Jenna Gregory
Business Owner and Financial Advisor
Laguna Beach
My Role
I’m a mom. I’m a business owner. I’m an advocate. I’m an educator.
With 10+ years of experience in the financial services world, our team focuses on bringing confidence and clarity for women and their families and empowering them to feel secure.
The span of my relationship management career has been in and around the commercial real estate finance and occupier industries, with a brief stint in manufacturing. I learned as a new mother that nothing is more important than protecting my family and creating a plan to set them up for success, while bringing peace of mind that we are not leaving any money on the table due to inefficient tax or investment strategies.
Through asking thoughtful questions and understanding how the logical and emotional parts of navigating personal finance work for you - we will customize a plan to set you and your family up for financial security and health, ultimately leading you to have more choices and peace of mind. We work to increase your confidence and clarity around your financial picture through education and actionable plans.
What I love most about my role
My love of educating others and empowering those around me to feel confident fueled my journey into financial planning, and this is what I'm most passionate about. I love talking to and helping new moms with young families (I'm on the board of our town's local Parent's Club), and making a positive impact on our local community.
How I define success
Success, to me, is when what I’m doing daily — whether in business, family, or personal growth — aligns with my values and makes a positive impact. It’s not just hitting metrics or goals, but feeling proud of how I got there: the integrity, kindness, and authenticity in each decision. When I can look back and say I lifted others up along with myself, that feels like real success. All while making the time to spend with my family and enjoy our wonderful life.
The best piece of business advice I ever received was
The best advice I got was: “Decide who you serve, deeply.” When you are crystal clear on who your work is for, everything else gets easier — your messaging, your priorities, your boundaries, even what you say “no” to.
What would I tell my younger self
I’d say: “It’s okay to move slower; clarity comes with time. Don’t be so afraid of failing — failures will teach you more than wins sometimes. Trust your instincts. And don’t feel pressure to check all the boxes by a certain age. Your path doesn’t need to look like anyone else’s - there's only one of YOU.”
What 2B Bolder mean to me
“2B Bolder” feels like a call to show up fully. To have courage, to push beyond comfort zones. It means speaking up, taking risks, owning your story, even when it’s messy or scary. It’s about boldness that’s grounded: boldness not for ego, but for purpose and impact. To me, it means daring to lead by following my heart.
Years of Experience
15
I recommend you focus on developing these 3 skills to succeed in a role like mine
1. Communication - making a real connection with people.
2. Perfectionist work ethic (strength and a weakness) - working hard to make sure my clients can sleep well at night, knowing that they can trust me to be on top of every detail for them and the people who matter most.
3. Ability to create balance in my life.