To say that Liz Oliner is busy would be an understatement. Not only is she an avid yogi, skier, cyclist and runner who has completed eight marathons, but she’s also the mother of a two-year-old son.

Somehow, between all of these pursuits, Liz finds the time to run her own successful law practice as a freelance trademark attorney. She has completed nearly 1,000 projects on UpCounsel and has served clients such as AngelPad, Plug and Play Tech Center, Women Who Code, Soldsie and even UpCounsel itself.

Liz took time out of her full schedule to chat with me about her unique path to becoming a freelance attorney and the valuable lessons she’s learned along the way.

You graduated college in 2000, but didn’t go to law school until 2007. What did you do in the interim?

I had a few different jobs. I was a journalist at CBS news, and later worked at a research institute run at NYU School of Law. I also worked in commercial real estate.

I was just trying to find a career, but neither television journalism nor real estate spoke to me. I wasn’t finding my real passion.

What made you decide to go to law school?

I still wasn’t sure what I wanted to do when I applied, but I figured that having a law degree wouldn’t hurt. I was working in real estate at the time I applied and I assumed that I would go into real estate law and work with a developer, or do something with commercial leasing.

Why didn’t that plan pan out?

Right when I graduated law school, the real estate market collapsed. There were no jobs in real estate.

“I help people launch and protect their brands, and that’s an exciting time for businesses.”

[tweetthis]”I help people launch and protect their brands, and that’s an exciting time for businesses.”[/tweetthis]

That must have been unsettling. How did you shift your focus so that you could succeed in the new economy?

I actually moved from New York to San Francisco somewhat randomly, and without a job lined up. When I arrived in San Francisco, I decided to apply for a job at a small law firm as a trademark attorney. It seemed like a good fit because I had taken a lot of trademark law classes and had interned in the trademark department at Estée Lauder during my last year of law school.

As a trademark attorney at a small firm, I finally found my passion. I focused on trademark prosecution and helped small and midsize businesses conduct risk assessment, file and monitor trademarks and navigate the USPTO.

What do you like about helping businesses secure trademarks?

I like that it’s a really niche practice, and one that many corporate attorneys don’t focus on. Many corporate attorneys seem know just enough about trademark law to be dangerous but not the ins and outs of dealing with the trademark office. It’s a real speciality, and even now I talk to other attorneys who want help understanding the process.

I also like that there’s nothing particularly depressing about the kind of law that I’m doing. I help people launch and protect their brands, and that’s an exciting time for businesses.

What’s challenging about practicing trademark law?

One challenge is that it involves managing many clients and many deadlines at the same time, rather than just focusing one large project. Other challenges come in the form of opposition that my smaller clients face from larger companies. They send my clients cease and desist letters, and sometimes it’s very clear that their goal is not to be nice about it. They can be bullying and aggressive.

How do you deal with a large company accusing your client of trademark infringement?

Thankfully, I have experience that allows me to see the issue from both sides. After working with small businesses for several years, I became a trademark enforcement attorney for Brown-Forman, the company that owns the rights to Jack Daniels, Finlandia Vodka and other liquor brands.

“As a trademark attorney at a small firm, I finally found my passion.”

[tweetthis]”As a trademark attorney at a small firm, I finally found my passion.”[/tweetthis]

Everyone uses the Jack Daniels logo without permission on all kinds of merchandise. The company definitely responds and tries to enforce their trademark, but they’re generally nice about it.

It was really interesting for me to see the issue of trademark infringement from the perspective of both the small company accused of trademark infringement and the large company protecting its famous brand. I like to think that having been on both sides gives me a competitive edge.

How did your experiences working with small businesses prepare you to run your own firm?

I’ve worked at two small firms over the course of my career. When I say small, I really mean it – one firm had ten attorneys, and the other had three.

Working at small firms helped me understand how to run a business. I had to deal with finding and managing clients, and that taught me how to handle a variety of issues. For example, how do you collect money from a client who’s reluctant to pay?

Had I worked at a large firm, I wouldn’t have gotten that experience. There’s so much bureaucracy in biglaw, so young associates rarely have to source clients, have very direct client contact or even learn simple things like how to send invoices

Dealing directly with clients also enabled me to develop relationships with them. In several cases, when I left the firm, they contacted me directly asking where I had gone. They liked working with me and didn’t want to work with the new person who had replaced me.

Those clients inspired me to start my own firm. At first, I only had three clients, each with a fairly low legal spend. Even so, I stuck with them and decided to see how it went. I guess it went well because I never looked back. I never took a job at a law firm again.

What are the benefits of running your own practice?

First, you have a lot more flexibility. You are your own boss, so you can make decisions for yourself.

That means choosing which clients you want to work with, setting your own hours and scheduling your own vacation time. I have a two year old son, and that flexibility has been really helpful whenever our nanny is sick.

When you don’t have a boss, you also don’t have to deal with office politics. My office is me and the paralegal who I work with, and he’s also very easy-going.

“Specialize in something, if you can. It’s more efficient than trying to do it all.”

[tweetthis]”Specialize in something, if you can. It’s more efficient than trying to do it all.”[/tweetthis]

What are some of the challenges you face as a freelance attorney?

Having your own practice is not completely stable. Business ebbs and flows. Sometimes I’m so busy that I feel completely overwhelmed, and sometimes business is slower for months at a time. It can be nerve wracking to have no idea how business will be in any given month.

I was concerned also about not having enough mentorship, especially when I first struck out on my own. Mentorship is something that you would get at a law firm or as part of an in-house legal team, but not as much as a freelance attorney.

How did you go about solving this challenge?

I continued working for Brown-Forman as a contract attorney for several years after starting my own practice because the work gave me access to more senior lawyers. It was invaluable to get their opinions and insights whenever I was facing a difficult situation with a client or had a substantive question.

Establishing relationships with other attorneys who have related practices is also really helpful. I can call or email them to talk about whatever is confusing to me.

For example, although I feel very confident in my ability to handle trademark prosecution, I have less experience with litigation. When a litigation matter arises, my relationships with other attorneys allow me to get the advice I need.

How did you develop those relationships?

Some of my connections are friends from law school, but I’ve also attended networking events and conferences and joined professional groups.

What advice would you give other attorneys who are considering starting their own practice?

First, specialize in something, if you can. That’s a lot more efficient for both you and your clients than trying to do it all

“If you’re thinking about starting your own practice, you should just take the leap and go for it.”

[tweetthis]”If you’re thinking about starting your own practice, you should just take the leap and go for it.”[/tweetthis]

I learned that through experience. When I first started freelancing, I would do pretty much anything anyone asked me to do. For example, if a client asked me if I would file a corporate entity, I’d reply “Sure I will!”

Now, I don’t do that. It’s not that I can’t file corporate entities – I can and I have. But it takes me so long to do it that it’s not worth my time. The client would also be better served going to an attorney who does that kind of work regularly.

Additionally, lawyers are very risk-averse by nature. But if you’re thinking about starting your own practice, you should just take the leap and go for it. If you don’t try, there’s no way you can succeed.

About Liz Oliner

Liz Oliner is a native New Yorker who moved to the west coast after law school and now lives in San Francisco. Liz has a B.A. in English literature from Yale and a J.D. from Yeshiva University Benjamin N. Cardozo School of Law.

She is an expert at navigating the USPTO and has helped hundreds of small businesses and entrepreneurs register their trademarks and protect their brands. She filed over 300 trademarks in the last year alone.

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About the author

Ariel Shultz

Ariel Shultz

Ariel manages the attorney community at UpCounsel, where she focuses on helping attorneys find success and grow their practices. A former practicing lawyer herself, she understands the challenges facing attorneys and prioritizes making the UpCounsel attorney experience exceptional.

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