Episodes

Today on Roadmap to Retirement, I’m sitting down with Jason Grover for a fourth time to break down what a market bubble is, why AI may feel like one, and what investors can do about it. We talk about euphoria, valuations, and the danger of FOMO—especially for new investors or retirees relying on income. I explain why we stick to a written plan, stay diversified, and avoid trying to time the market. We also cover “know what you own,” how index funds evolve over time, and why time in the market ma...

In this episode of Roadmap to Retirement, I’m joined by Dana DeLuca to break down what long-term care insurance is, why Medicare won’t cover it, and what care can cost—from in-home help to assisted living and nursing homes. We compare three main options—traditional standalone long-term care, life insurance with an accelerated death benefit rider, and hybrid/linked-benefit policies—plus how underwriting and premiums differ. We also discuss the risks of self-insuring, Medicaid limitations, and way...

Welcome back to another solo episode. Today I’m breaking down popular financial planning rules of thumb…some I like and some I don’t. I’ll cover the 50/30/20 budgeting rule, why a 3–6 month emergency fund matters, and how “pay yourself first” can make spending guilt-free. We’ll compare debt payoff strategies (snowball vs. avalanche), discuss the 20/4/10 car-buying rule, and a guideline for limiting student loans. Finally, I’ll explain why I dislike age-based stock/bond rules and why I still like...

In this episode of Roadmap to Retirement, I sit down with Conner Young from Baskets Capital to talk about what business owners should consider when planning to exit. We cover common valuation blind spots, organizing financials, and how taxes can change depending on how you sell. Conner shares why the five-year mark matters for potential QSBS planning, plus how to think about saving and investing outside your business to reduce concentration risk while you grow. Thank you for listening and come ...

Welcome back to another “Roadmap to Retirement” episode. During this episode, I am covering several financial topics. Addressing fears of an AI-driven market bubble by comparing two investors: one stays invested and grows $100 to $200 before a 40% drop to $120, while the other stays in cash at $100, illustrating why long-term investors may still come out ahead and why market predictions are unreliable. I discuss college savings tools, emphasizing opening a 529 plan early to enable gifts from fam...

Welcome back to Roadmap to Retirement. This episode we are joined by friend of the show, Nick Savas for a fast-moving conversation drawn from common client questions. We discussed how to choose inflation assumptions in financial plans—typically using long-term historical averages around 3% and stress-testing higher rates—while noting that each person’s “personal inflation rate” can differ from headline CPI and that healthcare costs often rise faster (around 5–6%). We talked about Social Security...

Welcome back to the Roadmap to Retirement podcast! During this episode, I explain how parents can decide if college is the right path by making the economics real: estimate a child’s starting salary, subtract savings and taxes, then build a post-graduation budget including student loan payments, rent, and car costs. I use nursing as an example and show how big loans can strain cash flow, influencing school choices like scholarships, state school, or two years of community college. I also urge ap...

Welcome back to Roadmap to Retirement, this episode I will be answering recent client questions: What to do if you’re spending more in retirement (first verify if it’s sustainable, then budget, cut expenses, or add part-time income) How to help an elderly mom after a pension ends (consider selling the home or a reverse mortgage) Ways to tackle credit card debt (lower-rate loans, possibly a 401(k) loan and fixing the underlying income/expense or emergency-fund issue) Planning a “retirement” t...

On the Roadmap to Retirement Podcast, I talked with Jason Grover from Grover Financial Services about how geopolitical conflicts like the current Iran situation can spark fear and tempt investors to make drastic moves. Our core message was that “this time isn’t different”: if your goals haven’t changed and you still own great companies, the plan shouldn’t change just because of headlines you can’t control. For clients still accumulating, market drops can mean buying more shares while prices are...

In this Roadmap to Retirement episode, I break down what “Trump accounts” are and when they may make sense for parents and grandparents. The account lets you contribute up to $5,000 per year and works like a non-deductible, after-tax IRA: your contributions come back tax-free, but any growth is taxed as ordinary income when withdrawn. The big draw is the federal $1,000 seed deposit for children born between January 1, 2025 and December 31, 2028, so if you’re eligible, I recommend taking the free...

In this solo Roadmap to Retirement mailbag, I answer five listener and client questions: how to retire early by building a liquid, non-retirement investment pool to bridge the years before penalty-free access to retirement accounts (while still enjoying life); whether to buy a whole life policy for a friend, where I stress starting with your financial plan rather than a product; whether to buy silver, where I caution against chasing what’s been hot and suggest only a small, diversified allocatio...

On this episode of Roadmap to Retirement, I talked with Jon Sheldon, founder of BelleauWood Coaching LLC in Rochester, NY, about the non-financial side of the FIRE movement—especially the purpose gap that can hit when someone retires around 45 and suddenly loses the structure and meaning work provided. Jon explains his coaching framework built on four pillars: Purpose (separating personal purpose from business purpose and spotting misalignment) Vision Motivation Ecosystem (the people, place...

In this episode of Roadmap to Retirement, I sat down again with Jason Grover to talk about how financial planning shouldn’t only revolve around the vague idea of “retirement someday,” especially for younger people who need more motivating, near-term goals. We discussed common “pipe dream” goals like buying a cottage or lake house and even retiring early, and why those goals are often achievable if you’re willing to make the sacrifices and turn them into a date-specific, dollar-specific plan. Ja...

Welcome back to the Roadmap to Retirement podcast. In this solo episode, I discuss two key topics. First, the challenge some retirees face of having ‘too much money,’ a situation often resulting from decades of diligent saving and conservative spending habits. I explore strategies for making meaningful use of these funds, such as gifting to adult children or supporting charities, and also suggest indulging in personal bucket list experiences. Second, I address the temptation and pitfalls of deb...

In our latest episode of Roadmap to Retirement, we dive into the interplay between accountants and financial advisors with Jordan Stealey, EA at Redwood Tax and Accounting. We discuss the importance of collaboration in financial planning and tax preparation, especially around tax season. Topics include the misperceptions surrounding Qualified Charitable Distributions (QCDs), the nuances of handling RMDs, and strategies for business owners to save effectively for retirement. Jordan also shares ...

Welcome to The Roadmap to Retirement, this episode I am flying solo. As a way to kick off the new year, let’s talk about financial planning best practices, tips and smart money moves. Learn about the Mexican fisherman story, and the importance of financial goals aligning with one’s desired lifestyle rather than merely accumulating wealth. I want to caution against relying on market predictions, and stress the importance of a well-thought-out investment philosophy that can withstand market fluct...

Welcome back to the Roadmap Retirement Podcast! Kicking off the new year strong with a new guest – Jesse Cramer, who transitioned from a mechanical engineer to a financial planning and wealth management professional. We dove into Jesse’s journey, including his podcast, ‘Personal Finance for Long-Term Investors,’ and discussed the unique financial planning perspectives that come from his engineering background. We explored the challenges faced by detail-oriented clients, especially engineers, an...

Welcome back to the Roadmap Retirement Podcast, returning for a second time, I am talking with Alex Wesdorf today to talk about the often-avoided topic of disability insurance. This episode explores the critical need for disability insurance, especially for self-employed individuals and W2 employees who might not fully comprehend their existing benefits. We discuss real-life scenarios, such as the impact of injuries and the undervalued risk of cognitive issues. Highlights include the inadequate...

Welcome back to the ‘Roadmap to Retirement’ podcast, where we delve into financial tips, investment strategies, and smart money moves to supercharge your retirement savings. Today, I’m joined by Tom Harris, someone whose career and perspective on retirement resonate with many of our clients. Tom shares his journey from a career in operations excellence and leadership development in Rochester to his current semi-retired status. He emphasizes the importance of understanding one’s motivations and ...

Welcome to another episode of the Roadmap to Retirement Podcast! I’m joined once again by Matthew Jarvis. In this episode, we dive into the complexities of retirement planning, with a particular emphasis on tax strategies. We shed light on recent changes in tax laws, such as the increase in the state and local tax (SALT) cap from $10,000 to $40,000, and new provisions for charitable contributions. We also discuss the importance of proactive tax planning to avoid unexpected tax bills in retiremen...

Insights from Bill Cates on Wealth Wisdom In a recent episode of the Roadmap to Retirement podcast, I had a great conversation with Bill Cates, The Original Referral Coach, about financial decision-making and referrals. We delved into the importance of mindset, nurturing referable relationships, and his new book, “The Hidden Heist.” Bill shared invaluable tips for advisors seeking quality client introductions, emphasizing the significance of value recognition and strategic referrals. It was a ...

In this episode of Roadmap to Retirement, we dive deep into real estate strategies, focusing on first-time home buyers and retirees looking to downsize. Julie Ohmann from Remax shares insights on the initial consultation process, emphasizing the importance of understanding terms and the home buying timeline. For first-time buyers, planning for a 5-10 year home is advised to avoid equity issues and contingent sales. Julie also highlights the benefits of flexible house options, such as duplexes, w...

In this episode of Roadmap to Retirement, I am joined by John Howe-Wemett, CFP®, MSFP for a fourth time to discuss various aspects of financial planning for retirement. We address common misconceptions about Social Security, “is it a Ponzi Scheme?” and the importance of understanding its broader benefits. We cover the clickbait concept of retiring with one million dollars and highlight how financial needs vary significantly based on individual circumstances. A substantial part of this episode i...

Welcome back to the Roadmap Retirement Podcast! I was recently joined by Liam Hanlon, the Head of Insights at Jump, a leading AI meeting assistant in the financial advice sector. Liam explains how Jump leverages unique and powerful data to aid advisors and make their work more efficient. During our discussion, we delve into the adoption of AI in financial advisory, its impact on time management, and how advisors can use this technology to reclaim significant amounts of time—up to 250 hours per y...