Episode 43: Beyond the Pavement with Frank Trotter


What do banking and backcountry exploration have in common? More than you’d think! In this episode of the On Adventure, I sit down with Frank Trotter—banking pioneer, entrepreneur, and avid adventurer. From his early days racing cars in Europe to co-founding EverBank and now launching Battle Bank, Frank shares how his career has been driven by innovation and a passion for pushing boundaries. But it’s not all business—Frank also dives into his love for outdoor exploration, from summiting 14ers in Colorado to backcountry treks in Argentina.

We talk about the lessons learned from extreme environments, the balance between risk and reward, and how his entrepreneurial spirit aligns with his drive for adventure. Plus, we dive into the incredible Excellent Adventures group and why surrounding yourself with the right people makes all the difference—whether in business or the wilderness.

Episode Highlights:

  • [2:00] Frank’s journey from hockey in St. Louis to racing cars in Europe
  • [6:30] The evolution of internet banking and why he’s launching Battle Bank
  • [10:45] The hidden ways big banks profit off their customers
  • [18:20] The Excellent Adventures hiking group and its impact on Frank’s outdoor pursuits
  • [24:15] Facing physical challenges—how a medical study changed his ability to keep exploring
  • [35:40] The connection between adventure, mindfulness, and perspective
  • [48:00] Knowing when to push forward and when to turn back—lessons from the mountains
  • [52:30] What’s next? Zion, GoPro Games, and upcoming adventures

Links & Resources:

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Episode 42: Endurance, Exploration, and the Art of Adventure with Roy Malone


What does it take to push your body and mind to the limit for days on end—while relying entirely on a team? The answer is epic!  In this episode, I sit down with seasoned adventure racer Roy Malone, who has spent the past 24 years competing in some of the toughest endurance races in the world. From trekking through the jungles of Fiji to navigating the badlands of North Dakota, Roy shares the highs, the lows, and the life lessons that come from competing in these multi-day, non-stop races.

We dive deep into the mental and physical grit required to finish these extreme challenges, the team dynamics that make or break success, and how adventure racing parallels the business world in unexpected ways. Roy also talks about his new venture, TerraVenture, which is bringing adventure to everyday explorers who crave the thrill of the unknown. If you’re curious about endurance racing, risk-taking, or just want to hear some unbelievable stories from the wild, this is an episode you won’t want to miss!

Episode Highlights

[00:00] – Welcome and introduction to Roy Malone
[02:45] – How Roy balances adventure racing, family life, and a career in finance
[08:10] – What is adventure racing? A deep dive into the sport’s extreme challenges
[12:30] – The mental game: Handling sleep deprivation, exhaustion, and team dynamics
[22:00] – Hallucinations on the trail: Roy’s wildest experiences in multi-day races
[31:15] – The toughest race of Roy’s career and why Fiji pushed him to his limit
[40:45] – TerraVenture: Roy’s mission to bring adventure racing to a broader audience
[55:00] – What’s next? How long Roy plans to keep competing and where he’s headed next

Links & Resources

🔗 Learn more about Team Bones Adventure Racing: BonesAdventure.com
🔗 Explore Roy’s new company, TerraVenture: Terra-Venture.com
📧 Connect with Roy via email:

Enjoyed the episode?

If you loved this conversation, be sure to subscribe, rate, and review the show! And don’t forget to share it with a fellow adventurer. 🚀🎙️

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Episode 41: A Journey of Resilience and Rediscovery with Jenna Carroll


In this episode of The On Adventure Podcast, I sit down with Jenna Carroll, a hiking guide and endurance athlete who transformed her life by stepping off the corporate treadmill and onto the Appalachian Trail. Jenna shares her incredible journey, from her early days as a basketball star and management consultant to finding her passion for long-distance hiking and trail running. We delve into her 2021 northbound thru-hike of the Appalachian Trail, her life-changing decision to make the outdoors her career, and her remarkable return to the trail in 2023 to attempt a self-supported fastest known time (FKT).

Along the way, Jenna reflects on the emotional highs and lows of solo hiking, the invaluable lessons of community and resilience, and how nature continues to fuel her creativity. Whether you’re a seasoned hiker or just curious about life’s unpredictable paths, Jenna’s story is sure to inspire.

Episode Highlights:
[2:10] – Introducing Jenna Carroll: From basketball star to corporate life to hiker-extraordinaire.
[6:45] – Jenna’s first thru-hike: Why she left her desk job to tackle the Appalachian Trail.
[15:30] – Overcoming freezing temps on Blood Mountain: Jenna’s turning point just four days into the trail.
[24:40] – Post-trail life: Moving to Asheville, finding her calling as a hiking guide, and rediscovering creativity through poetry.
[39:00] – Tackling personal endurance challenges: Jenna’s first 50K and her epic Montreat trail day.
[43:50] – Attempting the self-supported FKT: 63 days, 2,200 miles, and lessons learned on the Appalachian Trail.
[57:00] – The value of community: How connection and support fueled Jenna’s solo adventures.
[1:02:30] – What’s next for Jenna: A 100-mile race, guiding trips, and continuing her journey in Asheville.

Links & Resources:

  • Blue Ridge Hiking Company
  • Books that inspired Jenna:
    • Thirst: 2600 Miles to Home by Heather “Anish” Anderson
    • A Beautiful Work in Progress by Myrna Valerio
  • Learn more about Mount Mitchell, the highest peak in the eastern U.S. here.

Closing:
If you enjoyed this episode, please take a moment to rate, follow, and share On Adventure! It means the world to us and helps us reach more adventure seekers like you. Until next time, I hope you find your next great adventure.

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Episode 38: From the Wilderness to the Operating Room with Dr. Tommy Gavigan


In this episode of the On Adventure Podcast, I catch up with an old friend and fraternity brother, Dr. Tommy Gavigan. From our days at the University of North Carolina to his current life as a practicing surgeon in Charlotte, Tommy’s journey has been anything but conventional. After college, Tommy spent nearly a decade guiding teenagers into remote wilderness areas with Moondance Adventures—experiences that shaped not only his leadership but also his path into medicine.

We explore the connection between pushing past your comfort zone in the backcountry and managing high-stakes scenarios in the operating room. Tommy shares incredible stories of adventure, personal growth, and how these experiences molded his outlook on life. Now in his “Adventure 3.0,” he reflects on fatherhood, future aspirations, and why challenging yourself—physically, mentally, and emotionally—is key to living fully.

This episode is a deep dive into why we seek hard things, what we gain on the other side, and how adventure can prepare us for life’s biggest moments.

Episode Highlights

  • [1:10] – Introduction: Reconnecting with Tommy and his unique journey post-UNC.
  • [4:45] – The Moondance Adventures: From green teenagers to life-changing moments in the wilderness.
  • [12:30] – Real backcountry challenges: Lightning storms, hypothermia, and a rare grizzly bear encounter.
  • [18:00] – Service through adventure: Teaching kids leadership, grit, and resilience.
  • [31:30] – From outdoor leader to surgeon: Tommy’s leap into medicine and his pivotal “letter to the future self.”
  • [39:20] – Adventure 3.0: Parenthood, teaching his son the outdoors, and future dreams.
  • [42:15] – Managing high-stakes stress: Lessons from the wilderness to the operating room.
  • [45:30] – What’s next? Personal peaks, challenges, and expanding the comfort zone.

Links & Resources

Check out this episode!

Episode 37: Paying off $225,000 of student loan debt to fuel big adventures with Matt Miner


In this episode of the On Adventure Podcast, I sit down with my friend and former colleague, Matt Miner, to talk about his unique take on adventure. From growing up in Seattle and Tucson to now running his own wealth management firm, Matt shares the pivotal moments that shaped his life and career.

We explore what it means to embrace life’s challenges, how intentional planning creates opportunities, and why staying true to your values makes all the difference. Whether it’s his love for the outdoors, paying off substantial debt, or helping his kids prepare for adulthood, Matt’s story is full of practical wisdom and honest reflections.

If you’ve ever wondered how to navigate big life transitions while staying grounded, this conversation is for you.

Timeline Summary

[00:00] Introduction – Welcoming Matt Miner and a look at his journey.
[02:00] Roots and Resilience – Growing up in Seattle, moving to Tucson, and finding adventure outdoors.
[06:30] Career Transitions – From corporate roles to entrepreneurship: lessons learned.
[12:00] Debt-Free Milestone – How Matt’s family paid off $225,000 in debt and moved forward.
[19:00] The Outdoors Connection – Hunting, backpacking, and building community.
[26:15] Journaling for Growth – Using writing to reflect and move forward.
[33:45] Family Legacy – Preparing the next generation with life skills and values.
[36:00] Key Takeaways – The power of knowing your values and making intentional choices.

Links & Resources

Closing Remarks

If you enjoyed this episode, subscribe to the show and leave a review. Your support helps us bring more thoughtful conversations like this one to life.

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Election Day Reflections

I sent this letter out initially in the midst of Election Day.  There obviously was a lot of energy in the air. Anticipation runs high, and the headlines were filled with speculation on what the choices mean for the markets. But here’s the perspective we can hold: while political outcomes may feel momentous, they rarely dictate the path of long-term investments.

Here are some helpful reminders as we continue to move through this election cycle:

Election outcomes and stock market outcomes are not correlated.

Election results and market returns are often far less connected than the news might suggest. For example, research by Fidelity has shown that, over time, the S&P 500 has performed comparably under both Democratic and Republican administrations—regardless of who held Congress. Since 1976, every market sector has had periods of growth during both Democratic and Republican terms. Across election cycles since 1976, each sector has performed well at times, regardless of which party holds the White House.  The markets, it seems, march to a rhythm of their own.

Cause and effect in the markets is rarely direct.

During election seasons, it’s tempting to act on predictions about how new socioeconomic policies might influence the markets. However, even the most astute commentators cannot reliably forecast market reactions to political shifts. Financial writer for Forbes John Jennings compares this to scientists who understand why volcanoes occur but cannot predict each eruption. In markets, just as in nature, the ability to explain an event is different from the ability to foresee it.

Elections come and go; your investments have a much longer time horizon.

We may vote for a president every four years, but your portfolio is designed to endure and grow over decades. Data spanning nearly a century, illustrated by Dimensional Fund Advisors, shows that U.S. equities have consistently trended upward, no matter which party was in power. Staying the course remains the most effective path forward for reaching your long-term goals.

So as the election buzz fills the air, know that your investments are positioned for resilience. Let’s keep our sights on the horizon, with our long-term objectives leading the way.

Steady onward.

 

Thanksgiving Reflections: Finding Financial Peace, Presence, and Genuine Joy in the Season

Thanksgiving marks a pause for many of us in the whirlwind of daily life. I love it for that.  For a few days, we gather with family and friends, enjoying good food, laughter, and conversation. Yet, the season can be bittersweet—a time of reflection and celebration that’s often overshadowed by the stress of holiday expenses and the pressures of hosting or attending gatherings or other family dynamics that are just hard to put a finger on. As we enter this Thanksgiving season, maybe we consider a different approach: focusing on financial stability, being fully present with our loved ones, and finding genuine enjoyment rather than just getting through it.  Yeah, I know, you’ve heard this before, but hear me out.

Cultivating Financial Stability…it’s not about the money

Financial stability isn’t about extravagance; it’s about having peace of mind and the freedom to make choices aligned with our values. For many, holidays add a financial strain, but it doesn’t have to.  Trust me, this is the part of the article where I’m talking to myself, so feel free to listen in.

Financial stability begins in the mind. It’s about adopting a mindset that values contentment over accumulation, embracing a sense of “enough” rather than striving for more. This mindset allows us to approach the holidays with gratitude for what we have rather than stressing about what we lack. Thanksgiving invites us to step back and see our resources—time, energy, and money—as tools to be used intentionally, not indicators of success or happiness. When we feel secure in what we have, we’re less tempted by the holiday urge to overspend or overextend.

The Power of (Being) the Present

With today’s technology, it’s easy to be physically present with family while mentally absent—our thoughts divided between notifications, emails, and to-do lists. I truly believe that there is no such thing as multi-tasking…our brains are hardwired in this way.  So, if you’re staring at your phone, you’re not present with those around you.  One of the most profound gifts we can give during Thanksgiving is the full presence of our attention. Choosing to leave phones in another room, engage in conversation, and listen to each family member’s story without distraction can transform our gatherings. These moments don’t require perfection in family dynamics; they only need our open ears and a willingness to embrace others as they are. 

Being fully present also applies to ourselves. Instead of rushing to fit every seasonal obligation, we can consciously slow down, taking time to recharge. Whether it’s a quiet morning walk, reading a book, or simply breathing deeply before a meal, these moments allow us to enjoy Thanksgiving with gratitude and grace rather than as an item on a checklist.

Enjoying, Not Enduring, the Season

Many people experience the holidays as something to endure rather than enjoy—a time of fulfilling social expectations or family obligations. However, true enjoyment comes from engaging with the season in a way that’s meaningful to us personally. For some, this might mean traditional festivities; for others, it might look like an intimate gathering or even a quiet Thanksgiving hike. The key is to spend the day in a way that brings joy and connection, free from imposed expectations.

Setting boundaries on how we celebrate doesn’t diminish the holiday’s value—it enhances it. When we choose celebrations that align with who we are, we foster genuine gratitude. If that means opting for a small dinner, skipping crowded stores, or using Thanksgiving to volunteer instead, so be it. Our traditions should reflect what brings us joy, not what we feel pressured to maintain.

Thanksgiving is a time to reflect on abundance—of love, health, relationships, and even the lessons learned through challenges. I want us all to pursue our Great Life right now, and this holiday season is a great opportunity to pursue it with the people that we care most about.  This season, let’s make it less about stretching our resources thin and more about stretching our capacity for gratitude. Embrace simplicity, give the gift of presence, and choose joy over obligation. In doing so, Thanksgiving becomes more than a holiday; it becomes a practice in contentment, reminding us that true wealth is measured by the richness of our experiences and the depth of our connections. 

Thanks for listening without judgment to my inner dialogue.

 

Episode 34: The 5 Elements of Adventure with Matt Walker


In this special episode, I’m excited to bring you an insightful webinar with adventure coach and psychologist Matt Walker. Known for his unique blend of mountain climbing experience and psychological expertise, Matt shares how the concept of adventure can shape not only extreme expeditions but also our everyday lives. In this session, he takes us through his recent solo climb of Manaslu, one of the highest peaks in the world, and how it taught him the importance of living adventurously. Learn about the five essential elements of adventure and how you can apply them to your own life, whether you’re scaling mountains or navigating day-to-day challenges. This is an inspiring episode that will push you to think deeply about your own adventures—big or small!

Tune in to hear Matt’s captivating stories and insights on high endeavor, uncertainty, total commitment, tolerance for adversity, and the power of companionship.

Episode Highlights:
[2:00] – Introducing Matt Walker: From psychologist to extreme adventure guide
[4:10] – What is adventure? Challenging conventional definitions
[11:00] – Matt’s solo climb on Manaslu: confronting extreme conditions and overcoming obstacles
[15:30] – The Five Elements of Adventure: High endeavor, uncertain outcome, total commitment, tolerance for adversity, and great companionship
[21:00] – How Matt integrates his family into his adventurous life
[27:45] – Climbing in extreme altitudes: life in the death zone
[33:00] – The importance of staying present and focused during difficult journeys
[40:00] – Why adventure isn’t just for mountaintops: Applying the elements of adventure to daily life
[45:00] – Listener Q&A: Overcoming psychological barriers to adventure

Links & Resources:

Closing Remarks:
If you enjoyed this conversation with Matt Walker and learned something new about how to bring more adventure into your life, don’t forget to rate, follow, and share this podcast with friends! And if you’re ready to embark on your own adventure, start by subscribing to our newsletter for more tips and resources. Until next time, keep pursuing your great adventure!

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How to Plan a Big Family Trip Without Becoming the Griswold’s

Research shows that spending money on experiences often brings more lasting joy than buying more “stuff.” Now imagine the joy and connection that comes from planning a big family vacation—one that creates memories for generations to come. I believe Clark Griswold knew the value of such trips, but he clearly had trouble pulling it off.  While getting everyone aligned may feel challenging, it’s also what makes the journey worthwhile. Let’s go over some key steps to ensure your family adventure is one for the books.

Open the Dialogue Early

Nobody enjoys being dragged along on someone else’s vacation. The key to a successful family trip is making sure everyone feels included from the start. Whether some family members are retired with flexible schedules or others are balancing school, work, and activities, it’s important to consider everyone’s situation.

Start by agreeing who is the ‘champion’ of the planning overall.  Someone must be responsible for organizing the communicating the plans.  Then start gathering input from everyone—use a group video chat, shared document, or a family meeting to talk through options. This gives everyone a chance to voice what works for them and helps you find common ground. Collaboration early on can make all the difference in pulling off a trip everyone enjoys.  Obviously this will look different if you are traveling with younger kids, but you know that they have opinions too!

Balance Togetherness and Individual Time

When planning a vacation for a large group, it’s crucial to strike the right balance between shared experiences and personal space. Not everyone will want to do the same activities, and that’s okay. Whether it’s golfers heading out for a round while others enjoy a spa day or different groups exploring different sights, the key is flexibility.

Plan a few moments for everyone to be together—like beach time or family dinners—but also allow space for each person to pursue what excites them. This balance will help everyone enjoy the trip in their own way without feeling overwhelmed or restricted.

Be Clear About the Budget

Few things create tension faster than money talk, especially in a family setting. If each family is paying their way, aim to pick a destination that fits most people’s budgets. If one person is paying for it all (ie, mom and dad), be totally clear about that from the beginning.  This ensures everyone can enjoy the trip without feeling financially strained.  Or worse, living in the uncertainty of ‘who is paying for what’?

If you are generously covering the cost, having a clear budget in place is even more important. Setting limits upfront helps ensure you don’t overstretch yourself financially, allowing you to fully enjoy this special experience with your loved ones.

Thinking ahead about your travel budget and ensuring that this family vacation fits within your broader financial goals will allow you to focus on making memories instead of managing costs.  This is what it is all about!

 

I have a Lump Sum in Cash – Should I Invest It Right Away?

Whether it’s a work bonus, inheritance, or proceeds from selling a business, receiving a large sum of money can leave you wondering, “What do I do with it now?” It’s natural to feel a bit stuck—especially with the market going through its usual ups and downs. Do you invest it all at once, or spread it out over time?

This is a common question, and honestly, it’s understandable. We all worry about making the wrong move—invest too soon and the market might drop; wait too long and you could miss a rally. But there’s no need to over-complicate it. Let’s break down your options.

Start with Your Goals

Before diving into the numbers, ask yourself: What do I want this money to do for me?

If you’ve got short-term goals, like paying for your kid’s college tuition in the next few years, you may want to lean toward more stable, less risky investments—think bonds, bond funds, or CDs. These are less likely to be impacted by the market’s short-term swings.

On the other hand, if this money is for long-term goals, like retirement, then putting it into the stock market might make sense. Over the long haul, markets tend to rise, despite the short-term ups and downs.

Lump-Sum vs. Dollar-Cost Averaging

Now, should you invest all the cash at once or spread it out?

Lump-sum investing gets all your money into the market right away, which could be great if the market’s on the rise. But no one can predict the future, and there’s always a chance the market dips right after you invest. If that possibility stresses you out, dollar-cost averaging (DCA) might be more your speed.

With DCA, you invest a set amount regularly—say, $1,000 a month for a year. When prices are high, you buy fewer shares; when prices drop, you buy more. It’s a steady approach that smooths out market fluctuations over time.

However, here’s the kicker: research shows that lump-sum investing tends to outperform dollar-cost averaging about 68% of the time. So, if your main goal is maximizing returns, lump-sum might be the way to go. That said, the difference in returns between the two strategies isn’t massive, so if dollar-cost averaging helps you sleep better at night, it’s worth considering. After all, the last thing you want is to panic and sell when the market dips.

The Bottom Line—Don’t Wait

Whether you go with lump-sum investing or dollar-cost averaging, the most important thing is not to delay. Holding onto cash means missing out on potential growth from stocks and bonds. And trying to time the market? That’s a tough game to win.

In fact, studies show that average investors who attempt to time the market often miss out—by as much as 5.5% compared to just sticking with the S&P 500. So, whatever you decide, get started. Both approaches will help you benefit from the market’s long-term upward trend, which is key to achieving your financial goals.

Need help figuring out which approach works best for you? Reach out, and we’ll walk through it together.