#167: Success, Happiness & Being Human with Scott Oliver

​Well, hello, hello everybody. Welcome back to the Life & Law Podcast. This is your host, Heather Moulder. Today we are speaking with Scott Oliver.

He is a partner at Lewis Kappes who represents banks and non bank lenders in SBA transactions nationwide. Scott became the youngest equity partner in his firm’s history after closing thousands of SBA loans and has counseled clients at every stage in the lending process. But that is not what we will be chatting about today.

I became aware of Scott thanks to his insightful and engaging LinkedIn posts. Sometimes he comes from a business development angle, but most of the time he writes about life – life as a lawyer, life as a lawyer parent, and how to support the human side of practicing law. This is what drew me to him, and it’s why I invited him onto the podcast today. Welcome, Scott.

[00:01:52] Scott Oliver: Hey, thanks for having me, Heather. I really appreciate it.

[00:01:54] Heather: Well, as I said, I absolutely love what you post about on LinkedIn, even though I’m probably not the best about letting you know on LinkedIn, that needs to change. I’m going to try to become more engaged on LinkedIn the remainder of this year. It’s a goal of mine.

But I love that you come at it from the perspective of: you’re a lawyer, you’re a practicing lawyer, but you don’t just talk about the law. You don’t just do it for business like obvious business development purposes. I mean, some of it is, but most of it really isn’t.

And I love that you support, especially like young lawyers. I notice a lot, like a lot of your posts are really aimed towards, hey, I remember what it was like. And here are the lessons I’ve learned along the way, which, by the way, I’m sure some of those are even speaking directly to people who are more senior, because sometimes we don’t learn those things very quickly. But I love it.

And so I wanted to get you on the podcast today and talk a little bit about that and how you kind of got started on LinkedIn and why, and, you know, what you’ve gotten out of it that isn’t just pure business development related. Because I think. I think sometimes when we think of it as a business development activity, I think this is sad to say, but it’s true. It’s not enough.

It’s not enough of a reason for a lot of people to do it. And the good news is, there’s a lot more to it than that, and there are a lot more benefits that you can get from it. So that’s just some of what, a little bit of a preview of what we’re going to get into today.

But before we get into all of that, I’d love to hear a little bit about, like, why did you become a lawyer? What made you, when did you know? How did that happen? And what was your trajectory to where you are today?

Why Your Reasons for Becoming A Lawyer Don’t Have To Matter (Even if You Chose For the “Wrong” Reasons)

[00:03:39] Scott Oliver: Yeah. So I actually get that, that question quite a bit, because you’ll get people who say, oh, you’re a lawyer. That means you like to argue. When you were a little kid, your mom said, hey, you need to go to law school and be a litigator, or something like that. And quite frankly, that was a little bit of it.

But the truth of the matter is, I wanted to become a lawyer initially for all the wrong reasons, or I guess maybe the right reasons. It was because of a girl who is now my wife. Right? So it worked out.

But in high school, I kind of, you know, was, was floating around, didn’t really know 100% what I wanted to do. I had thoughts in my mind about wanting to go into medicine, but there weren’t really reasons behind that until I met my now wife at that time, who was just a friend, who said, I want to be a lawyer. And I said, well, that sounds interesting. Well, let’s check this out. I’m going to tell her I want to be a lawyer, too, so we can have something in common. Right? So I did that.

And lo and behold, after a while, I figured out this lawyer thing might be a real career path, because everything that I would research at a young age was saying, hey, if you have these writing abilities, if you like research, if you like reading, if you like speaking, if you like communication skills and all of these things, this might be a fit for you. And I said, these are all my favorite things. This is great.

So over the course of that year, leading into my senior year, I started to think, well, maybe I do want to go to law school at that point. Started researching, what does it look like to be a pre law student? What does it look like in undergrad to become an attorney? So I started taking very intentional steps along with that girl to become an attorney at a young age.

Over time, it kind of snowballed. And I said, this is the perfect fit for me. I love everything about this profession. And, oh, by the way, I can mix business with law and eventually own part of a law firm. And to me, that was very, very appealing.

So ever since that point, I was very strategic in what I did, what the courses I took, who I spoke with, the experience that I had internships leading up to law school, and found myself in law school loving every second of it with my wife and taking the bar with my wife, figuring out that, hey, this is actually a pretty great place to be. And I do enjoy almost everything about practice.

[00:06:01] Heather: Okay, so there’s a couple of really interesting things in that story. First off, I’ve never had anybody answer that way because of a girl or because of the person who one day became my spouse. You know, you’re a first and maybe the last that I’ll hear that from.

Being Strategic & Intentional (Once You Decide)

I think it’s interesting, though, to note that you were actually very strategic about it from the very beginning because you said something “that sounds interesting. Let me look into that.” Then you researched, what does this mean? And you started to realize, well, here are the skills that are utilized. Well, I like doing those things.

And so you were pretty strategic from the very beginning.

And I do think that some lawyers, there’s a lot of lawyers who become lawyers almost by accident. Right? We do it because we hear we’d be good at it. We do it because we don’t know what we want to do. And it seems like the next easy thing to try to, like, we’re good at school, and so we continue on. We do it because, well that sounds kind of interesting. But we don’t really know much about it, or we think it’s all about litigation and end up in some other completely different practice.

And like you, I was always told I’d be a good lawyer because I was, like, good at arguing. Yet I did not become a litigator. And I never wanted to be a litigator like I thought I’d be a litigator. But once I figured out what that was really about, I realized it didn’t mesh with my personality.

So, FYI, people, just because you are good at arguing with people does not mean you are meant or destined to be a litigator. I was also a business lawyer and loved that aspect of the practice.

But I love that. Two things:

• You were very strategic, and
• Just because you choose to look into it for a reason that may not be considered a good reason, does not mean it’s the wrong path.

The key is to be strategic about the why and to get curious and to research and to figure out, okay, well, what? Because there’s a lot of ways to practice law, and there’s a lot of different skills and strengths that go into the different practice areas. So just because you got into it for an odd reason does not mean it’s the wrong place. But be strategic to find your place.

Why You Don’t Need To Know What You’ll Do As A Lawyer Going In (It Might Even Be Preferable to Knowing)

[00:08:08] Scott Oliver: Yeah. And you’ll find that a lot with law students, too, who say, I don’t really know what I want to do yet. And my answer to them, I teach at a local law school, is usually, that’s okay, you can go into law school not knowing what you want to do. In fact, that’s almost preferred.

I say go into law school for the right reasons. Figuring out, hey, this is something I’m good at, I would enjoy this. I would excel at it. All of the things that, you know, build for a good profession.

But then when you’re in law school, figure out, hey, do I want to be a litigator? Maybe not. Do I want to be a corporate lawyer? Maybe not. Is law firm life even for me? Maybe not.

There are so many different stepping stones, and so long as you’re willing to put your foot on there and say, hey, I can go left, I can go right, I can go forward, I can go backwards, all of these different things, you’re going to be successful.

And my path has really been kind of similar to yours. Going into law school saying, I’m going to be a litigator because I like to speak. I love being in front of a crowd. I like to talk. Obviously, I’m talking to you right now on a podcast, but I tried litigation for a summer, and I said, interesting. All right, not for me.

And very quickly learned, hey, there’s this niche out there, SBA lending, which we’re not going to get too much into, but there’s a niche out there where communication is critical. It also involves business. It also involves customer service. It involves all of these other soft skills combined with law. They kind of mesh together to make it the perfect fit for somebody like me, which would be a terrible fit of. For somebody else who might absolutely despise being a corporate attorney.

[00:09:44] Heather: Yeah. I’m curious. What made litigation not for you?

[00:09:49] Scott Oliver: I think it was more the adversarial nature of litigation. Some people love that, and I get it. It’s fun, and it’s the idea of what a lawyer does on tv and everything, but to me, it was a little bit exhausting. It didn’t, quote unquote, fill my cup, so to speak.

I really like deal work because you are working with a team, sometimes a couple people, sometimes dozens, sometimes ten plus. Right. But you’re always working to achieve an outcome. And while there might be some disagreements throughout the process, you’re all working towards the same direction. And once you get there, you know, hats come off, everybody’s happy, hey, we did it. Shake your hand. That sort of thing really appeals to me.

[00:10:38] Heather: You and I are so, like, same thing. I looked at litigation thinking, oh, this is where I meant to be. And I very quickly realized, oh, my God, this is not a fit for my personality at all and not a fit for my values.

So connection is a big value of mine. And not to say you can’t connect with people as a litigator, but your role isn’t to be collaborative. You know, the connection for me is partly about collaborating with others and working towards a common goal. And so that’s not what litigation is at all.

[00:11:10] Scott Oliver: And you can certainly be collegial and even friends with opposing counsel and litigation. But to me, deal work – similar to LinkedIn and some of these things that we’re going to get into – every single deal that I close with my colleagues here, it’s like that other attorney on the other side. I’ve learned something from him or her, or we’re able to build on that. I can refer things to that attorney, and we can talk down the road, and we’re just constantly building to be better, not only for ourselves in our practice, but to be better for the clients that we’re serving. And that type of mentality, to me, is just very attractive, and it allows you to come to work and say, these people that say the profession is toxic. Yeah, there might be some toxicity, but where I’m sitting, it’s blue skies. It looks great.

Is the Profession Toxic?

[00:11:53] Heather: Well, and it doesn’t have to be toxic. That’s a choice, honestly. And this kind of brings me into this whole differentiation between cultures of firms. And I would say this.

Some law firm cultures are very toxic, many are not. However, they may be for you, the individual person, because they may not be the right fit. And I think there is this disconnect.

But a lot of lawyers, because we are rule followers, we have this, like, path that we think we want to go upon, that we, we determine very early in our career. And unfortunately, that changes over time, right? Like, we change our ideals, change what we want changes. But for whatever reason, we like to keep this rigid path in mind that we determined when we went into law school or when we first started practicing.

And we can often end up in a culture that’s not a great fit for us, but because it’s supposed to be a great firm, but because everybody thinks we’re successful, but because of all this other stuff, we stick with it. That’s toxic for us because it’s not the right fit. Maybe it’s not the right fit practice. Maybe it’s not the right fit firm.

The Many Options As A Lawyer

[00:13:05] Scott Oliver: Yeah, 100%. And law students, I hope that it’s getting clearer for them that there are so many avenues that one path is not the right path for everybody. Because you see a lot of people who will talk about big law, for example, and be saying, big law is toxic, or big law is great, or big law is the only way. And the answer is so much more than just surface level there.

The answer, from my perspective, is all of the above. It is great for some people. It is toxic for some people, and it depends greatly on the firm and the person. So, law students, I encourage them all the time.

Check it out. Talk to the people who are at big firms. Talk to the people who have started their own firms. Talk to coaches, talk to people in legal tech, people in midsize law firms like mine, talk to these different people and say, what makes this firm tick and figure out:

• Does that fit with the lifestyle that you want?
• Does it fit with your financial goals, your practice goals, all of the different things.

Because depending on your practice area, your lifestyle, etcetera, one of those might be an absolutely terrible fit and the other might be great. And the answer is not always going to be one size fits all.

[00:14:20] Heather: Yeah. And you get at something really important here that I think we need to dive into a little more.

What does success really mean?

What does success mean to you, the individual? We tend to go in to our careers thinking that success means very specific things that are, frankly, very ego driven, based on external perceptions. A couple of things that are wrong with that.

We assume – that external perception – is that big law is the end all, be all, when I don’t even know what the percentage is. But a very small percentage of attorneys actually practice in big law. So the vast majority of attorneys out there don’t think success is big law.

But we in law school, because of the way that the on campus interviews happen, because, you know, all of that, we. We’re given this really false perception of what lawyering is and what law firm life is, and it’s not all big law.

And we also think in very rigid terms of, you know, what’s the money and what’s the, you know, how do others see me and perceive me based on what I’m practicing and what I’m doing and how it looks to others as opposed to going inward and thinking about, okay, what’s important to me here and how do I want to live my life? How do I want work to integrate with my life?

Speak to me a little bit about, because it seems to me you’ve done that work, you’ve thought about that, and you’ve been very strategic about how you have guided your own career based on what you value and what’s important to you and how you’ve chosen to define success for yourself.

Success Is Individual

[00:16:01] Scott Oliver: Yeah, that’s a fantastic way to ask the question. Right. So. So what is success? Is one of those questions we could debate about for hours upon hours and never have a true answer. Right. And what success means to me is going to be different from what it means to you and what it means to your listeners.

But what I encourage people to do is think about that exact question. What does it mean to me if it is purely ego driven and purely financial driven? First off, I think that’s a bad idea. But if that is, maybe there is a right path for you where it’s the highest salary, it’s the highest level of prestige, it’s all of these things. But you’re going to quickly find out that that’s not everything.

So going into it personally, I was saying, okay, I have these different firms here. Are these different opportunities? What are the people saying? What does the practice look like now, five years, ten years, 20 years down the road? Is there an opportunity to grow that? Is the firm supportive of my goals? Is the firm supportive of my family? Is the firm supportive of entrepreneurship within a law firm structure?

Because some firms will look at that and they will say, if you’re a first year associate, you come in, you’re going to get this nice, healthy check check every single two weeks, right? It’s not a check anymore. It’s just direct deposit. But you’re going to get this big salary, but you’re going to come in and you’re going to be a cog in a machine, and you’re going to site check, you’re going to do discovery, you’re going to do this, and you’re going to do that for ten years. Okay, great. You’ve checked the box on your financial goals. You’ve checked the box with XYZ firm. You look good to the outside, but inside you’re just working 12 hours a day, not really gaining any skills, and not really having the flexibility and mobility to figure out what works for you, what you’re interested in to build your practice, and you’re kind of neglecting your family and your hobbies.

[00:17:49] Heather: Yep.

[00:17:49] Scott Oliver: To me, that wasn’t interesting to me. I’ve been at the same firm ever since OCI – on campus interviewing. I did a summer associate position. I went from associate to partner, and I’ve been here ever since.

But the reason for choosing the firm in the first place was, hey, this is a firm where there are good people, where it is big enough that they’re getting the sophisticated clients, the sophisticated work, but they’re also small enough that they’re allowing their attorneys to be entrepreneurs within the firm.

Look Forward To Future Years (& What You Want Out of Life)

So to me, the success of choosing that firm was I’m choosing this not only for, obviously, the financial incentives, but also what is my life going to look like my first five years of practice, when I’m a young, married person getting ready to have a kid, all of that.

But also, what is the upside in the future? Is this something that I can take and really own my own practice and own and grow a group of like minded people who also have the same types of values, that is much more difficult to do in smaller firms. It’s much more difficult to do in larger firms, too. So to me, again, personal opinion, mid sized firms is that sweet spot where you get some of these quote unquote, success attributes that you might not get in other places?

How To Determine Which Firms Are A Good Fit – Ask Questions

[00:19:04] Heather: Yeah, I think there’s a couple of things there. I will say that not all big law is what we think of as the cog in the machine. There’s a fair number of of that, though, within big law. And you have to go in with your eyes wide open, really pay attention to not just how are people treated, but what is it they’re doing.

So when you’re coming in and you’re interviewing and you’re hopefully getting some type of a summer internship, you need to pay attention not just to the projects that you’re getting, but pay attention to those within the first three to five years of their career. What are they getting to do? What are they being asked to do? Ask a lot of questions.

Start asking questions, too. Very early of the more senior associates who are getting closer to being considered for partnership, what are they doing? What have they done? What is their day like? You, I think not enough young attorneys and law students especially, are good at this. They don’t think they can ask.

You can ask those questions, number one. Number two, if it is regarded as an annoyance, that’s a red flag. It is, in my personal opinion, like a huge red flag. Stay away from that firm long term, most people will see that as a positive because they’re going to see something in you that they don’t see from a lot of people.

Pay Attention to The Partners – Their Lives (& Be Honest About Whether You Want That)

So ask those questions, then also pay attention to the partners. What did their lives look like? Do you want that life? Right.

So I remember early in my legal career, I started with, I would call it big law light. It was a big Texas firm who very much practiced like a big law. The Texas firms back then had the Texas market locked up, and they were the places to go in Texas for that, were considered the preeminent places. It’s totally changed now, but because a lot of the big law firms have finally gotten into Texas and really gotten pretty good practices here. But back then, that was the place.

And I remember my first couple of years paying attention to, especially those more senior associates and then the partners, and there were some partners there. I’m like, I do not want that life. Like, there’s just no way there were some partners who I actually like.

The other thing that is interesting is there are subcultures within group, within firms, especially the big firms. Different offices have different cultures and different practice groups have different cultures. So I kind of steered clear of the people in the groups that I really didn’t want that life and kind of, like, reoriented myself towards the ones that I really enjoyed working with more and thought, okay, I may not want that life or practice fully, but there are aspects I can learn from them. And ultimately, I chose to leave and go somewhere else.

But you bring a really good point to start paying attention to those things because it does matter. And you have ownership of your career. Nobody else is going to do this for you.

[00:21:59] Scott Oliver: And I think students sometimes don’t see that. Maybe they don’t think the short term of their ability to make it a two way street when they’re interviewing but also not saying, all right, I’m not taking this job short term because I want a paycheck and I just want to learn a little bit, and then I’m going to jump ship. I always encourage students to say, do exactly what Heather is saying here.

Practicing Law Is A Long-Term Game

Talk to the people who are five years in, ten years in, 20 years in, and say, is this a path that I can see myself in long term? Because a lot of the practice of law is a long game. It’s not a short term play where you’re just going to job hop until your next opportunity because you got a couple thousand dollar pay raise.

It needs to be a place where you say, here is my career, here are all of the support systems around me that are going to allow me to flourish and have that quote, unquote, success in all of the ways that success is intended to be. And that could be at any size firm.

And I use the cog in the machine as kind of the stereotype of big law. There are plenty of big law firms where you can go and have the most amazing experience with some of the best partners and associates in the business in their specific industries. But it will use the fun thing, right? It depends.

It always depends on the people that you’re looking at. And you can’t just be seeking the ego pieces that you discussed. You need to be seeking that long term support, that long term vision of what it’s going to look like for you. Two years, five years, ten years plus down the road.

[00:23:33] Heather: And I’ll say this in my personal experience, practicing for over 18 years and now as a coach, I don’t think I’ve met an attorney who has gone into it saying, “I’m just going to gut it out for three to five years, make as much money and then get out”, who’s actually ended up doing that.

The way they thought it would work out, it doesn’t work that way. You get sucked into it. Those are typically the attorneys who, 10 and 15 years later are incredibly unhappy.

They leave the law completely, which is kind of sad after everything they’ve put in, or they don’t, but they’re just miserable for the rest of their working lives, and that’s not worth it.

And all because they wanted the big paycheck at the beginning. It’s so true that it is a long game. Any career is. Especially a professional career like the law. You’re going into it for the long term. Set yourself up from the beginning in a place that you actually enjoy working, where you’re going to learn something where you can remain curious and satisfy that curiosity, because most lawyers go into it being curious people, and yet it gets beaten out of them over time, which is really sad.

[00:24:47] Scott Oliver: And I think we a lot of times follow the money, too. We’ve mentioned during this conversation already. And I think it’s important because law students have student loans and they see a paycheck as one of those egotistical things that they look at as a status symbol.

But some fail to realize that a paycheck for a first year associate or a paycheck for a fifth year associate is just one thing. If you’re at a place, no matter the size, from owning your own shop to being a coach to being in legal tech or whatever it is, the long game is what you’re playing.

Like I said before, and there are opportunities that are virtually endless if you’re surrounded by people who are rowing in the same direction, who are supporting you and allowing you to grow. So, hey, yes, you might at XYZ firm have a higher paycheck as a first couple year associate, but look, 20 years down the road and all those people, the playing field will even out for the right people. And it’s all about who you’re surrounding yourself with and the support that you’re getting along the way.

[00:25:47] Heather: Well, I will. I’m going to leave it with this one last thing, because this reminds me of when you start saving and investing, you hear from financial advisors that you don’t have to do a lot, but do a little bit. Like start early, start early, start early, because it really does make a difference. 20, 30 years down.

I kind of see picking the firm and kind of being strategic about your career in a very similar way. Because when you pick the right, maybe you’re making $50,000 less than another firm. Like, it can be that big of a difference, by the way, right. Your first couple of years, if it’s big law versus a non big law, it could be even more.

It could be a lot of things. But, you know, ten years down the road, that person who picked it just for the paycheck is probably not. They’re being, if they’re still at that big firm, they’re being downgraded, they’re not making partner, they’re not going to make the same money, and they’re kind of stuck. And it’s very hard to move at that point. And a lot of those people end up very unhappy and not making as much.

Whereas you, who took that lesser amount at the beginning, you got better cases or projects, you learned a lot more. Guess what? You get to make partner younger than you start to get, like, you know, 10 – 15 years down the road, you’re making a lot more money than that other person. And it, it’s paying big dividends and it’s, it’s cumulative over time.

So not to say like, you need to be able to pay off, pay your loans and make regular payments and have a reasonable lifestyle. But I think we get too, and this continues into our senior years too. I know a lot of more senior attorneys that jump ship for the money from one firm to another, and they end up really regretting it.

And, you know, it’s not just about the money. The money is nice and all, but you can make good money just about anywhere as long as you do the right things, develop yourself appropriately, learn and enjoy yourself.

How To Figure Out What Fills Your Cup

You said something that I wanted to ask a little bit more about. You said, you know, you wanted to find a practice that filled your cup. Do you have any advice on how people, whether they’re, I mean, granted, early on would be the best time, but what if somebody’s even a five or eight year attorney and they realize, I’m not doing what I want, I have to figure out something else.

There’s lots of other things I could pivot into. How do you figure out what fills your cup?

[00:28:18] Scott Oliver: Yeah, I think it’s a mix, and there are diagrams out there, and I can’t repeat exactly what they say. I can’t remember. But it has to do with, you know, finding something that blends what you enjoy doing, what you’re good at, your areas of genius, what you’re naturally drawn and able to do, and then also the prospects of how you can build it or how you can continue it long term in the future.

So for me, the biggest piece of it was what we talked about earlier. It was rowing in the same direction with a bunch of like minded professionals, whether it’s in the firm, growing the firm, growing the department, or outside just working with good buy side counsel lenders and things like that.

So that piece fills my, I guess you would call it like my interpersonal cup, to be able to say, I like what I’m doing with you, building something to achieve a common goal. But people don’t normally enjoy things that they aren’t good at. That’s not to say that you can’t train when you’re a first year attorney.

You’re probably not good at a lot of things, but you can ask yourself, am I a good writer? Am I good at talking with people? Am I good at negotiating? Am I good at customer service? Like, what are these things that I’m good at? And if you find an area of law in something that you are good at, chances are you’re going to be able to strengthen those skills, you’ll be able to play to your own strengths, and you’re going to have a lot more fun doing that.

And then finally, last piece of that is, what does it look like down the road for me, picking a practice area. I picked it when I started saying, here is a very hyper niche practice area in areas that I find interesting, that I enjoy with people that I like working with, in topic areas that I think in the next couple of decades are going to either stay the same or explode and get even bigger.

So when I say explode and get bigger, what does it look like? Generational wealth transfer for SBA, small to medium sized business deals. But then also, how is tech going to impact it? So looking again, 510 years in the future, am I going to enjoy? Am I still going to be needed? And how does that look in the future? And to me, all those things came together and I said, well, this is, this is a real opportunity that’s not just ego driven. This is an opportunity that’s going to fit my schedule, my personality, and the way that I want to live.

[00:30:38] Heather: Okay. There’s so much in that. So I’m hearing you don’t use this language. This is coach speak, probably. But I’m hearing a, first off, understand your skills and strengths. Skills are the things you’re really good at.

All the things we know. I’m a good writer. Am I a good speaker? Strengths brings into what do you actually enjoy and really excel at? And then also other personality, why do people come to you?

So, for example, I’m the oldest of our family, and I’ve always been the one people come to for advice. And not just advice, but really when something seems like, so complicated or challenging that they can’t even, like, figure out the forest of the trees, they can’t figure out, like, where do I even get started? I was always the person that would, like, could sit down, listen to them for five or ten minutes, and in a minute or two go, oh, it’s XYZ or ABC or A and B, very quickly, just get rid of the rest. You’re overcomplicating this, right? So, that’s a strength.

And that helped me determine the practice that I wanted, because when it came to putting certain types of deals together and understanding businesses very quickly and understanding how to structure things that’s what I really loved doing, and I was really good at it.

So that’s, you described it, but I wanted to give some context of what does that mean? Right. So strengths and skills.

The other thing was values. Values are key, and that gets into the personality and cultural fit for you. And we’re not talking just the law firm, but the specific practice that you choose and the specific clients you choose to say yes and no to because you don’t have to take every client out there. This is something lawyers are really bad at. And so it’s very strategic.

It’s understanding you, your strengths, your skills, your personality traits, your values, and then strategically making very intentional decisions along the way.

Niching Your Practice

You also said something else that I wanted to highlight, and that’s niching. Lawyers are scared to death of niching. Many lawyers are.

Did that ever, was that ever a concern for you?

[00:32:50] Scott Oliver: It wasn’t. And that was surprising to people. So very early in practice, they said that, you know, I like deal work. I like mergers and acquisitions. I like finance. I like all of these different areas. And I quickly got into, you know, an existing practice that we have here, which was SBA lending. And I would have people here at the firm and other places come in and say, look, you’re going to pigeonhole yourself. Watch that. You know, if you’re a one trick pony, what happens if that dries up? You’re going to have a real issue.

I just kind of, I let it go, you know, one ear and out the other and said, I don’t think that’s true, because lawyers, one of our weaknesses is we try to be generalists sometimes, and we want to be a jack of all trades, and we’re all knowing. We’re super smart. You know, we know every answer that’s not true.

And every lawyer that I’ve met that’s hyper effective is somebody who is drilled down into a practice area, and that’s niching down. It’s not to say that you only know one thing, but to me, the SBA lending, again, we don’t want to get into the details of my practice, but SBA lending for banks is hyper niche. Very few people, very few firms are specialized in SBA lending.

So that niche allows you to be the go to person in the marketplace, the thought leader, content online and things like that, branding, all of thats really, really important. But then you realize that it looks like its pigeon holding on the outside. But then you realize youre running thousands of deals for these banks. You are not just doing SBA lending, youre learning mergers and acquisitions. Youre learning real estate, title insurance, quarterbacking deals, settlement statements, figures, all of these things that say that the SBA dried up tomorrow. Trust me, it’s not going to. I think it’s a very long term, lucrative type of practice. But if it dried up, it’s not like you just sit here and twiddle your thumbs and go out. And I’d be an M&A attorney.

[00:34:39] Heather: You could totally pivot easily.

[00:34:42] Scott Oliver: And people on the outside and don’t see that. They just have a very, I guess, short term look at what somebody is doing and saying, if that’s not there, you can’t do it. That’s not true. And you just have to take a broader view.

[00:34:58] Heather: Well, I find it interesting. Two things come from this that you’ve highlighted.

Niching Helps You Marketing More Effectively

Number one, niching actually helps you build more business much more quickly because you know exactly who you’re speaking to, who you’re targeting, how to speak to them. Like it’s, it’s so much easier when you niche in, and people don’t realize that. It sounds counterintuitive to a lot of people, but it, it is so true.

And it’s probably one of the biggest arguments. I get in with my, some of my clients, especially my litigators out there who say, I’m a generalist, I can litigate anything. It’s like, I get that. And yes, you can still take on anything you want, but we need to focus on something when it comes to our marketing or you’re speaking to nobody. Right. So there is that.

You Can Always Pivot (It Isn’t As Hard As You Believe)

The other thing is, you’re smart. You’ve gotten here, you can pivot like, it is not that hard.

And take it from somebody who pivoted several times. So I started as a energy lending lawyer because my first firm was primarily based in Texas, very energy based. Well, the energy lending market fell to nothing and we had to start pivoting.

And soon thereafter, I moved and I ended up in structured finance. And theres a little thing called the financial crisis that happened in 2008, which is right when I made partner as a structured finance lawyer. That really sucked, by the way, because I had a little book of business that I was super proud of. When I made a made partner, that was zero. Like, by the end of that year, I had to pivot again and decided to become an ABL – asset based lending – lawyer.

That, I’d never done that before, but it wasn’t that hard to figure out based on all the stuff I’d already done. Most everything I had done was really translatable into that anyway. And so I just had to change my language a little bit. And then I pivoted and rebuilt from scratch and built a very successful practice like you can.

And I’ve known lawyers who were real estate lawyers who became bankruptcy lawyers who were like, you can pivot. It’s not as hard as you think.

[00:37:02] Scott Oliver: True, but you hear that a lot from people about the pigeonhole, and you kind of just have to listen to it respectfully. I respectfully disagree. But let it kind of go in one ear and out the other, because if you understand what you’re learning, how it translates and, and how a pivot would look if you had to do it right, you may never have to do it.

But if you had to do it, I think it’s much easier to be okay with yourself and feel comfortable in your own skin as a practicing attorney, especially early on.

And I think the simplest way to look at niches to me is something people say all the time, which is if we were in the medical field and you and I were having this type of conversation and said, oh, I’m having a heart issue right now. Somebody called a doctor, I’m having a heart attack. Am I going to call a podiatrist? No, I am going to. I am going to call somebody who specializes in parts. I’m going to call a cardiologist.

Becoming Known for Something

The more you can focus and niche down, the more powerful you are to be able to do, quote, unquote, that thing that your client wants. And the easier you’re going to be able to quickly identify who is my audience, who are the clients that I want, and who can I service the best. And it turns out to be a net win for your practice, but also for your clients, because they’re getting tailored, focused, hyper focused work by somebody who knows the language, speaks the language, and does these deals inside and out every single day.

[00:38:20] Heather: Well, and you highlighted the perfect thing. You become known for that thing. And when somebody needs that thing, that means you are the first person they think of and they reach out to. And so that thing doesn’t have to be needed by everyone.

You just need to be known for that thing, so that when the people who need it, they think of you. You don’t need a million clients.

This is why niching works so well.

How Scott Got Started On LinkedIn (That’s Genius & You Can Do, Too)

So I want to pivot a little bit. We were talking about pivoting and get into LinkedIn because you are a pretty prolific poster on LinkedIn.

What made you get started?

[00:38:57] Scott Oliver: Well, it’s a really good pivot. I think it’s funny, you use pivot, right? Because it started with niching. Right. So niching down. I started really being active on LinkedIn around 2015, and it was because I found SBA lending, and I’ve been working in corporate level M&A type work, but I found SBA lending, and I said, wow, this is really dense.

There’s this book, I’d get it out for you if we were on video, right? And there’s this book of hundreds of pages of regulatory language that governed a lending transactions under the SBA programs. Okay. And it was overwhelming to me. So I quickly dove into that book and started translating the complicated stuff to very simplistic language that me, not even an attorney yet would understand.

I said, okay, here’s this rule. What does that actually mean? And I wrote it in plain language. And back then on LinkedIn, not so much anymore. Articles were really popular. So I started writing articles, some of which are probably still on there and out of date by now. But I would write these really, really short, easy to read articles about a topic that I was teaching myself.

So I was teaching myself SBA lending, and I said, well, LinkedIn is the perfect place to meet other professionals who are also just teaching themselves. So I went on there, and I connected with a bunch of people who were just getting started out in the SBA world or in the banking world. And I sent them my article.

And I kind of had this canned thing where I said, hey, my name’s Scott Oliver. I’m going to be an attorney. I’m interested in SBA lending. Here is what I found. Here is what this means. Would you like to follow and grow along with me?

[00:40:40] Heather: Wow.

[00:40:41] Scott Oliver: Sent it to probably hundreds, hundreds of first years at banks and said, look, learn with me. I’ll help you. This isn’t legal advice, but let’s go.

Since that time, periodically, over the next year or so, when articles were big, I would write about these topics and send it to all of these people and say, hey, just checking in. I learned this new thing today. Look at this. This is how you write it. This is how you understand. And they say, oh, great. Well, that’s really fun.

And we keep doing it over and over again. And now those people who I was communicating with when they were just starting out are now owners of banks. They’re now leading divisions. They’re now doing things that aren’t even related in banking. And we’re all still very, very close.

But it all started with those articles taking something complex, making it simple, and then just paying it forward and just sending it to people to help others.

[00:41:27] Heather: It highlights so many things that I try to get across to my clients that I just want to, like, make note of before you move on.

It’s Never Too Early To Start (or Too Late)

Number one, it is never too early to get started. It does not matter how much expertise you have. You can talk about something even as you’re learning it.

It is amazing to me how many young partners come to me saying, well, I can’t really write about much on LinkedIn yet because I’m not really an expert. I’m like, you’re a partner. You’ve been like, there’s plenty of stuff you can write about with knowledge and expertise.

And even as you are learning, like, share this information for others, there are people out there who will be interested in it, who will read it, who will want to hear about it. And this highlights that so perfectly because you did it before you were even officially an attorney.

[00:42:13] Scott Oliver: Yeah. And that was the learning process for me. So I wasn’t posting like you post now. It’s, LinkedIn’s developed over time, but over time, it went from articles to just posting. But by the time you’re posting, I then at the time, had a couple thousand followers who were all in the banking industry. So all of a sudden, they were seeing my name over and over again about things that I’m doing, about different topics, about the SBA, about different programs, about my journey over and over again. So when they would see my name, they’d automatically think of it as SBA. Oh, the corporate lawyer, the M&A guy, Lewis Kappes, all of these different things.

And it worked out really well.

Posting About More Than Work (On LinkedIn)

But it wasn’t until probably around a little bit before the pandemic, but around the pandemic, when more people got online and things like that, I actually stopped posting more substance, you know, the quote unquote boring stuff to most people.

And I started posting about, you know, my life, my journey to practice, my journey in law school, my journey to being an associate, eventually partner, family life, all of these other types of things. And initially kind of got the pushback of, this isn’t Facebook. Why are you posting this?

Naturally, I said, I’m not going to listen to you, and I’m going to continue posting this.

And it exploded from there, and it got a lot of traction, not just from clients, although I think there’s some unintended business development when you post those types of things with clients, but from attorneys or young law students who would reach out and say, oh, I’m glad somebody is saying this, and you also are on there doing these types of things where you’re saying the things that nobody else is talking about and showing people that being an attorney isn’t just writing about the SBA Sop, although that’s great.

And I do that sometimes just to keep the branding on point. Right.

But being an attorney is being a father. Being an attorney is also being a friend. It’s being a mentor, it’s being a mentee. It’s being all of these different things that make a person interesting and authentic.

Because I’m going to say it, I might get some hate for this, but there are a thousand other people who can do what I can do. From a legal standpoint, we’re all qualified, right? You are a lending attorney. You and I could do the exact same things, but you bring to the table something that I don’t and I bring to the stable something that you don’t.

And the more that your clients and other people can see that, the more attractive it is going to be to be able to work with you, the better the relationship you’re going to have working with them. Which makes it an overall, overall better attorney client experience, which in turn makes it an overall better experience for your clients customers.

And in my business, it’s all customer service because I’m working with banks, but I’m also working with attorneys. I’m working with the bank’s customer, the borrowers, I’m working with third party title companies and things like that. So the more we all know each other and know how we operate, the more we know even our families that the more of a pleasant experience it is. And it results in getting deals done.

What Is Branding & Why Is It Important As A Lawyer?

[00:45:15] Heather: I mean, you’re highlighting something so important here that comes. When it comes to branding, okay, because we’re talking about branding to some extent, I think people misunderstand what branding is.

Branding is not creating an image of your, you know, what you want out there. It’s actually just showing up as you, as best you can as a human being. So that you can, you use the word authentically, but naturally, authentically, organically, kind of just be who you are and attract the right people to you and repel the wrong people.

You don’t want to have every person as your client. You want the right fit.

And it’s also about being a human being. Because we’re not just lawyers, we’re people who are spouses and parents, and we have hobbies and we have interests. And I think lawyers, part of the problem that we have in this profession is we get too stodgy. We don’t want to show be human for whatever reason.

Like, we’re convinced that that’s somehow unprofessional. But there is a difference in being a human being and sharing too much, right? We’re not talking about TMI sharing, we’re talking about showing up really as you, as a human being, and sharing the things that show people who you really are and how you relate to others, including your clients and opposing counsel and borrowers.

And that gives a much better representation of who you are and how you show up in your day to day than anything else can. That’s, to me, what branding really is about 100%.

[00:46:49] Scott Oliver: And you really honed in on something important, which is the authentic side. Because since that time, 2015, everybody laughed at LinkedIn. Not very many people were on there.

Lawyers started getting on there. Now it’s a lot more popular, and there are people who are content producers, influencers and things like that on there. And I have differing takes on those types of people because some people are community builders, they are influencers, and their job is to get eyeballs right.

Don’t Worry About Or Try For Likes (What To Do Instead)

But for me, and what I think the approach is for most lawyers, law students, etcetera, is do not try to get the likes everybody likes likes, right? But don’t try to just go about your day, have experiences and pull from those experiences and say, hey, you know, this could help somebody.

And some of the most, I guess I wouldn’t call it more memorable posts that I have, haven’t been the ones that go viral and have thousands of likes. It’s not the ones that are about the SBA or anything like that. I’ll post something random and just say, hey, this was on my mind. Doesn’t really get any traction at all. No comments.

But guess what? There is a direct message. And that direct message might be from a student who says, I was struggling. I didn’t think anybody else felt this way or I had this problem, let’s talk a little bit more and then you’ll get gratitude along the way of, hey, that really helped me out.

That really helped me personally, professionally, whatever it might be. And none of that really shows up on the homepage or on what you’re doing. But people read and not many people are posting. So if you have a microphone and you’re able to do it positively, ethically.

[00:48:31] Heather: Professionally, yep, as they do it, I so wholeheartedly agree. And a final note on likes and engagement. Something I have definitively learned is there is a subset of people out there who like and engage like crazy. Those are the people who are pretty active on LinkedIn in all honesty.

And they’re liking and engaging partly so that people will notice them, so that people will go read their stuff, too.

So when you’re first getting started, you’re not going to get as much of that, right. It. It takes time to build, but people do notice. And people, as long as you’re coming from a place of service, that’s what I hear from you, is serve. Like do something just to put it out there to help somebody.

I always go out there with, if this just helps one or two people, it’s a win, right? I don’t care if 100 people, 1000 people, or just one person get something out of this, as long as somebody does. And so that’s always the mindset I go into it. What I have found also is I get messages, emails, and then I’ll get calls from people or a new client, you know, a new client who’s like, oh, my God, this post a month ago resonated with me so much, and it’s one that hardly got any engagement, right. So there are people reading it who don’t comment, don’t engage, but they’re remembering it. It is making an impact, even if you don’t see it in the impressions numbers and the engagement numbers and all of that.

[00:49:57] Scott Oliver: And LinkedIn is a very, it has a lot of staying power. LinkedIn, unlike other platforms, it is there almost as an existing resume and a biography of who you are as an attorney and a person, where people will look at it like you said, and they don’t necessarily engage, but they then know you, whereas other platforms, we won’t get into this.

I know you don’t have time, but like X or Twitter, right? I still call it Twitter. Um, Twitter is very, very quick. Once you do it, five minutes later, it’s gone. But that platform is much more. You could have millions of views pretty easily on something that’s just silly and not professional LinkedIn.

You could land a six, seven figure plus client with a silly little thing that nobody really engaged with except one person, and that one person made all the difference, or you change that person’s life and it’s a student, you know, all of these different, you know, buckets and categories that you could fall in. And it’s. It’s quite an amazing thing, really.

[00:50:51] Heather: It really is. So, moral of the story. If you’ve been thinking about LinkedIn, get out there, start using it. It really can be powerful, and there are so many ways that you can utilize it, make it your own.

And final note on this whole, like, LinkedIn thing, because you. I think you this comes across in your story, but I want to highlight this.

It is not too early to get started. Like, you can get started really young when it comes to business development. And one of the easiest ways is through relationship building like you did and also through your marketing efforts.

Becoming known as that person can be very simply done just by showing up and being consistent and talking about kind of the similar things. Um, you don’t want to be all over the place, but talking about the things that are important to you, whether it’s within your practice or whether it’s within, you know, lawyer well being or something else.

And you said something early on. It’s not just the SBA posts that got you clients, but you think some of this other stuff gets you clients as well. I would agree. Because people notice the more personal posts and then they think they. They feel like they know you and they want to work with you. So they know you for as that guy.

But there’s more to it. They know you as a more whole person who they actually want to work with. So when that thing comes up, then that you’re really the person they want to reach out to. So it is. Time is pretty much up. Is there any final thoughts or a final thought that you would like to leave people with before we let you go today?

[00:52:26] Scott Oliver: That’s a. See, that’s a deep, million dollar question.

I’ll leave it with.

I relate to you and what you’re doing so much and the things that you say here. And I think it’s so great that you’re getting these types messages out to people, because one of the most critical things that I’ve noticed in the last ten or so years is the power of podcasts, social media, and all of these other forms of technology that weren’t here 20 plus years ago. So you have a microphone, just like I have a microphone online. And you can use that for good or you can use it for bad. And I love to see that you’re using it for good, but your audience can do the same thing, whether that is business development, just personal relationships, mentor mentees, etcetera. You can have a microphone and completely transform your practice or transform the life, whatever that life is that you want to live.

[00:53:20] Heather: Absolutely. How can people connect with yo should they want to?

[00:53:24] Scott Oliver: Well, connect is the easiest one, right? Find me on LinkedIn. It’s Scott Oliver. You can find me on there. Otherwise, my email address. I will respond and I’m happy to help in any way.

[00:53:45] Heather: And I will be sure to include a link to your LinkedIn profile so that people can connect with you there in the show notes. Thank you so much for being here today. This was an awesome conversation.

[00:53:56] Scott Oliver: Thank you for having me. I appreciate it.