What’s it like to take evening classes while working full time to expand your career options? In this episode of Career Relaunch, David Gulbransen, a former Software Startup Founder & IT Consultant turned Intellectual Property Attorney & Director of IT shares his thoughts on attending law school while holding down a full-time job, managing failure, and creating a diverse, portfolio career.  I also share some thoughts on the importance of investing in yourself.

Key Career Insights

  1. Returning to school to pursue an additional degree is a major investment of time, money, and energy. However, it absolutely can be worth that investment, especially when it opens up new opportunities to diversify your career and feed all your interests.
  2. Experimenting and exploring many options can help you gain clarity about what your true passions are.
  3. If you have a unique product, service, or technique you’re developing, you should take the time up front to connect with an IP lawyer to consider securing a trademark or patent.
  4. Investing in yourself to learn a new skill can be an incredibly powerful catalyst to creating change in your career.

Tweetables to Share



Resources Mentioned

  • David talked about the importance of Patents & Trademarks, especially if you’re a small business owner developing an idea, product, or service.
  • Here’s more information about Trademarks from Trademark Direct, a service I’ve used myself. You can also do a quick Trademark search yourself on Trademarkia to see if the name you’re considering is available.
  • The US Patent & Trademark Office has some pretty good articles on Intellectual Property, where you can read about Patents, Trademarks, Servicemarks, and Copyrights.

Free Tool: Investing in Yourself

Mental FuelDuring this episode’s Mental Fuel segment, I talked about the importance of investing in yourself. For some help in doing this, you can download my “Investing in Yourself” Worksheet.

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About David Gulbransen, Intellectual Property Attorney

David Gulbransen HeadshotDavid Gulbransen is a author, attorney and “IT” guy based in Chicago, Illinois. In his law practice he focuses on intellectual property issues (copyright, trademark) as well as information technology and business law, primarily with startups and small business entities. He’s also the Director of IT at the University of Chicago Law School. David had over a decade of experience in information technology and software development and is a published author with over half-dozen technical books under his name. Currently, he contributes a regular technology column to the Chicago Daily Law Bulletin.

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Episode Interview Transcript

Teaser (first ~15s): It was just a very unique opportunity that presented itself, a natural and very good fit for my particular experience, sort of an alignment of the stars if you will.

Joseph: Hello, David. Thanks so much for joining us today on Career Relaunch. I am really looking forward to hearing all about your career story.

David: Great, I’m happy to be here.

Joseph: I’d love to start off by, first of all, having you just tell us a little bit more about your law practice and also the work you do at the University of Chicago Law School.

David: My law practice is primarily concentrated in intellectual property. I practice part-time because I am also at the University of Chicago Law School. My role there is as the Chief Information Officer, so I’m in charge of the IT for the school, both from a policy perspective and overseeing the technical staff here at the school.

Joseph: I see. On the intellectual property side, do you work with any particular type of clients or any particular type of business?

David: I tend to focus on small businesses and startups. I have a background in computer science and a lot of experience with startups actually before I became an attorney. I really like working with small business owners or people who are in the very early stages of startup venture, trying to get things off the ground, don’t necessarily have a lot of money or funding but still have legal questions and legal issues that they need to address to make sure that they’re in the best position possible down the road when they do start either growing their business or receiving funding to grow their business.

Joseph: I definitely want to come back to that because I think there’s a lot of interesting tips and lessons that we can definitely learn from you. I’m actually most interested, since we are here to talk about career, in hearing a little bit more about your career trajectory, because obviously, having a law practice and being the director of IT are two very different things. You got the true portfolio career. I’d love to go back in time and just have you take us through how you got to where you are right now. Can you explain to us what you were doing before you became an attorney, when you were involved in web development?

David: I graduated from college with a degree in Computer Science, and so after that, I needed a job, and it was in the mid ‘90s. It was a very good time in the US in the tech industry, and so I actually went to San Francisco and worked for a startup there. After that startup was acquired, I launched another startup. I was mostly doing technical development work, XML, Java development.

I really enjoyed working in the startup environment. I enjoyed the culture, the pace. Everything about it was really great, but I realized that the things that I was interested in relating to startups were less development, less technical and more the business side of the house, more financing, management, growing the business, attracting investment, that sort of thing.

Joseph: So what happened after that? Did you continue to do what you were doing or did you make a move into the business side of things?

David: I started to make a move more into the business side of things with my own startup, which was an XML development company. I enjoyed having my own startup, but I really liked the people that I met at other startups and talking to them and wanted to figure out what way I could work with other entrepreneurs in a way that I could add value to the businesses that they were creating, which led be to a decision point where I thought about pursuing an MBA, and I thought about pursuing a JD.

My wife was an attorney. We sat down, and we had this discussion. Basically, it came down to the single question of, what can you do with one degree that you can’t do with the other? Although the education track is somewhat different for the two obviously, with an MBA, you could do everything that you could with a JD, except practice law, and the converse is not true. With the JD, you could do everything you could do with an MBA, but you also have the option of practicing law.

I’ve always been interested in intellectual property, especially as it relates to software development and tech companies. Obviously, with any kind of tech startup, there’s a large intellectual property component, and so that led me back to law school. I decided to go ahead and pursue my JD with a certification in intellectual property.

Joseph: What was that process like, David, as you were thinking about the prospect of going back to law school, having already worked for so many years? What was that like for you?

David: It was daunting really. I mean I was a non-traditional returning student, so I was older than most of my classmates. I had a job at the time. I was working at the University of Chicago Booth School of Business in the IT department as the director there, and so I had to return in an evening weekend program, which is a little bit longer than a traditional law school program. Going to school period is a challenging thing. It takes a lot of time and energy. Doing that on top of working a full-time job was really daunting.

Joseph: How different was the type of work you were needing to do in law school versus the type of work you were doing before? Obviously, you were a student, which is different, but I would imagine the way you use your brain is radically different.

David: It really is. It’s kind of cliché, but the saying is that law school doesn’t teach you the law. It teaches you how to think like a lawyer. Like most clichés, there’s an underlying element of truth to it, and it’s a very different skillset that you’re applying. There’s a similarity in that a lot of law, at least in practice, is problem solving, and a lot of IT is problem solving, and so there is some overlap I find there to approaching how to solve a problem, but that’s really where the similarity ends.

Joseph: I see. During that process, did you ever have one of those moments where you just thought, ‘Am I on the right track here?’

David: Sure, there were plenty of times when I thought, ‘Why am I doing this?’

Joseph: I can imagine.

David: ‘Can I sustain this?’ going to work from 9:00 to 5:00 and then a half-hour break and then classes until 9:00 p.m. four nights a week. There were definitely times when I questioned whether I was doing the right thing or not or whether or not I could keep up with it.

I think what really kept me going was my wife was very supportive. She had gone through a similar program. Not only did she understand the perspective of what I was going through as a law student because she had done it before, but she understood the additional challenge of being a non-traditional evening weekend law student, which is different than the challenges that a full-time law student faces.

Joseph: Could you also just take us through or give us a glimpse into what it was like to be a slightly older student in law school? Because I know some people I talk to, they realize that they need to go back to school to get to where they want to go, but the idea of going back as an older student is one that they struggle to reconcile. Could you just give us a glimpse into what that was like for you?

David: Actually, I liked it for a couple of reasons. One, most of my peers when I was in law school had full-time jobs, had families, and so they understood sacrifices that we were all making to be there, and they understood the difficulty of managing the workload from your primary day job in addition to the workload for school. I think you get a lot of support from your fellow students, which is nice.

The other thing that I think is a little bit different is I knew I wanted to be there to pursue a JD. I wasn’t there because of family pressure to continue in the family business. I wasn’t there because I had just graduated from college and didn’t know what else to do. I had a much better focus, I think, than I would’ve had when I was younger.

Joseph: You had a lot of experience before in the IT industry. What happened to that part of yourself when you made the shift toward pursuing law?

David: I focused my classes on intellectual property, on trade secrets, copyright law, patent law, and in those courses, I think having a technical background definitely helped and contributed to the subject matter because so much of the tech industry has intellectual property as a major component, and so it was definitely helpful to have that background.

I found that in those intellectual property classes, the majority of students had some kind of technical background. It wasn’t necessarily computer science, but it may be that they were electrical engineers, mechanical engineers, or chemists, biologists, people that were coming from some kind of science, technical background because that’s a big help when you’re pursuing a career in intellectual property law.

Joseph: What’s interesting, as I’m listening to your story here, David, is that you seemed to have this very strong clarity. I know you mentioned there were some doubts along the way, but you seemed very certain of where you’re headed and what you wanted to do. How did you get that clarity? Because I talk to a lot of people, when they’re thinking about making a change, one of the biggest fears is knowing whether or not that’s the right move and the fear that they’re going to end up in a situation that maybe isn’t any better than where they were before. How did you amass that or cultivate that clarity?

David: Part of that is that I frequently experiment with other things. I pursue lots of hobbies in my spare time, and so I explored different options along the way. In addition to my background in computer science, I have a background in theater.

Joseph: I saw that. You deal with the green computer science and theater.

David: My undergraduate degree added scenic design. I was a designer, not an actor. I pursued that for a while. I actually, for a while after college, had my own production company that did video production. I explored that career option. It didn’t work out. It turned out not to be for me.

At least for me, I had to go through a period of trying different things and not being afraid to fail. It’s hard. I think everybody is afraid to fail, and I was certainly afraid to fail, but I did fail. I had startups that didn’t pan out. That teaches you some valuable lessons, I think, about your interests, where they lie, what you’re capable of, and I hate to say I recommend everyone to fail—it sounds weird to say that—but I do because I think that one of the best lesson that I learned from failing in a startup environment is the lesson that it’s okay, and life goes on. You can pick yourself up, dust yourself off, and try something else.

The world doesn’t stop, and it’s not the end of everything if you do fail. Life is full of second chances, and so if you try something, and it doesn’t work out and it fails, try to look at it, learn the lessons from that failure, and then take those lessons into the next thing that you try.

Joseph: As you think about this transition, David, what do you think was the hardest part of making the shift from one industry into another?

David: The hardest thing for me personally was that I wasn’t actually sure if I wanted to practice law. I had a very clear vision of what I wanted to do with my law degree – advising startups and dealing with intellectual property. The absolute thing that I did not want to do, which I saw some of my peers having to do, is end up doing insurance defense of get trapped into a large firm where, all day long, you’re reviewing documents and supervising other people reviewing documents. Those are things that I definitely knew I didn’t want to do, and frankly, that’s the majority of stuff out there practicing law.

Eighty-five or ninety percent of it are things that I didn’t want to do. I didn’t want to litigate, I didn’t want to do criminal law, and so it seemed like it was a big leap of faith to pursue this degree with the end goal being the ability to practice law, knowing that the majority of types of practice out there I didn’t want to do.

Joseph: Finding the needle in the haystack there.

David: Right, the very particular niche market that I wanted to be in.

Joseph: So you finish up law school, and then what happens? Obviously, you decided not to go work for a firm. How did you then come to the decision that you wanted to start your own practice?

David: I’ve always been very independent and comfortable with the startup aspect of it, and so I launched my practice immediately after law school. I spent about two years doing consulting/legal work while I started to build clientele with my practice because I always had the IT side of things, which has sort of always been my safety net. I was able to take on a mixture of IT consulting clients and legal clients. It allowed me to not handle a divorce case when somebody would ask me for it.

That, honestly, was one of the hardest things to avoid when I started my own practice: you don’t have a deep base of clients, so there’s always this temptation to take anyone who walks in the door because you need the work, and you think, ‘I could just do this one divorce because I don’t have any IT clients lined up right at the moment, and I don’t have good prospects. This is right here, and it’s pay.’

Joseph: How did you avoid that temptation?

David: I took a divorce case. It was awful. It was so awful. It was absolutely horrible. It just wasn’t worth it if you know the tradeoff of the potential money from that type of work versus how much I disliked the work. If I wanted to keep doing work that I didn’t want to do, I could have not wasted that much time and effort. That helps bring it into very clear focus.

Joseph: In addition to focusing on the legal work you do enjoy, if that weren’t keeping you busy enough, you’re also the Director of IT at the University of Chicago Law School. Can you just walk us through how you came to that decision to add another layer to your career to make it a true portfolio career?

David: It was just a very unique opportunity that presented itself. I was practicing. I had a lot of experience in IT in the university setting. I worked for the University of Chicago Booth School of Business for eight years, so I had a lot of experience with the institution, I had a lot of experience in the academic computing, and so when the position at the law school presented itself, it was a natural and very good fit for my particular experience. I had university experience, I had IT experience, and I had a law degree. It was just sort of an alignment of the stars if you will.

My practice is very small. Again, it’s part-time. I deal primarily with very small startups and small businesses. The nice thing about it was that it’s not full-time, so I can do it part-time outside of regular working hours here at the university. That allows me to be very selective about my client base, which is something that is very, very fortunate.

Joseph: When you look back at all your career changes, what’s something that you wished you had known that you now know about career change?

David: I wish I had known how much work it is. I think I did go into law school a little bit blind to how difficult it is to sort of completely swivel. It’s hard. Going back and pursuing additional education is hard. It’s a big time investment, and I don’t think I fully understood how much of a time commitment that is. Again, I think that, sometimes, you just have to take that leap of faith and not be afraid to fail.

Joseph: If anybody out there wants to change careers and become a lawyer or get into the legal profession, do you have any advice?

David: I love education, and I recommend more education for everyone, but you do have to look at the return on that investment. Law school is not cheap, either is business school, and so you really have to understand the value of what you’re paying for and the prospects for the return on that investment to obtain that JD.

There are great things that you can do with a law degree that are rewarding in non-financial ways. I know a number of students, people that I went to law school with, who are working in public interest, who are working in immigration law and who are not getting rich doing it but are really, really making a difference in people’s lives. There are non-monetary returns that you have to weigh into that calculation.

Joseph: Now, I can’t let you go without talking a little bit about your expertise, which is intellectual property. Do you have any intellectual property tips for small business owners, whether it’s just a common pitfall that comes up that you deal with or just a general piece of advice that you think is helpful to share?

David: Two things that I see happen a lot are patent law and trademark law. In patent law, the number one thing that comes up is, ‘I have this great idea. I’ve been selling this product for a couple of years, and now I want to see about getting it patented.’ There’s a statutory one-year bar on patents once you started selling your product.

If you have a physical invention or if you have a process that you think is very unique, any kind of invention like that that you think may be patentable, talk to a patent attorney or a patent agent as quickly as possible. End up saving yourself money in the long run by spending a little bit of money upfront to figure out whether or not you have a patent.

The other mistake that I see people make is with relation to trademarks. That is, ‘I launched this great company, and it’s going really great, and I’m selling it. Then I just got this letter from this other company that says that I’m infringing their trademark. What is this?’ It’s a lot better to pay a small amount of money to an attorney to do a search and make sure there are no conflicting trademarks out there and to register your trademark upfront than it is to be selling your product and developing your brand for three years only to get hit with a cease and desist and find out that you now have to start over again from square one.

Joseph: I can definitely attest to the importance of speaking to an attorney about your trademark. When I started my business, I called it Onward Coaching, which I thought was so cool, and I was really excited about the name because it was aspirational and it was all about moving on in your career. It wasn’t until I actually talked to a trademark attorney that I realized I couldn’t actually trademark that name because it violated one of the criteria for a trademark.

I know that whenever I talk to legal experts like you, I end up learning about a lot of things that never even cross my mind to consider. So I think that’s valuable advice.

If people want to either learn more about intellectual property law or if they just want to have a chat with your or find out more about the work you do, where can they go?

David: They can go to my website, which is just GulbransenLaw.com.

Joseph: Thank you so much for your time today, David, sharing your story about your portfolio career that you developed for yourself, the importance of learning from failure, and also just sharing a few useful tips about getting into the legal profession but also some tips on intellectual property law too. Thank you so much for your time.

David: No problem. It’s been fun.

About Joseph Liu

Joseph Liu is dedicated to helping people relaunch their careers and have more meaningful careers. As a public speaker, career consultant, and host of the Career Relaunch® podcast, he shares insights from relaunching global consumer brands to empower professionals to more effectively marketing their personal brands.

About Joseph Liu

Joseph Liu helps aspiring professionals relaunch their careers to do work that matters. As a keynote speaker, career & personal branding consultant, and host of the Career Relaunch podcast, his passion is helping people gain the clarity, confidence, and courage to pursue truly meaningful careers. Having gone through three major career changes himself, he now shares insights from building & relaunching global consumer brands to empower professionals and business owners to build & relaunch their personal brands.