Episode 13: The Honest Truth About The Highs And Lows Of Running A Business w/Joel Ankney

My guest on today’s podcast is Joel Ankney. Joel is the founder of Ankney Law- a successful law firm specializing in helping entrepreneurs buy and sell businesses, as well as commercial real estate transactions and small business support. What is unique about Joel is that he was elected Top Attorney in Coastal Virginia and even his peers selected him as a Virginia Legal Elite attorney multiple times. What is even more impressive though is his humility and honesty in this conversation as he discusses his highs and lows including anticipatory anxiety that comes from running a business even today. In this episode Joel speaks about what it was like making the jump to starting his own practice at a time in life when he and his wife had four boys ranging in age from one to thirteen. How he and his wife prepared and what it was like in those early days navigating client acquisition and marketing. We talk in depth about marketing including how Joel has self-published a few books and how that has propelled his law practice by positioning him as an authority in his niche field, while also allowing him to discover new pieces of himself and finding a passion for being an author. And be sure to listen to the end as Joel shares how he defines success today, and how his definition of success has been fluid and has changed throughout his career. So with that introduction I hope you enjoy this episode of the Self-Employment Success Podcast with Joel Ankney.

LINKS

PeaceLink Financial Planning
Ankney Law

TRANSCRIPT

Leland Gross CFP (00:01.198)

All right, welcome Joel Ankney to the Self-Employment Success podcast. Excited to have you here. Thanks. I'm excited to be here. We've already started, and it's been wonderful. So I'm glad we're recording now. Yeah, I know. We had a great conversation, honestly, leading up to recording, and then had to make ourselves hit record. So tell the listeners, let's just dive in. Tell us a little bit about yourself, what you do, what your business does, and kind of where it stands today. OK, great. Yeah, so I am an attorney.

I'm a transactional attorney, a business attorney. I started my career as an attorney with some large law firms in the United States. And years of working at the large law firms, and it's a long story and there are a lot of reasons, but I decided I needed to do something else. And I had this idea for years sitting in the back of my mind that I wanted to open my own law practice.

And so, yeah, I left the big firm about 20 years ago, opened my own law practice that focuses primarily on purchase and sale of small businesses, business startups, and then just advising clients on business matters. And we've been going strong for about 20 years now. That's amazing. 20 years, I was 10, which is not, you know.

is what it is, but that's amazing. So, okay, so you come out of college yourself, you are working for these big firms, and then just decided one day, like, I want to start a business yourself that works with other businesses. So I guess, as a business owner who serves businesses yourself, how did you find your way into that? When you launched your practice, was that the desire day one to do, you know?

business purchases, business transactions, helping small business owners? So kind of yes and no. So I have grown up in a family of small business people. So one of my grandfathers owned gas stations, and I remember being around him. And then my father owned a general contracting business, kind of a handyman business, but in the Georgetown area.

Leland Gross CFP (02:25.542)

of Washington DC, so lots of very high-end clients. And so one of the things I had done with my, you know, my father was always very gracious to employ me when I was either, you know, without a job or in between semesters or things like that. And one of the things that I had helped him with, or I say helped, I don't know how much help I was, but that I worked with him on was a

renovating row houses for real estate investors and then watching them flip those houses. And so when I decided that maybe law school was the right thing for me, I went into law school with the idea that I wanted to help people like my father and my grandfather and also perhaps was interested in that real estate investment side of things as well. So that was always kind of my motivation when I was went to law school.

course, when I got out of law school, that's not what I did. I worked for some very large firms doing some very large transactions and business work. And that was great. Loved it got trained very well, was given a lot of responsibility early in my legal career. And and I think that helped, you know, me with a couple things. One was, maybe I was overly confident that I could do this on my own. But also

felt like I had been, I mean, it's a little arrogant, right? You feel like, hey, if I can do this at the big law firm, then I'm sure I can do this on my own for smaller businesses. So a lot of self-confidence because of the experience at the big firm. Yeah. Someone in my life who I really respect, when they were having their first child, I asked them, like, are you nervous? Like, you're gonna be a dad. And he was like, sometimes.

But then I have to realize way stupider people than me have done this and survived. And I had the thought of, that sounds arrogant, but really it's kind of true. And there's a confidence that is required any time you're going to venture into the next thing. I think every entrepreneur has to have a high level of self-confidence of, all right, I think this is going to work out. In order to be able to withstand the risk and the highs and the lows, there has to be some sort of level of

Leland Gross CFP (04:48.718)

self-confidence. I think there does. I think the two, I mean, I had never, you know, I'm afraid every day. I hate to kind of admit that. But, you know, there are concerns, worries and anxieties that come along with running your own business. And so, and especially at the beginning, boy, that was really scary to take that leap and then to kind of slowly develop the law practice and develop the clientele. That was really, you know,

kind of an issue that I hadn't really thought through a lot. Like how was I gonna get clients? And so, you know, you hear things like fake it till you make it. I mean, I think you gotta fake it a lot. You hear about imposter syndrome. I mean, I certainly could, you know, I relate to a lot of that. And, you know, I find myself in situations even now where I'm like, you know, I wouldn't have.

I couldn't have imagined myself in situations like this, and yet here I am, and what do I do? Just smile and keep going, right? So. Yeah, so what did that, I wanna reflect on that for a minute, because I think everything you just shared is very real, is very human. Even just the balance of, I can do this on my own, but then also the terror of like, I'm doing this on my own. And.

and the imposter syndrome and I call it the head trash that comes in that tells you you're not good enough or you know they're gonna find out or like no one will pay you that fee. And for you bringing on new clients what did that what did that look like? Like you opened your doors day one. Did you were you married? Did you have kids? Was there a spouse working? Like there's so many layers to what the dynamics look like.

So, yeah, lots of answers. Definitely, my wife and I have been married for, I think it'll be 37 years this August. Congratulations. Yeah, thanks. And we have four children, all boys. And at the time that I opened my practice, my oldest son was 13 turning 14, just entering freshman in high school.

Leland Gross CFP (07:12.302)

And then all the way down to, I guess the youngest kid was a year old. So, yeah, so that was obviously very scary too. I think I get a lot of confidence from my wife for sure. I mean, probably about a year before we opened the practice, I came home and was just very, you know, down and kind of frustrated and she's the one who said to me,

If you could do anything, what would you do? And I said, well, you know what? I've always kind of had this thought in the back of my mind that I could open my own law practice. And then she said, well, what, what will that take? And I said, well, I think we need to have X number of dollars in the savings to kind of carry us through. So she said, I'm on it. And, um, you know, one of the fortunate things about working at a large law firm is they compensate you quite well.

So Jennifer was amazing at kind of helping us manage our money very well. And so it took us close to a year to save up enough money to feel comfortable to launch. And so and that was a painful year for me. But we had a goal. And in fact, we never got I don't think we ever make it made it to 100 percent of our goal. I think we got to about 80 percent. And I came home and was again just.

distraught, kind of downtrodden, and she said, I think we have enough, let's do it. And she went out and found me office space and, you know, helped me kind of plan on how to do this. So, yeah, very scary. Lots of things going on, you know, fairly newborn child, kids in high school, middle school, and elementary school. So you had a kid at home, elementary school, middle school, and high school? Yes. All of them.

And you decided to start a business that takes guts. I got. Yeah. But again, because of my wife's preparation, her plan, I felt like, you know, financially, we had enough money for us to last for a period of time. One of the you asked, like, how do we find the clients? When I resigned at the law firm, the partner that I worked for said

Leland Gross CFP (09:38.138)

Give me a list of all of the projects that you're working on right now. I'll send a letter out to those clients and ask them if they want to stay with us or if they want to go with you. I think ethically the law firm is supposed to do that. But as a result of that letter, I had about 25 clients come with me. Now not all of them had work immediately.

But I know the day that I opened my doors, I probably had one or two hours worth of work to do for clients. And then, so those 25 clients were really the foundation for, so I mean, it doesn't sound like when we talk about it, it doesn't sound like I took as big a leap as maybe I felt I did, right? Because I had planned well and saved up quite a bit of money and then I was able to, I didn't know it.

that there were going to be 25 clients who would come with me. But they did, they came. And probably of those 25, maybe five or six of them really ended up to be solid, you know, clients who gave me work over the next three to five years as I started to build the practice. And I still think that was a major risk. I don't think that discredits you at all, because again, you didn't know if they were coming. And I really think ethically, that's awesome that the law firm did that. Right.

in the financial advising world so often it's, you know, right, non competes, you can't even talk to anybody. We're gonna like sweep this under the rug and you're on your own. And so that's really amazing to have someone ethically say like, Hey, well, you are the relationship with these people. So we'll give them the option. And what a gift to have your doors open and be like, Okay, I have savings and I have something coming in, like I've got clients to work with. Right. But now you're also wearing

all the hats, you're not just the lawyer, now you're the business owner, the marketer, the, you know, all pieces of this business. And what was it like balancing those hats? Was your wife working in the practice with you or was it completely Joel's shop by himself? So Jennifer's always helped me with the practice in one way or another. So, of course, when we first started and we had all these small kids,

Leland Gross CFP (12:01.654)

you know, she helped me get set up and then, you know, she would help me with things along the way. But really once the kids, I mean, all my kids are in there, you know, range from age 21 to 33 now, I think. So once the kids, the youngest kid, I think, got into middle school, she really started to work in the practice more, helping me with a lot of the administrative.

aspects of it and the marketing as well. You know, before she really was helping me with that, yes, I think I well, I should have worn those hats. I think a lot of those hats just hung on hooks on the wall. And so, you know, that's the one thing I thought, look, if you're just a really good attorney, like things will just happen, right? People will just come to you. And

you know, I found out that that's not necessarily true. I also found out that there, like you said, there's just so much administrative stuff to do in connection with running your own business that, I mean, in a way, that's always been, you know, something that I just kind of dislike about, you know, what I do, but it's a necessary thing, so we do it. Yeah, and I find that when I talk to other entrepreneurs, people go one of...

ways. They either love business and love running a business and they are fine with whatever the business does, but they'd rather be in the administrative like spreadsheets and business finance and marketing and where are we going side or they love working in the business. They love what the business does and then they get hung up, not hung up, but they're just like, this other stuff is more

feels like an anchor in the wind than what brings me to life. And so rarely do you find someone who's both, who's like, I love working on the business and in the business. Yes. But most of the time, especially when you're first starting off and you don't have a team or staff or anything like that, you are running both of those. Yes, yes, yes. Or you find, I mean, I was fortunate to find a CPA who helped me out.

Leland Gross CFP (14:25.134)

quite a bit when I was first starting. I mean, I just had no idea about anything about accounting or how to handle bookkeeping or anything like that. I just had no idea because at the big firm, we had an accounting department and they took care of everything. All I had to do is make sure that I was giving them the data that they needed, the hours and the descriptions of what I was doing and which clients I was doing it for. And then they did everything else.

They build everybody, they collected all the money, they did everything. They did the payroll, we had a HR department. All of a sudden, I had to learn how to do all that stuff, even though there was just two of us essentially, but we had to figure out, like you don't like to get letters from the IRS telling you that you missed a filing or a payroll tax payment or something like that. So, yeah.

Yeah, I think it's good to I'm not great at it, but I think it is good to try and find the right people to ask questions and to maybe help out and to spend a little money. I mean, I at the beginning of my practice, when I realized that I didn't know anything about accounting or bookkeeping, I called up this CPA who was referred to me and I just asked her, I said, hey, can you come to my office? I'll pay you for like two or three hours of your time.

I have just a list of questions that I just want to go through. And she was wonderful. She came to my office. We went through all my questions. She helped guide me through it. And I really still was, you know, still felt a little overwhelmed by it. But at least I had a great resource that I could use. And she helped me probably through the first three or four years of my practice with stuff like that. I want to echo that point because I think it's really important.

start businesses and our income isn't where we want it to be. We want to be as lean as possible. And that's kind of like your knee-jerk reaction is don't spend money. Spend only on what you have to. But I do believe there is a place where you have to spend money to make money. And just being willing to invest in your business and being willing to say, okay, I need help with taxes and with bookkeeping. That is very important. That is.

Leland Gross CFP (16:41.154)

foundational to having a healthy business. And so being willing to find the people, and like you said, whether that's internal and you have an accounting department or you just hire an accountant, that doesn't matter as much as just saying, hey, I'm willing to invest not just the time and like blood, sweat and tears, but also being willing to pay for that and say, can I pay for a couple hours of your time for you to teach me how to do this? Can I?

because you know what your business does, but again, you need help on the other side of things. And I think a lot of times that piece of it intimidates people from starting their business. You know, what is this gonna be like? I don't know how to run a business. And just realizing like you can do it. You don't need to know every, you don't need to be a business expert to start a business because there are business experts that can help you on that side. One of the things that I really was

I don't know how to describe the emotions. Surprised, a little shocked, is that when I started to ask around different friends who were at either small law firms or had their own law firms, I found that the community was extremely supportive. Like I had a couple of, I had one friend who...

I have worked at the big law firm with me, actually knew him from law school. We worked at the same law firm for many years, and then he left and started his own practice. And he was so wonderful. We went to lunch and he actually printed up and gave me a copy of his profit and loss statement for the previous year so I could see like what expenses I was like just categories of expenses that I was going to have to cover. And that was just so I, you know.

It was very transparent of him to allow me to see his dollar figures as well. But just knowing, hey, you need to plan to cover these types of expenses. And then I had another friend who, you know, we probably went to lunch five or six times and he was just so encouraging about, you know, you can do this and here are some things you need to think about. And so I found that.

Leland Gross CFP (19:00.042)

And even to this day, I've always been very grateful for the support that this what I would call the small firm community has for each other. And, you know, I try and give that back as well with other attorneys, especially younger attorneys who are thinking about, you know, striking out on their own or who are perhaps discouraged at the experience that they're having at a big law firm or something like that. So, yeah, it was surprising. I mean, the big law firm.

At least the firms I worked at were very territorial inside, very competitive, very kind of zero sum game approach to things. But in the small firm community, it was just completely the opposite. I can pick up the phone today and call, you know, three or four different attorneys around town that just ask them. Like I had a friend of mine call me the other day and just say, you know, I've had my own dedicated facts.

line for decades and I want to know what you do and I'm like, oh, well, this is what I do. I have a virtual fax number. I get like one or two faxes a year. Interestingly, the IRS still bases. Yeah, they don't do emails or anything. It's just fax. But I'm like, it's so cheap that it's easy to and so I know I can call people like that and just ask them, you know, what are you doing here? What's going on?

kind of help with substantive questions, but also help with just management questions, like business management questions. What are you doing? How do you handle this? And what does it cost you? And everybody's very, very supportive. So I think that was surprising to me that there are so many people out there who are happy to help. Yeah. I'm struck at how similar that has been to my experience.

in financial planning, a lot of the big firms are very, and that's not to say all big firms in every industry are bad. Right, right. But in my experience, the big firms are very territorial. They're very like zero sum game and not willing to kind of divulge their secrets or there's not much of an abundance mindset. There's a lot of scarcity we have. There's not enough to go around. So what's ours is ours. And then the small independent practices, there's totally an abundance mindset.

Leland Gross CFP (21:27.214)

It's like you're just not gonna have a monopoly on the entire city as far as financial planning goes. So like, of course I'm willing to share my thoughts, the processes I do, the substantive questions and the just practical questions of how are we doing this? And I feel like that's been instrumental in my practice as well, just getting started is having people who you can call and say, hey, I need to do X, Y, Z thing and I can't figure out how to do it. Or what do you use for that? Or.

technology do you use? Has anybody figured out a solution for this? And it's so helpful having a community. And realizing that, like you said, people want to help, especially people who've taken this journey and have gone through the ups and downs themselves to go independent. You turn around, you're like, of course I want to help someone else navigate that journey because it's so impactful for me and I want to pay it forward. So,

What has client acquisition looked like for you? Did you start off saying, these are the types of clients I want, so those are the only ones I'm gonna take, and if someone else walks through the door needing some other type of law, we're just not gonna do it? Or did you say, okay, well, we'll take some of these people to get revenue going, and then kind of niche down further from there? What's that journey been like for you? That's a great question. I mean, it's somewhere in the middle of that spectrum.

You know, so I definitely had an idea of the types of work that I wanted to do. But I also thought that there wouldn't be enough of that work out there for me so that perhaps maybe I should expand my offering. So I did initially decide that I would expand my offering a little bit. I got a couple of projects and I quickly realized that I was in the deep end on those projects and it wasn't worth it to.

spend the time and I to try and figure it out and because anyway what I mean by that is that I've always been a business attorney but I thought I should maybe expand to employment law because I had done a little bit of that in my business practice but one of the first cases that I received was from somebody who had a discrimination case against their employer and

Leland Gross CFP (23:54.654)

And it was a discrimination case based on a policy in that employer's handbook. And it was an employer who was a large national company. And we essentially got our faces ground into the ground. I mean, we settled it, but it was very, it was just not a great experience for me or for my client. And so I just knew right again, you know, I mean, one of the things I think about, one of the things I love about having my own

business is that I can experiment and I can pivot very quickly. And so, you know, we had that bad experience. It was very evident to me that, um, it just was not going to be worth it to try and spin up that aspect of a, of a law practice. And so I dropped it very quickly. Um, but client acquisition has always been, I mean, I would say almost all of my client acquisition comes from two sources. One is it's referral. I get referred,

And my referral sources typically are accountants and other attorneys, interestingly. I mean, I get a lot of referrals from trial attorneys who don't want to do the business. Or they, it's just, again, it's out of their scope. And so they trust me to do it for their clients, knowing that I'll not take those clients, that I'll give the clients back when we're done.

I think the other client acquisition.

Leland Gross CFP (25:29.906)

about this before we started recording, but self-publishing a couple of books already has been the most powerful marketing tool that I've ever had. So I've tried other things. You know, I've tried to do free seminars at the public library on how to start a business. I've tried to, I mean, I run a blog. I've actually run several blogs in the past. I have a YouTube channel and those are all great. I think you have to have those types of content.

offerings but really I don't really get any business off of that. It's really more of a client management tool where if somebody asks me a question I can say you know what I have a blog post on that I'll just send you the link or I have a YouTube video on that and I'll send you the link and if you have any more questions just let me know kind of thing. When before this recording we were talking a lot

how that's just a path that I feel like, similarly, people feel intimidated. What, how do I write a book? How do I publish a book? But it does quickly show a level of authority in your field. Oh, yes. And that gives a lot of credibility to then have people reach out and say, well, you wrote the book on this, so I want to work with you. So you started off, you kind of said, I'm going to keep my horizons a little wider.

for the thought of will there be enough people with this specific need? And then realize some of these wider offerings were taking a lot of time and energy and weren't as life-giving to you. And I love what you said about being able to pivot. Like owning your own business, you can kind of say, well, we're gonna change our service offerings. We're gonna change how we do this. And that's a freedom and flexibility that is so refreshing. Would you say still there's...

have you, I guess the question I have is have you debunked the thought that there are not enough people with that specific need that you wanted to serve originally? Or do you still feel like, yeah, there's not enough people needing help buying businesses and starting businesses that I have other service offerings in the mix? Or have you pretty much gotten into that, you know, all right, I have this field within the field that is really booming people wanting to start their own businesses. And that's keeping

Leland Gross CFP (28:00.142)

Right. Be busy. Yes. I mean, we've gotten to a point where, in fact, I, you know, every year when I renew my malpractice insurance, I have to give them a percentage breakdown of what I do in my practice. And so I just did that two days ago. And so, you know, I know that 54 percent of my practice is small business purchase and sales work. Another I think it's 17 percent or so is commercial real estate.

purchases and sales. And then the rest is just helping people either start a business or operate their business. Maybe they need a contract for this or that or they need something reviewed or they're bringing in a new owner or an owner is exiting or you know, they have a question about how to how to collect money from a contract with a customer or something like that. But yeah, I mean, definitely have

absolutely created a niche at this point and just wake up every couple of days with my fingers crossed that it'll remain strong. So we talked a little bit about before we started recording that one of the things I'm kind of riding is this trendy kind of popular idea of rather than starting a business, finding a business and purchasing that.

that ongoing business and then running that business, either growing it or... And that's a very trendy thing right now. And I happen to be kind of in that whole mix because of my first book. It's kind of become one of the books that a lot of people in that community read. And so I could have never really predicted that, right? I couldn't have predicted the trend. I couldn't have predicted that my book would have been picked up by the community, but it has been, all that's worked out. And so...

you know, now a lot of client acquisition is essentially people who buy the book, read it, and then call me up and say, Hey, I'm about to do this transaction, this purchase. Would you be willing to represent me? And that, I mean, you know, that's like a dream, right? Like that's, you know, and how did I get there? I'm not entirely sure because I didn't do a huge amount of marketing. I really did almost no marketing for my book, right? I tried to do some grassroots things, but,

Leland Gross CFP (30:27.522)

But it's really because the community, it's called the entrepreneurship through acquisition community. I mean, the stories are just crazy, right? Like I had a, five years ago, I had a professor at a business school at a large university ask if he could use my book in his class and then invite me to guest lecture. And he had other guest lecturers who had books as well. And they, so now if you go on Amazon,

Like the other author does tons of marketing and everything. And I just ride those coattails because our books are often bought together. So it's been, it's been, I couldn't have predicted any of that, but, uh, that's been my biggest client acquisition tool. That's amazing. And the dream to just find yourself in one of those communities where, again, you're the authority to this community and everyone is excited and writing.

this high of, yeah, I also want to buy a business. Here's a community that does that. Oh, this community recommends this book. Oh, right. Here's Joel. Right. Is is amazing and amazing how that got picked up at universities. Yeah. But the idea, the book and we could have a whole other interview on how I decided to write the book and how I came up with the idea for the book and then the process and everything. But really.

Like you said, it's such a unique offering. So a lot of times when I go to networking events and I introduce myself, I introduce myself as an author and an attorney. Nobody, there are gonna be other attorneys there, but there's typically no other attorney there who's written a book. And so that is just a great conversation starter. And I had an attorney years ago, when I first wrote the book, he said, well, how much?

How much does it cost for you to purchase the book at your author rate? And it's like a little over $3. And he's like, you ought to be handing these out like business cards. And I thought, yeah, what a great idea. So I carry them wherever I go and I hand them out to people and things like that. You just never know. And that's one of the great things I think about owning your own business is you can try all these different things. And if something hits, you just run with it.

Leland Gross CFP (32:53.358)

I love the networking image of I'm an author and an attorney, because in finance, we say like, if you want to kill a conversation, if you need to get out of the conversation, just answer, I'm a financial advisor to that question. People are like, don't sell me life insurance and they run the other way. But so there's pieces where I'm like, how do I introduce myself at a networking event to start a conversation? Yeah. Being able to say I'm an author. Right. I mean, immediately is. Right. Really.

What do you write? Yeah. What books have you, like, Exactly. It's just, there's an immediate spark of curiosity. And people will, like, if you wrote a book about some aspect of what you do, people then don't really care as much about, you know, that kind of that, what would you call it? That obstacle, that introductory fear of, oh no, they're gonna sell me something. Mm-hmm. That you've changed the whole kind of flavor of the conversation.

And people, they don't care that you're a financial planner anymore. Now they want to know, even if you say, well, my book is about how to help small business people plan for an exit when they retire. You know, then they're all like, well, I'm a small business person. I would love to know that the answer to that question. Right. My book is going to be about how to sell you whole life insurance. Right. That's a joke, everyone. I don't do that. That's awesome. I love that. So what?

surprised you the most about this journey of from having that conversation with your wife to now. What has surprised you the most? Well, surprise is I think that I don't know if it's surprised, but I was just unaware, just naive about the amount of work it would take to run the business, to keep the business running. You know, it the amount of administrative stuff

is, and it's just tedious, right? For me at least. I'm not, when you talked about those people in those two different camps, you know, I'm a technician essentially, right? I love to read, write, research, advise people, things like that. And, but then to have to sit down and do tax forms and filings and payroll taxes and just all kinds of administrative, you know, whatever. That was surprising.

Leland Gross CFP (35:20.074)

I think the other surprising issue was just like you talked about client acquisition, just marketing, just the sheer amount of effort and work it takes. I've had people, for example, even though I've had great success with my book, I've had people approach me to try and help me, sell me essentially on, hey, you should set up an author website that would be a sales funnel that would bring more

And I look at that and I'm like, I don't want to take the time to do that. And I'm not really a salesperson. So having a click funnel is not something that, I mean, those turned me off, right? So I'm like, I don't want to turn off other people. I mean, we're doing okay. And they're like, yeah, but you could be selling so many more books and you could be getting so, I'm like, I don't really need to. I'm happy for the moment. So marketing has been a big surprise, I think.

really big surprise. And what was the low point for you? It hasn't come yet, I don't think. That's great. I asked my wife that question last night and she talked about the challenges with marketing. But she's a marketer, she has a marketing degree and that's great. I mean, she's like an amazing resource. But for me, I think the low point is

is anticipatory at this point. Right. So I'm in my late 50s and, you know, something I wrote a letter the other day where I had to remind a client of a deadline, but the deadline is 10 years from now. And I just thought to myself, gosh, I hope I'm I am I going to be the one doing that work 10 years from now? That filing when the when the when the deadline comes, I'll be.

68 years old. Gosh, I don't know. That worries me a lot. Right. So that's the anticipatory low point is, what's my exit going to look like? You know, I don't know. Right. And I don't, and I worry that I've put so much sweat into this business that I might just have to walk away without getting any value out of it. And that's a big concern. Right. Like how do I, how do I exit a small law practice and at least get a little bit of value out of it? Yeah. So.

Leland Gross CFP (37:44.598)

that is for so many people, we're so focused on starting the business that you're now on the back end of what is leaving the business going to be like. That's even scarier now than anyway. I'm sure it is. I can only imagine because you, I was listening to another podcast recently where they talked about your business and when it transitions from just an income stream and a service you provide to an asset. Right. And well, now this is an asset that...

I want to be able to sell and make money off of, or get some sort of value out of when I leave. There's a different mindset. You shift the mindset of even how you're running your business and how you think about your business when it transitions from this is just me doing my thing as a service to create an income stream to now this is a business. It is its own asset entity that needs to live on beyond me.

I love that because I think that's where you've kind of pinpointed where I'm at is in that phase of trying to turn that service business into an asset. I don't think I'm quite there yet. Right. Like I think that that's the challenge over the next, you know, five to seven years is can I take all of the kind of goodwill that I've built up in my own personal brand and turn that into an asset that I can convey.

you know, sell or transfer to somebody else. I don't know. Yeah. So that's my anticipatory low point. Makes sense. Hopefully that low point never comes. But I resonate with even just like the anticipatory anxiety of that, like what the fear of what that could look like in the future. So this is a podcast about success. And if you pull anybody on the street and ask them

what is success, you'll get different answers from different people. So for you, how do you define success and how will you know if or when you have achieved it? That's a fluid question or maybe a fluid answer, right? When I was, I opened my own practice when I was 38 years old and my definition of success then was different. And because I think it was

Leland Gross CFP (40:07.382)

driven by my needs, right? I had four children. I had a need for a certain revenue stream, a certain income. And so at the time, success was defined more as by putting a dollar value on it, for example. But in the last maybe 10 years, and especially the last five years, really success to me is...

really equates to freedom. You know, freedom to do what I want, to dress the way I want. I mean, you saw me walk in today and, you know, to wear vans to the office. But also to do things like decide to write my own book and to not have somebody say to me, well, you can't do that during office hours or, you know, we need to review that book before you publish it to make sure it has the right message in it and things like that.

the freedom to work wherever I want to work. When COVID hit, I moved my office. I got rid of the traditional lawyer's office with the cherry wood furniture and everything and moved my office into my house. And certainly I keep a space here, an office here at this, we're in a coworking space right now, but that's mainly to have access, a mail drop, access to conference rooms for meetings with clients, but I'm rarely.

here working in this office. So I work at home almost 98% of the time. Or I work on the road somewhere. It wasn't really a vacation. It was supposed to be a vacation. But I went to the Outer Banks in April for a week with my family and friends and ended up closing two transactions while I was there. That wasn't very pleasant for me. But at least nobody knew. Nobody...

on the other side knew that I wasn't in my office. So, and I didn't have a boss telling me, hey, you can't go on vacation because we need you here in the office to close these transactions. So I love the freedom of being allowed to create whatever I want. You know, I have had ideas for, I have other books that I've written. I have, so that's success to me is that freedom, that freedom to be myself, to do the things that I wanna do. And I resonate with that.

Leland Gross CFP (42:30.558)

so deeply, but I also love your first thought of that success is fluid. Different seasons of life success, the definition of success changes, and how even once you achieve that success the bar is almost pushed back to the next level. I love that. Like, I haven't thought about the fact that will you actually just achieve a place where you're like, I've arrived? Probably not, because there will always be another...

or stage of life or, you know, piece of the puzzle that comes up. They're like, well, now I have the dollar amount, but now I want the freedom. Right. Or, you know, whatever that may be. Yeah. And you discover yourself along the way, too, I think. You know, I, you know, I had this idea years ago that I wanted to write a book, but I didn't realize until I wrote the first book and published it how much I enjoyed being an author.

I mean, this sounds really kind of superficial, but I mean, it's kind of fun to be, you know, to kind of have that reputation as being an author and being somebody that can say, well, I've sold, you know, this many thousand numbers of books and I've guest lectured at the Columbia Business School and things like that. I mean, that's a little bit of an ego stroke, I guess. And that's not really what I'm ever after.

But it helped me discover a little more who I perhaps am and what I enjoy doing, what kind of creativity I like to be involved in. And I think that's a part of success too, that you discover yourself along the way, you discover what you like, what you enjoy, and what ends up being defined as success for you. Amazing.

Well, we're going to have to have you back on the podcast because you have so many thoughts. Oh, I would love to. We interviewed Joel Lawyer today. We're going to interview Joel Author next time. Oh, yeah, I would love that. Yeah. Next time. Well, thank you so much for being on the Self-Employment Success Podcast. Thanks for inviting me, Whelan. Thanks.