roadmap to RETIREMENT

In this episode of Roadmap to Retirement, I’m joined by credit card rewards consultant Colin Strout to talk about when credit card points beat cash back, how travel “arbitrage” can turn points into outsized value, and why it adds complexity. We cover transfer partners, hybrid cash back-to-points strategies, premium card perks like lounges, and when it’s simply better to stick with a flat 2% cash back card. Colin also explains why responsible use matters and who benefits most—high-spending busine

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