We were lucky to catch up with Rob Massar recently and have shared our conversation below.

Alright, Rob thanks for taking the time to share your stories and insights with us today. I’m sure there have been days where the challenges of being a business owner force you to think about what it would be like to just have a regular job. When’s the last time you felt that way? Did you have any insights from the experience?

At least once a month I look at myself in the mirror and think “What am I doing? Why do I continue to choose this path?” Entrepreneurship has challenged me much more than I anticipated. I am happy as a business owner because I have agency and freedoms others do not, but the reality is that running your own business is much harder than anyone admits. We all have skills and we all have blind spots, but when you are a business owner you cannot only focus on your skills and avoid your blind spots. You can do that in the normal work world because you’re hired for your skills, right? As an entrepreneur the harsh reality is that your blind spots can ruin your business. Do you avoid opening intimidating mail from the government? Well, you could be missing a delinquency notice and in a few months you may owe the government thousands of dollars and be forced to empty out your operating capital. Are you a great product designer but poor sales person? Well, it doesn’t matter how good your product is because with no sales you have no business.

The last time I was very anxious about having my own business I felt over extended and out of my league. I had many clients to juggle and money was tight. So, I took on a client for a substantial sum of money that was just at the edge of my competency. However, I didn’t anticipate how much hand holding the client wanted or how much research I would have to do to competently handle their matter. I was spending more time than I was being compensated for and I was negligently handling other client matters. So, I was (1) doing work I didn’t feel experienced or confident in, (2) felt underpaid, (3) had lots of other work to do and tight timelines I couldn’t meet, and (4) I was taking work home with me and it negatively affected my relationship with my wife, sleep, and mental health.

So, I asked myself, why did I do this to myself? I could have avoided this situation. I could have communicated with my clients better. Or, sheesh, I could just get another job and show up to work at 9, have my boss tell me what to do, and then leave at 6. Maybe then I wouldn’t take work home like I do now. Maybe I wouldn’t feel so personally attached to clients or like I was letting them down. Well, at the end of the day I took a long walk, spoke with some close friends, and I was reminded of my “why” (yes, the cliche every social media entrepreneur preaches). But it is true. Your “why” will keep your feet on the ground and nose pointed towards your north star.

Rob, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

My practice is all about giving clients peace of mind for their pursuit. I want to help people find financial freedom and chase their dreams. It’s what I do personally and I want to surround myself with people who do the same.

I was born in Los Angeles and went to high school in Santa Barbara, CA. I always loved playing sports and went on to play Division 1 baseball at the University of Richmond in Virginia. Following college I worked for the MLB’s Urban Youth Academy in Compton, CA where I tutored and coached local youth. I then became the General Manager of the Santa Barbara Foresters, a semi pro baseball team in Santa Barbara, CA. I recruited and managed the active player roster, hired and managed 16 interns, ran the Sales/Marketing/PR of the organization, and raised funds for the organization’s 501(c)(3) pediatric cancer charity Hugs for Cubs. My goal was to become the GM of an MLB team by the time I was 30.

I then enrolled at Loyola Law School in Los Angeles, CA where I concentrated in Entertainment and Sports law and was an active member of the Entertainment and Sports Law Society. While in law school I worked at Paragon Sports International, a sports agency in Beverly Hills representing some of the MLB’s best talent. I also worked for three years as a talent scout for the Chicago Cubs and New York Yankees. In my final law school summer I went back to the Santa Barbara Foresters for a season and sat on the board, coached alongside Hall of Famer Bill Pintard, and played in the NBC World Series. Needless to say, my law school summers were MUCH different than my peers’.

After passing the California Bar Exam Rob I was offered a full time position with the New York Yankees but turned it down. I realized in client services and talent representation I could have the most impact on people’s lives and do what I do best: solve problems and help people build their dreams. So I became a sports agent, representing professional baseball players, for Paragon Sports International. I then realized, however, that with my own practice I could help talent of all types: businesses, creatives, artists, and athletes. So, I founded my own boutique practice and haven’t looked back since.

Can you tell us about a time you’ve had to pivot?

After college I made a plan to become the general manager of an MLB team by the time I was 30…and I told everyone I could about my plan. “Speak it into existence” or “put it out in the universe” is what everyone always said, so heck, I thought I’d try. Everything I did was to position myself and hone my skills for that front office job. My admissions essay for law school was even about how I DIDN’T want to become a lawyer and had a step by step plan to become one of the youngest GMs ever. I had a plan. I sacrificed my social life because I wanted to be on the road learning how to scout, evaluate talent, communicate with talent, and politic within a large organization.

Then I graduated law school and I got a full time offer from the Yankees. I turned it down. I felt like such a fraud and like I’d lied to everyone. I also felt like I let the people down who had supported me and gone out on a limb for me. I was confused. I was lonely. I’d spent so many years working towards a specific goal and then it felt like in the blink of an eye my inspiration and excitement was gone. The reason I made the pivot, however, was so that I could stay in Los Angeles, be close to my friends, close to my family, pursue my passions and hobbies, and not make baseball my whole life.

I learned in baseball, and I feel this is similar to most “cool” jobs (e.g. ones with as much social benefits as financial benefits), that if you’re not ALL IN or completely bought in, then someone else will be and they’ll take your job. I wasn’t ALL IN. I had other interests and had lost the maniacal drive to be the youngest GM in the MLB. So, I turned the Yankees down (while I was in Central Park visiting friends in NY!) and picked up side gigs to make ends meet. Then a friend said he needed legal help on an independent film and I said “ABSOLUTELY!” Then another friend said they were hiring a startup lawyer. I said “I can help for half their price!”. Those few thousand dollars were my seed capital, and now, seven years later, I have my own boutique firm and I do business all around the globe. I think what I learned the most from this experience was that (1) having a plan is good, but they’re not set in stone, (2) don’t be afraid to let your heart and feelings guide you, and (3) it’s your life!

Can you tell us about what’s worked well for you in terms of growing your clientele?

Putting people first. Attorneys have many hard skills to help clients, but it’s my soft skills that have helped me the most. One of my most formative jobs was being a baseball coach at the high school and semi-pro baseball level. I loved being around the guys and helping them get better everyday. It’s totally cliché, but when you help someone, they work their tail off, and then they achieve their goal it feels amazing. So, with my business I really try to focus on the person. Who are they? What are their motivations? How can I help assuage their anxieties and help them grow strategically? How can I give them peace of mind for their pursuit? We all deserve that.

Contact Info:

• Website: https://www.rmlegalstudio.com/
• Instagram: https://www.instagram.com/rmlegalstudio/?hl=en
• Linkedin: https://www.linkedin.com/in/rob-massar-68289b44/