Who We ARE
Connecticut Retirement Readiness is dedicated to providing a wide range of services to public and private employees across our state and beyond. With the support of Bluedoor Private Wealth, we share a responsibility for guiding you through your financial challenges, on your way to realize your retirement dreams.
• Retirement Plan Management
• Financial Planning
• Investment Strategy
• Estate Planning
• Financial Literacy
•Wealth Management
•Advisory Services
Retirement Planning
Hands on Coordination to ensure:
• Complete document experience
• Trustee-to-trustee transfers
• Tax-efficient execution
• Custodian navigation tutorial
Plans:
• Governmental 457 Plans
• 401(a) Plans
•403(b) Plans
• 401(k) Plans
• IRA
• Roth IRA
We streamline the process to make the transition seamless, efficient, and understandable
Can I retire?
Paycheck Analysis
One of the most important questions anyone approaching retirement will ask is simple: “Can I retire?” The answer begins with clarity. A thoughtful retirement readiness analysis starts with a full inventory of your financial life—your assets, liabilities, income sources, and living expenses. Assets may include retirement accounts such as 401(k)s, IRAs, brokerage accounts, pensions, and personal savings. Liabilities may include mortgages, loans, or other obligations that will continue into retirement. Equally important is understanding your expected income streams and the level of expenses required to support the lifestyle you envision.
As individuals transition from their working years into retirement, several key financial changes occur. Many retirees consolidate assets from 401(k) plans, IRAs, and defined-benefit pension plans into a coordinated retirement income strategy. At the same time, healthcare coverage typically transitions from employer-sponsored insurance to Medicare, often paired with a Medigap or a Medicare Advantage plan. These changes require careful planning so that income, taxes, and healthcare costs remain sustainable over a retirement that could last decades.
Our retirement readiness process includes a dynamic financial analysis that evaluates your retirement picture under multiple scenarios. We model the impact of inflation, healthcare expenses, taxes, market performance, and longevity to help determine whether your current resources can support your retirement goals. If the analysis suggests that you are not yet ready to retire, we will help identify the steps that could move you closer to that goal—whether through additional savings, adjusting retirement timing, refining investment strategy, or managing expenses.
Ultimately, the question is not simply “Can I retire today?” but also “If not today, when?” and “What actions between now and then will strengthen my financial independence?” With thoughtful planning and disciplined strategy, retirement readiness becomes less about guesswork and more about informed decision-making.
Our Retirement Ready Analysis
1. Longevity planning
People are living longer; planning for a 25–35 year retirement is increasingly common. Modeling life expectancy scenarios can show whether assets last.
2. Social Security timing analysis
Include strategy around Social Security claiming ages (62–70), spousal benefits, and survivor benefits.
3. Withdrawal strategy
Explain sustainable withdrawal rates and sequencing of withdrawals from taxable, tax-deferred, and tax-free accounts.
4. Tax strategy in retirement
Roth conversions, required minimum distributions, and tax-efficient withdrawals can materially affect retirement success.
5. Stress testing the plan
Running “what-if” scenarios:
• Market downturn early in retirement
• Higher healthcare costs
• Long-term care needs
• Inflation spikes
6. Lifestyle and legacy goals
Travel, gifting, philanthropy, or leaving assets to heirs can be incorporated into the analysis.
7. Contingency planning
If the answer is “not yet,” outline steps such as:
• Work a few additional years
• Increase savings rate
• Reduce debt
• Adjust retirement lifestyle expectations.
Strategies
Financial Planning
CRR Supports comprehensive financial planning that is integrated with your portfolio strategy. Planning with our team includes an integrated approach including:
Retirement Income Projections
We model your complete income picture across a range of sources to provide a full picture of what your retirement cash flow will look like year by year. Can I retire?
Social Security Timing Analysis
We analyze the optimal age to claim social security based on your health, pension income, and tax situation to maximize your lifetime payout.
Pension Coordination
We help you navigate Connecticut’s pension system to integrate your defined benefit with other income sources for a semless retirement strategy.
Tax-efficient Withdrawal Strategies
We sequence withdrawals from your taxable, tax deferred, and tax exempt accounts to minimize your lifetime tax burden and preserve more of what you’ve saved.
Estate Planning Coordination
Along with offering included estate plan through our partner, we can work alongside your estate attorney to align your beneficiary designations, account titling, and legacy goals with your overall financial plan.
Risk Management Review
We assess your exposure to longevity, market, and healthcare risks to ensure your portfolio and protections are calibrated for a financially secure retirement.
Investment Management
Disciplined asset allocation is central to long-term success. We utilize both in house and external portfolio managers to carefully craft personalized investment strategies.
Our investment motto is to “invest with purpose”, striking a balance between achieving your goals, while managing risk. To do so, we construct diversified portfolios across three primary asset classes:
Equities
• U.S. Stocks
•International Stocks
• ETF Strategies
Fixed Income
• U.S. Bonds
• International Bonds
• Money Market Solutions
• Treasuries
Alternative Assets
• Hedge Fund Strategies
• Private Equity
• Cryptocurrency ETFs
• Specialty Credit
Custodial Partners
• Founded in 1971
• ~$8+ Trillion in discretionary assets
• Industry-leading custodial and advisor platform
• Founded in 1946
• ~$4+ Trillion in discretionary assets
• Privately held with a strong financial history
Together, these firms provide quality trading platforms, institutional level reporting, daily account valuation, secure online access, mobile applications, and integrated performance reporting.
Our Commitment to You
We are dedicated to providing our clients exceptional support up to and through their retirement journey. Our team is committed to:
• Individualized portfolio design
• Diverse asset allocation
• Competitive pricing
• Institutional investment access
• Secure reporting
• Responsiveness
• Availability Monday through Saturday
8:00 AM – 8:00 pm
Our Team
John R. Shepherd Jr.
Portfolio Manager
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John R. Shepherd Jr.
Vice President
John R. Shepherd Jr. has joined Connecticut Retirement Readiness, a division of Bluedoor Private Wealth, as Vice President. In this role, he works with the firm’s team on all aspects of private wealth management, helping individuals and families pursue long-term financial security and retirement readiness.
John’s passion, work ethic, and highly individualized approach to client relationships have earned him recognition as an innovator across the institutional investment industry, including the broker-dealer marketplace, registered investment advisor community, and family office environments.
Prior to joining Connecticut Retirement Readiness, John served as Vice President at Fairbanks Capital Management a California-based registered investment advisor and real estate boutique. Earlier in his career, he was a Director at a leading RIA technology firm and a Portfolio Manager responsible for debt, equity, and asset allocation strategies.
John’s previous leadership roles also include Managing Director at Lateef Investment Management as well as Vice President positions at Fidelity Investments and The Hartford.
He is a graduate of St. Anselm College and an honors graduate school masters program at City College of New York Business School. John has also been finance faculty at the college level.
Outside of his professional work, John is an author, tennis player, golfer, and avid fitness enthusiast. He has a strong interest in the financial and health decisions seniors make as they prepare for retirement, and he closely follows local, national, and international political developments.
Thomas E. Shepherd
President, Managing Director
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Thomas E. Shepherd
Vice President
Thomas E. Shepherd has joined Connecticut Retirement Readiness, a division of Bluedoor Private Wealth, as Vice President. In this role, he works with the firm’s team on all aspects of private wealth management, helping individuals and families pursue long-term financial security and retirement readiness.
Tom’s passion for helping others achieve financial success is the driving force behind his work. He is committed to building lifelong relationships with clients and believes strongly that financial advice and financial education go hand in hand. Tom is particularly passionate about teaching financial literacy and helping clients develop a clearer understanding of their financial lives so they can confidently work toward their goals. As he often tells clients, he enjoys teaching them “how to play—and win—the money game.”
Prior to joining Connecticut Retirement Readiness, Tom served as a Registered Investment Adviser with Baystate Financial, a division of MassMutual, and as a Registered Representative and Retirement Counselor with Empower, Prudential, Voya, and ING. In those roles, he worked extensively with participants in the State of Connecticut Employee Retirement Plans. He primarily served employees at the University of Connecticut, along with professionals across many state agencies including the Department of Education, Department of Transportation, Judicial Branch, Legislative Management, and numerous other state departments. As a former State of Connecticut employee himself, Tom has a deep understanding of the state’s pension systems and supplemental retirement plans.
Tom graduated from Villanova University with a Bachelor of Arts in Sociology, with a concentration in Criminal Justice and a minor in Philosophy. Earlier in his career, he worked as a paralegal while considering law school. When the legal profession proved not to be the right path, he transitioned into the medical field, working in clinical research at the University of Connecticut Health Center. While preparing for medical school, a physician colleague encouraged him to pursue financial advising, recognizing his natural aptitude for financial matters and his ability to help others navigate complex financial decisions. Taking that advice ultimately led Tom to the profession where he discovered his true calling.
Outside of his professional work, Tom maintains an active and diverse set of interests. A former fitness trainer in Philadelphia, he continues to prioritize health and fitness. As the former owner of Shepherd Landscaping, he also enjoys landscaping and helping neighbors and friends beautify their properties. Tom has played ice hockey for most of his life and still enjoys getting on the ice when he can. He also enjoys music, including singing and learning to play guitar, bass guitar, and drums. An avid reader of the literary classics, Tom is passionate about lifelong learning and exploring different cultures through travel, particularly in Europe. Above all, he believes strongly in sharing knowledge and helping others grow.
Michael Kozak, J.D., CFP
CEO
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Michael Kozak, J.D., CFP
CEO
Michael is the Founder and CEO of BlueDoor Private Wealth. He has over twenty years of experience providing investment, tax and estate planning advice to individuals, family groups and charities.
Prior to founding BlueDoor, Michael was a founding partner of Little House Capital, LLC. He also served as a principal and Chief Compliance Officer of East Coast Asset Management. Prior to his time at East Coast, Michael was a Principal and the Director of Wealth Management with Cabot Money Management, Inc. in Salem, MA. While at Cabot, Michael was responsible for overseeing the wealth management and tax preparation services for the firm. He also served as the firm’s Chief Compliance Officer. Prior to Cabot, Michael worked for The Colony Group, LLC in Boston, MA where he provided financial planning services to high net worth families and corporate executives as well as estate planning services through the firm’s affiliated law firm.
Michael received his B.A. from the University of Massachusetts at Amherst in Anthropology and earned his Juris Doctor from Boston University. Michael is admitted to practice law in Massachusetts and before the U.S. Tax Court. He also holds the Certified Financial PlannerTM (CFP®) designation.
In addition to his professional life, Michael is an avid golfer and soccer fan.
Grady Kozak
Associate Portfolio Manager
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Grady Kozak
Associate Portfolio Manager
Grady is an Associate Portfolio Manager at BlueDoor Private Wealth, where he supports the firm in both an investment research and client adviser capacity. Grady is particularly focused on using his background to drive deep fundamental analysis to support BlueDoor’s long-term investment focus. In his capacity working with clients, he strives to offer a personalized approach to the client experience by bridging the gap between the portfolios and real world needs of each individual client.
Prior to joining BlueDoor, Grady graduated Magna cum Laude from Fordham University with a B.S. in Business Administration concentrating in Finance. While enrolled at Fordham, Grady was a member of the Division 1 men’s soccer team and competed in the NCAA National Tournament. He also founded Collegiate Skillz which provides sports based after-school programs delivered by college athletes to schools throughout the United States.
He is currently enrolled in the CFA program as a Level 2 candidate, having passed his Level 1 exam.
Apart from his work with BlueDoor, Grady enjoys travel, golf and continues to play soccer and maintain his lifelong support of Manchester United.
Ryan O'Meara
Associate Financial Counselor
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Ryan O’Meara
Associate Financial Counselor
Ryan O’Meara is an Associate Financial Counselor at BlueDoor Private Wealth, where she supports the firm’s advisors in delivering investment support and administrative services to clients. She plays a key role in the client experience, helping to ensure that each client receives prompt, thoughtful, and highly personalized attention throughout their financial journey. Ryan previously worked in the financial advisory industry in Portsmouth, NH and brings a fantastic combination of knowledge, efficiency and enthusiasm to our team.
Ryan graduated from the University of New Hampshire in 2021 with a B.A. in English. She is committed to continuing her professional development in the areas of investment planning, estate coordination, and client advisory services. She is particularly interested in the role that clear communication and thoughtful planning play in helping clients feel confident in their financial decisions.
Outside of work, she practices yoga and enjoys spending time with family and friends.
Take control of your retirement and the path that leads you there
Call us today: (860) 200-1332