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.

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

Cash flow is more than a budgeting exercise—it is the reality check that determines whether your money is truly supporting the life you want to live.In this episode, Doug walks through a comprehensive guide to cash flow, breaking it down into practical, real-world terms for families navigating career transitions, major purchases, retirement planning, or simply trying to create more financial margin. From wages and business income to taxes, expenses, investments, and giving, cash flow reveals not just where your money goes but what it values.You will learn why you should review your cash flow every year, how cash flow impacts net worth, why memories and experiences matter just as much as numbers, and how to use cash flow as a tool for better communication with your spouse and familyThis episode introduces a simple framework for evaluating money in, money out, and net cash flow—along with practical steps you can implement in under 90 minutes using tools you already have.If you want help turning your cash flow into long-term financial stability, we would love to talk.👉 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.

Planning a wedding is one of the most meaningful (and expensive) decisions a couple will make. Yet many families approach wedding planning without the guidance they need to avoid unnecessary stress, wasted money, and regret. In this episode, Keith and Doug interview wedding planner Elizabeth Owens to break down 10 essential wedding planning do’s and don’ts every couple should consider before the big day.Drawing from real-world experience with couples, Elizabeth discusses what actually matters versus what simply adds cost without adding value. From guest lists and vendors to timing, food choices, and flow of the day, this conversation helps couples make confident, informed decisions that align with both their values and their finances.You’ll learn why:→ Smaller, intentional guest lists often lead to better experiences→ The right vendors, especially DJs and coordinators, can make or break the day→ Trends like first looks, private last dances, and late-night snacks are growing in popularity→ Overspending on décor rarely delivers lasting impact→ Preparation leads directly to peace on your wedding dayWhether you’re newly engaged or helping a child plan their wedding, this episode offers practical wedding planning advice designed for families who care about long-term financial health, not just one event.If you want guidance that goes beyond the wedding day and supports your broader financial life, we’d love to help.🔗 Work with us at https://www.gimbalfinancial.com🔗 Work with Elizabeth at https://www.savethedaysisters.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.

Don’t let the world persuade you.In an age of constant noise, instant information, and cultural pressure, wisdom has become both rare and invaluable. In this episode, Keith and Doug explore what it means to live wisely in foolish times, drawing practical insight from ancient principles that remain deeply relevant to modern financial and family decisions.You’ll learn the difference between knowledge and wisdom, how foolish financial patterns quietly erode wealth, and why the people you spend time with matter just as much as the plans you make. For families with significant assets, the stakes are higher. Wise decisions compound—just like foolish ones. This episode is designed to help you slow down, think clearly, and align your personal and financial life with what truly matters.If you’re looking for a financial partner who prioritizes wisdom over hype and long-term clarity over short-term noise, we’d be honored to help. Learn more about working with us at https://www.gimbalfinancial.com.