Fresh out of Ole Miss University, Carmel High School grad and former Indiana Mr. Basketball, Dave Shepherd teams up with his father William “Coach Bill” and launches Shepherd Insurance from Dave’s basement. The duo’s first sales strategy: Knock on as many doors as possible. They got their start selling life and disability insurance for Franklin Life. Every family member and friend was a potential prospect.

After five years of steady success, Shepherd Insurance was contracted by a regional insurance company to begin offering auto, home, and small business insurance options in addition to their ongoing life insurance business. Dave seized the opportunity to relocate, moving out of the basement and into…a garage.   A renovated one-car garage attached to a small, standalone house was now the new headquarters of Shepherd Insurance. Being the only house amongst a growing number of high-rises lining Meridian Street, the staff affectionately referred to the office as “Shepherd Tower.” Coincidentally, today Shepherd’s home office is across the street at one of those true Meridian Street towers.

After graduating from Ohio State University with a golf scholarship, Jeff Kweder forwent qualifications for a PGA Tour card and joined Dave as Shepherd’s first sales advisor. His nickname, Q-Man, was coined as a result of people mistaking the spelling of his last name. A beat-up, ’77 Chevy with a touch of rust was his signing bonus. Today Jeff serves as Shepherd’s president and partner.

With great enthusiasm and pride, Shepherd relocates a few blocks away from their garage on Meridian Street into a 1,000 square foot office fit to house 6 people.  

Shelby Howard was our first client to take a risk on our Shepherd Shield products. The Shepherd Shield was designed to wrap all necessary insurance and financial products into a single solution. Shelby Howard, a visionary, quickly grasped our concept and directed us to become specialists in the truck dealership industry. Shelby would go on to be one of Dave’s best friends as they both watched their businesses grow side-by-side.    

Requiring more room and anticipating further growth, Dave buys land and builds a 10,000 square foot office building located at 1200 W Carmel Drive. At the time of the ribbon-cutting ceremony, the 10-person staff occupied only half of the space. However nearly five years later, Shepherd would grow to inhabit the entire building.  

Shepherd Insurance wins its first Agency of the Year award, from the Independent Insurance Agents Association, based on Trusted Choice® advisors criteria. It came as a complete surprise, most of those nominated for these awards had several insurance companies to compete with. At the time Shepherd only had but a few. It was this awared that inspired Shepherd to grow as a true independent agency. By now, many of the Shepherd Insurance innovations had been replicated by independent insurance agencies across the nation. This distinction was given to Shepherd in recognition of its ability to deliver value to customers through strong insurance product expertise and its responsive service culture.

National Underwriter magazine recognizes Shepherd as a top agency in the United States. This distinction was given in recognition of our teamwork and client-focused philosophy. Receiving this honor marks the agency’s first national recognition.

2005 birthed Shepherd’s first successful merger & acquisition. Today Shepherd Insurance Evansville remains one of the top performing Shepherd agencies.

The agency’s strong growth and crowd appeal catch the interest of nationally recognized magazine Rough Notes. Featured in the August 2007 cover story “Insurance.”

To solidify benefits offerings, Shepherd Insurance and DeTrude & Company join forces to launch a new employee benefits division.

The expansion of Shepherd Insurance continues with the acquisitions. Drew Denny, Certified Financial Planner™ and Certified 401k Professional, joins the team along with the highly respected Dirk James Agency. The two offices merge and become the fourth Shepherd Insurance location. A sentimental accomplishment indeed, as Dave Shepherd’s family roots trace back to Columbus, Indiana.

Attaining its fourth branch office, Shepherd acquires Hancock county’s largest agency in Greenfield. Dating back to the early 1900s, the agency was once known as “Wood Brothers Insurance.” With the birth of Pence Brooks & Shepherd Insurance, a tidal wave of expertise boosts the company’s value.

Quinn Shepherd started an initiative to encourage Shepherd and its staff to give back to our local communities. Each employee is given two full days off of work each year to volunteer with the organization of their choice. We have also had multiple company wide initiatives to benefit organizations like Prevail, Alzheimer’s Association, Turning Point, Humane Society for Hamilton County, United Hope Foundation, Wisdom & Grace Ministries, Susan G. Komen, American Heart Association, Riley Children’s Hospital, and many more. Learn more about Operation Shepherding.

Twenty-five years after Dave and his dad William “Coach Bill” Shepherd had sold their first life insurance policy, the agency had grown to over 100 employees. Requiring yet again more space, Shepherd Insurance moves into its new headquarters at 111 Congressional Boulevard in Carmel. The office more than doubles the space of the prior location to over 30,000 square feet. A crowning achievement for Dave, who from his garage office in the early 80s, had promised his young daughter Kelly that one day they would move into the “big building” across the street.

Chappell Insurance became part of Shepherd in 2012, with Ray Chappell moving into the Carmel headquarters to help lead the Personal Lines department.

Led by Deirdre Fisher, family-owned Fisher & Associates agency of Noblesville joined Shepherd marking our sixth branch expansion. This December 2013 merger moved the company’s Midwest reach into the heart of Hamilton County.

In 2014, F.C. Tucker Company, the largest independent real estate firm in Indiana, and Shepherd entered into an exclusive relationship and began doing business as Tucker Shepherd Insurance. Two of the oldest and most reputable family-owned companies in Indiana both strengthen their client service even further by offering their services to each other’s clients and employees.

David Shepherd and Rex Early joined forces when Shepherd brought on Consolidated Insurance Services, one of Indiana’s largest independent insurance agencies at the time. By teaming with Consolidated, Shepherd added extensive experience in motorsports, residential property, and hospitality risks.

For the second time, the Independent Insurance Agents Association (or Big “I”) selected Shepherd as the 2014 Agency of the Year, an award presented to an agency that exemplifies leadership and innovation in the insurance industry. Shepherd also earned the Agency of the Year Award in 2003.

Bill Bolander and his team from Bolander Ianni Insurance  joinsed Shepherd’s Greenfield team in April 2015.

Al Purmort, Jr. Patrick Del Medico, and their team of 25 at Al Purmort Insurance joined Shepherd, marking our eleventh branch expansion at the time. The January 2016 Merger moved the company’s reach into southern Florida.

2018, 2017, 2016, 2015, 2014 Shepherd is named to Inc. magazine’s prestigious Inc. 5000 list, an exclusive ranking of the America’s fastest-growing private companies.