Up Your Average

A legacy letter, a father's voice, and the question every child carries for the rest of their life without asking out loud. Blake Brewer, founder of Legacy Letter, joins Keith Tyner and Doug Shrieve to share how a letter his father wrote before his unexpected death became the framework for helping more than 20,000 families pass down what matters most.This episode walks through the Legacy Letter framework from beginning to end: apology, unconditional love, specific affirmation, belief in your children's future, shared memories, and the advice that only sticks when it follows genuine connection. Blake draws on stories from parents across the country, like a Delta Force veteran whose son reads his letter every week to a daughter who told her mom it was the best Christmas of her life. Keith and Doug close with their own reflections on what this work means for the families Gimbal serves.Key Topics:Legacy letter writing: how to start, what to include, and how to structure a letter that lastsFatherhood and parenting: communicating love, pride, and belief in ways children carry into adulthoodApology and reconciliation: the five elements of an apology that actually opens a child's heartEmotional intelligence and identity: how parental affirmation shapes how children see themselvesLegacy planning and family values: writing the letter before life makes it urgentLearn more and schedule a conversation at gimbalfinancial.com.

Most families think about generosity emotionally—but few think about it strategically.In this episode, Keith and Caleb break down a surprising way to give generously while improving your tax planning, especially for families with significant assets. When done correctly, generosity doesn’t just improve the world around you—it can reduce taxes, preserve family wealth, and help future generations thrive.We walk through the four ways wealth is typically used over a lifetime: consumption, taxes, loss, and giving. While most people fixate on spending and investing, high-net-worth families often overlook how intentional giving can become one of the most efficient tools in their overall financial plan.You’ll learn:Why taxes are often the biggest “silent consumer” of wealthHow generosity can be structured to reduce tax dragA practical example of using tax-advantaged strategies to benefit family and future generationsWhy “giving later” is often less effective than giving intentionally todayThis is not about charity for charity’s sake. It’s about aligning your values with smart tax planning so your wealth does more than sit on a balance sheet or get lost to Uncle Sam. If you’ve ever wondered whether you can be generous and financially disciplined, this conversation will change how you think about giving.If you want help building generosity into your tax and financial plan, work with us at https://www.gimbalfinancial.com.

Most people believe their worst job was a waste of time. The low pay. The long hours. The frustration. The feeling of being stuck.But what if the job you hated was actually overpaying you?In this episode, Keith and Doug take a candid look at the lessons learned from the worst jobs we’ve ever had—from fast food counters to hotel front desks—and why those experiences quietly shaped skills that paid dividends for decades. This is not a motivational speech. It’s a practical reframing of work, training, and long-term value that especially matters if you’ve ever thought, “I hate my job” or “This can’t be it.”You’ll hear why:A paycheck is often the least valuable part of a jobThe worst roles frequently deliver the best trainingEarly work experiences build empathy, discipline, and perspectiveLearning to think long-term matters more than short-term incomeThis conversation is especially relevant for families, professionals, and parents guiding young adults through early career decisions and for anyone building wealth with intention, not just income.If you’re thinking beyond today’s job and toward a more intentional financial future, we’d love to help.→ Work with us: https://www.gimbalfinancial.com

When a parent begins to decline from dementia, families are often forced to make decisions with no perfect answers—only tradeoffs. In this episode, Keith and Doug sit down with experienced physician, Dr. George Elmes, M.D., to talk candidly about helping aging parents with dementia, navigating end-of-life care, and knowing when it’s time for family members to step in.This conversation goes beyond medical theory and into real-life scenarios families face every day: taking away car keys, recognizing cognitive decline, and deciding when independence must give way to safety. We also explore why dementia is often hidden by those diagnosed, how families miss early warning signs, and why waiting too long can leave everyone reacting instead of planning.You’ll hear a physician’s perspective on quality of life versus quantity of life, how medical technology can extend life without improving it, and why families must think long-term—not just crisis to crisis. Most importantly, we discuss how to approach these moments with compassion, clarity, and the goal of having no regrets.This episode is especially relevant for families with substantial assets who want to coordinate medical decisions with thoughtful financial planning—before a crisis forces rushed, emotional choices.If your family is facing dementia or planning for aging parents, professional guidance matters. We help families align medical realities with financial clarity.Work with us at https://www.gimbalfinancial.com.

When it comes to retirement planning and tax planning, one of the most common questions families ask is: which is best—taxable, tax-deferred, or tax-free accounts? The honest answer is more nuanced than most articles or headlines suggest.In this episode, Keith and Doug break down how taxable accounts, tax-deferred accounts (like traditional IRAs and 401(k)s), and tax-free accounts (like Roth IRAs) actually work and why the “best” option depends on your income, tax bracket, time horizon, lifestyle goals, and giving intentions. This is not a black-and-white decision. It’s more like solving a Rubik’s Cube, where every move affects another side.We walk through real-world scenarios, including retirement income planning, required minimum distributions, charitable giving strategies, and how different asset types impact both taxes today and flexibility later. We also discuss why diversifying your tax exposure can create more control and confidence throughout retirement.If you’re approaching or already in retirement, thinking about legacy planning, or simply want to make smarter decisions with significant assets, this conversation will help you reframe how you evaluate account types and long-term strategy.Work with us at https://www.gimbalfinancial.com.