Aspen Wealth Management

Meet Jacob Squires, a Financial Planning Associate and Portfolio Trader at Aspen Wealth Management.

Working closely with our Chief Investment Officer, Jacob supports both the planning and investment teams, from building financial plans and conducting research to executing trades and overseeing portfolio implementation. He brings more than a decade of professional experience and has completed all three levels of the CFA® Program.

Jacob grew up in a hardworking Missouri farm family, and that upbringing shaped how he approaches his work: preparation, stewardship, and long-term thinking. He believes great planning goes beyond the numbers and starts with trust and clear communication.

Get to know Jacob: https://www.aspenwealthmgmt.com/team/jacob-squires-financial-planning-associate

April is when you find out what your tax year cost you. Right now, you can still do something about it.

There’s still time to check your withholding, look for tax-loss harvesting opportunities, consider bundling charitable gifts through a donor-advised fund, or evaluate whether a Roth conversion makes sense this year.

The difference between tax preparation and tax planning comes down to timing. One records what already happened. The other lets you shape it.

Read the strategies: https://www.aspenwealthmgmt.com/resource-center/tax/mid-year-tax-planning-strategies

In 1930, U.S. life expectancy was under 60. A retirement program that paid out at 65 didn't have to stretch far. Today, life expectancy is closer to 80, and a healthy 60-year-old may have two active decades ahead, sometimes more.

That shift creates what's known as longevity risk: the possibility of outliving your money. More years in retirement mean more income needed, plus rising healthcare costs, potential long-term care, and inflation quietly eroding purchasing power along the way.

Planning for it means building an income floor, extending the payout period, accounting for sequence-of-returns risk, and keeping part of your portfolio positioned for growth.

Read the full breakdown: https://www.aspenwealthmgmt.com/resource-center/retirement/longevity-risk-financial-security

Should you still be buying stocks at record highs? It's the question Nathan Davis, CFP®, CFA, our Chief Investment Officer, has heard more than any other lately, and it anchors our Q2 2026 market update.

Rather than run through every headline, Nathan built the hour around what clients are actually asking. Is the economy cooling or breaking? Are stocks too expensive to own? And where are investors being rewarded today?

His throughline: a record high tells you where the market has been, not where it's going.

The full replay is up now.

Watch here: https://bit.ly/4hXUs7Y

Cornelius Vanderbilt's reported last words to his heirs: "Keep the money together." Within three or four generations, one of the largest fortunes in America had largely dissipated.

John D. Rockefeller took a different path. He educated his heirs, established a governance structure, and designed legal frameworks to promote tax efficiency and continued growth. Generations later, that legacy continues to support causes in medicine, education, and global health.

The difference wasn't the size of the fortune. It was the preparation of the people who would inherit it. With an estimated $124 trillion in wealth expected to change hands over the next few decades, that lesson is worth sitting with.

Read the full article:

"Keep the Money Together": Preparing the Next Generation for Financial Leadership | Aspen Wealth Management Preserve your family’s fortune and philanthropic legacy with strategies in next generation planning and financial leadership, inspired by the lessons of Vanderbilt and Rockefeller.

You’ve spent a lifetime building a successful business, but it’s time to step back. How do you know if your business is ready to sell? What are the next steps in your exit plan? What about taxes? Senior Wealth Advisor Jim Davis answers these questions, and more.

Building Exit Readiness: Are Your Truly Prepared to Sell? | Aspen Wealth Management Selling your business is a huge life event. Learn the key financial, tax, and emotional factors that determine whether you're truly prepared.

Replacing your paycheck in retirement is one of the most complex financial challenges you’ll face. Learn how income sequencing—the order in which you draw from accounts—affects your taxes, longevity risk, and lifestyle. Troy Fore, CFP® explains.

Building Your Retirement Paycheck: Income Sequencing Strategies for the First Years of Retirement | Aspen Wealth Management A thoughtful retirement income sequencing strategy can help manage taxes, longevity risk, and cash flow while providing greater flexibility.