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Jamie Lieberman of Hashtag Legal: “Try everything that interests you, even if it scares you”

Try everything that interests you, even if it scares you. If you would have asked me eight years ago if I would co-host a podcast, speak in front of large groups, or regularly create videos for social media, I would have looked at you like you were crazy. By trying new things, it allows me […]

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Try everything that interests you, even if it scares you. If you would have asked me eight years ago if I would co-host a podcast, speak in front of large groups, or regularly create videos for social media, I would have looked at you like you were crazy. By trying new things, it allows me to learn what I love to do and what I never want to do again. Don’t be afraid to look silly or to fail!


Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Jamie Lieberman.

Jamie Lieberman, owner and founder of Hashtag Legal, a law firm specializing in working with creatives and online businesses, and the co-host of the FearLess Business Podcast, has been a practicing lawyer for 15 years. As an experienced entrepreneur, Jamie understands the unique needs of business owners at different stages in their organization’s growth. She has a deep commitment to making legal accessible and regularly speaks about legal matters, the art of negotiation and entrepreneurial topics at leading industry events such as Alt Summit, Podcast Movement, and FinCon and as an expert source for media like Digiday and Forbes.


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up in a suburb of Philadelphia and always loved math and science. I eventually ended up attending Lehigh University to study engineering. At that time, there were not many women in the field, so from a young age I experienced what it felt like to work in a male dominated field. These lessons helped me over the course of my career.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“When someone shows you who they are, believe them the first time.” ―Maya Angelou I have learned that relationships are the foundation of every successful entrepreneur. This means not only cultivating the good relationships, but also knowing how to set boundaries and when to end those relationships that are not positive. Some of my best decisions in business related to the end of relationships.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

The top three qualities that have helped me achieve success are flexibility, a willingness to be adventurous and decisiveness. When I left my law practice to start my own business, I not only practiced law but I also accepted non-legal freelance jobs so I could learn about new industries. Many of them did not pay well, but they gave me a chance to experience a new field. It was actually a job writing for a blog about parenting that led to me to create Hashtag Legal. By being open to many experiences, I ended up finding a way to connect my creative side with my legal practice.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

I feel like I have had a lifetime of careers! Before attending law school and after college, I worked in the fashion and publishing industries. The publishing company that I worked for created the first daily online newswire that published information about the venture capital field. It was a very interesting place to work and I learned about innovation there. After working for five years, I decided to go back to law school and change my career, once again. After law school, I worked at two traditional law firms and then for the federal government. I worked as a complex commercial litigator in a large, international law firm on a litigation team of 30 people. These were very different working environments than where I am now!

And how did you “reinvent yourself” in your Second Chapter?

I became very burnt out as a litigator because I spent my days in adversarial proceedings and the lack of civility in the practice had taken its toll on me. I decided to shift my practice from litigation to transactional work so I could focus on helping others, rather than focusing on disputes. I also knew that I wanted to work with different types of clients than I had in the past. My prior experience had been with Fortune 500 companies, banks and financial institutions. I knew I wanted to find a way to work with creatives, because I had been a creative myself, writing a blog and publishing my photographs. Going from providing legal services to banks to providing them to creatives was a huge shift.

I also knew I wanted to change how I offered legal services. When I created Hashtag Legal eight years ago, it was unheard of in the legal world to work with clients virtually. In fact, I was repeatedly told by other lawyers that my clients would not want to hire a virtual law firm and that there was no way my law firm could be profitable. I was also told I wouldn’t be taken seriously and that a more casual approach to offering legal services would degrade the practice.

I knew that those critics were wrong and I created Hashtag Legal in a way that felt authentic to me and would make my clients feel comfortable. With this shift, although very scary to make, I was also finally able to be myself in my practice, by communicating in an easy and accessible way and presenting myself in the way I wanted (with nose ring, dyed hair and tattoos showing), which is not how lawyers typically look. I also created a pricing model that would be profitable, but also manageable for small business owners.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

I had just returned from maternity leave after having my first son and I went back to work at my 9 to 5 job. I quickly realized that I would have to choose between seeing my son and being successful at work. I didn’t think this was a choice a mother should have to make. I decided to leave so I could create a working environment that would allow me to practice law and spend time with my family. I was also disappointed at the lack of civility I found in the legal field and wanted to find a way to practice in an environment that was welcoming.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

When I finally began to work for myself, I realized that being in working environments that didn’t allow for innovation had actually dulled my love of being a lawyer. Having the ability to create a law firm that I had envisioned was freeing and enabled me to be creative again.

How are things going with this new initiative? We would love to hear some specific examples or stories.

Things are going really well. I have created a successful and profitable law firm, and I am able to offer my employees autonomy, flexibility and a working environment that values work and life outside of the office. My employees work virtually and have flexible schedules. We have the opportunity to work with incredible clients, who are innovative business owners and entrepreneurs. It is exactly what I dreamed of when I set out on this journey.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

When I worked at the publishing company prior to attending law school, the CEO continually challenged me and gave me responsibilities that were far outside of my comfort zone. He believed in me at a time I did not believe in myself and I often think about what he would do when I am making decisions in my business. When I tried to refuse projects because I thought they would be too hard or outside of my comfort zone, he wouldn’t let me say no. I am incredibly grateful for his faith in me.

Can you share the most interesting story that happened to you since you started in this new direction?

I wrote an article for Working Mother magazine about navigating toxic work environments based on my experiences in the legal profession prior to starting Hashtag Legal. I never imagined it would hit such a nerve with so many women. I received many emails and private messages on social media from other women with similar experiences. I even heard from someone that the article inspired her to finally quit her job! It renewed my commitment to supporting business owners and empowering them to create working environments that meet their values.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

I enjoyed attending law school a great deal and found that being a lawyer was something I am naturally good at. When I graduated and began practicing law, the working environments at tradition law firms made me question myself and my skills. By the time I left that practice, I did not even know if I still wanted to be a lawyer. Thankfully, once I was able to start my own business, I remembered why I loved what I did and I was slowly able to build up my confidence.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I started by talking with my family, particularly my husband, to make sure they were on board with the risk in starting a business. Thankfully, they were incredibly supportive. I then talked to every single person I knew (and many I did not) about running a business. I was mostly interested in learning about their stories, their hurdles and how they found success. Just listening and making these connections was the support system I needed. I still call on many of them now!

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

When I first decided to create Hashtag Legal, about eight years ago, I was freelancing for a company that ran a conference for bloggers. This was before the word “influencer” existed and bloggers were just starting to monetize. At the time, I was supporting the conference through legal work and also helping to run it. The owner of the company realized that many bloggers needed legal representation, but did not have a resource who understood the industry. She asked me to speak about “legal issues for bloggers.” Prior to this request, I had never spoken at a conference and had not even considered what legal issues a blogger would have encountered. The opportunity terrified me, but I knew it was an important one. I pushed through that fear, created the presentation and giving that talk was pivotal in helping me crystalize my vision for Hashtag Legal.

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

  1. Try everything that interests you, even if it scares you. If you would have asked me eight years ago if I would co-host a podcast, speak in front of large groups, or regularly create videos for social media, I would have looked at you like you were crazy. By trying new things, it allows me to learn what I love to do and what I never want to do again. Don’t be afraid to look silly or to fail!
  2. Get experience. Although I struggled with my experiences in legal field, without them I would not be where I am. I learned how to be a good lawyer through my experiences as a litigator, even though that was not a job I enjoyed. I also saw many examples of what I did not like in a working environment, which enabled me to create the culture at Hashtag Legal more easily.
  3. Know When To Step Back. Burn out is very real and you cannot just “push through it.” Having a balance of things in your life that bring you joy is critical to success at work.
  4. Stop Networking. Instead, create relationships. Businesses are built on the relationships you form, usually when you least expect it. I met one of my best clients on an elevator talking about a show I enjoyed. I didn’t speak with her looking to get something from the relationship, I did it because I truly love connections with others. You never know who you may be talking to.
  5. Learn how to truly listen. As a person who loves talking, I still practice this every day. Listening is a skill that continually needs to be honed and is often overlooked. I speak with clients every day and I have learned that they may be presenting me with one question, but if I listen carefully, there are many other questions that the client also needs to be answered. By focusing on my client, listening to their stories and letting them do the talking, I am able to give focused and effective counsel.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I would love to inspire people to take the toxicity of the workplace, to be open to feedback from employees and to bring back innovation.

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

My answer to that is always the same — Ruth Bader Ginsburg and Sandra Day O’Connor. Since RBG has passed, maybe Justice O’Connor would love to have breakfast with me.

How can our readers further follow your work online?

Website: www.hashtag-legal.com

Instagram: www.instagram.com/hashtag_legal

YouTube: www.youtube.com/jamieliebermanrocks

Thank you so much for sharing these important insights. We wish you continued success and good health!

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