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Ep 100: Community as Strategy: Your Guide to Growth with Tyler Finn
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In the 100th episode of The Abstract, the mic flips as SpotDraft’s Chief of Staff, Nakta Alaghebandan, interviews our podcast’s usual host and creator, Tyler Finn.
From his start in public policy to shaping one of the most influential legal communities at SpotDraft, Tyler shares the pivotal career moments, risky leaps, and trust-building lessons that defined his path. He reflects on navigating early career detours, becoming a privacy leader despite skepticism, and building trust from scratch with executive stakeholders and customers.
The conversation dives deep into community-building philosophy, the value of calculated risk, and how Tyler sees “increasing your surface area” as the most underutilized career growth strategy. You'll also hear how the podcast came to life, what he’s learned after 100 episodes, and his advice for creating lasting impact — with humility, humour, and heart.
Read detailed summary: https://www.spotdraft.com/podcast/episode-100
Topics
Introduction: 0:00
Tyler’s early pivot from public policy to legal tech: 3:15
Choosing privacy despite warnings against it: 5:40
Building trust after entering a low-trust role: 8:33
Becoming the go-to for high-anxiety customer: 12:04
Why cross-functional thinking matters in legal leadership: 15:52
Sitting in the grey: layoffs, uncertainty, and consulting: 19:03
Taking calculated risks and trusting your gut: 22:51
From outsider to community leader at TechGC: 25:20
What real community building looks like: 29:28
How to design a community where people actually open up: 30:55
Building trust and reputation intentionally: 31:25
How SpotDraft went from a consulting client to employer: 36:26
Community as a future-facing marketing strategy: 40:18
How Tyler now evaluates executive teams and companies: 43:22
Why the CEO and executive team matter more than you think: 46:33
What great executive teams do to support internal community: 47:42
Why Tyler launched The Abstract and his goals for it: 50:12
Personal lessons from 100 episodes: 56:04
“Increasing your surface area” and embracing uncertainty: 1:01:56
Favourite part of the day: 1:05:12
Professional pet peeve: 1:06:11
Book recommendations: 1:07:09
Advice to younger self: 1:11:21
Connect with us:
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
Nakta Alaghebandan - https://www.linkedin.com/in/nakta/
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.
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Transcript
Tyler Finn's Career Pivot
00:00:00
Speaker
Tyler Finn, welcome to your own show. It feels a little weird to be on this side of the mic. I guess I'm getting a a taste of my own medicine. i figured we could just start from the very beginning. I thought I was going to like be in DC and then maybe go to law school and then be like a prosecutor or something. And like clearly that is not the path that I've had. I want to talk about the abstract, so i want to get a little meta. Yeah.
00:00:23
Speaker
I want to know why did you start the podcast? It was not my idea. okay. Yeah, I will not take credit for this. Go on.
Expanding GC Roles
00:00:32
Speaker
It was Rohith who runs product and had been running marketing at the time. Tyler, we just hired you.
00:00:40
Speaker
You don't seem to have a full plate yet. Do this. What advice would
Impact of Podcasting on Tyler
00:00:44
Speaker
you have for listeners? 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? Right.
00:01:00
Speaker
People think of themselves as as operators, as leaders in the business. You've now interviewed almost 100 guests.
Building Trust and Reputation
00:01:07
Speaker
um How have those conversations from the show changed how you show up in your own work? I've never asked them this question, but I bet if you asked them, would you consider yourself to be an extraordinary person?
00:01:22
Speaker
I think most of them would probably say...
00:01:31
Speaker
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?
Diverse Career Path of Tyler Finn
00:01:44
Speaker
Welcome to a very special 100th episode of The Abstract. I'm Nocta Algabandon, and I'm Chief of Staff to Spot Draft's COO, Akshay Verma. who longtime listeners may recall from earlier episodes on the show.
00:01:59
Speaker
Today, I'm joined by a very special guest, ah somebody who is usually on this side of the mic, Tyler Finn. Tyler is Spot Draft's head of community and growth, and of course, the host and creator of The Abstract.
00:02:14
Speaker
um 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.
Navigating Career Transitions
00:02:27
Speaker
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.
00:02:45
Speaker
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.
00:02:58
Speaker
It feels a little weird to be on this side of the mic. I guess I'm getting a a taste of my own medicine. um But i'm going to take some solace in the fact that you're probably a much nicer interviewer than I am. will go easy on you. You'll go easy on me. Yes. Thank you for letting me steal the mic.
00:03:14
Speaker
um I figured we could just start from the very
Entering the Privacy Field
00:03:17
Speaker
beginning. Yeah. um You originally thought that you were going to go into public policy and move to D.C. and obviously there was a pivot there. So can you walk us through that?
00:03:28
Speaker
For sure. um When I started my career, or when I graduated from college, I had a plan around going to D.C. I thought, you know, Hillary Clinton is going to be president.
00:03:40
Speaker
I'd spend some time in D.C. 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. um and i think i think a lot of folks.
00:03:53
Speaker
um I ended up thinking, OK, now I've got to pivot. I'm going go and and work on the hill in some way, shape or form. And i think, you know, I had the lesson very early on that your network and and who you know um is is almost as important or just as important as your resume. And um i was I had people who were advocating for me in D.C. who were going to help me find a job.
00:04:19
Speaker
um 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.
00:04:36
Speaker
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 um with Congress and the FAA.
00:04:50
Speaker
ah And i mean, on the one hand, you know, staff assistant salaries are not that high in DC. They're like 25, $28,000 a year. yeah You spend most of your time answering the phone and if you get lucky, responding to constituent mail.
00:05:05
Speaker
um So this sounded pretty good, right? Going and working for a private company and it was in Santa
Building Trust in a Company
00:05:11
Speaker
Monica. So it was like doing the policy by the beach, not doing policy in the swamp. like And yeah, i I decided, hey, you know,
00:05:20
Speaker
I'll be qualified in a year to go answer phones in D.C. 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. um i should I should go for it and try it. And then one thing led to another. And I ended up spending, you know, most of my 20s living in in l L.A. doing various sort of legal and and policy things.
00:05:40
Speaker
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.
00:05:52
Speaker
So what made you trust your instincts and pursue it anyway? Yeah, so I'd been with ah 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 I look for now that maybe I didn't look for back then when I'm joining ah joining a company or evaluating an executive team.
00:06:14
Speaker
um But ah i had, and again, another friend who introduced me to ceo of a data company that was looking for a a policy and privacy person. and And I knew nothing about privacy.
00:06:30
Speaker
um And I had a lot of people, as you said, who were warning me like,
Community Building with TechGC
00:06:34
Speaker
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.
00:06:48
Speaker
And it's very process oriented and procedural. And it's not going to be that interesting. um And I think I looked at kind of the 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.
00:07:04
Speaker
um 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, okay, that there's opportunity for growth here. There's opportunity to make this into more than just a How do I comply with this one little law?
00:07:22
Speaker
Maybe if 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. um i also i i trusted the folks who were hiring me. i was getting hired at the time by the COO and the the CFO at the business um who were sort of jointly going to run privacy from a product perspective and from a compliance legal perspective.
00:07:50
Speaker
I trusted them when they said there's going to be a lot of growth opportunity here for you and um this isn't going to be boring. Don't worry. Right. And I think it really worked out for me.
00:08:04
Speaker
um i think if you're interviewing for a job and 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.
00:08:14
Speaker
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, um that's a great sign and something that that I would look for and something that I would lean into or i have leaned into again and again.
00:08:32
Speaker
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?
00:08:51
Speaker
Oh, that's a good question. and you You clearly did your research here. ah So, you know, when I entered that business, and this is this is not going to be, I think, dissimilar to the situation that the situations that lots of our listeners have dealt with before. Yeah.
00:09:08
Speaker
you know there'd there'd been a lawyer in the role before for a short period of time who um we'll call it it maybe alienated some key stakeholders in the business with a a slightly more risk averse approach to privacy and compliance um so when i stepped in i was almost walking on eggshells a little bit right it's it's it's like okay the The product managers, they really 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. They're projecting that trauma onto this new person that was in that old role. Correct. And did all wrong. Yeah.
00:09:54
Speaker
And so, i mean, I think there's 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?
00:10:14
Speaker
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. um Again, not unusual to our listeners, but I think a no, but or a yes, is.
00:10:30
Speaker
and is always better than just a flat no, right? ah if If someone's come to you and said, hey, we really want to build out this new feature ah using this new type of data that we're going to 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.
00:10:54
Speaker
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 collaboratively with them. um Because ultimately, at the end of the day, if you're in a business, right like the the long-term goal is to build great products or offer amazing services.
00:11:15
Speaker
grow the business, grow the business in the right way over the the long run. um And so I approach this very much from the perspective of I need to understand everything I can about my job, the privacy world.
00:11:30
Speaker
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.
00:11:41
Speaker
um And if I can do that and then present my ideas or present my pushback in the right way, ah 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. Completely. And I feel like the right...
00:12:06
Speaker
um high trust approach to collaborating with anybody is always defaulting to being a high context person. um You want to explain why you're doing things instead of just ah expecting people to buy into why they should follow your lead. So that's definitely um 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 did you go from maybe a trust deficit to being the trusted um calmer of anxiety amongst customers?
00:12:50
Speaker
I mean, I think there's two steps. I mean, I think one, um 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.
00:13:13
Speaker
um 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 like 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 and not only going to be um 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 maybe when um when a deal gets slightly changed and then everyone goes to meet with the ah CRO or the chief business officer to talk about why the deal is going to be changed slightly based on your advice.
00:13:56
Speaker
yeah 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.
00:14:08
Speaker
um So building that trust is important. ah I have like one story that I think is is good here. um You know, one of the one of the guys that I worked with and for, I guess, in a sense, so our CRO, um who's gone on to be the the CEO of a company in like the music data space. Really interesting guy tall, kind of laconic, serious British man, likes to go on like 50, 100 mile bike rides on the weekends. Right.
00:14:37
Speaker
um He was not known for being effusive in his praise, let's say, like loyal and dedicated to his team and an amazing manager, and a great executive, but not exactly like effusive in his praise.
00:14:50
Speaker
And ah when we would do sort of major policy changes, update a privacy policy, um i liked to send out an all company email about this sort of thing. I thought, you know, internal communication was really important around these topics.
00:15:06
Speaker
um And I sent one of those out and he responded to it within like 15 minutes or so. and it was very simple. He said like, this is very important work and everyone should pay attention to this.
00:15:20
Speaker
Regards, Rob. Regards. Or whatever he said. Best. Rob. ah And you know very Rob, like very short, very to the point. Right.
00:15:31
Speaker
I guarantee you that the sales team suddenly went back and reread that email all the way through. um 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 to do jobs like this.
00:15:50
Speaker
um Yeah. Right. you can't yeah um you need 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 and 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
00:16:21
Speaker
What makes that intersection meaningful for you? Yeah, and I go back. I mean, I'll answer you this sort of second part of your question about like, how do you get put in high stress or situations with difficult customers? hours or answer I'll answer that along with this one. I mean, i think that um I have always, after you figure out the foundation, right?
00:16:41
Speaker
after you 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 affected by? Like understand some of those basics.
00:16:53
Speaker
then you want to see the whole picture, right? so you start to ask other questions like, ah who are our allies in the ecosystem that we're operating in? Who might our detractors be or our competitors?
00:17:06
Speaker
Why are they doing what they're doing? Not just like, this competitor is doing you know 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 um when you start to see the whole picture ah i think you get given more ambiguous projects, projects that other people might not be able to solve.
00:17:39
Speaker
um you You show but you're thinking about things from a very cross-functional perspective. ah And I mean, ultimately, these days, that's what really great executives are.
00:17:55
Speaker
And I think we've seen a bit of an evolution there. I mean I've been able to watch for the past you know five to 10 years the sort of like GC role evolve in some ways.
00:18:06
Speaker
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? Right?
00:18:21
Speaker
people think of themselves as 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.
00:18:32
Speaker
And so, you know, 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.
00:19:01
Speaker
um That's how you level up. Yeah, you want to make those connections um that you might usually find in a different domain. how How does that have an interesting impact in a different area? And so i I personally, as my experience in the chief of Saffril for quite some time, I believe that the magic really does happen in the gray areas.
00:19:23
Speaker
Yes. um not just within a work context, of course. And i know, we 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.
00:19:43
Speaker
what What was your mindset in those moments of sitting in the gray area and you know experiencing that uncertainty? Yeah. Can I say one more thing on the last question? Of course.
00:19:53
Speaker
ah I think the other thing about figuring out that cross-functional picture or figuring out that bigger picture is that it does take time. Yeah. um And I don't think there's anything wrong with people who have, you know, these days.
00:20:09
Speaker
I 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. i But I think figuring out the bigger picture 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. People probably shouldn't stick around companies for 15 years so much, at least in the space that we're operating in. Unless the company is totally evolving into a whole different piece. Or maybe you keep getting promoted and now you're the CEO. or right um
00:20:50
Speaker
But I do think it takes time. right And there's nothing wrong with showing up in a business and saying, I'm going to get this one thing done and I'm gonna i'm going to do a great job and going to leave in 18 months and that's fine and I'm on to the next thing. like that's That's totally cool.
00:21:04
Speaker
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 going to be able to draw the the connections. Yeah. And you can't.
00:21:19
Speaker
yet You can't upload judgment into your brain. It takes time to cultivate that. Totally. um Yeah, I think a lot about judgment. We can talk about that. Yeah, definitely.
00:21:30
Speaker
Yeah, I mean, navigating like ambiguity or uncertainty, um I've had to do a lot more of that than I ever would have anticipated in my career. I mean, yeah i used I thought I was going to like be in D.C. and then maybe go to law school and then be like a prosecutor or something. And like clearly, that is not path that I've had.
00:21:49
Speaker
ah And I think that you can become affirmatively more comfortable with uncertainty and ambiguity. you can learn to lean into it.
00:22:00
Speaker
You can modulate your w risk tolerance over time. um Part of that, I think, is also how much risk you're willing to incur and in other areas of your life or the practice that you create around that. Right.
00:22:14
Speaker
I'm going sign up for doesn't have to be physical, but I'm going to sign up for this long race and I don't know if I can do it. And I'm kind of scared about that. You know, if you go through experiences where you're scared ah outside of the workplace, to be scared.
00:22:27
Speaker
I think that you can you can draw on those when they show up. um And, you know, it's like I made it through this 50K trail race sort of thing. ah i just got laid off.
00:22:41
Speaker
I know this is going to 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 to to push push through it. I mean, we also...
00:22:52
Speaker
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.
00:23:05
Speaker
yeah um What advice would you have for listeners on how to um hone that skill of taking calculated risks? Obviously, There's a lot of known unknowns and also unknown unknowns, but yeah how do you get comfortable with your um with trusting yourself in those gray areas?
00:23:23
Speaker
I mean, usually if you're trying to make a decision, um the risk comes from a lack of perfect information. yeah right So you're always trying to strive for more and better information.
00:23:35
Speaker
ah i I think it's important to trust your gut, um 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 ah 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?
00:24:08
Speaker
Go to the, if you're considering a new job and it's not going to 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 the new part of the ecosystem that you're you're thinking about moving into.
00:24:27
Speaker
um They're going to help you see whether this is really risky or or not. i think I think people sometimes tend over-index on the risk that they see um when really what they need is sort of better information or a broader perspective.
00:24:49
Speaker
Yeah, calibration yeah also. um Let's talk about... sometimes people will also back you off. yeah I've had that too. Yeah, i walk they'll walk you off. They'll walk you back, which is not to say that you should always lean into, you know, someone comes along and ah and offers you something that sounds really amazing and you're like oh, maybe I should... 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 going to work out or it's going to totally blow up your career or... But like sit back and think for a second and pause for a second, right? Yeah. um yeah and so you told me a really funny story i really want to 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 um i want to talk about tech gc 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
00:25:49
Speaker
Yeah, my um this is the first you see you hired me after college. I have a lot to thank him for. He's a friend of mine, Bill Goodwin. ah If you've ever met Bill, you know that he he wears ah Hawaiian shirts, rain spooners every day, tucked into khakis.
00:26:08
Speaker
So he's got Sperry's on. I maybe I've seen him in a tie once. ah 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 L.A.
00:26:30
Speaker
um you know At the time, I thought I might want to 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.
00:26:42
Speaker
and And I did. Kieran and I, Kieran 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 so turned it into a really amazing, not just community, but really amazing business. um Kieran and i started to talk to each other, get to know each other a little bit.
00:27:06
Speaker
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... um Maybe Chris was working with them, doing some marketing stuff, and then like a couple of Columbia Law students, ah basically. And i basically raised my hand. I said, look, I'm on the West Coast. You're all in New York.
00:27:30
Speaker
You want to be doing more events here and doing dinners in San Francisco and Seattle and l a and... You probably don't want to hop on that transcon flight like every single week or every other week. valid And one thing goes, you know, turns into another and you start to do good work and um ran the list, moderated the listserv for many years, like sitting there approving emails all day on my phone quietly.
00:27:56
Speaker
i organized a lot of their webinars. I hosted a lot of their West Coast dinners. um If you do good work, you know, that that the great thing about doing good work, I think, and the ah the sort of like tragedy of doing good work is people start to give you more. yeah ah So, you know, there were there were especially during COVID um when our when the GC community, this sort of our population was was dealing with like How do we you know get people out of our offices? What do they need as they start to work from home?
00:28:31
Speaker
How do we deal with i 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 2 in the morning most days helping organize these sorts of things. um But you know I would not be here today in in in any capacity like I am. um yeah Without that sort of experience, without getting to know that community, without all that I learned from the way that really Kieran and Greg set a strong ethos and built that community in, I think, a very intentional and particular way.
00:29:09
Speaker
Totally. I was just going to say it sounds like that dinner was a very fateful pivot into your community. Yes. Chapter and this facet of your being. And you've said, of course, that TechGC, all those experiences really shaped your philosophy on community. So yeah what what lessons from that time really still guide you today?
00:29:34
Speaker
The members of a community have to be front and center. um you know Greg these days will 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.
00:29:57
Speaker
um 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.
00:30:10
Speaker
um It was all about the members. It was not about Kieran and Greg. ah And that flowed down into really what this is about is peer to peer interaction, peer to peer learning.
00:30:24
Speaker
And so, yeah i mean, we will bring in sponsors, whether they're law firms or folks like Spot Drafts, you know, legal tech providers, um other sort of privacy tech vendors, insurance brokers, et cetera. we'll We'll bring those folks in ah when they have an important perspective to share.
00:30:43
Speaker
ah or if they have something to bring to the table, but not just to fund the dinner and walk away, right? um Because really what it needs to be about is sort of peer-to-peer connection and peer-to-peer learning.
00:30:57
Speaker
ah And they've always taken, and I mean this i think dovetails a lot with things that I've worked on in my career, and they've always taken a very long-term view of of growth.
00:31:08
Speaker
They would rather grow something slowly and intentionally in a way that builds trust and builds sort of like real sticky, cohesive connection than grow something very quickly that then flames out. Yeah, organic, not GMO community. I think that the best type of community is the one where... I love that term of phrase. Did you just make that up? Yeah, just came up with it. I feel like the right approach to building a community is exactly like you say.
00:31:40
Speaker
the 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. um what What else do you think really makes a community work?
00:31:54
Speaker
People have to be willing to share. i mean, that goes back to the trust piece. um You know, I mean, go to happy hour, meet a few new people. I mean, that's a good thing, too. Right.
00:32:06
Speaker
um 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.
00:32:24
Speaker
a need for help on some particular task or with project or for a firm recommendation or people feel a willingness to share, that's a great sign of a healthy community.
00:32:40
Speaker
Yeah, and I guess that would 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.
00:33:01
Speaker
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.
00:33:17
Speaker
I want to be I want to be a better question asker than ah but than ah than a good talker. youre enable You want to enable the storytelling. Correct. And so facilitator. Yeah, a facility exactly.
00:33:29
Speaker
And. All of that, I think, also just keeps boiling back down to trust and how also reputation comes from trust, trusting somebody like I don't think it's I mean, a good reputation, at least is associated with trust. And i i I think and tell me if you agree, these sound like two of your big north stars.
00:33:50
Speaker
Yes. If we can pick two north stars. um how 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. um how How do you do that with just these really intangible but super important qualities?
00:34:20
Speaker
I mean, there's tactical things that you can do, right? um 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 and top notch and and interesting. um You have to make small decisions about if we're going to host a spot draft dinner, are we going to have a spot draft, like standee roll up thing at the dinner? Probably not, right? You know, like that's not the sort of thing that's going to engender long term trust.
00:34:48
Speaker
Who you let into the sort of community or the the way you approach that I think is also a very important decision that should not be taken lightly because it's going to change the sort of tone and tenor of the ah interaction between members. so um But I think a sort of broader view, whether it's community or a company that you're building, any organization,
00:35:10
Speaker
um 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.
00:35:24
Speaker
um
00:35:27
Speaker
Focusing on trust and reputation, meaning do the stakeholders that care about us trust us?
00:35:38
Speaker
Do we have a strong reputation with them? Are they going to support us? i I really think that's one of the only ways that you build a long-term, durable business.
00:35:53
Speaker
Mm-hmm. 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 and it's not built for the long run. Yeah, not stable.
00:36:07
Speaker
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.
00:36:19
Speaker
And how how can anything be long term when you're on unstable footing? um And so going back to your consulting era, which is also all about building trust, like how 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, yeah to speak. So Spot Draft, interestingly enough, came on your radar as a consulting client. So how did that happen and how did that turn into you now joining Draft's team full time? Yeah. i Quite a journey. Yes.
00:36:59
Speaker
And it wasn't how I expected to play out either, by the way. It never is. Which I think is a good thing. Spot Draft was sponsoring TechGC events. I started to see Spot Draft at more events.
00:37:11
Speaker
I met Shashank and got to know him a little bit. Vic, who used to be on our team here in in New York, now has gone back in-house ah to to legal roles.
00:37:23
Speaker
Rohith, chief product officer. um Started to get to know them a bit. And I think at the time spot Draft was was dealing with um not a product market fit issue, um not really a growth challenge, um more of a ah messaging refinement problem, right? which was We're coming to and trying to grow in the North American market.
00:37:50
Speaker
ah We want to make sure that the way that we're speaking to the market is really resonating. ah We need to have a stronger back and forth with the market or the community or the sort of ecosystem here.
00:38:03
Speaker
um so that way we're refining the way that we're talking about our product offering, the way that we're engaging the market. um And in getting to know those folks, it seemed like they could use a little bit of help.
00:38:17
Speaker
Like not like a lot of help, but a little bit of help. tell us more ah And so I took on a a sort of like, you know, short sort of term consulting arrangement. Our CEO, Shashank,
00:38:29
Speaker
Basically use 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 consultant so you don't take another full time job until you take the one that I'm offering you?
00:38:45
Speaker
um In many ways, I i would actually i would I would look at this a little bit differently maybe than I 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 Spot Draft team. I got to work with them on some projects.
00:39:01
Speaker
I got to see how I interacted with other people in the marketing or before I joined the company. Look, I understand that people don't love like ah we're going to give you a six month provisional period in which you're a contract.
00:39:14
Speaker
That feels a lot more like ah we are evaluating you yeah and whether or not we want to keep you. And that that feels a little bit different than than this did. um But I advise i mean, I talk to a lot of folks who are between jobs, whether they're general counsels,
00:39:32
Speaker
commercial lawyers, privacy lawyers or privacy managers, legal operations professionals. I advise a lot of them to stand up a consultancy.
00:39:43
Speaker
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. ah Two or three clients is and it may not be plenty for the long run for you, but it's plenty.
00:40:03
Speaker
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 um that's what happened with me. And ah yeah, the rest is history. And so then you got to bring all the wonderful philosophies and learnings from TechGC into this role.
00:40:26
Speaker
But then how has your perspective on community building over the last three years since you've joined Spot Draft changed? so i've had to so 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 that i did not before um i've had to think about community as a ah counterpart to marketing in a way that i was not thinking and about it before i mean i think in many ways actually um
00:41:01
Speaker
Community is I wouldn't a community is not the future of marketing. Community is a lot of what marketing I think is becoming or needs to become. Right. Nobody's just storytelling, especially in a B2B business like we have in which these are, you know,
00:41:16
Speaker
ah very sophisticated buyers. um 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. um You know, the unwinding a wrong decision is also painful. um they're very sophisticated buyers.
00:41:41
Speaker
They're not generally going to pick up the phone and and answer, you know, from a like very, very junior sort of BDR sales rep, right? there They're going to want to, when they go out to evaluate a product offering, they're going to want to know your reputation in the market and think that you have a good brand, um probably have seen you in various places as ah as a bit of a thought leader. um 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? right.
00:42:15
Speaker
um So I think about community differently in that way as well. um Would you agree that it's this extension of marketing? It's marketing through empathy and trust building and storytelling?
00:42:29
Speaker
Yeah, and that's a good way to put it. Yeah. i think um i think the only 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.
00:42:50
Speaker
is I think that from time to time, community should serve as a slight counterweight or or counterbalance to some of what marketing or some of what sales might want to do.
00:43:03
Speaker
I think it's helpful to have someone in the business who's thinking with trust as their sort of like core lens as opposed to demand generation or as opposed to revenue and ARR, right?
00:43:16
Speaker
Yeah.
00:43:19
Speaker
that's going to give you a longer term perspective. Yeah. One more question on you know your experience you know coming into a company setting. And you've said that your priorities and how you evaluate companies have changed, at least like within the context of your career path.
00:43:36
Speaker
What do you care most about now that you might not have considered earlier in your career? Well, 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 close.
00:43:56
Speaker
That would not have been, mean, Shashank would have never done that, but that would not have been the right 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 going to be? Am I going to be set up for success in my role?
00:44:10
Speaker
um I think that one thing that I prioritize a lot more now um that i than I used to the CEO is. worked for six years.
00:44:23
Speaker
um i've worked for set Or seven, six, I think. i mean, i haven't I haven't had the longest career, but six different CEOs at these companies.
00:44:35
Speaker
um I've been through CEO transitions three times. Wow. You've a lot of leadership styles. Correct. Yeah. ah And there are and and by the way, CEOs and executives are people, too. So that's no one should be expected to be perfect or the perfect leader. Some people are better at motivating their teams to accomplish incredible things.
00:45:02
Speaker
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.
00:45:21
Speaker
And maybe sometimes those traits thrive at different stages of the company. Correct. A wartime CEO. I mean, I don't love the wartime metaphor, actually, but like the wartime CEO is maybe different than CEO that you want when the company is doing really well and has a seven billion dollar market cap in the public markets and growth is perfect and like 15 percent or 20 percent year over year. Right. I mean, different different styles might be required in those situations.
00:45:51
Speaker
um But one observation would 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.
00:46:15
Speaker
um So i I try to do a lot more evaluation of what's the CEO and what's the executive team, even if I'm not joining that team, right? Who am I joining?
00:46:26
Speaker
Who are they going to be? And then also sort of like, who are the people who I'm going to be working with? 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?
00:46:44
Speaker
Yes, absolutely. I think super key, especially for helping make up for one another's efficient. I mean, that's why you have a C-suite, right? Like you're not going to be good at every single thing um at every single moment. And if an executive team isn't communicating well together, ah 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. yeah ah If the executive team isn't, I like this term, I know Akshay likes this term, the sort of like we need to like disagree and then commit, right? yeah We're going to hash this out around the table.
00:47:19
Speaker
Ultimately, we've decided that one person or we are going to make a decision. We are going to pick this path. We are going to run together. 100% at what we've decided. We're not going to like let you kind of like drag your feet over here to slow us down to maybe get what you want. right um 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. What's something you wish you saw executive teams, C-suites do more of from through that community lens? Yeah.
00:47:54
Speaker
Well, I think think it's talk to each other. it is that simple. And then i think it's I think it's talk to the company. um I think that
00:48:10
Speaker
if you leave things unsaid in an organization, ah if you don't affirmatively communicate with folks, it's not going to be this like quiet void and everybody keeps going about their day to day. People are going to fill in the blanks.
00:48:28
Speaker
Correct. And that's going to be way harder to rope in. was going to say, assume the worst. Or that, yeah. 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 ah taking the high context approach.
00:48:47
Speaker
Mm-hmm. From the get-go. This requires intention, I think, because executives especially, we are very busy people, yeah right? Being pulled in a lot of different directions.
00:48:58
Speaker
um You have to be very intentional about the way that you communicate with your business and and with your people. And mean, if if we go back to the sort of like small lens of doing privacy work, you know, you want to roll out a company-wide policy.
00:49:13
Speaker
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. I mean, 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 going to be coming out. And then people need to think more. mean, this people need to think more like marketers. That's not the end of that list. by the way but i'm not going to talk for like five minutes about right um people need to think more like marketers i think and executives need to think more like marketers and storytellers yes 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
00:50:07
Speaker
Let's talk about the headspace and the time. Yeah. yeah right i have you To be allowed to do this. yeah Exactly. And so I want to talk about the abstract. So i want to get a little meta. Yeah. 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 and how did you pitch it to the team?
00:50:28
Speaker
It was not my idea. Yeah, I will not take credit for this. It was Rohith who was ah ran runs product and and would had been running marketing at the time. And I think, you know, he kind of he looked out at other companies and he's like, lots of other companies have podcasts. We should have a podcast.
00:50:46
Speaker
Tyler, we just hired you. You don't seem to have a full plate yet. Do this. ah And so then it was incumbent upon me to run with it and, you know, 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, ah I knew I wanted to do something around.
00:51:12
Speaker
well i knew we needed to encompass. all that legal is, right? I did not want to do something that was just like, I'm only going to interview GCs or CLO. That felt very narrow.
00:51:24
Speaker
um I wanted it to be about professional development in some important way and and personal development. I wanted people to tell stories.
00:51:37
Speaker
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. yeah um That also felt too like CLE boring narrow.
00:51:54
Speaker
ah And so I think what we've landed on over time and hopefully, I mean, I've gotten The title is starting to make more sense. sense. Yeah, exactly. The abstract, right? yeah um What we've landed on over time is we want to have folks who are in legal or legal adjacent roles, who are legal professionals broadly.
00:52:13
Speaker
They might be GCs or CLOs. They might be 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 they're a consultant. Akshay to say, a recovering...
00:52:30
Speaker
A recovering lawyer. I i like to talk to them about their career paths, um success that they've had, real trials they've been through, personal experiences that they're willing to share.
00:52:48
Speaker
i think, you know, the idea is one, there's no one thing. right and this is self-serving we've been talking about my career path today but you know 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 that's That's great. We love that. Right. um
00:53:20
Speaker
That's not the typical profile or persona that I'm i'm looking for when i when I bring guests on. um 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.
00:53:39
Speaker
um I also think over time, I've built, as I've gotten probably better at interviewing, but also as I've built more um trust with um my audience and also with my guests, right? um Credibility with future guests.
00:53:59
Speaker
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 could be like dan haley who has had testicular cancer twice and has been through two ceo changes that were totally unexpected um you know One where hedge fund came in and ousted his CEO and one where she had a massive stroke. and Or like a Marc Maron who woke up and he was the GC of Barstool Sports and the CEO of Barstool Sports tweeted overnight, my lawyer is an idiot. And he wakes up to like 15,000 notifications.
00:54:44
Speaker
don't want to have those conversations because...
00:54:47
Speaker
i don't have i don't want to have those conversations because um they sound... Sensational. Sensational. That's the word that I'm searching for. um 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 and um
00:55:18
Speaker
how they've been through something like that and come out the other side. i i love what this type of storytelling format enables because I don't know, i feel like especially over the last 20 years, if 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.
00:55:40
Speaker
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 and how much more...
00:55:58
Speaker
interesting and insightful what you might have to offer to others can be. And so you've now interviewed almost 100 guests. um How have those conversations from the show changed how you show up in your own work?
00:56:14
Speaker
That's a good question. um 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 that is right.
00:56:29
Speaker
um 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 like, you know,
00:56:40
Speaker
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 know, you don't have to be a nihilist, right, and say like none of this matters or...
00:56:57
Speaker
I'm not going to be talking to that boss in 15 years, so I don't care. Right. That's not, and that's not what I'm saying. Saying like, you can get through this, right? Like 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.
00:57:11
Speaker
There's going to be a light on the, on the other side of the tunnel. Um, so I think my guests have borne that out. Um, most of these folks are people managers, uh, a, a, a,
00:57:24
Speaker
common theme or so something that I've heard that I think more about um today than than I used to is not what impact can I individually have on this business or organization or a community.
00:57:41
Speaker
But um how can I create opportunities or support others to empower others or how can I support others um so they can be better at their jobs or they can accomplish things?
00:57:55
Speaker
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.
00:58:14
Speaker
think that's a huge spot draft value too. Like can't work in silos and went winning is about winning together. If someone else is winning, that means we're winning too.
00:58:25
Speaker
This isn't really something that I practice in a day-to-day, um but I think that all of the conversations with my guests, I, i for a long time, this is going to sound very corny.
00:58:40
Speaker
Go on. It's a safe space. ah i I really believe, truly believe that individuals, individual people, can,
00:58:51
Speaker
can ah are capable of extraordinary things and are able to make unexpected impacts on the world around them.
00:59:07
Speaker
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? That's not what I'm saying. um But if you look at 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?
00:59:34
Speaker
I think most of them would probably say, now Well, like that guy MLK was like pretty amazing or, you know, I really loved Barack when he was president or, right?
00:59:49
Speaker
um But you look at let you look at the sum total of of what they've done, the organizations that they've helped run, the thousands of employees lives that they may have changed that markets or communities or that they have built that did not exist before to say nothing of sort of like the you know flapping of the wings and the impact that has made on the rest of the world I mean you don't have to be even like Dana Rao at Adobe to have made a huge impact on the world um
01:00:25
Speaker
Think of Kieran and Greg, right? And and what TechGC has done, you know. um TechGC is good business. It's not a huge business. They're not going to be worth billions of dollars, probably. Maybe Kieran wants to be.
01:00:39
Speaker
um But think of all of the sort of like peer-to-peer connection, education, you know, that that has occurred as a result of what they've built.
01:00:50
Speaker
um So that's a big takeaway for me is you you look at the people on the podcast who've been been here um and...
01:01:01
Speaker
If you're listening to it, you should probably either say, well, you should say, like, maybe I want to be like that someday. And then maybe you should ask yourself, like, maybe I'm a lot closer to that already. Maybe i just want to be more of me and not...
01:01:21
Speaker
you know, tamp it down. Yeah. And that reminds me a lot of something you and I talked about earlier, and it really resonated with me, this belief about um increasing your surface area.
01:01:34
Speaker
Yeah. I love that description because I think a lot of people might be afraid to take up space. Yeah. It might be related to be related to that feeling risky in some way or, you know, scary rejection, all of that.
01:01:52
Speaker
how How can you, um can you explain that concept a little more for the listeners? What do you mean by surface area and and how do you think people should apply it to their own careers and just lives in general? I think Kieran might have used that term. i don't remember exactly, but I think i may have i may be stealing that from him.
01:02:12
Speaker
and um there's There's a couple of ways that I think about that. um you know It's a better way to think about growing your network, right?
01:02:26
Speaker
um Growing your network should not be about, I went from 5,500 LinkedIn followers or connections to 5,750, right?
01:02:37
Speaker
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. um So, i mean, I don't know where my career is going to end up, but I don't think it's going to be by going online and applying to 17 or 170 roles on LinkedIn.
01:03:05
Speaker
I think it's going to be by continuing to increase my surface area. There's another aspect, I'll i'll conflate it with like another concept that um my ah prior boss, very cool guy, um he is the these days um the the CFO of an organization that like does like all these amazing challenges. like They'll raise $100 million dollars to try to you know have a robot go across the desert. That's awesome. Yeah, very cool.
01:03:38
Speaker
um He would always say to me, like, Tyler, remember, knowledge accrues, right? And I, meaning... Very true. You're sitting here and, you know, you're in some product meeting and people are talking, talking, talking, and you're like...
01:03:53
Speaker
well, i'm not really I don't really care about our consumer business. I'm not worried about that. i But knowledge like 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 that tidbit. Right?
01:04:08
Speaker
And so i kind of think about that in in the realm of increasing your surface area or or in the same vein as increasing your surface area as well. Right? Right. I think people or or folks, they, mean, you want to live with intention, right?
01:04:25
Speaker
um But sometimes it's just about sort of absorbing all the world has to offer and seeing where that leads. yeah And so, yeah, it's 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. um It's not about trying to memorize everything about the business.
01:04:49
Speaker
Being a sponge is not passive work. yeah're You're synthesizing, you you're listening, that's active. Yeah. yeah um I prefer i'd prefer not to be described as a sponge. But like the sponge approach. Yes. So, okay, it only feels right to wrap up the conversation with a few fun questions that I think you'll recognize. The Tyler special, if you will.
01:05:11
Speaker
um What is your favorite part of your day to day? If it's not playing tennis or going on a run, um I'm very lucky to get to do lots of context switching.
01:05:25
Speaker
And I've had that as a part of or as as the sort of like the feature of my roles for a long time. um I love that. I love that it you know in one minute I am talking to a GC on a coffee chat that has goal.
01:05:45
Speaker
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.
01:05:56
Speaker
Then I'm like hosting a webinar. Then I'm helping, ah you know, our team with talking points for some interview that our CEO is doing. i love the context switching.
01:06:09
Speaker
um Keeps it fresh. Absolutely. Do you have a professional pet peeve? I do. doesn't? I do. And I mean, i try to be flexible about this.
01:06:22
Speaker
i i don't like being late. um And I'm willing to grant that, you know, if you live in Los Angeles, there's a lot of traffic or. um But yeah, I hold myself generally to the punctual standard, to a punctual, punctual standard. Yes. um And I can still think of a few moments in my career where I was late to something um and ah you know, I lost an opportunity as a result of it or um and I'm not talking 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. um
01:07:04
Speaker
But yeah, I like to be I like to be five minutes early. You heard it here. um What is a book you would like to recommend to your listeners? And You can recommend more than one. I'm sure that that's a hard one to narrow down.
01:07:20
Speaker
thought a bit about this question because I knew it was coming. Makes sense. I'll recommend a business book first. i have I have um three books that I think will be ah all different and and interesting for folks to read.
01:07:37
Speaker
The first book is 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. um He looks at the sort of – he's a psychologist, and like kind of a pop psychologist, but he's very smart. um He looks at the sort of landscape and categorizes people in three ways. He says there are people who give are givers – They're willing to give without any notion of reciprocity or getting something in return.
01:08:11
Speaker
There are matchers, people who are totally willing to give, but it's more like, I bought coffee this time, so I'm not going to tell you to buy coffee next time, but you should probably buy me coffee next time.
01:08:24
Speaker
There's an expectation. There's an expectation. And then there's takers, people who don't give very much. We all know, hopefully, we we don't have many people like this in our lives. We've probably all dealt with people like this before. encountered all them, yeah. Right? We've encountered them before.
01:08:37
Speaker
People who just take take, take, take, take are very sort of self-interested. um 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 like whole argument and all the research.
01:08:48
Speaker
But essentially he's looking at like, ah we know we probably don't want to be takers, right? But are like givers just chumps? Like are we all being taken advantage of? um And the conclusion in the research over the long run is the answer is no.
01:09:03
Speaker
Actually, like true givers the ones who end up with the most and who are the happiest and who actually like oftentimes have the most money. And um if you're listening and you've like read this book in the past week, you can probably poke holes in that summary. But i'm going to I like I like carrying that that with me um in my own life. And I would recommend that folks read it.
01:09:24
Speaker
um I don't read a lot of fiction. A friend and mentor of mine recommended a book ah that I read recently called The Last Days of Night. It's a very quick read. It's it's it's historical fiction.
01:09:40
Speaker
It's about ah Thomas Edison and George Westinghouse and their sort of fight to electrify America. And the interesting thing, yeah, the interesting thing for lawyers, um the folks who are listening or interested in the law, is that Paul Cravath, who you know started the firm now Cravath Swain and Moore, features very prominently because he was George Westinghouse's lawyer. And there's an IP sort of fight battle occurring.
01:10:09
Speaker
um i think that will be i think it's a fun read and like something that's a little legal related yeah yeah for our for our listeners. um It was tough for me to pick like a nonfiction book for ah to recommend for for the audience. um One that I i mean i i like, the I subscribe to The New Yorker. I like long form journalism. um I like that sort of journalistic style.
01:10:36
Speaker
um Everyone who is here is gone, is about the sort of immigration crisis in America. um i think that's a very important component of this political moment and what we're dealing with.
01:10:51
Speaker
And ah 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.
01:11:05
Speaker
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. Awesome. um That's a very um well-rounded list of book recommendations. I'm i'm going to cue all of those up later too.
01:11:19
Speaker
um 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? This is a high pressure question for me yeah because I've heard a lot of different answers.
01:11:34
Speaker
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. um But for me, it's actually something different.
01:11:46
Speaker
It's I wish that I had known that I shouldn't be prioritizing or thinking so much about what success or momentum or I mean those things are all important ah but I wish that I'd spent more time and I try to do this today ah thinking about how I can live with some grace right like grace for my co-workers grace for myself grace for those around me
01:12:18
Speaker
ah And life ends up being a lot harder, i think, ah than than most people would anticipate when they're like 22 or 23. And so my advice to my younger self would be would be pretty simple, actually. It's like try to live with the most grace that you can each and every day.
01:12:38
Speaker
Yeah. Don't sweat the small stuff. And don't sweat the small stuff. Tyler, it has been such a pleasure turning the tables. um You obviously make a very great guest on your own show too.
01:12:50
Speaker
um And so I just think what you've built with the abstract is so wonderful. You've created this space where people can reflect on their unique journeys and they can do it with humor and insight and honesty.
01:13:05
Speaker
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 Spot Draft. So I'm very grateful to you. That's good to hear. I didn't know that. Yeah. Fun little fact. um I am so excited that we got to spotlight your story and I'm excited for the next 100. Thanks for doing this with me.