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Business Details
19 Years
experience
Trusted Fee-Only Financial Planning in Bend & Chicago
Costello Financial Planning is a family-owned fiduciary fee-only financial planning firm established in 2007. We operate from Bend, Oregon, and Chicago, Illinois, serving clients with a commitment to treating them like family. Our team includes Certified Financial Planner Rob Costello and Certified Public Accountant Paul Costello, who bring decades of combined expertise in finance and tax strategy. We specialize in comprehensive financial planning, asset management, tax optimization, and estate planning, prioritizing evidence-based strategies aligned with client goals. Our fee-only structure eliminates conflicts of interest, ensuring advice is always in clients' best interests.

We focus on building long-term relationships through transparency, personalized coaching, and a consultative process that addresses unique financial needs. Our approach has helped clients navigate market volatility, including the 2008 financial crisis, while maintaining a disciplined investment strategy. We collaborate with external professionals like accountants and estate attorneys to ensure holistic financial solutions. Our philosophy remains rooted in integrity, client-centric service, and the belief that trust is the foundation of lasting financial partnerships.
Services
Financial Planning Asset Management Tax Optimization Estate Planning Retirement Plans
Details
  • Year established: 2007
Highlights and features
  • We are fiduciary advisors with a fee-only structure ensuring unbiased advice.
  • Our team includes Certified Financial Planners and CPAs with decades of experience.
  • We treat clients like family, prioritizing long-term relationships over transactions.
  • We offer transparent pricing with no hidden fees or commission-based products.
  • Our evidence-based strategies have guided clients through market downturns since 2007.
Services
Financial Planning
We develop personalized financial plans aligned with clients' life goals and risk tolerance. Our process includes analyzing cash flow, investment portfolios, tax strategies, and retirement timelines. By combining behavioral coaching with evidence-based research, we help clients make informed decisions that adapt to changing life circumstances while maintaining long-term financial discipline.
Asset Management
Our asset management focuses on constructing diversified portfolios using Dimensional Funds and other research-backed investments. We monitor market conditions, rebalance holdings, and adjust allocations based on individual client needs. The approach emphasizes risk management through strategic diversification while maintaining cost efficiency and tax-conscious investment decisions tailored to each client's financial objectives.
Tax Optimization
We implement tax-efficient strategies including asset location planning, income tax mitigation, and philanthropic tax planning. Our services integrate with overall financial plans to minimize tax liabilities across different account types. We collaborate with CPAs to ensure compliance while maximizing after-tax returns through proactive tax planning integrated with investment and estate strategies.
Estate Planning
Our estate planning services address wealth distribution, guardianship, and family values preservation. We coordinate with estate attorneys to create tax-efficient transfer strategies, charitable giving plans, and intergenerational wealth frameworks. The process includes developing family mission statements and educational programs to prepare heirs for responsible financial stewardship of inherited assets.
Retirement Plans
We offer customized retirement plan solutions for businesses, including 401(k) and pension plans. Services cover plan design, administration, and participant education. Our fee-based structure allows flexibility in cost allocation between employers and employees. We focus on fiduciary compliance, investment selection, and ongoing monitoring to ensure plans meet both employer objectives and employee needs.
People
Rob Costello
Founder
Certified Financial Planner with over 10 years of experience. Graduated from University of Illinois with finance degree and CPA preparation from Northwestern. Focuses on aligning life goals with financial strategies while emphasizing family values and long-term planning.
Paul Costello
Partner
CPA and Series 65 licensed professional managing Chicago operations. Former Deutsche Bank Vice President with expertise in financial markets and tax strategies. Combines accounting background with investment advisory skills to deliver comprehensive financial solutions for clients.
Phil Costello
Operations Manager
Business degree holder from DePaul University managing back-office operations. Brings IT expertise from healthcare and nonprofit sectors to streamline financial planning processes. Focuses on data management and technology integration to enhance client service delivery efficiency.
Questions
What are your fee structures?
We use asset-based fees (0.99% first $1M, 0.89% next $1M) or flat fees depending on complexity. Minimum quarterly fee is $2,500.
Do you have account minimums?
Yes, $1,000,000+ total account size. Exceptions considered for high-income earners and business owners.
Are you a fiduciary?
Yes, we're fiduciary fee-only advisors with no product sales or commissions. Always acting in clients' best interests.
What custodian do you recommend?
We recommend Charles Schwab as custodian for asset safety and transparency. Clients maintain direct ownership of their accounts.
How do you approach investment planning?
We use evidence-based strategies with Dimensional Funds, focusing on risk management, diversification, and behavioral coaching through market cycles.
Reviews (1)
Von Miller
Dec 25, 2021 Report
My wife and I have been using Costello Financial Planning for almost 5 years now and have been extremely satisfied with their services. We have a fairly complicated financial life and Rob Costello has been a tremendous help in helping us organize all of the moving parts into a comprehensive financial plan to achieve all of our life goals. His services go way beyond just asset allocation and portfolio management. He is also very knowledgeable about estate planning, insurance needs, saving for college, business planning and retirement planning - and he takes a holistic approach to make sure that