As a CERTIFIED FINANCIAL PLANNER™ professional, Gary helps clients envision their financial futures and align their wealth accordingly. With a passion for connecting with people and learning their unique stories and dreams, Gary helps his clients navigate both everyday scenarios and complex financial decisions so they can accomplish their goals with confidence. His mission is for clients to rely on him and his team to guide them through life, and he feels a sense of pride and duty when clients seek his advice before making financial decisions. He enjoys helping others arrange the “puzzle pieces” of their financial world, and the best part of his job is helping each client see their future through a brighter, clearer lens because of their work together. Gary founded his firm in 1985 while graduating from the University of Virginia. He soon discovered a passion for working with families and business owners in the Charlottesville community, and in time, Taylor Associates became a leading provider of employee benefit plans in the area. The firm now works with many community leaders, providing wealth management and estate planning in addition to employee benefit services.

EDUCATION & DESIGNATIONS

• University of Virginia – Bachelor’s degree
• Darden School - Leadership for Extraordinary Performance
• MIT - Leadership Development Program
• Harvard Law - Negotiation Program
• CERTIFIED FINANCIAL PLANNER™
• Chartered Financial Consultant®
• Chartered Life Underwriter®
• Accredited Estate Planner®

AWARDS & ACCOMPLISHMENTS

• Forbes #40 Financial Security Professional – 2021
• Small Business Person of the Year – Chamber of Commerce
• Leader’s Leader – Leadership Charlottesville
• MDRT Top of the Table
• Community Service Award (twice) for Northwestern Mutual

COMMUNITY INVOLVEMENT

• UVA Health – Cancer Center – former advisory board member and leadership donor
• Paramount Theater – founding board member and past chair
• Charlottesville Regional Chamber of Commerce – past chair and past board member
• Virginia Institute of Autism – Campaign Steering Committee
• Piedmont Virginia Community College – past board member
• Virginia Discovery Museum – past President and past board member
• Central Virginia Estate Planning Council – past President and past board member
• University of Virginia Athletic Foundation – leadership donor and suite holder for UVA Football and Basketball seasons

PERSONAL LIFE

Gary was married for 35 years until cancer took his wife’s life in 2018. Together, they had three daughters, Kari, Hilary, and Morgan. Kari (the oldest) is part of the Taylor Associates team. She married James in 2022 and they had their first daughter, Bea, in 2023. Gary’s second daughter, Hilary, lives in Lynchburg and has two daughters, Scout and Kappie. Gary now works remotely every Wednesday so he can spend time with his granddaughters. His youngest daughter, Morgan, is a Program Coordinator for WorldStrides here in Charlottesville.

In April of 2021, Gary married Leigh Cantrell, a GYN Oncologist at UVA Health. Leigh has two children of her own—Allison loves volleyball and anything musical; Quentin plays basketball and is “crazy good” at video games! They have black and yellow Labradors named Tilly and Oakley.

Gary loves to cook, entertain, travel, and spend time with his family. Together, they enjoy spending time at their home in Charlottesville, on the water at their cottage in Urbanna, Virginia, and in the mountains of Brevard, North Carolina, where Leigh grew up. They also enjoy boating, sailing, skiing, snowboarding, and traveling. Together, they’ve traveled to a number of national parks and taken several sailing trips across the globe, including in the Virgin Islands, New England, Florida Keys, and Italy. Gary and Leigh hope to one day visit Italy, Spain, and Africa (for a safari) together.

Michael loves being the trusted person that others come to with their financial questions. Michael knows financial planning is deeply personal and relational, and he loves making people feel encouraged and cared for. With his knack for problem solving and desire to see others succeed, he knows he’s right where he needs to be—helping change lives, marriages, families, businesses, and communities for the better.

Michael helps clients identify financial strategies that best coordinate with their situation and goals. He focuses on retirement income distribution plans and tax efficient strategies, and he especially loves working with couples who are preparing for retirement. His mission is to give them confidence about their spending and giving strategies so they can enjoy their success, take care of the people and things they care about, and feel peace about the future. Michael also consults with business owners about their corporate benefit plans and executive compensation strategies and helps them identify ways to improve financial literacy for employees.

As he works with clients, Michael focuses on education, presenting research and data from both the industry at large and his experience with clients to outline the advantages and disadvantages of specific strategies. His goal is to create flexibility for clients, and ultimately, he hopes to provide clarity so they understand their financial position today and what’s possible in the future, giving them confidence to make sound financial decisions in every season of life.

PROFESSIONAL HISTORY

During college, Michael planned to go to medical school but later decided he wanted to manage hospital systems. After graduating, he worked for the Charlottesville Free Clinic and helped start an innovative healthcare access program for the community. He then worked for a few years at Martha Jefferson Hospital with their orthopedic practice.

Michael has always had a passion for improving lives and a gift for operations and analytics. Joining Gary’s practice in 2012 allowed him to build on these same passions and skills while being part of a dedicated, growth-minded team.

EDUCATION & DESIGNATIONS

• University of North Carolina at Chapel Hill – Bachelor’s degree
• Series 7 and 66
• Life, Health, Annuities, & Long-Term Care insurance licenses
• CERTIFIED FINANCIAL PLANNER™ Professional
• Retirement Income Certified Professional®
• Chartered Financial Consultant®
• Chartered Life Underwriter®
• Chartered Special Needs Consultant®
• Accredited Estate Planner®
• Completed Chartered Financial Analyst® Exam Level 1
• Qualified Plan Financial Consultant (QPFC)

AWARDS & ACCOMPLISHMENTS

In 2015, Michael was selected as one of seven people to serve on a Field Staff Advisory Committee for Northwestern Mutual. As part of the committee, he spent two years offering insight and feedback to the home office, and he served as an education and career resource for Field Staff. Michael was also selected to be part of the Leadership Development Program at Northwestern Mutual.

COMMUNITY INVOLVEMENT

Michael is an active deacon at his church, Trinity Presbyterian, where he serves on multiple committees, including the Chair of the Finance Committee. Michael also serves on the Board and Finance Committee for the Center at Belvedere.

PERSONAL LIFE

Michael lives in Charlottesville, Virginia, with his wife Mallory, an incredibly talented wedding florist. They welcomed their daughter, Goldie, in 2024 and have three other children — their daughter, James, and two sons, Waters and Ephraim. They also have a black Labrador named Brooklyn. When Michael is not involved in a family activity you can often find him reading, watching college sports, or napping. With a good nap, however, Michael loves hiking, mountain biking, fishing, playing soccer leagues in Charlottesville, and exploring new restaurants. His bucket-list goals include an extensive travel list, skydiving, becoming fluent in Spanish, and learning to play a musical instrument.

In his role as a lead advisor, Tripp develops financial plans, helping clients with retirement income planning, insurance planning, and investment management. With a holistic approach and a desire to improve their financial wellbeing, he takes time to listen and identify what’s important to his clients before offering recommendations. Tripp loves getting to work with an incredible team and develop lasting relationships with his clients, and his greatest sense of accomplishment comes when they express their appreciation and gratitude for their work together.

Tripp joined Legg Mason, an investment management company, in 1999 after a friend introduced him to the firm. Later, in 2003, he joined Northwestern Mutual, where his uncle was an agent, and in 2014, he became part of the Taylor Associates team.

EDUCATION & DESIGNATIONS

• Virginia Military Institute – bachelor’s degree
• CERTIFIED FINANCIAL PLANNER™
• Retirement Income Certified Professional®
• Certified in Long-Term Care

COMMUNITY INVOLVEMENT

• Diocese of Southwestern Virginia - Standing Committee member
• Diocese of Southwestern Virginia - Trustees of the Funds (President)
• Presbyterian Cemetery - Board of Trustees (President)

PERSONAL LIFE

Tripp lives in Lynchburg, Virginia, and is married to Gray, a program delivery manager for Manpower Group. Between the two of them, they have five children—Tyler, Sarah Gordon, Ava Gray, Lila, and Holt. They also have a golden retriever, Beau. In his free time, Tripp likes to cook, play guitar, sing in his church choir, golf, hunt grouse, and shoot sporting clays. One day, he hopes to golf at St. Andrews.

In her role, Kari services clients’ investment accounts by helping with onboarding, account updates, trade requests, ongoing service requests, and other inquiries. She specializes in serving the firm’s business market clients, assisting with employer-sponsored 529 accounts and providing support for 401(k)/SIMPLE plans. She also frequently assists clients with rollover and transfer requests, scheduling, and overall account services.

Kari strives to provide expert guidance, and she’s adamant about ensuring the firm’s clients are aware of expectations and timeframes and that they receive clear, helpful communication. Her goal is to ensure they have a smooth experience and that they always have a personal connection with the team, even if a lead advisor isn’t available. Most of the time, if Kari doesn’t know the answer to a client’s question, she knows where to find it. She’s passionate about the service their team provides to the Charlottesville community, and she loves knowing she’s handled a question or task well for the team and their clients.

Being Gary’s daughter, Kari has a lifelong connection with the financial industry. Her father’s business first impacted her when she was about 13—during the summers, Kari would answer phones and file paperwork to help pay for her horse-riding lessons. In 2012, she became the Office Coordinator, and she fully joined the Taylor team in 2013. Since then, she’s focused on investments and operations, both of which suit her skills in communication and task management. She holds her Life/Health and Long-Term Care insurance licenses, as well as her Series 6 and 63 licenses.

Kari lives in Charlottesville, Virginia, and is married to James Baldys, who works for UVA Athletics. The couple had their first daughter, Bea, in 2023. Kari has a black Labrador named Rye. In her free time, she enjoys traveling and scuba diving.

Jessica assists the firm’s clients during the insurance application process, helping with underwriting, policy delivery, service requests, and policy changes to ensure their insurance products meet their needs in every season of life. Her goal is to stay in touch with clients regularly, and she makes it a point to keep them updated on the progress of their applications, underwriting, and policy changes. Her diligent attention to detail ensures tasks are completed correctly from the start, making the insurance process smoother for both clients and the Taylor team.

Jessica loves knowing she’s making a positive impact on people’s lives by helping them protect themselves and their families. To her, the best part of her job is helping others meet their financial goals so they can pursue their dreams while taking care of the ones they love.

Jessica graduated from the University of Virginia in 2018 with a BSED in speech-language pathology and audiology. While she loved the field and thought it was fascinating, she decided she wanted to work in a different industry that still allowed her to make a positive impact on people's lives. She believes financial planning can be crucial to meeting both long- and short-term goals, and she knows insurance often plays an important role in that process. She joined the financial services industry in 2018, and since 2017, she has worked part time at the Shelter for Help in Emergency, a domestic violence shelter in Charlottesville.

Jessica and her husband Nathan live in Palmyra, Virginia, and have four fur babies (all cats)—Bagheera, Oliver, MJ, and Puff. In her free time, she enjoys relaxing at home on her hammock with a good book or podcast, doing yoga, hiking, and trying new restaurants. She hopes to one day travel around Europe.

Caroline graduated from the University of Virginia in 2019 with a degree in Financial Mathematics. During her time at UVA, she was an intern for Northwestern Mutual. Upon graduating, she continued pursuing a career in financial services, first at AIG Retirement Services, then at Edward Jones. Caroline began her professional career as a Financial Advisor, but shifted to a Financial Analyst role which she has found to be an excellent fit given her skills and interests.

Caroline is passionate about helping clients achieve their financial goals. She is a critical thinker who enjoys learning new things and helping people understand how to manage their money. Caroline passed Levels I and II of the CFA program in 2022. She also holds her FINRA Series 7, 66 registrations, and Virginia Life and Health licenses.

Caroline lives in Charlottesville with her husband, Connor, and their daughter, Annie. Annie takes up most of Caroline’s time, but if she has a second to spare you will find her baking, painting watercolor cards, or cheering on the Hoos in JPJ.

Jackson grew up in Gig Harbor, Washington, a small town an hour south of Seattle. His parents, Clay and Carrie, both attended the University of Virginia and work in the legal field. Jackson’s older sister, Heather, attended the University of Richmond. With so many Virginia connections, Jackson grew up dreaming of moving to the East Coast for college. After graduating in 2019, he moved to Charlottesville to attend UVA.

Jackson graduated from the University of Virginia with a bachelor’s degree in economics and history in May 2023. Outside of academics, Jackson spent most of his time serving as a student manager for the UVA men’s basketball team. His favorite memory with the team was when he cut down part of the net on Senior Day after winning the ACC Regular Season Championship.

Jackson first became interested in investing and the broader financial market in high school speech and debate. Since then, he has used his background in economics to expand his knowledge on personal finance and saving for the future.

In his free time, Jackson enjoys exercising, reading, and listening to music and podcasts.

In her role, Courtney provides timely support for client inquiries. On a given day, she helps by updating insurance policies, answering billing questions, updating client information, and scheduling appointments. She prides herself in simplifying complex scenarios, and she loves providing quick and effective service for others. As she interacts with our clients and team members, Courtney strives to be a task “master." Her goal is to respond to requests as soon as possible, and she excels at addressing minor details that make a significant impact on both our clients’ outcomes and our firm’s operations. To Courtney, the best part of her job is working with people she truly cares about, and she loves getting to serve others every day.

Courtney brings a professional background in business and human resources, and in 2012, a mutual friend of hers and Gary’s introduced her to the financial industry. She has a bachelor’s degree in business administration from Kansas State University, and she holds her Life/Health and Long-Term Care insurance licenses.

Courtney lives in Charlottesville, Virginia, with her husband Ronnie and their two children, Courtney has worked less than full time since welcoming Emily in 2018 and Blake in 2021. Outside of work, her kids keep her busy, but she’s looking forward to becoming the avid runner she once was. When she has a free weekend, she loves hiking with her family and friends or visiting local wineries.

Nick assists in the building and implementation of financial plans, helping clients with risk management, wealth accumulation, and wealth preservation and distribution. He specializes in educating clients from all walks of life and making the planning process easy yet meaningful. While he loves the teaching aspect of planning, Nick feels his true value is in understanding clients and putting himself in their shoes—whether they’re buying their first home, sending a child to college, or just wanting to know that everything is going to be okay during their retirement. He does this by focusing on his clients’ goals and taking ample time to get to know them. His mission is to become a trusted advisor who provides support for families for generations to come.

As an Associate Financial Advisor, Nick loves the feeling of walking with clients as they live their lives. To him, there’s nothing like seeing a newborn on a virtual meeting and knowing he’ll get to help put them through college and protect their future. And because of this, he can’t see himself in any other role or field.

Nick has always been passionate about meeting new people and discovering what matters to them, and he joined Northwestern Mutual after graduating from Virginia Tech in 2020. He has a bachelor’s degree in economics and a minor in real estate.

Nick lives in Charlottesville, Virginia, with his fiancé Eleanor whom he will marry in the fall. They met while in college at Virginia Tech, and they’re enjoying settling into their new home in their school’s “rival” city. They have a full house complete with two dogs named Kona and Nui, two rescue cats, Pluto and Skeeter, along with a budding flock of 6 chickens. Nick is an Eagle Scout and enjoys fly fishing, sailing, golfing, snowboarding, and hiking. He loves to spend time outdoors and hopes to one day hike the Appalachian Trail.