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.

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? TCJA Extension

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 |2026-10-01T10:49:32-04:00May 1st, 2026|Estate Planning, Weekly Update|Comments Off on Did You Rush Your Estate Plan? TCJA Extension

Private Equity Payouts: How to Avoid a Surprise Tax Bill

Private Equity Payouts: How to Avoid a Surprise Tax Bill By Scott Searles A private equity payout often represents years of work coming together. It also tends to introduce [...]

By |2026-04-24T10:18:17-04:00April 16th, 2026|Retirement Blog, Weekly Update|Comments Off on Private Equity Payouts: How to Avoid a Surprise Tax Bill

What Your 2025 Tax Return Reveals About Your Retirement Plan

What Your 2025 Tax Return Reveals About Your Retirement Plan Scott Searles  |  April 3rd, 2026 Many tax returns are filed, signed, and promptly forgotten. Which is unfortunate—because they [...]

By |2026-08-04T13:09:23-04:00April 10th, 2026|Retirement Blog, Weekly Update|Comments Off on What Your 2025 Tax Return Reveals About Your Retirement Plan

Roth Conversions in a Volatile Market: Opportunity or Risk?

Roth Conversions in a Volatile Market: Opportunity or Risk? By Scott Searles |  April 10th, 2026 Market declines tend to trigger two reactions: concern and hesitation. Less commonly, they [...]

By |2026-07-21T13:59:20-04:00April 2nd, 2026|Retirement Blog, Weekly Update|1 Comment

Retirement Preparedness in 2026: Planning for Longer Lives, Rising Healthcare Costs, and Income Volatility

Retirement Preparedness in 2026: Planning for Longer Lives, Rising Healthcare Costs, and Income Volatility Retirement used to be a 10–15 year chapter. For many families today, it may last [...]

By |2026-03-24T10:17:20-04:00March 20th, 2026|Retirement Blog, Weekly Update|Comments Off on Retirement Preparedness in 2026: Planning for Longer Lives, Rising Healthcare Costs, and Income Volatility

Supreme Court Tariff Ruling: Key Takeaways for Investors

Supreme Court Tariff Ruling: Key Takeaways for Investors by Scott Searles  |  March 13th, 2026 After nearly a year of trade policy uncertainty, the Supreme Court's ruling that recent [...]

By |2026-08-05T09:04:41-04:00March 13th, 2026|Retirement Blog, Weekly Update|Comments Off on Supreme Court Tariff Ruling: Key Takeaways for Investors

2026 Retirement Plan Contribution Limits: What the New Numbers Mean for Your Strategy

2026 Retirement Plan Contribution Limits: What the New Numbers Mean for Your Strategy by Scott Searles | March 6th, 2026 Each year, the IRS adjusts retirement plan contribution limits [...]

By |2026-07-21T14:21:38-04:00March 6th, 2026|Retirement Blog, Weekly Update|2 Comments
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