Waterstone Financial

What Waterstone Financial does

Waterstone Financial Advisory is an SEC-registered investment advisory firm headquartered in Fort Myers, Florida, founded in 2011 by James Gallagher, a former General Motors Director of Engineering who transitioned into financial planning. The firm provides boutique retirement-focused financial planning services to individuals, families, and business owners nationwide, with an explicit emphasis on pre-retirees, retirees, and clients navigating major life transitions such as business sales or inheritance events.

Its core offerings are structured around a proprietary "engineered retirement" methodology that combines the firm's five-step Journey process (Blueprint Session, Retirement Buildout, Life Stress Test) with SIPS (Structured Income Planning Software), a proprietary visual, scenario-based planning tool developed by the founder that uses a time-segmented Bucket Strategy across 0-5, 5-10, and 10+ year horizons instead of traditional Monte Carlo simulation. Supporting capabilities include tax planning and in-house tax preparation, estate and asset protection (delivered in conjunction with affiliated attorney Neil R. Covert), and wealth management implemented through the AssetMark platform with Fidelity as custodian.

Waterstone operates on a fee-based fiduciary model with no commissions, generating revenue primarily from recurring advisory fees plus ancillary tax preparation services. Go-to-market is sales-led and content-driven (Fox 4 News appearances, educational video library, blog, webinars, and referrals), with virtual delivery enabling nationwide reach from a single Fort Myers office. The firm doubled its team from three to six after combining with GFA Wealth Design, transitioned to direct SEC oversight in 2025, and in 2025 licensed SIPS to PlanScout for national distribution to thousands of advisors, marking its evolution from a pure advisory practice toward a hybrid advisory-plus-platform business model.

Name

Waterstone Financial

Legal name

Waterstone Financial Advisory

Website

https://waterstonefs.com

Company type

Private

Founded year

2011

Operating status

Operating

Headcount range

1–10 employees

Short description

Waterstone Financial Advisory is a Fort Myers-based, SEC-registered investment advisory firm that delivers retirement income planning, wealth management, tax, and estate services to pre-retirees, retirees, and business owners nationwide via its proprietary SIPS planning software and fee-only fiduciary model.

Ownership category

akta.pro rank

Product category

Financial Advisory Services

NAICS

Portfolio Management and Investment Advice (523940)

SIC

Investment Advice (6282)

akta.pro primary industry

Comprehensive Financial Planning (FSAEAAAA)

akta.pro secondary industries

Financial Coaching & Budgeting Advisory (FSAEAAAH), Advisory Portfolio Management (Non-Discretionary) (FSAAABAD)

Keywords

• Retirement income planning
• Wealth management services
• Tax planning services
• Estate planning services
• Financial advisory services

Headquarters

HQ city

Fort Myers

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Technology or R&D, Operations, Marketing or Sales, Others

Revenue model

1. Financial Advisory Fees: Fee-based fiduciary advisory services. The firm works only on a fee-basis as a registered investment advisor with a legal obligation to act in clients' best interests. Specific fee structures are not publicly disclosed and are quote-based.
2. Tax Preparation Services: In-house tax preparation services offered through Sue Wood, providing tax preparation and planning services to existing advisory clients.

Pricing tiers

Go-to-market motion1 record

Distribution channels2 records

Marketing channels7 records

Core offering

Waterstone Financial Advisory is a fee-only, SEC-registered investment advisory firm that provides comprehensive retirement-focused financial planning to individual clients and families. Its core offerings include retirement income planning, wealth management implemented through a proprietary Bucket Strategy, tax planning and preparation, and estate and asset protection. Services are delivered via a structured 'Journey' planning process and supported by the firm's proprietary SIPS (Structured Income Planning Software) for scenario-based retirement income modeling.

Product overview

Waterstone Financial Advisory is an SEC-registered investment adviser offering comprehensive retirement-focused financial planning services centered on its proprietary SIPS (Structured Income Planning Software) platform. SIPS is a visual, scenario-based retirement planning tool using a time-segmented Bucket Strategy approach, distributed nationally through PlanScout. The core service offering encompasses Wealth Management (implementing the Bucket Strategy via AssetMark platform with Fidelity as custodian), Retirement Income Planning, Tax Planning and Preparation, and Estate and Asset Protection. The firm serves clients nationwide from their Fort Myers, Florida office using a fee-only fiduciary model.

Differentiator

Problem solved

Functional benefit

Brands

• SIPS: Structured Income Planning Software - proprietary retirement income planning software developed by founder James Gallagher, now used by advisors nationwide through PlanScout partnership.

Products and services

• Retirement Income Planning Strategic retirement income planning using SIPS software and the time-segmented Bucket Strategy to create sustainable, tax-efficient income streams resilient across market cycles. Includes Social Security optimization, annuity evaluation, and RMD management for individuals and households approaching or in retirement.
• Wealth Management Comprehensive wealth management implementing the Bucket Strategy across three time horizons: Bucket 1 (Short-Term 0-5 years) for cash reserves and capital preservation, Bucket 2 (Mid-Term 5-10 years) for moderate growth, and Bucket 3 (Long-Term 10+ years) for growth-oriented assets. Investment execution is performed on the AssetMark platform with Fidelity serving as custodian.
• Tax Planning and Preparation Tax strategy services integrated with retirement planning, including Roth conversion timing, withdrawal sequencing across account types, capital gains management, and tax-loss harvesting. In-house tax preparation is available through Sue Wood for advisory clients.
• Estate and Asset Protection Estate planning, risk management, and legacy design services including wills, trusts, beneficiary designation strategies, long-term care planning, and asset protection structures such as LLCs and family limited partnerships. Delivered in coordination with affiliated estate planning counsel.
• SIPS (Structured Income Planning Software) Proprietary retirement income planning software developed by founder James Gallagher that uses a time-segmented Bucket Strategy approach rather than traditional Monte Carlo simulations. SIPS enables visualization of financial plans through stress-tested, real-world scenarios and shows how plans perform under conditions such as inflation surges, tax changes, and unexpected expenses. Distributed to advisors nationwide through the PlanScout partnership.
• The Journey Planning Process Waterstone's proprietary financial planning process consisting of three phases: Blueprint Session (goal clarification and financial discovery), Retirement Buildout (custom strategy design using SIPS), and Life Stress Test (ongoing monitoring and scenario testing). Documents client situations, goals, and planning across estate, tax, income, and investment planning areas.

Quantifiable outcome

• SIPS software now used by thousands of advisors nationwide through PlanScout partnership

Named customers1 record

Segments4 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration6 records

Feature3 records

Partnerships

Four partnerships are on record, tiered core and minor.

• AssetMarkcoreTechnology or IntegrationAssetMark provides the investment platform and technology used by Waterstone Financial. The platform offers access to professional managers, model portfolios, and performance reporting. In 2024, AssetMark was acquired by GTCR LLC, removing previous Chinese ownership. Waterstone confirms client accounts remain custodied at Fidelity with AssetMark providing back-office support.
• FidelitycoreTechnology or IntegrationFidelity serves as the custodian for client investments and accounts. Waterstone Financial uses Fidelity's infrastructure for account custody and trading while providing the advisory planning services.
• PlanScoutcoreStrategic or Co-development PartnerPlanScout is a strategic partner that licensed and scaled SIPS software nationally. Founded by Raygar and partners, PlanScout provides SIPS to thousands of advisors nationwide while maintaining the original planning philosophy. Founder James Gallagher serves in a leadership role for PlanScout, advocating for the software at national conferences.
• Neil R. Covert, P.A.minorImplementation/ SI/ Consulting PartnerNeil R. Covert is an estate planning attorney who collaborates with Waterstone Financial as an affiliated professional. He has practiced law for 43 years focusing on estate planning, elder law, asset protection, and probate since 1988. He serves as a guest lecturer and author on estate and business planning topics.

Scale indicators2 records

Recent moves9 records

Expansion highlights6 records

Direct peers

• Buckingham Wealth Partners: Fee-only RIA platform with research-driven retirement and tax planning, serving HNW households. Comparable fiduciary positioning and integrated planning philosophy; broader geographic footprint.
• Carson Group: RIA consolidator and wealth-management platform serving advisors and their retirement-age clients with proprietary technology, coaching, and back-office infrastructure. Comparable advisor-services model and target demographic.
• Creative Planning: Large, nationally recognized fee-only RIA offering comprehensive retirement, tax, and estate planning with proprietary technology. Directly comparable business model and target client base (HNW households, pre-retirees), but at significantly greater scale.
• Mariner Wealth Advisors: Large national RIA offering comprehensive financial planning, tax, estate, and retirement services to HNW individuals. Directly comparable service breadth and fiduciary positioning; operates at much greater scale with active M&A.
• Wealth Enhancement Group: RIA consolidator offering retirement income planning, wealth management, and tax services to HNW individuals. Comparable target client and integrated service model; growth driven by advisor team acquisitions.
• Edelman Financial Engines: National fee-only RIA with deep retirement-income-planning focus serving mass-affluent and HNW households. Comparable fiduciary model, integrated planning, and proprietary planning tools; meaningfully larger AUM and headcount.
• Savant Wealth Management: Mid-market fee-only RIA with integrated retirement, tax, and estate planning serving HNW families and business owners. Closely comparable size tier and service mix; has grown significantly through advisor M&A.

Others

• Nitrogen (formerly Riskalyze): Risk-tolerance and financial-planning technology used by Waterstone's planning process. Adjacent ecosystem vendor providing complementary capabilities rather than competing directly with Waterstone's advisory services.
• eMoney Advisor (Fidelity): Financial planning software platform used by Waterstone and thousands of other advisory firms. Adjacent/ecosystem participant rather than direct competitor; relevant because it sits alongside SIPS in Waterstone's tech stack.

Broad incumbents

• Cetera Financial Group: Large independent broker-dealer and RIA support platform serving retirement-focused advisors nationwide. Comparable end-client demographic and retirement-planning emphasis; broader product set including brokerage.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat4 records

Key risks5 records

Key highlights6 records

Customer concentration

• Facebookfacebook.com/GFA.Waterstone
• LinkedInlinkedin.com/company/waterstone-financial

Compliance7 records

Revenue estimate

Valuation estimate

Number of profiles

Profiles9 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Waterstone Financial