Esquire is the term that American lawyers use to set themselves apart from other professionals. But it’s also emblematic of the challenges that many young attorneys face in today’s crowded job market.
Julia Shapiro founded a talent platform that leverages those changes in the legal industry. By matching short-term law gigs with skilled experts, she’s creating a new path forward for law school grads who can’t find — or don’t want — the traditional partner path at big firms.
It’s the story of Hire an Esquire on The Build.
Announcer: [00:00:00] From 2820 radio in Philadelphia, it's The Build. Conversations with entrepreneurs and innovators about their dreams, their triumphs, and their challenges. Joe Taylor: [00:00:14] Esquire. That's the terms that American lawyers use to set themselves apart from other professionals. But it's also emblematic of the challenges that many young attorneys face in today's very crowded job market. Julia Shapiro founded a talent platform that leverages those changes in the legal industry. And by matching short-term law gigs with skilled experts, she's created the new path forward for law school grads who can't find, or don't want, the traditional partner path at big firms. It's the story of Hire and Esquire coming up next on The Build, Announcer: [00:00:52] The Build is made possible with support from 2820 Press. Providing business consulting and content strategy services to customer obsessed companies nationwide. Joe Taylor: [00:01:04] I'm Joe Taylor. This is The Build and welcome this week to Julia Shapiro, founder and CEO of Hire an Esquire. Where are you joining us from today? Julia Shapiro: [00:01:19] Hi, Joe, thank you for inviting me to the show. I am joining from San Francisco, California. Joe Taylor: [00:01:23] So you have, I think, a really compelling background. You started this business on the East coast, but you found some traction on the West coast. Tell us a little bit more about the origin story of Hire an Esquire. Julia Shapiro: [00:01:38] Sure. So the origin wasn't very planned. Things turned out much differently than we expected at first. So I moved to Philadelphia for law school and loved the city and practiced as a lawyer there. And my plan in life was to continue to be a lawyer. It wasn't to be an entrepreneur. But while I was working at Pepper Hamilton in Philadelphia, I saw that the legal industry was changing dramatically and that the partner track was slowly evolving and that new career opportunities were popping up. And the way law firms ran, wasn't going to continue. While I was at Pepper there were, at some point, over 200 contract attorneys just in the Philadelphia office at any given time. And so I saw that even law was changing to an on-demand workforce, and I saw these trends happening and I saw how horrible it was to staff attorneys. I noticed that the staffing process hadn't evolved since mid century and staffing was being done very differently than it had been in the mid century. So initially while working at Pepper, I went to look for a product like Hire an Esquire to recommend that Pepper use the product. Seems to me completely obvious that somebody would have put this process online. They were already working marketplaces, Odeski lands for instence. So I thought surely there was something for law and I wanted to find it and use it. When the products did not exist, I suddenly became obsessed with building it and my plans to continue being a lawyer evaporated. As I found other people in Philadelphia to help me build this product for equity. And initially we never planned to go for venture funding. This was supposed to be something that we bootstrapped. We started it, we all had other jobs and we just did it in our free time for fun. Then we got to a point where we realized that this was going to take more resources and time that enterprise selling, selling into law firms and fortune 500 companies who would be our clients was not going to be something we could do in a bootstraps fashion. So that is when we went to set out to raise money. Joe Taylor: [00:03:34] So I think you bring up a couple of really interesting things. Let's try and knock them down. I think one of the most compelling things here is you graduated law school 2007, right before one of the biggest recessions of the last century. And it seems like that 2008 recession like it did for a lot of industries really up ended the legal profession. So tell me a little bit more about what you observed the big shift in the last 10 years toward the use of contract attorneys versus what large law firms previously did to staff big projects. Julia Shapiro: [00:04:09] So I think the shift was more gradual than seismic. So even before the recession, there's this thing called document review, where as the world modernized and people started using email, you needed a lot more lawyers to review information and lawsuits because a lot more copy material was being produced that was saved. So, whereas it used to be documents that would be reviewed in litigation, fit in a warehouse or in file cabinets. Now there was, you know, millions of pages. So even before the recession, when a big lawsuit would happen and there would be. Now millions of documents to review, they started using contract attorneys to bring in armies of attorneys on a short-term basis to review these high volumes of documents. And obviously you can't keep a hundred attorneys on staff at a firm for a big case. That's going to go away. So already the, you started increasing in the late nineties and the early millennium with. The growth of volume and data to review in litigation then with the recession, it didn't happen all at once. Everyone seemed to, even in 2007, 2008 attorneys weren't getting jobs out of law school. There were a lot of other things going on with law firms and with the practice of law that were showing the business model wasn't sustainable even slightly before the recession. So slowly, a lot of factors came together. And it wasn't right after the recession law firms said we need to get more efficient. It took a lot of time and a couple of major law firms shutting down and shifts in client behavior and more driven by client behavior from the recession. And just over time to actually change law firms. I don't think that it was immediately at the recession that it changed. It took many years after that. Joe Taylor: [00:05:43] So it sounds like a lot of the asks coming from clients, clients are seeing this new nimble platform based behavior and a lot of other areas. And they're asking their attorneys, their firms to start behaving the same way. Where do you find the talent to be able to meet those clients? Julia Shapiro: [00:06:03] You're right. It's completely driven by client behavior and client requests and demands. And where we find the talent. We do a bunch of different things. We use job boards, we use law schools and alumni relationships and alumni career boards. We use social media. But another thing that we found is really powerful for our network is attorneys are really excited about what we're doing and the vision to be a new way to practice law and the vision of a fluid workforce. A lot of attorneys really were discontent with the typical attorney lifestyle, right. The 90 hour week, a lot of attorneys were dying for an alternative and that we helped to develop that market and provide that alternative where you don't have to be stuck on the partner. Track is really engaged with attorneys and particularly when we get press and their news articles about us. We get tons of attorneys signing up directly on our website. And then when we have attorneys work with us and have a good experience, a lot of times when you're a lawyer, your friends are lawyers. So they refer people to us. So one of the most powerful ways that we've gotten people into the system is just community engagement and excitement by the concept, and then referrals between other attorneys. Joe Taylor: [00:07:08] So everybody thinks that launching business nowadays is as easy as publishing an app or putting something up for sale. And already I've heard you mentioned talent platform with traditional recruiting and traditional enterprise sales. It sounds like there's a lot of brute force effort going on under the hood here. So tell me a little bit about the skills that you had to pick up that your education didn't necessarily prepare you for as you took on the CEO role. Julia Shapiro: [00:07:37] Completely. So law school prepares you to not be a business person, I would say. From my background, I wasn't from a background of a family that had a lot of people in business. My parents were teachers, my extended family had a lot of engineers, which also isn't good for business. So, and a lot of these professions they actually teach you to stay away from risk. And so in business, you have to learn to take lots of risks and be comfortable with that and do a lot of things that are incredibly uncomfortable. Like sales. So I had no training in sales. I waitressed a lot in high school and through college, but that was about as close to sales as I had ever gotten. So learning the enterprise sales process took a long time and then the enterprise sales process on its own takes time. So I identified that I was having trouble selling this product. That seemed incredibly obvious to me. I think a lot of entrepreneurs that you interview probably feel this way, but this is a no brainer. This is the greatest thing in the world. Why aren't you buying it right now? I don't know if you see or hear that from a lot of entrepreneurs.. Joe Taylor: [00:08:29] Almost every single time. Julia Shapiro: [00:08:33] You don't, you have to flip your frame of reference and viewpoint that, especially in enterprise sales, there's a lot of barriers to people buying there's, particularly with law firms, there's bureaucracy, not one person can make a decision. You need to get 20 weighers to agree on something which doesn't happen very easily. And a lot of legal tech companies that started around the same time we did our after that were really well-funded. They had. People with the founders, with the pedigree that VCs like to see, they got big checks from VCs and they failed within a year because when you raise a bunch of investment money, your investors expect to see a return or some traction within a year. And the legal sales cycle takes a year. So even if you have a very strong introduction into the firm and somebody that's very important and important client that walks you into the firm, it still takes a couple of months after that, generally, to get through all of the law firm processes to sell into the law firms and I think that was one of the biggest skills I learned as an entrepreneur was how to sell into law firms and how to work through those processes. And that's a harder battle than building a product. In my opinion. Joe Taylor: [00:09:31] I think it also alludes to the other hurdle that you overcame, which was figuring out how to cut this path between bootstrapping and angel investing. Tell me a little bit about how you were able to attract investors and then manage their expectations as you've built this thing in a fairly steady cadence over the past few years. Julia Shapiro: [00:09:54] So it's funny because the traditional VC, if you talk to what traditional VC is a him, so I'll say if you talk to him, they hate the trajectory of our company. They say, you go out, you raise money right away. You go big or you go home. But as we've seen, when VCs have funded, tried to fund enterprise sales, enterprise legal companies, that doesn't work. Bootstrapping well, it doesn't look clean. And the typical startup story, it actually was the best thing we did because by the time we accepted our first investment check, we had our first 2:00 AM, watch a hundred clients on the platform. So we already had proof of concept. And that was key for our products, which might be different for someone starting a business in a consumer space. But for the enterprise space and an industry that VCs traditionally and investors don't like, which is legal. It was really good to have that traction already before we took our first amount of money and raising money took us about a year. So we had developed a lot of relationships with investors over that time. And there's this myth that you go into a room and you pitch investors and they love your idea and they're captivated by your PowerPoint. And they write you a check on the spot. I know very few people where that happens unless they come from privileged backgrounds and they already have strong family connections to money. That's the only instances I've known that to happen or the products already runaway success, and everybody wants in. But in the early stages, it was very much for a year. Building relationships with angel investors and keeping them updated on our progress as we sold more and we got better clients and build our network up. So that's how we made the jump. Most of the comparable entrepreneurs, I know that is more their path, but again, if you come from a privileged background or you have some other connection to the industry, then you probably have a very different path. Joe Taylor: [00:11:29] I think it's the downside of the shark tank effect because everybody sees a heavily edited broadcast. And then they don't realize that there are months of research that go into even picking shows up on that show. And then that's an entire day edited down to a 20 minute segment. And even that is an entertainment experience. It's not really what happens when you go out and seek investing. One thing that I think is interesting though, is that you spent a lot of time building those relationships on both the sales and the investor side. And now you have an interesting dilemma and interesting challenge, which is. The next phase of the company is really going to be on the back of retention. So how do you shift gears from that sales pitch mentality to actually client success and management and keeping a client on your back? Julia Shapiro: [00:12:22] But it is something we did over the last year was build out customer success processes. And the flip side of having a really long sales cycle is the clients tend to be a lot stickier. So once you have an enterprise client like a law firm or an in-house and in-house legal department, Fortune 500, you go through crazy procurement processes and you have to really mess up often for them to not work with you anymore. And of course, we never want to cross that. Never want to even get close to that. We want to keep everyone incredibly happy. Joe Taylor: [00:12:49] Let's not test the theory. Right? Julia Shapiro: [00:12:52] Exactly. Exactly. And all departments keep getting leaner. We have fortune 100 clients and their processes keep getting leaner and quicker. So I think that there will be a time when even enterprise vendors will get kicked off the roster really quickly if they make a smaller mistakes. So we've already worked very hard on. The client experience and the attorney experience to keep everybody happy and on board. And we do a lot of things with basically hiring additional sales and account managers to check in. We build additional technology into our system to check and verify things, to kind of flag things, if something is off or going wrong. So that's definitely part of the stage of the company that we're in right now. Although I will say that we in enterprise and particularly enterprise industries like law that are have a very long sales cycle. On the other side, you tend to have less of the problem with consumer products where tomorrow is the new hotness, and everybody was on this app today and they're on the next step tomorrow. You have a little more time in the enterprise and in the legal industry, Joe Taylor: [00:13:46] coming back to your original example. If you were able to get 20 attorneys on a procurement panel to agree on something, it's unlikely that someone else is going to come along and hit that magic number. When the fact that you've built a good relationship means that barriers even higher, because even on your worst day, someone on that panel is going to say, Oh, but we already did this paperwork once. Julia Shapiro: [00:14:11] Exactly. And there's a lot of paperwork and they hate to do it because often it's some lawyer that has lots of paperwork from their own clients to do so, doing it for a vendor for the firm is not their favorite thing at all. Joe Taylor: [00:14:22] It's also knowing your audience there, knowing that if you've got a bunch of folks who are on partner track any hour, that you're doing something that's not billable is an hour, they don't want to be spending. So along those lines, Thinking now about the talent experience and the recruiting side at the same time that you were building Hire an Esquire, a number of other companies were moving into this talent space, really building on top of the 1099 experience for folks who don't know the phrase, that's the form. That the IRS gets that you eclair what you earned as an independent contractor and a lot of companies like Uber, or I think about some of the virtual assistant companies like Zirtual Zirtual made headlines because they kind of imploded when they made the transition from. 1099 to W2, actual staffed, hourly employees, because a number of courts ruled that the talent platforms could not justify flagging folks classifying them as independent contractors. It sounds like you made the choice to go in very early and commit to the W2 side of things, which in hindsight looks like a fantastic decision. What was the thought process there? Could you have at some point gone to 1099 route. What did doing the W2 root mean for you? Julia Shapiro: [00:15:44] So we did start with the 1099 route, but we started with things that were truly 1099. So initially we were selling to small firms for things like making a court appearance or writing a brief or doing work that was truly. You know, not supervised or directed and was for a couple of hours and what was a one-off thing every so often, not more employment like relationships. So initially we started with that and then we did realize that the really big opportunity wasn't the largest law firms that had armies of contract attorneys on staff at any given time, as well as in the in-house legal departments that were starting to use really highly skilled contract attorneys as an alternative to hiring full-time. So what we knew then, and we did actually, of course. Being a lawyer, I did a bunch of research. Then I hired an outside firm to validate my research and make me feel better about my own research. We did see that we wanted to put anybody on site. We needed it to be onsite at a law firm or in-house department. They would have to be W2 and on our payroll as our employee, if they were going to be flexible. Then the other thing is that all law firms and in house legal departments, all of them require. There are temp workforces to beat W2 employees. So they are all very obviously risk averse. There were some big cases. Microsoft got thing for this back in the late eighties, early nineties, there have been other companies that have had major lawsuits, no corporations or law firms want to risk this lawsuit. So they won't allow anybody on their payroll as a temporary worker. Who's not a W2 and they won't work with agencies who are just 1099 and the contractors. So, that was where our clients were always more risk averse. And we had also done a lot of research. So that's where we were ahead of the curve before all these other startups came on board doing 1099. What I do think is really interesting is initially when we were pitching to investors and we would tell them that one of our differentiating factors is that we were W2 and this created a barrier to entry to other startups because it's a huge compliance burden. They all said, this is really boring. This doesn't interest me. VCs will claim that getting sued as a nice to have problem, which is what I heard. A lot in pitches when I was very insistent that this was a prerequisite for a business like ours. So I'm not surprised that all of these VCs funded companies that were out of compliance, because many of the ones that I pitched you were very clear that this didn't interest them and being sued. Wasn't nice to have problems. Joe Taylor: [00:17:56] I want to dig into that a little bit more. So when you hear getting sued as a nice. Staff problem. What do you think they're measuring? What is the success factor that you think they see when a business is getting sued? Because I love spending time with my attorneys, but I love to do it on the back of like signing contracts, not getting sued. Julia Shapiro: [00:18:15] You're one of the few people who says they like to spend time with our attorneys. That's nice to hear Joe Taylor: [00:18:22] It usually means that we're making money. Julia Shapiro: [00:18:25] Exactly. I agree. I like our lawyers, but. I'm also a lawyer. So yes, I think that VCC, it is, if you're getting sued, you're a big company making lots of money and that's when you're a target. VC's like everything in two minute sound bites. So it wasn't interesting to them that the government and the IRS and local authorities have it. Unemployment boards and tax boards. Would go after you, no matter what your size was, they were happy to go after anyone that was too long of an explanation often for VCs to keep their attention. So I think that is part of the reason they funded so many non-compliant businesses. Joe Taylor: [00:18:57] Shifting gears a little bit. Tell me a little bit about the physicality of this. You maintain an office in San Francisco, but you also have presence on the East coast. Tell me why that's advantageous for you having physical space in multiple locations. Julia Shapiro: [00:19:12] So our biggest markets are essentially the greater New York City area, and then way down from Philadelphia, through DC and San Francisco on the West coast. And that's where most of our investors are. And a lot of our relationships and introductions to our clients do come from our investors. So basically it's strategically a sales issue. We need to be in both places. One place is the center of technology. The other place is the center of the legal market. And so it works out well, especially we work with clients in all time zones. So we have clients in a lot of places. We don't have offices, so we have sales resources on both coasts, so we can, everyone can be responsive. Our clients often have fires late at night and want to talk to somebody early in the morning. So we have. Pretty much coverage on all coasts in all time zones with having our two offices across from each other. And then also just being around speak bases of clients and decision makers. You might have a firm that has offices all over the country, but often the decision makers are out of one of the opposites between Boston and DC and our New York office covers all of those areas or are out of San Francisco. That is where the rationale came from having two different offices on two different coasts. Joe Taylor: [00:20:16] A little bit about how that impacted you and your lifestyle. What has. Moving out there done for you that you couldn't necessarily get done in Philadelphia. Julia Shapiro: [00:20:26] So I loved Philadelphia and I really tried to stay there. Although the last two years of my time in Philadelphia, I was in New York more than half the week. Again, that's for investors in our first clients where it took the Philadelphia firms longer to sign on. We have. Lots of Philadelphia firms now, but they waited until we had a strong base of New York and San Francisco firms. So for me, Philadelphia is the great place, but there wasn't both the client interest or the investor interests. So I was in New York often, and then a lot of our investment money did come from the West coast. And a lot of our big clients came from the West coast. So it was natural that I would move out there to be closer to the investors and clients. For me, my life for the past five or six years has been a hundred percent the company. So I didn't really necessarily have a stable life anywhere. I was traveling all the time. I was flying out for the West coast. I was crashing on friend's couches and floors up in New York, just, you know, to save costs. We were pretty, we bootstrapped company and not very well funded company. So for me, moving out to the West coast, at that point, I had given up my apartment, but I had moved in with my sister and her now husband and all of my stuff sit in a couple of boxes. So I was pretty portable and it really wasn't that big of a deal. I shipped my stuff across the country and probably 10 boxes through the post office and found the rent controlled apartment with a roommate and moved in. So it didn't really seem like that big of a deal because my life had been very much dictated by what the company needed over the previous years. Joe Taylor: [00:21:48] And this is very, very different from the typical lifestyle that you hear about an attorney that's on the partner track. Right? So in some ways it sounds a little bit freeing, but tell me a little bit about what do you see for yourself moving forward first off for the company, tell me where you want to see this company in five or 10 years. Julia Shapiro: [00:22:08] We want to take over the market. So the contract attorney market is a $21 billion industry. One in every five legal payroll dollars goes to contract labor in the legal industry. So there's this phenomenon called. The vertical cloud, where if you were the first to market in a specific vertical, or not even the first to market, I should say, if you were the winner of the market, not always first to market, often not you get 50% or more of market share. So our current market of contract labor has not been automated yet. It's very highly fragmented in brick and mortar. We want to be the market winner who takes over more than half of the market. And is the place where people go to build their flexible careers. And we are the go-to place by law firms and in-house legal departments to build their flexible, scalable workforce. Joe Taylor: [00:22:53] Now, do you see yourself establishing more physical presence in other cities, or do you have much more work to do to drill down in the cities that you've got offices in? Julia Shapiro: [00:23:04] So I see us establishing more lean offices as we have now. Coworking spaces are a great thing. Well, both of our offices are self-contained offices within WeWork. So I see us setting up offices where it makes business sense and the way again, office space is scalable now. So it's pretty easy to spin up an office somewhere where you need for client relationship. But right now we. Done an amazing job of servicing the entire country and actually international clients now as well out of two opposites. So I don't see us having a huge need unless there's additional project or very large clients will require that or a new legal center that pops up for growth. Joe Taylor: [00:23:42] So beyond recruiting more talent to work with clients directly, what are some of the roles that you see filling in the organization? Who do you think is the next kind of person that you hire? Julia Shapiro: [00:23:56] Wow. So you kind of hire a little bit of everything at the same time we recently hired an amazing director of operations. So getting a really strong operations hire was key for us at the scaling point that we're at now. I think that for us, it's continuing to build up sales and recruiting resources in tandem because we're a two-sided marketplace and continuing to build out our engineering team. Our engineering team is key to our product and scalability. So we've currently are continuously building out that circle of roles and they tend to, again, go in tandem because the whole marketplace is growing at the same time. You need to hit all of those cylinders. Joe Taylor: [00:24:29] One thing that founders often tell me, is that they'd like to hire for culture. What's the culture that you're building in your organization. How do you know if someone's going to be a good fit to work with you in the clients that you'd like to attract? Julia Shapiro: [00:24:41] I'm getting better at telling what a good hire is. It's a skill you pick up over time and you make a lot of mistakes first. I look for enthusiasm and drive and people that you can tell just like are goal oriented and like to accomplish things. And I also like people that are very curious and we'll just always figure out a way to get things done. I try to ask people questions and figure out if they're somebody that gives up when something is hard or frustrating, I think that's what will kill you at a start up if you hire people like that. You need people that are very autonomous and have a very can-do attitude and won't sleep until they figure things out. So that is what I have grown to look for. And we have enough people. Most of our team now is like that. So you start to recognize it once you've built a team like that. Joe Taylor: [00:25:22] I think you're bringing up a great question. And the kind of thing that you often hear asked on an interview is tell me one mistake that you made early on in building the company and how you overcame it. How did you come back from it? Julia Shapiro: [00:25:34] Oh, there are so many, it's hard to think of, like, just one. I think that part of it being an entrepreneur is failing a lot and not giving up. And I think that's the difference. You will succeed. If you hang in there long enough, you just have to decide what your stopping point is and what your values are. And what's too much. So I made so many mistakes. I do think that not knowing how to hire right. Having no context, never having hired people before was probably. The biggest mistake we had to correct it overcome. And it's interesting because you need different types of people at different stages of the company. So somebody that's a really good stage, really good at one stage of a company who really likes the, kind of like, the chaos and figuring things out and making lots of connections is probably not the right person when things get a little bit more organized and orderly and there's more processes in place. So I think that probably. The wrong hires at the wrong time was probably, I would say the biggest mistake I've made overall. Joe Taylor: [00:26:27] I think that brings up another great thing that happens with entrepreneurs is that we evolve so much over time. So tell me about what you are looking forward to solving in the business over the next five years. What's the challenge that you're really excited to tackle next. Julia Shapiro: [00:26:44] I'm really excited to tackle. Really good culture fit and skills fit. So some of the technology we're building out now. Helps to not just play somebody in a job. One thing that universally frustrates people about recruiting, as they try to just sell a candidate, you know, I have a candidate, I have a slot to fill. I'm going to just try to get this done and not necessarily care about the match. It's just important to get the job done, not the best way. So what I'm most excited about tackling in the future is. Really good fit and really good automated fit that takes out biases and prejudice from the recruiting matching process. So we're working on algorithms that basically track how people work through our system and track what's our recruiting agencies like on an objective basis, and then making matches based on those factors instead of a recruiter, opinions or biases. And this makes the product truly on demand too. So that. It's like Netflix or Amazon, where, when you log into your Amazon account or your Netflix account, the computer's telling you what you needed or what you wanted before you knew it, or is picking out the right things for you based on your, you know, your profile and what you need. So that's what we're really excited about building out in the future. Joe Taylor: [00:27:58] Fantastic. What else should we know about Hire an Esquire before we wrap up the broadcast today? Julia Shapiro: [00:28:04] That we are growing very quickly and we're always building on our internal team. And if you are an attorney, that's looking for a more flexible lifestyle, we encourage you to check us out. And if you're a law firm, that's looking for a way to be more scalable and whether the economic cycles, you should also check us out. Joe Taylor: [00:28:21] Fantastic. Julie Shapiro, founder, and CEO of Hire an Esquire. Thanks for stopping by The Build. Julia Shapiro: [00:28:27] Thanks again for having me on the show. Announcer: [00:28:29] Thanks for listening to this episode of the build. We hope you'll share this series with your friends and provide us with feedback on the iTunes store. This has been a two eight 20 radio production. Joe Taylor: [00:28:51] The Build is a production of 2820 radio in Philadelphia. Our producer is Katie Cohen Zahnister and our consulting producer is Lori Taylor. Talent coordinator is Katrina Smith. Our research team includes Alison Hartman, Fianna Seeney and Gizzem Yali. Our post-production team is led by Evan Wilder at FlowlyAudio in Detroit. My name is Joe Taylor Jr. Thanks for listening to The Build.