Latest / Success Story with Scott Clary / Kristina Subbotina - Lexsy Founder & CEO (Ex-Cooley) | What Happens When You Stop Playing It Safe and Actually Bet Everything on Yourself

Transcript

Kristina Subbotina - Lexsy Founder & CEO (Ex-Cooley) | What Happens When You Stop Playing It Safe and Actually Bet Everything on Yourself · Success Story with Scott Clary

• 0:00
  Was there something that happened that made you say, my life is good, but I need to go to the US? Nothing happened. I thought I'm just going to go get the education. It was my dream. I got a grant to get education, and they paid for my living expenses. It was that feeling that I would regret if I don't do it.
• 0:16
  Christina Sabatina, corporate lawyer, entrepreneur, and content creator. After nearly a decade representing startups and top VC funds at firms like Cooley, she took the leap and founded her own law firm, Lexi. She now shares legal tips and her founder journey with a growing online audience. When you take a chance and things aren't working out, how do you stick with it and not go back to the thing that you were doing before? What helped me that time, the book Power of Now, Akratole, being really present.
• 0:43
  What would your advice be to somebody who is an immigrant founder, who's scared as hell and stressed out? Trust that because you are here, there was a dream. If you didn't have the power to make it through, you wouldn't have the dream. That dream was there for a reason.
• 1:03
  My fitness pal is a success story partner. Now here's something I've noticed after interviewing hundreds of founders, the ones that are performing at the highest level, the ones that are truly winning, they aren't just optimizing their business or their calendar or their team, they're paying attention to what they eat. And the ones who aren't paying attention, they're usually the first ones to burn out. And that pattern is consistent enough that it got me thinking about my own nutrition,
• 1:23
  Not whether I was eating well, but whether I actually knew what the big picture looked like. That's why I started using the MyFitnessPal app. I wanted to see what I was actually eating, not what I assumed I was eating, but the real numbers, what my protein intake looked like, what my macronutrient breakdown was, where my calories were actually going throughout the day. And the app gives you all of that. Now, what kept me using it is that there's zero friction.
• 1:44
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• 2:16
  I was reading an article where you were interviewed and this quote really hit me. So when I sit across from a founder, I see myself, the immigrant who arrived with nothing, overwhelmed by new rules and new realities, but willing to bet on herself anyways. So take me back to the new founder immigrant, Christina. Who was she? What was she thinking when she came here?
• 2:39
  Oh my God, I even have a little bit of tearing up because I was so overwhelmed. Yeah, I came in 2014 to study law at USC. They fully paid for the education, for living expenses. And I didn't know a single person in the US. So I drove myself from LAX, rented car in an apartment that I rented while in Russia with the furniture that I rented while in Russia.
• 3:08
  My English wasn't perfect, so I couldn't understand jokes or just, you know, banter. And improvisation, when you talk, that was really hard for me. So I was very overwhelmed. I have to study English and law in parallel. I would have a dictionary always next to me. I failed, I think, one of the first exams, U.S. topics in American law, something like that. And I was like, what am I doing?
• 3:39
  What am I doing? Why did you come? Why did you come to the US? Okay, it is a little cheesy, but I always had the dream. I'm born on July 4th, so I always had that on the back of my mind that I am meant to be here. I don't know what, why, but there is a reason behind it. Plus, all of the Hollywood movies and cartoons, so I grew up on that. And I think United States make really great marketing.
• 4:09
  The United States is like a startup that is really good at distribution. So American Dream, my birthday, and I always dreamed of studying abroad. But there was no plan. It's not like your parents were pushing you to come to the U.S. It was just, this is where I want to build a life.
• 4:33
  I didn't even mean to immigrate. I came to study and I thought I'm going to go back. But then the war started and my rubles, my savings in rubles started going down. And in 2015, when I graduated from USC, I came back home to see what are the options, whether I should stay in the U.S. or come back home. And everyone advised me to at least get experience working in the U.S. for at least a year. So take the bar exam, get the experience.
• 5:03
  and I stayed I got the experience and then the life just took me further the war is still happening and it's just more opportunities here so I think it naturally happened I even bought I bought a car specifically like the year of production to pay less taxes to take it back like I literally planned on going back
• 5:28
  And when you came here, like, did you have much money saved or not much? Because you haven't really started your career at this point.
• 5:36
  Well, I had my career in Russia. I was a lawyer. I already got my JD. And I was one of the youngest government officials. So I went to law school when I was 18. And I became a governmental official when I was 22. And I moved in the United States in 2014. So I already had my apartment, my life, my boyfriend, everything. So it was fully set. And I left it all behind.
• 6:05
  And was there something that happened that made you say, like, my life is good. It's going. I've spent all this time and energy investing in career and boyfriend and everything. But I need to like, I need to go to the US to basically restart.
• 6:20
  Well, nothing happened because I didn't think about restarting. I thought I'm just going to go get the education. It was my dream. And once I got a grant, $80,000 to get education and they paid for my living expenses. So it would be stupid to reject that opportunity. But yeah, I don't know. It just like was that feeling that I would regret if I don't do it.
• 6:43
  Do you know the Jeff Bezos regret minimization framework? Yeah. Is that sort of what you went through? And just for people that don't know what this is, you kind of fast forward to yourself on your deathbed and you just wonder, like, if I didn't make this decision, would I regret it? And if you would, then go back to today, go back to the present and then make that decision because that's the worst thing, right?
• 7:02
  Yeah, and I like what Jeff Bezos said, but also I think about plan A, plan B, plan C. I always love having plan B and plan C. And as long as, you know, I have ambitious plan A, I usually never go back to plan B. And I'm thinking, would I be able to go back? If I leave this job, would I be able to go back? Yes, then the worst case scenario is going to what you already have. And that was my thinking at that time as well.
• 7:32
  This whole idea also of the worst case scenario being not that bad. It's very interesting to me how everybody who takes risk, they all sort of believe this.
• 7:47
  But I don't know. I'm trying to figure out why people, why some people look at life this way and why some people don't. Like some people are so scared of risk and chance and uprooting their life and going to another country or whatever. But some people, like yourself,
• 8:04
  It's like such an easy, it's such an easy. It is not easy. But you know, hear me out though. It's easy. It's an easy decision to make because you know that if it doesn't work out, you can always go back to the thing that you had before. It's an easy decision, not...
• 8:19
  I think even decision is not that easy. Honestly, I felt terrified. And now running my company, I feel terrified. I think courage is not the lack of fear, but very intimate relationship with the fear. You feel it and you do it regardless.
• 8:36
  And because you cannot imagine not doing that, not doing that feels worse. Being stuck somewhere feels worse. Not trying feels worse. So it has to be to the point where it's like that uncomfortable that you have to do it.
• 8:54
  I think so. Because if it's not that uncomfortable, you're going to quit because it's really hard. And I think why people not do it, it's the amount of discomfort you have to deal with. So, for example, starting a company, I frequently feel discomfort. And in those moments of discomfort, I remind myself it's temporary. And it truly is temporary. But imagine if discomfort lasts a couple of months, a couple of years.
• 9:21
  When I came here in 2014, my discomfort lasted for over two years. But you're still in your mind, what you're saying is you're weighing that discomfort. So the discomfort of the risky, the perceived risky thing versus the discomfort of staying the same. Yeah. And I think I'm just curious person. I'm always curious. And I think I disrupt myself every couple of years, even in my business. After leaving Big Law, I started tech-enabled law firm.
• 9:48
  And then I was running for two years, like over a million dollars in revenue. And it was just me, one part-time help and product manager. I was automating workflows and I decided to disrupt myself again. So there is something in me that always pushes me to move forward and see what else, how far we can go. And I've always been like that. And I used to
• 10:12
  blame myself for that. I'm like, why can't I chill? Why can't I enjoy where we are? But I realized that's the quality of an entrepreneur. And that's what happened when you were comfortable in Russia and then you came here. You're like, this is good. Everything's good, objectively good, but you disrupted yourself.
• 10:31
  Did I regret in the first year or two? A hundred percent. I'm like, what did I do? What did I get myself into? But then you look back and you connect the dots that everything was meant to be. And now when I'm taking bigger risks, I am my own biggest inspiration because I look back and I'm able to trust myself more because...
• 10:54
  I already trusted myself once. It worked out. I might not know all of the answers right now, which you usually never. But looking backwards, a couple of times I took big risks. It paid off. So now, even if I feel scared, I remind myself I did it once. I did it twice. I can do it again. And that trust and confidence that I can always start over. That two-year period when you took a chance, you moved here, you're figuring everything out.
• 11:23
  year and a half, things still aren't working out. What's your advice to somebody who's going through something like that? And if they had just persevered another six months, or maybe it's another year or maybe another two years, like when you take a chance and things aren't working out, how do you stick with it and not go back to the thing that you were doing before? Yeah.
• 11:44
  That is a really good question. What helped me that time? The book, Power of Now, Akertolle, being really present. The way I passed the bar exam, I was meditating. I didn't know the word meditation. I was just very present, focused on my breath.
• 12:02
  And in a couple of weeks, I almost became a superhuman that you have insane intuition. So on the bar exam, I didn't know certain words in English. And because I was so attuned and so present, my intuition was on a different level. I guessed the answers right.
• 12:21
  I connected the dots. If I don't know what this is, I'm like, okay, this is standing on a table and it's close to me. So I could make connections between things, even if I don't know this is microphone. For real. Yeah. And everyone can do it. Like with meditation. Now I know what meditation is, breathing and energy. But at that time...
• 12:45
  I felt so anxious and I knew that I needed to do something in order to help me. So the book being present in a couple of weeks, it truly, you start seeing opportunities other people don't see. It's almost like you're playing a game and you see all of the signs from the universe. So you passed your bar, not even speaking English.
• 13:08
  I was not proficient. I didn't know all of the words. And I spoke English, but for example, for job interview, I had to memorize my interview. I couldn't just join and have a fluent conversation.
• 13:21
  That's incredible. That's very impressive. No, I didn't know this about you. That's really, really impressive. So even with the fact that you could not speak the language fluently, you couldn't just riff and just chat. You passed the bar and then you got hired. You got a job by memorizing the interview or was at that point, like obviously a whole bunch of things are
• 13:46
  you know, you're studying, you're passing the bar, you're learning English, you're applying for jobs, like you're trying to figure out life in the U.S. Was there anything you did that ever came easy to you once you got here? Because it seems like everything was all uphill. It was all uphill. I think the luck comes with quantity. You put the effort. So, for example, I will send in hundreds of LinkedIn messages. To firms. Yes. To have informational interview, coffee with a managing partner,
• 14:14
  And then I jumped on a call with one of the professors who knew a federal judge and I needed an externship or internship. And that professor connected me to a judge. I came to the judge. I was like, oh, this is my friend. The judge had worse, worse accent than I did. A lot of immigrants like that's the thing, a lot of immigrants. So he didn't realize that my English wasn't that.
• 14:39
  And I did remember, I did remember my, my lines and everything. So I had to memorize the interviews and his clerks interview me and they're like, how, how did you meet? And I'm like,
• 14:54
  I didn't know what to say because it was literally two phone calls and because I was sending hundreds of messages to everyone because I needed one opportunity, someone to sponsor my visa. So I had to I had to hustle for that. And the school wasn't sponsoring your visa.
• 15:11
  I had OPT for a year. So it basically gives you opportunity to work after graduation. So one year. Only for one year. So I spent half of that year working for a judge. And my first job, it was a fintech startup in Santa Monica.
• 15:28
  And how I got in, an immigrant hired me, actually. I applied through the job applications with USC. They have a career portal. So I applied and I stood out because even at the time, I actually had startup ideas. And my startup idea was very similar to what their startup was doing. And although I was applying for legal position, they thought I stood out because I have this entrepreneurship.
• 15:57
  And because the person who was hiring me also didn't have that fluent of English, we're like, okay, we're mixed together. That was the first job. So the first job was not Big Law. They were not. What did that startup see? And from what I understand, you helped them grow from C to Series B, that first startup. So what did they see in you that Big Law did not see? I think they saw themselves in me, right? A person, immigrant with hunger.
• 16:28
  And they had big law firms they were using for legal, so they wanted to save money. So they hired me as their first legal hire. And when I joined, it was a mess. No one knew what kind of company we would have. I've been told it's a California corporation. I'm like, no, this is a Delaware corporation. I had to reconstruct the whole context about the company. I was reporting to the chief product officer, and we both were very lost. Honestly, I'm kidding.
• 16:59
  But they were paying huge law firms.
• 17:02
  Well, they trusted me to manage big law firms. And I started managing them. And they sent 70K bill. And the co-founder of a startup like Christina, this is not sustainable. We have to, like, we cannot afford paying this. So I had to do a lot of the work myself and use big law only for certain things. And the funny thing is that before I got hired by a startup, I almost got a job at a big law firm, D.L.A. Piper.
• 17:30
  I know them. The last stage when they realized I only have six months on the OPT, they're like, we're not sponsoring. So startup took a bet on me and Big Law didn't. You say that when you sat across from that startup founder, you saw yourself. What do you mean?
• 17:50
  Immigrant, big dream, operating in a gray area. It was fintech giving loans in emerging markets. So we couldn't be a bank. We didn't have money to be a bank. We had to find legal loopholes to say we're a software company.
• 18:09
  So, like, you know, the way how I was sending 100 LinkedIn messages trying to land my first job, they were trying to expand in the markets with the budget that we had without being a bank. And now it is normal to be a fintech company that is not a bank. But at that time, you had to be very creative. You said that the startup founder experience and the immigrant experience, they're very similar. Yes.
• 18:38
  Why do you think that? You take big risks. The level of uncertainty is incredibly high and discomfort. So frequently when you come here, you don't understand culture. There might be difference in currency. Whatever money you had, it's different money here. You don't know literally what's happening. You don't have parents to go to, to their house, to their basement. Language barrier.
• 19:05
  You don't have people support system and it's all scary. You take a huge risk. Yeah, I love this idea of like the immigrant mindset because like you're an immigrant, you come here, like there is no plan B. So you can't fail. Like it's just it, like you just gotta be successful.
• 19:29
  especially the way that you came to the US. It's literally like, okay, you got your education. You have 12 months to figure this out. It's not like you came here on a business visa where you invested half a million, a million dollars, and you have years to figure out how this business model is going to work or whatever Trump's new visa is where I think you can...
• 19:52
  to spend a lot of money and get a visa. I don't know. I just didn't have that money. No, so you had no money. You just had, okay, I have education. And then after the education is done, it's like, okay, countdown starts. Yeah. So it's not only just figuring it out. It's like figuring it out in a very condensed time frame.
• 20:10
  Exactly. That's why when I was getting education, I had to send those hundreds of messages and land the externship or internship because I needed to work with someone for them to see my worth to being able to sponsor me. I knew that I'm not going to get sponsored right away.
• 20:26
  I need to prove myself. And while you're getting the legal degree, you need to prepare for the bar exam as well in parallel and find that internship externship. So I was doing three things in parallel. And either of them could have failed either
• 20:43
  That's why that level of uncertainty right now, as a startup founder, still like now payroll, I'm responsible for money in figuring out product market feed. But compared to what I went through that time, it is not that bad. Like it's only going up from there.
• 20:59
  It's funny when like when when you have hit. I don't want to say rock bottom because that's not right. You were not in a bad place when you when you immigrated here. You still had some resources, but not rock bottom. But like. But it's a floor era. I had a mattress and I was studying on a floor. I have photos. It's incredibly discomfort. Like it's like discomfort is very high at this point.
• 21:19
  Yeah, and I was used to really nice lifestyle in Russia. I had like a Mercedes Coupe, like a couple of apartments, and I was doing cool things here. I had to start from the beginning. So it also took me a time, honestly, to accept that no one is hiring me to run stuff.
• 21:38
  I'm going to be at the bottom of the pyramid. I have to also learn English. I still have a couple of years. So that's surrender to being lower at the level. And another thing is that...
• 21:54
  Because I didn't speak fluent English, it was really hard for me. I'm a lawyer. I was trained by a lawyer. So I can put any person in their place. I didn't know English enough to put people in their places. And when I was buying a car, the salesman was so rude to me.
• 22:09
  And I even started crying because I'm like, if it was in Russian, you would be crying here. But I couldn't express myself in a smart way to, like, put the boundary. So I think that was also hard. Now, knowing English, I feel very comfortable. Like, knowing English, being a citizen and...
• 22:30
  Being a lawyer here, I feel like I can, even by myself, I'm very self-sufficient, but I also have the network. But at that time, I was alone. I didn't have any support here. My money, my savings were going down because of the currency. My English was broken. So like even me protecting myself was really hard. So I felt like very vulnerable in that position. So...
• 22:54
  I had to surrender to whatever. Like, God take the wheel because, like, I don't know what I would do. What would your advice be to somebody who's listening to this who is an immigrant founder, who's scared as hell and stressed out? Like, what is your words of wisdom to that person?
• 23:12
  trust that because you are here, there was a dream. There was that seed that is in you. If you didn't have the power to make it through, you wouldn't have that dream. That dream was there for a reason. When I had my dream to study in the US, there was no good reason. There was no logic. I didn't have... In my family, no one even speaks fluent English. No one in my family is a lawyer.
• 23:43
  If you have those dreams, no matter how big, audacious trust, there is a reason there. And learn to train your nervous system to relax in uncertainty, in discomfort, and let go. And go with the flow in terms of focusing on the next step. What, like, one thing that you can do? For example, the visa situation, how I figured it out.
• 24:08
  For three months, I didn't know whether I would even have a visa, but I just, I was researching what are the options, who can sponsor, how. And I just, even if three messages are applications a day, it is better than zero. And even if you feel down, if you can't run in the direction, you can walk if you can't walk, like at least lay down in that direction.
• 24:33
  I love this. I think that so many people, it could be immigrant founders, just like non-immigrant founders. They always have this feeling of what they should go after.
• 24:43
  Ambitious people always do. They always are like, I'm destined for greater than whatever it is I'm doing right now. But I feel like so many people don't have the courage to go after it. And they kill those dreams. And they self-select out of this opportunity. I don't know how else to describe it. And half this podcast is just me trying to convince people to just go after whatever the hell they want to go after. And just stick with it long enough. And they'll figure out how to make it work.
• 25:13
  At the end of the day, most of the advice I give is like, hey, how do you do this for like the next 15 years? Because if you can figure that out, everything else takes care of itself.
• 25:23
  I don't know if I told you this story. There's another guy that I'm mentoring and he was trying to figure out whether or not he should go take a job. I think I told you this story. Yeah. Yeah. So he had an app he was building, invested in it, and we were having to call. And obviously he's trying to go over like, you know, like, you know, all the KPIs and whatnot. And I'm like, like, I asked him, how are you doing? As a human, like, how are you doing? And he's like, not great.
• 25:49
  Like, he's like, I'm running out of money and I'm stressed as hell. And I said, well, how do we solve this? You can go raise. There's like many different ways to do this. And he's like, yeah, but I don't want to raise and I don't want to dilute more. And I'm like, do you want to keep doing this? And he's like, yeah, I do want to keep doing this. Okay. And okay. So.
• 26:05
  Can you, because he has a CTO too, can you still work on it? Like even part-time, like no one's in a rush here. Like really, like it's fine. Like we're, we're not trying to hit like, you know, our, our returns and like the next like, you know, quarter, like we can, we can chill. This is not a big deal. And she was like, well, I've been trying to think about whether or not I should, I should get a job or raise more money. And I'm like, what do you, what would.
• 26:28
  What would make you more comfortable? And he just said, if I got a job. So he, I don't know, I don't think he needed my permission to do it, but I think he was just wondering like what investors would think if he went to get a job. And in my opinion, at least I was super happy for him because that means he can keep doing it and he can build on the side and he's not stressed out financially. And he's like a smart guy. So he could probably pull in, you know, 200 quite easily a year with like a sales job.
• 26:53
  And that's what he did. And now he's way less stressed and he's making his he's making about two to twenty. And he's still building on the weekends and at night. And now it's no longer like you can feel the energies like different on the call. Like it's not like he's given up, but he's no longer like manic, if that makes sense. I can suggest one more option. Focus on revenue. Yeah.
• 27:17
  So in the beginning of your startup, you can almost have an agency inside of your startup as long as it's aligned with the vision and the mission. What do you mean agency inside your startup?
• 27:27
  So for example, we have revenue at Lexi. We provide legal services, right? And there is the component software fee and there is the services. So I always focus on the revenue and that's the best way to not depend on the money. On that estimate, yeah. So, okay.
• 27:49
  So if he's building software, find a way to make money, especially now in the age of AI. Software, it's not dead, but I think software as a service becomes more and more prevalent because software is easy to wipe code.
• 28:07
  Obviously, when it's scale, in order to produce something safe and scalable, you do need software engineers and stuff. But finding a way to make money while doing the thing. So, for example, my law firm, before starting Lexi, I was running tech-enabled law firm. It's more cash. But I was proving and I was automating things. So whatever I was doing, I was productizing myself, my value.
• 28:34
  And I proved what needs to be built. And that gave me first customers and the product. So that's one of the options. Because sometimes a job can be a distraction. And honestly, I do see how people essentially quit the startup because they cannot let go of a job.
• 28:55
  And it is a trust fall. You have to go all in. And I would say go all in for six months. Okay, you run out of savings, then go back to the job. Well, this was like a year and a half. Okay. No, no, no. Then, yeah, yeah. So for context matter. So sorry, this was a year and a half in. He is a product guy.
• 29:15
  And if I had known him when he first started, I would have told him, you better get good at sales because that's the most important skill that a founder can have. But he didn't know me when I started. Okay, no, wait, wait. Then you can go. I know you have a comment. But he was a product guy. He was so obsessed with product. And he's like most developers who think that if you build it, they'll come. And that's not the case. You have to build it. Then you have to market and sell the shit out of it. But he focused on product. And then like a year and a half later,
• 29:41
  He's like, I want to rethink this whole thing. I want to learn how to sell. I want to learn how to market. And I know the areas that I have to upscale myself in. And he's like, I don't have enough money to do this for six months learning this stuff. So this is like how thoughtful he was about his sort of shortcomings gave me confidence that this was the right move. And I mean, like, even if it isn't the right move, honestly.
• 30:05
  the person he is now is not the person who's obviously going to make something successful. So I rather give him the best chance of being successful by learning those skills and taking a little bit of stress off of his plate with like a salary. But yeah, I mean, sorry, what were you going to say? Two things. I wanted to talk about, first of all, it's really nice of you to think about him. And that's what I really love about you. In addition to like you being the top notch at what you do, when you and I talked a couple of weeks ago, a month ago,
• 30:36
  You gave me a similar advice. Take your own time at things. Maybe don't go all in on raising money. Date your investors so you move at your own speed. Focus more on the profitability because I personally, I really love being profitable and being independent. And that is an unusual path in venture capital. So after our conversation, we're,
• 31:00
  I already felt in that direction. And we had our internal meeting and we decided that we're gonna see strap at least this year. And we're gonna date and see when a really great leader partner comes in with unfair distribution.
• 31:18
  That would just make sense. They invest $3 million, but it's like they bring at least five in revenue because of their distribution. And that's why now I'm accepting checks from angel investors who are famous. We accepted a check from you yesterday, another check, and a third check from a very famous content creator with her business. So those checks I will be accepting at any time because...
• 31:44
  It is like, I don't care about your check that much. What you're giving is so much more. So like content creators, famous people who give distribution, that is more important than a venture investor who writes me to a million dollar check, but I still need to figure out distribution. I fully agree with that.
• 32:02
  Yeah. So like our conversation and your focus on like what is comfortable for me, what is good for me is so good because you made it clear if I'm not doing well, startup is not doing well. So I think your advice to that guy was absolutely correct. And I appreciate you for that.
• 32:17
  I mean, it's based on my own experience. So everything I've accomplished in life has not been done slowly, but been done carefully and respecting like me as the founder, like even the podcast. So...
• 32:32
  if we can't hit, I'll give you an example. Like if there's an advertiser that wants an aggressive turnaround on something, it's going to like max out my team. They're all going to be stressed. Then all their quality of work is going to be shit. They're not going to be able to edit the podcast as well because they've like stayed up till four in the morning, trying to turn this thing or like, we don't want it. I don't want it. Like I'll always make more money playing the long game. I'll always make more money playing the long game. I'm never, ever worried about short term. Like,
• 33:01
  I don't know. I feel like some people, like you have to have two, you have to hold two ideas at the same time. You do have to move quick and you have to be aggressive, but you can't do it. By burning yourself and everyone else. Exactly. So you have to understand your own pace and your own comfort level too. I really think that's important because if you go, like the company's gone.
• 33:25
  And I think that there's a select few people that can, I don't know, maybe outwork, out-hustle, sleep less than everyone else. But majority of people, they're still human beings. They're not all like Elon Musk at the end of the day that can play Dungeons & Dragons while being a trillionaire. I think the average person has to respect their own limits. And that is sort of counter to this hustle culture narrative you hear about online. But again, if any founder just stays in the game for 20 years
• 33:53
  And it doesn't mean that it's 20 years of things that don't work. It's 20 years of iterating and improving and ideating. And if you learn about some of the big companies that we know of today, they didn't start the way that they started. If you ever want to know a really cool example, the story of Slack is a really cool example of a company that did not start out as a messaging company. Rather, a gaming company that turned into a messaging company and now obviously had massive success. But if you can stay in the game long enough, you don't burn out, you don't quit.
• 34:18
  I mean, you'll find a way to win. I genuinely believe that is the best advice for the majority of people on earth if they want to be founders. Find a way to stay long enough in the game and you will win. But the point about raising money, it's when you raise money from the wrong people or sometimes even the right people
• 34:38
  like there's now a clock on that money. So if you raise from, because keep in mind, everything is driven by stakeholders. So if you raise from angels, well, there's less pressure, but if you raise from anything other than an angel, well, now they have stakeholders. Like nobody is, so for my money, I'm responsible for my money and maybe Gina, but like outside of that, it's just, it's just my money. But if you raise from VCs, well, then they have like LPs and they have to show return. So all of a sudden now your clock is sped up.
• 35:05
  And this is the issue, by the way, with public markets. Sometimes companies make bad decisions based on hitting quarterly returns and quarterly numbers. Are you talking about the SPACs, the new glasses? Oh, that's, yeah. Well, that's a whole other thing.
• 35:19
  Oh my God. I think it's almost like 20% down. And they've been working on those for 10 years. By the way, that's not a good example of taking a long time to build stuff. I feel like they should have taken five more years. Those glasses are wearing him. I'm like, dude, your ear is screaming for help. I don't know how. I feel so bad for him. He's been... He's such a nice guy, but I'm like... He's been working on these glasses for 10 years. He had them. He had them like... He was announcing them for Meta.
• 35:47
  had their glasses and Meta, like they partnered with Ray-Ban, they killed it. He spent 10 years on these specs and we're talking about Evan Spiegel and Snapchat and my God, they are so bad. And I think what's even worse is, I mean, the market's reacting, literally snap stock as we record, this is down like 20%, but what's worse is like nobody in the company told him that they look like horrible.
• 36:12
  And the story, it's like SNL episode. He's talking about how it's easy to wear and how with these glasses you can be more present. And I'm like, dude, easy to wear. Literally, these glasses are wearing you. And how do you become more present by wearing a computer on your head? It's just like...
• 36:35
  I thought it is not real. I thought it's truly like a joke or something. And when I'm like, and I was laughing for two hours. Shareholders are very mad. Yeah.
• 36:47
  Anyway, so, yes. And the second point that I wanted to make, sales are so important, right? Yes, yeah, yeah. Okay, so even with building for 10 years, I sell before I build. If he ran an ad showing these glasses and whether people are buying or commenting before he built the glasses, I think he would get the honest feedback and...
• 37:10
  And maybe he would pivot. I don't, like, that is my principle. I love sales. And I think that's how you stay long enough in the game. YC says, do things that don't scale in the beginning. Right.
• 37:24
  Your product, you can have humans do that. And I always do things I sell. I do with hands manually. And only when it scales and when it becomes obvious that we cannot have humans do that, only then I build the product. And like, I don't know, maybe hardware, obviously it's harder. But still, knowing that the shape is not shaping, you know, it's just like it's not looking good.
• 37:54
  Test runs with ads. I don't know. HubSpot is a success story partner. Now, customers are using traditional search less and less to find the businesses they want to buy from. Now, when a buyer or a customer asks AI for a solution like yours, does your business come up? They're looking for a product. They're looking for a service. And they're going into some AI chat tool. And they're saying, hey, help me find the best one. If your company isn't showing up, you're missing out. And most companies have no idea if their business is showing up or even how to show up.
• 38:23
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• 38:52
  I'll be honest with you, I am terrible at eating well when my schedule gets packed. I'll look up, it's 2 in the afternoon, I haven't even had a real meal, and then I'm just useless for the rest of the day because I'm hitting a wall. So I started keeping Huel around. It's been an absolute game changer. They just launched into Target stores nationwide, which is huge. You can walk right into your local Target right now, grab the Black Edition ready to drink and the Daily Greens ready to drink.
• 39:13
  The Black Edition, this is a full meal, 35 grams of protein, 27 essential vitamins and minerals, no artificial sweeteners, gluten-free, and it's under five bucks. I grab one of these in between recordings, done, I'm good for two hours. And the Daily Greens is more of a health thing. 42 vitamins, minerals, and superfoods in one bottle. It's developed by a registered nutritionist, 25 calories, four grams of fiber, and one gram of sugar. I'll have one first thing in the morning. It's the easiest win of my day. Now,
• 39:35
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• 39:51
  and I didn't for years, and that is most of our money stories, right? When we first start our career, we have one income and one account, and you can kind of wing it. But once you're running businesses, once you're investing, once you're carrying 50 different subscriptions that you stop paying attention to, winging it gets super expensive. Monarch fixed that for me. It is the personal finance app that tracks
• 40:10
  everything. So that means accounts, investments, savings goals, spending all on one screen. The first week I had it, it fired recurring charges I'd been paying for months without realizing. And every single week, the AI recap tells me if spending spiked, if my net worth moved, and what bills are coming. And I can just ask it, hey, can I afford this trip without touching my savings? And I can get a real answer based on my actual numbers. It is a financial advisor in your pocket. It costs less than an hour with a real one. So write your own money story with Monarch.
• 40:37
  Use code success at monarch.com and get your first year of Monarch Core half off at just $50. That's 50% off your first year at monarch.com with code success. I want to understand where you got this sort of strategy from, but just to bring it back so people understand your journey. So going from startup, you made it to Cooley. This is sort of like the top of the mountain for a startup lawyer. After Cooley, you left and this is where you started Lexi.
• 41:02
  I was running my agency, tech-enabled law firm. I called it Lawlays. I didn't have investors, and that's how I validated it. That's how I made money, validated everything, and decided to disrupt myself because I guess I have that tendency to do it every two years. Yeah, but I think you're not giving yourself enough credit. So you disrupt yourself, but it's not like you're disrupting yourself to build something less than.
• 41:27
  No, I always take bigger risks. As a poker player, I frequently go all in and I'm playing aggressively. That's how I think in life. I'm also taking bigger risks. And maybe at some point it will change, but that's just my nature. And the bets, when you bet it on yourself, on your strengths, knowing your strengths and you're doing what you love,
• 41:55
  and there's a combination of what the world needs, like ikigai, then it always works out. So you go up and you're taking bigger risks, but you're at a different point. Christina in 2014 took the biggest risk.
• 42:11
  Right. Because I didn't have a lot of things built in around me. Now, although monitor, it's much bigger risks, but it doesn't feel like that. It still feels scary, but compared to what I already accumulated.
• 42:25
  Well, it's because that person, current Christina, taking a risk is the most well-resourced, well-connected, has the most pattern recognition. So it's a risk, but objectively, it's actually less risky because of how experienced you are.
• 42:43
  I've had this conversation with people, not people going into their founder journey, but people that are trying to figure out at a later stage in life, like how to transition into a new career or like just do something different with their life after they've worked in a company for 30 years. And it's always funny to me because that's when they're most scared to take a risk because they have been doing something for so long. It's their whole identity. But like, no, you're wrong. Like.
• 43:03
  All the skills that you stacked over your life make that 50, 60-year-old person like the perfect person to take a risk because the chance of it working out is exceptionally high. And it's also why the startup founders that have the highest win rate are actually not the Stanford dropouts. They are the ones who work in an industry for 20, 30 years, and they identify a problem, a problem that no one else outside the industry will ever be able to see, and they build a solution to that problem. That's the highest win rate.
• 43:32
  I love that. And that's actually the thesis of my lead investor. So I took venture money and I took at the end of last year and it allowed me to make a bigger bet, stop sales for six months, build the product. And that's her thesis as well. The counsel, Amber Illick, she invests in first builders.
• 43:50
  Not the fancy dropouts who are very young, but those who have 10 years of experience in high growth companies and they know the maze. They know where the problem is, like they're an insider. But on the other hand, I'm going to tell you why those people are less likely to take risk. And I experienced it by myself.
• 44:09
  Essentially, with the law firm, I left like a million a year comfortable life again, like seeing like how I left Russia, like I love that. And when there are challenges, which is inevitable, I remember I was sitting on a product call with my head of product and ops, and I almost had a breakdown because the team couldn't figure out this thing with the document generation that for me is just like...
• 44:31
  come on, if I sit down for a week, I think I would be able to figure out. And I'm like, but if you're really telling me we can't figure out, what am I doing with my life? Like, we all have better things to do. Like, she can make more money, I can make more money. And that was the moment I stopped, like, oh, it makes sense why some venture investor bet on very young people because they have nothing better than this.
• 44:57
  I have something better than this bullshit going on. And it was just such a reminder. First of all, I understood why venture investors do that. And second of all, it reminded me to have that mindset of Christina in 2014. I still use my version of me in 2014 as my biggest inspiration because Christina sleeping on a mattress and studying for the bar exam on the floor had nothing to lose.
• 45:25
  And that is a helpful mindset to keep in mind because otherwise you just might quit because you really have better opportunities. Like more money, immediately less discomfort, less pain. You want this pain to stop, right? It's very interesting because then that means that the founder with the highest likelihood of success is somebody who has the experience. But they just wouldn't do it. But yeah, but they just won't do it. Yeah. Yeah.
• 45:54
  I just... I even have goosebumps because it's true. It's so... I just interviewed Ronan Harari. He's the founder of Spin Master. He's a Canadian guy. I think he's well worth over a billion at this point. Very successful dude. He like created and brought to market like every single brand of toy that we played with as kids in North America, at least. You probably have a version of it in Russia too.
• 46:22
  He was just writing a book called No Experience Necessary. And the whole premise of the book is actually it's better when you don't have experience because you don't have the knowledge and the baggage and the weight of life. So...
• 46:40
  Like if you're a 40, 45, 50 year old founder and you know what a good salary is like and you know what nice trips are like, then every day you're just eating shit, remembering that life could be a lot better. It's like it's very hard to keep going. But at the same time, you're the one who has the highest likelihood of succeeding. It's tough. It's very tough because like then what's the answer? Well, people, I think the answer is.
• 47:06
  Even if you had a good life, if you did it once, know that you can do it again. You just got to eat shit and get rid of your ego for a period of time. But you have the highest likelihood of succeeding if you have that experience. And if you really have that burning desire, I think if you're not uncomfortable staying in where you are, you shouldn't start a company because it's going to be really hard.
• 47:29
  So you left Cooley. You basically built this service company, this AI legal services company. Then you disrupted yourself. And this is where Lexi started. Yeah. And what was the premise or the thesis behind Lexi that you were trying to solve for in the market? And you were figuring out this thesis through your content? Through my content, but also running my law firm. Because I was one of the first AI law firms on the market. What do you say AI law firm?
• 47:59
  Yeah, it's basically AI law firm is when you have an agent running operations for you, document preparation, drafting, and some AI law firms there just let run everything through AI. Those didn't survive it.
• 48:16
  They're already gone because the quality is very low. It's 13.3% accuracy for fully autonomous AI native law firms. So for me, what it was, I was automating onboarding, CRM, client intake, engagement letter,
• 48:33
  and then figuring out what are the needs startups have and automating those. Here are the templates, here's like all of the 10 steps in this. And I hired a product manager who helped me to automate those with existing tools like Make. And because I had that, I already knew what things need to be automated with software and with AI. But I was doing a lot of things manual and with all of the automations available at that time.
• 49:00
  And I also realized that I think now there is a second wave of legal AI and there are now a lot of AI law firms that like, this is what I did two years ago. I already know the lessons that they about to discover.
• 49:16
  And I realized that there is a spot in the market that is legal operating system, like a system of record for all of the corporate records. Right now, they're all over the place. It's your data room, it's a Google Drive, Dropbox, email, different lawyers, the cap table. Nothing is self-updating.
• 49:36
  So if you want agents to really do the legal work for you, they're not able to because the context and the documents, it's not structured. There are no knowledge graphs and they are all over the place. So agents are powerful, but only if you have self-updating cap tables and data rooms.
• 49:55
  So Lexi is that context layer with self-updating records and with AI chat that essentially underneath that is specialized agents in different areas of law with very granular skills and templates. So, for example, corporate agent has corporate formation skill skills.
• 50:18
  then due diligence, hiring. Each type of agreement has a skill subagent and the templates. So it's a very granular work.
• 50:29
  But that allows the company, when they're first starting out, they can use that system to run on it, to have the legal in order, to avoid those costly legal mistakes. They can save money and they always can send whatever they created to the lawyer, just the button and the lawyer, big lawyer reviews and approves.
• 50:53
  And then the company grows, you have an in-house counsel who joins. Like what I was in my first job, I had to manage three law firms in the U.S. and multiple law firms abroad. And I had to collect all of the records. I was running like Excel spreadsheet with like these documents are here. This is the link. This is the date. Now I'm productizing everything that I've learned in 10 years while working at big law, working at a smaller law firm and working at two startups.
• 51:21
  It's so obvious when you walk through like what Lexi is doing, um, that it's smart for somebody to use this for their startup. Obviously it avoids like, you know, huge like legal bills, but what's wild to me, like when you, when you say it, like it's missing context and it doesn't have, and it has specialized agents, but what people are doing is they're going to chat or Claude and they're saying like, type me a contract for this or, or even worse, uh,
• 51:51
  because it's a security issue, is they're, like, copying tons of company information and they're throwing it into their clod at home and they're saying, this is my... That's the context layer. That's my context layer. No, but this is what people do. This is a real, real issue. Yeah. I mean, and you laugh, but...
• 52:09
  I think it was Deloitte that was caught with hallucinated references in a PowerPoint or a presentation that somebody paid like $50,000 for. And there was a court case where lawyers were found to be using AI also with hallucination and bad references. So we're like joking like, oh, this must be the, you know, 20-year-old founder that's using Claude Felico. No. Not everyone does.
• 52:34
  Everyone's using it. And I don't think they realize that 13% is how accurate, which is insane. So obviously, don't do that. Don't just throw all of your information into Cloud and ask for a template or a resource. And I can even tell when people use...
• 52:53
  AI for templates and legal agreements. Because when you actually read through them, half of them don't even make sense. Because again, the person prompting it didn't give it context. It just said, hey, give me an agreement for, or give me a contract for. And how AI works, and this is actually the biggest issue with AI, is,
• 53:15
  AI, when you give it a prompt, it's like a decision tree. It has like trillions of potential decisions that it has to make based on what you're telling it. So it has to interpret how you want this thing to end up. And without context, most of us suck at communication.
• 53:32
  Forget AI. Most of us just suck at communication, period. We always suck at communication in corporate environments, in meetings, on phone calls. We just suck at communicating ideas to other humans. But now we take those same shitty communication, whatever, lack of skill sets, but like lack of skills. And then we try and communicate with AI that has a trillion different options and no context. And we wonder why it doesn't give us a good result.
• 53:57
  And if it's like a tweet or maybe like an image, it's not going to ruin your company. But if it's a legal agreement that you're trusting the AI, well, yes, it can ruin a lot. So I just find it so interesting that we were so quick to outsource all this white collar work and legal work to AI. Like the second it was available, people tried to get it to. Because it makes sense because it's very expensive.
• 54:26
  And it takes a long time. So we have some clients who switch to us from big law firms, not because they can't afford, but because they are not willing to wait. They are on a timeline. They need to lend this contract. They want to get it fast because they're running out of money or they want to close the customer.
• 54:45
  So it makes total sense. Like as coming from Russia, I see that legal system is a monopoly in the U.S. And this is the first time that it's been disrupted. It's just what founders don't understand is that it is frequently not accurate. And one thing to remember, even lawyers don't make documents from scratch.
• 55:08
  I never make documents from scratch. Only maybe board consent, board minutes. We always take a template that was built in big law, not even like other law firms, because that template was tested like 20 years. Yeah.
• 55:24
  It was built. It's like each template costs like tens of thousands of dollars because some of the provisions, it's like it was built by many specialists who have 20 years of experience in IP, employment, commercial. So that's the thing to remember, generating your own documents from scratch. It will always be a bad idea. Again, unless...
• 55:46
  It's a very unique type of the agreement. But even then, I always start from a template that is closest to the situation because someone put the effort and thought everything through. Like legal is actually very complex. And when the decision-making tree for a simple grand stock issuance, for example, to you, like to advisor,
• 56:09
  It's like a page of things. First of all, do we have equity incentive plan? Then stock or stock options? For stock options, we need 409A valuation. For stock, what should be the fair market value? Does the board decide or do we need the 409A valuation? Okay, how much money we raised? All of those things...
• 56:29
  have to be thought through. So the founder might see one agreement, but the decision-making tree is intense. Well, this is the other thing that you mentioned to me that actually was like a holy shit moment was AI doesn't know what you want the outcome to be.
• 56:48
  And that to me, it hit because I've been part of many negotiations. And this is the thing that I don't think people understand about law, especially when they're first time startup founder, is it's not right or wrong. Yeah, it depends. It depends. And I think that's hard for people to understand. You have to know what do you want the result to be.
• 57:08
  If you want to get a deal done, well, you're not going to get everything that you want. You're going to have to make concessions. And I've seen so many deals get completely fucked because one lawyer or basically, yeah, one lawyer who's getting paid did not understand that we had to get this deal over the finish line. And they did like you gave me an example before of.
• 57:30
  you know, a 13 page vendor agreement or contract agreement or contractor agreement, I think. And Claude gave 15 pages of feedback and redlining it. I mean, that happens with shitty human lawyers, too. The point is that if you're going to do that,
• 57:47
  If I gave a 15-page response to a 13-page contract, any real lawyer would be like, Scott, excuse me, what the fuck are you doing? This is ridiculous, right? This is not normal. So I think that people forget that you have to understand where you want this thing to go, where you want the deal to go or where you want the agreement to go or what you want to have happen and the outcome is...
• 58:11
  And you have to understand the consequential things. But AI doesn't get that. Unless you tell it or have a context layer or exactly. The quality of the prompt matters so much. So when I draft things, um, we put prompt into skills. That's why now when I communicate with Lexi lawyer, it is, it's really good. Even if I'm like fix it. But before that I spent three hours, uh,
• 58:36
  like outlining what grade looks like, what other things need to be checked. So if you don't use Lexi with skills, when you're using Claude or GPT, make sure the prompt is, you know...
• 58:51
  significantly developed that it knows everything that it needs to check if you just give a generic uh prompt and especially if you are saying that oh i'm concerned they're taking advantage of me like it they do take advantage of you you're absolutely right and those 13 pages when you first started lexi uh
• 59:16
  Were you ever concerned that building a personal brand would hurt the company or scare clients off? Because I ask that because you use it so strategically and you're so good at it. Like some of your reels, like you're hitting like three, four, five, 10 million views. Like obviously. Yeah. The maximum was, I think, like 10 million. It's just popping off. It's doing very well. Yeah.
• 59:38
  all of my lawyer friends and all my friends in finance, like they do not touch social media. They do not touch it. And I always give them a hard time. I'm like, you are missing so much opportunity. Don't tell them the secret. Like, let's just keep it while we're in.
• 59:54
  And serious, right? Like, they're so scared. They're so scared of social. And now I think they're coming around. I mean, now I see some big lawyers that kill it on TikTok. And I just had John Morgan in that chair from Morgan & Morgan. Obviously, he was there like, what was it, like four days ago, three days ago? So now he wrote a book and now he's doing a whole bunch of podcasts and obviously lawyer. But...
• 1:00:21
  I don't see a lot of them on social. I have good friends that work for, you know, JP Morgan and every big finance firm. And I'm like, why don't you just post more? Post more like wealth tips or... Well, first of all, it's not allowed. I know it's not allowed. I don't get why it's not allowed. Well, why can't you do anything? But so... Cooley didn't allow me to do it. Why not? Because it's a liability without...
• 1:00:49
  huge ROI. Coolies of the world, JP Morgan, they have enough work. They don't need the stop of the funnel. They have brand. So building brand matters more for people and companies that don't have that strong brand. Like at Coolie, for example, we were rejecting clients. Like I couldn't even bring a couple of clients because we had more that we can chew.
• 1:01:14
  A partner in Miami who is my mentor and friend, and we were walking the other day, and he's like, unless it's a warm introduction. I offered him like, hey, Derek, let's come to my podcast. He's like, oh, no, I don't want new clients. Unless it's a warm introduction and it's a feat, I don't want. So like top-notch professionals, they don't even have capacity for. So this is why they don't care about it.
• 1:01:40
  They don't care about it. And second thing, I think stigma. I personally felt it, that it's cringe. And if you are top notch, you don't go to social media. Only almost like losers go to social media. That is the stigma that I had. Like great professionals don't go there. And once I had a Cooley partner when I was at Cooley, she said something like, oh, if you want real legal advice, you don't go to YouTube.
• 1:02:09
  And I'm like, yeah, I understand if we're doing, I don't know, a couple of billion dollar M&A. Yeah, we don't get the advice from YouTube. But I think for startups, it totally makes sense. I feel like that's so out of touch. It's so out of touch. It's like even with his glasses. Yeah, 100%. And you know what? Like legal is going to be disrupted and finance will be disrupted.
• 1:02:33
  The robo-advisors, when they were just starting out, everyone was like, oh, no one would buy stocks on their phone. I'm like...
• 1:02:42
  Look at Robinhood. Exactly. And now go look at, go look at, I mean, besides the fact that if you just put money into the S&P 500, you're going to beat most financial budget. But before you had to call to the broker like, hey. I know. But now like you have, there's a company Autopilot and all it does is it copies like major traders. So you literally put money into your Robinhood account, I think, and then it like, it just copies the trades they make. You don't have to talk to anybody.
• 1:03:06
  Yeah, that is a dream. So that's what with Lexi, that is my dream that before it was not possible. You like talk to lawyer, email, there's so much happening. I believe that Lexi will be part of the tech stack of every company in the world. It's like that legal operation system that tells you, hey, these are your agreements you have. This is what's running out.
• 1:03:31
  This is what you need to renew. This is the compliance thing you need to register with that state because you just onboarded that fifth employee in California. This is you promised equity. You need to issue. Do you want to activate that workflow?
• 1:03:46
  That is only possible if you build that knowledge graph and context from the ground up. It's really damn hard to build. But I think that's where it's going. Then right now I do legal stuff on my phone. Startup launch workflow I do on my phone because we built it. It took us a year to really nail down that workflow. But now I click approve, approve, approve literally on my phone.
• 1:04:12
  I think that, I don't know, the lack of understanding of how young founders like to work, and also with tools and softwares and platforms like Lexi, I feel like all of these legacy industries are gonna be completely fucked. They're gonna, yes, at this point, they have too many clients coming to them,
• 1:04:36
  That won't always be the case if they don't modernize. But you know what? It's like they're not going to modernize because I don't know. Like founders always ask. No, do modernize. Join, like, join Lexi. Well, you know what will happen? The winner will be the one that acquires Lexi if you ever choose to sell it.
• 1:04:53
  One IPO. And I don't think for us selling to one law firm would make sense. I think it would destroy the vision because we want to democratize legal access. If one law firm buys us, one law firm cannot provide all of the legal services in the world. So I think the platform approach, that's the biggest thing. And I'd rather have all of the law firms run on Lexis so when the client comes, they can add whatever the law firms they want. And-
• 1:05:20
  The law firms, even if they're not modernizing because that's not their job, the lawyers are more conservative for a reason because their mission is to protect builders from getting screwed. So for Lexi is the mission to unlock that friction from founders, but for lawyers to give them a safe space to review things and to protect the builders. So it has to be both sides that has to work out.
• 1:05:46
  I like that. I like that you have this really strong vision because at some point, if this goes well, you will have somebody that will try and buy you because they want to be the ones that modernize it and they'll modernize through acquisition. This is how legacy always try to monitor. It's so funny when founders come to me and they're like, hey, I'm building this.
• 1:06:06
  But I'm scared because like, won't company ABC in this industry just build it and set it? I'm like, no, companies don't do that. Companies suck at innovating once they're a certain size. Outside of like Google or Apple or like very few companies can truly innovate. So most likely they'll just buy you at some point. That's the playbook for most companies. But my dream was to buy a couple of floor firms. I like that. Let's fucking go.
• 1:06:31
  I have a dream law firm that I want to buy. I obviously won't disclose, but I'm working really hard for that. I'm excited for you. I'm excited for the dream because that's a big-ass dream. Okay, go back to your point about the story about shit in the rooms. Yeah, if you are not willing to deal with shit, there's no pony. So you kind of have to have one to have the other. Oh, I know what I was going to ask, or what I did ask, and I forgot. If you can see if a founder is going to be successful. Oh.
• 1:07:00
  Yes. So on the first call, I could see whether the founder is intellectually sharp. You have to have that sharpness to crack that maze. But in terms of whether they're going to make it, no, because it takes some time for me to see how fast they iterate. So usually the science of a great founder that I have that conviction, they're going to make it. So they're intellectually really sharp. They iterate fast.
• 1:07:30
  And they focus on what matters, whether it's legal negotiations with investors, with employees, and focusing on customers. So the founders who try to over-engineer legal negotiations.
• 1:07:48
  That is a sign for me, likely, no. They're focusing on the wrong thing. You have to focus on legal just enough that you don't get fucked. But if you are trying to write your own legal documents and design the new legal systems and all being very elaborate, it means you're not focusing on the right thing. Why would they focus on that? Like, is it...
• 1:08:15
  I think it's a form of procrastination. I was going to say, is it like they feel comfortable focusing on things that keep them busy and they're scared to do the things that actually move the needle? Exactly. So the things that move the needle is sales and then getting the customer's customer feedback, improving the product. That's the rejection that you have to go through. I'm not going to reject you to have a call with me. I'm billing you for that. Discussing like all of this contract and how to make this or this like 50 times.
• 1:08:44
  Well, it is easier than go and get rejected by a customer. And like you need to find out whether this is a right product, right idea, right market. And some founders get attached to the idea so they're not willing to go through true discovery, whether that's the real thing.
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• 1:11:08
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• 1:13:39
  You've worked with a ton of founders. And you've worked with founders that have not. It's funny because, yes, you have to pay enough attention to legal so you don't get fucked. You can't pay too much attention to it where it takes up your whole day. But that's any part of your business really outside of sales. Like if you can bring money in, then you'll find a way. Money cures everything. It always does. But any other part of your business, if you spend too much time doing it, even spending too much time on product without sales.
• 1:14:07
  Yeah, I think like sales and customers, you cannot overdo that. Like, obviously, you need to take care of the product. And I had that situation when I focused a lot on sales and, you know, I had a lot of manual work. I had to take six months off from that in order to build what I already knew is my vision, what I needed to build. I needed to spend time on hiring, but now I'm back on sales. Yeah, but it's six months, not six years.
• 1:14:36
  Yes, yes. There's a big difference. There is a big, and I actually, although I was not selling, but we still were having customers from Instagram stories, like our first 40 customers, I was not selling. It's just Instagram stories.
• 1:14:49
  The people that don't spend enough time on legal. It's not the people that just use it to take up their day, but the people that like really just don't care or use Claude or Chat for their contracts. One thing I love about your content is it's all these horror stories. It's really, really good. What are some of the horror stories, like people that you've actually worked with? Dollar amounts they've lost or worst case scenarios or bankruptcies or lawsuits. Like...
• 1:15:15
  And I want these stories, as fun as they are, to chat about for a podcast. These are like teachable moments for a founder. So think of like two or three that really stood out to you. Yeah. There are two mistakes with 83B election. One founder didn't file it and had to pay 700K in her Series A. Say that again. With the what election?
• 1:15:38
  83B election. Oh, okay, okay, okay. So it's a form that you file with the IRS. By the way, I will give you the instructions you will have to file it. I'm Canadian, so I'm learning as I go. Yes. So when you get the shares subject to vesting, you have 30 days from the moment you got those shares, you signed that stock purchase agreement to file those. There's like online application, but it's kind of messed up with IRS. Like if your shares cost...
• 1:16:07
  0.00001, then you cannot type it in the IRS because it's too many zeros. So you have to mail it. And you have only this limited time. And it's very strict. I think my CPA takes care of this because I haven't done this myself.
• 1:16:24
  No, at Lexi, we also give you an online option like for $90 to do that. So there are different options, but founders need to know 83B is so important. There is no good fix. It's really important. It will be discovered in your due diligence. So that founder messed up, didn't do it.
• 1:16:41
  700K in Series A. She had to pay out of pocket and founders are not rich. And why does she have to pay 700K? What's the screw up that leads to the 700K payment? So with 83B, if you don't file 83B election... As the founder. As the founder. Then you get taxed every time the stock vests. So let's say for two years, the company value, like Series A, right? Like term sheet. So the company value grew. This is your tax bill. If you file 83B election, you tell IRS, hey...
• 1:17:11
  Tax me right now at the time of the stock issuance, not when the time the stock vests. And early on, it's almost zero. So you don't pay any taxes. So you pay like zero or 700K. Like it's a big difference. And that's for shares, not straight equity. Yeah.
• 1:17:32
  So shares is straight equity. It's this like equity is a term. Like if you think about company, company's cap table, it's a pizza, right? Like that is equity. When you do like a safe, for example. Safe, it's not equity. It is agreement for future equity. Option, unless it's early exercisable, it's also not equity. You need to exercise. But for early stages, so I usually do stock for the first couple of years.
• 1:18:01
  Not years, because if you grew to, I don't know, $30 million in the first year, then you need to do stock options because the stock is too expensive. So you got Lexis shares at a nominal value because right now our value is nominal. But in a couple of years when the value is high, people don't have cash to pay like 10 grand, 20K worth of shares out of pocket. So that's why stock options. Yeah.
• 1:18:30
  And for, now I'm just asking for myself, for the investor, what do I have to pay attention to when I'm investing in companies? Yes. So after you sign, for example, advisor agreement, they promise you shares, we still need to issue those.
• 1:18:45
  And that's the board consent. Companies usually do those like maybe once a month, like consolidate all of the stock issuances. So from that day, when they have the board consent, you got the stock purchase agreement, you have 30 days, they have to guide you. So if...
• 1:19:01
  They promised equity, but they never sent you stock purchase agreement or 83B election instructions. It means they haven't issued the shares. Like in our case, we haven't issued yet the shares. That's why you don't know about that form. But it's going to happen soon, like this month. So that is the form that you would need to take care of. So this is obviously something that founders have to pay attention to because that could cost them a ton of money. It can cost them. And if the issue shares, for example, I would care about you filing it because in due diligence, it's going to be my problem.
• 1:19:31
  I would have to explain that. So you have to chase everyone to make sure they file it. What are some other big issues? And that's not even like using chat or Claude to write a bad contract. Like that would never come up unless you actually work with a startup lawyer. Exactly. You wouldn't know about those things. So that's something that you need to know what matters. And for early stage startup, 83B election matters.
• 1:19:58
  Stock subject to vesting really matters. Don't give stock to everyone. Then knowing how to issue stock. If you do it yourself, so what I frequently saw, and we had a client who came to us in the middle of fundraising because the investor found out that the co-founder never had shares issued. So stock issuance, it's a board consent with like stock purchase agreement or stock option agreement. Yeah.
• 1:20:22
  Just doing the carta, you know, like that thing doesn't work. Having a founder agreement, it is a disaster. It's a bad, bad idea. So stock issuance, it is a very specific legal action that people don't realize what needs to be done there. And they sometimes we have solved. I had a situation with a solo founder who never issued shares to herself.
• 1:20:47
  She raised a million dollars. She actually never issued shares to herself because they're like, this is me. Who else owns this company? I'm like, no one.
• 1:20:57
  People don't know that. And investors don't know that either, unless they are very experienced investors. But investors are professionals, right? They manage money, someone else's money for living. They have legal counsel. And they do due diligence every other week because they invest every other week. I mean, like VCs. But as an angel, I don't know half this stuff either. I'm not telling some founder what to do. Now you're like, where's my 83B election?
• 1:21:25
  No, in all seriousness, because if you could, as a founder, look at somebody who has money and think, well, they would guide me properly. They must know. That's not always the case. That's why many of our investors, we have a couple of investors also running on Lexi and they do due diligence on our platform. That's why many investors recommend their portfolio companies, hey, run on Lexi.
• 1:21:47
  So those things you at least won't miss. And I, as an investor, have a peace of mind, especially angel investor, that you didn't mess up the fundamentals. Because certain things, they don't have a good fix and that really can mess everything up. Like 83B election, IP assignment, vesting schedule. I would say QSBS is also, first of all, being a senior.
• 1:22:11
  That's a C4 versus just like an LLC. Yes. And stock repurchases can mess up your QSBS. So when someone leaves, the way you repurchase stock is really important or you want to redistribute. You can mess it up. Explain for people who don't know what that is, like the benefits of that, because that can save you a ton on your tax bill.
• 1:22:29
  Up to $500 million. If you really maximize those benefits, it's a really huge tax saving. So qualified small business stock, it's the biggest tax break in America. Essentially, you're being taxed, exempt from federal capital gains tax, and sometimes in state, depending on the state.
• 1:22:52
  you get up to $15 million, but then if you maximize it through trusts or LLC to C-Corp conversion, it could be up to $500. So for example, I personally, I'm setting up trusts for trusts. So my QSBS will be up to $75 million. And on Lexi, for those sophisticated founders who know that this is likely going to be a life-changing outcome, they set it up on Lexi.
• 1:23:21
  They can do the trusts. I don't recommend it to everyone right away because 80% of the startups fail and you don't want to over-engineer. Do the Delaware C-Corp, like make sure it's going well. And then once you're feeling, okay, it's going, then you start doing the trusts and optimizing. One of your stories is about IP that left with a co-founder. Explain how that happened.
• 1:23:49
  Yeah. So when founders get the equity, they assign all of the IP to the company. If there is no IP assignment, the founder can leave the company, start even a competing company with that IP. So for example, if a CTO developed the platform and there is no IP assignment, that CTO owns that platform. And if they quit and you can't use it anymore.
• 1:24:19
  No, right? Because he owns it. And there are different, you know, intricacies, but that's where the litigation would come in. Like, for example, whether he was an employee, then the work for hire would work. But if he was a consultant, no, it automatically doesn't work.
• 1:24:37
  you know, get transferred to the company if nothing was executed. And that was the example with that friend who lost the company over a CTO. She hired an angel list, never signed anything. And in the middle of a financing, like a 1 million financing, that CTO asked for 500K for the IP assignment. And she's like, no.
• 1:25:00
  investors like no like would you invest a million dollars knowing that half will go to like no of course so the the but is the cto an asshole at this point or like what's is he just trying to take advantage of a a poorly structured agreement or he's like i built this yeah if you want it you gotta pay for it i don't want to like i don't want to be here anymore he was trying to have his own little exit
• 1:25:24
  For real. He was like, I don't want like I built this and I'm going to even though I've been getting paid as a CTO, this is my IP that I developed myself. Yeah. And that CTO hired a very litigious shitty lawyer on a contingency to just blackmail the founder and the investors.
• 1:25:46
  Yeah, it just... And I think sometimes people are shitty, but also sometimes when there is a conflict between co-founders, I've seen situations when co-founders become so revengeous. They're like, we're going to go down together. I'm going to take everyone down because I hate you so much.
• 1:26:05
  And they would sue, like right now, the litigation that is happening without one of the Lexi clients. Yeah, the co-founder is just very, you know, he's like in the court proceedings, like he sleeps in the car because he spends all of the money on litigation. I'm like, get off the streets. Stop doing that. Yeah, but some people are not right either. Like some people are crazy.
• 1:26:28
  But we talked about it, like founders, they are obsessed. It's a very specific type of a person. And you're either obsessed with customers and product or... You said something else. I've always said that like the habits and the personality that can make a good entrepreneur...
• 1:26:47
  That's like a slippery slope into a lot of other really, really bad behaviors because it's like pure addiction. It is like straight addiction to this game that we're playing. And I think that somebody who could be a good founder could easily be an alcoholic, a drug abuse, like just have the worst habits because they have this addictive personality. Like when they're into something, they're just so into it. So, yeah, fine entrepreneurship is like a little bit healthier. Yeah.
• 1:27:12
  But I feel like they're literally like one bad break away from spiraling out the time. Yeah, I think we definitely have some certain mental dispositions. Most entrepreneurs are, to a degree, they're neurodivergent.
• 1:27:29
  Yes. And I used to blame myself. Like, it's hard for me to have a job where I'm not passionate about something. Like, I'm dyslexic, but for a lawyer, it could be end of the world. But when I care, I don't like, I don't have it anymore. So it's a combination. Really? Yes. So when you row your bar, you couldn't read the English, but you also couldn't read the Russian. It wasn't Russian. You're just like guessing everything.
• 1:28:01
  Well, it's like intuition, but that being present, that's what helped. Yes, of course. So I think that's, but for example, like first year of my career, I was misspelling clients' names.
• 1:28:14
  I know it's like really bad because, but I would solve some hard problems, some creative solutions I'm really good at, but like, you know, typos here and there. Now when I'm building the product, I'm very obsessed and I notice every single thing. Or if I really care about the client, that this is important. But if you, I cannot force myself, like some people like to work for 12 hours on things that I don't care about. Like I physically, I,
• 1:28:43
  Like maybe I can do it, but for a short time, I cannot force myself to do something that I'm not passionate about. But when you're building something. I'm over obsessive. You're over obsessed, even though a lot of it is not fun work. Like a lot of it is work work. Like podcasting, because you're a founder, is like objectively fun.
• 1:29:08
  But a lot of the shit that you're doing at four in the morning is not fun stuff. So there's a difference between doing work. Like being a founder doesn't mean everything you're going to do is going to be fun. But you're so obsessed with where it's going and the outcome and your baby and what you're building that the shitty work is like acceptable.
• 1:29:25
  Yeah. And I think for me, similar to you, I really like building the systems and automating things because I don't like doing the same things over like three times. It's the maximum for me. So you can see how being a lawyer in a traditional law firm works.
• 1:29:41
  is really not for me because it's doing the same thing over and over again. And I'm like, what is exactly the point? And I think it's also for people now like lawyers who are graduating. If society can teach you to do something, it can teach someone else to do that. So you're not being unique. And I even had that moment when I was being taught certain things. And I'm like, if you already know how to do it, can you do it yourself?
• 1:30:07
  And that mentality, although this is a wrong mentality for an employee, right? Like this is how I teach you the skill. You take it and you repeat. I don't expect you to innovate here. You just need to keep going with that. But I just have different personality that I like creating new things that don't exist. And if something exists and works, I'm like, then why? It's not my job. I'm curious what advice. My brother just graduated law school.
• 1:30:36
  And he wants to go work. He's Canadian. So he wants to go work for a prosecutor in Canada. And he's just starting his career. But for somebody that is young, that has never really thought about starting a business, I'm just more curious because you are sitting at the intersection of AI and entrepreneurship and startup. Like for a young, ambitious person. My brother is super smart. But...
• 1:31:03
  he is on track to be an employee of the government. What's your advice to that person? If you were just going to say, even though you're so excited about the career path that you're on, how do you make it so that you can still exist and have a job in the world of AI and I don't know the future of, of work, even if you're not an entrepreneur, like what's your advice to that person?
• 1:31:31
  I have good news. For everyone who is excellent at what they do and they love what they do, they're not going to be replaced. Use all of the tools to be more excellent. AI is a tool for you to be more excellent. But people who are really good at what they do, AI makes them better. They can do more, but it doesn't replace them. One thing that I really like is the idea that everybody should act like an entrepreneur, even if they aren't one.
• 1:31:58
  Yeah, exactly. The employee, that is incredible. So I actually don't think that there is a hierarchy and I don't believe everyone should be an entrepreneur because we discuss certain traits that people have. And I was not the best employee and I was always trying to weep myself in being that employee. But it's so energy draining for me to comply with rules and procedures. Yeah.
• 1:32:25
  So for a person for whom that's natural, they can make really great money, millions of dollars, hundreds of millions of dollars by being a really great employee because it's not less important than being an entrepreneur. We cannot make anything happen unless we have those employees and we will always compensate them well. So I wouldn't recommend everyone to be an entrepreneur.
• 1:32:50
  I think yes to all of that. Not everybody should be an entrepreneur, but everyone should adopt the personality trait. Ownership. Ownership. And that's what I think people screw up. They work a job and then all of a sudden they don't worry about their career or their future anymore. They don't worry about learning new skills. They're like, I'm comfortable. And those are the people that get fucked.
• 1:33:13
  Those are always the people that are going to get screwed if they just, if they don't, because if you act like an entrepreneur, meaning like you're always learning new things, you're always disrupting yourself, you're sort of like on the bleeding edge of technology and tools and systems and ideas, you're not going to be a problem.
• 1:33:28
  you're going to be good. Like if you want to work in a company, you're going to be very good. Yeah. Very good. But you should be so excellent and so dangerous that if you got fired, you could be the person that will go build a hundred million dollar company. You just don't want to do it. Yeah. That's the personality that's going to win. Okay. I want to...
• 1:33:47
  Just ask a couple more questions that will hopefully inspire like a young generation of entrepreneurs. And also the fact that you're a woman, you're an immigrant founder, you're building in an industry that is famously old male credentialist. What's that been like?
• 1:34:02
  I definitely stand out, but I think it's a good thing. Everything that makes you stand out is your superpower and you should use it. And the brand that I built, Lexi, it's a new, modern, it's like appealing brand. And I represent that brand. I think there is definitely a desire for something less stuffy, something that...
• 1:34:26
  AI powered, just like technology empowered, but still has humanity and human touch. But in a way that feels like a conversation versus there's a smart person who is all tied up in a suit. So I think
• 1:34:45
  Yes, it is a very conservative industry, but it helps me to stand out by being myself. Because authenticity is what stands out on social media. It's what attracts people. And you want to attract like-minded people.
• 1:35:01
  Do you realize that everything that people could say, well, that's a reason why I can't do it. You take it and you're like, oh, that's the reason why I can do it. Because I'm a girl that sees the shit and is like, there's a party here. There's a party here. Oh, it's every single thing that could be like a negative or something that would totally make you stress about starting or something that, you know,
• 1:35:23
  I'm not American. I'm not a man. I don't have like 50 years of experience. I'm going to go on social media. I'm going to move to a new country. You look at every single negative thing and you reframe it. You really do.
• 1:35:39
  Actually, that is true. I didn't know. It's not something that I even think about. But you do it. Yeah, I guess so. Yeah, it's not something that I do... Consciously. Consciously, yeah. And I never felt that I'm at a disadvantaged position. Although most of my investors are women on the cap table, I never targeted women.
• 1:36:00
  I just got recognized, create and cultivate 100 list. And it was 100 powerful women. And I'm like, wow, there are so many of us. But even like whether it's a man or woman, I feel greatness in people. I feel greatness in you. And gender in that sense doesn't matter. So when I hear people say like kind of like that victim mentality,
• 1:36:27
  Like it's a self-fulfilling prophecy. If you're going to say that, that's just going to happen. And I don't know whether I was discriminated or not. I do have to deal with things that only women probably have to do, but maybe gay men as well.
• 1:36:44
  someone like hits on you and you need to navigate that. Like, I want this business partnership, but nothing is going to happen between us. So that I think I do need to navigate. But even that, like, I use it to my advantage. You like me? Like, well, guess what? We're not going to date. You can invest in my company.
• 1:37:04
  Not invest, but investors actually don't take. Like someone who likes me, but not the company, I don't take. Because that's just going to be a pain in my ass on the company. I never said that's going to be a pain in your ass. That's fucking funny though. But for business partnerships, I want you to be on Lexi platform. And I set the boundaries. A bad man don't have to like...
• 1:37:31
  go with that. Like on some meetings, I bring another person because I'm like, I don't know. You read The Power of Now and you read Dune and you speak about these two books. So what do these books have in common for you?
• 1:37:48
  So power of now is about being present and aligning with that power and that everything comes from it. And I think dune, there are a couple of things that really stick with me. One is that every dream is a seed that was put in your consciousness and it leads. And on your path, you're going to face fear. And I really love the...
• 1:38:14
  The part of the dune, fear is the mind killer. It brings, fear is the mind killer. It's a little death that brings complete obliteration. I will face my fear. I will let it go through me. And when the fear has gone, I will see its path. There will be nothing. Only I will remain. I love this. What is the, what is the tattoo? Yeah.
• 1:38:39
  I mean, it's logo. Lexi logo. Was there a reason why?
• 1:38:47
  Yes, I've read the book Recruiting Creative Act, The Way of Being. And I have a couple of tattoos on my body, like three tattoos on my back. And they mean like my reminders. And this is a reminder to create, just like put it out there to never forget to create. And the reason why it became Lexi logo is that in the center is always a founder with a vision.
• 1:39:12
  And that's how everything starts. It's the inception point. And it's also target, focus on the consequential things. Like everyone who sees that has their own meaning. Like everyone has a different meaning. It's just the sun. It's the, you know, the plane. Like so many meanings. That's why I love that.
• 1:39:34
  I asked because I knew you before we sat down, but now after like really speaking to you for like two hours now, I feel like nothing you do is just by chance. You're very purposeful. Where can people find you, connect with you, follow everything you're working on, follow Lexi? We'll put like links in the show notes, but where do you want to send people? I think Instagram, LinkedIn would be the best and Lexi.ai. What's her Instagram?
• 1:40:03
  Christina Subatina, ESQ. So it's like a little long. ESQ is for lawyers. Esquire. Esquire. Yeah. The last thing, if you could take all the wisdom you've learned over your entire career and you could go talk to that Russian immigrant in 2014 that really just came here with a suitcase and a lack of understanding of the English language, what would be all the wisdom that you would tell her?
• 1:40:33
  Or the most important piece of wisdom that you would tell her? Yes, you can. Trust yourself.