Operators Ep 22 Transcript
Delian Asparouhov:
Hi, everyone. My name is Delian. I'm a principal at Founders Fund, a venture capital firm based in San Francisco. This is Operators, where I interview non-VC, non-CEO, non-founder operators that make the startup world go round. Today, I'm interviewing Dan Wright, President and COO of at DataRobot. Prior to joining DataRobot, Dan was a COO and before that, General Counsel at AppDynamics. He also spent two and a half years at Goodwin Law Firm as a technology and VC lawyer. I hope you enjoy the show. Cool. Well, Dan, thanks so much for taking the time on the podcast. Excited to chat today.
Dan Wright:
Yeah, thanks for having me.
Delian Asparouhov:
So, before we dive into all the interesting stuff that you're doing at DataRobot, with these types of conversations, I like to actually dive all the way back. You're one of the few, let's say, lawyers in the world of Silicon Valley that's managed to transition from being a lawyer to getting really involved on the business side of things. So, yeah, I guess we'd love to hear why you decided to study law and how you decided to make the transition over from being a VC-focused lawyer to actually transitioning in-house and eventually, obviously, making a pass just to the legal side of in-house staff, but obviously, a much broader set of responsibilities now.
Dan Wright:
Yeah, sounds great. Well, yeah. So, to bring it all the way back, I started to think about going into law around my senior year of college. The thing that was interesting to me about it is it's what underlies every part of our society. I also thought, I just learned some interesting skills that translate into a bunch of different things. So, I decided to go do that. Pretty quickly, though, during my first year of law school, I realized I didn't want to be a courtroom lawyer. I didn't want to be hashing out in litigation and that thing.
The way I realized that is I actually was clerking for one of the most senior judges in the State of Massachusetts. I went to law school at BC. I clerked for this great Mass supreme court justice. Only the most interesting cases get there. So, this is as interesting a career as you could possibly get in that side of the house. I just didn't think it was for me. So, I decided to start thinking about, "All right, well, what can I do that might be within the law but still working with companies to help them navigate things?" That's how I got into VC and startup law.
Delian Asparouhov:
Yeah, interesting cases, I know. Obviously, clerking, at least for the Mass Supreme Court, I'm sure there's at least something that came across that summer, maybe if it wasn't the thing you decided to do long term. Any favorite court cases for that summer?
Dan Wright:
There were some wacky cases. Yeah, I'm trying to remember. It was a while ago. So, I mean, there were always interesting cases with people somehow getting hurt in the most bizarre ways. A lot of times, it wasn't obvious whose fault it was, but you'd have to figure out, "All right, who is legally to blame for this?" So, that was very interesting. The ones that make it up to that level of the court, there oftentimes is not a clear answer. So, you had to figure out, "All right. What is all of the precedent? What's every case that's ever been seen on this one very unique, totally bizarre fact pattern?" And then sometimes extend that out and say, "All right. Well, based on the policy underlying the law, what makes most sense in terms of the outcome?"
Delian Asparouhov:
Yeah, I guess, how did you end up deciding to go over to Goodwin Procter? You stayed there for a little under three years. How'd you come across them? How'd you decide to stay there for that period of time?
Dan Wright:
So, I was pretty sure I wanted to go into the law working with startups and VC firms. I actually got an offer originally from Gunderson Dettmer, which is another Silicon Valley firm. The partner who I was close with ended up leaving and going to Goodwin and starting their West Coast tech practice. So, I decided to follow him. The reason I did that is I figured, it's a mini startup within a law firm. Also, as a result of that, that I'd be able to take on a lot more responsibility early on.
So, from day one, I had hundreds of these companies that I was just managing all the way from just somebody with a deck and idea to large public companies. So, that was great experience, worked like crazy, drink from the fire hose, but learned a lot in a short amount of time and also saw a lot of great companies. It's funny, a lot of the companies that I worked with, the founders that I worked with, I'm still in touch with now. A lot of them have taken those companies public or been acquired. So, it's really cool to see the whole lifecycle over a period of time.
Delian Asparouhov:
And then yeah, I guess, what was the decision making process around it? It sounds like you got to be in a more startup legal environment. You'd obviously made your way over to Silicon Valley. Yeah, I guess how did you go from Gunderson to then joining AppDynamics in a more legal focus role, but obviously, different than what you've been doing up until then given that you are now in-house? What was that process like? Why did you end up making that decision?
Dan Wright:
Yeah, so I was working with lots of different companies, including VCs. I did a bunch of work with Sequoia and some of the other VCs. I had a really good vantage point to say, "All right, I think that this is doing very well. It's in an area where I'm seeing a lot of companies come up. I'm able to see what's happening with their valuation and their growth and what investors are involved. I'm able to get to know the founder." So, this is one that had all of the right signs. It had Greylock and Lightspeed involved from the very beginning. And then I got to know Jyoti, the founder. It was in the space of application performance management.
I could just see how software was exploding and that companies were going to need the ability to monitor and manage all of their apps as that continued to grow. I really thought Jyoti was a special founder. So, he asked me to join and I decided to make the jump. I think that that is one thing, I would say, for anybody who's considering that, lawyers are naturally a little bit risk averse. So, I don't think jumping at the first startup you see is the right approach, but actually, looking at the market and saying, "Hey, was there a real special opportunity with the company and the right market, the right investor base, and a really special founder that you could go work with?" So, that was how I thought about it.
Delian Asparouhov:
Yeah, how did you think about your background in law? When and how it applied to some companies versus others? Were you particularly focused on, "I want to join something in this more enterprise space," or were you considering a wide variety of opportunities? Was it based at all on what you'd studied in law before?
Dan Wright:
Yeah, I mean, I'd studied a lot of law that was applicable more, I thought, to B2B. So, I was looking for something there. I also was looking not just at the type of company, but the stage of company. When I realized that I didn't want to be a partner at a law firm, which was pretty early on, I have lots of friends who do that. That's great, but I just knew it wasn't for me. I was thinking that I wanted to transition into an operating role at some point down the line. So, in my mind, if I could go to a company that I felt pretty confident was going to be successful but if I could get in earlier, I knew that there'd be more opportunity for me to broaden my role over time. So, that was part of how I thought about it as well.
Delian Asparouhov:
So, I guess, speaking of broadening your role, you started off in a very, obviously, legal focused area in AppDynamics and steadily expanded and grew beyond that. I guess, first, what were some of the legal challenges that you were helping with? Is it a lot of contract review and things like that, or what were the primary responsibilities when you first joined? And then how did you even get people comfortable? I feel like a lot of lawyers as they join an operating company for the first time, it's harder to convince the organization to trust you to operate in, let's say, non-legal areas? So, I guess, yeah, how did you build up and navigate that trust? What were the areas that you first expanded to and started to broaden that scope?
Dan Wright:
Yeah, I mean, the funny thing about these large law firms is that everybody specializes, and then there's a group of generalists. So, I was in the generalist group when I was at the law firm. And then you had a specialist to do software licensed contract reviews, right? You had a specialist to do your tax analysis. So, the interesting thing about that is when I joined, I owned all things legal. I had to pick up things like, "How do I negotiate a license agreement?" I remember in my first month, I'm just getting a stack of those and calling lots of friends saying, "How exactly do I do this?" I just had to learn it on the fly.
That was a great experience, but then pretty quickly after that, I said, "Well, where are there other opportunities where there's just something that's important to the company that nobody owns and nobody knows how to do it?" Because there's a lot of things that in a startup people don't know how to do, but somebody needs to do it. I would always be the first one to raise my hand and just say, "Hey, I'll do that." So, it started with things like M&A, running mergers in random countries. We acquired companies in Germany and Switzerland.
So, just raise my hand and say, "I don't know, but I'll figure it out. I'll own the outcome." And then from that, it just expanded to other things and just naturally broadened. I think that's the great thing about a startup company, is that everybody's learning. Most people are stretching themselves all the time. That's a necessity because the company is growing so fast that they have to do that. So, as long as you are willing to take a risk and then be accountable to drive a great outcome, then you'll continue to take on more.
Delian Asparouhov:
I guess, was there already previously general counsel that you end up stepping into, or was there just an unfilled GC seat and you got promoted into that? How did you eventually step into that role? And then obviously, even more importantly than that, eventually, stepping into COO role like this, I think that it's actually relatively rare to see a GC go from GC to COO. I'd say, yeah, you took on just so much that the organization was just naturally, defaulting to coming to you for a variety of things. I mean, it sounds like you started off with M&A, but I imagine, COO's responsibilities are far more broad than that. So, to understand what were the steps between taking on that first, "Hey, who's willing to take this on?", through GC to then COO.
Dan Wright:
Yeah, I mean, so I joined as the first lawyer right around 150 employees. So, that's usually when you'll hire your first lawyer as a startup company. As a result of that, one, I just had to own everything legal. So, that was a pretty easy transition to eventually just be GC. But two, there just wasn't that many people in the company and the company was growing really fast. So, I was able to take on more as a result of that. I think, a lot of the skills that I learned as a lawyer really helped. I was also able to look at other lawyers who've made that transition. It's definitely rare, but it's not unprecedented. There's people like Belinda Johnson at Airbnb. There's other folks that had made that transition.
I think things like the ability to take in massive amounts of data, organize it, and then create plans to go drive things, also to figure out what's important and what's not important, because there's so much coming at you in a startup that you have to understand, "How do I take all these things and prioritize what's actually most important and then align people around that and have everybody focus on that until we drive to a good outcome?" Then there's basic stuff like the ability to communicate well. Those things translate no matter what you do.
Delian Asparouhov:
Yeah, it makes sense. I think, that transition for you happened, I guess, either somewhat right after the timing with the Cisco acquisition. I guess, yeah, what was it like navigating, obviously, that type of... You've done some M&A work. But when the M&A is your own company, I imagine it's a different beast. Any big lessons learned from that transaction that you've carried with you since then regarding the Cisco acquisition of AppDynamics.
Dan Wright:
Yeah, the acquisition itself was pretty crazy, because we were two days from our IPO at the time. So, we had the company ready to go public. We were 100X oversubscribed on the roadshow. We actually had sent people out to New York. So, I remember talking to our CMO at the time on the phone. He was surrounded by a bunch of members of our team and a bunch of bottles of champagne for when we were going to ring the bell. I had to break the news to him that "Hey, we have to pivot and get acquired." So literally, we went from a handshake to a signed merger agreement in two days for $3.7-billion merger. So, it was wild.
I think that the thing that I learned through that is with a startup, you always need to be flexible, right? You never know exactly what's going to happen. The nice thing about it is we were able to, once we got that offer and the board felt like we needed to take it, move very quickly, get it done, and then continue to be successful inside of Cisco. I think the acquisition was a big win for everybody involved.
Delian Asparouhov:
I was going to say, maybe you can't share too many specific details, but how did you weigh or consider that option versus obviously, being lined up and ready to go public? Obviously, the public markets in 2017, especially with enterprise, are a little different than the public markets of 2020 and 2021 in terms of enterprise. Curious how the team thought about weighing those two options, especially it's such a short period of time? I imagine there is a lot of talking and very little sleeping during those 48 hours.
Dan Wright:
Yeah, I mean, at the time, the offer, I think was the highest multiple anybody paid for a software company ever. So, it was a good offer. We looked at it in terms of, "All right. Based on possible scenarios, what's going to happen with the market as well as our own performance, how long would it take us to get to this price?" There's also dilution from the IPO, where all of your shareholders are going to own less of the company after the transaction. So, we actually modeled all that out.
We had very complex spreadsheets, and then we had a conversation with the board. The consensus was when you factored in both the risk with the market and some risk with our own execution, APM was a crowded space with lots of other companies there, that it really was a good offer and one that is in the best interest of everybody involved. So, we decided to take it.
Delian Asparouhov:
And then you operate as COO within Cisco. What was that like? It seems like they did actually keep the brand and it is still pretty independent. What was easier by being part of a larger organization like, Cisco, versus what were some things you had to navigate as being C-level officer of an entity within a much larger entity?
Dan Wright:
Yeah, I mean, we were able to stay pretty independent for the first couple years. So, it was a great situation, because we had a parent company that had plenty of cash that view this as strategic, that had also some great C-level relationships with the top companies in the world, and that was very interested in helping us accelerate our go-to market.
So, for the first couple of years, it really worked really well. Especially a company the size of Cisco being in a transition and they were really moving to become more of a software company that was something that Chuck Robbins was driving as CEO, so, there was some complexity associated with making that transition, but overall, things went really well. We were able to, I think, benefit, but also, keep some of the things that made AppD a special place while I was there, so.
Delian Asparouhov:
And then after a couple years of operating post-acquisition, you ended up deciding to come over to DataRobot, which I'd love to dive into. How did that opportunity come across your plate? How did you think through? Given the phenomenal run that you had at AppDynamics, I'm sure there was a lot of opportunities that were coming across your plate. What did you find particularly attractive about the role, the company? Obviously, you're probably relatively intimately familiar with the problems that they were solving. So, why did you find their approach unique or the most appealing to you?
Dan Wright:
Yeah, I mean, for me, I decided to really take a hard look at the market when I left AppDynamics. So, I talked to all of the VCs. I looked at hundreds of different companies, talked to tons of different founders, and really did my homework. So, I had a good sense of the market. I also had some good offers in hand by the time I spoke to DataRobot. The reason that I was so interested in DataRobot was a few things. One is the size of the market opportunity. So, PwC forecasts $15.7 trillion impact to GDP globally from AI between now and 2030. So, huge, huge market opportunity.
Also, one thing that I really liked about it is that it's a platform versus a product, right? That today includes four different products within our platform, but now, what we're doing is we're able to actually build these AI-powered apps for every industry on top of our platform. We're creating ecosystem around that. I just thought the market opportunity combined with the platform to address that market opportunity created a lot of potential. And then the other thing I looked at was, "Where did I think that I and the team would be able to have a really large impact on what the company could ultimately become?"
I wanted to do something that I thought could make a really large and positive impact on the world and on the employees that work at the company, as well as our customers. For me, DataRobot stuck out, because it had some of the top data science talent in the world. We had a visionary founder, Jeremy, who's my partner working at DataRobot. We also have just a lot of people who are very ambitious and focused on their own personal growth. So, we talked about 10X-ing our employees lives while they're at the company.
I thought if you could complement that with some skill sets from people with different backgrounds, but who are very aligned on what we were trying to accomplish as a company and that idea of personal development and developing other people at the company, that you could create something really special. So, it's a combination of those three factors, the market opportunity, the platform, and then the team that really made me want to jump in and be part of it.
Delian Asparouhov:
It was obviously a very different stage, let's say, that when you were joining AppDynamics, not hugely later, but definitely later stage than obviously, when you're joining AppDynamics. What shifted about your mindset in terms of when you were considering your first role, in-house, joining something relatively earlier stage versus DataRobot slightly later stage, or were you pretty focused on this very particular stage? Were you actually looking alongside DataRobot across a variety different stages of companies to join?
Dan Wright:
Yeah, I think it's interesting, because I compare notes with lots of my friends who have either gone through this process before. They were looking for something at the time. A lot of people look at it in the absolute sense. They say, "Hey, the stage is just the stage, regardless of the company." I never looked at it that way. I always looked at it in more of a relative sense, in the sense of, "What is this company in comparison to what it can become, right?" So, even though DataRobot may look externally, a later stage company, we're still early days in terms of what the company can become. That really stuck out to me.
I'll never forget Jeremy, again, our founder... When I was deciding between the different offers I had on the table, I was really deliberating about the decision, because I thought it was an important decision. He sent me an email. It said something along the lines of, "You can join lots of different companies over the course of your career, but it's not very often you get the chance to actually do something that could change the world." AI, I think, is one of those technologies that really can change the world in a pretty unique way.
Delian Asparouhov:
Yeah, I feel like one of the things that is actually under discussed in Silicon Valley is this type of job search process. Especially once you had a really solid run, the way that that process should ideally go, how long you can take to do it, who you should be talking to is actually quite different than your very first job search, I imagine as you're leaving Gunderson. So, yeah. I guess, can you talk a little bit about how you thought about even just structuring your sort of "search process"?
Who are the most helpful people that you talked to? How did you think through the opportunities? Did anybody provide the best advice like frameworks? Do you have peers you really found that you leaned on? And then if you were, let's say, recommending somebody else that had gone through a similar, let's say, amazing ride at a company similar to AppDynamics, how they should be maybe structuring how they think about what comes next.
Dan Wright:
Yeah, I mean, the one thing that I tried to do is just be flexible on my thinking. I really tried to think about, "What are all the possible things I could go do now with my life?" That ranged from, "Hey, maybe I want to go into investing. Maybe I want to go into operating at a very small company. Maybe I want to start a company, right? Maybe I want to join something that's later stage and the whole gamut." And then what I did is I talked to people who had done all those things, especially people who had done something successfully before.
So, one of the people I talked to was Trae Stephens at Founders Fund. He's a friend. He had had a successful career at Palantir. He decided to join Founders Fund. So, he went on the investing side. Now, he's doing that. He's helping to run Anduril as well. Just people like that, who have some valuable, relevant experience who you trust and won't just sugarcoat things but tell you the good and the bad. That's important, because the grass always looks greener. You need to actually understand what's it like working in these different roles and get the pros and cons and then stack them against each other and decide what you want to do.
Delian Asparouhov:
Yeah, can you give a sense of just what your timeframe was when you first started picking your head up to when you finally made the call? I imagine it wasn't two weeks. I imagine it wasn't a year. Yeah, where did you lay in between that in terms of how long it took you to go from picking your head up to actually deciding the right opportunity?
Dan Wright:
It took me about three months, but I will tell you, those three months, I worked very hard. I had so much analysis, and I did so many meetings. I really was taking it pretty seriously. I think if you wanted to actually relax a little bit between jobs, taking a year would make sense to make sure that you could actually do it fully and feel confident about your decision and maybe get a little downtime, but I was just very focused on it. So, I went full steam ahead for a few months. At the end, the nice thing was I really felt good about my decision, because I knew again, what was in the market. I knew all the pros and cons to all the different options. I knew that I made the best decision I could based on the information I had. So, I was going to live with it.
Delian Asparouhov:
And then yeah, now speaking about your time at DataRobot, can you talk a little bit about how did you hit the ground running? What were the primary, let's say, scope, responsibilities, and maybe also just recommendations for other executives now that you're a year, year and a half in for how to hit the ground running at a company at that scale and what the ideal way of spending the first three to six months to ensure success for years, one, two, three years down the line?
Dan Wright:
Yeah, I talked to some friends who had done this before about this as well, joining a company at a point where it had a large history, a lot of have been tried and failed over the years. Also, there's been lots of victories. And then there's just a lot of people at the company. The number one point of advice that I internalized from that was make sure you listen first. Actually, if you read books about how to be successful in a new job, they'll also tell you the same thing. Listen first and do no harm. And then once you have the context, try to do something. So, that was actually the first thing I was going to do. I actually announced it at our first company meeting the day I arrived.
I said, I was going to go on a listening tour. I was going to visit all of our offices. Then I was going to come up with a plan that we were going to go execute on. I was responsible for the company's go-to market and operations. So, I wanted to know about the whole company, especially focused on those areas. The thing that happened though was COVID hit. Those in-person office visits, the getting to know people, that had to change shape a little bit. So, it was all virtual. That was a challenge.
I'm very much a people person. I like to actually meet people, understand people, have longer conversations in person. That just wasn't possible for a long time. So, we had to do it virtually, but I think still the same idea applies, which is doing as many group meetings, individual meetings. Trying to really make sure you have all the context before you just run through walls is important. And then you can move forward in a much more aligned way that's only going to help the company versus maybe doing some harm.
Delian Asparouhov:
Speaking of the go-to market, maybe a two-part question was just one, how did you familiarize yourself with the EDA product? It's a relatively technically complex product and also, wide variety of use cases. So, how did you familiarize yourself with the value proposition to the customer? And then maybe, part two to the question of just how are you thinking about the structuring of your go-to market team? Where are the segments you feel like you guys are doing really well and crushing? Where are the areas that you want to expand into? Yeah, how do you think about the value propositions for the customers across those segments?
Dan Wright:
Yeah. So, I feel fortunate that I joined the company that I joined, because one of the things that we're very focused on is democratizing AI. The whole idea behind the company is that you don't need to be a PhD data scientist to get value from AI. You can be an engineer. You can be a business analyst. Anybody who's used a Tableau Dashboard can use DataRobot. Also, you can be an executive. So, we were able to really appeal to all those personas. Actually, any of those people can use the software. So, that was the number one thing that I focused on was actually understanding how that works, how that's done. And then just seeing it, working with customers as well, you pick it up pretty fast.
So, I'd say, the number one thing that I tried to do is actually talk to people who've been in the trenches. All of our sales leaders were demoing the software. So, I was like, "Wow, that's pretty unique. You don't see salespeople demoing software very often. Show me how this works." They showed me and then also just talking to customers and seeing how people again who were not data scientists were able to get a lot of value from it. And then from our go-to market angle, what we started out doing was really focusing on just building the machine for the go-to market, things like being really rigorous and accountable around pipeline generation, excellence at every stage in the funnel, really measuring everything and holding people accountable. That has gone really well.
I think the other thing that I always try to do on the go-to market is just be very proactive. So, a lot of people don't look at leading indicators. They wait until something's wrong, and then they go fix it. We always try to be ahead of where the business is and get in front of problems before they get to become bigger problems. And then what we're focused on now is trying to really match very crisply the value propositions for every different type of person we sell to. So, all the different personas. Whether it is a head of data science, whether it is somebody who might be in risk management, somebody who is maybe your CIO or runs a line of business, or even your COO or your CEO, we talk to all of them.
So, everything from the slides that you use in your pitch deck to your demos to the next step coming out of that initial meeting, it all needs to be different depending on the situation. Not just doing that, but doing it at scale now is the other thing, because it's one thing for you to be able to do it. It's a whole another thing for a brand new rep who's new to the market, who doesn't have a ton of experience to be able to do it. The other thing that we're focused on is product-led growth. So, we actually recently launched a self-service version of the product for each of those different personas that I mentioned. We're pretty excited about that as a way that customers can get started with us and just get some value and then opt into an enterprise conversation later on.
The other thing that we're very excited about is this idea of AI-powered apps. So, we recently have been building apps on top of our platform. We launched this last year. That has been really interesting to our customers, because again, it's something that you don't have to be a data scientist. For example, we were very involved working with the Department of Health and Human Services to help with the COVID pandemic response. Those are policymakers that are using the software to make decisions. They're not data scientists. The same thing is true in business where now you can be somebody who has very little knowledge of data science and you can actually understand how this enables you to make better decisions and just do your job better.
Delian Asparouhov:
I think one of the things that is off discussed is, let's say, a tricky area to navigate with a company like DataRobot, where one, let's say, upfront revenue is much less interesting than deeply integrating with your end customer and started to build up more and more use cases and get "more and more wallet share" within the organization. But then, you also balancing that with... I don't know exactly how you guys categorize it, but I imagine heavier services revenue upfront and lots of training, onboarding, getting the customer familiar with it. And then steadily over time, that ideally looks more like product revenue.
But I guess, yeah, how do you think about your aligning organization where it's not just that upfront sale, but developing that deep relationship with the customer and getting close to them, but then also, in some ways, making sure that you're optimizing the use of your team and economics over time? So, that more and more of that is done via software as opposed to, I assume, customer success type folks.
Dan Wright:
Yeah, the nice thing about our company is that we really did focus on automation and trying to make the process of getting up and running as easy as possible from day one. So, it's not as heavy lift as you might think. So, that helps us. I think the other thing is we were very focused from the beginning on democratizing AI and doing it through two things. One is automation, but the second is we call it relentlessly practical data science education. In other words, how do you use modern tools like DataRobot to solve business problems using AI? There's no sense in AI for AI's sake. I always like to talk about experimental AI, this idea that data scientists should just work on some stuff and it never sees the light of day. That's okay. I think those days are gone.
Now, AI is really a tool to help you solve a business problem that you couldn't solve before. It just wasn't possible, right? So, with that, we actually developed education. We have the ability to do mass education for large companies, as well as small companies when they say, "I want you to educate all of my people, whether it's an executive, whether it is a business analyst, data scientists, and upskill my people. Teach them how to use this and then really change my culture." That's one thing that we focus on is really telling our customers that this is a cultural change for the whole organization.
You need to go from just being reactive and, "Hey, the news is this. All right. Now, I need to do this," to actually getting in front of the news and shaping the news by doing all of the different scenario analysis on, "What is going to happen if I make this decision?" And then using your data to make a better decision, which then shapes the news. So, it's a real cultural change, but the great thing is while there is some enablement there and there's some services there, pretty quickly, people can be self-sufficient using a platform like this. And then, as you said, over the long term, that creates a lot of value for everybody.
Delian Asparouhov:
So, both at AppDynamics and DataRobot now, you've had a COO title. I feel like one of the trickiest parts of COO titles is it can be actually wildly different between organizations and mostly dependent on in some way how the CEO likes to work and where their strengths are versus where they might not be that strong or prefer not to spend their time, their communication styles, et cetera. So, I guess, can you talk a little bit about maybe the differences between your COO role at AppDynamics versus at DataRobot and maybe how that relates to the underlying relationships with the CEO and what their preferences, strengths, attributes are?
Dan Wright:
Yeah, I mean, the blessing and the curse of the COO role is it's very flexible. It means a lot of different things at every different company, right? So, I actually enjoyed that. Because even when I was just at AppDynamics, it allowed me to learn about a variety of areas. So, I started off and I was running all the operations, functions. I was running finance and accounting and all of the G&A and operations. Over time, while I was there, I took on more of our go-to market. That was all great learning for me, because the thing is you really do need to go deep in these areas to understand them. It's also to know, "How do I build my team," right? I think the mistake people make sometimes is that they don't go deep. So, they don't develop that understanding.
So, I really tried to do that in every one of these areas, and then build a great team. And then I could expand what I was doing. DataRobot from day one, I've also owned our whole go-to market. That, I think, was a natural thing after being at AppDynamics, but I've had to learn a ton, right? I mean, I think you're always learning.
So, what I would say is really critical for anybody who's looking for a COO role or a President and COO role is you have to have a great partner as your CEO. At AppDynamics, I was fortunate to have a great partner with David Wadhwani, who's still close friend of mine, now at Greylock. And then at DataRobot, I'm really fortunate to have Jeremy, our founder and CEO as a partner. If you have a good relationship there and if you feel like you're complimentary, the rest takes care of itself. Oftentimes, the role will change month to month, then quarter to quarter and year to year, but that's the beauty of being in a startup, right? Everybody's role is changing all the time, and you're constantly learning.
Delian Asparouhov:
If you're giving advice to somebody who's in an earlier stage in their career, maybe just coming out of Gundersen or something like that and trying to get into the operating in-house side of things, what are the best suggestions that you'd have for them in terms of where should they start, how should they think about their career position in order to get into a position like yours, where they eventually want to be, let's say, COO of late stage tech company, ready to go, out on the market and maybe become massive? How do they structure their career in a way that gets them to where you are today?
Dan Wright:
I mean, first thing is to know where you want to go, right? I think it's interesting to me how many people just drift and then think that they'll find themselves in some magical place that they'd like to be. I really encourage everybody and this is actually one thing that we have programs around at DataRobot, try to understand, "Where do I want to be in 5 years, 10 years?" What is your current trajectory related to that? Are you on that track? If you're not, you're going to have to do something differently. And then I think if you're not on the track that you want to be on, just being honest with yourself about that and then being prepared to take a risk. That's one thing, especially for people who may have been trained in the law, they tend to be a little risk averse.
I always tell people, don't be afraid to take a risk, but make sure it's the right risk, make sure it's risk adjusted. So, for example, when I was choosing AppDynamics, I didn't just jump at the first startup. I really did look at all the different things. I understood the market. And then I decided to join the startup that I felt like was the right startup, the right balance of risk and reward and where I was going to be able to grow in the direction I wanted for my career, right?
I've continued to do that at every step since then. It's worked out pretty well. So, I think those are the two things I would say is one, have your destination in mind, know where you want to go. Two, don't be afraid to take a risk, believe in yourself. You only get one shot at life. So, why not try to actually make it the life that you actually want?
Delian Asparouhov:
I feel like the thing that I see in Silicon Valley over and over again is the people who consistently take big swings by default almost always end up having the most interesting careers, but the important thing being that they get smarter about which swings they're taking. I think it's hard if you're a total outsider to know how to take risk and how to assess it versus as you've been here for 10, 15, 20 years, it actually gets to be pretty obvious which companies are going to be succeeding, which ones aren't, what the best risk adjusted opportunities are.
So, I guess, yeah, how do you feel like you've gotten smarter over time about assessing, as you said, the risk, right? You don't want to necessarily just jump at the first startup. So, maybe by being a venture lawyer, you had really broad exposure to a bunch of startups. But I guess, how do you feel like that's progressed over time? Where maybe by the time you were deciding to join DataRobot, you didn't have to rely as much on external advice, because you had so much, let's say, internal knowledge. How do you feel like you got smarter and smarter over time on assessing which opportunities and which risks make sense to take?
Dan Wright:
I think it's like anything else, you just want to get as much data as possible. So, the way that you do that is through networking. Early on, I really tried to make a point of just reaching out to people at other companies and getting to know them, understanding what's going well, what's not going well at their company, and why, and then watching out how things would progress over time. I mentioned those startups that I used to work with back at Goodwin and seeing which ones did well and which ones didn't. That was just more data.
And then as I've been able to do that, also, investing in companies, getting involved as an advisor or board member in companies, and all those relationships build on each other. You track all these different companies. It just provides all this data that you can organize and say, "All right, these are the common factors that I see that are highly correlated to a great company."
I think the beauty now is that you don't have to do this as just yourself anymore. There's lots of different ways, whether it's online through different platforms to get a lot of this information. So, you can use that as well, whether it's CB Insights or Crunchbase or going on Clubhouse. There's lots of different ways that you can learn about what's happening in the market and what companies are doing well and likely to do well in the future.
Delian Asparouhov:
I guess, this is the first time I've had Clubhouse show up on an Operators Podcast interview. So, clearly, the app's doing well. I feel like there's two camps, religious camps on when you're in an operating role and focus on building a company, the potential value, but then also the potential downsides of external board member responsibilities if you join, angel investing on the side, advising, et cetera.
I guess, yeah, can you talk about the value you've seen from that, obviously, in relation to learning about how to gauge risk adjustment, but maybe even value in your actual, let's say, operating role, and then how you think about balancing that without either distracting from the core focus and core goal and how you think about that? How much time do you dedicate to it? How do you think about that balance and whether or not you think more people should be doing that?
Dan Wright:
I mean, I think it's all about balancing priorities, right? I think the idea that's used to be out there that "Hey, operators should just be operators and not invest in any companies," I just don't think that's correct. I think that you get so much insight into the market. What are these different companies that are doing that's allowing them to be very successful? What are the huge mistakes that they're making that's taking the company? It's just more signal that you get if you're tracking these things. So, I think it's hugely value add, not to mention all the networking opportunities that you get out of that, and that can lead to everything from help with recruiting and people make companies. So, that's critical to leads for your go-to market teams. So, I think it's really valuable.
I think there's a balance though with you need to keep in mind your number one priority as an operator needs to be that role. So, that really needs to be the bulk of your time. Your investing can't get in the way of what you're really focused on trying to build an important company. So, I think, what I would say is if you're thinking about doing it and had the means to do it, it's definitely worth doing. There's a lot of value in it in multiple ways. But at the same time, just keep your priorities in mind and make sure it doesn't disrupt what you need to do on the operating side.
Delian Asparouhov:
Yeah, no, totally agree. I think, yeah, there's ways to balance it. Yeah. I'm maybe the reverse investor now, hopping back into operating, starting a company. There's so much value to having that broad perspective. Yeah, Dan, thanks so much for taking the time today to hop on the podcast. I really enjoyed the conversation.
Dan Wright:
Yeah. Thanks for having me. It was great talking to you.
Delian Asparouhov:
Thanks for listening, everyone. If you'd like to support the podcast, please sign up for a paid Substack subscription, which we use to pay for transcripts, mics, and other improvements. If you have any comments or feedback on what kinds of questions I should ask, who should come on the show or anything else, please do let me know. Have a great rest of your day.