Who We Serve

At Costello Financial Planning, we work with a limited number of families who want more than investment management. They want a trusted advisor to help coordinate the financial decisions that impact their lives, their families, and their futures.

While Costello Financial Planning is based in Arlington Heights, IL and Burlington, VT, our clients live across the country. Rob's journey from the Chicago area to Ann Arbor, MI to Bend, OR, and ultimately Vermont has reinforced an important lesson: great financial planning isn't limited by geography.

Through secure technology and a structured planning process, we serve families from the East Coast to the West Coast. Clients enjoy the convenience of virtual meetings while still having the opportunity to meet face-to-face during annual visits and special planning sessions.

Our clients typically have between $2 million and $20 million of investable assets and value thoughtful planning, tax efficiency, and a long-term perspective.

Families Approaching Retirement
Retirement is one of the most significant financial transitions you'll ever face.

We help clients answer questions such as:

  • When can I retire?
  • How much can I safely spend?
  • When and how should I complete Roth conversions?
  • How should I claim Social Security?
  • What is the most tax-efficient way to draw income from my portfolio?

Our goal is to help you enter retirement with confidence, clarity, and a plan.

Retirees Seeking Ongoing Guidance
Many of our clients are already retired and want a trusted partner to help them navigate changing markets, tax laws, and life circumstances.

We provide ongoing guidance around:

  • Retirement income planning
  • Tax-efficient withdrawals
  • Portfolio management
  • Required Minimum Distributions (RMDs)
  • Charitable giving strategies
  • Estate planning coordination
  • Family wealth transfer
  • We help ensure your financial plan continues to support the life you want to live.

High-Income Professionals
Successful professionals often face complex decisions around taxes, investments, equity compensation, retirement plans, and cash flow.

  • Optimize retirement savings
  • Reduce unnecessary tax drag
  • Coordinate employer benefits
  • Invest excess cash efficiently
  • Build long-term wealth intentionally
  • Our focus is on helping you make smart financial decisions while staying focused on your career and family.

Business Owners
Business owners often have much of their wealth tied to a single asset—their company.

We help business owners:

  • Coordinate personal and business finances
  • Manage taxes proactively
  • Evaluate retirement plan options
  • Build wealth outside the business
  • Prepare for a future sale or transition
  • Create a succession strategy
  • Our CFP® and CPA perspectives help clients make decisions that consider both financial planning and tax implications.

Families Building Multi-Generational Wealth
As wealth grows, so does complexity.

Many of our clients are focused on ensuring their wealth benefits not only themselves, but future generations.

We help coordinate:

  • Estate planning strategies
  • Family gifting
  • Trust planning discussions
  • Charitable giving
  • Legacy planning
  • Family financial education
  • Our role is to help families make thoughtful decisions that align wealth with purpose.

We May Be a Good Fit If You:

  • Have $2 million or more in investable assets
  • Value a long-term relationship with a trusted advisor
  • Want proactive tax planning alongside investment management
  • Prefer evidence-based investing over market predictions
  • Appreciate straightforward advice and clear communication
  • Are looking for a fiduciary partner who puts your interests first