Kayla Jimenez and the Work/Life Balance

Kayla Jimenez:
I’m pretty grateful to see how our clients do it. It’s like we get to peek behind the curtain and see how they’re making money, how they’ve made decisions, how they mitigate risk. I say this all the time because I’m a lawyer. So you have lawyer friends? Two of my exes are lawyers. My best friend’s a lawyer. My other best friend’s a lawyer. But their clients aren’t as cool as ours because they represent big corporations. They’ve been doing the same thing for the last 50 years, pretty much our clients, man, to see how they’re working the system. It’s like peering behind the curtain. We’re lucky that we get to do that.

Dana Robinson:
Exit Plan is a podcast for business owners and those who want to be business owners. I’m always in search of the lesser-known stories of entrepreneurship. In the exit Plan podcast, you’ll hear stories from startup to sale and hear from the professionals who helped business owners achieve their exit. Hosted by me, author and private equity manager, Dana Robinson, along with my co hosts and guests, you’ll hear real stories, tips, and tools that will help you plan for the exit you want, whether you are still working at a day job or running a business. Let’s get started with this episode of the Exit Plan podcast.

Dana Robinson:
Kayla Jimenez welcome to the Exit Plan podcast. For those that are old, Opt out Life podcast followers, as most of you know, at this point, we’ve rebranded to the exit plan and sort of narrowing the interviews to entrepreneurs, the entrepreneurial journey, the journey from employee to entrepreneur, and the journey through entrepreneurship and ultimately to a second exit. I like to think of the first exit as the one you take from your job to a business. And then in most people’s case, you’re going to take an exit out of your business. At some point it’s going to give you a liquidity event or retirement or something like that. I’m podcasting today with Kayla Jimenez, my former law partner, and before that, my associate, and before that, my law clerk who is now operating my law practice. And super happy to have her on because we’re going to talk about her entrepreneurial journey to going from a person who was a law clerk during law school for me to owning running a law practice that is entirely hers. And at the same time, I think Kayla and I have some common stories about the entrepreneur clients we have that are always instructive. Part of the reason I started opt out and wrote my first book was I just felt like I was around a lot of smart people who were entrepreneurs that had done things in ways that I don’t know if people really understood. This is how you do it, because we’re so fixated with shark tank or the idea that you get a big idea and that that’s going to be like winning the lottery. And reality, the story is a lot different, and it’s a story I try and draw out of people. Kayla, I hope to draw that out of you today. Thank you for coming on the exit plan podcast.

Kayla Jimenez:
All right, I’m happy to be here, Dana. Thanks for having me. I’m sure I’m, like, one of the more boring of your guests here, because I know some of our clients, and they run the most entertaining, weird, cool businesses out there. And then I’m just their lawyer, but it’s fun to be close, at least adjacent to what they’re doing, because it’s really awesome.

Dana Robinson:
Yeah. And they teach us a lot. Being an attorney, I think the part that I liked the most about it was that diversity of being part of someone else’s entrepreneurial journey, someone else’s experience, being able to learn from it, participate, get excited about it, maybe not carry all the risk they had, but to see them through that and do my part for that. And over the years of that, because I’ve kind of dug in and been an entrepreneurial on dozens of things, I have been able to hijack a lot of that. Good, bad, and ugly. Right. All of the things that we see our clients do. How’d you end up working for me? You probably tell that I’ve told the story before, but I’m not sure. I fly on a wall hearing the story of how you end up working for me.

Kayla Jimenez:
Okay, well, I was a one l and it was during the recession, and my background was biotech. So I came into USD school of law, went to the first counseling meeting, and was immediately told, you’ll never be an like that. They looked me in the face and they told me that, which was really disheartening because I loved the scientists and all the weird things I got to watch people invent. And I was really bummed out to hear that news. And also, I’m very contrarian, so I’m like, well, just for that, I’m going to show that it’s wrong. The problem was, I didn’t have lawyer connections. I didn’t have a friend, a family friend who was a DA or any of that going on where all of my law school colleagues had summer jobs lined up through family or friends. I had nothing. So I went on Google and typed in San Diego, IP attorney and Dana tech law came up and I sent a cold email basically begging for a job. And you were kind enough to offer me an interview. And in the interview, you kind of gave me the real talk. Real talk. Kayla, we’ve already hired our clerks, but if you want to show up for some pro bono stuff, I’ll see if there’s anything for you. So I showed up because those career services people were not going to be right about me. And I got to do a little bit of pro bono work, and then you had a little bit more work and then a little bit more, and some of the clerks you had left or summer ended and I stayed on and I just became your clerk. And it was a great experience. I went off to work at a fashion law company after that, but really liked boutique law and really liked working with entrepreneurs. So after bar, after I took the bar, I came back at tech law and got to work with the really cool clients I had been working with as a clerk. So it was great. And that’s how I kind of wound up working for you. How I ended up becoming more than your associate was a different story.

Dana Robinson:
Yeah, I don’t know if you want.

Kayla Jimenez:
To tell that version.

Dana Robinson:
Well, just to be sure that everybody hears it, this is, I think, a good story for those that are early in their career. I think it’s a good story for young lawyers who might be the law. Hiring law. Hiring is tough. You get out of school and you’ve got six figures of debt, and you wonder if you’re going to ever get a job, and it feels like everybody else is getting offers and you aren’t. And the reality is you did this thing that is incredibly good advice. You found something that you really wanted to lean into. You found a firm that was smaller, that might be scrappy, and you showed up. And when I said, I’ve already hired the two that I have in my budget, you were like, well, I’ll do anything. And I said, well, I can’t hire you for free because there’s these California labor laws that mean I can’t give you real work. But I said, there are pro bono clients, people that are just nonprofits or literally clients that are on the edge of not being able to pay their own bills because their businesses are suffering. You could do their pro bono work and it’s free. Like, you can help someone as a favor and just get some experience. I’ll do the mentoring. I’ll hand you some stuff. And you leaned into that hard and fast and really did well, you didn’t take anything for granted, and I saw that. And you’re right. As someone who at that point had probably employed 25 or more clerks through my career, I spotted some talent, some ambition, some hard work, and I was like, I got to move you to paid now because I don’t want to lose you. And then as a law clerk, you killed it. And then, yes, like all law clerks, you disappeared for months while you took the bar, and you ended up working for another company, which actually brought a whole bunch of experience that also probably didn’t pay well and probably also was really hard in a bunch of different ways from a legal standpoint, for those that are lawyers or future lawyers, what kind of experience did you get from working for that organization?

Kayla Jimenez:
Yeah, working for that company was a really good testament towards go with your guts when it was a very flashy company. It was doing exactly what I thought was really interesting, which is heavy ip, heavy litigation, really interesting, cutting edge issues that went all the way up to the 9th circuit and the eigth and the second so prestigious cool ip stuff. But when I interviewed there, I got a bad feeling about it and I ignored that bad feeling in favor of the work itself because the work was so great. And another attorney who worked there was really great. I knew she’d be a great mentor. Nothing bad about that. But I just had this sinking feeling like, oh, this is a little creepy. This is a little weird. I don’t know about this, but I ignored it in favor of the work. And sometimes it serves you well. In this case, I should have gone with my gut. Great experience from a legal perspective. I learned a ton. I learned how to litigate very precisely. I got to work on great cases. Do not regret that. But it wasn’t the environment that I really wanted to be in long term. And I think I could have saved myself some headache had I recognized that at the beginning. So double edged sword. Looking back, hindsight is 2020, but I’d say to a lot of young attorneys out there, if something feels wrong, like really wrong, listen to your intuition, listen to your gut, because usually you can pick up on cues and your brain can’t logically connect them, but there is something off.

Dana Robinson:
Good. I think that’s great. I actually have multiple experiences working places and then knowing that I need to leave. And I call this the shelf life. Actually, I have like a word for it. I talk about it in the next book I have coming out. Dana Robinson here.

Dana Robinson:
Quick plug for my book, the King’s Flyswatter. You can see it here behind me? If you’re watching this, I’ve got it in my hand. It’s a beautiful hardcover book, printed to make giftable something that you can share with a family member buy as a gift. So this latest book, it’s a fable about a person who has a really crappy job. Let’s just start there. This is a book that most people can relate to because we’ve all had crappy jobs. This is the story of Ubar, a servant in the court of a babylonian king who masters his boring, monotonous job and then learns to listen to the king, hearing him rule the kingdom while quietly swatting flies behind the king. Eventually, Ubar becomes the wisest and most successful man in the kingdom. The story is fun, and it’s easy to read, but it’s not mythology. It’s my story. And as I shared the idea with colleagues and friends, I learned that it was their story. And guess what? It’s your story if you’re at a job of any kind, one that you love, one that you hate, one that’s just enough to get by. This little book gives fresh perspective on how to leverage that job to get. You something greater than a paycheck. The lessons in this parable are entrepreneurial lessons, but not what you might think from the current entrepreneurial zeitgeist. If you or someone you know are looking for a real pathway to entrepreneurship, here’s the secret. Your job is the way out of your job. It’s counterintuitive, but once you see how it works, you can’t unsee it. Learn the way of the fly swatter from the parable of Ubar and from the stories I share from my 30 year business journey. You can get a free copy of the King’s Flyswatter by going to danarobinson.com.

Dana Robinson:

It’s really important to navigating your career path. It’s important when you’re even a business owner, when you’re making decision. Should I take this client on, for example, that you understand this kind of, like, trade off between something you shouldn’t be doing, maybe even don’t want to be doing, and the need to gain the skill from it? And, for example, you did. You’d filled a year of your schedule and gained five years of talent and experience from that and paid a high personal price. And I wouldn’t recommend anyone do that necessarily. But I do think that when I left the law firm where I got trained, I knew I couldn’t stay. And I liked some of the people I liked. What I was learning. And I just knew that the cost benefit analysis, they’d say that the juice ain’t worth the squeeze, is what a lot of business people that I’m around like. To use the phrase to describe that situation, once you find yourself in it, you could certainly cut and run, but you stuck it out. It paid off. I’d say most people, you find yourself in a bad situation if your real journey is that eventually you want autonomy, agency, work for yourself, be a partner in a law firm or whatever organization of any type. You have to be careful about making those decisions. We’ve known people that have inadvertently burned bridges by cutting too soon. But once you know, I think you have to make some very deliberate decisions about what your extraction is going to be so that you don’t overstay that shelf life and turn sour or have it turn into toxic things that impact you or your career. And in your case, it worked out great because working for me seemed delightful and amazing after having a tough job. So I got you back. And this is also a fun story about when you came to work for me was kind of like when you came to me for the internship job. I’m like, sorry, can’t afford you. I’m trying to run a business. You came to me, and I’m like, I can’t hire a lawyer. That’s insane. I’m paying me, and I only hire law students. I got a paralegal. And you’re like, well, I could just get paid based on what I do, which is pretty entrepreneurial for someone who hadn’t run a business. And most students are just like, I need a job with a paycheck and a want a nice lifestyle, and blah, blah, blah. You were just like, I’ll work, and I’ll get paid if I work. So I structured a deal that was actually kind of like a partnership deal early on. I mean, it ebb and flowed. It meant that there were months where you got 30 hours in the whole month, and you got paid a piece of what we made on the work. And there was times where you probably got triple what your peers would make in a month, but you also had to go to trial and work hard. So, yeah, your entrepreneurial offer really was to say, I understand this business. I don’t necessarily need to have a job job. And I was like, yes, let’s do that.

Kayla Jimenez:
And I loved what that taught me really early on as well, is while my peers and friends had kind of cushier jobs with a straight salary, so they could always predict what they were getting the first and second year, they go out and spend like crazy because they’re getting paychecks every month that they can count on, which is great for them. But I love that I didn’t have that because I kept living super lean. Like I was still in law school. I was able to bank a ton of money. And then I spent enough time around you, Dana, and the other people at the firm who were a little scrappy, a little entrepreneurial, where you start to, you know, money’s only good if you invest it wisely, so it’s got to work for you. And the other thing I learned working for you and seen all of our brilliant clients is you don’t get rich working a nine to five. This is the huge american lie that they tell all the kids, get a good job, go get your doctorate, go get your phd, go become a doctor. Like, work at the work nine to five, or work your salaried position. You’re not really going to be mega rich doing that. You’re only going to be that top, top level if you’re investing that incredibly wisely, not just spending like crazy or going on trips all the time and blowing it in a week. So it was good to see how our clients reinvest money in real estate or all sorts of different types of businesses or different types of investment schemes. It was very instructional for me. So I’m kind of glad I didn’t have the salary.

Dana Robinson:
Right at the end of the day, by having some autonomy saving, you realize that holding on to money is what growing wealth is about. And so you had nice car at one point, and you’re like, buying a multiplex. And guess what? I can’t have a car payment qualify for that loan. Boom, no car for a little while, borrow a car for a little while, get a cheap car to survive after that, and then you end up owning real estate, which probably made you a ton of money since, and given you more autonomy and kind of long term wealth and more control over your life. And the people that we know that had jobs, we call them the working rich, and it is this golden handcuff problem. You go, well, I got a $1,000 car payment. I had a condo at the beach I sold a couple of years ago. I’d have held it for twelve or 13, maybe 15 years. It was a million and three. I think that condo. A guy tried to qualify who had a $400,000 a year job as a vice president, and he was in Vegas, where there was no state tax and he couldn’t qualify for the $3,600 mortgage at the time for whatever million dollars after his down payment, because he had two $1,500 lease payments and a completely overpriced house payment and no rental income and one w two income, and he wanted a beach property. So the working rich, I guess as a peers, that they and their peers kind of sabotaged their own ability to become self employed, or even just the ability to rise within your organization is sometimes contingent on your feeling that you’re not completely dependent, that you have the freedom on autonomy to say, fire me if you don’t like what I got, what I bring to the table.

Kayla Jimenez:
Yeah, I’m pretty grateful to see how our clients do. It’s like we get to peek behind the curtain and see how they’re making money, how they’ve made decisions, how they mitigate risk. I say this all the time because I’m a lawyer. So you have lawyer friends? Two of my exes are lawyers. My best friend’s a lawyer. My other best friend’s a lawyer. But their clients aren’t as cool as ours because they represent big corporations. They’ve been doing the same thing for the last 50 years, pretty much our clients, man, to see how they’re working the system. It’s like peering behind the curtain. We’re lucky that we get to do that.

Dana Robinson:
Yeah. And let’s talk about a couple of the common themes. As Ip attorneys, we do get a lot of clients that have crazy ideas, and I don’t want to completely diminish this, that sometimes the crazy idea that you get a patent on or that you start a company around, sometimes that’s going to work. But it’s actually not the most common theme. The most common theme, I think. And we obviously can’t say clients names in public and comment about their businesses. But the most steady path, if I were to synthesize it into entrepreneurship, into, like, successful, I own a business, I run the business. I have employees. I have some autonomy. I travel when I want. They have done something they learned often at a job and often at a job they didn’t like. And now they’re taking those skills, the talent, the network, the relationship capital, and they deploy that and become self employed based on that. And I don’t know, can you reflect on that? Do you think I’m crazy or is that better out to your client base?

Kayla Jimenez:
No. 100%. A lot of my clients come from my biotech days. And again, recession time, it was the recession. I had to get a job and I got a job at this startup biotech company that had DHS and DoD grants. And the manager, the creator of the company, actually was very entrepreneurial, and he kind of almost made it his mission just to hire women engineers and scientists. I think maybe because they were the ones who, during the recession, were looking for jobs, that’s possibly why. But this lab was full of all these women who wanted to work at BP or Amgen, but because it was a recession, they weren’t able to get that job. So they worked at this startup, and this startup was super know I can talk about how we use McMaster car drills with handmade propellers as aerators to save $1,000 of buying an actual air. Anyway, it was a little bootstrappy, but the women that worked there were brilliant. They learned a lot there. They learned a lot about managing. They learned a lot about how to get grants, government grants. And then they took that and ran with it. And one of my best friends was, she was my manager at the company, and then she took that and went to Mattel and Rose all the way through the ranks at Mattel, left Mattel and started her own toy company and is killing it. And everything traces back to this one bootstrappy job where she learned how to manage in kind of a chaotic environment and find her own solutions to save money, which is very entrepreneurial trait. But she wouldn’t have learned that if she had just gone and worked for some large aerospace engineering company. And now she’s worth millions because. And it all traces back to this kind of bootstrappy approach. So, yeah, our clients are crazy ideas, crazy stories, but amazing to see the trajectory. That’s the one I can really think of. But we have a ton of clients who are like, wow, you really applied this skill you learned in an awkward situation.

Dana Robinson:
Absolutely. I find myself being presented with clients that do something I didn’t even know existed. I mean, and even sometimes when you’ll hit me up for some sort of high level input on something new, you get in. And this is one of the things that always motivated me. I was fascinated by, like, I don’t even know what to say yet because I don’t understand what this even is. And of course, they didn’t just wake up with a stroke of genius and have this crazy idea they were someplace at a job where they did this kind of stuff, and they were like, I can do one better when I go on my own. And they do. So we end up with just a lot of innovation that happens by innovate, not in the abstract. You innovate around what’s already being innovated. By taking advantage of the opportunities to grab hold of the knowledge, the wisdom that’s around, you build relationships from that. And yeah, I think it’s the main story of even IP attorneys who we do. Like, when I was a new lawyer, one of the partners said, we do everything here on patents. We do electric forks. Same day we’ll write a patent on a medical device. I’m trying to picture what does an electric fork do? But I think it spins for the spaghetti. But it’s always the story I remember from Ted because I was like, there’s such a thing as an electric fork. And he’s like, everybody, see, I thought.

Kayla Jimenez:
You were, I thought you were going for vibrators. And I’m like, man, the amount of cases I’ve done based on vibrators or vibrating mechanisms is like off the charts at this company. I always have to warn the law clerks. I’m like, listen, you’re going to have to be okay with working to describe a massaging device.

Dana Robinson:
Yes.

Kayla Jimenez:
They pay their bills, though.

Dana Robinson:
These people pay, yeah, absolutely. Well, I mean, an early lesson in intellectual property law is that the things that we consider marginal really aren’t right. These are just sort of more puritanical in the most part. But when you’re an IP attorney, you take whatever your clients are innovating around. But to that point, here’s like an interesting analogy to what I’m trying to drive home. I guess you can’t just wake up and say, I’m going to innovate new vibrators because I use them. You actually probably need to be in the business because you need to know what are the trade shows, who are the buyers, what’s distribution like, what’s the markup? What are the merchant services? There’s 1000 things you need to know about that business before you enter it. And so I actually constantly talking to people who want to be an entrepreneur and they start with a thing. I want to be in this industry or this business. And you’re best not to just start something unless you go work for someone already in that business. I would say go work in the massaging vibrator business. And I think we’re calling it the women’s health business now, women’s sexual health, if you want to even use the sex word. But there’s a vast industry full of, it’s a multibillion dollar business, and I want to come up with a cool business idea in that space. Ought to start with you actually knowing that business space.

Kayla Jimenez:
I’ll say that I second that. I see a lot of my clients who are very successful are the ones that either have a very deep understanding of the industry that they want to be in, either because they were in that industry or they work tangential to that industry. You can make a jump from. I was a marketing director at large toy company, and now I’m developing toys. Because you have those connections, but those are the ones that are successful. Or, I mean, I hate to say it, but this is the social media era. The TikTok influencers who just have a massive following. They can pretty much get into whatever they want, and as long as they sell it to their fans, they’re going to be fairly successful. But influencing is its own brand of entrepreneurship, and, I mean, that’s, like, beyond the scope of what I’m qualified to talk about, since I don’t even have social media. So just my fake accounts.

Dana Robinson:
All right, so you actually raise a great point. Just in case there’s young people listening. I’ve read multiple statistics, and it’s only getting worse. I’ll say worse. Not to offend anybody, but a very large number of people under a certain age want, as a career ambition, to be an influencer. So there’s this category of thing that basically is the largest. In other words, you could take everyone who says, I want to be something, a fire person, a lawyer, a teacher, a truck driver, whatever. The thing you’d fill in. I want to be a blank. The number one thing in America, probably around the world, is influencer. I think the reality is still pretty similar to the narrative we’re talking about. The people who actually nail it are typically someone who’s gained an expertise in becoming an influencer, and they’ve done that by working for influencers. I mean, there is a very famous, probably the most famous influencer in the world was someone’s intern before, and they were an intern for an influencer. Do you know who I’m talking about?

Kayla Jimenez:
Oh, Kim K. She was Paris Hilton’s stylet, right? Closet lady.

Dana Robinson:
Yeah, absolutely. She didn’t just decide one day, I can influence. She watched a business develop around Paris Hilton, was an intern around it, gained the skills, and said, I can play this game. I can get some chips at this table, and ended up being the table, really completely defining what an influencer is. So, for all you kids who want to be an influencer someday, go work for an agency. Go work for an influencer. Work for someone who’s succeeding, volunteer. There’s a thousand things to learn about it. Because it’s a business before you can turn it into something. And even those, Kayla, I think, really are businesses. You don’t really just float around and take pictures of yourself. I mean, one of my colleagues from the air conditioning business that I was part of, his wife is, I would call her an influencer, is 700 and something thousand followers. Technically, probably an influencer. Do you have to have a million?

Kayla Jimenez:
I don’t know. I’ve got a couple of clients who are over 500,000. And so we consider them influencers. But I think you can be an influencer as long as you’re selling product to your crowd.

Dana Robinson:
That’s the game. So she had to learn, and her husband, who’s my friend, had to learn. Here’s how you create these affiliate programs. Here’s how you figure out what is it that I influence around and how can I find a product that my audience wants to buy? And she’s delightful to watch and charming. She decorates and decorates and decorates. And then I see packages show up that my wife has bought because she’s been watching Elle Peterson decorate her house. And I’m like, she’s an influencer because she’s influencing my wife, who’s pretty frugal, to buy cool things that she wouldn’t have known about. So that is a business that requires her full time attention, a lot of technology skills, a lot of marketing skills, and at the same time, she has to be the actor, producer, director of photography, prop master of her own productions every day. So I’d say even the influencers could take a card out of this. Like what we’ve learned from our clients, that you have a lot to learn to become the successful entrepreneur that really does have a business.

Kayla Jimenez:
Yeah, I think you’re right. I was thinking of the ones that just dance. And I have a client who got famous just for the dances, and now she wants to sell padded socks. So I’m like, you know what? I bet people would buy your padded socks because they love watching you dance. And if you danced in the padded socks, I’m sure you’d sell them.

Dana Robinson:
Yes, but then you have to find a source to import padded socks. You have to know that they need to be marked up ten x. You need to pay customs and duties on padded socks. You need to figure out how to do Amazon FBA as a distributor of your socks. There’s a lot of that stuff to learn.

Kayla Jimenez:
Well, sometimes there are, and there are businesses. I was going to say there are businesses just built on that. I want to blow this product up and they go to a consultant who gives you the checklist and helps you get your contacts. Have you heard of these businesses? I have a client who runs, like, one of them. They’re fairly successful.

Dana Robinson:
Yeah, absolutely. Another story of a business that probably got learned by somebody who worked at a business like that, or who did that thing and said, I can do this for a bunch of other people.

Kayla Jimenez:
Yeah.

Dana Robinson:
I love the entrepreneurial journey, and very often you work for someone and then you go, hey, I can do that thing, and you go do it. I did that with my little law practice. And sometimes you just end up wearing out the guy who was ready to retire. So let me tee up how you ended up being the partner and me being the associate. I used to joke, and I think I was joking, but maybe in the back of my head, and it was true. We had a very small office at one point, and I’d wave my hands around and say, kayla, someday all this will be yours. It was a very dramatic statement, and you’d laugh and I’d laugh, and it was often when we were doing something that was very frustrating and chasing too many cases at the same time or whatever. So I would make that joke and probably I talked about shelf life. When, you know you need to move on is important to understanding how long you can devote your attention and energy to a job. I think it’s the same thing when you work for yourself. So I was getting to a point where you’d come to me with things and I would be like, hey, I can’t look at this 80 page contract, Kayla. It’s going to make my eyes bleed. I’ll cry. It will be horrible. It was no longer fun, and I knew that was starting to happen, and you knew it was starting to happen. So I would just say, I’m going to trust you to keep doing this for long enough. You just do it. But come back to me and I’ll walk you through the architecture, we’ll narrative through it. I’ll talk about what I would think about this deal. So then for several years, I actually got good at that because that was more enjoyable. I didn’t enjoy sitting down and writing a contract from scratch like I did twelve years ago where I did, I’d sit down sometimes and have a blank page and just start writing. And there was some joy in that. Once that joy is gone, you just can’t keep lawyering or you’re going to make a mistake. And so I had the privilege of you being able to do all that stuff good and me to just sort of play senior partner, think high level, let you do everything else, and then, I don’t know. Was there a point where when I was saying, someday this will be yours, you were like, yeah, I’m known this firm, someday. Or were you just like, that’s goofy.

Kayla Jimenez:
No. Okay. This is probably anti entrepreneurial, or maybe it is the fundamental thing all entrepreneurs want. I don’t know, because I’ve never asked this question to my friends who are entrepreneurs, but my sole motivation was, how do I keep doing this job? Which I love. I love ip, I love my weird clients, right? How do I keep doing this but getting to live a full life with all the other things I like to do, painting and designing houses, know, going on dates or surfing, whatever it is, how do I get to do all that? And that is not at a big firm, that is not working nine to five. I can’t be at Boeing and be able to go live in Montana for four months or know, to Africa for a month, or all the things that I really wanted to do. I couldn’t go to art school, any of that. If I had a traditional job, I had to be in a job where I was basically the boss. So it wasn’t motivated by, I want to make a ton of money for myself, or I want to own something or I want to build something. It was just purely, how do I keep doing what I like to do and have the maximum amount of time to do also other things that I like to do to be well rounded. And that’s it. That’s how I came to that conclusion. So when you were kind of, I would say, like, just kind of moving on past the law, I still wanted to do it, and I thought, well, shoot, don’t want. I know I could go. You even told me, Dana, you can go to another big law firm, and I’m not going to be offended. You’ll probably make more money. Yeah, maybe that’s true, but it would not give me that freedom to still have another part of my personality that wasn’t just lawyer Kayla. And that’s the goal. And I don’t know, maybe other entrepreneurs feel that way, too. They pick being. Owning their own business and being entrepreneurial because they don’t just want to be defined by their job. They want to be a full, well rounded person. And it’s really hard to have a full time job and still have that kind of flexibility. Not impossible, but I think it’s hard.

Dana Robinson:
Yeah. So you stuck it out through some years of what stuck it out? You stuck it out until I finally came in and said, remember all those times I said, someday all this will be yours, Kayla. You’re all, yeah, I go. It’s now. I’m moving on to be part of a private equity group that’s rolling up HVAC and plumbing businesses and can’t do both anymore. I’ve got to burn the boats from my standpoint. And now’s the time you don’t need me anymore. And so, yeah, you end up stepping into that role of entrepreneurial co partner in the business to literally the person making all the decisions. You own the practice, the staff works for you. The office was yours, although it had my junk in it for an awfully long time.

Kayla Jimenez:
When you said, all of this is yours, you really meant that 1999 Dell monitor that I was working on as a law clerk. And it followed us to all the other law firms, and we still have it. All of it’s mine.

Dana Robinson:
All of it’s yours. We structured a deal, and you acquired my practice. And it’s been three years, I think, if I’m calculating correctly, since. And now you own an asset that at whatever point, you could merge that with a firm if you decide, wow, I want to go gangbusters, you can continue to have this lifestyle practice where you say, I get to pick clients I love to work with. And right now, I think that’s where you are. You’re choosing cases wisely. You’re enjoying the people that you work with. You’re teaching. You and I been co teaching, trying to get you to take the whole trademark law class next year. Wink, wink. And you’re able to teach at both law schools, which I know from when I did. It is a lot of work and requires some passion. It requires some time and agency for not having a real job. What’s next? Do you think you just plod along in the path of this perfectly balanced life that lets you travel, live where you want, and teach? You going to grow a big firm and have 50 associates working under you?

Kayla Jimenez:
No. Okay, so the scale thing has come up a couple of times. I think we even might have talked about it a long time ago. I don’t want to manage a ton of people that just. I love the law. I don’t want to do that business of the law, particularly. My goal, I think, is maybe to grow the firm with good client base, solid client base, demonstrate steady increasing revenue every year, and then eventually sell and then tag along to a large firm, just kind of keep shepherding the clients, and eventually retire from that and just teach because I do. I love the law. I want to keep my hand in it, but there has to be some sort of what’s next for me. And I think that’s it. Although I’m a terrible entrepreneur, because sometimes I’m like, do I really need to grow this? This is so great. I get to do whatever. So maybe I’m the worst person here that you interview because I’m not that entrepreneurial. Like, I’m going to grow it to a million. I’m like, no, just like, this is great. I love this. Let me just keep painting on the side at my sad little art studio.

Dana Robinson:
Actually, you bring up a really good point that’s common in the space where I’m playing now. So when I was part of a group that was buying air conditioning, plumbing businesses, you really are picking up someone’s business that had that. They hit a point where they go, this is what I can handle. I got $4 million a year worth of revenue out of that. I can produce this. The small staff that I have knows how to run this business better than me. So they build an asset, and then when they sell the asset, they make enough so that they go, that’s great. What? Their exit is fine. And others, when we buy that, we optimize. We combine it with other branches, we create shared services, we scale the business. And it’s not like they should have, right? We’re not doing them a disservice. And there should be no Insult that they never did what we do because they did what they should to create the life that they had for themselves. And when they exit, they get a retirement that’s not meaningless. I mean, we’re a lower middle market. Landscape maintenance transactions, pest control companies, blue collar businesses are transacting at three to five times profit. So you have business that makes you $600,000 a year in profit, that sells for $3 million. You’ve run a business that’s made you a lot of money, and you sell for $3 million when you retire. Or you could join another group and bolt in like you’re talking about, where you actually do get a bigger retirement because now you’re bolting your business into a bigger company that has scale. Or you could do it YOUrself. Of course, you and I know from just running the entire thing ourselves, even I’m not one who really wants a giant team working for me. The largest group of people, I think I’ve never had more than 30 on a payroll where I’m the executive, certainly owner of businesses with more than 30 on payroll. But not an operator. So I think your strategy is great and a great assessment of what you value and what an exit would look like for you. That’s smart. You have an asset that you could just sell to another associate or two or three, but you probably like another exit strategy is to bring it into a larger firm. They give you economics for that, and then they set you up for another exit out of the firm when you decide you’re done. And that’s a fantastic way to know that you can run this the way that you want to run it and grow it the way you want to grow it. And not everything needs to be massive scale for it to be meaningful economically, to give you the life you want now and the life you want when you retire. So I think it’s a great plan. Thanks for sharing it with me. I didn’t know that.

Kayla Jimenez:
Yeah, that’s the goal. Nerdy goal. But I know enough business brokers now who are like, you can get this amount and this value if you grow at this percent. I’m like, yeah, I could, man, or I could not. But my real passion, Dana, you instilled in me, which isn’t. I mean, it’s tangentially related to the law, but you got me into real. Like, I think that was, like, your greatest. I love the law firm. I truly do. But the greatest advice was use real estate as an investment strategy rather than you’re just buying your single family home. And it’s definitely the way I have built wealth, and I feel pride in the firm. But it’s different when you can physically see it, see what you’ve like. Oh, I put that kitchen in, and in the middle of the night, I laid that stupid brick. So real estate feels good, and to me, it’s, like, very tangible. So I appreciate you getting me into that entrepreneurial journey, and that’s kind of what I would like to focus on when I sell the or do whatever I do with the firm.

Dana Robinson:
Take your income, your profit from the firm, and buy another rental house, and then get a fix up and rent it again, and then buy another one. And then when interest rates fluctuate, you refi when they’re low. I’m not the genius of this. I talk about it in my first book, opt out. But it’s the brr method. The buy rehab, refi repeat, or whatever it is. The original rich dad, poor dad. I’m not the guru of that space, but, you know, from doing it, it works. And if you have a business that generates a life you want and some excess. You put it into that. And at whatever point you sell your practice, you’ve got paid off properties to live on besides the wealth you’ve created from the asset of this business that you own.

Kayla Jimenez:
Yeah, I really, really like that. So I feel know, Dana, when I met wanted, I think a lot of clerks have said this to you, but when I met you, I wanted to be like you. The goal was, hey, how do I get Dana’s lifestyle? He gets to go to Bali. He and Heather travel. Dana still has a life. He’s not like, sitting at his desk all the time with his head in his hands. Just sometimes when we have a bad case. And I wanted to know, how do I get that? And now, however many years later, I feel lucky to have gotten to the point where I’m like, this is great. Everyone’s got bad days and good days. But overall, this is exactly what I wanted. When I walked in your door and begged you to hire me for pro bono work, I wanted this life, and I have it, and it feels really good.

Dana Robinson:
Thank you. That makes me feel really good.

Kayla Jimenez:
Wow, that’s like a good wrap up.

Dana Robinson:
It is. And that full circle you should be incredibly proud of because you set out whatever that was 15 years ago. You were like that I can envision is what I want to do, and you set your sight on it, and you did it. And here you are. In the time since then, you have lived in Florence and studied abroad for fun and managed to pull off practicing and live in multiple states and multiple cities and grow your wealth through rental, acquisition, and rehab of rental properties. You’re doing all those things. And based on the fact that you and I can hang out and have a chicken bowl and catch up for an hour on a random day, you’re living the life that you envision that you would get to live. And that makes me proud of you. Not necessarily proud of me, right. I didn’t make that happen, you did. I just provided a model, and you leaned into the stuff that I did to make that happen. So I’m very proud of you. Congratulations.

Kayla Jimenez:
Oh, thank you, Dana. Yeah, it’s been a great journey, and I want to share. I’m glad you’re doing all the podcasts in the book, because if it influences one person to have a life, to get to the life that makes them really happy, then it’s worth one. I’ll just pick one.

Dana Robinson:
I don’t know if you were there. I’ll use this as my final little TED talk, and I’ll drop the mic every year. Because I’ve been teaching law school for twelve or 13 years, I pick one session where I spend as much as an hour kind of given a pep talk that I’ll say is not a very good pep talk. It’s a reality check, because I used to get a lot of office hour requests where they’re like, how do I get to do ip law? Or how do I get to do what you’re doing? And repeatedly, I’d get a lot of people that are like, look, what I really want is a lifestyle business where I can have a life and have a family and save and get ahead and invest. And they kind of paint this picture and they say things like, well, I could never work at one of those big firms. They just grind you out. They grind, grind, grind, and blah, blah, blah. And so after hearing this multiple times, I give a lecture where I talk through a lot of the things you need to do to gain control over your career as a future lawyer. But the number one thing I say is if you can get a job at someplace that has highly concentrated work in the area you want to work in, and they’re going to grind you out, you should take that job so fast because you only need it for two years, three years. I mean, I did my 2200 hours a year for four. I wouldn’t have the expertise that I have. If I hadn’t, if you hadn’t gone between me, the other job and coming back and working with me, highly concentrated, lots of hours, lots of stress, you wouldn’t have those skills. You don’t just get to walk into a job and say, I’d like a big salary and I’d like to not have to work that hard, and you have to bring value. And if you don’t bring value to your clients, they don’t pay. If your firm doesn’t get value out of you, they can’t pay you. So my pitch is, always take the hardest job you can get right out of school, especially if it’s in an area that you have some passion around or some aptitude around. Go do that. Don’t ask for a lifestyle job. Create a lifestyle life. And that happens from spending two to four years working really hard. And you did it with me, you could have done it with any firm. And then you have some agents. So you can leave, you can start your own thing, you can work for a smaller firm, you just open up the doors, and then you get the life you’re talking about. You set your sight on it, said, I want to have that life. You did it, the 15 year overnight success.

Kayla Jimenez:
Yeah. But it was worth it. It was worth it. Yeah. And looking back, I don’t think I would have done anything different. I think it was perfect. It was exactly me. And maybe that’s entrepreneurial is, you know, you, you’re true to yourself and you just go for what you think you can achieve because you can.

Dana Robinson:
I love it. That is a perfect wrap. Thank you, Kayla. Appreciate your time. And for those that are listening, thank you. kayla@usiporneysplural.com. If you want to reach out for legal work, she’s not a life coach, although she’s probably got good advice based on what I’ve heard here, practicing in the area of intellectual property, small, corporate and medium work. And this is Dana Robinson.

Dana Robinson:
As you all know, reach out. My team filters emails, but they all come to me pretty quickly. Hello@danarobinson.com. Email me anything you want to talk about, questions, things I can talk about on the air. I’m not going to give you legal advice for free, but I’d love to hear from you about what else we can bring on the podcast. Thanks, everybody.

Kayla Jimenez:
All right.

Dana Robinson:
Thanks for joining me on this episode of the Exit Plan podcast. I’d love to hear from you. Feel free to hit me up with questions or comments by emailing me at hello@danrobinson.com or leave comments and questions by calling 858-252-7785 call 858-252-7785 and leave a message. Close.