The Rollover Company

What The Rollover Company does

The Rollover Company is an independent financial advisory firm founded in 2001 by Charles Winfrey and headquartered in Brentwood, Tennessee, with additional offices in Nashville and Alpharetta, Georgia. The firm serves pre-retirees and retirees nationwide, providing retirement income strategy, IRA and 401(k) rollover guidance, Social Security and pension optimization, tax minimization, estate and legacy planning, long-term care planning, and asset protection — typically using insurance and annuity vehicles to create guaranteed income components alongside traditional advisory allocations. Its go-to-market is education-led and event-driven, built around complimentary dinner seminars, webinars, blog content, and a weekly radio show on WLAC 1510 AM, with prospects converting via a no-obligation Customer Care Needs Analysis consultation.

The business operates on a two-stream revenue model: recurring investment advisory fees generated through its partnership with Brookstone Capital Management, LLC (BCM), a separate Registered Investment Advisor, plus commissions and product-based revenue from insurance and annuity placements. The firm holds no proprietary technology stack beyond a standard client portal; all investment advisory execution is administered externally via BCM, and the firm's competitive differentiation rests on the founder's 28+ years of industry experience, multi-state insurance licensing, and the co-President's CPA background with Big Four experience at Arthur Andersen and Ernst & Young. The product catalog is anchored on Retirement Income Strategies as the core offering, complemented by Wealth Accumulation, Asset Protection, Life Insurance, Tax Minimization, Long-Term Care, and IRA Legacy Planning, with estate planning, trusts, probate, and charitable giving provided via referral partnerships.

Name

The Rollover Company

Legal name

The Rollover Company, Inc.

Website

https://rollovercompany.com

Company type

Private

Operating status

Operating

Headcount range

11–50 employees

Short description

The Rollover Company is an independent financial advisory firm, founded in 2001 and led by Charles and Nancy Winfrey, that serves pre-retirees and retirees nationwide with retirement income strategies, IRA/401(k) rollovers, annuity-based income planning, and tax and estate coordination, delivered via BCM as RIA partner.

Ownership category

akta.pro rank

Product category

Retirement Financial Advisory

NAICS

Portfolio Management and Investment Advice (52394), Portfolio Management and Investment Advice (523940)

SIC

Investment Advice (6282), Life Insurance (6311)

akta.pro primary industry

Rollover & Distribution Advisory (IRA/401(k) Rollovers) (FSAEABAG)

akta.pro secondary industries

Retirement & Distribution Planning RIAs (401(k)/IRA/Pension Rollovers) (FSAAACAE), Estate & Legacy Planning Advisory (FSAEAAAG)

Keywords

• Retirement income planning
• 401k rollover services
• Annuity income strategies
• Retirement tax planning
• Financial advisory services

Headquarters

HQ city

Brentwood

HQ country

United States

HQ region

North America

Offices3 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

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

Revenue model

1. Investment Advisory Services: Investment advisory services offered through Brookstone Capital Management, LLC (BCM), a Registered Investment Advisor. The Rollover Company, Inc. and BCM are independent of each other.
2. Insurance and Annuity Products: Financial strategies and asset management services using insurance products such as annuities. Fixed insurance and annuity product guarantees are subject to the claims-paying ability of the issuing company.

Pricing tiers

Go-to-market motion2 records

Distribution channels2 records

Marketing channels5 records

Core offering

The Rollover Company is an independent financial advisory firm that provides retirement income planning services for pre-retirees and retirees across the United States. The firm specializes in 401(k) to IRA rollover guidance, annuity-based income strategies, and integrated retirement planning covering tax minimization, asset protection, wealth accumulation, and estate planning. Investment advisory services are delivered through Brookstone Capital Management, LLC (BCM), a separate Registered Investment Advisor through which the firm operates.

Product overview

The Rollover Company offers a unified retirement income planning platform built around core financial advisory services and insurance products. The primary offering includes Retirement Income Strategies as the central product, supported by complementary products including Annuities, Life Insurance, Wealth Accumulation, Asset Protection, Tax Minimization Strategies, Long-Term Care, and IRA & 401(k) Rollovers. The company also provides referral connections to Estate Planning, Trusts, Probate, Charitable Giving, Tax Planning, and IRA Legacy Planning services, creating a comprehensive ecosystem for retirement income planning. Services are coordinated with Brookstone Capital Management, LLC for investment advisory components.

Differentiator

Problem solved

Functional benefit

Products and services

• Retirement Income Strategies
• IRA & 401(k) Rollovers
• Annuities
• Life Insurance
• Asset Protection
• Wealth Accumulation
• Tax Minimization Strategies
• Long-Term Care Planning
• IRA Legacy Planning
• Trusts Referral Service
• Estate Planning Referral Service
• Charitable Giving Referral Service
• Probate Referral Service

Quantifiable outcome

• 52% chance that at least one spouse in a 65-year-old couple will reach age 94
• +2 more outcomes

Named customers1 record

Segments2 records

Ideal customer profiles1 record

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Scale indicators2 records

Recent moves5 records

Expansion highlights4 records

Broad incumbents

• Edelman Financial Engines: Largest independent RIA in the U.S., offering retirement income planning, IRA rollovers, and wealth management nationally. Comparable to The Rollover Company in target customer (retirees/pre-retirees) and service mix (retirement income, advisory), but vastly larger in scale and AUM.
• Fisher Investments: Large independent investment management firm serving retirement-age investors with personalized portfolio management. Overlaps with The Rollover Company's pre-retiree/retiree segment and personalized advisory approach, but operates at much greater scale with primarily portfolio management rather than rollover specialization.
• Ameriprise Financial: Large financial advisory firm with extensive retirement planning, IRA rollover, and annuity product offerings. Comparable in retirement income planning and insurance product mix, but operates through a much larger advisor network and corporate structure.
• Cetera Financial Group: Network of independent financial advisors offering retirement, wealth, and tax planning services. Comparable independent advisory model serving retirement-age clients; provides back-office RIA platform similar to Brookstone Capital Management relationship used by The Rollover Company.
• Cambridge Investment Research: Independent RIA platform supporting independent financial advisors with retirement planning, wealth management, and practice management tools. Comparable to BCM in serving independent advisors like The Rollover Company.
• Waddell & Reed Financial: Established financial advisory firm offering retirement planning, wealth management, and investment advisory services. Comparable in retirement planning focus and relationship-based advisory model.

Emerging players

• Personal Capital (now part of Empower): Hybrid digital/human financial advisory firm serving mass-affluent and retirement-age clients with retirement planning, portfolio management, and rollover services. Directly competes with The Rollover Company for retirement-focused clients, but through a technology-led delivery model.
• NewRetirement (Boldin): Retirement planning software platform enabling DIY retirement income, tax, and Social Security planning. Adjacent to The Rollover Company's service offering; represents the do-it-yourself segment that competes with traditional advisory practices.
• Guia Wealth: Smaller independent RIA focused on retirement planning and rollover advisory services. Comparable niche focus on retirement income planning with a more boutique delivery model.

Direct peers

• David Lerner Associates: Independent financial advisory firm specializing in retirement income planning, IRA rollovers, and wealth management for individuals approaching or in retirement. Closely comparable to The Rollover Company in customer segment, retirement income focus, and event-driven marketing approach.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 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 The Rollover Company