Our History

In 1977, upon his graduation from the University of Mississippi, David Shepherd returned to Carmel, Indiana, and started his insurance agency. Almost four decades later, Shepherd Insurance has grown into the largest personal line insurer in Indiana, with over 170 employees and nine offices across the state. Dave's simple vision has also remained the same: to be a trusted advisor who helps people protect their families and property and give over-attentive service while doing it. Shepherd Insurance specializes in both personal and commercial insurance and employee benefits.

In response to more client requests, Shepherd Insurance started offering financially related consulting services that provided more solutions to our clients in 2002. In order to demonstrate our commitment to consulting with retirement plans and individual clients, at the beginning of 2015, a new separate entity was created. Shepherd Financial was established by a merger of our existing staff and a team of very talented outside individuals.

Today, Shepherd Financial is an independent wealth advisory consulting firm serving mainly corporate retirement plans and select individuals. Adhering to process-driven model of providing unbiased and objective advice from a team of talented professionals with over 125 years of combined experience allows us to manage over $700 million of our clients' assets.

1977

1977

An Agency is Born
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 get their start selling life and disability insurance for Franklin Life. Every family member and friend is a potential prospect.

1983

1983

Jeff Kweder Arrives
Foregoing qualifications for a PGA Tour card, Jeff Kweder joins Dave as a sales agent. Jeff's ability to forecast industry trends and capture opportunities quickly earns him the distinction as the company's numbers guy. His nickname, Q-Man, is coined as a result of people mistaking the spelling of his last name.

A beat-up, '77 Chevy with a touch of rust is his signing bonus.

1988

1988

Steve Wylam Begins at Capital Analysts of the Midwest
Upon graduation from Purdue University, Steve Wylam starts a 26 year career with Capital Analysts of the Midwest, providing total financial planning for individual clients and later branching out to serve the needs of corporate retirement plans and their participants.

1993

1993

A Commitment to Excellence
Steve receives his CERTIFIED FINANCIAL PLANNER (CFP®) certification from the Certified Financial Planner Board of Standards. The CFP® Board is an independent professional regulatory organization acting to benefit and protect the public in its dealings with persons engaged in providing financial advice.

1996

1996

A First of Many to Come
Looking for a way to take better care of his employees, the owner of an automotive dealership hires Steve to help with his corporate retirement plan. The outstanding service he has received through the years is why he remains a valued client today.

1997

1997

Drew Denny Enters the Industry
As a graduate of the Indiana University Kelley School of Business, Drew joins and later partners with his father as Denny & Company in the family retirement plan and insurance business.

2002

2002

Teaching the Next Generation
As a Limited Term Professor at Purdue University teaching Ethics and Compliance in Financial Planning to upperclassmen, Steve meets an outstanding student with a tremendous future in the business - Tom Mayer.

2004

2004

Tom Mayer Partners with Steve Wylam
Tom joins Steve in Indianapolis, and the two of them form the 401K TEAM @ CAMI. Through outstanding service to their corporate retirement plan clients, they achieve a 100% client retention rate for the next 10 years.

2006

2006

Ron D’Onofrio Joins Shepherd
In the life insurance industry since 1980 in both sales and management, Ron D’Onofrio joins Shepherd Insurance to offer a more specialized approach and comprehensive solution for the firm’s financial services clientele.

2007

2007

Enhancing Knowledge for our Clients
Steve and Tom both acquire the Accredited Investment Fiduciary (AIF®) designation from the Certified Financial Planner Board of Standards.

2010

2010

Drew Denny Joins Shepherd Insurance & Financial Services
The expansion of Shepherd Insurance continues with the acquisition of Denny & Company. Drew joins the team and increases the firm's presence in corporate retirement plans.

2013

2013

Continuing the Pursuit of Industry Knowledge
Drew obtains the Certified 401(k) Professional - C(k)P designation from The Retirement Advisor University in conjunction with the UCLA Anderson School of Management. This designation represents the pinnacle of achievement for the professional Retirement Plan Advisor, recognizing a combination of substantial practical retirement plan management experience and the completion of a comprehensive and highly specialized educational program.

2015

2015

Shepherd Financial is Established
Shepherd Financial is established by a merger of Shepherd Insurance's existing staff and a team of very talented outside individuals from the 401K TEAM @ CAMI. This led to the creation of one of the largest 401(k) consulting firms in the state based upon the number of plans we service, as well as over $600 million of our clients' assets.

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