Episode 55: From Conservation to Kilimanjaro – A Life of Meaningful Struggle with Tom Hicks


What does it really mean to suffer with purpose? In this episode of On Adventure, I sit down with conservationist and ultra-endurance athlete Tom Hicks – a man whose journey is as layered as the landscapes he climbs. From leading anti-poaching efforts across Africa and Asia with the David Shepherd Wildlife Foundation to tackling brutal challenges like Ironman races and high-altitude expeditions, Tom’s life is defined by intentional hardship, deep introspection, and relentless forward motion.

We dive into the heart of resilience, why discomfort can be transformative, and how a former rugby coach found meaning in the mountains. Tom also shares his connection with previous On Adventure guest Holly Budge and his plans to lead a new team to the summit of Kilimanjaro. Whether you’re an aspiring adventurer, a mindset junkie, or someone wrestling with self-doubt, this episode delivers a powerful reminder: growth is never linear, and purpose is often found in the pain.


Episode Highlights:

[3:00] – Fighting global wildlife crime: Tom’s work with the David Shepherd Wildlife Foundation
[8:00] – The brutal truth about poaching, organized crime, and the risks of field conservation
[12:00] – From being told he’d never succeed to becoming a conservation leader
[18:00] – Mentoring the next generation: the importance of presence and vulnerability
[24:00] – The “circuit breaker” mindset tool to quiet negative inner voices
[29:00] – What drives us to endure suffering in pursuit of meaning
[38:00] – A life-or-death lesson on Lenin Peak – and why good decision-making matters
[45:00] – Remembering Dixie Dansercoer and how it reshaped Tom’s risk tolerance
[54:00] – Emotional regulation in chaos: the power of calm leadership
[59:00] – Balancing ambition, burnout, and building a team for Kilimanjaro


Links & Resources:


Connect with Tom:
Have questions about conservation, endurance training, or joining the upcoming Kilimanjaro team? Reach out to Tom directly on LinkedIn or Instagram – he’s always happy to connect with fellow adventurers and curious minds.


Enjoyed this episode?
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Traveling on Purpose: Turning Luxury Vacations into Meaningful Milestones

For many families, vacations are about rest and recreation – time to unwind, see the world, and enjoy hard-earned success. But for those with significant resources, there’s an opportunity to take travel beyond luxury and create something far more lasting: purposeful travel.

Purposeful travel blends the comfort and adventure you expect with intentional goals – strengthening family bonds, serving communities in ways that leave a legacy, or cultivating personal growth through quiet reflection. These trips become milestones, remembered not just for where you went, but for how they shaped your family’s story.

Here are three purposeful approaches that resonate especially well for families who want their travel to matter as much as their investments:

  1. Multi-Generational Adventures that Forge Family Connection

When a family spans multiple generations, gathering everyone under one roof – or even in one country – can be rare. A purposeful family trip creates an intentional space to connect across ages, combining luxury comfort with shared challenges or experiences.

Think of chartering a private expedition yacht in Alaska where grandparents and grandchildren alike participate in guided wildlife research. Or a curated trek through Patagonia, complete with private guides and lodges, where each family member contributes – whether it’s navigating a trail or preparing a shared meal one evening.

The goal isn’t just to “go somewhere” but to actively create shared experiences that knit generations together and build the family narrative. These trips often spark traditions that become part of the family’s legacy.

How to get started:

• Engage a travel advisor who specializes in high-end, family-oriented experiences to ensure logistical ease and privacy.

• Choose a cause or skill that resonates with your family values – conservation, cultural preservation, or even an artistic pursuit.

• Plan structured reflection time, like nightly fireside conversations or a shared family journal to capture insights along the way.

  1. Personal Retreats for Renewed Perspective

Wealth often comes with significant complexity…it’s the often-overlooked paradox of ‘more.’ The pressures of leadership, decision-making, and public life can be relentless. Purpose-driven solo retreats – or even couples retreats – offer rare opportunities to disconnect from constant demands and recalibrate priorities.

Picture a guided silent retreat in the Swiss Alps with world-class amenities, or a secluded desert lodge designed for deep meditation and personal reset. These environments strip away distractions and offer clarity, allowing you to return not just refreshed, but re-centered on what matters most.

How to get started:

• Consider retreat centers that balance privacy with top-tier wellness programming – places that honor both comfort and introspection.

• Recommendations from friends that have gone before are helpful!

• Build a loose itinerary: include guided mindfulness sessions, private hikes, or curated reading lists to deepen the experience.

• Plan for post-retreat integration: a few days of quiet transition before re-engaging fully with work and family life. This is always important so we don’t blow right back into life as usual.

  1. Philanthropic Travel with Measurable Impact

For many affluent families, travel is also a chance to align lifestyle with legacy. Philanthropic adventures – sometimes called “impact travel” – allow you to explore remarkable destinations while supporting initiatives that matter to your family.

Imagine funding and participating in a reef restoration project in the Maldives, or helping construct sustainable water systems in a remote African village – while your family experiences the local culture and learns firsthand about the challenges and solutions. These trips can instill gratitude and broaden perspective for younger generations, while also tangibly advancing causes you care about.

How to get started:

• Partner with established philanthropic travel organizations to ensure projects are ethical, sustainable, and genuinely needed.

• Define your family’s core values (education, conservation, community) and seek projects that align with them.

• Combine service with adventure – balance meaningful work with opportunities to explore and celebrate the destination.

Why This Matters for Families of Means

There is no question that I am bent towards looking at vacation as an escape. I do not think that there is anything inherently wrong with viewing time away from daily life in this light. Sometimes, it is exactly what is needed for recharging.

However, the broader point here is that there is another angle that can be considered. Purposeful travel reframes vacations from “escape” to “investment” – not in dollars, but in relationships, perspective, and legacy. It creates shared experiences that deepen connection, foster gratitude, and remind everyone what your resources are really for: living a meaningful life, not just an affluent one.

These trips also help younger generations see wealth differently – not as entitlement, but as responsibility and opportunity. They become part of the family culture, shaping how future decisions about giving, living, and investing are made.

Next time you plan a trip, ask: What could this mean for our family beyond rest and luxury? The answer might turn your next vacation into one of the defining chapters of your family’s story.

Episode 50: What My Son Taught Me About True Strength and Courage with Hudson Self


In this heartfelt episode of the On Adventure Podcast, I sit down with a younger Everyday Explorer, my son Hudson, for a conversation that redefines what adventure truly means. While we often explore tales of physical challenge and bold travel, this episode takes us on an inward journey—a story of persistence, identity, and the courage to live fully despite daily challenges. Hudson lives with Prader-Willi Syndrome (PWS), a rare genetic condition, and he brings us into his world with sincerity, wisdom, and humor.

We talk about what it’s like to grow up with PWS, the unique joys and struggles that come with it, and how it’s shaped Hudson’s perspective on life. He shares how adventure isn’t just found on mountaintops or across oceans—it’s in the relationships we build, the obstacles we face, and the love we share. From exploring WWII history in Europe to dreaming about the Great Wall of China, Hudson reminds us that the truest adventures are often the ones that take place in our own hearts and homes. This episode is not just a story of difference—it’s a story of belonging, resilience, and the extraordinary power of being seen and included.

⏱️ Timeline Summary

  • [0:00] – Meet Hudson Self and an introduction to Prader-Willi Syndrome Awareness Month

  • [1:00] – Hudson’s heartfelt presentation on living with PWS

  • [3:00] – Sharing his passions and personal joys beyond the diagnosis

  • [5:00] – The importance of inclusion and being treated like everyone else

  • [7:00] – Discussing the constant challenge of hunger with PWS

  • [9:00] – How PWS brought meaningful relationships and mentors into Hudson’s life

  • [10:00] – Visiting historical sites in Europe and the emotional impact of Normandy

  • [12:00] – Dreaming of a future adventure to the Great Wall of China

  • [13:00] – Favorite memories from a Jurassic-themed trip to Hawaii


🔗 Links & Resources


🎧 Closing Thoughts

This episode is a powerful reminder that adventure comes in many forms. If Hudson’s story moved you, inspired you, or made you think a little differently, please consider rating, following, and sharing the podcast from our YouTube (this is brand new!), Instagram and Facebook pages (this is new too!). And don’t forget to leave a review—we’d love to hear from you.

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Episode 48: Beautiful rebellion and choosing creativity over conformity with Thad Cockrell


In this episode of the On Adventure Podcast, I sit down with singer-songwriter and creative visionary Thad Cockrell for a conversation that took an unexpected but deeply inspiring turn. Thad opens up about his journey from wrestling mats and seminary halls to Nashville stages and international acclaim—all while forging a career based on creativity, authenticity, and saying a bold “yes” to uncertainty. We explore what it means to create from love rather than fear, and how rebellion, doubt, and wonder can be sacred tools on the creative path.

From Thad’s bold decision to sell his album for $100 directly to fans, to the moment Jimmy Fallon discovered his song in a hardware store, this conversation will challenge the way you think about success, security, and what it means to truly create without an agenda. Whether you’re an artist, entrepreneur, or just someone seeking a more intentional life, this episode is packed with insight and soul.


⏱️ Timeline Summary:

[1:45] – Thad on how creativity is a daily act of defeating doubt
[4:00] – Why you can’t conform and create at the same time
[9:55] – The childhood moment that sparked Thad’s unexpected path toward music
[14:20] – Discovering Neil Young and realizing, “This is what I’m supposed to do”
[24:30] – Moving to Nashville and the wild story of unexpected community support
[33:50] – Thad’s transformative shift from insecurity to creating from security
[44:00] – How he released his latest album for $100 and made more than 13 years on Spotify
[49:50] – What it means to create from the present moment with no need for external validation
[56:00] – Thad’s big dream: building a new music economy and going platinum without streaming


🔗 Links & Resources:


🙌 Enjoyed This Episode?

If this conversation sparked something in you, I’d love for you to leave a review, share the episode, or hit that follow button. Your support means the world and helps more people find the podcast. Thanks for being part of the adventure!

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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 31: Turning Tragedy Into Purpose – An Adventurous Journey with Clay Sanders


In this deeply moving and inspiring episode, I sit down with Clay Sanders, a man whose life is marked by profound adventures, resilience, and purpose. Clay shares stories of his adventurous spirit, from crossing the country on an Elliptigo to running the Leadville 100 ultra marathon, all while balancing a successful career as a dentist. But beyond the adventures, Clay opens up about the tragic loss of his son, Joel, to opioid addiction, and how that event spurred him into action, continuing his son’s legacy by raising awareness about addiction stigma.

We dive into Clay’s perspective on how adventure can be both structured and unpredictable, and how his journey to honor his son led him to discover even deeper connections with others, both in the U.S. and across the globe. You won’t want to miss Clay’s powerful reflection on the process of navigating life’s challenges and the wisdom he has gained along the way.

Timeline Summary:

[2:22] – Clay shares his move from Western North Carolina to Colorado and how he adjusted to life at higher altitudes.
[6:17] – Adventures in ultra-running and what led Clay to tackle the notorious Leadville 100.
[14:30] – The impact of high altitude on ultra-endurance races and how Clay trained for the Leadville 100 while living at sea level.
[28:19] – Tragedy strikes: Clay discusses the loss of his son Joel and how that transformed his life and purpose.
[32:00] – The journey across the U.S. on an elliptical bike to raise awareness about addiction stigma.
[43:10] – Clay’s global adventure: how traveling to 20 countries opened his eyes to the shared humanity across cultures.
[56:23] – The metaphor of the Great Barrier Reef: how diversity and unity coexist harmoniously in nature and in life.
[1:05:34] – Reflections on the power of the journey versus the destination.

Links & Resources:

Closing Remarks:

If you enjoyed this episode, don’t forget to rate, follow, and share it with others who might be inspired by Clay’s story. Your support helps spread these powerful messages. See you next time as we continue to explore life’s greatest adventures!

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What Does Financial Independence Mean to You?

According to a recent poll of 2,000 U.S. adults, “financial independence” equates to earning $94,000 per year, or about $20,000 more than the median income in 2023.

Some folks might feel like they’re just a promotion or two away from achieving that kind of independence. Others might not feel like $94,000 isn’t enough to feel truly free. And still others might wonder how they’d ever spend that much money in the first place.

 That’s because true financial independence isn’t a number. So if it’s not a number, then what is financial independence?   

It’s feeling confident enough in your money to do things that will improve return on your life (ROL), such as:

1. Spend without worrying

In our experience, it’s true that money can’t buy happiness. But it’s also true that being able to treat yourself and your family without worrying about paying your credit card bill at the end of the month is a pretty great feeling as well.

No matter how much you’re earning, setting a monthly spending budget can help you cover your necessities, contributes to your retirement goals, and have a little fun along the way. A budget can also help you plan ahead for responsible “big ticket” splurges, like a dream vacation or adding a pool to the backyard.

2. Enrich your children

Unless your kids love spending a lot of time at the local library, enrichment isn’t free. According to Lending Tree, parents spent an average of $731 per child per year on extracurriculars. You might spend thousands of dollars every year on a good athlete or ballerina through their teenage years … which is when the bills really start rolling in. The average cost of a year of college for the 2023-24 school year is $10,662 at an in-state public school, and $42,162 at a private school. This is for tuition ONLY…room and board will be in addition, and if you haven’t noticed, rent cost is much higher now than it used to be!

Parents might not feel truly free until they’ve passed that big COLLEGE goal until the last payment has been made. But with that goal in sight, we can help you start planning a combination of savings and investments that will reduce some of the sticker shock when the time comes. And by including some of your children’s activities in your budgeting and long-term plans, you might be able to sign them up for a few extra classes that round out their development or allow them to dig more deeply into their passions.

3. Change careers

Once upon a time, your high school guidance counselor might have challenged you to imagine what you’d do for a job if you didn’t need money. Setting aside your teenage dreams of being a rock singer or astronaut, do you have the means to make that switch right now?

Well, if money isn’t stopping you, then what is?  Is it time to re-train and re-tool for Career 2.0 or 3.0?

Taking a lower-paying job at a company or charitable organization that does work you admire could give you an opportunity to put your professional skills to their highest uses. Rather than trying to climb a ladder or earn a bigger paycheck, you can focus on the mission at hand and the people and causes you’ll be impacting.

4. Retire

Or maybe you’re feeling independent enough to stop working all together.

Folks who plan their retirement around hitting some arbitrary financial number often put off retirement longer than they need to. Remember, financial independence isn’t a number. 

Seeing how your plan can make your retirement possible while also providing for long-term goals like vacationing or relocating could give you the security you need to feel financially independent. Want to discuss this further?  Reach out to me and let’s start planning to earn more ROL and more freedom from your money.

Episode 25: From the Shadows to the Spotlight with Joe Gray


In this episode of the On Adventure Podcast, I sit down with Joe Gray, an exceptional athlete who turned challenges into triumphs. Joe shares his journey from growing up in Nashville, Tennessee, and attending the Tennessee School for the Blind to becoming a world-class athlete. With the support of dedicated mentors and his unwavering determination, Joe excelled in wrestling and track and field, eventually competing at the Paralympics. His story is a powerful testament to resilience, mentorship, and the pursuit of dreams.

Timeline Summary:

  • [00:00] – Introduction to Joe Gray and his inspiring journey.
  • [00:01] – Joe’s early life in Nashville and attending the Tennessee School for the Blind.
  • [00:04] – Coping with visual impairment and developing an adventurous spirit.
  • [00:10] – Transition to high school sports and excelling in wrestling and track.
  • [00:16] – Competing in the Youth World Championships and facing international competition.
  • [00:25] – Setting a world record in the 4x100m relay and the realization of his potential.
  • [00:32] – Challenges of training and maintaining top performance while seeking sponsorships.
  • [00:39] – Transitioning from athlete to coach and starting Sight School with Lex Gillette.
  • [00:52] – Organizing ski trips for visually impaired students and the impact on their lives.

Links & Resources:

Closing Remark:

If you enjoyed this episode, please rate, follow, and review the On Adventure Podcast. Share it with friends and family who might find Joe’s story as inspiring as we did. Join us next time for more incredible journeys and motivational tales!

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Episode 24: Stories Rather Than Regrets with Pete Ripmaster


Welcome back to the On Adventure podcast! In today’s episode, we have an inspiring and candid conversation with Pete Ripmaster. Pete, now a seasoned ultra-endurance athlete, shares his journey from the highs and lows of his athletic pursuits to his personal battles and triumphs. In fact, it all started with a Couch-to-Marathon run, and he kept going from there!  We delve into his history, including the incredible feat of winning the 1,000-mile Iditarod Trail Invitational on foot (in February!), his adventures in Alaska, and the lessons learned from pushing beyond the limits. Pete’s story is a testament to resilience, passion, and the relentless pursuit of one’s dreams.

Pete’s philosophy of “stories rather than regrets” is evident in his approach to ultra-running. Whether he’s tackling organized races or his unique “homemade 100’s,” Pete’s willingness to suffer and push through mental and physical barriers is key to his success. His adventures showcase the power of perseverance and the rewards of stepping outside your comfort zone.

Join us as we explore:

  • Pete’s early life and the pivotal moments that shaped his path
  • The transition from the couch to a marathoner to an ultra-endurance runner
  • The mental and physical challenges of running the Iditarod Trail Invitational
  • Pete’s “homemade 100’s” and what drives him to create his own ultra-endurance challenges
  • Insights into the world of ultra-running and the community around it
  • Pete’s future aspirations and what drives him to keep pushing forward

This episode is packed with raw and heartfelt reflections that will leave you inspired to tackle your own adventures. Don’t miss out on this incredible journey with Pete Ripmaster!

Episode Highlights:

[00:00] Introduction to Pete Ripmaster and the essence of today’s episode

[02:28] Pete’s background and his self-identity as a runner, husband, and father

[10:00] Reflections on Pete’s childhood and the significant impact of his family

[18:00] The pivotal moment and the transition from a wild lifestyle to purposeful living

[24:05] Pete’s first impromptu marathon and the beginning of his running journey

[32:00] The decision to run 50 marathons in 50 states and raise funds for breast cancer research

[38:00] Delving into ultra-running: from 50K to 1,000 miles

[46:00] The challenges and triumphs of the Iditarod Trail Invitational

[53:00] Pete’s “homemade 100’s” and his drive to create unique endurance challenges

[57:00] The mental game in ultra-endurance sports and pushing through limits

[01:03:00] What’s next for Pete after ultra-running

Links & Resources:

Thank you for tuning into this episode with Pete Ripmaster! If you enjoyed our conversation, please rate, follow, share, and review the podcast. Your support helps us bring more inspiring stories to light. Keep pursuing your great adventures, and we’ll catch you in the next episode!

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Giving While Living

If charity is part of your legacy plan, the best time to start giving back could be right now. Spending on other people is one of the most rewarding ways we can use our money. And seeing your generosity in action might give you some ideas on how to improve your legacy planning for your beneficiaries.

Here are three ways you can kickstart your legacy plan and take a more active role in your long-term charitable goals.

Solve a local problem.

The issues in the world are so great right now that many smaller concerns can slip through the cracks. Somewhere in your community right now there is a park in disrepair, a vital organization or program that’s hurting for funds, or a group of people whose needs aren’t being met. You could coordinate with other concerned citizens and local leaders on an action plan or start your own charitable organization that’s focused on filling that void. If your initial efforts fall short, or if solving one problem reveals more issues, you can recalibrate your plans — and your giving strategy — in the service of more permanent solutions. Being a force for positive change in your community might even inspire similar acts of charity and kindness among your neighbors.

Donate your time.

Charities depend on passionate people almost as much as they depend on donations. Whatever your professional background may be, it’s likely that there’s a cause that can benefit from your skills and knowledge during a few weekly volunteer shifts. If you’re also donating to a place where you volunteer, you’ll gain a “behind-the-scenes” perspective on how your money is being spent, and perhaps on ways that the organization could be using its resources more effectively. And if you’re still working full time, volunteering can also be a great glide path during your transition into retirement. As your career begins winding down, you can use your charitable goals to create a new retirement schedule that will keep you active and engaged.

Empower your loved ones.

Depending on the laws in your place of residence and what your giving goals look like, there are many options for distributing your wealth to your heirs. You might consider outright gifts, such as helping with the downpayment on a house or car. If grandchildren are on the way, you might open savings or investment accounts in their names. If you’re considering leaving behind a sizable amount of money to an adult relative, gift them a smaller amount and see how responsibly they manage their “pre-inheritance.” Perhaps your generosity will open up opportunities for you to pass on some of your wisdom around gaining, managing, and growing wealth. Or, you might decide that rather than leaving money to loved ones directly, a family trust might be a more efficient way to preserve your wishes.

You could also establish a family charitable organization and start involving your heirs in its management. Have a family conversation about the causes that are nearest to your heart and how you can use your family’s resources to make a lasting impact. More than just leaving money to your loved ones, you’ll also be leaving them with a real sense of purpose and a deeper understanding of what was really important to you.

Charitable giving of any kind will raise some important financial planning issues, starting with the tax ramifications for you, your estate, and your beneficiaries. Establishing trusts or family charities will require even more complex planning. We can help you clarify your charitable goals so that we can work together on the best strategies for preserving your legacy.