Who We Are

Stewart Ogilby


Before moving to Florida in 1986 Stewart owned and managed an agency having its main office in Worthington, Ohio that focused on low-cost term life-insurance, annuities, and (before TEFTA) non-registered tax-shelter investments. Licensed in Ohio since 1975, as one of the country's leading marketing directors with Denver's Multi-Financial Corporation he hired, trained, and supervised 34 agents working from three offices in the Columbus, Ohio area.

Having grown up on a family farm in Hudson, Ohio he was employed by corporations for 16 years following having worked his way throuth Ohio State University and having earned a BS degree. Afer achieving top management positions, he decided to go into business for himself.

In 1980 he wrote a landmark consumer-oriented trade-book directed toward life-insurance agents. Advertised and receiving favorable reviews in Life Insurance Selling Magazine, thousands of copies were sold nationally.

The bulk of his experience has been in using low-cost term life-insurance and selected fixed annuities. In 2014 he decided to pick up a Series 65, enabling him to examine and critique stock, bonds, and other securities held by his clients. If you haven't watched this before, learn: The Difference Between a Broker and a FIDUCIARY

Stewart's primary goal today is to help persons who are retired (or who are planning their retirement) protect assets and incomes in today's problematical financial environment. He enjoys helping working persons and their families, as well as advising persons who have inherited assets that they intend to protect and grow in value.

Stewart has never been sued, censored, or been the subject of any regulatory investigation or disciplinary action.

He has been on the faculty advisory committee of Manatee Technical Instutute, a member of the Citizens Advisory Committee of WSLR Radio, a long-time member of Manasota Mensa, an active member of the Sarasota Sailing Squadron, and is a Founding and Sustaining member of WSMR, the outstanding classical music radio station in Sarasota (89.1 FM) and in Tampa (103.9 FM).

Sherri Urfer
Sherri Urfer


Executive Administrator

Sherri Urfer has worked with Stewart Ogilby for a number of years. Before home values crashed in 2008, together they facilitated transferring millions of dollars of what Stewart called "phantom equity" into senior homeowners' bank accounts. Substantial cash proceeds improved retirement finances for hundreds of seniors throughout Florida. Mortgaged homes of many cash-strapped seniors were saved from foreclosure. Homeowners retained title to their properties and mortgage payments were permanently eliminated.

Although home prices had soared many eligible elderly persons hesitated, years ago, to consider reverse mortgaging despite the fact that doing so would have been life-saving for them financially. At the time, many uninformed persons were calling reverse mortgages "risky" or "controversial". Today reverse mortgages are used, when appropriate, as standard financial planning tools.

Sherri holds Florida's 2-14 insurance license and handles applications, underwriting, and paperwork involving annuities and life-insurance, products that supplement, when appropriate, portfolio investments. Also a Florida licensed real-estate sales agent, Sherri is familiar with the local housing market.

Originally from Michigan, Sherri has been a Sarasota area resident since 1975. She is the mother of three grown children.


Phillip G. Day
Phillip G. Day


Attorney, Accountant, Certified Financial Planer

Phil brings a unique background to his clientele in what he calls the “triangular” approach to client service: utilizing his professional credentials in law, accounting, and financial services including his academic achievements.

He represents his clients with professionalism and compassion in all matters, whether substantial or modest, complex or simple. The foundation for his success is not only his knowledge and expertise in the law, but also in his ability to build personal relationships with his clients.

Before beginning his own practice, Phil worked as an attorney with a large and prestigious law firm in Tampa, a “Big Six” accounting firm, a multi-million dollar closely held family business and a large and highly recognized national bank.

The needs of clients are varied and Phil prides himself on giving each client the confidence that he or she will be well advised. In addition to acting as a client advocate, Phil also serves as trusted advisor and friend. His clients soon learn that they can turn to a single source for thoughtful, well-informed guidance.

Dave Silver
Dave Silver


Medicare and health-insurance agent

Dave Silver specializes in working with people who have Medicare, or about to get Medicare in the State of Florida. The focus of Dave's practice is Medicare.

Dave has helped thousands of people in this area. His overall knowledge of Medicare and specialized experience separates him from the majority of other health insurance agents. In giving seniors the facts, he strives to keep things simple to eliminate the confusion of Medicare while offering objective advice.

Dave been a resident of Florida for over 15 years. He and his wife, Tami, and son, Jack, live in Lakewood Ranch.

* Affiliates are individuals with whom we associate who may be contacted to independently provide professional services for clients of Wisebird Financial Group. It is understood that clients are encouraged to do their own due diligence on each and every affiliate. The reputation of none of the parties reflects positively or negatively on another party's reputation or quality of service.

How We Work For You

This website is provided for informational purposes only and is not intended to provide any tax, legal, financial planning, insurance, accounting, investment, or any other kind of professional advice or services. Nothing on this website should be construed as an offer to sell or a recommendation for any security, insurance policy, or investment strategy. For your information this Website may provide links to other websites that are not operated by Stewart Ogilby. Those links do not mean that Stewart Ogilby necessarily endorses, approves, or sponsors any products or information available at the linked site. Before purchasing any financial product be sure to do your own due diligence and you should consult with an appropriate tax or legal professional before taking action based on any suggestions or information on this site. You alone are solely responsible for determining whether any financial or insurance strategy, product or service, is appropriate or suitable for you based on your investment objectives and personal and financial situation. By contacting Stewart Ogilby you may be offered insurance products by an agent licensed in your state. Annuity product guarantees rely on the financial strength and claims-paying ability of the issuing insurer. Annuity riders may be available for an additional annual premium that can provide additional benefits and income guarantees.