We had the good fortune of connecting with Jenna Glassock and we’ve shared our conversation below.

Hi Jenna, we’d love to hear about how you approach risk and risk-taking
I think about risk a lot as I am a generally risk averse person who chose a relatively risky career path of starting my own law firm. Coming out of college, I picked the path that felt most familiar to me and chose to go to law school. My mom and step-dad were both lawyers, and I liked being in school, so the choice felt obvious. Upon graduating from law school, I picked the career path that law schools tend to nudge you toward: I went to a big law firm.

This pattern of floating down a river of simple decisions was interrupted for me when my mom passed away. My mom had been a lawyer who had been fairly miserable with her career for the prior couple of decades. I know why she did it: she lovingly made the decision to keep a high-paying job that she hated so that she could support me and give me every opportunity. But, it was at the cost of her happiness. I saw myself making similar decisions that she had made, getting comfortable in a job that no longer made me happy but that paid me well. I realized that if I didn’t break out of that pattern, her sacrifices would have been for nothing.

I decided to leave my law firm, knowing I wanted to do something entrepreneurial. But even then – when finally filled with a fervor to take a risk for once! – I picked the least risky, risky choice and got my MBA with a focus in entrepreneurship.

After graduating with my MBA, I was again at a crossroads: the safe choice of a corporate job or the risky choice of starting my own firm. If there are multiple timelines out there, then I imagine, in most of them, I picked the corporate job. But, in this one at least, I took the leap. What finally got me to that point was the birth of my son at the end of my MBA journey. I was home with an infant applying to corporate jobs, knowing that every great opportunity offered to me meant losing control over the decision whether to take him to school every morning or go to his mid-day recital or take a day off to play hookie. And the fear of losing that freedom and that time with him was ultimately greater than the fear of taking the risk to start my own firm.

Even after deciding to start my own firm, my risk aversion still comes into play. I wrote a 50 page business plan for what was originally meant to be a one-person law firm, working through all possible risks and threats. My pro forma projections were wildly conservative, and I was overly cost conscious, not wanting to put too much of a financial burden on my firm before I had proved to myself that it would work.

With every success we have and goal we meet or surpass, I get a little more confident in taking risks. I know that we need to take risks to have greater successes, but I’m always fighting against my nature in doing so. That’s part of being a business owner though, and I’m glad I get the chance to take on those decisions every day!

Alright, so for those in our community who might not be familiar with your business, can you tell us more?

Laurel Trust Law is a trusts and estates law firm that specializes in estate planning, trust administration, and probate representation. We try to set ourselves apart by prioritizing the client experience and doing our best to make what can be an unpleasant process – discussing family and money and what will happen after your death – as painless as possible.

I came to this area of law due to a really painful personal experience after my mom passed away. We know and have experienced the downsides to not having an estate plan. We are motivated every day to help our clients avoid that type of unpleasant and expensive experience for their families, and to try to make that process as easy for our clients as we can.

I am so proud of what we have built Laurel Trust Law into. I started my own firm almost six years ago, and it was just me and my computer drafting estate plans in California. Today, we have two full-time attorneys (me and my partner), two full-time staff, and six of counsel attorneys. We have expanded beyond basic estate planning to include trust administration, probate representation, business formation, and advanced tax planning. We are able to provide estate planning services in seven states.

Growing this much in a relatively short period of time has absolutely had its ups-and-downs. Deciding to hire was a really difficult decision and a pretty daunting undertaking for someone who had never done it before. There were definitely some imperfect hiring decisions that we went through along the way before securing the amazing team that we have now. Having those experiences, though, really helped us understand what we were looking for in our employees. An important lesson we learned was the value of having our employees close by. When we first started hiring, everyone was remote due to Covid, so we thought we could have employees anywhere in the country. We learned that, even though we wanted to maintain some amount of work-from-home flexibility for our staff, having them nearby to be in the office part-time has been really helpful for the type of roles we were filling.

One of the best decisions I made to help grow the business and keep the entrepreneurship experience fun was partnering with my law partner, Kelly Hughes. Kelly and I went to law school together, spent a summer as legal interns together, and studied for the California bar exam together. It was because of those experiences that we knew that we could make a really good team. Having someone whom I trust to help strategize for and run this business has made the whole thing so much more enjoyable. While I know many partnerships that have not gone as smoothly as mine and Kelly’s, for me, finding a good partner has been absolutely critical.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
One of my favorite things about Los Angeles is how many great options there are for outdoor activities. We would be going on a lot of hikes, and I particularly like Fryman Canyon or Placerita Canyon with kids or some of the lesser-known trails in Malibu if it’s just adults. The All Trails app is great for finding new hiking spots. I would definitely plan one or more beach days; there are some great hidden beaches in Malibu, or Will Rogers and Annenberg are great with kids. If there is some nice weather, one of our favorite LA activities is riding bikes from Santa Monica down to Manhattan Beach, grabbing lunch and walking around a bit, and then riding back. A day trip to Santa Barbara is always fun, especially with friends who would enjoy wine tasting or beer tasting. If we’re lucky, there would be a good show we could see at the Hollywood Bowl or at the Hollywood Forever cemetery.

Who else deserves some credit and recognition?
My husband, Mark. Every difficult decision I have had to make has been made easier by his involvement. He has spent countless hours listening to me vent, brainstorming with me, and helping with other aspects of our lives to let me follow my dreams. When I was too scared to take the entrepreneurship leap, he is the one who told me that I could do it, that I would be successful, and that if, for some reason, I wasn’t, everything would still be ok. I truly couldn’t do any of it without him, and I appreciate him so very much.

Website: https://www.ltlfirm.com/

Instagram: @ltlfirm

Linkedin: linkedin.com/in/jennaglassock

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