Kendra K. Cleary was born at Dominican Hospital and raised in the Seacliff neighborhood of Aptos, California. A proud local, she graduated from a nearby high school where she was nationally ranked in Forensics (Speech and Debate), and then went on to attend Cabrillo College.

Kendra began her professional journey in 2006, joining Eric Costello’s team—then affiliated with Edward Jones—as a part-time Branch Assistant. Over the years, her role and responsibilities grew significantly. She earned multiple promotions and was eventually named a Limited Partner, becoming the youngest non-sales Limited Partner in Edward Jones history at the time. During her tenure, she received numerous accolades for both service and business achievements.

In 2013, Kendra and Eric launched their independent financial planning practice, Costello Wealth Strategies, Inc., aligning with Raymond James Financial Services. Kendra serves as both Client Services Manager and Office Manager, and is known for her deep commitment to client relationships, organizational leadership, and community involvement.

Community service has long been a cornerstone of Kendra’s life. After several years of volunteering, she officially joined the Capitola-Aptos Rotary Club in 2013. She has co-chaired the club’s annual major fundraiser, including the memorable 2018 campaign that raised $140,000 for LEO’s Haven, Santa Cruz County’s first inclusive playground. The Kentucky Derby Party fundraiser now supports dozens of local charities through the Capitola-Aptos Rotary Community Grants Program, benefitting organizations such as Unravel Pediatric Cancer, Safe Families for Children Monterey Bay, and Pajaro Valley Loaves and Fishes.

Kendra served as Co-President of the club during the 2022–2023 term. Under her leadership, the club launched two new fundraising events—a Kentucky Derby Party and a Pickleball Tournament—and distributed $25,000 in scholarships and grants. During that year the club also helped fund accessibility improvements to Willowbrook Park and Treasure Cove at Jade Street Park.

Kendra is also active in cultural and heritage initiatives. She serves as Orator and sits on the Board of Directors for the Sons and Daughters of Italy in America (OSDIA), Watsonville Lodge #2006.

Deeply rooted in Santa Cruz County, Kendra cherishes time with her close-knit family—including her mother Terry, a recently retired teacher; her Aunt Pat. Her grandfather Ken (who Kendra was named after!) was a WWII veteran, he was a center gunner on a B-17 stationed out of Polebrook Air Force Base (England) and flew 35 missions over Germany during 1944-1945. Ken was with the 8th Air Force, 351st Bomb Group, 509th Bomb Squadron. One of her most treasured memories is touring a B-17 with her grandfather before his passing in 2020.

Kendra is a proud aunt to nephews Kent and Miles, and godmother to Hudson.

As Eric gives back to his own hometown by coaching football at his alma mater, Del Norte High School, Kendra continues to be the heart of client service and operations at Costello Wealth Strategies. Together, their shared values of community, loyalty, and integrity shape both their business and the enduring relationships they build in both Santa Cruz and Del Norte Counties.

Kendra will celebrate 20 years with Costello Wealth Strategies in the summer of 2026.