Winning Retirement Radio

When it comes to managing your money, should you trust family — or is a fresh set of eyes the smarter move? From parents who jokingly say they’ll “move in” if their advisor-son loses the money, to widows who struggle to trust anyone new, the Taylors explore the emotional, practical, and financial challenges of working with someone who shares your last name. They discuss why trust can’t be assumed — it must be earned — and why experience, objectivity, and the ability to have tough conversations matter more than familiarity. Whether you’re considering hiring a family member or wondering if it's time to step outside your comfort zone, this episode will help you think more clearly about trust, transparency, and choosing the right guide for your retirement journey.