Book It Legal

From Lawyer to Legal Tech Founder: How Jack West Harnessed Student Power.

Happy to announce our second founder for the MyShingle profile series, Jack West of BookIt Legal. From Lawyer to Legal Tech Founder. As I mentioned last week , we’ll be profiling lawyers starting businesses in the legal tech space – with a specific emphasis on companies that at least in some way, serve solo and small firms (in other words, no enterprise-scale e-discovery software or products priced out of solo and small firm range).  BookIt fits well within this category of tech founders, because the company provides low cost outsourced legal research and support provided by law students. Thus, BookIt is a convenient and affordable option even for the newest solos by giving them some needed help as well as an opportunity to train the next generation of lawyers.  Jack doesn’t come from a legal tech background – which he admitted was an obstacle, albeit not an insurmountable one.


Money Quote: Your lawyer brain may tell you, “this is a big risk, you shouldn’t take this risk,” but no company ever succeeds without a healthy amount of risk-taking.


What’s your name, and your company? I’m Jack West, theFounder and CEO of Book-It Legal. You can also find me on Facebook at and Twitter at @bookitlegal.

Tell us a little bit about your company in a nutshell: Book-It Legal’s online platform gives attorneys access to a pool of top law students across the country for help with research, editing, document review, articles, and more. Attorneys name the price they are willing to pay to have a job performed, receive applications from interested students, and select the best candidates for their particular projects.

Prior to your current position at your company, how long did you practice law and where? What was your area of practice? 

Before starting Book-It Legal I practiced for three years with a mid-sized civil defense firm. My practice focused on transactional corporate and securities work, although I also was exposed to tax, real estate, corporate investigations, and some litigation matters. The skills I gained while in practice have certainly helped me as I transitioned into founding a company.

What gave you the idea for Book-It Legal?

The idea for Book-It Legal came to me when a partner dropped by my office and asked if I could help edit a brief he was about to file. Our summer clerks had just left to go back to school, and as I spent a few hours polishing the brief I thought, “this would have been a great project to delegate to a clerk, and I actually could have done some of this cite-checking and shepardizing more efficiently back when I was a student. Wouldn’t it be nice if there were a way to quickly get a student working on a project for me whenever the need arises.” It would free me up to do higher-level work, and it would have the added advantage of allowing the firm to get to know a student’s work prior to inviting the student to join the full summer program.

Right now, many firms invite summer clerks based on a one-page resume and a short interview. If there were an easy way to vet students and pay them to do smaller projects so as to get to know their work product before hiring full-time, that would be valuable.

And, of course, as a law student I would have loved to be able to pick up projects from a variety of lawyers in different areas of the country to gain experience, build up the resume, and earn some income. Most opportunities I saw posted through job boards were looking for a part-time clerk to work 15-20 hours per week, and I couldn’t make that commitment with a busy academic schedule. But I sure would have signed up for projects when my schedule allowed.

Also, many students are trying to find employment in legal markets outside of the states where they attend law school, and it can be difficult to build a network and find a job in another market when you’re attending school across the country. One goal with Book-It Legal is to help students pick up projects in markets where they have an interest in working after graduation to get that first piece of experience on the resume linked to a particular locale and to network with attorneys there who might have a hiring need down the road.

So let’s talk about how you moved your idea to implementation.  After you came up with the idea for Book-It, did you take steps to validate it? And second, after you decided to go forward with Book-It, how did you find developers and how long did it take to get the site up and running?

After having the initial idea I began doing some market research to see what services already existed and found a few services connecting firms with freelance or contract attorneys and with paralegals, but I didn’t find anything available for students.

The early validation steps were comprised of talking to attorneys and figuring out exactly which segments of lawyers would find our platform valuable and what types of projects they want to get off their plates and delegate to students. I did interviews with something like 50 lawyers from various backgrounds and practice areas (small firm, big firm, in-house, government) and gathered data on who had the greatest needs and would receive the most benefit from an on-demand law clerk service. Those interviews also informed what features we built (and did not build) into our early system.

As you might expect, solos and small firms without support staff have the largest need, and that’s a large market. But one thing those initial interviews revealed that I didn’t think of at the outset is that in-house lawyers at small and medium-sized companies are often drowning in work and could use an affordable outsourcing option. Most don’t have a mainline to students but do have small projects that don’t necessarily require the attention of outside counsel.

As for the types of projects attorneys want to delegate, of course, research memos are common, as well as brief-editing and document review. One task that was mentioned frequently was having students write blog posts or short articles on legal topics, and we’ve certainly seen demand for those types of jobs since we launched.

As for learning about tech, finding web developers, and getting our initial product built—I won’t lie, it was a challenge, though not an insurmountable one. Prior to leaving traditional practice, I had zero experience with tech. Zero. So I had to begin educating myself about the software development process and meeting web developers. I knew exactly one person who was in tech and had done a startup and was willing to help me. He happened to be a good friend from college. I called him up and began picking his brain about how to turn my idea into a reality and asked him to help me vet developers. He very generously pointed me to resources so that I could start learning how to speak to developers and not appear totally clueless.

I also took a few basic HTML/CSS coding courses online and read a few books so that I would have a foundation to understand software development. It’s certainly easier to attract higher-level talent if you know enough to be dangerous.

I also started getting plugged into the local startup and tech scene by going to meetups, sometimes those just for developers. I might go to an open source software meetup and barely be able to follow the discussion, but I would learn something new and meet a few people, some of whom were interested in discussing my idea and wanted to help.

How long has Book-It Legal been in operation, and what has the response been so far?

It took me about seven months to go from “I just left my job and don’t know who is going to help me build this” to having a functioning beta that we could use to start signing up attorneys and students. We were in beta for about four months improving the site, de-bugging, and responding to early user feedback.

We went into full release almost a year ago and now have students from 25 schools and attorneys from 15 states using the platform.

So let’s talk about your product. In your view, what gap does Book-It Legal fill in the market?

I may have covered some of this above, but for attorneys, Book-It Legal fills the need of having an affordable, go-to outsourcing option for smaller projects. We give them an easy way to leverage a pool of great students when the workload heats up.

For students, it satisfies the need for a flexible way to pick up work during the school year or during holiday break or between clerkships. We see attorneys repeatedly working with the same students on projects and expect the relationships that begin through our system will evolve into full-time employment after graduation.

Unlike other freelancer platforms (which are providing excellent services for other levels of work), Book-It Legal is centered around the lawyer/law student relationship. While it’s a narrower market, choosing to concentrate on this relationship has given us focus and a clear purpose: improving opportunities for law students.

What are your goals for Book It Legal? Where would you like the company to be three years from now?

Our goal is to be connecting students from every law school with attorneys in every state and creating more work and educational opportunities. We have other ideas about how to supplement legal education and job outcomes, and you may see us roll out a complimentary product in 2018.

Now that Book-It Legal is up and running, what is your day to day role in the company? Can you describe a typical day (if there is such a thing?)

Ha! No such thing. I may be speaking at a bar event or CLE, reviewing new features of the software before we roll them out, talking to companies we may want to partner with, working on company financials, analyzing metrics, responding to user support requests, drafting marketing material, applying for startup competitions.

How does your training and experience as a lawyer help you in running your company?

Yes, immensely. Since I did transactional work I had dealt with entity formation, business licenses, tax issues, NDA’s, contractor agreements, some accounting issues, all of which your startup small-business owner has to deal with.

But thinking like a risk-averse lawyer can also be a hindrance when starting a tech company. We’re trained to help clients avoid and mitigate risk. We’ve read so many cases about how things go wrong and can become such hardened skeptics that it can be difficult to see how a new venture might succeed. You have to see a path to success and hold onto it.

Sometimes there’s risk, no way around it, and you have to take the risk. Your lawyer brain may tell you, “this is a big risk, you shouldn’t take this risk,” but no company ever succeeds without a healthy amount of risk-taking.

Do you think that coding experience is beneficial to lawyers who want to start a legal tech company? What skills do you think are most important?

It sure doesn’t hurt. I think a baseline of knowledge is necessary, but unless you plan to build the product yourself, actual coding experience is not necessary. As I mentioned, I did take some basic, free, online coding classes, which were helpful, but the purpose for me was to be able to talk to recruit good developers, not to be able to build our product.

Your time and skillset is likely better spent on other activities, like making sure there’s a market for what you’re building, finding early customers, and getting your company’s name out there.

Now if a lawyer gets really into coding, then soak it up. An attorney with real technical chops is a person to be reckoned with.

What are some of the differences between running a tech start up and running a law firm (or working at a firm)?

I worked as an associate, so I can’t speak to the trials and tribulations of running a firm. But running a startup is a whirlwind, and being able to identify and hone in on the central items that will advance your company when there are a million other things coming at you is important.

What was the biggest challenge for you in transitioning from law practice to your current position?

Everything. At first, it was learning about how software is built and finding developers. Now it’s learning how to market effectively—not something most of us are taught in law school or in practice.

Do you miss practicing law?  What have you done, if anything, to keep your law license and legal skills intact?

Sometimes, but I’m glad I took the leap. I’ve kept my license active, though I don’t represent clients. One thing I’ve enjoyed since leaving traditional practice is being more active in bar associations. As a young associate trying to bill hours, I didn’t attend as many bar events as I get to now. And my CLE credit hours are through the roof!

Something I did recently that helped keep my legal skills in tact was participate in an experiment run by Lawgeex where they asked attorneys to identify issues in NDA’s to compare against their software. A fun, practical exercise. Did I beat the machines? Probably not.

Do you have any formal training in technology or “hot” technical skills (e.g., programming, product development, data science) and are these skills necessary to build your company?

Nope. Those skills are certainly necessary to build a tech product, but finding others who are more skilled in those areas may be a better use of your time than trying to acquire the skillset yourself.

If another lawyer was interested in starting a tech company, what advice would you have?

Start learning about software development, talking to developers, and figuring out who is going to help you build it if you can’t do it yourself. Simultaneously, talk to the people you think need or will use your product. Collect data from them to learn about who your target users will be.

It may seem counterintuitive, but if you can sell your product before you’ve even built it, you’re probably onto something. Some companies can get pre-orders and essentially have their early users finance the cost of building the product, which is amazing. If you can do this, your company stands a good shot of making it.

At the very minimum, have a sizable list of people who want to be early beta testers for you and express interest in become paying customers.

Whatever you do, don’t go build something in the dark thinking that people will flock to it once you unveil it to the world. You might spend a lot of time and money building a product no one wants. I would rather see significant “customer discovery” than a beautiful product with nobody lined up to use it.

In general, though, my advice would be to go for it. Take the leap. Even if the company doesn’t make it, you’ll learn so much and meet so many new people and have so much fun in the process that it won’t matter.

Imagine a future where you don’t go for it, where you stay at your job and watch as another lawyer with the same idea comes along and builds a great company out of it. How painful would that be? How much would you regret not having done it?

What excites you most about the future of legal technology?

Bringing more legal tech into legal education excites me, whether that’s online course content, student/lawyer collaboration tools, facilitating pro bono opportunities, or using AR/VR in the classroom to teach trial skills. Today’s students are going to drive legal tech tomorrow, so let’s give them some new tools.

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