In this episode of “The Geek in Review” podcast, co-hosts Greg Lambert and Marlene Gebauer interview Ryan McClead and Kate Boyd, the CEO and COO of Sente Advisors, respectively, as part of their “Love and Legal Tech” series. The interview delves into the couple’s history in the legal technology space, their experience working together, and the challenges and benefits of being in a relationship while also being colleagues.

Ryan and Kate share their extensive backgrounds in legal technology, with Ryan starting in the industry in 2003 and eventually becoming the head of innovation at a law firm, while Kate began her career as an intern at a law firm and later transitioned to the vendor side, working for companies such as HighQ, Compliance HR, and Kira Systems. The couple met while working together at HighQ and became good friends before starting their own companies in 2018 and eventually dating.

When discussing the best aspects of working together, Kate mentions the empathy and understanding they have for each other’s work habits and the ability to help one another when stuck on a problem. Ryan adds that working together eliminates the need to “download” their workdays to each other every night, as they are already aware of what the other is dealing with. However, they also acknowledge the challenge of not letting work consume their entire lives and the importance of setting aside time for non-work activities.

The couple shares their experiences with reactions from others when they reveal that they work together, ranging from surprise to curiosity. They also discuss how they handle disagreements within their company, emphasizing the value of their different perspectives and the trust they have built in each other’s problem-solving abilities.

When asked about the interesting projects they are currently working on, Ryan and Kate highlight their involvement in AI-related projects, product launches, and technology evaluations for clients. They also offer advice for couples considering working together, stressing the importance of maintaining separate work and personal personas, knowing each other’s strengths, and nurturing professional friendships outside of their shared work life.

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Music: ⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠ and Eve Searls


Marlene Gebauer 0:04
Welcome to The Geek in Review the podcast focused on innovative and creative ideas in the legal profession. I’m Marlene Gebauer.

Greg Lambert 0:11
And I’m Greg Lambert to Marlene for those that are watching on video. Do you notice anything different today? Yes.

Marlene Gebauer 0:17
Yes, I see. It’s all gone. It’s all gone. It’s

Greg Lambert 0:24
so occasionally, once a year or twice a year i i start all over,

Marlene Gebauer 0:29
he does a reboot. Yeah.

Greg Lambert 0:32
He does a beard reboot. And I’ve got my camera pointed the other direction. So you can see my She-Hulk poster poster. And you can hear pod dog. So, for our love and legal tech feature this week, we have with us some, some old friends of ours, Ryan McClead, the co founder and CEO, pretty old. It’s gonna show five now, Ryan. So Ryan McClead Is the co founder and CEO of Sente Advisors, and Kate Boyd is the CEO of Cynthia advisors. Ryan, Kate, welcome to The Geek in Review.

Kate Boyd 1:15
Thank you. We’re happy to be here.

Marlene Gebauer 1:18
So I know Ryan’s been on a few times. And Kate has actually talked to us as well. So they kind of know how this this works. Although this one’s a little different, because we’re sort of delving into sort of relationships and work and relationships. So you guys have a really sort of deep history, both of you in sort of the legal tech area. And you know, we’re using tech, legal tech kind of loosely, to cover a lot of the sort of the related professions as well. Tell us a little bit about, you know, what you have done and what you’re you’re doing now. I’ll start with Ryan.

Ryan McClead 1:55
So I started in legal tech 2003, I started answering the Help Desk at a law firm and did that for several years moving up through IT, eventually moving into knowledge management. When I was asked, What do you know about knowledge management? I said, What’s that? You’re gonna be great at this. Suddenly, I was the head of knowledge management.

That’s what everybody says. Yeah, exactly.

Still say. So I did Knowledge Management. Then I when we combined with a larger firm, I was the head of innovation globally, around innovation. The firm for several years. Now went to

Greg Lambert 2:37
that was pretty early to right Ryan. I mean,

Ryan McClead 2:40
I was one of the first people I knew with innovation in my title. That was 2013 Probably no yeah. 2013.

Greg Lambert 2:48
They give those things out like candy now right, Marlene?

Marlene Gebauer 2:55
So deserving Greg deserve anything.

Ryan McClead 2:58
I went to the vendor side, joined HighQ, which is where I met Kate and then was at Neota Logic for a few years and then five years ago, we started Sente. My partner Shashi and I started setting cake came along a few years after that,

Marlene Gebauer 3:13
She needed some convincing, okay, so So Kate, like, tell us tell us your origin story.

Kate Boyd 3:18
So I started working at a law firm as an intern. When I was in college, I was actually doing the press clippings by hand for Sherman and Sterling.

Marlene Gebauer 3:27
Ah, yeah.

Kate Boyd 3:30
And that segwayed as I was graduating from college, I talked them into hiring me to build one of their first websites. Back when lawyers were trying to figure out whether or not they actually needed a website. And they were pretty convinced they didn’t. But I was pretty convinced I needed a job and some insurance. So I talked them into hiring me. So I worked at Sherman and Sterling and then White and Case always focused on kind of digital marketing, marketing technology, CRM systems can have that side of the world, and kind of married that across to matter management and intranet. So working closely with the KM and IT teams at firms. And that’s what led me eventually, to shift to the vendor side. I had gone back to get my MBA and realized that I needed to take that role at law firms and blow it up a little bit. So I went, I was at HighQ for a time I was at Compliance HR now and and I was at Kira Systems. Before in 2018, I co founded a litigation finance company. And that was doing that. When Ryan and I started talking about what was going on at Sente. And at that point, we’d survived COVID. So we figured, hey, let’s give it a shot and see if we can work together. We’ve spent so much time together now.

Greg Lambert 4:49
Well, Ryan kind of teased about two of you meeting So Kate, do you mind just kind of elaborating a little bit more how, how’d you find yourself working together?

Kate Boyd 4:58
So I had been at HighQ like coming up on a year. And Ryan was a well known thought leader, obviously in the legal space.

Greg Lambert 5:09
Because he writes extensively on three geeks.

Kate Boyd 5:15
So I was glad I had to spend an entire week kind of marketing planning session where Ryan McClead to name was in the top corner as if he joins HighQ, so much is going to be able to happen. And then when he accepted, we had the joy of kind of building up a team here in the US focused on kind of talking to clients about how they could use that technology.

Marlene Gebauer 5:38
You guys had been working together before you guys started dating, right? So how, like, how did that occur? And how was that? I’m trying to be so careful. I’m looking at Ryan.

Greg Lambert 5:54
And was there an Irish Pub involved?

Ryan McClead 5:56
There’s always an Irish pub involved. Yeah, no, we had we worked together at HighQ, we became very good friends. We left HighQ about the same time, I joined Neotia Logic, Kate join Compliance HR, which was a sister company of Neota. And then she was only there a short time and went to Kira, and was, was a Kira for a while. So we had about a year and a half, I think that we worked together. But we become good friends at that point. You know, we then in 2018, we were both starting our own companies, that that’s always a great time to start dating.

Marlene Gebauer 6:37
No stress, nothing,

Ryan McClead 6:38
No stress, you know, to people starting companies that What could possibly go wrong. And we started dating late 2018, about the same time we started companies. And Kate says, I’m going to get a dog. And I said, That’s a terrible idea. Why would you do that? Well, the kids want a dog. All right. So we went out, we got a dog together. I helped her pick up the dog. And then what what happened was, she had to go to an office, I was working from home, we were living separately. And I ended up babysitting the dog all the time. So my mom found out I was dating Kate, because she heard the dog in the background. And said, what was that a dog?

Greg Lambert 7:25
she was talking about you?

Ryan McClead 7:28
So yeah, so we kind of did everything backwards. We had a dog together, about the same time we started dating, and then a pandemic happened. And that that sort of changed things a bit. You want to add anything to that Kate?

Kate Boyd 7:47
I think that pretty much covers it. Our first date was a baseball game.

Ryan McClead 7:54
Oh, yes. We did go to a baseball game. That was our first date.

Marlene Gebauer 7:59
Yes, official date. Nice. Yes.

Did they win?

Kate Boyd 8:02
I don’t remember.

Greg Lambert 8:06
If it was a playoff game than No,

Ryan McClead 8:08
Yeah, no, it was definitely. It was late in the season.

Marlene Gebauer 8:13
You know, you’ve mentioned that, you know, you were both starting new companies. So that was sort of when you were working separately, and now you actually work together in the same company? What have you found, like, the best thing about that is sort of, you know, working in, you know, either sort of related professions or actually in the same company,

Ryan McClead 8:32
I’m gonna let you answer this one.

Kate Boyd 8:33
I’ll answer this one. So I can, I’ll jump in, I’ll jump in and let Ryan stepped in after the thing, though, the way we work and the intensity with which both of us work. I mean, we often spend a lot of time both during the day, and then after thinking about and developing ideas and working on things. So it’s nice. Because we work so closely together, we both know where the ebbs and flows are. And so there’s a lot of empathy for, you know, what are you doing? Can I help you with it, or I know, you just need the next two days to kind of be in a bubble. And we can kind of protect each other to be able to do work at the level that we want to do it. We also can help bring new ideas and ways of looking at things when one of us gets stuck with something. So I think that that makes it work really well. Ryan, what would you add?

Ryan McClead 9:29
Well, I think when we were working separately, we we essentially downloaded every night anyway, it was You won’t believe what I dealt with all day. Right? So we were already living each other’s days, reliving them every night and there’s something about not having to do that. Right. I know what you went through today. I know what you were dealing with today. We were working on it together. That’s it’s it’s kind of nice if you’re in that position and You work well together. It’s, it’s nice to have that the sense of we’re we’re in this together. And I know what you’re, I know what you’re doing. And I, you know, the downside is it’s very easy to work all the time. Especially if you’re you know, workaholics who enjoy what you do. It means we have to occasionally say, Okay, we’re not working, Hey, kids, we’re not working for the next few hours, let’s go do something else. And variably we talk about work. But in some ways, I think it’s actually easier to be working together in a high powered jobs than it is to be working separately in high powered jobs. So she may disagree,

Greg Lambert 10:47
I was going to ask Kate, tell, tell us a little bit about some of the challenges that you faces as a couple that works together. I know, you probably have different offices within the house. But I mean, you’re always within 20 feet of each other, right?

Kate Boyd 11:03
We actually have our office, I’m in the office, and his desk is right there. So we actually very often,

Greg Lambert 11:11
they’re really closer, so you can reach over and slap him on the back of the head when he says something.

Marlene Gebauer 11:15
Like, no.

Kate Boyd 11:16
So there are times when we don’t entirely agree. And this isn’t just between us, I think this is everyone. At Sente, there are times when we don’t we don’t walk into a problem from the same approach. And so they’re often is at a time and a process of like, okay, I understand, that’s why you’re doing that. But why, you know, Can you can you approach that differently? And what about have you thought about these other things? So I think just, I think we both are, and, again, everyone in the company, we’re fairly careful to make sure that those kind of challenges that are so healthy and so important to, to being good at what we do, that we couch them from a productive standpoint, that’s something that occasionally and probably I am the one who gets more fiery, when I’m not listened to when those things come up.

Greg Lambert 12:16
Ryan, any other challenges that you face?

Ryan McClead 12:19
Well, I think I think the big one is not letting work become everything. But I think we do a pretty good job of that. We both very much like what we do, we enjoy the work we do with our clients. So in some ways, it’s nice when we had separate jobs at different companies, invariably, the schedules didn’t align. So it would be a day on Thursday that I had to get something done for Friday and would spend all night Thursday night working on it. And you know, that was the one night she didn’t have anything she had to do. And so things didn’t quite match up. That doesn’t really happen anymore, because we’re new tend to be working on the same thing. So if there’s a time that we know, we need to work, we work and it’s not a big deal. We can, you know, we’re we’re both on that same page. And yeah, I mean, I think that’s the, that’s the big, the big thing that’s a challenge is to not work constantly. But I think we do pretty well with it.

Marlene Gebauer 13:25
What are some things you like to do to, like, take a break from work? You know, what are those sorts of activities

Kate Boyd 13:33
Ryan has board games,

Ryan McClead 13:34
so I’ve got a lot of the visual for this candidate. Behind me I’ve got so our company names sent a advise Yes, that’s a is a term from the game go. That is many 1000s year old game. And Sente essentially means initiative. So if you have your pieces in a Sente, a position, it means the your opponent has to respond to that or they’re going to lose some territory. That was why we named the company Sente. But the the real reasons we wanted something that was game related. Shashi, my partner and I were both big board game fans. He’s got a similar collection at home. And, you know, we we enjoy the mechanisms, the structures, the logic behind those tools that sort of gives us an opportunity to exercise our brains in a way that is still it fits with what we do. You know, it’s very much problem solving. But it gets us away from legal technology. So yeah, that’s that’s where Sente came from, but that’s, that’s what the backdrop behind me here is.

Marlene Gebauer 14:51
And I know you sort of have regular board game nights and you know, do reviews of board games as well, right?

Ryan McClead 14:58
Yeah, it was something that we started when Josh and I were both at the OTA and we had regular nights at HighQ. Game night, did regular game nights with the with the team as well? Yeah, I think I think it’s it’s something that we enjoy that that gets people working together thinking together, but is different than working all the time.

Marlene Gebauer 15:26
So I’m waiting for the cheap laugh response here when I asked this question, but what kind of reaction do you get when you tell others you both work together? And that you’re basically together? And that you also work in the in the same company? Do people know? I mean, is it? Is it that widely known? Are people surprised? What kind of reactions do you get?

Ryan McClead 15:52
Go ahead Kate.

Kate Boyd 15:53
So I think it was I don’t know, is this so people who are meeting us for the for the first time as a couple tend to that say, I can’t imagine working with my spouse all the time. Like that’s crazy. So we often get that when when we’re meeting new friend couples, that that’s often the response we get. We have had clients who knew us separately and knew that we were working together but didn’t realize we were together. At that we have had reactions where they’ve said things to each other. Like, I think there might be something going hand between those two. Come on, actually, we’re married, it’s not, we didn’t mean great,

Greg Lambert 16:39
or they thought they were just hyper aware.

Kate Boyd 16:44
As we bring on new clients, we do tend to run about it now.

Greg Lambert 16:48
And I know that Kate gets a lot of really Ryan?

Kate Boyd 16:57
Not at all.

Greg Lambert 16:59
Well, Kate, you kind of talked about this earlier when? Because you are working. And really I mean, there’s at least three of you who are decision makers at Santa Fe, because you get the two of you Plus, you get Shashi as well. How do you handle situations where one or more of you may not agree? This is how we how we go forward? How do you worked that out?

Ryan McClead 17:25
Yeah, so it’s what’s interesting. I mean, Kate mentioned it, how we all come at things from different perspective. And I think that’s part of part of the value that we bring to our clients is, we all have 20 plus years experience in the industry on from multiple sides. But we do all tackle problems from very different directions. And we over the last several years have built up an appreciation for each other’s approach to problem solving. So when we come together with problem, we will often sort of take it on our own and say this is what I would do. I don’t think we’ve never had a impasse. Where it was No, I totally disagree with you. I think Shashi and I probably get more into that than Kate does with either of us. I think she and Shashi tend to agree more. And I’m the odd man out, but I fully trust them. And I think every time we’ve had something that would, you know, even appear to be an impasse or disagreement, it’s not it doesn’t last long, we get to the point where you explain it to me, show me what you’re seeing, well, here’s how I see it, this is what I’m thinking, and almost invariably wind up with a better solution than any one of us would have had on our own. So I think over the last five years, we’ve learned to appreciate that. And those moments when we think I don’t know what this person is thinking, what are they doing, there’s enough to sort of hang your hat on that. I trust that they’re coming at this from a different perspective, and I’m going to learn something here. But we will probably find something that neither of us would have come up with on our own.

Greg Lambert 19:21
And Kate, what’s your opinion, and how was Ryan wrong?

Kate Boyd 19:26
That is true. We laugh that we all have superpowers. And I think all of us really like being part of a team. And I think one of the things that can be lonely when you’re a consultant is that you don’t have that same team kind of infrastructure often. So this, this group really leans into each other, to make sure that ideas are talked through before we start acting on behalf of a client. Hey, actually, I agree with him.

Marlene Gebauer 19:52
What are the interesting things that the two of you are doing now in in legal tech, and I imagine there’s a ton of them.

Ryan McClead 19:59
Yeah. So the one thing to answer, which is it, it is AI. I hesitate to say it. We’re making a lot of interesting stuff with AI. But it is the monster that has eaten every conversation for the last 18 months, raises its head. That’s all we talked about. So there is an element of, okay, I’m tired of this. On the other hand, it’s cool tech, and I love cool tech. And we love cool tech. That’s why you know, why we do what we do. And we’re finding interesting things to do with it that I don’t think a lot of people are doing. So that’s probably the one most interesting thing at the moment.

Marlene Gebauer 20:43
Now, that’s the secret sauce, figuring out how to use it in ways that others aren’t.

Ryan McClead 20:48

Kate Boyd 20:48
I’d say that that’s probably the space where we’re prototyping the most right. And that’s something that Sente does a lot of is help help organizations prototype different technology. Some of the other projects that as a group, we’ve worked on product launches, and a lot of tech evaluations to helping look at different solutions for clients. And both of those have kind of been a focus for the early part of this year.

Greg Lambert 21:17
So normally, you and Ryan, you’ve been on the show, at least at least once, maybe twice. So you’ve taken the time to answer a crystal ball question, but we’re shifting it a little bit and calling out our Valentine’s question. And Ryan, I’ll start with you, and then Kate get get your opinion on this. So if a couple were to come up to you, and get your advice on, they’re considering working together, how do you how do you make it work? And what some good advice that you give to them?

Ryan McClead 21:47
Well, I don’t think it’s, it’s probably not for everybody, you know, I like to think that we’re special.

Marlene Gebauer 21:55
You are special, you are special.

Ryan McClead 21:58
I think if you if you have a good relationship, and you have a good working relationship, it can be quite beneficial and satisfying to to be working together on things. So it’s kind of the best of both worlds. I think, in terms of advice. Even though we live together, we work together, we’re together, most of the time we’ve had, I feel like we have sort of different personas, there’s an element of work me and personal B and work Kate and personal Kate. And we you know, like any couple we have disagreements our personal lives, I don’t feel that those actually bleed over into work. And vice versa. You know, in some ways, the work piece is easier to navigate. Because of what we were saying in terms of how we we know we come at things differently, which actually helps in our personal lives. I think so. I don’t know, I guess be us would be if you could be us, then you could do this. And it would be good for you. But I don’t know what what other advice I would offer.

Greg Lambert 23:11
All right, Kate, what does what does it take to “be us?”

Kate Boyd 23:14
It’s funny, because before I joined, we actually did go meet with friends who are couples who work together and ask their advice, I would say so I would pick up on what Ryan said there is a work persona and a personal persona and make sure that you don’t let the daytime work things bleed into your personal life and vice versa. So I think that’s that’s a good advice. I think that you know, in the in the work setting, know your lanes. So we know where we need to hand off projects and who’s who’s kind of stronger in which areas so that, that we don’t run into conflicts there. So I think that kind of stay in your lane. And then the only one that Ryan didn’t mention that has been really important to me is to maintain my professional friendships apart from Ryan and I know he does as well. So I still make time to go have coffees and see my other professional friends and talk to them not in a sales and business development way just in a you know your people who I value in my professional network, and I want to I want to make sure I carve out time in the day to spend time with them. And I think that’s a really important thing that’s easy to lose when your life and your relationship and your work are all tied together.

Greg Lambert 24:34
Yeah. Great, great advice. So yeah, Ryan McClead and Kate Boyd, thank you both for coming on The Geek in Review and sharing your love and LegalTech story.

Kate Boyd 24:43
Thank you.

Marlene Gebauer 24:44
And of course, thanks to all of you our listeners for taking the time to listen to The Geek in Review podcast. If you enjoy the show, share it with a colleague. We’d love to hear from you. So reach out to us on social media. I can be found on LinkedIn or on X at @gebauerm and on Thread’s at @mgebauer66.

Greg Lambert 25:02
And I can be reached on LinkedIn or at @glambert on X, or you can reach me on Threads at @glambertpod. Kate and Ryan, if people want to learn more about to you or since a advisors where’s the best place to? To reach out? Kate?

Kate Boyd 25:17
So our website is SENTE, S E N T E And we’re active on LinkedIn. I’m on LinkedIn. Ryan is too. I think you’ve got some other handles.

Ryan McClead 25:29
Yeah, I’m not on Twitter anymore. or X. So LinkedIn is pretty much it.

Greg Lambert 25:35
All right.

Marlene Gebauer 25:36
Okay. Thank you. And the love and legal tech music that you hear is from Jerry, David DeCicca and Eve Searls. Thank you both for that.

Greg Lambert 25:44
Alright. Thanks, Jerry. Thanks, Eve. All right. Thanks, everybody.

Marlene Gebauer 25:47
Thank you.

Kate Boyd 25:48
Thank you.

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