About Scott Searles

Serving clients primarily in Ohio and Florida, Scott is the owner of Skybox Financial Group, where, as a knowledgeable and experienced professional, he helps clients plan for their financial future.

Giving to Charity in 2026? The Tax Rules Changed

Giving to Charity in 2026? The Tax Rules Changed—Here’s What Retirees Should Know Before Year-End By Scott Searles  |  October 16th, 2026 For many retirees, charitable giving isn’t simply [...]

By |2026-10-15T15:58:17-04:00October 16th, 2026|Tax Strategies Series, Weekly Update|0 Comments

Medicare Open Enrollment Is Almost Here

Medicare Open Enrollment Is Almost Here: 7 Things Retirees Should Review Before They Renew Anything By Scott Searles  |  October 9th, 2026 Medicare Open Enrollment begins October 15 and [...]

By |2026-10-08T14:33:35-04:00October 8th, 2026|Retirement Blog, Weekly Update|Comments Off on Medicare Open Enrollment Is Almost Here

AI Can Answer Financial Questions, Should It Build Your Financial Plan?

AI Can Answer Financial Questions. But Should It Build Your Financial Plan? By Scott Searles  |  October 2, 2026 Artificial intelligence can do some remarkable things. It can explain [...]

By |2026-10-01T16:03:11-04:00October 2nd, 2026|Retirement Blog, Weekly Update|Comments Off on AI Can Answer Financial Questions, Should It Build Your Financial Plan?

5 Tax Decisions Retirees Should Review Before the End of 2026

Don’t Wait Until December: 5 Tax Decisions Retirees Should Review Before the End of 2026 By Scott Searles  |  September 11th, 2026 December gets most of the attention when [...]

By |2026-09-18T15:23:18-04:00September 11th, 2026|Tax Strategies Series, Weekly Update|Comments Off on 5 Tax Decisions Retirees Should Review Before the End of 2026

You Sold the Business. Now What? Avoiding the “Second Mistake”

You Sold the Business. Now What? Avoiding the “Second Mistake” by Scott Searles  |  August 14th, 2026 Selling a business can feel like crossing the finish line after years—or [...]

By |2026-08-13T18:59:41-04:00August 14th, 2026|Weekly Update|Comments Off on You Sold the Business. Now What? Avoiding the “Second Mistake”
Go to Top