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Keren de Zwart: “Find your tribe.”

Something I wish I had access to in law school and as a young lawyer was information on alternative law firm structures and interesting ways people have used their law degrees outside of the law. The legal industry is so old-school, and although things have changed quite significantly since I was in law school, there […]

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Something I wish I had access to in law school and as a young lawyer was information on alternative law firm structures and interesting ways people have used their law degrees outside of the law. The legal industry is so old-school, and although things have changed quite significantly since I was in law school, there is still a major focus on practicing in traditional firms, which, for the most part, still operate with the mentality that the more hours you work (and bill clients), the better the lawyer you are. But the younger generations really value balance and a career that provides them the opportunity to actually enjoy the fruits of their labor, so many have turned to different careers or unique paths within the law. The important thing to remember is that there are so many different options in terms of what a legal career can look like, and you don’t have to settle for what already exists. There is a lot of opportunities to create the career you want.


As a part of my series about “5 things I wish someone told me when I first became an attorney” I had the pleasure of interviewing Keren de Zwart.

After working for 10 years in the corporate arena, Keren had a desire to fill the legal gap for entrepreneurs and small businesses by replacing the outdated billable hour model with flat-fee pricing. With over a decade of experience in corporate transactions, Keren has worked with every type of business: from side hustlers to raising millions of dollars and taking companies public. Today, she helps entrepreneurs get #legallylegit through her law firm, Not Your Father’s Lawyer. She resides in Orange County, California, with her husband and two children.


Thank you so much for joining us! Our readers would love to get to know you a bit more. What is the “backstory” that brought you to this particular career path in Law?

What started as a very linear path took quite a few detours to get to where I am today. I said I was going to be a lawyer since I was about nine years old. No one really knows why for sure, but we think my father joked that I’d make a good lawyer because I was so argumentative, and it stuck with me. I studied political science in college because I loved it, but also because that was a natural pre-law path. However, once I got to law school, I started feeling like maybe the industry wasn’t for me. Although I was a child of entrepreneurs, I never once considered running my own business. I was the consummate corporate ladder climber. But the old-school industry of law very quickly felt wrong for me.

To add complication to my uncertainty about the practice of law, I came out of law school in 2009 — also known as the “Lost Generation” of lawyers. As part of the Great Recession, law firm jobs were at an all-time low, and because I was determined to work only in corporate law, I negotiated with the firm at which I had interned to take a very low salary in exchange for a full-time job. In addition to billing 1800+ hours a year, I built their entire web presence, including the firm’s website, LinkedIn company page, email marketing campaign, Twitter account, and more. At the time, I didn’t realize I was setting myself up to have the knowledge and confidence to run my own business.

Can you share the funniest or most interesting story that occurred to you in the course of your law career?

In 2014, I put in my notice at the firm and moved to a non-legal commercial real estate company. By then, I had a blog to share legal advice in a cheeky, unconventional way, but it was mostly a hobby. I was convinced I hated all aspects of the law, and I told my husband that I would never practice law again. I fully intended on following through, but since friends and family knew I was not practicing at the firm, they started reaching out for legal support, and Not Your Father’s Lawyer inadvertently turned into a business. By 2018, I was working full time in senior management in commercial real estate and also running my firm 25+ hours a week, and in 2019 I finally left the corporate world to run my business full-time. Only 5 years after I said I’d never practice law again, I left a career I loved to run a law firm full time. It’s funny to look back now and realize that it wasn’t that I didn’t like the law — I simply needed to focus on a different way to practice from the standard law firm model.

What are some of the most interesting or exciting projects you are working on now?

My entire business is based on helping entrepreneurs and small businesses, so I get to work with people in unique markets. Although most of my clients already operate primarily online, in the last few months, it has been exciting to help small businesses pivot into digital businesses nearly overnight. For example, I worked with fitness studios that almost instantly shifted their membership into online classes and in some cases, renting out their studio equipment for home use. I’ve supported professionals with their move to online consulting due to layoffs or reduced work. I’ve helped a few small business owners leap into completely new and different industries to generate revenue when their existing industry slowed or stopped. That is the most interesting part about working with entrepreneurs and small businesses — they’re incredibly agile and have been able to shift quickly as unforeseeable obstacles have affected their businesses.

What are some of the most interesting cases you have been involved in? Without sharing anything confidential can you share any stories?

Corporate transactional work can be fascinating, even if we get a reputation for being paper pushers. One of the interesting things is how fast business moves and how slow the laws are to catch up to them. So, you often wind up in a sort of legal limbo where regulators aren’t quite convinced a client is doing something by the book, but the book doesn’t even have a chapter on what they’re doing.

Sometimes this has meant working state by state to try to explain to non-tech-savvy regulators why a client’s software platform wasn’t violating payment processing regulations.

Other times it involved penny stock IPOs for vape companies before anyone knew what vaping was.

Working with companies at the forefront of business and technology while trying to work through antiquated laws that don’t fit is a complex, challenging, and exciting aspect of what I do. And I love helping business be the leading edge of those waves and create entire new business verticals that didn’t exist even a few years ago.

Which people in history inspire you the most? Why?

Reaching far back in history, reading Thomas Paine as a young teen was what really fueled my passion for civics and the law. Paine was an incredibly persuasive writer and an ardent advocate of reason.

And as a lawyer passionate about supporting women, I am inspired by the many women who have broken barriers in their respective industries, perhaps none more so than Sandra Day O’Connor as the first female Supreme Court Justice.

What advice would you give to a young person considering a career in law?

Something I wish I had access to in law school and as a young lawyer was information on alternative law firm structures and interesting ways people have used their law degrees outside of the law. The legal industry is so old-school, and although things have changed quite significantly since I was in law school, there is still a major focus on practicing in traditional firms, which, for the most part, still operate with the mentality that the more hours you work (and bill clients), the better the lawyer you are. But the younger generations really value balance and a career that provides them the opportunity to actually enjoy the fruits of their labor, so many have turned to different careers or unique paths within the law. The important thing to remember is that there are so many different options in terms of what a legal career can look like, and you don’t have to settle for what already exists. There is a lot of opportunities to create the career you want.

If you had the ability to make three reforms in our judicial/legal system, which three would you start with? Why?

As a business lawyer, I’m passionate about reforms that can help my clients. A lot of reform needs to happen around access to capital for small businesses. The JOBS Act was a step in the right direction, but for microbusinesses, any sort of fundraising is still cost-prohibitive because of the regulations that require the counsel of a securities lawyer.

I’m really hoping for some disruption in the litigation world, too. The process is still so slow, terribly cost-prohibitive makes frivolous claims too easy to pursue, and fails to support valid claims that get lost in a sea of intentional delay tactics that can bankrupt a litigant. Mediation and arbitration are still surprisingly expensive and time-consuming. I’d love to see technology used in a way to create efficiency in conflict resolution since I’m not as hopeful that the laws and court processes will change.

Looking upstream, there needs to be a huge overhaul of the law school industry, including access to schools, cost, and practical training that lawyers need but don’t receive before practicing law, like running a firm, acquiring and maintaining clients, networking and preparing for growth, understanding equity and non-equity partnerships — the list goes on.

How have you used your success to bring goodness to the world?

Entrepreneurs put their hopes, dreams, and livelihoods into their businesses, so although I am not saving lives, I do everything I can to protect my clients’ livelihoods. My work fills a huge gap for entrepreneurs and small businesses by providing access to someone with corporate legal experience at affordable rates and in a non-traditional way. The passion that drives me to continue to practice law is all about providing information and access to those underserved by the current legal model, and in particular female-owned businesses, so they don’t have to try to build a business without the legal foundation in place simply because they are priced out of the traditional legal market.

I know this is not an easy job. What drives you?

To be honest, what drives me are the comments from clients like, “You’re not like any lawyer I’ve ever met,” and, “I didn’t think a lawyer like you existed.” I spent the beginning of my legal career butting up against a model I felt was outdated and failed to serve a major sector in business, and I found a way to fill it. I get to work with passionate, talented, fun, and innovative business owners and be a small part of the community that is changing the way people think about legal services.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or an example for each.

  1. Be creative. There is a lot of pressure to get a BigLaw job or a clerkship or a fancy in-house role, but those jobs are few and far between, and there are plenty of other ways to make a name for yourself. If you have skills or interests outside of law, see how you can utilize them either directly in your firm (as I did with marketing for my firm) or find a way to side hustle to explore your passions.
  2. It’s okay to do things differently. The legal industry has been shifting over the past 15 years, and I’m hopeful it will continue to change. Now is a great time to lead the charge with new and innovative ways of practicing law and serving clients. Don’t be afraid to go against the grain.
  3. Don’t chase the money. Very few lawyers I’ve met or worked with have ever actually enjoyed the ridiculous hours that come with the highest paying roles. Set out on the path that you want to be on, find what fulfills you, and the money will follow.
  4. Find your tribe. Even if it doesn’t seem like you fit the traditional legal industry fraternity, take time to network and search for groups online. There are amazing attorneys doing things differently and they’re out there with an outstretched hand, waiting to welcome and support you.
  5. Don’t be afraid to ask. Whether it’s getting help with a transaction or case, asking for a referral for a dream position, or looking for insight on your career path, people are more willing to support you than you might think. The worst someone can say is no, so don’t be afraid to ask for what you want.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

I have a major business crush on Reese Witherspoon. Aside from being a talented actress, I am in awe of all the different ventures with which she’s been involved, and she really focuses on empowering others. I’d love to pick her brain about choosing new business opportunities, scaling existing businesses, and using your platform to support others.

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