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Nakta Alaghebandan

What does it take to build trust in a career, in a community and in yourself? How do you turn moments of uncertainty into momentum and turn reputation into one of your most valuable assets? Welcome to a very special 100th episode of The Abstract. I'm Nokta Al-Ghabandan and I'm chief of staff to Spotdraft's COO, Akshay Verma, who longtime listeners may recall from earlier episodes on the show. Today, I'm joined by a very special guest, somebody who is usually on this side of the mic, Tyler Finn. Tyler is SpotDraft's head of community and growth, and of course, the host and creator of The Abstract. Over the last 99 episodes, Tyler has explored the unexpected pivots, leadership lessons, and career arcs of some of the most interesting voices at the intersection of legal and tech. And today, we get to hear his story.

Tyler has built a career that defies neat boxes, starting in public policy, moving into privacy and product adjacent work, launching his own consultancy and now shaping one of the most interesting legal communities out there today. We'll be talking about risk, trust and how to increase your surface area and how that helps you shape your career. So Tyler Finn, welcome to your own show.

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Tyler Finn

It feels a little weird to be on this side of the mic. I guess I'm getting a taste of my own medicine. But I'm going to take some solace in the fact that you're probably a much nicer interviewer than I am.

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Nakta Alaghebandan

I will go easy on you.

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Tyler Finn

You'll go easy on me.

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Nakta Alaghebandan

Yes. Thank you for letting me steal the mic. I figured we could just start from the very beginning. You originally thought that you were going to go into public policy and move to DC and obviously there was a pivot there. So can you walk us through that?

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Tyler Finn

For sure. When I started my career, when I graduated from college, I had a plan around going to DC. I thought, Hillary Clinton is going to be president, I'd spend some time in DC in college, I'm going to be the special assistant to the deputy secretary of some agency. That election did not turn out how I anticipated, and I think a lot of folks. I ended up thinking, okay, now I've got to pivot. I'm gonna go and work on the hill in some way, shape, or form. And I think I had the lesson very early on that your network and who you know is almost as important or just as important as your resume. And I had people who were advocating for me in DC who were gonna help me find a job. And then I had a friend, a guy who I'd done research with in college, who introduced me to the general counsel of a company in Santa Monica, startup focused on building what is essentially sort of air traffic control for commercial drone operations. This GC and I met and he said, hey, why don't you come and be the junior guy on my policy team? We're doing a lot of advocacy work at the state and local level in addition to with Congress and the FAA. And I mean, on the one hand, staff assistant salaries are not that high in DC. They're like 25, $28,000 a year. You spend most of your time answering the phone. And if you get lucky responding to constituent mail. So this sounded pretty good, right? Going and working for a private company. And it was in Santa Monica. So it was like doing policy by the beach, not doing policy in the swamp. And yeah, I decided, hey, So it was like doing policy by the beach, not doing policy in the swamp. And yeah, I decided, hey, I'll be qualified in a year to go answer phones in DC if this doesn't work out or if I really don't like it. So this seems like a risk that I can swallow whole. I should go for it and try it. And then one thing led to another, and I ended know, most of my 20s living in LA doing various sort of legal and policy things.

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Nakta Alaghebandan

And at the time people were also warning you against going into specifically the privacy field. They were talking about how it's, you know, boring and compliance heavy back office work. So what made you trust your instincts and pursue it anyway?

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Tyler Finn

Yeah, so I'd been with this company AirMap for about a year and a half or so. There'd been some executive changes. I think we'll talk about things that I look for now that maybe I didn't look for back then when I'm joining a company or evaluating an executive team. But I had, and again, another friend who introduced me to CEO of a data company that was looking for a policy and privacy person, and I knew nothing about privacy. And I had a lot of people, as you said, who were who were warning me like you don't want to leave this like cool sexy Drone public policy thing behind to go work in what they thought was essentially just a compliance function, right? Like you you have these laws and you have to make sure the business is complying with them day in day out And it's very process oriented and procedural and it's not going to be that interesting and I think I looked at kind of the macro picture, and GDPR, which I'm sure many of our listeners will be familiar with, was going to be going into effect in a few months. That seemed like a sea change. It seemed like there was a lot of focus on this area, or there was going to be a lot of focus. So I saw that, and I thought, OK, there's opportunity for growth here. There's opportunity to make this into more than just how do I comply with this one little law.

Maybe if Europe's doing this big thing, maybe Congress will get its act together and something similar will happen here, or at least as what has happened, all the states will start to act, right? There'll be more focus on this. I also, I trusted the folks who were hiring me. I was getting hired at the time by the COO and the CFO at the business, who were sort of jointly going to run privacy from a product perspective and from a compliance legal perspective. I trusted them when they said, there's going to be a lot of growth opportunity here for you. And this isn't going to be boring. Don't worry. And I think it really worked out for me. I think if you're interviewing for a job, and the hiring manager or the person who you're talking to, especially if they're an executive, is really hammering or really pushing on, there's tons of growth opportunity here, or we believe this can become much more than it is today if you put in the effort or you show us how you can grow. That's a great sign and something that I would look for and something that I would lean into or I have leaned into again and again.

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Nakta Alaghebandan

And that trust is obviously a two-way street. First, you have to trust them that this is a place where you can grow and prove yourself to them. But what were some of those early challenges when it came to you now building trust with the people that you had entrusted your career path?

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Tyler Finn

Oh, that's a good question. And you clearly did your research here. So, you know, when I entered that business, career path? Oh, that's a good question. And you clearly did your research here. So when I entered that business, and this is not going to be, I think, dissimilar to the situation that there's situations that lots of our listeners have dealt with before. There'd been a lawyer in the role before for a short period of time who, we'll call it maybe alienated some key stakeholders in the business with a slightly more risk averse approach to privacy and compliance. So when I stepped in, I was almost walking on eggshells a little bit, right? It's like, okay, the product managers, they want you to be here, but they're not sure what you're going to do. And are you going to be like the last person? And the sales team, frankly, probably kind of thought like, we'd rather actually not backfill that role. We'd rather not have someone there.

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Nakta Alaghebandan

They're like projecting that trauma onto this new person that was in that old role.

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Tyler Finn

Correct. And did it all wrong. Yeah. And so, I mean, I think there's a few things that you do. I mean, one, like you go really deep and you not only learn the subject matter, but you also learn the company, right? You really need to understand what are these teams incentives? How do they tick? What are they driving towards? Where are the growth areas for the business? Where is revenue coming from? Why, if I decide to take a hard line on something, might they oppose me? I should think that through before I take the hard line, right? Again, not unusual to our listeners, but I think a no, but, or a yes and, is always better than just a flat no, right? If someone's come to you and said, hey, we really wanna build out this new feature using this new type of data that we're gonna collect, and maybe I as the privacy guy have some concerns about either what that type of data is or how it's going to be leveraged, just saying to the product manager, like, nope, we're not doing that is probably not going to be the right way to engender long-term trust or build a relationship with that person, as opposed to really working collaboratively with them.Because ultimately at the end of the day, if you're in a business, the long-term goal is to build great products or offer amazing services, grow the business, grow the business in the right way over the long run. And so I approach this very much from the perspective of I need to understand everything I can about my job, the privacy world. I also need to understand a lot about what our product team and engineers care about and where our revenue is coming from and where it's going to grow. I'm going to try to see that whole picture. And if I can do that and then present my ideas or present my pushback in the right way, we're going to work together and we're going to be a team as opposed to me being this sort of advisor who's sitting off in the corner in his ivory tower who's trying to build a perfect compliance program, but not a compliance program that meets the needs of the business.

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Nakta Alaghebandan

Completely, and I feel like the right high trust approach to collaborating with anybody is always defaulting to being a high context person. You want to explain why you're doing things instead of just expecting people to buy into why they should follow your lead. So that's definitely, yeah, I think it's really important to keep the high context in mind. And it's interesting because you eventually ended up becoming the person that they would send into all the super strategic, high anxiety customer conversations. So how'd you go from maybe a trust deficit to being the trusted calmer of anxiety amongst customers?

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Tyler Finn

I mean, I think there's two steps. I mean, I think one, you have to build trust with executive stakeholders, right, with the C-suite probably. And this is also, this is a smaller, you know, venture-backed sort of company, a couple hundred people, a few hundred people. So it looks different, I think, if you're at, you know, a large multinational corporation. I'm not speaking from the perspective of someone at Meta, right, let's say. But you have to build trust with the C-suite, but you also really need to build trust with the layer of other stakeholders who are really on the ground making decisions day in, day out. Those VP of sales, regional vice presidents, VP of customer success, director of product management, right? I mean, those folks are not only going to be the people who are like you're ultimately talking to day in, day out, but they're also going to be your biggest advocates in the business or they're going to... When a deal gets slightly changed and then everyone goes to meet with the CRO or the chief business officer to talk about why the deal is going to be changed slightly based on your advice. You want that RVP saying, I worked with Tyler on this and this is the right path and this is the right thing for us. So we're in this deal review process, please approve this deal. Tyler signed off, I've signed off, let's do this together. So building that trust is important. I have one story that I think is good here. One of the guys that I worked with and for, I guess, in a sense, our CRO, who's gone on to be the CEO of a company in the music data space, really interesting guy, tall, kind of laconic, serious British man, likes to go on 50, 100 mile bike rides on the weekends, right? He was not known for being effusive in his praise, let's say. Like loyal and dedicated to his team and an amazing manager, a great executive, but not exactly like effusive in his praise. And when we would do sort of major policy changes, update a privacy policy, I liked to send out an all company email about this sort of thing. I thought internal communication was really important around these topics. And I sent one of those out and he responded to it within 15 minutes or so. And it was very simple. He said like, this is very important work and everyone should pay attention to this. Regards, Rob. Or whatever he said, best, Rob. And very Rob, like very short, very to the point, right? I guarantee you that the sales team suddenly went back and re-read that email all the way through. Winning the trust of stakeholders like that is, I mean, I wouldn't even say it makes you better at your job. I think it's the only way to do jobs like this. Yeah.

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Nakta Alaghebandan

Right. You can't, you need your team's buy-in to be able to successfully do what you got to do in your role. And I mean, going back to this idea of building trust by defaulting to a high context approach, you said that your work has often sat at this intersection between product and strategy and legal. So I'm sure you had to have a lot of context on all of those domains. What makes that intersection meaningful for you?

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Tyler Finn

Yeah, and I go back, I mean, I'll answer the sort of second part of your question about like, how do you get put in high stress or situations with difficult customers or answer that, I'll answer that along with this one. I mean, I think that I have always… After you figure out the foundation, right? After you understand, okay, what does our product do? Where's the revenue coming from? What sort of laws or what sort of regulatory environment are we affected by? Understand some of those basics. Then you wanna see the whole picture, right? So you start to ask other questions like, who are our allies in the ecosystem that we're

operating in? Who might our detractors be or our competitors? Why are they doing what they're doing? Not just like, this competitor is doing this thing or saying this about us, or Google or Apple is affecting our business in a major way, and we just take it for granted that they've decided to do this, right? Like, understand incentives, understand why are they doing this. When you start to see the whole picture, I think you get given more ambiguous projects, projects that other people might not be able to solve. You show that you're thinking about things from a very cross-functional perspective. And I mean, ultimately, these days, that's what really great executives are. And I think we've seen a bit of an evolution there. I've been able to watch for the past five to 10 years, the sort of GC role evolve in some ways. GCs don't think of themselves as, I'm the lawyer, I'm over here, I provide the legal perspective, I only chime in in the executive team meeting when someone says, is that compliant or can we do that under the law? People think of themselves as operators, as leaders in the business, as executives who are ultimately responsible for the growth of the business and the long-term prospects of the business.

And so the more that you can work on highly cross-functional projects, or the more that you can see the whole picture as in, okay, how is the decision that we're making over here around the regulatory environment going to affect the product, which is going to affect revenue, which is going to affect our financial picture, which is going to affect our ability to make the acquisitions that we want to make, or we need to access capital or debt in a different way, right? You want to see the whole picture. That's how you level up.

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Nakta Alaghebandan

Yeah, you want to make those connections that you might usually find in a different domain. How does that have an interesting impact in a different area? And I personally, as my experience in the chief of staff role for quite some time, I believe that the magic really does happen in the gray areas. Not just within a work context, of course, and I know, I mean, we can talk a little more about all the inflection points over the course of your career, all of those gray areas. I mean, you eventually left a job that you were totally succeeding in. You've experienced being laid off. You started your own consultancy business. What was your mindset in those moments of sitting in the gray area and experiencing that uncertainty?

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Tyler Finn

Yeah. Can I say one more thing on the last question? Of course. I think the other thing about figuring out that cross-functional picture or figuring out that bigger picture is that it does take time. And I don't think there's anything wrong with people who have, these days, spent 18 months at this company and 24 months at this company, and maybe one company wasn't a good fit and they were only there for nine months and then they go there's nothing wrong with that. But I think figuring out the bigger picture or having the relationships with other stakeholders in the business or the institutional knowledge that comes along with being at a company for two years or three years or five years I mean eventually it gets stale. I think, you know, people probably shouldn't stick around companies for 15 years so much, at least in the space that we're operating in.

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Nakta Alaghebandan

Unless the company is totally evolving into a whole different piece.

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Tyler Finn

Totally, or maybe, I don't know, maybe you keep getting promoted and now you're the CEO, right? But I do think it takes time, right? And there's nothing wrong with showing up in a business and saying, I'm gonna get this one thing done and I'm gonna do a great job and I'm gonna leave in 18 months and that's fine and I'm onto the next thing. Like that's totally cool. But if you want to see this bigger picture, you need to spend time, I think, either in the company or at the very least in a sort of industry or space or ecosystem, because that's how you're gonna be able to draw the connections.

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Nakta Alaghebandan

Yeah, and you can't upload judgment into your brain. It takes time to cultivate that.

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Tyler Finn

Totally. Yeah, I think a lot about judgment. We can talk about that. Yeah, definitely. Yeah, I mean, navigating ambiguity or uncertainty, I've had to do a lot more of that than I ever would have anticipated in my career. I mean, I thought I was gonna be in DC and then maybe go to law school and then be a prosecutor or something. And clearly, that is not the path that I've had. And I think that you can become affirmatively more comfortable with uncertainty and ambiguity. You can learn to lean into it. You can modulate your risk tolerance over time. Part of that I think is also how much risk you're willing to incur in other areas of your life or the practice that you create around that, right? I'm gonna sign up for, it doesn't have to be physical, but I'm gonna sign up for this long race and I don't know if I can do it and I'm kind of scared about that. If you go through experiences where you're scared outside of the workplace, I think that you can draw on those when they show up. And it's like, I made it through this 50K trail race sort of thing. I just got laid off. I know this is gonna be difficult. I know this is going to be hard, but I know I have the fortitude and I know I have the perseverance to push through it.

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Nakta Alaghebandan

I mean, we also tend to incorrectly think that risk-taking is in some part associated with a bit of thoughtlessness, but I think it's a skill to take calculated risks. What advice would you have for listeners on how to hone that skill of taking calculated risks? Obviously, there's a lot of known unknowns and also unknown unknowns, but how do you get comfortable with trusting yourself in those gray areas?

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Tyler Finn

Yeah. I mean, usually if you're trying to make a decision, the risk comes from a lack of perfect information, right? Yeah. So you're always trying to strive for more and better information. I think it's important to trust your gut, but I also think it's important to talk to people that you respect about this. I am a big proponent of having mentors, former bosses, people that you've worked with, that you think either have long life experience or deep experience in your industry or experiences that you haven't had or perspectives that you haven't had, right? Go to the... if you're considering a new job and it's not gonna be awkward or go to the sales leader and ask them how they see the role that you're taking on or the company that you're looking to join or

you know the new part of the ecosystem that you're you're thinking about moving into. They're going to help you see whether this is really risky or or. I think people sometimes tend to over-index on the risk that they see, when really what they need is sort of better information or a broader perspective.

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Nakta Alaghebandan

Yeah, calibration also.

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Tyler Finn

Let's talk about- And sometimes people will also back you off. I've had that too.

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Nakta Alaghebandan

Yeah, they'll walk you off the hook.

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Tyler Finn

They'll walk you back. It's not to say that you should always lean into, you know, someone comes along and offers you something that sounds really amazing and you're like, oh, maybe I should do it. And then you go and you talk to a bunch of folks and they're like, okay, we're not saying that that's not gonna work out or it's gonna totally blow up your career, but sit back and think for a second and pause for a second, right? Yeah.

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Nakta Alaghebandan

And so you told me a really funny story. I really wanna get more details on it here because I think it's a perfect embodiment of trusting yourself until the trust emanates from you and people want to trust you. I wanna talk about TechGC. Oh, sure. And how you went from being an uninvited 22 year old at a GC dinner to someone helping build the organization over the course of five years. I mean, that says a lot in such a sentence.

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Tyler Finn

Yeah, my, this is the first GC who hired me after college. I have a lot to thank him for. He's a friend of mine, Bill Goodwin. If you've ever met Bill, you know that he wears Hawaiian shirts, rain spooners every day, tucked into khakis.So he's got Sperry's on. Maybe I've seen him in a tie once. He's really, he's an amazing guy and he's a real character. And so he's the type of guy who has the, you know, he's got the chutzpah to like invite his junior policy guy to the first or second Tech GC dinner that was being held in LA. You know, at the time I thought I might wanna go to law school. He said, you should come here. You should meet some of these people. You should introduce yourself to the guy who's organizing these. And I did. And Kiran and I, Kiran is one of the guys who started TechGC and has really grown it to now the L-suite, like all that it is, and the F-suite, and the E-suite for CEOs, and turned it into a really amazing, not just community, but really amazing business. Kiran and I started to talk to each other, get to know each other a little bit. At the time, he was doing it full-time. Greg, the other co-founder, was still the GC COO at FirstMark, a VC fund here in New York. They had, maybe Chris was working with them doing some marketing stuff and then like a couple of Columbia Law students basically. And I basically raised my hand. I said, look, I'm on the West Coast, you're all in New York, you want to be doing more events here and doing dinners in San Francisco and Seattle and LA and you probably don't want to hop on that TransCon flight like every single week or every other week. And one thing goes you know turns into another and you start to do good work and ran the list, moderated the list serve for many years like sitting there approving emails all day on my phone quietly. I organized a lot of their webinars. I hosted a lot of their West Coast dinners. If you do good work, you know, the great thing about doing good work, I think, and the sort of like tragedy of doing good work is people start to give you more. Yes. So, you know, there were, especially during COVID, when the GC community, our population was dealing with like, how do we get people out of our offices? What do they need as they start to work from home? How do we deal with like PPP federal funds? What decisions do we make around that sort of thing? There was a lot of work. I mean, I was working until two in the morning most days helping organize these sorts of things. But I would not be here today in any capacity like I am without that sort of experience, without getting to know that community, without all that I learned from the way that really Kiran and Greg set a strong ethos and built that community in, I think, a very intentional and particular way.

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Nakta Alaghebandan

Totally, I was just going to say, it sounds like that dinner was a very fateful pivot into your community.

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Tyler Finn

Yes.

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Nakta Alaghebandan

Chapter and this facet of your being. And you've said, of course, that Tech GC, all those experiences really shaped your philosophy on community. So what lessons from that time really still guide you today?

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Tyler Finn

The members of a community have to be front and center. You know, Greg these days will go on stage and give a sort of like product presentation on their like online platform. Maybe once a year, Kieran will get on stage and talk about an acquisition that they've done that they're excited about, or some of the vision for how they're going to grow it over time. But they were extremely intentional about, we have a steering committee, we have members in every city that are our leadership, they have a global chair. It was all about the members, it was not about Kieran and Greg. And that flowed down into really what this is about is peer-to-peer interaction, peer-to-peer learning. And so, yeah, we will bring in sponsors, whether they're law firms or folks like Spotdraft, legal tech providers, other sort of privacy tech vendors, insurance brokers, et cetera, will bring those folks in when they have an important perspective to share or if they have something to bring to the table, but not just to fund the dinner and walk away, right? Because really what it needs to be about is sort of peer-to-peer connection and peer-to-peer learning. And they've always taken... I mean, this I think dovetails a lot with things that I've worked on in my career. They've always taken a very long-term view of growth. grow something slowly and intentionally in a way that builds trust and builds sort of like real sticky cohesive connection than to grow something very quickly that then flames out.

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Nakta Alaghebandan

Yeah. Organic, not GMO community. I think that the best type of community is the one where...

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Tyler Finn

I love that sort of phrase. Did you just make that up?

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Nakta Alaghebandan

Yeah, just came up with it. I feel like the right approach to building a community is exactly like you say. The builders of that community are more like the frame and the community itself is the beautiful painting that you're there to see and experience. What else do you think really makes a community work?

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Tyler Finn

People have to be willing to share. I mean, that goes back to the trust piece. You know, I mean, go to a happy hour, meet a few new people. I mean, that's a good thing too, right? But I think a really strong community is one in which people feel a willingness to share something about themselves, a problem that they're dealing with at work, a need for help on a particular task or with a project or for a firm recommendation, or people feel a willingness to share, that's a great sign of a healthy community. Yeah and I guess that would

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Nakta Alaghebandan

also be another helpful way as a community lead to help enable that comfort and safe space to be vulnerable without really making it obvious that you're also there. Just like providing the right vibes and structure to encourage that type of connection.

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Tyler Finn

Yeah. If I host a dinner or an event or, I mean, my intention is not for it to be about me or me talking or, I mean, this is weird for me to be on this side of the mic because I feel like I'm a pretty good talker, but that's not what I hone my, I wanna be a better question asker than a good talker.

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Nakta Alaghebandan

You wanna enable the storytelling.

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Tyler Finn

Correct.

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Tyler Finn

A facilitator.

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Nakta Alaghebandan

Yeah, exactly. And all of that, I think, also just keeps boiling back down to trust and how also reputation comes from trusting somebody. Like I don't think it's, I mean a good reputation at least is associated with trust. And I think, and tell me if you agree, these sound like two of your big North stars. If we can pick two North stars. How do you think about building trust and reputation in community contexts, in a community role where, you know, it's not really such a structured, defined job description, like you're really paving the path and trying to make this organic thing. How do you do that with just these really intangible but super important qualities?

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Tyler Finn

I mean, there's tactical things that you can do, right? This sort of like content that you're creating, which hopefully you're getting advice from members of the community on, has to be really, really good and top notch and interesting. You have to make small decisions about, if we're gonna host a spot draft dinner, are we gonna have a spot draft, like standee roll up thing at the dinner? Probably not, right? That's not the sort of thing that's going to engender long term trust. Who you let into the sort of community or the way you approach that, I think is also a very important decision that should not be taken lightly, because it's gonna change the sort of tone and tenor of the interaction between members. But I think a sort of broader view, whether it's community or a company that you're building, any organization, I guess I have a view that, especially in a more interconnected world in which people are very online, there's a lot of sort of constant controversy and churn, focusing on trust and reputation, meaning do the stakeholders that care about us trust us? Do we have a strong reputation with them? Are they going to support us? I really think that's one of the only ways that you build a long-term, durable business. I think otherwise what you're building is, and it may be very profitable for a period of time, but I think it's extractive and it's not built for the long run.

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Nakta Alaghebandan

Yeah, not stable. I think trust is all about being on the same page, on the same footing. And even if you don't agree, you see how the other person sees you can empathize and how can anything be long term when you're on unstable footing. And so going back to your consulting era which is also all about building trust like how do you build a consultancy from the ground up where people want to come to you and they trust your opinion, like you have to have your reputation precede you, so to speak. So SpotDraft, interestingly enough, came on your radar as a consulting client. So how'd that happen? And how did that turn into you now joining SpotDraft's team full time? Quite a journey.

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Tyler Finn

Yes, and it wasn't how I expected it to play out either, by the way, which I think is a good thing. Yeah, SpotDraft was sponsoring TechGC events. I started to see SpotDraft at more events. I met Shashank and got to know him a little bit. Vic, who used to be on our team here in New York, now has gone back in-house to legal roles. Rohith, chief product officer, started to get to know them a bit. And I think at the time, Spotdraft was dealing with not a product market fit issue, not really a growth challenge, more of a messaging refinement problem, right? Which was we're coming to and trying to grow in the North American market. We want to make sure that the way that we're speaking to the market is really resonating We need to have a stronger back and forth with the market or the community or the sort of ecosystem here So that we were we're refining the way that we're talking about our product offering the way that we're engaging the market and In getting to know those folks It seemed like they could use a little bit of help. Like not like a lot of help, but a little bit of help. 

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Nakta Alaghebandan

Tell us more. 

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Tyler Finn

And so I took on a sort of like, you know, short sort of term consulting arrangement. Our CEO Shashank basically used that as a recruitment tool to try to bring me in full time. I think at one point he even said, can I continue to pay you as a recruitment tool to try to bring me in full time. I think at one point he even said, can I continue to pay you as a consultant so you don't take another full-time job until you take the one that I'm offering you? In many ways, I would actually, I would look at this a little bit differently maybe than I had before that experience. I think it's really great in some ways to sort of like try before you buy like this. Where I got to know the Spotgraph team, I got to work with them on some projects. I got to see how I interacted with other people in the marketing org before I joined the company. Look, I understand that people don't love like, we're gonna give you a six month provisional period in which you're a contract. That feels a lot more like we are evaluating you and whether or not we want to keep you. And that feels a little bit different than this did. But I advise, I mean, I talk to a lot of folks who are between jobs, whether they're general counsels, commercial lawyers, privacy lawyers, or privacy managers, legal operations professionals. I advise a lot of them to stand up a consultancy. It doesn't have to be huge. You can continue to look for full-time employment while you're doing some consulting work. Try to tap your network. It's not always going to be the people that you expect who will come on as clients, case in point. Two or three clients may not be plenty for the long run for you, but is plenty. It gives you something to talk about in interviews, and you never know when one of your consulting clients is going to end up turning into your next sort of full-time opportunity. And so that's what happened with me. And yeah, the rest is history.

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Nakta Alaghebandan

And so then you got to bring all the wonderful philosophies and learnings from TechGC into this role. But then how has your perspective on community building over the last three years since you've joined Spotdraft changed?

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Tyler Finn

So I've had to, I mean there's been a lot of learning for me, I mean I've had to learn the sort of like legal ops community in a way that I did not before. I've had to think about community as a counterpart to marketing in a way that I was not thinking about it before. I mean, I think in many ways actually, community is, I wouldn't even say, community is not the future of marketing. Community is a lot of what marketing, I think, is becoming or needs to become, right?

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Nakta Alaghebandan

It's the storytelling. 

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Tyler Finn

Especially in a B2B business like we have in which these are very sophisticated buyers. They don't make decisions quickly because they know not only is the sort of value of what they're buying relatively expensive. I mean, I think SpotDraft is reasonable, but relatively expensive. The unwinding a wrong decision is also painful. So they're very sophisticated buyers. They're not generally going to pick up the phone and answer from a very, very junior sort of BDR sales rep. They're going to want to, when they go out to evaluate a product offering, they're gonna want to know your reputation in the market and think that you have a good brand. Probably have seen you in various places as a bit of a thought leader. They're going to call up their peers, I think, and say, hey, who are the three vendors who we should be looking at for this sort of offering, or who would you recommend? So I think about community differently in that way as well.

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Nakta Alaghebandan

Would you agree that it's this extension of marketing, it's marketing through empathy and trust building and storytelling?

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Tyler Finn

Yeah, I mean, that's a good way to put it, yeah. I think the only reason that I would say community is not or should not be... And I'm not talking about from an org perspective, I'm just talking about from a perspective perspective, consumed by marketing or become totally part of marketing, is I think that from time to time, community should serve as a slight counterweight or counterbalance to some of what marketing or some of what sales might want to do. I think it's helpful to have someone in the business who's thinking with trust as their sort of core lens, as opposed to demand generation or as opposed to revenue and ARR, right? That's going to give you a longer term perspective.

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Nakta Alaghebandan

Yeah. One more question on your experience coming into a company setting. And you've said that your priorities and how you evaluate companies have changed, at least within the context of your career path. What do you care most about now that you might not have considered earlier in your career?

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Tyler Finn

Well, I mean, that is great actually in the context of community because I did not want to get hired into a role where my title was nominally head of community. And then I was immediately given a quota and I was told like, you need to go out and quote. That would not have been, I mean, Shashank would have never done that, but that would not have been the right fit. So I mean, of course you have to like, if you're evaluating a company or deciding to join, you have to think about things like that. Like, what is my role gonna be? Am I gonna be set up for success in my role? I think that one thing that I prioritize a lot more now than I used to is who the CEO is. I've worked for six or seven, six I think. I mean, I haven't had the longest career, but six different CEOs at these companies. I've been through CEO transitions three times.

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Nakta Alaghebandan

Wow. you've seen a lot of leadership styles.

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Tyler Finn

Correct. And there are... And by the way, CEOs and executives are people too. So no one should be expected to be perfect or the perfect leader. Some people are better at motivating their teams to accomplish incredible things. Some people are better at being super analytical and thinking deeply and cerebrally and offering great advice. Some people are better at making fast, quick decisions in a time of crisis, right? Nobody should be expected to have like every single one of these character traits all at once.

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Nakta Alaghebandan

And maybe sometimes those traits thrive at different stages of the company.

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Tyler Finn

Correct, a wartime CEO, I mean, I don't love the wartime metaphor actually, but like the wartime CEO is maybe different than the CEO that you want when the company's doing really well and has a $7 billion market cap in the public markets and growth is perfect and like 15% or 20% year over year. I mean, different styles might be that it's possible, but it is very rare that an executive team, rung of C-suite that works with the CEO, is going to be able to make up for a CEO who is really, really deficient in some area. So I try to do a lot more evaluation of what's the CEO and what's the executive team, even though I'm not joining that team, right? Who am I joining? Who are they going to be? And then also sort of like, who are the people who I'm gonna be working with?

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Nakta Alaghebandan

Totally, like what is the community within the company and even more specifically, how does the CEO view the importance of community amongst the leadership team?

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Tyler Finn

Yes, absolutely.

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Nakta Alaghebandan

I think that's super key, especially for helping make up for one another's deficiencies I mean, that's why you have a C-suite, right? Like you're not gonna be good at every single thing at every single moment. And... 

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Tyler Finn

If an executive team isn't communicating well together, if there are factions within the executive team that are constantly opposed to each other, I mean, it's tough to figure out some of this stuff in the interview process. If the executive team isn't... I like this term, I know Akshay likes this term, the sort of like, we need to disagree and then commit, right? We're gonna hash this out around the table, ultimately we've decided that one person or we are going to make a decision, we are gonna pick this path, we are going to run together 100% at what we've decided. We're not gonna let you kind of like drag your feet over here to slow us down to maybe get what you want, right? I think if the executive team isn't functioning well, it's really hard for other people in the business to do their jobs well.

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Nakta Alaghebandan

What's something you wish you saw executive teams, C-suites do more of through that community lens?

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Tyler Finn

Well, I think it's talk to each other.

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Nakta Alaghebandan

Yeah, it is that simple.

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Tyler Finn

And then I think it's talk to the company. I think that if you leave things unsaid in an organization, if you don't affirmatively communicate with folks, it's not going to be this quiet void and everybody keeps going about their day to day.

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Nakta Alaghebandan

People are gonna fill in the blanks.

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Tyler Finn

Correct.

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Nakta Alaghebandan

And that's gonna be way harder to rope in.

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Tyler Finn

I was gonna say, assume the worst.

Nakta Alaghebandan

Definitely also happens. It's just like so many different narratives and then you have to reel all of them in with your company lasso. And it's just so much harder than being, taking the high context approach from the get-go.

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Tyler Finn

This requires intention, I think, because executives, especially, we are very busy people, right, being pulled in a lot of different directions. Because executives especially, we are very busy people, right? Being pulled in a lot of different directions. You have to be very intentional about the way you communicate with your business and with your people. And I mean, if we go back to the sort of like small lens of doing privacy work, you wanna roll out a company-wide policy, you don't just like sit down and talk to outside counsel and decide what you're going to do and then write it up and then send out one email. You do the pre-work of going and talking to the different stakeholders and getting their buy-in ahead of time and making sure that they're going to be champions for you when it rolls out. And they may even be the ones that present it to their teams. And then you might preview it before you actually roll it out and let people know that it's gonna be coming out. And then people need to think more, I mean, people need to think more like marketers. That's not the end of that list, by the way, but I'm not gonna talk for like five more minutes about.

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Tyler Finn

Right? People need to think more like marketers, I think. And executives need to think more like… 

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Nakta Alaghebandan

Storytellers.

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Tyler Finn

Storytellers.Yes. 

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Nakta Alaghebandan

Yeah. So, I mean, community is definitely a state of mind within every context and every group of people that we find ourselves in. I think you're just, yeah, you're way more intentional and strategic about it. It's literally what you live and breathe. Let's talk about…

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Tyler Finn

I have the headspace and the time to be allowed to do this.

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Nakta Alaghebandan

Exactly, and so I wanna talk about the abstract. So I wanna get a little meta. I want to know why did you start the podcast in the first place? And did you see a gap? What were you trying to fill with that? And how did you pitch it to the team?

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Tyler Finn

It was not my idea. Uh, yeah, I will not take credit for this. It was Rohit who runs product and had been running marketing at the time. And I think he looked out at other companies and he's like, lots of other companies have podcasts, we should have a podcast. Tyler, we just hired you. You don't seem to have a full plate yet, do this. And so then it was incumbent upon me to run with it and come up with the title and work with the design team, which was very fun, by the way. Like work with the design team on the logo. And at the time or at the start, I knew I wanted to do something around, well, I knew we needed to encompass all that legal is. I did not wanna do something that was just like, I'm only going to interview GCs or CLL, that felt very narrow. I wanted it to be about professional development in some important way, and personal development. I wanted people to tell stories. I didn't want it to just be advice. This was not meant to be a, get on the podcast and talk to me for 45 minutes about all the steps you took in the 18 months leading up to the successful IPO of your company. That also felt too like CLE, boring, narrow. And so I think what we've landed on over time, and hopefully, I mean, I've gotten better at...

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Nakta Alaghebandan

The title is starting to make more sense.

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Tyler Finn

Yeah, exactly. The abstract, right? Yeah. What we've landed on over time is we wanna have folks who are in legal or legal adjacent roles, who are legal professionals broadly. They might be GCs or CLOs. They might be a head of legal ops in a business. They maybe were a lawyer at one point in time and now they're an executive recruiter or they're a CEO or they're a COO or a consultant.

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Nakta Alaghebandan

As Akshay likes to say, a recovering lawyer.

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Tyler Finn

A recovering lawyer. I like to talk to them about their career paths, success that they've had, real trials they've been through, personal experiences that they're willing to share. I think, you know, the idea is one, there's no one right. And this is self-serving. We've been talking about my career path today, but there's no one right career path. So there's nothing wrong with, I went to Harvard Law School and then I went to Cravath and then I joined Citigroup and I've been at Citigroup for 25 years and I have a house in East Hampton. Like's great. I really love that right. That's not the typical profile or persona that I'm looking for when I when I bring guests on because I want to communicate that you know careers are not straight lines that you can chart a really meaningful career even when unexpected things happen. I also think over time, as I've built... As I've gotten probably better at interviewing, but also as I've built more trust with my audience and also with my guests, right? credibility with future guests You know, I want to have folks on Who are willing to talk about really difficult moments in their careers? I mean this could be you know, it could be like Dan Haley who has had testicular cancer twice and has been through two CEO changes that were totally unexpected. One where Hedge Fund came in and ousted his CEO and one where she had a massive stroke and you know or like a Mark Maron who you know woke up and he was the GC of Barstool Sports and the CEO of Barstool Sports tweeted overnight, my lawyer's an idiot on... And so he wakes up to like 15,000 notifications. I don't wanna have those conversations because they sound...

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Nakta Alaghebandan

Sensational.

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Tyler Finn

Sensational, that's the word that I'm searching for. I think that other people who are going through similar experiences, or even sometimes slightly less dramatic experiences, are going to feel a little less alone if they're able to hear from one of their peers or someone that they really respect how they've been through something like that and come out the other side.

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Nakta Alaghebandan

I love what this type of storytelling format enables because I don't know, I feel like especially over the last 20 years, it felt like we were all living in these black boxes and thinking that everybody is just climbing this ladder. So if I'm not doing that, oh my God, I'm behind. I've done it all wrong and now I can't catch up. And now you're just you're seeing this beautiful tapestry of all these different experiences and career paths, the unexpected, and it's really, really cool what you can take away from that and how much more interesting and insightful what you might have to offer to others can be. And so you've now interviewed almost 100 guests. How have those conversations from the show changed how you show up in your own work?

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Tyler Finn

That's a good question. I mean, I think I have a strong belief in sort of like grit and perseverance. And I think that my guests have borne out that that is right. That does not mean by the way, like don't take care of yourself or push everything to the side. Or I mean that more in the sense of challenging things or hard things are a part of jobs or roles like this. And if you take a long run view of your own life and career, you don't have to be a nihilist and say, none of this matters or I'm not gonna be talking to that boss in 15 years, so I don't have to be a nihilist and say, none of this matters, or I'm not gonna be talking to that boss in 15 years, so I don't care. That's not what I'm saying. I'm saying, you can get through this. Lots of people have been here before, they've gotten through this. You've been here in similar situations before, you can get through this. There's going to be a light on the other side of the tunnel. So I think my guests have borne that out. Most of these folks are people managers. A common theme or something that I've heard that I think more about today than I used to is not what impact can I individually have on this business or organization or community, but how can I create opportunities or support other... To empower others, or how can I support others so they can be better at their jobs or they can accomplish things? I can't write 15 blog posts for us. I mean, maybe I could. I can't write 15 blog posts for us a year, but I can coach our blog manager on how to improve the quality and topics and of the blogs that we're creating as a small example.

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Nakta Alaghebandan

That's a huge spot draft value too. Like can't work in silos and winning is about winning together. If someone else is winning, that means we're winning too.

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Tyler Finn

This isn't really something that I practice in a day to day, but I think that all of the conversations with my guests, I for a long time, this is gonna sound very corny, but... Go on, it's a safe space. I really believe, truly believe that individuals, individual people are capable of extraordinary things and are able to make unexpected impacts on the world around them. And that does not mean that it always has to be like, you know, I gave some speech on the National Mall in Washington, right? It's not what I'm saying. But if you look at all of the guests that I've had on, I've never asked them this question, but I bet if you asked them, would you consider yourself to be an extraordinary person? I think most of them would probably say, no. Well, like that guy MLK was pretty amazing, or I really loved Barack when he was president, but you look at the sum total of what they've done, the organizations that they've helped run, the thousands of employees' lives that they may have changed, the markets or communities or that they have built that did not exist before, to say nothing of sort of like the flapping of the wings and the impact that has made on the rest of the world. You don't have to be even like Dana Rao at Adobe to have made a huge impact on the world. Think of Kiran and Greg, right? And what TechGC has done, you know? TechGC is good business, it's not a huge business. They're not gonna be worth billions of dollars, probably, maybe Kiran wants to be. But think of all of the sort of like peer-to-peer connection, education that has occurred as a result of what they've built. So that's a big takeaway for me, is you look at the people on the podcast who've been here and if you're listening to it, you should probably either say, well, you should say like maybe I wanna be like that someday and then maybe you should ask yourself like maybe I'm a lot closer to that already.

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Nakta Alaghebandan

And- Maybe I just wanna be more of me and not, you know, tamp it down. And that reminds me a lot of something you and I talked about earlier and it really resonated with me, this belief about increasing your surface area. I love that description because I think a lot of people might be afraid to take up space. It might be related to that feeling risky in some way or, you know, scary, rejection, all of that. How can you explain that concept a little more for the listeners? What do you mean by surface area and how do you think people should apply it to their own careers and just lives in general?

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Tyler Finn

I think Kiran might've used that term. I don't remember exactly, but I think I may be stealing that from him. And there's a couple of ways that I think about that. It's a better way to think about growing your network. Growing your network should not be about, I went from 5,500 LinkedIn followers or connections to 5,750. hundred LinkedIn followers or connections to 5750, right? Growing your surface area means like there's a lot more people out there who are aware of me, who might be champions for me, who might support me, might want to help me get to the next stage. So I mean, I don't know where my career is is gonna end up, but I don't think it's gonna be by going online and applying to 17 or 170 roles on LinkedIn. I think it's gonna be by continuing to increase my surface area. There's another aspect, I'll conflate it with another concept that my prior boss, very cool guy, he is these days the CFO of an organization that does all these amazing challenges. They'll raise $100 million to try to have a robot go across the desert or... That's awesome. Yeah, very cool. He would always say to me, like, Tyler, remember, knowledge accrues, right? And I... Meaning... Very true. You're sitting here and you're in some product meeting and people are talking, talking, talking, and you're like, well, I don't really care about our consumer business. I'm not worried about that. But knowledge, you never know when six months down the road or six years down the road, you're going to draw a connection. You're going to pull that tidbit. And so I kind of think about that in the realm of increasing your service area or in the same vein as increasing your surface area or in the same vein as increasing your surface area as well. I think people or folks, they... You wanna live with intention, but sometimes it's just about absorbing all the world has to offer and seeing where that leads. And so, yeah, it's not about networking. It's not about reading every book that you're supposed to read or every single book that one of our podcast guests has recommended. It's not about trying to memorize everything about the business. Yeah.

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Nakta Alaghebandan

Being a sponge is not passive work. You're synthesizing, you're listening, that's active. Yeah. Yeah. I prefer not to listening, that's active. Yeah.

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Tyler Finn

Yeah. I prefer not to be described as a sponge, but no.

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Nakta Alaghebandan

But like the sponge approach.

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Tyler Finn

Yes.

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Nakta Alaghebandan

So, okay, it only feels right to wrap up the conversation with a few fun questions that I think you'll recognize. Yes. The Tyler special, if you will. What is your favorite part of your day to day?

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Tyler Finn

If it's not playing tennis or going on a run, I'm very lucky to get to do lots of context switching and I've had that as a part of or as the sort of like the feature of my roles for a long time. I love that. I love that in one minute I am talking to a GC on a coffee chat that has no goal. Later I'm interviewing a head of legal ops for this podcast. Then I'm working on a script. Then I'm looking at our product marketing docs and providing feedback, then I'm like hosting a webinar, then I'm helping our team with talking points for some interview that our CEO is doing. I love the context switching.

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Nakta Alaghebandan

Keeps it fresh.

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Tyler Finn

Absolutely.

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Nakta Alaghebandan

Do you have a professional pet peeve?

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Tyler Finn

I do. Who doesn't? I do. And I mean, I try to be flexible about this. I don't like being late. And I'm willing to grant that, you know, if you live in Los Angeles, there's a lot of traffic or... But yeah, I hold myself generally...

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Nakta Alaghebandan

To the punctual standard.

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Tyler Finn

To the punctual standard, yes. And I can still think of a few moments in my career where I was late to something and I lost an opportunity as a result of it or... And I'm not about being one minute late to to a zoom call or something like that, right? I mean we can all give ourselves a little bit of flexibility in this life But yeah, I like to be I like to be five minutes early. You heard it here

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Nakta Alaghebandan

What is a book you would like to recommend to your listeners? And you can recommend more than one, I'm sure that's a hard one to narrow down.

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Tyler Finn

I thought a bit about this question because I knew it was coming.

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Nakta Alaghebandan

Makes sense.

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Tyler Finn

I'll recommend a business book first. I have three books that I think will be all different and interesting for folks to read. The first book is a business-y book. It's called Give and Take. It's by Adam Grant. I may have mentioned it in conversation with other podcast guests. He looks at the sort of... He's a psychologist, like kind of a pop psychologist, but he's very smart. He looks at the sort of landscape and categorizes people in three ways. He says, there are people who are givers, they're willing to give without any notion of reciprocity or getting something in return. There are matchers, people who are totally willing to give, but it's more like, I bought coffee this time, so I'm not gonna tell you to buy coffee next time, but you should probably buy me coffee next time.

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Nakta Alaghebandan

There's an expectation.

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Tyler Finn

There's an expectation. And then there's takers, people who don't give very, I mean, we all know, hopefully we don't have many people like this in our lives. We've probably all dealt with people like this before. We've encountered them before.

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Tyler Finn

People who just take, take, take, take, take are very sort of self-interested. And it's been a number of years since I read the book, so I'm not going to be able to explain the sort of whole argument and all the research. But essentially, he's looking at like, we know we probably don't want to be takers, right? But are givers just chumps? Are we all being taken advantage of? The conclusion in the research over the long run is the answer is no. Actually true givers are the ones who end up with the most and who are the happiest and who actually oftentimes have the most money. If you're listening and you've read this book in the past week, you can probably poke holes in that summary, but I like carrying that with me in my own life and I would recommend that folks read it. I don't read a lot of fiction. A friend and mentor of mine recommended a book that I read recently called The Last Days of Night. It's a very quick read. It's historical fiction. It's about Thomas Edison and George Westinghouse and their sort of fight to electrify America. And the interesting thing, yeah, the interesting thing for lawyers, the folks who are listening are interested in the law, is that Paul Cravath, who started the firm now Cravath, Swain & Moore, features very prominently because he was George Westinghouse's lawyer and there's an IP sort of fight battle occurring. I think it's a fun read and something that's a little legal related for our listeners. It was tough for me to pick a non-fiction book to recommend for the audience. One that I… I mean, I subscribed to The New Yorker, I like long-form journalism, I like that sort of journalistic style. Everyone who is here is gone is about the sort of immigration crisis in America. I think that's a very important component of this political moment and what we're dealing with. And it's something that I didn't understand as deeply perhaps as some of the economic drivers or changes in Washington and Washingtonian norms that have happened. I read it before the election last year and if you want to understand this political moment, I would highly recommend that you read it as well.

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Nakta Alaghebandan

Awesome. That's a very well-rounded list of book recommendations. I'm going to queue all of those up later, too. Last question. Looking back on the early days of your career, what is one thing you know now that you wish you'd known back then?

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Tyler Finn

This is a high-pressure question for me because I've heard a lot of different answers. And there's an obvious answer that I think that we've covered, which is that there's like no one right path and things wind in ways that are unexpected. But for me, it's actually something different. I wish that I had known that I shouldn't be prioritizing or thinking so much about success or momentum. I mean those things are all important but I wish that I'd spent more time and I try to do this today thinking about how I can live with some grace. Right? Like grace from my co-workers, grace from myself, grace for those around me. Life ends up being a lot harder, I think, than most people would anticipate when they're like 22 or 23. And so my advice to my younger self would be pretty simple, actually. It's like try to live with the most grace that you can each and every day.

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Nakta Alaghebandan

Yeah, don't sweat the small stuff.

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Tyler Finn

And don't sweat the small stuff.

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Nakta Alaghebandan

Tyler, it has been such a pleasure turning the tables. You obviously make a very great guest on your own show too. And I just think what you've built with the abstract is so wonderful. You've created the space where people can reflect on their unique journeys and they can do it with humor and insight and honesty. And it also lands in a way where the listeners can really pull from that wisdom and apply it to whatever unique place they are in their own careers. I mean, I'm one of those people. Episode four with Akshay was the reason I reached out to him and ended up joining SpotDraft. So I'm very grateful to you.

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Tyler Finn

That’s great, I didn’t know that.

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Nakta Alaghebandan

Yeah, fun little fact. I am so excited that we got to spotlight your story and I'm excited for the next 100. and I'm excited for the next 100.

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Tyler Finn

Thanks for doing this with me.

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