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.

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|0 Comments

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”

Why August Is the Best Time to Start Year-End Financial Planning

Why August Is the Best Time to Start Year-End Financial Planning by Scott Searles  |  August 7th, 2026 As summer begins winding down, most people aren’t thinking about year-end [...]

By |2026-08-06T15:23:27-04:00August 7th, 2026|Retirement Blog, Weekly Update|Comments Off on Why August Is the Best Time to Start Year-End Financial Planning

The Biggest Retirement Risk Isn’t the Market

The Biggest Retirement Risk Isn’t the Market—It’s Making the Wrong Decisions at the Wrong Time By Scott Searles  |  July 31, 2026 Market volatility receives plenty of attention, especially [...]

By |2026-07-31T10:29:21-04:00July 31st, 2026|Retirement Blog, Weekly Update|Comments Off on The Biggest Retirement Risk Isn’t the Market
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