Leadership Capacity with Hilani Ellis
Leadership Capacity is a limited conversation series with founders, CEOs, and executives who know firsthand that as companies and teams grow, leadership has to grow with them.
Hosted by Hilani Ellis, each conversation brings forward the experiences, decisions, challenges, and lessons that have shaped how accomplished leaders lead today. From building companies and developing teams to navigating change and preparing for what comes next, Leadership Capacity gives curious leaders a closer look at what leadership requires when responsibility grows.
Leadership Capacity with Hilani Ellis
From Building a Law Firm to Advising Founders: What Shawn Stigler Learned About Leadership (E: 002)
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Shawn Stigler has spent more than 25 years working alongside founders, executives and investors through some of the most important moments in building and growing companies.
But Shawn hasn't only advised business owners. He's been one.
After starting and growing his own law firm, Shawn eventually joined Michael Best, where he now serves as Managing Partner in Colorado. That combination has given him an unusual perspective: he's experienced the responsibility of building a business himself while also having a front-row seat to hundreds of other founders navigating growth, people, risk and change.
In this episode of the Leadership Capacity Show, I sit down with Shawn to talk about the patterns he's noticed along the way.
We explore what actually builds trust, why reputation matters, the difference between being excellent at your craft and leading people, and what founders often experience as their companies grow beyond the early stages.
We also get into the future of professional work. Shawn shares how AI is already changing the legal profession, what he believes young lawyers should be learning now, and why he sees AI as a leverage tool while human judgment and conversation continue to matter.
In this conversation:
Building a law firm and learning the business behind the profession
What 25 years around founders teaches you about recognizing patterns
Why reputation and trust remain so important
The shift from being great at your craft to leading other people
What leaders are really optimizing for when making decisions
How AI is already changing legal work
Why young professionals should become students of AI
What Shawn is seeing from today's founders and startups
The inflection points that change what a growing business needs from its founder
What Shawn would tell his younger self about taking chances
Leadership Capacity is a conversation series with CEOs, founders and experienced leaders about what leadership has actually required of them—and what they've learned along the way.
New conversations every Tuesday.
#Leadership #FutureOfWork
00:00 — Preview
00:42 — Meet Shawn Stigler
01:55 — Shawn's Path Into Law & Entrepreneurship
05:37 — Building a Law Firm & Learning From Founders
10:12 — What Actually Builds Trust
17:06 — Being Great at Your Craft vs. Leading People
22:46 — How AI Is Changing the Legal Profession
25:34 — Is There Still a Future in Law?
27:37 — What Shawn Is Seeing From Founders Right Now
31:11 — The Patterns Founders Repeat as Companies Grow
34:30 — When Growth Changes the Founder's Job
35:32 — What Shawn Would Tell His Younger Self
Michael Best: https://www.michaelbest.com/people/shawn-stigler/
Shawn Stigler on LinkedIn: https://www.linkedin.com/in/shawnstigler/
Grab the Leadership Book: https://www.hilaniellis.com/hilani-ellis-capacity-the-new-advantage
Subscribe to Leadership Insights: https://www.hilaniellis.com/
Follow along on LinkedIn: https://www.linkedin.com/in/hilaniellis/
On the way here, I was talking to my wife because we're getting our tax info together. Uh-huh. And she's like, I don't know how you ever did this. I don't know either. I don't know either. As a lawyer, I'm not answering your question, but um your reputation is everything in this world. Doing what you say, saying really showing up. Be the best AI, yeah, like student you can possibly be.
SPEAKER_01Absolutely.
SPEAKER_03More people have access to that.
SPEAKER_01Leverage tool for sure. Totally. Well, it's trying to find its place. People still gonna are gonna want to have a verbal conversation with a human being.
SPEAKER_03Exactly. You kind of just like get locked into comfortable.
SPEAKER_01Yeah.
SPEAKER_03And you're like, you know you're not happy, or you know this isn't who you are. And it's like rip the band-aid.
SPEAKER_01Sean Stigler, great to see you.
SPEAKER_03Hello, Helani.
SPEAKER_01Uh, you've spent 25 years helping founders, executives, and investors navigate some of the most important moments in building a business. Uh, but what interests me most isn't the legal work as an attorney. Uh I learned a little bit, accounting as well in your background. It's the perspective that you've gained from having, which I can personally relate to this, that front row seat to hundreds of leadership journeys. Um, for most leaders, you know, they only experience one company. You, uh similar to me, yeah, have seen the inside of so many companies and guided leaders uh to create compelling businesses, if you will. More often than not. Yeah. And so uh you're high performer. I I love the way that you work. It's been great knowing you for the years that I have. Um, welcome to the leadership capacity. Oh, thanks for having me. Yeah, thank you so much.
SPEAKER_03Yeah, I just you told me some of the other folks coming in even more on.
SPEAKER_01Some of the other names I've had I've got scheduled to record, which is great. Uh, some of people that we know mutually. Exactly. Uh let's start with your background. Yeah, yeah. You graduated. I just learned you did accounting for a little stint.
SPEAKER_03Which literally on the way here, I was talking to my wife because we're getting our tax info together. Uh-huh. And she's like, I don't know how you ever did this. And I was like, I don't know either. I don't know either. Yeah. Yeah.
SPEAKER_01And so then you transitioned into this legal space. And so there, and I even said this, there's a small double threat to especially when you're talking to executives, founders, helping with MA transactions. Uh, you understand that that financial side, which is so valuable. So give us that story, you know, kind of post-college to where you are here today.
SPEAKER_03Yeah, absolutely. No, I think um it's funny. I'm and we're at an interesting time again with AI and honestly. One of my questions, yeah, and all these things. It's like, what I have a 16-year-old, and it's like, what do you tell them to pursue? And such a great question. You work with so many, I work with a lot of university kids. And um I decided I decided to be an accountant because I literally this will show my age a little bit, although you already gave it up. Um, I literally went to the career services office and they used to have like clipboards on the wall of job postings. Oh, sure. And accounting had like three clipboards of job postings. Um, and you know, marketing had like half of one, real estate had like half of one. I was like, why is there so many job postings for accountants? And they're like, Yeah, there's just always a big need for accountants. Interesting. That's what I'll do. That's where I'll go. Um and this is like the advice I would give, I do give my son, and everyone else is like, don't do that. Yeah, because I was not wired to be an accountant. Um so I was incredibly fortunate, you know, University of Wisconsin had an awesome accounting program. Nice. I had great professors. Um, that's a whole nother fun story, maybe for another time. But yeah, some really great professors. Um and uh I got to work for Arthur Anderson, which was kind of a super prestigious firm at the time. Yeah. And um, so yeah, I did that for like three years in the Midwest. And it was a really interesting group at Arthur that um worked with privately held large family businesses. So people like Senator Cole or the Johnson family that owned S. Johnson or um folks of that caliber. Yeah and um it was really awesome. It was like the first time I got to really learn be in the room with all these great business owners.
SPEAKER_01Absolutely.
SPEAKER_03Um, it was great.
SPEAKER_01What a great seat, yeah.
SPEAKER_03Now you did have to wear blue or gray suits with white or blue shirts every day.
SPEAKER_01Little uniform.
SPEAKER_03Yeah, and you had to work with decision fatigue. So that's kind of nice. Yeah, exactly. It actually bizarrely was that. Yeah. Even today I was like, do I do jeans in a sport coat?
SPEAKER_01Do I wear up the phone? It's the reason that Steve Jobs always have the turtleneck. Exactly. Low decision fatigue, save the decision making for bigger things.
SPEAKER_03Yeah, nothing but respect for that. Yeah. Um, I might start migrating more that way. Um so yeah, so I did that for like three years and I learned a ton and I worked with like amazing people, but I hated it. Yeah. Um, and I was in the Midwest, which is where I was born and grew up. And I I just always loved Colorado. Sure. And so I moved here in 2000, like I didn't know a single person.
SPEAKER_01Wow. Um and I know you know so many people now. Yeah, well, amazing, especially well connected.
SPEAKER_03Great. Um, thank you. Um, but especially there was kind of this window in Boulder, kind of oh, three oh four to like 2010, when Boulder was just going parabolic and you had Foundry and Techstars and and like it was really getting its groove. And um, I just happened to be here then.
SPEAKER_01It's good timing.
SPEAKER_03Such good timing. Yeah, like I I won't take any credit for it. Um yeah, so started um I'm yada yadaing over some things, um, but started a firm called MODIS Law.
SPEAKER_04Yep.
SPEAKER_03Um, and and that was great. So we we worked a lot with still investors and family offices and people like that that looked to deploy capital. But then, like I said, you had, you know, Techstars, Foundry, all that ecosystem was blowing up. And so did a lot in that world too with the startups. And I just loved it. Like you kind of mentioned we've both seen a lot of founders and executives, and I think truthfully, I I mean, I started my own firm, but I maybe didn't have the guts to like start an AI company or start a food company or something. But doing what I do and to a degree what you do, right? You get to live a little vicariously through that energy.
SPEAKER_01So fun. It's so fun. So fun. Having worked with Bradfeld, so fun.
SPEAKER_03Of course, yeah, that's right. Um, so yeah, and you get to learn. I mean, people are so wide-ranging and diverse in what they bring to the table and how they run a company and and watching them make decisions.
SPEAKER_01And then it's like, ooh, I really want to know why you made that decision. Or I want to know also why you paused longer than normal to answer that question. Uh-huh. Uh so yeah, it's watching patterns, having those conversations. Yeah. Yeah. It's fantastic. So awesome. So then when you started Modus Law, which then in 2018 joined Michael Best, which is where you are now. Exactly. As a managing partner. Yeah. Okay.
SPEAKER_03Fantastic. Yeah. And that, yeah, that was great. I mean, we grew, we had just a great team. It's so funny. We started in the Spruce Street Mansion in Boulder, which a lot of people will know. And it was this old building. It was so fun. So great.
SPEAKER_01I love historical architecture.
SPEAKER_03Oh, and I think we started, it originally was called Stigler Wusso, started with this great guy, Mike Wusso. And um, I think we we subletted from a guy initially, and I think our total overhead was like $500 a month. Nothing. Maybe $600. Yeah.
SPEAKER_01Oh my gosh.
SPEAKER_03Um, and it's funny. I know you're gonna talk to Matt Fargo.
SPEAKER_01I am.
SPEAKER_03Hertz Fargo was literally kitty corner from us. Okay. Same thing, like second story, cheap rent. Um, and that was like that was kind of that good Mojo Boulder at the time. There's so many. And you'd walk down to Tiaco and get tacos and the bed. Yeah, it was it was really magical. Yeah. Yeah.
SPEAKER_01And so then you went back to school.
SPEAKER_03So I went for school in 2000. Um so yeah, that's part of the Yacht Ya. So you said you were gonna jump into the And I always wanted to be a lawyer. Uh a lot of ironically, Arthur Anderson, even though it's an accounting firm, was also the biggest employer of lawyers in the world at the time.
SPEAKER_01Fascinating.
SPEAKER_03I worked with all these lawyers. Sure. I was like, I want to do that.
SPEAKER_01That's what I want to do.
SPEAKER_03So um, so yeah, I went to see you for law school. It was awesome. Yeah. Um, and yeah, graduated in 2003, which was an interesting time too, because the tech bubble had crashed in 01. Is that right?
SPEAKER_01I was trying to remember the timing.
SPEAKER_03And so you had all these great firms like Cooley and Brobeck, who had just really grown here in Colorado. I was gonna say Cooley's yeah. Um, and so I was trying to get a job uh when I was competing against like seven-year Cooley attorneys. And they're like, why would we hire a first year like no history? What are we gonna do with you?
SPEAKER_01So then you just made your own thing.
SPEAKER_03Short, pretty shortly, yeah. Yep. So yeah, and then that that was super fun, but you know, owning your own business, you have cash flow, you have HR, and and um you have to scale, you know, the thing about law, especially now, you need data privacy attorneys and incentive comp attorneys. A lot of needs exactly, especially in transactions and ventures. So we just weren't quite big enough to do everything right. And um, Michael Best, I had known since I was a kid. It's it's we're a hundred years.
SPEAKER_01Aren't they out of Wisconsin? Exactly. Yep.
SPEAKER_03And it's almost 180 years old. It's amazing.
SPEAKER_01Oh my gosh.
SPEAKER_03I always tell people, like, we're older than GM or Bank of America. Yeah, there's weight to them. Right. Uh and um so it was great. And it was just kind of a quiet competence firm. Um, you know, not big ego, not fancy.
SPEAKER_01I like that quiet competence.
SPEAKER_03Oh, right, yeah. Absolutely. Um and so they really wanted to grow like a venture emerging company group. And so I spent the first five years going to Austin and LA and you know, Raleigh and all over the place growing that team, which was awesome. Amazing. Yeah.
SPEAKER_01Uh what earns trust inside a law firm that isn't taught in law school?
SPEAKER_03Oh my gosh. Um, what earns trust?
SPEAKER_01Yeah, inside a law firm.
SPEAKER_03Like to each other or to clients?
SPEAKER_01That isn't taught in law school.
SPEAKER_03Yeah.
SPEAKER_01Yeah.
SPEAKER_03So inward facing or out?
SPEAKER_01Yeah, I would say as a founder, right? And now managing partner, when you were building your team at MODIS, what was important about thinking about trust?
SPEAKER_03Yeah. Oh man.
SPEAKER_01Especially in hiring. It's a loaded question. It's a heavy question.
SPEAKER_03No, and I'm sure I did some things, you know, uh could have done better. Yeah, exactly. No, and I I still talk to quite a few of the folks. Um, I think it's similar to the advice I give um law students, which is especially in a market like Colorado, you're all gonna work together forever. Absolutely. Yeah. Yeah.
SPEAKER_01And people talk on the side. Yeah. So there's that. Yeah.
SPEAKER_03Yeah. And and um you the great thing about what I get to do and our team gets to do is it's two people trying to get to the same outcome. Like you have an investor trying to invest in a company trying to get money, or a buyer trying to buy and a seller trying to sell. So like you want the same outcomes. Sure. Um, versus like divorce or, you know, other litigation where it's like it's a zero-sum game. Um, and so your reputation is everything in this world. And you have to, you know, um, I'm doing a deal right now with a great friend, um, actually two deals, and we haven't really done anything together, like professionally. Yeah. And it's so fun to be, yeah, you still have to be like, well, this is really important. Yes. Um we need to have this. So you still have to do your job, but you can do it as a gentleman or a gentlewoman, you know, professionally. So yeah, I think um as a lawyer, I'm not answering your question, but um uh I think, you know, doing what you say, saying, you know, uh really showing up. Yeah. I think it's Jim Collins says you are what you do. Um like um, and I I think that's true. And like I said, I'm sure I could have done some things better. We were we were pretty lean at the time and sure.
SPEAKER_01Um which means you have to give out a lot of trust because I need you to cover three areas.
SPEAKER_03Yep.
SPEAKER_01Um I was having this discussion actually yesterday for another recording and trust came up. And I I start to pay attention when I you're gonna go buy a car, and so then it's the only car you see on the road now, right? Right, right. And so for me, when I hear things and all the conversations I'm able to have, I start hearing a lot about trust. And it's been happening a lot in the last four or five months. Yeah, interesting. And uh one of the things I've realized, you know, and with searches, right? Some executives like, hey, I actually don't trust easily. Yeah. So I need someone to earn my trust. I'm like, well, I'm gonna need you to give me a TED talk on what that looks like on how to earn your trust. And what I've distilled it down to is my standard of work product at the same level of your standard of work product. Interesting. And that when we know that we're within a very tight range on deliverables, because that's how I would have done it, uh-huh, I have faster trust in you.
SPEAKER_02Yeah, yeah. That makes sense.
SPEAKER_01So I was threading trust can be built when someone holds themselves to a high standard, not just in the deliverable, uh-huh, uh, which would be great for the introvert, but for the extrovert of like, what's the executive presence? How are you delivering in the capacity of this role? Can you actually go in and represent the individual?
SPEAKER_04Yeah.
SPEAKER_01Um, and that's not just with executive assistants, that's now with director of operation roles that I'm filling. Uh, because they need the executive needs to multiply themselves.
SPEAKER_03I just curious. Um because you obviously like obviously we've worked together a bunch and we have a lot of mutual friends um that even have worked now in other roles with other friends. It's awesome. Um, I can't tell you how much that comes around, by the way, but for another time.
SPEAKER_01I love that.
SPEAKER_03Um but how I mean you really have to get to know people. Yeah. And they have to because people are so different. Like how how I work with like Kat, you know, exactly very different than how Brad might work with. Mat's gonna work someone else or Matt. Yeah, exactly. Yeah. Um and so you have to really get to know us, and then you really have to get to know the great people we get to work with.
SPEAKER_01That's right.
SPEAKER_03Like, how do you do that?
SPEAKER_01Yeah. So I'm blessed to be able to give, be given the permission slip from the the Sean's of ask me anything.
SPEAKER_03That's true.
SPEAKER_01So the ability that is for me when I'm talking to, which is obviously wonderful when Sean says to Matt, you just need to meet Helani. And then Matt's like, okay, you know, peel back the onion to the center and let her learn everything. Yep. You have to do it in an accelerated way, which is fast trust.
SPEAKER_03Yep.
SPEAKER_01Uh, which is helpful and also kind of magic at that, actually, in thinking about it.
SPEAKER_03Thank you. Yeah. Fast trust. Because I do just totally trust you.
SPEAKER_01Yeah. Fast trust is key. And then respectfully, like kind of in the line of trust, the quality of your questions.
SPEAKER_02Uh-huh.
SPEAKER_01Uh, and also I make a joke often. Um, sorry, Sean, you're not a special executive. You all suffer from this same problem, which then creates a little bit of comfort. It's like, okay, then she this isn't the first time she's heard this executive problem. And then with that, there's the trust building. Yep. Um, and then of course, for the executive assistant audience, having served in that capacity uh for so long, it's like, oh my God, you absolutely get me, because there's a lot of misconception about that.
SPEAKER_03Yeah. Well, and you have so much data. And it is, I will tell you, as someone who, you know, like like when I'm doing an MA transaction or something for a client, I will give them a roadmap at the beginning and I will say, here's where this gets stressful usually. Uh-huh. Here's where it gets emotional because you're selling your baby. That's absolutely like other than giving up a kid for marriage or something. Like it's the most like intimate thing you probably do or like personal. Fratch. Yeah, exactly. And you've been like killing yourself for 20 years. That's right. Keep it alive. And so, I mean, almost every person cries, gets emotional. Yeah. It's like, what am I doing? Am I selling out or whatever? And so um, I find, you know, I'm you don't have to be that smart to just once you've done something a thousand times, you're like, well, here's what happens. Exactly. So to your point, when you tell someone like me, here's the challenges, or here's where people like you often struggle, and you're like, oh yeah, that's right.
SPEAKER_01Is she spying on me? Does she have a yeah? Is my office might yeah, yeah.
SPEAKER_03It's like, oh, Helani knows what's happening.
SPEAKER_01Which is actually a great segue to the next question. What distinguishes a great lawyer?
SPEAKER_03Yeah.
SPEAKER_01So from a great leader, right? So you had to do law. And then as you were building MODIS, and even now as you're managing and leading teams, you have to do you l you live a double life, I'll say, right? You're you're toggling and having context switching from the legal side to then leading people. Yep. Um, and within that leading people, some don't work out. Uh-huh. Uh, and what's the difference, right? If you're living a double life, the lawyering and then the leading of a team. I mean, for someone that might be watching this, it's like, I gotta start my own firm. Uh-huh. What what might you want to say?
SPEAKER_03I would say, go for it. Um, great, go for it. No, I think law's really interesting because it's such a diverse practice. And I think one of the things I love about our firm is we have um incredible technicians who are like craftspeople. And and there's a lot of people at our firm and and lawyers in general. I don't want it to sound like a commercial, but um who love the craft. Yeah. Um like that's a great word to use for like a Latin word. Um I I often think about this, it's it's like the root of technique, and it's like the love of the craft, like like artisan or whatever phrase you want to use.
SPEAKER_01And so even though it's words on paper, there is an art to the paragraph and what it conveys. And literally the and we worked together just recently on my agreement. The switching of one word makes such a difference. So that's when you're in lawyer, which then you're very good about this. The tact when you're verbally delivering to staff has got to be an art form. Again, a craft.
SPEAKER_03Yeah. Yeah. And I think, you know, I think I'm a fine lawyer. I I get to work with like amazing lawyers, you know. And I think too, um, like one of the processes on, I talk to my son about this all the time, is like, what are you optimizing for? Oh, smash. Get data, yeah, re-evaluate, right? And so it's like, okay, you know, sometimes a client is like, this is a great deal. We don't want to ruffle feathers, give us the simplest, cleanest way to do it. You know?
SPEAKER_01Yeah.
SPEAKER_03Um, or sometimes it's already so stressful.
SPEAKER_01And then the emotions are high as you were sort of saying.
SPEAKER_03Totally. Um, or sometimes they're like, hey, we're not really dying to sell, or we're not really dying to do this. So like make sure we get everything in our favor. And if we don't, we'll walk.
SPEAKER_04You know?
SPEAKER_03And so like you really have to listen to them to see what they're optimizing for. Is it just to get a deal done, or are they, hey, I'll happily walk away? Um so, so there's that side of it. On the people side, I mean, I do really enjoy that, if I'm honest. Like it's been um Denver, the Colorado market is probably, I mean, it's pushing a hundred people now. It's probably 90. Um and it's just a totally different, you know, when we started, there's like five. Um, and so it's just totally different.
SPEAKER_01Um that was in 2018 that you launched.
SPEAKER_03Yep. Okay. Yeah, we merged, yeah.
SPEAKER_01Eight years. Yeah. Yeah.
SPEAKER_03It's been crazy. Um believable. And and um, I do love that. Like I just we, as you know, you've met some of my colleagues, like, we just have the greatest people, and so different. Like, I loved that about you.
SPEAKER_01It's like the idea, I always say, okay, we want to find more Sean clients because that's the right culture of people, that's the right leader that they're gonna work under. So yeah.
SPEAKER_03Thank you. Yeah. So, so yeah, I mean, I think being present is the main thing. Like, you know, not doing this while you're talking to people or whatever. Like um uh I shouldn't even have it on here, but um, but but yeah, I think being present with people and and like listening and and everyone, especially now, you know, there used to be sort of like one track in law. Like I start, I grind, I make partner. Sure. Like, and a lot of people don't want to be partner anymore. Right. That's cool. Um it's like, how can we meet you where you are and give you like the best self-actualized version of you?
SPEAKER_01Yeah.
SPEAKER_03Maybe that's partner, maybe it's not, you know.
SPEAKER_01And you've probably seen in all of this time the expansion of like the different niches. So my niece is uh currently wrapping up her junior year. Okay, and she's doing legal in the real estate category. Which I'm like, oh, that's evergreen. Like that'll go for just a long time. Yeah, long, long time. And she thought, like, oh, the commercial side of real estate with law. I was like, Wow, you can even niche down to that. Uh so there's I'm sure you've seen a lot.
SPEAKER_03Yeah. Yeah. Yeah. And I mean, it it is very specialized. And sometimes that's frustrating. Cause like I say all the time, like, we want the most people to get the best outcomes like the most efficiently. And now, and you just see it over time, like now data privacy and security, and you know, like that becomes such a big issue. Obviously, like AI compliance. You see, um A couple of years ago, it was like employment law was super and it still is, but sure. Um just super intersecting everything. And so it's a balance. Like again, you want people to get good outcomes, you want people to be protected, you want people, but also um, like there's a phrase called transactional friction. And in some ways that's what lawyers and accountants and investment bankers are. It's like these are the terms, but it only people trying to do something. Sure. The rest of us are friction. Now, if you get a better price or you don't get sued, or you don't close a deal because there was a big issue, like that's really important friction.
SPEAKER_01Like sometimes friction's and with all of the experiences you've had, yeah, you can predict some of that, right? Your crystal ball, you can hopefully hedge it. Don't make my head too big. Yeah, exactly. You do start to pick up trends. You said something, and and this was one of the reasons why I wanted to talk to you. AI in the legal field.
SPEAKER_03Yeah. Nothing going on. All right, we can just end this now. Yeah, we're all good.
SPEAKER_01Nothing going on. So there's no, there's no romancing of the two.
SPEAKER_03Yeah. No, it's insane.
SPEAKER_01It's insane. Yeah. I mean, I shared with you over an email someone who's launching uh an AI tool to specifically support the judges with information about laws and and legalese. And I was, I sent it to you. I was like, had you heard about it?
SPEAKER_03No, I'm obsessed with this actually. Sure.
SPEAKER_01So you don't have AI fatigue right now.
SPEAKER_03It's funny. One of my great friends at the firm, Betsy, was we were just all talking about this at the thing. And and there is some of that for sure. Of course.
SPEAKER_01Okay. Um but it's exciting.
SPEAKER_03But it's mostly exciting. And I spend honestly most of my weekends um playing with AI. Playing with AI. Okay, great. So on like there's a lot of good things. You know, I work with a ton of startups and growth companies. And so frankly, you know, whether it's Anthropic or Harvey or Lagora or any of the tools, now they can use that to get oftentimes like 75% there. Yeah. Um, and especially if they maybe have an in-house counsel or someone who's savvy, it's a really good starting point. So we're getting lots of emails that are like, hey, I did this on ChatGPT or you know, Cloud 4.8 or whatever. Um, can you just take a look at it, make sure it's good? Sure. And you know, on one hand, you could say as a lawyer, you could kind of be high and mighty and like sit in your ivory tower and be like, no, only I can draft this.
SPEAKER_04Yeah.
SPEAKER_03It's like, no, actually, you know, if they're trying to do something pretty simple and they can use that tool instead of, you know, paying me to spend five hours on it, it's a good outcome. You know, like because we'll have plenty of ways to help them and plenty of ways to be a service. So um you are seeing it just touch everything. Um on, you know, big transactions. The way junior attorneys used to learn is they would do diligence. So um, you know, if Coke was buying Pepsi, the Coke would say, Hey Pepsi, send us all your employment agreements, all your contracts, all your leases. Weeks. Weeks. Like they called it a war room, you know.
SPEAKER_04Yeah, for sure.
SPEAKER_03And you'd like go there and review all this stuff, and that's basically gone now.
SPEAKER_04Yeah.
SPEAKER_03Um, AI can really like process that and then you you spot review it and you do um certain things. Because it used to be like you'd look for employment agreements that had California law or arbitration clause or things that were like relevant. AI is like built for that, you know. Um so so yeah, so I mean it's really touching.
SPEAKER_01If a student's watching this, uh-huh, is there still a future in legal? There for sure is.
SPEAKER_03Okay. Um uh we have this conversation. We just our summers just left. Uh our summer social. And um, you know, first of all, I would say be the best AI like student you can possibly be.
SPEAKER_04Absolutely.
SPEAKER_03Because, you know, I'm I've been doing this a long time, and I'm not gonna be the tip of the spear with AI. I'm trying to be, but like the 25-year-old who grew up with it is really gonna be the best implementer. So um, but no, I think like anything, like I someone gave the example the other day of, you know, if you want to build a house in 1950, sure. You used to hire an architect if you were wealthy enough to do that, sure, and they would draw it out, and then you'd say, I want the garage bigger and the bathroom smaller. No one ever says that, but they want the bathroom bigger too. Um, and so they have to redraw it. And, you know, only wealthy people could have it architect. Yeah. Um, and it was really expensive and it took a long time. Sure. And then AutoCAD came out where they could just click and snap and send things to you, and everyone was like, It's the death of the architect. Well, of course, architects, you know, are more busy than ever. Sure. They can work with more people, it's right, more people have access to that.
SPEAKER_01Leverage tool for sure. Totally.
SPEAKER_03And I think law is gonna be the same way. It might be lumpy for a while. Um Well, it's trying to find its place.
SPEAKER_01Totally. Yeah.
SPEAKER_03Um, you're seeing like um Mark Andreessen talks a lot about it, where um you know what AI is maybe the best at is coding. Um, and everyone's like, there's not gonna be coders. And if you look, there's more coding jobs, coders, you know, developers, programmers, well, they need to share the decision fatigue. Uh-huh.
SPEAKER_01And they need to share um the uh uh input.
SPEAKER_03Yep.
SPEAKER_01And then people still gonna are gonna want to have a verbal conversation with a human being.
SPEAKER_03Exactly. About that. And that's for lawyers in particular.
SPEAKER_01I was gonna say for lawyers, that's huge. I think that's a good thing. So the savviness is just gonna be through the roof. Yeah. Okay, great. Yep. Um I wanna talk about the founders. I wanna, I wanna cover that. You know, for a portion of your career, you've been advising the founders through some of their biggest decisions. Can you either share a before and after story? And as we kind of touched on a little bit ago, you know, the patterns that you've noticed. And, you know, maybe there's a founder that's, you know, engaging right now with a lawyer or thinking about, like I had a guest on who uh launched a franchise component.
SPEAKER_04Yeah, yeah, yeah.
SPEAKER_01Never thought in starting her business 15 years ago that just three years ago she was going to start a franchise vehicle for what she's doing, which is very exciting. Uh and a lot of work. Oh, so much work, so much work. And uh, we had a lot of fun talking about it on her episode. What are you seeing in the founders? Kind of threading that a little bit with your double life, you know, that accounting piece, the the legal piece. What are you seeing with founders? And maybe just even in the last three years, what's going on?
SPEAKER_03Yeah, it's a great time. Um, so I've posted about this on LinkedIn, but whenever there's disruption in the economy, um you have an incredible, and we're seeing this right now. You've had the most solopreneurs in history.
SPEAKER_01Um Do you know John Windsor at a boulder?
SPEAKER_03I do know.
SPEAKER_01Who is that? Uh he has a Harvard lab. So he wrote a book called Open Talent.
SPEAKER_03Yep.
SPEAKER_01Okay, anyway, I digress. Correct. So you're seeing on LinkedIn a lot of solopreneurs.
SPEAKER_03Yeah, and um when you look at vintages of startups sort of post-02, like after the big tech bubble, was some of them, you know, you had Amazon and um Google and all these great companies kind of came out of that and thrived. And then post-08, you had Airbnb and Uber and like all these other really successful companies. And you know, we had a ironically sort of a venture boom in 2020, 2021. Yes. Then kind of a crash. Evaluations came back to earth. And then we're still in some ways, you know, a lot of the hyperscalers, fang companies, whatever you want to call them, have been laying a lot of people off. 5,000, 10,000, you know, Facebook, uh, or meta, Microsoft. Yeah, you're seeing it. And so it's tough, and obviously that change is hard. And when you're making a million dollars sort of at Google to be a project manager, you're not gonna start your dream company. Right. When you get laid off, you do.
SPEAKER_01Um there's the green slip.
SPEAKER_03That's what we're seeing the last couple of years is just like a huge proliferation. And then the other thing that you're seeing with founders, and I'll I'll answer your question too, but it's just it's a really interesting time with startups. Sure. Um, because you have all this talent that maybe entered the market with some free time.
SPEAKER_01Exactly. What am I gonna do?
SPEAKER_03And honestly, like some runway because you've been getting paid really well. For sure. Um then you also have with AI um the ability to generate code, business plans, all the things. So instead of it taking 15 people and 10 million dollars, yeah, it takes three and 500 grand. It's so true. So fun.
SPEAKER_01Um is interesting because that's a whole nother conversation about where capital's at right now, but um sticking with the startups. Yeah.
SPEAKER_03There's some fun stuff there. Maybe I'll talk to Matt about that later. Uh yeah, certain things are getting funded um like crazy, and certain things are having a hard time. Um, but we are getting liquidity in the venture market again. Okay, great. And so um that's helping, but yeah, that's a whole nother story. So, so founders to your question. Um, yeah, I think um, you know, the the thing that I always come back to with founders, because very often we call it like two kids in a garage. Like very often we're there day one. For sure. Whether it's a university startup or just someone coming up. I'm um working with some some really cool people right now that are doing like a clean tech type of thing. And um, and it's just so fun to be there at the beginning, like I said. It's so great that you're in the garage for sure.
SPEAKER_01And so then they have to figure out how to make payroll and what phone system to use and which is watching them totally take on an identity that they didn't have because now they're not just working in their business, they're scaling it and leading two founders. Uh, one was an exGoogle, uh, and the other was oh, excuse me, ex OpenAI and XMeta. And they both started together a cybersecurity company.
SPEAKER_02Oh, super cool.
SPEAKER_01And interestingly enough, one of the founders was uh getting recruited to help with cell phones of ultra high net worth while he was in college to create protection in the cell phone for their children. Um so I'm not telling the story as eloquent as he would. Um but when I heard that, I was like, I'm I'm hearing another movie, another Facebook movie come out, right? Uh just kind of getting recruited by the ultra high net worth parents. Can you do something more protective, you know, people in the government and stuff like that? And so he and a good friend, uh again, OpenAIX and Open Um Meta X, they both started a cybersecurity company. I did a search with them, they're out of uh San Francisco. Oh, cool. And they're like, we don't know how to lead.
SPEAKER_02Uh-huh.
SPEAKER_01We're learning that in real time.
SPEAKER_02Totally.
SPEAKER_01And I'm like, living it while you're learning it is fantastic, but it's hard, especially when now you're responsible for the people that are giving you some cash. Uh-huh. Um, and so they're doing great, they're thriving, um, they're very committed. And they're like 26 and 27, and I'm 47. I could almost be their mother. Uh, and so it's it's fascinating to see what's going on because they left and now they started this.
SPEAKER_03Yeah. And and there are certain like re to you your point earlier about recognizing patterns, like um you there's kind of the two kids in a garage, it's just all hands on deck for everything all the time. For sure. Um, and that in a weird way is easy, like Steve Jobs wearing a black turtleneck. Right. It's like, this is just what I do. Like I have to put out the fires. Um and then the first sort of inflection point is when they have to start, you know, they get some capital. Yeah. They're hiring two three. Exactly. Well, just like inspire this. How to interview who's right. Because, you know, one of the things you also see a mistake a lot of times is people who hire co-founders or early employees that are their best friend, they're like drinking buddy. I know. It's like that's not what you need. You need actually your yang to your yang.
SPEAKER_01There's immediate trust, you don't have to earn their trust. It's like they're gonna be all in it with you. Yep. I've got two clients I'm working with that they're working with friends they've known for 25 years.
SPEAKER_03Yeah. And sometimes that can work great.
SPEAKER_01And it can. And then I also called out one client with a question. I was like, do you think he's helping or hurting right now the search? He's like, I know he's hurting it.
SPEAKER_03Yeah.
SPEAKER_01Yeah.
SPEAKER_03No.
SPEAKER_01Which is hard. Yeah.
SPEAKER_03But the the biggest inflection point I see, just to maybe round out the founders thing, is it's usually right around 10 million in revenue.
SPEAKER_01Okay.
SPEAKER_03Um, andor, you know, 25 people. Because that's all of a sudden when you need like an HR person. Right. Like an employee handbook. And and again, you see, I mean, there's a million people.
SPEAKER_01Especially the visionaries. They're like absolutely not.
SPEAKER_03They suck at it.
SPEAKER_01Yeah. Like, and they shouldn't be doing it. Please don't do it.
SPEAKER_03I mean, um, I know there's Google stories where they interviewed everyone, um, Sergey and Larry, yeah, even when they had like three or four hundred employees, you know. Wow. That's like eventually, like, that's just not a good use of your time. Sure.
SPEAKER_01Sure.
SPEAKER_03Um, and you might not be the right person to analyze whether And are you fully present even in the interview?
SPEAKER_01Because you're thinking about all the other things you should be doing like that time and it's not time well spent. Exactly. Exactly. Yeah.
SPEAKER_03So awesome.
SPEAKER_01Uh kind of coming here to the last question.
SPEAKER_03Oh my gosh, that was fast.
SPEAKER_01I know it was fast. Uh and exciting. Thank you. Oh, of course. If if the Sean of today went back 15 years in the past to have lunch with Sean then, what what would you talk about at that lunch? What would you say?
SPEAKER_03Um, that's a good one. Yeah, I'm I'm torn because uh part of it is like I'm incredibly grateful to be where I am.
SPEAKER_01Right.
SPEAKER_03And even though there was a lot of pain, sure, uh, and bumpy roads and things I would have done differently, um I'm very glad I got to where I am. And so, like in the butterfly effect, sure. Thinking I'm like, I don't want to mess it up. Like I love my wife, I love where I am, like, you know, I'm super happy. Um, so like part of me would be like, don't mess it up. Um but then like more in an abstract sense, I would have listened to myself. Like, you know what's right and you know what you should be doing. And so often I think like I grew up with more of a scarcity mindset, um, yeah, hence becoming an accountant, accountant.
SPEAKER_04Oh, sure.
SPEAKER_03Um, and just like taking the safe route. And I think I would have been, especially when you're 25 or something, um, 15 years ago, I would have been a little older, but like um, but especially those younger years, it's like take the chance. Um like, you know, um, you don't have a mortgage, you don't have kids, like maybe take that extra trip.
SPEAKER_01Exactly. Or maybe don't.
SPEAKER_03Yeah, yeah, yeah. But like, you know, I I mean, honestly, we started the firm pretty early. I was only a couple years out of law school. Like, that was one example where I did kind of take the chance. Um, but there was a lot of other things in my life where you kind of just like get locked into comfortable.
SPEAKER_01Yeah.
SPEAKER_03And you're like, you know, you're not happy, or you know, this isn't who you are. And it's like, do you know, rip the band?
SPEAKER_01Which actually makes me think of I was thinking about this as I was driving here today. I was like, what would my answer be?
SPEAKER_02Yeah.
SPEAKER_01And I think I would say, and I would tell her, it's all gonna work out.
SPEAKER_02Uh-huh.
SPEAKER_01It's all gonna work out. And just kind of sit on that. And then, and then I'll say, So, you know, how's it going right now with the kids? And like, you know, hey, this this is did this just happen yesterday, and kind of like just revisit, or actually, hey, can I see my kids? Because it was 15 years ago and just seeing them in that little baby phase because my youngest is 16 and my oldest is 21. Which is crazy. Yeah. Uh Sean, this was wonderful. Thank you. We're already done. Thank you so much for your time, your wisdom. I'm very excited to have had this conversation.
SPEAKER_03Well, likewise, yeah. Well, thanks for all you do and everything you've done for me and our friends. So appreciate you.
SPEAKER_01Thank you.
SPEAKER_03Yeah.
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