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Your Trusted Financial Partner in San Diego
High Bluff Private Wealth has been dedicated to providing comprehensive financial planning and wealth management services since our founding. Our team of seasoned professionals specializes in addressing the unique needs of business owners and corporate executives, offering tailored solutions that integrate personal and professional financial goals. With decades of collective experience, we focus on succession planning, retirement strategies, tax optimization, and estate planning, ensuring our clients can concentrate on growing their businesses while we manage their financial futures.

Our commitment to personalized service, combined with a disciplined approach to wealth management, allows us to build lasting relationships grounded in trust and transparency. We pride ourselves on staying ahead of industry trends and leveraging advanced strategies to help clients navigate complex financial landscapes. Through community engagement and a client-first philosophy, we strive to make a meaningful impact on both individual lives and the broader San Diego community.
Services
Financial Planning Investment Management Retirement Planning Estate Planning Business Succession Tax Strategies Insurance Review Education Planning Executive Benefits Charitable Planning
Highlights and features
  • We offer over 60 years of combined experience in financial planning for business owners.
  • Our team specializes in complex retirement and estate planning strategies.
  • We provide personalized tax optimization techniques tailored to executive compensation.
  • Our disciplined investment management approach prioritizes long-term wealth preservation.
  • We maintain transparency through regular client education and portfolio reviews.
Associations and certifications
  • FINRA
  • SIPC
Services
Financial Planning
Our financial planning service creates customized roadmaps integrating business and personal financial goals. We analyze cash flow, risk management, and investment strategies to build comprehensive plans that adapt to life changes. With a focus on long-term growth and tax efficiency, we help clients achieve milestones like retirement, business succession, and legacy planning.
Retirement Planning
We design retirement plans that optimize 401(k)s, IRAs, and qualified plans while addressing tax implications. Our approach includes Social Security optimization, required minimum distribution planning, and Roth conversions. By aligning retirement goals with risk tolerance, we ensure sustainable income streams throughout retirement years.
Estate Planning
Our estate planning service utilizes wills, trusts, and advanced strategies to minimize tax liabilities and ensure smooth asset transfer. We coordinate beneficiary designations, power-of-attorney documents, and charitable giving plans. This service helps preserve family wealth while implementing techniques like CRTs and ILITs for high-net-worth clients.
Investment Management
We provide active portfolio management with tax-aware strategies including asset allocation, rebalancing, and loss harvesting. Our approach combines ETFs, municipal bonds, and diversified holdings to match client risk profiles. Regular performance reviews ensure alignment with evolving financial objectives and market conditions.
Business Succession
This service develops transition strategies for business owners through buy-sell agreements, key person insurance, and ownership transfer plans. We coordinate with legal and tax professionals to ensure seamless transitions while protecting both business value and personal wealth during ownership changes.
People
John P. Overland
Partner Emeritus
Founder with over 60 years of experience in financial planning for individuals and businesses. Pioneered specialized strategies for business owners before joining High Bluff Private Wealth.
Michael D. Shanahan
Managing Partner
Oversees a team of specialists addressing complex needs of business owners and executives. Brings decades of leadership experience in wealth management and client-focused financial solutions.
David W. McQuade
Wealth Advisor
25+ years in financial services, specializing in corporate and legal community planning. Focuses on retirement plans, estate strategies, and business succession for high-net-worth clients.
Claire E. Shinholser
Wealth Advisor
Helps clients achieve long-term financial goals through personalized planning. Specializes in tax-efficient strategies and investment management for business owners and families.
Gay M. Reeves
Wealth Advisor
Third-generation advisor with 35+ years of experience. Focuses on comprehensive wealth management, including retirement income planning and intergenerational wealth transfer strategies.
Questions
What services do you offer for business owners?
We provide financial planning, retirement strategies, business succession planning, tax optimization, and investment management tailored to business owners' unique needs.
How do you help executives with stock options?
We develop strategies for managing concentrated stock positions, RSUs, and deferred compensation while minimizing tax liabilities and aligning with overall financial goals.
What retirement planning options exist for self-employed individuals?
We implement specialized plans like SEP IRAs, Solo 401(k)s, and defined benefit plans optimized for business owners' cash flow and tax situations.
Do you work with clients outside San Diego?
Yes, we serve clients in 24 states including CA, TX, NY, and FL through virtual consultations and remote portfolio management capabilities.
How are your investment strategies tax-efficient?
We use tax-loss harvesting, strategic asset location, municipal bonds, and ETFs to minimize taxable events while maintaining portfolio growth potential.
What estate planning tools do you recommend?
We utilize wills, trusts, power-of-attorney documents, and advanced strategies like charitable remainder trusts to minimize estate taxes and ensure smooth asset transfer.
Reviews (1)
Brian Cane
Jan 11, 2015 Report
Michael Shanahan and his firm have been instrumental in helping my wife and I plan for retirement, make smart tax planning decisions and most importantly plan for our children's education. His approach is straight forward and honest and my wife and I truly get the sense that Michael cares about our family. One of my favorite aspects of being an Overland and Shanahan client is the regular communication regarding our financial goals. We receive an annual update every year, not to mention several phone calls and emails throughout the year helping us to stay on track with the plan that Michael's firm