How Small Business Owners Can Secure Retirement with Whole Life Insurance, Executive Bonus Plans, FIAs, and Roth IRAs
- Barry Group

- 5 days ago
- 6 min read

How Small Business Owners Can Build a Strong Retirement Plan with Barry Group & Associates
Retirement planning is often a complex challenge for small business owners. Unlike employees of large corporations with access to comprehensive 401(k) plans and corporate pensions, small business owners frequently navigate financial uncertainty and must design retirement strategies that account for fluctuating income, business obligations, and personal financial goals. According to a 2024 Fidelity study, nearly 60% of small business owners report they are not on track to accumulate sufficient retirement savings, and many are concerned about their ability to retire comfortably.
Barry Group & Associates specializes in helping business owners address these challenges through customized financial strategies. By combining whole life insurance, executive bonus plans, fixed index annuities (FIAs), and Roth IRAs, the firm provides small business owners with a multi-faceted approach to retirement planning that balances growth potential, risk management, and tax efficiency.
Whole Life Insurance: Cash Value and Lifelong Protection
Whole life insurance is more than a safety net for families—it is a powerful financial tool for retirement planning. These policies provide a guaranteed death benefit while accumulating cash value over time. This cash value grows tax-deferred and can be accessed during the policyholder’s lifetime through loans or withdrawals. For business owners, this means the ability to tap into funds for retirement, unexpected expenses, or business opportunities without the same restrictions that govern traditional retirement accounts.
Best use by life stage:
Young professionals (20s–30s): Build cash value early while premiums are lower, creating a foundation for long-term growth.
Mid-career (40s–50s): Access accumulated cash value to fund major life events, such as children’s education or business expansion.
Pre-retirement (50s–60s+): Utilize cash value as a supplemental income source or tax-efficient liquidity during retirement.
The combination of growth, protection, and guaranteed cash value makes whole life insurance a cornerstone of a diversified retirement strategy.
Executive Bonus Plans: Funding Retirement for Yourself and Key Employees
Executive bonus plans are employer-funded arrangements that provide additional compensation to employees, typically in the form of life insurance premiums or other benefits. While traditionally used to attract and retain top talent, business owners can also structure these plans to benefit themselves.
By establishing an executive bonus plan for themselves, business owners can fund a personal whole life insurance policy using pre-tax corporate dollars. This strategy allows owners to:
Accelerate cash value growth
Reduce personal out-of-pocket contributions
Create tax-efficient retirement liquidity
Best use by life stage:
Mid-career (30s–50s): Business owners can maximize contributions while their business income is at a growth stage.
Late career (50s–60s+): Leverage accumulated benefits to supplement retirement income or provide a tax-efficient legacy to heirs.
Using an executive bonus plan for themselves ensures that business owners are not only securing key employee benefits but also strategically building their personal financial security.
Fixed Index Annuities (FIAs): Guaranteed Lifetime Income
Fixed index annuities (FIAs) offer small business owners the opportunity to grow retirement savings while minimizing exposure to market volatility. FIAs are linked to a stock market index but include protections against market downturns, ensuring that the principal investment is secure. Many business owners use FIAs to roll over existing 401(k) or 403(b) funds, creating a personal pension that provides reliable income throughout retirement.
A key feature of FIAs is annuitization at retirement age. This means that at a chosen retirement age, the accumulated value of the FIA can be converted into a series of guaranteed lifetime payments, providing predictable, steady income that acts as a personal pension.
Best use by life stage:
Mid-career (40s–50s): Allocate a portion of retirement savings to a low-risk vehicle to balance higher-risk investments.
Pre-retirement (50s–60s+): Convert 401(k) or 403(b) funds into an FIA and plan for annuitization to ensure predictable retirement income.
FIAs are particularly beneficial for business owners seeking stability and predictability in retirement planning. Unlike traditional market-based accounts, FIAs combine growth potential with principal protection, reducing financial uncertainty.
Roth IRAs: Tax-Free Growth and Flexibility
Roth IRAs allow contributions with after-tax dollars, offering tax-free growth and tax-free withdrawals in retirement, provided certain conditions are met. For small business owners, Roth IRAs are a valuable supplement to other retirement savings vehicles, especially for those who expect to be in a higher tax bracket during retirement.
A key consideration is the age at which tax-free withdrawals are allowed. Generally, Roth IRA owners must wait until age 59½ and have held the account for at least five years to access funds tax-free. This makes Roth IRAs particularly strategic for mid-to-late career planning, ensuring long-term, tax-free retirement income.
Best use by life stage:
Early career (20s–30s): Contributions grow tax-free for decades, maximizing long-term growth potential.
Mid-career (30s–50s): Use Roth contributions to diversify tax exposure and create flexibility in retirement income planning.
Late career (50s–60s+): Access Roth IRA funds after age 59½ to supplement other retirement income sources, manage tax brackets, and optimize estate planning.
Roth IRAs provide business owners with flexibility, control over tax liability, and an additional source of retirement income that complements whole life insurance and FIAs.
Integrating Strategies for Maximum Impact
Barry Group & Associates works closely with business owners to create integrated retirement plans that leverage the strengths of each financial vehicle. By combining whole life insurance, executive bonus plans, FIAs, and Roth IRAs, business owners can:
Balance risk and growth: Cash value from life insurance provides a stable foundation, while FIAs and Roth IRAs allow for growth and tax efficiency.
Secure personal retirement income: Executive bonus plans can be structured for the business owner, funding personal policies and retirement goals.
Plan for predictable income: FIAs can be annuitized at retirement age, providing a steady personal pension. Roth IRAs become accessible after age 59½ for tax-free withdrawals.
Enhance employee retention: Plans for key staff create long-term loyalty, which is critical for business continuity.
Provide liquidity and flexibility: Access to cash value or Roth funds ensures financial flexibility for both personal and business needs.
Retirement Life Stage Roadmap for Small Business Owners
Life Stage | Whole Life Insurance | Executive Bonus Plan | Fixed Index Annuity (FIA) | Roth IRA |
Early Career (20s–30s) | Start building cash value early while premiums are low. Creates a long-term foundation. | Typically minimal or optional. Focus on business growth. | Not typically used yet. Early accumulation of other retirement accounts is preferred. | Contribute annually to take advantage of decades of tax-free growth. |
Mid-Career (30s–50s) | Access cash value for business expansion, children’s education, or emergency liquidity. | Fund for yourself to accelerate cash value and reduce out-of-pocket contributions. Can also incentivize key employees. | Allocate a portion of retirement savings to a low-risk FIA for future annuitization. | Continue contributions to diversify tax exposure. Funds remain growing tax-free until eligible for withdrawal. |
Pre-Retirement (50s–60s+) | Use cash value as a supplemental income source or tax-efficient liquidity. | Maximize contributions for personal retirement and legacy planning. | Plan for annuitization at retirement age to ensure predictable income. Protect principal from market downturns. | Withdrawals can begin at age 59½ after 5-year holding period. Tax-free withdrawals supplement other income sources. |
Retirement (60s+) | Access cash value to cover unexpected expenses or supplement retirement income. | Benefits continue for personal retirement if structured properly. | Begin annuitization for guaranteed lifetime income. Serves as a personal pension. | Access funds tax-free if age 59½+ and account held for 5+ years. Adds flexibility to manage income and taxes in retirement. |
How to Use This Roadmap
Early Career: Focus on growth and establishing foundational assets like Roth IRA and whole life insurance.
Mid-Career: Start combining strategies; executive bonus plans and FIAs become more relevant.
Pre-Retirement: Protect assets, plan annuitization, and access cash value strategically.
Retirement: Use FIAs for guaranteed income, Roth IRAs for tax-free withdrawals, and whole life insurance for liquidity or supplemental income.
Small business owners face unique challenges when planning for retirement, but these challenges can be successfully addressed with a strategic approach. Barry Group & Associates provides tailored solutions that integrate whole life insurance, executive bonus plans, FIAs, and Roth IRAs, giving business owners the flexibility, security, and growth potential necessary to achieve their retirement objectives.
By working with experienced advisors, business owners can secure their personal financial future, maximize tax efficiency, and enhance their ability to attract and retain key talent, ensuring the ongoing success of their business.
Call to Action: To explore how Barry Group & Associates can help you design a comprehensive, tax-efficient retirement plan, visit www.barrygroup.net and schedule a consultation today.
References:
Fidelity Investments, “Small Business Owners and Retirement: A 2024 Study,” newsroom.fidelity.com
LivePlan, “The State of Small Business Retirement Savings,” liveplan.com
401k Specialist Magazine, “Many Small Business Owners Not Saving for Retirement,” 401kspecialistmag.com




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