In the latest installment of Ropes & Gray’s alumni podcast series, Alumni @ RopesTalk, IP litigation partner Matt Rizzolo interviews Jason Idilbi, general counsel at Passport Labs, a mobility software platform that facilitates mobile parking and transit ticketing applications. Jason reflects on his “non-linear” legal career path, which began at Ropes & Gray in 2008 and led to roles as a judicial clerk, litigator and in-house counsel. Now at Passport, Jason talks about the most difficult project he’s had to tackle in the last three years, and also what he looks for when engaging outside counsel.
Matt Rizzolo: Hello, everyone. Welcome to the latest episode of the Ropes & Gray’s alumni podcast. I'm Matt Rizzolo, a partner in Ropes & Gray's Washington, D.C. office. I specialize in intellectual property litigation. I'm joined today by my friend and former colleague, Jason Idilbi. Jason began his legal career as an associate back in 2008 in the throes of a different financial crisis. He and I started together in Ropes & Gray's D.C. office. Today, Jason is general counsel at Passport Labs, a fast-growing company based in Charlotte, North Carolina, which provides a variety of software solutions for mobile parking and transit ticketing applications. He's also very active in the Charlotte legal community. Jason, thanks so much for joining me during this rather interesting time. Given that we're both broadcasting from our respective homes and have multiple children each, hopefully we'll get through this without some child-related interruptions. I'll start you off with an easy question – can you tell us a little bit about Passport and what you do there?
Jason Idilbi: Passport is a software company based in Charlotte, North Carolina. We provide payments, account management and back office support to parking and transit operators, mostly municipalities and interlocal agencies like transit agencies. We're considered a B2B2C company. Our direct clients are these operators of parking and transit assets, but ultimately, it's their constituents that interact with our services the most. For example, someone like you or me utilizing a parking app on our phones to initiate a parking session or purchasing and using transit passes, like bus or rail tickets.
Matt Rizzolo: Sounds like a really interesting business to be in. Now you're the general counsel. How long have you had that role?
Jason Idilbi: I have been here just a little over three years. I just celebrated my three-year anniversary two weeks ago today actually.
Matt Rizzolo: Congratulations. How did you end up at Passport?
Jason Idilbi: You touched on when I started my career at Ropes in 2008. I took a little bit of a non-linear path, I guess I would say, along my way here. I was at Ropes for about two-and-a-half years. From there, I went to a clerkship on the Fourth Circuit and that's actually what brought me to Charlotte – my judge has his chambers here. From there, I went to another private practice position as a litigator at a firm in Charlotte. Then I landed my first in-house position as senior counsel at the company. And it was from there that I came on as GC at Passport three years ago.
Matt Rizzolo: What's your day-to-day like as general counsel?
Jason Idilbi: I think you'll hear from in-house attorneys, the common experience: there is no same thing every day. The only thing predictable about our days is that they're unpredictable. I think our dynamic is a little interesting too, being a fast-paced high-gross startup where we have a very open and collaborative culture, which makes for real-time triaging multiple times throughout the day – ad hoc meetings interrupting what might have been what you anticipated working on. It's very fluid and it makes for an interesting and nimble dynamic, which I enjoy. There's never a dull moment. I do try to bring some order to my days to make sure I can keep my focus on my most impactful work and move things along. I do try to block off time each day where I can catch up on emails and get some work done with minimal interruption. I manage a team of other lawyers and I'm also on the company's senior leadership team, so I tend to have six meetings every day as well, whether it's one-on-ones with my direct reports, weekly legal team meetings or leadership meetings. Every day I walk into the office, or at this point, just logging in from home it's always an adventure what each day will hold.
Matt Rizzolo: What was the most challenging for you about going in-house from a firm in private practice?
Jason Idilbi: When you are working in a sophisticated law firm environment like at Ropes & Gray, or the firm that I worked at in Charlotte, Moore & Van Allen, you are accustomed to your colleagues at all levels from the legal professional assistant staff, the library staff, anybody up to the most senior partner ranks a level of experience, sophistication and maturity that is what we consider table stakes. It’s part of what is involved to operate at a high-level like that. You get accustomed to being able to operate from a common framework where things are not taken for granted, but just assumed. There's not a lot of education or awareness that needs to be ongoing because everyone's had that level of rigorous training that got them there in the first place – obviously, in the case of lawyers, seven years of training and then the on-the-job work. What's unique about being in-house, and I see this at Passport and I saw this in my other company as well before coming here, is that you end up dealing with people at all different levels of experience, maturity and sophistication. Sometimes, it requires you to spend a little more time to explain something in a way that's digestible to the person that's on the other side receiving it. When I'm having a conversation with my leadership team, I know that I can shortcut, for example, a lot of background information or just general awareness building about a particular topic. When I'm dealing with a younger sales associate, someone who might not have a college degree, for example, or it might be their first real job out of college, there's a level of having to build a framework for the discussion. A lot of what I and my other attorneys have to do is help build up the knowledge base so that we can best support the understanding of our colleagues as far as what we're doing and what we need to do from a legal perspective when it comes to where their work intersects with ours. And make sure we speak at the right level, depending on who the audience is.
Matt Rizzolo: That's something that I recognized early on as a challenge for a private law firm attorney in communicating with your clients. The general counsel or some of the more senior attorneys there might have a good grasp on things, but whether you're dealing with lower-level attorneys or non-lawyers, you really have to tailor your message in the amount of legalese or jargon you use. In your time at Passport, what's the most difficult project you've had to tackle?
Jason Idilbi: For purposes of discussion, I'm going to set aside what's ongoing right now in light of this pandemic. I think that will overall end up being probably the most challenging dynamic and work in my entire career most likely. What I would say is around this time last year, we were advancing the ball on two projects. We did a capital raise, which was our Series D, and that was contingent on an acquisition that we were also working on at the same time. It was a very careful balancing act to advance both of those deals simultaneously and make sure that the timing lined up just perfectly so that we could close on the right schedule to make everything work. This all happened in the second quarter of last year, and over that quarter through leave and attrition, I was actually down a full-time resource, so we were really operating at seventy-five percent capacity on the legal team. It was a rather Herculean effort, not just on the legal-side, but a lot of the folks on the corporate development side of things overall. When I look back on how we pulled it off, it makes me scratch my head and think, "That was pretty interesting, I'm really glad we pulled that off." A different team or a different set of circumstances and it might not have happened, so it's something that continues to fill me with pride.
Matt Rizzolo: Moving from one difficult project to the current crisis – obviously the coronavirus spread and the global pandemic here has caused major disruptions of companies large and small. What major issues are you dealing with?
Jason Idilbi: I think the biggest thing, and I think you might imagine it and listeners might imagine this, from just the nature of the business that we're in, our bread and butter is parking and transit transactions. We are recession proof in the sense that people are still moving around from place to place, job seeking, still consuming goods and services, going retail shopping and things of that nature, going to banks and utilizing parking and transit services. What we're in now is almost more of a wartime situation, where folks across the nation are subject to shelter-in-place and stay-at-home orders, or if not, they're just exercising social distancing guidelines. The net effect of that is that people are not going out in public, they're not utilizing parking services, they're not utilizing transit services, and so it's meant overall a very steep decline in our transaction volumes. That obviously has a direct correlation to our revenue model and a very steep decline in revenue, so we're having to adjust to that dynamic and figure out what levers can we pull to curb some of our burn rates – are there any short-term revenue plays that we can make? Things of that nature – so it's really just trying to get as creative as we can, but it's on the revenue-side and on the expense control-side to make sure that we can emerge from this and hopefully be in a stronger position. What we hope is that the corollary to the steep cliff we've seen will be a steep rise once the pandemic subsides and people do start to get back out there and go about their daily lives and utilize these kinds of services, to the same extent as they were before. Part of the challenge is that it's all completely unknown at this point and we're just having to forecast and re-forecast, and then play out multiple different scenarios in how our business will respond to those challenges. Total mystery how things are going to go and that's made for very difficult planning.
Matt Rizzolo: I think we're all hoping the recovery will be sooner rather than later, but we'll have to see. I want to take you back to your Ropes days – how did you pick the firm and what group did you work in?
Jason Idilbi: I'll take the second part of that first – I was in the litigation group. For the first part of the question, how did I pick the firm – I was actually thinking back on that. Ropes & Gray was my very last on-campus interview during that fall of my second year of law school recruiting cycle. I actually fortunately had some good luck at that point and I thought, "I don't know that I even want to keep this interview." I was ready to make a decision and move on, but I'm really glad I stayed the course. My on-campus interview was with Richard Batchelder, a partner in the Boston office. He and I spent the better part of our 20 minutes together talking about UNC basketball because he was a UNC alum as well. That really stood out to me that I think he felt that I had a baseline level of smarts and competency to do well at the firm, and it was really more about interviewing for fit and culture than anything. I ended up seeing that dynamic play out across multiple different interactions along the process and then in the summer program as well. I was very impressed, of course, throughout all of that, and you folks really ended up standing out far from the pack as I was going through that process. It was a great place for me to spend my summer and then start my career.
Matt Rizzolo: Do you have any favorite memories from your time at the firm?
Jason Idilbi: I think all of us back then during that period of time, those were some heydays for our class during the summer of 2007, when we were summer associates. We had a lot of fun and the firm was very keen to create a great summer experience for us. As much fun as that was, it's more of what I came to experience when I was at the firm – just experiencing the level of collegiality and kindness among the folks there. For a while, we had a recurring Friday afternoon happy hour in the office where we would have food and beverages brought in, and it was a nice opportunity for folks to just connect with their colleagues as we eased into the weekend and just shoot the breeze for a little while. Those were some really nice memories and it created some very meaningful interactions with people outside of the folks that you worked with on a day-to-day basis, so that's one thing that I always enjoyed. Of course, among the associates, we had a really nice rapport outside of the office too and regularly got together for social events and whatnot. You might remember, for awhile, every holiday period we would have a “progressive party,” as we called it, where we would go from one person's apartment or condo to the next and sample different drinks, food and things of that nature, so those are some really fond memories that have lingered.
Matt Rizzolo: Career-wise, were there any attorneys at the firm who really stood out as influences for you?
Jason Idilbi: Again, my overall impression of Ropes is that it's just a great place full of very smart and very kind people, and so even thinking to pinpoint anyone in particular is an exercise in and of itself. Thinking back to the work that I was doing and the folks that I interacted with the most at the partner level, I really felt that Colleen Conry and Doug Hallward-Driemeier had a big impact on me. They both joined soon after we started, but it was during that same period. Both came from government. They're obviously very talented in different ways, but both of them were very smart, sharp colleagues who were really invested in our career and took seriously a mentorship role, but also were just the nicest people too. Just really wonderful people to work with – very kind, understanding and willing to put in a good amount of effort into developing you. Colleen and I had a project in Hungary for a period of time that required us to travel there over multiple trips, so we had a lot of nice bonding experiences as a result of that as well.
Matt Rizzolo: Since you've gone in-house, I've noticed you've written some articles providing tips to succeed as an associate, both in billable work and then in business development. What advice do you have for outside counsel who are trying to get business from you or other folks in-house? What are some things that outside counsel do well or don't do well?
Jason Idilbi: It's interesting that you ask the question because the next article that I was noodling on was exactly that topic – I'm going to take a different spin on it. It was originally, what to do to not get fired as outside counsel, because frankly, it's unfortunately common for outside counsel to not deliver. That's another, I think, common experience that you'll hear among in-house attorneys, but I am going to take a different spin on it. If you go back to the very first article that I wrote on the tips that are directed toward associates, the recommendation I gave was to think that it's your partners as the folks you're delivering output to – those are your clients. It all comes back to that notion of “who's the service provider and who's the client,” and so this is just approaching it with a slightly different lens. Ultimately a lot of the advice that I wrote is to put yourself in their shoes. “What are your client's pressures? What are their limitations in terms of both capacity, budget, all of those things? When you're delivering work products for them, what is the downstream impact of that? Is it something that they just need a quick consumption to report on something or are they looking for a more formal memo?” It's asking the questions when that's not clear. It’s very easy to have runaway projects and budgets that get thrown out of whack on the in-house-side because something took longer and a client or one of your law firms wants to bill you for something that was not the scope that you were looking for. It's just really about figuring that out and asking the questions when it's not apparent. Ultimately, one headline about this is: do what it takes to make your client's life easier. I think that ethos, so long as that permeates the relationship, will be what sets you up well for success. A slight variation of that, and I see this on the Passport-side of things where we are a growing company, we don't have relationships that are as long or as established, we don't have the insights into budgeting and spend that some other companies might have, but we want to be treated fairly. We want to feel like we are not considered a second-tier client, that our money is just as good, our matters are just as important, our outside firms are delivering the same work products regardless of any of those circumstances, we're still valued and respected, and that the relationship is being nurtured. One day, who knows, it's hard to predict the future, but Passport might go public or we might be hopefully a unicorn company. Now I say this regardless of that particular dynamic, but showing your clients that you are invested in them, that you care about them, that you're proactive and practical in the advice that you give them, and just having that mindset underlie the relationship is really the key.
Matt Rizzolo: What advice do you have for attorneys who are at firms who think they want to move in-house or may want to move in-house one day? How would you say they should go about tailoring their career or network?
Jason Idilbi: I think you hit on the two major aspects of it – the career aspects and the networking. When you're in an in-house position, a lot of us are generalists. Now there are, of course, bigger companies who have their own internal patent counsel, their own internal employment counsel, their own internal litigation counsel, but that's fairly uncommon for a lot of companies. I would say that among my peers, that's not a very common structure to their legal departments and that you need to be a utility player that has at least working competency or an ability to get up to speed on a lot of different areas quickly. I have looked for those skill sets and that range of experience when I've been hiring folks. That might be hard for somebody who is in a particular practice group, like in private practice at a firm like Ropes where over time you get more and more specialized and technical, but there are other ways to supplement that too. For one thing, pro bono participation or other participation in perhaps interdisciplinary groups, for example, in the areas of data privacy. At my last firm, we didn't have a data privacy team, but we formed our own interdisciplinary team, so I think there are ways that you can maintain a very specialized practice but still have enough exposure to some other areas to be able to demonstrate a competency and an ability to have the dexterity of mind to step into an in-house role and be able to deliver. I will say, one thing from my own experience, when I was looking to go in-house, the fact that I was a senior associate with exclusive litigation experience made it a little bit more difficult for me to bridge to a role where I had more of a corporate practice. When I looked back on my own experience I thought, "How could I have supplemented that with some other things that I could demonstrate more immediate value?" Fortunately, I found my first in-house boss who took a leap of faith on me and recognized the potential there, and I was grateful for that and I try to adopt that same mindset.
As far as the other component to that, the networking piece, what I've seen play out over the years is that a lot of positions end up being, I don't want to say earmarked, but typically there are frontrunners for these positions almost as soon as they're posted. The best way to prepare yourself for an in-house career is to just be very intentional about building your network and having the connections to the right folks that can help you get there. It's very competitive to go in-house. In-house positions are desirable. I would say in my experience, they're no less work than in private practice, but they're certainly desirable and there are a lot of lifestyle aspects that make them compelling. When I've been on the hiring-side of it in my role at Passport, it's been an embarrassment of riches really – I've had some highly-qualified candidates that I could pick from. I think having the right connections, either to folks in the company or having the right folks that can be champions for you and help you open doors that might not have direct connections to, I think that's key. Much of what I see creating success in this world, like so many other things, of course, is just relationship-driven. It's having good relationships and people that can vouch for you. On paper, a lot of attorneys can look very qualified, and so to know that somebody has a favorable, personal relationship with somebody can be a very influential thing in that process.
Matt Rizzolo: It sounds like a mix of who you know, who knows you and laying the groundwork through the course of your career. Let's end on some light notes with some fill-in-the-blank questions, a lightening round here. My favorite sports team is...
Jason Idilbi: The UNC Tar Heels.
Matt Rizzolo: My ideal Friday night is spent...
Jason Idilbi: At our local taco shop having a pitcher of margaritas, which I wouldn't share with my kids, but we would all be sitting on their patio having tacos – and then movie night after that.
Matt Rizzolo: If I wasn't a practicing attorney, I'd be...
Jason Idilbi: A historian.
Matt Rizzolo: If someone handed me $25 million today, I would...
Jason Idilbi: Take a sabbatical.
Matt Rizzolo: Ropes & Gray is...
Jason Idilbi: The best place to start your law firm career if you want to be only at one firm for your entire career.
Matt Rizzolo: Thanks, Jason. I really appreciate you taking the time to join me today. For all of you listening, thanks for joining as well. For updates on Ropes & Gray alumni and firm news, and additional podcasts, please visit our alumni website at alumni.ropesgray.com. You can also find our podcast on Apple and Spotify.
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