Skybox Financial Group

07/17/2026

Many people delay retirement because they are waiting for “the right time.”
They hope inflation will settle down. Interest rates will become more predictable. Markets will calm. Tax laws will stop changing.
Unfortunately, retirement has never worked that way. Every generation has retired during uncertainty.

Read more here:

Retiring Into Uncertainty: Why Flexibility May Be Your Greatest Financial Advantage by Scott Searles | July 17th, 2026 Many people delay retirement because they are waiting for “the right time.” They hope inflation will settle down. Interest rates will become more predictable. Markets will calm....

07/10/2026

Whether your wealth came from a successful business, a long career, disciplined investing, or a combination of all three, reaching financial independence is a tremendous accomplishment.

The strategies that help build wealth are often different from the strategies that help preserve it.
Read our blog post on wealth preservation strategies here:

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 one goal: building wealth. You worked hard, saved consistently, invested thoughtfully, and made sacrifices along the way...

07/04/2026

Happy Fourth of July from all of us at Skybox Financial Group!

06/26/2026

Artificial intelligence has become one of the largest investment themes of the decade.
History reminds us that revolutionary technologies often create tremendous opportunities. It also reminds us that even transformational companies can experience periods when expectations outpace reality.
Read more about the AI Investment Boom Here:

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 investment themes of the

06/19/2026

If the first half of 2026 has taught retirees anything, it is that uncertainty never fully disappears.
Read more on the lessons we've learned from 2026's volatile markets here:

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 that uncertainty never fully disappears. Markets have navigated changing economic data, ongoing interest rate discussions, geopolitical headlines, and...

06/12/2026

For many business owners, selling a company represents the largest financial transaction of their lifetime.

Yet surprisingly, many owners spend years building a successful business and only a few weeks preparing for its sale.

Read more on planning moves to consider before selling a business:

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, selling a company represents the largest financial transaction of their lifetime. Yet surprisingly, many owners spend years building a...

06/05/2026

Some enter retirement after the loss of a spouse.
Others experience divorce later in life.
Some simply find themselves approaching retirement on their own after years of building a career, raising a family, or caring for loved ones.
Read more about retiring as a single woman below

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 as expected. Some enter retirement after the loss of a spouse. Others experience divorce later in life. Some simply find themselv...

05/30/2026

Read our latest blog post on Medicare IRMAA surcharges

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 the same for everyone. If your income crosses certain thresholds, you may pay an additional surcharge called IRMAA, or the Income...

05/15/2026

Did you know the 5 years before retirement might be the most important?
It’s not just about saving—it’s about making the right decisions at the right time.
If retirement is on your horizon, this is worth a read 👇

Skybox Financial Group is a registered investment adviser located in Middleburg Heights, Ohio. Skybox Financial Group may only transact business in those states in which it is registered, or qualifies for an exemption or exclusion from registration requirements. Skybox Financial Group’s web site i...