Up Your Average

Unforgiveness is rarely obvious at first. It doesn’t show up as a single decision. It builds quietly into bitterness, frustration, and ultimately a sense of hopelessness.In this episode, Rick Underhill shares a deeply personal story about how unresolved resentment began to shape his thinking, his behavior, and the direction of his life. What started beneath the surface eventually led to consequences he couldn’t ignore and a realization that changed everything.This conversation goes beyond surface-level advice. It unpacks what it actually looks like to confront that internal weight, take ownership, and choose forgiveness, not as a feeling, but as a disciplined decision that restores clarity and forward momentum.For families focused on building not just wealth, but legacy, this is a critical distinction. Emotional patterns left unchecked can influence relationships, leadership, and long-term outcomes just as much as financial decisions.Work with us at https://www.gimbalfinancial.com.

Caring for aging parents can be one of the most emotional and complex seasons a family will face. For many adult children, the conversation quickly turns to assisted living or facility-based care. But in many cases, home care deserves much more consideration than it gets.In this episode, Keith and Doug interview home care experts David Morgan and Tracy Seals about why staying at home may be a practical and deeply personal option for older adults, especially when dementia, memory changes, or growing daily support needs begin to affect family life. They explore how home care can help preserve dignity, familiarity, and quality of life while giving adult children a more flexible path forward.This conversation is designed for families trying to make wise decisions for aging parents without rushing past options that may be a better fit emotionally, medically, and financially. If you are navigating dementia, evaluating care choices, or trying to support your parents with clarity and compassion, this episode will help you think through the next step.Find solutions for your aging parents at https://seniorhomecompanions.com.Work with Keith and Doug at https://www.gimbalfinancial.com.

Social connection has changed dramatically over the last few decades—and not necessarily for the better.In this episode of Up Your Average, we rewind the clock and compare what social life looked like in the 1960s versus today. Back then, boredom pushed people outside. Kids rode bikes until dark. Neighbors talked on front porches. Community happened naturally.Today, we have more technology, bigger homes, and endless entertainment, but many people feel less connected than ever.So what changed?We explore how social media, digital communication, and modern lifestyles have reshaped the way we interact with each other. While technology has made it easier to stay “in touch,” it may also be replacing the kind of real, face-to-face connection that strengthens families, friendships, and communities.If you're raising a family or thinking about the kind of life you want to build, this conversation may challenge the way you think about connection, community, and time spent outdoors. Because sometimes the most valuable things in life aren't found online. They happen eyeball to eyeball.Work with us:👉 https://www.gimbalfinancial.com

In this episode of Up Your Average, Keith and Doug sit down with Hall of Fame college football coach Mark Richt to talk about the leadership principles that carried him through one of the most competitive environments in sports.Coaching at the highest level of college football, Richt learned quickly that even the best leaders only win a little more than half the time. If the greatest coaches make the Hall of Fame at around a 65% win rate, how do leaders maintain confidence, identity, and perspective when things don’t go their way?Mark shares common-sense leadership lessons about handling criticism, separating your identity from your job, and leading people with character and clarity. Whether you're leading a team, running a business, managing investments, or guiding your family, these insights apply far beyond football.If you're looking for practical leadership wisdom from someone who has led at the highest level of college football, this conversation with Mark Richt delivers insights that stand the test of time.Work with us:👉 https://www.gimbalfinancial.com

What if your self-confidence could increase 60–70% in just eight weeks?In this episode, Caleb and Libbi take a deep dive into the Dale Carnegie Course with Steve Haines to learn why high performers continue investing in personal development decades after achieving financial success.Self-confidence isn’t personality—it’s a skill. We explore how structured training improves communication clarity, reduces stress by up to 50%, strengthens leadership presence, and deepens relational awareness. For families managing careers, investments, and legacy planning, those soft skills often determine long-term outcomes more than raw intelligence or capital.We also discuss:Why phone distraction is eroding real connectionHow better listening improves influenceThe relationship between confidence and stress reductionWhy stepping outside your comfort zone accelerates growthThe measurable impact of communication trainingIf you’ve built financial capital but want stronger relational capital, this conversation will challenge you to think differently about self-development.Build both financial and personal confidence by connecting with our team at Gimbal Financial: 👉 https://www.gimbalfinancial.comStart the Dale Carnegie Course for yourself by connecting with Steve Haines:👉 https://indy.dalecarnegie.comYour portfolio matters. But so does the person managing it.

How do you retire without anxiety? For high-net-worth families, retirement planning isn’t just about growing wealth—it’s about spending it wisely and confidently.In this episode of the Up Your Average, Keith and Doug unpack one of the most overlooked transitions in financial life: shifting from saving mode to spending mode. If you’ve built over $500,000 in investable assets, the question is no longer “Can I grow this?” but “Can I enjoy this—without running out?”We explore:The psychology of the spender vs saverWhy flatlining your wealth at 65 may be perfectly rationalThe difference between accumulation and decumulation strategyHow to eliminate guilt and anxiety around retirement spendingWhat worry-free retirement planning actually requiresFor many disciplined savers, the hardest part of retirement is giving yourself permission to spend. But you only get one retirement. The goal is not just financial security, but financial freedom.If you want a retirement income strategy built for confidence, connect with our team at Gimbal Financial.👉 Work with us: https://www.gimbalfinancial.com

Artificial intelligence is everywhere. But can AI actually help improve your cash flow, or is it just another shiny distraction? In this episode, Doug breaks down how artificial intelligence tools can be used practically to bring clarity, discipline, and efficiency to your cash flow, especially for families navigating rising income and the quiet threat of lifestyle creep.Many high-earning families don’t struggle with income—they struggle with visibility and control. As spending grows alongside success, cash flow often becomes reactive instead of intentional. We discuss how AI can help identify spending patterns, surface inefficiencies, and support better decision-making without removing the human judgment required for long-term financial planning.You’ll also learn why AI is not a replacement for wisdom, values, or a comprehensive financial strategy and how over-reliance on automation can actually accelerate lifestyle creep if left unchecked. The real power of AI lies in pairing it with a disciplined cash flow framework and experienced financial guidance.If you want to use technology to support your financial goals, this conversation will help you think more clearly about how AI fits into your wealth strategy.👉 Want professional guidance applying this to your own finances?Work with us at https://www.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.

What can you really accomplish in your first year as a financial advisor?In this episode, Keith sits down with Caleb Tyner for an honest, behind-the-scenes conversation about the lessons that only come from being in the trenches—working with real families, navigating real markets, and learning what it actually takes to give meaningful financial advice.From mastering financial advisor fundamentals to learning how to communicate clearly without industry jargon, this discussion explores what surprised Caleb most during year one on the job. We talk openly about confidence, decision-making, client relationships, market volatility, and why humility and lifelong learning matter far more than having all the answers.If you’re someone thinking seriously about becoming an financial advisor, this episode offers valuable perspective on how advisors grow, how experience compounds over time, and why long-term thinking beats short-term tactics. You’ll also hear why relationship-based advising, emotional discipline, and clear communication are essential when helping families steward wealth across decades, not just market cycles.If you’re looking for thoughtful, long-term financial guidance, work with us at https://www.gimbalfinancial.com.