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.

You’ve Built the Wealth. Now It’s Time to Protect It.

You’ve Built the Wealth. Now It’s Time to Protect It. Wealth Preservation Strategies By Scott Searles  |  July 10, 2026 For decades, your financial life may have centered around [...]

By |2026-07-14T16:40:30-04:00July 10th, 2026|Retirement Blog, Weekly Update|0 Comments

Is the AI Investment Boom Creating Opportunity or Excess?

Is the AI Investment Boom Creating Opportunity or Excess?  What Long-Term Investors Should Consider  By Scott Searles  |  June 26th, 2026 Artificial intelligence has become one of the largest [...]

By |2026-07-07T10:13:59-04:00June 26th, 2026|Retirement Blog, Weekly Update|Comments Off on Is the AI Investment Boom Creating Opportunity or Excess?

What the Markets Have Taught Retirees So Far in 2026

What the Markets Have Taught Retirees So Far in 2026 By Scott Searles  |  June 19th, 2026 If the first half of 2026 has taught retirees anything, it is [...]

By |2026-06-18T15:05:52-04:00June 18th, 2026|Retirement Blog, Weekly Update|Comments Off on What the Markets Have Taught Retirees So Far in 2026

Selling Your Business in an Uncertain Tax Environment

Selling Your Business in an Uncertain Tax Environment: 5 Planning Moves to Consider Before You Sign an LOI By Scott Searles  |  June 12, 2026 For many business owners, [...]

By |2026-06-11T13:18:12-04:00June 12th, 2026|Retirement Blog, Weekly Update|Comments Off on Selling Your Business in an Uncertain Tax Environment

Retirement Wasn’t Supposed to Look Like This: Planning for Retirement as a Single Woman

Retirement Wasn't Supposed to Look Like This: Planning for Retirement as a Single Woman By Scott Searles  |  June 5, 2026 For many women, retirement does not unfold exactly [...]

By |2026-06-04T16:57:18-04:00June 5th, 2026|Retirement Blog, Weekly Update|Comments Off on Retirement Wasn’t Supposed to Look Like This: Planning for Retirement as a Single Woman

Are You on Pace for an Unexpected Medicare IRMAA Surcharge?

Are You on Pace for an Unexpected Medicare IRMAA Surcharge? By Scott Searles  |  May 29th, 2026 Many affluent retirees are surprised to learn that Medicare premiums are not [...]

By |2026-05-29T15:55:34-04:00May 29th, 2026|Retirement Blog, Weekly Update|Comments Off on Are You on Pace for an Unexpected Medicare IRMAA Surcharge?

The Biggest Risk to Your Retirement Plan Isn’t the Market, It’s Decision Fatigue

The Biggest Risk to Your Retirement Plan Isn’t the Market, It's Decision Fatigue By Scott Searles  |  May 22nd, 2026 Too Many Choices, Not Enough Clarity We live in [...]

By |2026-05-21T16:49:00-04:00May 22nd, 2026|Retirement Blog, Weekly Update|Comments Off on The Biggest Risk to Your Retirement Plan Isn’t the Market, It’s Decision Fatigue

The 5-Year Window Before Retirement: Where Small Decisions Can Have a Big Impact

The 5-Year Window Before Retirement: Where Small Decisions Can Have a Big Impact By Scott Searles  |  May 15th, 2026 There’s a common assumption that retirement planning is about [...]

By |2026-05-13T16:22:03-04:00May 15th, 2026|Retirement Blog, Weekly Update|Comments Off on The 5-Year Window Before Retirement: Where Small Decisions Can Have a Big Impact

Retiring in an Uncertain Market: Why Income Strategy Matters More Than Market Timing

Retiring in an Uncertain Market: Why Income Strategy Matters More Than Market Timing By Scott Searles  |  May 8th, 2026 The Wrong Question Most Retirees Are Asking When markets [...]

By |2026-05-08T15:28:55-04:00May 8th, 2026|Retirement Blog, Weekly Update|Comments Off on Retiring in an Uncertain Market: Why Income Strategy Matters More Than Market Timing

Did You Rush Your Estate Plan? What the TCJA Extension Means for High-Net-Worth Families

Did You Rush Your Estate Plan? What the TCJA Extension Means for High-Net-Worth Families  by Scott Searles  |  May 1st, 2026 When the Deadline Disappears, So Does the Pressure—Or [...]

By |2026-05-01T13:55:22-04:00May 1st, 2026|Retirement Blog, Weekly Update|Comments Off on Did You Rush Your Estate Plan? What the TCJA Extension Means for High-Net-Worth Families
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