Upcoming Webinar:
Webinar:
Top 5 Mistakes People Make with Medicare
October 28, 2025
|
12:00 pm
ET
&
ET
October 28, 2025
About the event
Who Should Attend:
Pre-Retirees and those 65+Â new to Medicare
Business Owners with employees over age 65
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Don’t miss this impactful session on what you need to know in planning for and enrolling in Medicare.
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We’ll answer questions like:
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- How to understand and choose the right Medicare options (in less than 10 minutes)?
- What is IRRMA and how can I manage my income to keep my Medicare premiums low?
- What do I need to watch out for during annual enrollment if I am already enrolled?
- When and how do I enroll and does that change if IÂ am still working?
- Should I consider Medicare Advantage or Medicare Supplement Plans?
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PLUS:

Retirees: Learn the top 5 mistakes you absolutely want to avoid.
Business owners: See how you might save money on your health insurance plan.
Meet the Speakers
Andrew Leithe, CFP®
CEO & Investment Committee Chair
- 15+ years guiding successful business owners, physicians, and executives
- Oversees $400M+ in client assets (as of 9/30/2025)
- Leads Strategic Financial’s Investment Committee
- Specialist in Business Consulting, Tax Strategy, and Generational Wealth Planning
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Andrew brings a practical, client-first approach to business planning, combining deep tax knowledge with real-world insight into how to grow and protect value across every stage of ownership.
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His career started in private equity, asset management, quantitative analysis and marketing with Frontpoint Partners (as seen in “The Big Short”), JP Morgan, Apollo Global Management, and Siguler Guff & Company. Today he applies that expertise, along with a unique and rigorous financial planning process, in his work as the private wealth strategist for our individual and business clients.
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His approach ensures that all areas of our clients’ business and personal finances stay well connected and aligned.
Andrew Leithe, CFP®
CEO & Investment Committee Chair
- 15+ years guiding successful business owners, physicians, and executives
- Oversees $400M+ in client assets (as of 9/30/2025)
- Leads Strategic Financial’s Investment Committee
- Specialist in Business Consulting, Tax Strategy, and Generational Wealth Planning
‍
Andrew brings a practical, client-first approach to business planning, combining deep tax knowledge with real-world insight into how to grow and protect value across every stage of ownership.
‍
His career started in private equity, asset management, quantitative analysis and marketing with Frontpoint Partners (as seen in “The Big Short”), JP Morgan, Apollo Global Management, and Siguler Guff & Company. Today he applies that expertise, along with a unique and rigorous financial planning process, in his work as the private wealth strategist for our individual and business clients.
‍
His approach ensures that all areas of our clients’ business and personal finances stay well connected and aligned.
Bill Webb – Saratoga Medicare Advisors
Special Guest Speaker
Bill Webb is a Managing Partner of Saratoga Benefit Services and the Owner of Saratoga Medicare Advisors. Â Prior to joining Saratoga, Bill worked for Arthur J. Gallagher on the Property & Casualty side of the insurance industry.
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Bill joined his mother at Saratoga Benefits in August of 2017 to learn and expand their benefits firm.
Bill started Saratoga Medicare Advisors as a sister company to Saratoga Benefits in 2021 after noticing a lack of resources for seniors and an opportunity to help an under-served population of individuals through a difficult transition to Medicare.
Over the past 4 years, Bill has helped hundreds of individuals nation-wide understand their costs, timelines, and options with Medicare.
Osaic Wealth Form CRS
Securities and investment advisory services are offered through Osaic Wealth, Inc., member FINRA/SIPC and a registered investment advisor. Additional investment advisory services offered through Strategic Financial Advisors Corporation, a registered investment advisor. Â Strategic Financial Advisors Corporation and Strategic Financial Services Corporation are not affiliated with Osaic Wealth, Inc.
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