I actually feel, given that I've on paper achieved what I wanted to achieve. And for me, I think a lot of it was first of all confronting some of the realities that by working eighty hundred hour week, you know, for years, I was able to kind of ignore many things in my life and in particular I would say my relationships, my health, I mean a lot of things were actually suffering, but because I was so distracted and motivated and focused 100% on the startup and achieving that, that outcome, I just sort of now suddenly didn't have that excuse and had to realize I've actually not been doing a great job in every other part of my life. And so that was one part of it, but I think the deeper part was it took me a long time to really recognize that even though at one point it was probably about the money, it really wasn't about the money. And specifically the book that I reread was the Nicomachean Ethics by Aristotle. I had studied philosophy actually as a undergrad and remember even back then having this moment where that book and those ideas really resonated with me. But I went back to it and really reread it. And the punchline is that Aristotle, I mean, the opening chapter is basically arguing that all people want the same thing, which is to achieve a good life, happiness, what he calls eudaimonia, which is actually beyond even happiness, really sort of this feeling of deep satisfaction with your life, that when you're at the end of your life and you look back, you want to feel like it was a good life. However, most of us are wrong about how to achieve that. So some people believe that it's money, some people believe that it's power and they go into politics. Right? We all have different ideas, but basically he gives kind of the recipe. And essentially the, the one minute version of it is if you achieve your potential and live with integrity, those are the two things, then you will achieve this state called eudaimonia. And so I really thought a lot about, well, have I achieved my potential? I was 35 and I had this exit. I still have a huge part of my life ahead of me and I've learned a lot about not only startups, but also deeply understanding the legal industry, which I almost think you have to have 10 years of experience in it to be able to even be eligible to change it, because it is very complex. And so it just started to feel like that was a big draw. And then my, my biggest learning from doing startups for 15 years and investing in dozens of startups and being around founders and seeing very, very talented people and technologies fail. And the reverse is that I think market timing is probably the most important factor in your success and the one that's the least in your control. And so here I was kind of in this kayak with you, and then after ChatGPT, suddenly the market's ready and I did 80 interviews with general counsel just to confirm this. And I actually really kind of wanted to understand with very open ended questions, not even telling them about any ideas that I had. But it was the first time I saw that 90% of the people I talked to were making transformation by AI a top three priority. But they hadn't found anyone that they actually did trust or any technology company that they could trust. And so that was when it really clicked and I just felt like, okay, I should really go for this.
Anastasia Koroleva:
[00:14:33 - 00:15:30]
Omar, you said something really important. I don't want to miss it. You said that even though you thought you were driven only by money, now you know it's not the case. And I think I know exactly what you're talking about because I see it all the time. These amazingly successful exited founders honestly thinking that the motivation that pushed them to start the company in the first place was still the motivation by the time they sell. But I found that it actually is never the case because if unless that motivation changed into something higher, like really the desire to serve employees, to serve customers, to contribute, a company does not reach that nine digit, all cash exit, you just cannot create value out of that old motivation. That motivation is perfectly fine to start, but we have to evolve. Would you say that that's also what you realized looking back?
Omar:
[00:15:31 - 00:16:05]
Yeah, I mean, I think on some level startups are really interesting because whatever motivation you had in the beginning, I think at some point you, if you're a very resilient person and it just becomes a challenge that you have to solve, I think that ends up becoming to me a big part of the motivation as well. Right. So even, even if in the beginning you have time and the luxury of time to think about all these things. I think like even now I'm, I'm back in the thick of it and I literally have no idea what's going on in the world anymore.
Anastasia Koroleva:
[00:16:06 - 00:16:10]
I know, I noticed. Took me months to persuade you to come to this interview.
Omar:
[00:16:14 - 00:16:41]
So I think you're right. I mean, I think if I was thinking rationally about how to make the most money on a risk adjusted basis, I never would have even done the last startup right. Even maybe a few years into it. So I think you're right. I think even back then it wasn't about the money. But I don't think, I think most people almost need that time after the exit or when they have the luxury of time to really even deeply sort of examine and reflect and be intentional.
Anastasia Koroleva:
[00:16:41 - 00:18:14]
And I think it's actually very healing because a lot of self doubt, which is a very common thing post exit, comes from the fact that we honestly believe that we were driven by something that's wrong. You know, we have friends who believe that they needed to kind of kill the old self for the new self to be reborn. And I really don't like this because this comes from disrespect and hatred almost for the old self, which in case of people who created disproportionate value, is just never the case. And going back and appreciating how much we've grown through the startup experience is really where we need to start before we even consider killing ourselves and being reborn into a more beautiful person. Because we are already beautiful people and there is so much else to give. Right? I think it's wonderful that you're saying because you felt it sounds like you were ready for that mission. But talking about readiness for the mission, you also mentioned something else that I love that you realized you needed to first attend to other areas in your life, your family, your health. Can we talk about that? Because I also think it's so important for people to and appreciate that you need to prepare for the next startup, unless you want to run out of motivation and energy in the middle of it. So tell me how you did it.
Omar:
[00:18:14 - 00:19:52]
Yeah, definitely. And I think, you know, to be clear, even though I did have this very clear calling, I'll call still was not like a easy decision in some ways because by, by really then then starting to repair and think about health, relationships, friendships, you know, I actually had some time to really begin to enjoy life a little bit. And that was also great. And to your point, I mean, I know we've had this debate on some of the forums that we're part of, but personally I don't believe you actually can build a life changing, generational sort of company without an enormous amount of hard work and sacrifice. And so, I mean, I think if there was a way to do it in 40 hours a week, then great, you could have the best of both worlds. But I do think you have to actually be honest with yourself about what it entails. And so it wasn't an easy decision. And I would say when I was during that two year period of in between startups and to be clear, I was working for the acquirer. And actually that was great too, getting a whole new experience and perspective. But ultimately I had a lot more time to really not only reflect but also get probably in the best shape of my life, really be there for my family and for my kids. And those are all incredibly important things. And so yeah, I think that was great and it made it really hard.
Anastasia Koroleva:
[00:19:52 - 00:21:00]
So I saw you with your family and I saw you with your daughters and what I saw back then was a man who is not only really competent with his children, but is so much enjoying like you're so physical with Your girls and they all over you. And it's just so organic and warm and beautiful to see your whole family together. And I remember watching it. And that was the time when you shared that you were kind of debating whether to go back to business or not and whether it's the right thing to do also vis a vis your wife, who is, you know, has this exceptionally successful career of her own. And obviously that adds complexity to the situation. And I was looking at you, at your girls, and I thought, oh my God, you know, his heart must be just, just in pain thinking that he would not be able to spend as much time with them if he goes back to business. So if you can help me understand on like, very personal level, like, how did you deal with that? Because I know it wasn't easy for you.
Omar:
[00:21:01 - 00:22:38]
In the end, I basically applied a regret minimization framework. So what would I regret more, doing this or not doing this? And for me, a big part of it was this really core belief that if I look honestly about not only my own startups, but also many of the ones that I've been around, it really is the case that market timing and forces out of your control are often a bigger factor in your success or failure than whatever you could control. And so, guided by that belief, I just really never would have expected that. I actually thought when we sold our last company, that might have been the peak AI, because even back then people were talking about AI, at least in the tech world. And then ChatGPT comes out and it's literally like a thousand X market growth. And you could see that it was going to become 1000x market growth even in the beginning. So I think a lot of it was when I really thought deeply and I really ran both scenarios in my mind. And it was an incredibly hard decision because to your point, now I'm talking to you from a hotel room and I'm not with my family and it's Saturday. And so that is kind of the downside, I would say, to this path. At the same time our business is taking off the market timing was exactly right. And that's not something that five years later, if I said, okay, my kids are now a little bit older, I'm. I'm ready for it. Right. I could just choose to suddenly have this, this opportunity.
Anastasia Koroleva:
[00:22:38 - 00:22:52]
Yeah, I could see that you would make that decision eventually because your sense of mission was too powerful. But can you tell me exactly how you organize your life so that you actually spend time with your kids?
Omar:
[00:22:52 - 00:25:38]
Yeah, so that's that. I mean, that Is one thing I would say I'm night and day better than I was the first time around, because first of all, I'm very, very conscious of it. And one, one realization I had is I think probably a lot of founders go through this where early on there's just, you feel like your entire success and life is on the line always. And so more, more work is always better, more hours is always better. I don't think that's true. I think there is an optimal number of hours and it's not the maximum number of hours. And so one thing that I've done very purposefully this time is I have pretty much every day blocked the early morning sort of couple of hours and then in the evening a couple of hours, we have dinner as a family pretty much every night together. I'll obviously go back to work, but it's been a really, really solid, I would say I actually drive my daughter to school and pick her up from school every day. And so we have, we have a lot of daily, when I'm not traveling, which still happens frequently, but whenever I'm home, we have a lot of time together. I also block the time to work out pretty much every day. So it's kind of like the health and then just from a lifestyle perspective, living a much healthier lifestyle too. And so the hours that I am working, I would say are like 120% efficient. And especially with AI now, it's actually beenan amazing way for me to transform how I work. And we can get more into that if that's interesting. But basically I've really protected my time much more carefully and thoughtfully. And then I think the other thing is, even from the very beginning, I recognized that even though I probably could have done this alone or maybe negotiated with a co founder or co founders to have an economic arrangement where it's definitely, I have almost all the equity and they have a smaller piece. I actually chose two co founders who I deeply respect, both of whom are incredible at what they do. And from day one, we split the company actually threeways. And so that was also quite helpful because I have really a team and I'm able to, with all those kind of factors coming together, not only spend arguably less time, like fewer hours, but the hours I am spending are all extremely high impact and really me achieving my potential, focusing on things that I can actually uniquely do for the business as opposed to just doing the million of things I need to get done.
Anastasia Koroleva:
[00:25:38 - 00:25:52]
So you intrigued me when you said that you can talk a bit more about how Exactly. You increase your productivity. So. So if you don't mind sharing something that you think people really should know and could move the needle for them.
Omar:
[00:25:52 - 00:28:23]
My own view is that people often talk about data being sort of the moat. I think that's very high level. I think the real moat and opportunity to really create unique value with AI comes from codifying institutional knowledge that's locked in people's heads and downloading the brains of experts. And so we're actually doing this with my new business where we will download the brain of some of the world's best lawyers. Once you combine that with AI, and those lawyers have years of experience working with this company, so they actually know a lot about the company as well, then you can actually build a company brain, we call it. And that's what we're basically selling in the market to each customer. But we've applied that same approach internally. And so for me, I've spent a lot of time basically and every day spend more time downloading my own brain and really codifying all of the like instead of just doing something which most people would just do a task. Maybe I can give an example. If I wanted to write a. I just wrote a manifesto, for example, for my company. It's on our website, right. Maybe in the past I would have actually spent, I don't know, a few hours writing that from scratch. Even though I've probably written several similar ideas in the past. That's more just my own brain's training data. But I've never actually in the task of write the manifesto that would be done from scratch. And most of us go a little bit from task to task operating in that way where even though you've probably done some things that are similar, you don't necessarily take advantage of that in the full capacity with AI. What I've done instead is actually build essentially my own operating system and my own content brain where I've found a way to feed every previous post I've ever made. Spent a lot of time refining that with AI so that I can be very, very clear about my own voice, the nuances behind my thesis, a lot of information about the audience that I'm targeting with various pieces of content. And then when I create the manifesto, it goes from being probably a five houractivity to like a 15 minute activity, right? Because AI has all this context and so I'm able to get it done very quickly.
Anastasia Koroleva:
[00:28:23 - 00:28:32]
I imagine you front loaded it, but then you keep adding more and more to that. It's basically a GPT, right? Of, you know, of you.
Omar:
[00:28:32 - 00:28:33]
Exactly.
Anastasia Koroleva:
[00:28:33 - 00:28:38]
So next time I can't reach you because you're too busy, I'll talk to that person.
Omar:
[00:28:39 - 00:28:44]
Or maybe next interview you might have already talked to him to get this meeting set up.
Anastasia Koroleva:
[00:28:45 - 00:28:48]
Are you real? Actually, is it you?
Omar:
[00:28:50 - 00:28:53]
That was my real solution. Just create a digital twin and then I could live my life with my family.
Anastasia Koroleva:
[00:28:54 - 00:30:48]
Soon we won't know, right? Soon it will be tricky. Okay, so Omar, we are now getting to a topic which is very close to my heart and I know it's close to your heart as well. I've done this research as you know, trying to figure out all sorts of patterns of post exit success. So I look at people who went through post exit exceptionally well and I usually zoom out and I look at like 10, 20, 25 years post exit to actually see which decisions ended up being wise, to see patterns. And then I do the same thing for people who are really struggling, even 10, 10 or 20 years post exit. And one pattern I shared with you, which I find absolutely mind blowing, is that people with background in philosophy or spirituality, but like serious background, tend to do much, much better post exit. And there are legends that we can name like Peter Thiel or Paul Graham or Stuart Butterfield, and even these people actually had formal philosophical training like you did. But even if we look back in history, like Benjamin Franklin or Andrew Carnegie, you can see in their biographies how important their strength in philosophy was for everything they did later. And it's especially the connection is especially strong when you think about really serious businesses built later. And I have a hypothesis about why that's the case. But I first want to want you to share because you are the person who is like that and you seem to be exactly on that amazing path. So I'm very excited.
Omar:
[00:30:49 - 00:31:37]
That's a great, a great question. I like the hypothesis, or at least the direction you're going in. I think my immediate reaction is when you study philosophy, you're literally studying things like how do you live a good life, why do we make the choices that we make and what are the different views on what's a good or a bad choice. So I think perhaps it's not surprising that people who have actually just given that a lot of thought are better positioned to then confront this post exit journey where someone else who just thought the technology was really cooland wanted to build it, but wasn't necessarily ever even asking these questions might have a harder time.
Anastasia Koroleva:
[00:31:37 - 00:35:05]
Because you mentioned Aristotle before as the reason you could relatively quickly rebalance and find your direction which is the hardest part people take 10 years or more to find it, and then sometimes they run out of esteem and just settle for whatever because they don't think they'll ever find that mission or direction or conviction. My hypothesis is, is basically there are three points there. So one is many people who are really struggling through post exit are struggling because they try to avoid the big questions that the exit posts. And these are not just questions, they're usually internal conflicts that cause cognitive dissonance. And sometimes it is a systemic cognitive dissonance because it affects every area of our lives. Soit's only natural that we try to speak, escape that. But the problem is that you can't quite escape it. It comes back and it's just how our brain works. When our brain comes across a cognitive dissonance, it needs to resolve it because it thinks it's not safe for us to be disconnected from reality. And it's great, right? But an exit is such a special situation when there are just too many of those internal conflicts. So I think people who had chosen philosophy as their field of study before actually welcomed this. And I think you welcomed it, and you know, Peter Thiel welcomed it. And it's exciting for them. Instead of escaping, they're embracing it and then they're growing through it tremendously. And another thing is that I think if you have this kind of brain that was trained on philosophy, you, you're just naturally much better. You're more skilled with dealing with all these paradoxes. You can live with them and you can resolve them. It's a skill, actually. It's a skill of thinking. It's a level of thinking that most people in business don't have because we don't need it for business. Maybe philosophers need it for the academic training before, but not necessarily for business. And then another thing that I found very interesting is that if you look at those stories, how philosophers did dealt with post exit, how they chose the next business, oftentimes they have so much conviction in very unconventional business. And that also comes from the fact that the brain is just trained to think independently. Right? Because philosophy, I often think how parents want kids to go to computer science. But I personally think that philosophy is what we need more than anything. Philosophy, psychology, spirituality. This is actually what we need in the age of AI. And I would love to bring these stories to the world to also help people understand that there are very powerful practical aspects to philosophy. But I would love you to help me with the following. Okay, you got this training in philosophy and you love it and you read It. But other people who didn't like, how would they, what your advice would be for them to catch up on that kind of thinking during this post exit period when suddenly we actually have the luxury of time to upgrade our thinking. How would you go about it?
Omar:
[00:35:05 - 00:36:50]
Yeah, well, first, I really like your theory. I think it makes a lot of sense and it's funny because probably the biggest thing that I took away from studying philosophy, which I don't know if everyone has this experience, but was actually a lot of comfort with my own hypocrisy. Right. And I think to your point, many people feel the need to defend their views and basically adapt their views to correspond with their actions to try to justify whatever they're doing. Right. But actually one of the biggest learnings for me was for example, I think it's personally wrong to kill animals. I don't think it's a. Again, I mean all things equal, if you have a choice to go for a walk or kill an animal, I think it's worse to kill an animal. But I also eat meat and I enjoy the taste of meat. Right. And so I don't feel the need to pretend like it's a great thing to do to kill animals because I like the taste of meat. It's fine for me to hold those two views together. And it's one of a million ways that I'm hypocritical in terms of my actions don't necessarily line up with my views of being the most ethical person. So to your point, I do think being able to think in that way because it does require, or at least it helps when you then are making a decision that just has a lot of trade offs to be able to not only see that but also have a level of comfort with it. So yeah, I think it's a great theory.
Anastasia Koroleva:
[00:36:50 - 00:37:04]
I'll give you another one. I'll give you another one. You may be really concerned about AI safety because no one actually knows where AI is going and yet you decide to use it for a beautiful mission. Right? That's a paradox.
Omar:
[00:37:05 - 00:38:09]
100%. Yeah. There's so many. Yeah. And I think to your other question, I mean I do think one sort of byproduct that's maybe not the best is of AI adoption. And just everybody going digital is. I don't think people read as much, which is fine, but I do think reading the actual source material of philosophy would be good. I think a second best alternative would be one of my hacks when I don't have time is to just go on YouTube. And actually, if you look up, I mean, we now have access, the kinds of professors that I had at Oxford that are incredibly hard historically to get access to. I mean, a lot of this is now freely available. So I do think paying attention to who the actual experts are and then finding ways to be able to even just go on YouTube and find interviews with those kinds of people, I mean, you can really learn so much now. And I'm actually very optimistic about AI in education for some of the same reasons.
Anastasia Koroleva:
[00:38:09 - 00:39:29]
And I think AI is much, much better than all these apps that just summarize books, because I think when it comes to philosophy or psychology, that doesn't work. Because, okay, you just read these conclusions, but the whole point is reading through an amazing thinker's thinking, right? You read Aristotle and you're like, okay, he's teaching me how he's thinking. It's not about his conclusion. Again, as you mentioned, his conclusion is shared across pretty much every spiritual or philosophical tradition. The conclusion itself is not the point. It's getting to it. It's training your mind to get to it. But I'm happy you mentioned AI because I'm actually really curious. Do you think, like, if somebody wants to do this efficiently, would you say, chat with AI about the topic would be reliable, or is there an app you would trust with this? Because, of course, the problem is when we talk to ChatGPT, the source is not necessarily reliable, believable or right. There's so much crap out there. How do we not waste time or get confused by poor sources if we want AI to teach us philosophy within a year before we start a new business?
Omar:
[00:39:29 - 00:40:50]
I think, unfortunately, we are in sort of the messy middle of really where this technology is. Because when I look ahead, hopefully a few months from now, but maybe a few years from now, I believe that I'm not alone in downloading my brain. And you'll actually see pretty much every expert will have a download of their brain and a system which actually is reliably only pulling from that kind of source data and combining it with AI to then give the experience that you're talking about. Where if you wanted to have a tutorial with the same professor that taught me at Oxford philosophy, you'd essentially be able to do that and you'd have some comfort that it's actually reliable. We're definitely not there today. And so, yeah, it's not easy to answer in like one minute, but I. But I would say the one minute version. Personally, I would still go to YouTube books really kind of finding reliable information from experts. And then you can always feed that to AI if you're proficient at knowing how to do that, to be able to make sure that it's actually drawing from the right material. But today I would say the general purpose LLM may lead you down the wrong path, unfortunately.
Anastasia Koroleva:
[00:40:50 - 00:41:00]
So I get it about philosophy, how spirituality helped you adjust to post exit life.
Omar:
[00:41:00 - 00:42:26]
Yeah, that's a great question. And I liked how you linked the two because I don't think everybody links the two. For me, I think there is an element of intuition which is extremely important to me. I think there's a. I want to say it's a Sigmund Freud quote that for insignificant decisions I weigh the pros and cons. And for significant decisions I just go with my intuition. Right. I think there's a recognition that we still don't really. A little bit like deep learning models, we still don't really understand even our own brain and why we're sort of sometimes just have very, very strong intuition to do one thing versus another. So I think that's maybe what I would more call the spirituality part of this, which is even though I have these seemingly rational frameworks like the regret minimization one that I described, the. The truth is for something like this you do just need to really go with your gut and follow your instinct. And I think those of us who've had some experience and enough time to think about these topics in sort of the right setting and in the right way, that that intuition, I would say, is a little bit closer to the spirituality piece of this, where you almost have to just believe that that is the right thing to do, even though it's not necessarily rational.
Anastasia Koroleva:
[00:42:27 - 00:43:31]
Yeah. Because I found that spirituality is extremely practical in post exit if you actually wantto find that mission. Because this whole topic of finding your calling, it's your spirit reacting. Right. It's like what I saw that day when you were sharing your mission. I saw your spirit lit up. And yes, of course, you decide with your brain what it is exactly you're going to do, how you're going to shape it into a product that's actually helpful to the world, that's fine. But you call it intuition or whatever it can be, there are many words for it. But it's this feeling. This is my thing, this is my calling. Right. And if we don't believe that it's possible, this is how we set up. Right. So spiritual skepticism literally kills our chances to have a fulfilling life. Post exit, it's extremely practical, extremely relevant. We don't need to go and sit on the mountain for years or anything like this. We just need to appreciate that our spirit actually exists and it matters and it should lead us.
Omar:
[00:43:31 - 00:44:17]
The other thing that's kind of interesting and reflecting now after now over two years of doing this new startup is, you know, people often talk about product, market, fit. I don't love that term because it sort of implies, okay, if I build a product and I just sort of keep walking, maybe around the corner, I'll find the market and then there's the fit. I think what I've learned is you create the market as much as you create the product, or at least there's an opportunity to create the market as much as you create the product. And so it also, I think when you have that feeling and you really believe in something, it does become or can become more of a self fulfilling prophecy. But you have to be all in with it to be able to make that happen.
Anastasia Koroleva:
[00:44:17 - 00:44:33]
Yeah. And it has to come from that place where you believe that your mission is to, to increase the pie. Right. Not to compete for limited resources, but actually to bring something brand new to the world. And this is when it becomes really interesting, isn't it?
Omar:
[00:44:33 - 00:44:54]
Yeah. And there's this feeling that I've had now, like it's almost, maybe not quite every day, but every week where it's like, I'll talk about what we're doing, I'll talk about the mission. And it's almost like people can't unhear it once they've heard it, but no one said it out loud before. And so that's also, I think, a big part of that.
Anastasia Koroleva:
[00:44:54 - 00:45:19]
But that's connectedness. Right. When you share in your mission and other spirits lit up. This is the very, the actual essence of spirituality, isn't it? How we are connecting and sharing energy through these things. And it's so beautiful that there are people like you who have this spark and then this spark can go to other people and then beautiful big things happen.
Omar:
[00:45:19 - 00:46:54]
He also talks a lot about how each of us has some kind of unique strength. And even on aobject level, like if you look at a flute, it could be used to hit somebody as a stick, but its real purpose is to actually be played as an instrument. And so he has this idea that all of us have a purpose. And that purpose actually ties to what's our unique function or functional capability. And so I think that's one thing that I would encourage post exit founders to reflect on is what is that thing that you're Actually uniquely good at. And for me one of the realizations was this idea of the ability to actually create the market as much as the product, to really build trust with a buyer who doesn't normally trust somebody very easily actually felt like one of my unique abilities. And when you marry that with my co founder's unique abilities, it just felt like we had, I mean it's almost borderline. I wouldn't say like ethically wrong, but if you have that incredible capability and the market is ready for this, and if you were to do it, it actually would have a major impact, then it actually feels almost like a moral failing to not do it.
Anastasia Koroleva:
[00:46:54 - 00:47:01]
You would say that the right attitude to have, it's my duty to find it. And I fail if I don't. If I don't.
Omar:
[00:47:01 - 00:48:24]
Yeah. And I think a little bit of ties like, you know, for, for, for me there's, there's also an element of controversial. But I, I really do believe there's a relatively small percentage of people who actually are responsible for having an outsized influence on the world. And so if you are one of those people and you actually have that gift or that ability, which you may not be able to take any credit for it, but for, for whatever reason you have it, then I think we've settled in general as a society. And there's been a lot of people who might take that talent and build some credit card points app which helps you get Uber eats faster or something like that. Again, not to denigrate on anyone who does anything. I think we all need to create businesses and that would also add some value for the world. But when you have that opportunity as a post exit founder to really actually do something that could have a major impact, solve a real problem, achieve something great that's never been done before, what I found is that's incredibly rewarding and it's actually easier to recruit people to go after a very hard problem than it is to go after an easy problem. So it actually might even be easier, paradoxically because once you have the right.
Anastasia Koroleva:
[00:48:24 - 00:48:33]
Team and you attract the right kind of people, you attract the people who also want that challenge. They want to make their mark.
Omar:
[00:48:33 - 00:49:29]
Exactly. And I think even customers frankly kind of recognize it. Because when I look at what we've done, I mean we're violating all the conventional rules of Startup101 in terms of you should build an MVP, start with this niche thing and instead we're literally going after a whole industry. We bought a 300 person legal services company, we created a law firm that's the first AI powered law firm. I mean we're doing things in like the span of weeks that no startup would normally do in their right mind. But it's kind of building a lot of infectious energy, I would say where any customer or prospective employee or investor who sees that ambition married with actual execution is getting inspired by it and then it's kind of building it. And I think a lot of founders who have had that initial success, you learn so much and you make so many mistakes that you can actually be in a unique position not to make that set of mistakes again. And now really up level your ambition, which has been really rewarding for me.
Anastasia Koroleva:
[00:49:29 - 00:49:59]
Yeah, that's actually super important to understand because I think there's so much fear of work among post exit founders. Understandably. Right. It's so hard and we are no longer naive about it. And how would you go about overcoming this fear, you think like if really embracing the mission or what you said regret minimization framework, right? That's what worked for you. Is there anything else you think could push people through the fear? Because that's the only way to address a fear like that.
Omar:
[00:49:59 - 00:51:02]
I mean just to go a little bit deeper on the regret minimization framework. And you and I have both been in some of these groups like, like Tiger, where I've also had the luxury of now seeing people who are 10, 20, 30 years older than I am and watching maybe less scientifically than you've been doing on the pattern recognition side, but anecdotally observing people who are achieving eudaimonia versus those who aren't in their later years. And I think that's. I think the other thing that I would say to some of the post exit founders who are contemplating what's next is it's not like if you sit on the beach and play golf for 20 years, you're going to be very fulfilled and necessarily deeply satisfied. And if anything I've noticed probably the opposite, that people who just almost go on permanent vacation, especially when they have their health, they have a lot of energy and potential that could be used, but they don't use it in some meaningful way, are actually among the least happy.
Anastasia Koroleva:
[00:51:03 - 00:51:10]
So you're basically suggesting using fear to help you go through this fear, the fear of vegetating on a golf course.
Omar:
[00:51:12 - 00:51:59]
Yeah, well, I mean, I think it's just maybe honesty with yourself that the real decision is which path do you go down and thinking deeply about jumping ahead, what is that path actually going to look like? I think that's part of it. And then I really do think the mission part, that's something that it's a little bit back to sort of Maslow's hierarchy of needs. Once you're in the luxury, especially if you had a financial exit that was successful, who else can we expect to basically fix the real problems in society or actually go after these bigger picture things than those of us who've had the luxury of actually no longer needing to worry as much about the day to day financials which almost everyone else does. And they should be focused on that if they do.
Anastasia Koroleva:
[00:51:59 - 00:53:30]
Yeah, and you're totally right. Maslow is a great example of showing how our motivation naturally evolves from fear and need for safety all the way to the desire to contribute, which is basically how self transcendence manifests in the world. But even if we go to, you know, Eastern spiritual traditions like something like Vedanta, you would also find very similar view on motivation. We have fear and greed as lower motivations, but then we have love and duty. And I think what's beautiful about everything you are saying is that I can just see this love and this voluntary acceptance of duty that give you energy, right? People think, oh, I don't have the energy to pull another startup. But I found the opposite is true. We actually getenormous energy when we are motivated by love and duty. And I'm at this place as well and I just try to tell people it's so beautiful to be at this place. And I wish I came to this place earlier because there is no point sitting there being fearful. And another amazing, unexpected surprise for me was that not only employees are attracted to bigger missions, but everyone suddenly wants to be with you if you generate this spark, right? If you're on a mission, people just want to be physically close to you. And it's so beautiful, isn't it?
Omar:
[00:53:31 - 00:54:27]
100% yeah. And I think maybe the last thing I would say is it's also interesting because even though I was thinking of it as this sort of either or of prioritizing, I'll just call it family relationships, health or diving to the startup. I don't think you can have the best of both worlds, but I do think you it's more complex than a either or decision. And I think on some level, especially those of us who have had an exit, who have kids, I think there's something to be said for also modeling hard work mission, like really going after solving hard problems. And that's actually been a nice reflection is that even though I am away a lot more than I'd like To be from them. I think at the same time, they're watching me work extremely hard. Whereas I think if I was playing golf all day, that would also be kind of.
Anastasia Koroleva:
[00:54:27 - 00:55:26]
I think one of the reasons that people don't really get this importance of purpose and fulfillment is that so few parents model it. Because theoretically, this knowledge is out there, Right? Millennia of knowledge of how happiness, fulfillment, purpose, work. Like all religions basically saying the same thing. And yet Aristotle saw the problem at his time, and it's exactly the same problem we are discussing today. And at the end of the day, it's because people are actually not living this and not not modeling it to their kids. And theoretically, this knowledge doesn't mean anything. It means something. But you see, even you, with your philosophical background, only fully internalized it when life pushed you to face these questions post exit, Right? And that's why an exit is such an interesting blessing, because it does these things to us. It actually forces us to internalize ancient wisdom and live it.
Omar:
[00:55:26 - 00:55:55]
Yeah, yeah. And then the only other thing that I might want you to ask, just because it comes up all the time, is people can't pronounce my company name. And I think there's a nice tie in here because Udia actually comes from Eudaimonia. And so that's a daily reminder that that's why we're doing what we're doing. And it's all about really, this objective of helping people achieve there. So, yeah, maybe if you don't mind asking me about the name and then I can. If you could weave that in, that'd be awesome.
Anastasia Koroleva:
[00:55:56 - 00:56:03]
So, Omar Yuzia. Such a beautiful, unique name. What inspired you to pick it?
Omar:
[00:56:03 - 00:56:41]
Yeah. So the name Eudia comes from Eudaimonia, and Eudaimonia was that concept I was talking about around people achieving their highest good. And that's actually our mission at the company is to help people achieve their highest good through what we call augmented intelligence. So really combining humans and AI, and that's the problem that we're ultimately solving, is what does that optimal combination look like so that people can actually be more human with the help of AI and AI can do the work that none of us want to do and sometimes wasn't even possible for us to do before. So that's the name Udia.
Anastasia Koroleva:
[00:56:44 - 00:56:54]
Omar, I always. I know I need to let you go. And I always finish with the same question which I have to ask you. How do you want to be remembered?
Omar:
[00:56:55 - 00:58:10]
That's a good question. Given the mission that we have with Udea, I really think a big part of it would come from if we could be even a small part of changing a system which is going from time spent equating to value delivered and basically the whole professional services industry which is packaging judgment into time and then charging people kind of inordinate amount for that judgment if we could be a part of that change where we actually shift from that world to 1 of AI representing mass cognition and making not only legal services but all knowledge work much more accessible to really enable humanity to uplevel what we're all doing and also removing a lot of the barriers for not only access to justice but also for businesses to grow that would be an incredible legacy and that's really on the business side I think on the personal front I'd obviously love to also be somebody who did succeed as a father and husband and friend and made a good impact on the world.
Anastasia Koroleva:
[00:58:10 - 00:58:17]
Amazing. Thank you so much. What a beautiful interview. Thank you for sharing so openly thank.
Omar:
[00:58:17 - 00:58:19]
You for having me it's been great.
