On Adventure: What We Carry

Lessons from Gil Jackson and Aaron Saft

Every long walk is an exercise in deciding what matters enough to carry. Ounces add up over thousands of miles, and eventually you strip down to what is essential. In our two most recent On Adventure episodes, I sat down with a Cherokee language educator and an ultrarunning coach whose lives revolve around a version of that same question: out of everything you could hold onto, what is worth the weight?

Gil: Walking Home

Gil Jackson grew up in the Snowbird community of western North Carolina in the 1950s – no television, no car, one light bulb per room, and a tight-knit Cherokee community where everyone showed up when a neighbor needed help. When he left for college in Georgia, his mother laughed and said, “You’ll be back.” He was gone almost 40 years, then built a house 200 yards upstream from where he was born and poured himself into the work that now defines his days: keeping the Cherokee language alive.

Only about 130 fluent speakers remain, and they are losing roughly two and a half a month. Gil calls it the eleventh hour. He thru-hiked the Appalachian Trail in 2014 to experience some portion of what his ancestors endured on the Trail of Tears, and conceded the biggest difference: he got to come home. But what moved me most is what Gil does off the trail. He spends his days locating sacred Cherokee sites in the mountains and taking younger people to them, so the stories and routes are not lost. The elders who know where these places are can no longer reach them. The young people who can make the climb do not know they exist. Gil is the bridge.

Aaron: What Do You Need?

Aaron Saft has finished Hardrock, UTMB, Leadville, Western States, and the Bigfoot 200. But the moment from our conversation that will stay with me had nothing to do with a finish line. It was his description of what happens when you come across another runner sitting on a rock in the middle of a 100-miler. You do not ask, “How are you?” You can see how they are. You ask, “What do you need?” And then you give whatever you have. Aaron said it is not a decision people make in the moment. It is who the sport turns you into.

He pins an upside-down photo of his family to his quad so that when he looks down at mile 80, he sees his wife and kids looking back at him. His son now runs for the University of Portland. His daughter, a high school freshman, just competed at the state championships. When other parents ask how he got his kids into running, his answer is simple: he did not. He just showed them what was possible. He even rebranded his coaching business – from “MR Running Pains” to “Running is Life” – because the words we wrap around our work shape the experience. Training is 99 percent process and 1 percent celebration. If you cannot find joy in the process, you are missing the whole thing.

The Same Trail

Gil is preserving a language and the sacred geography of his people. Aaron is building runners who understand not just what to do but why. Both told me the point was never the miles. The miles were just the means of discovering what mattered enough to hold onto. Not every adventure happens on a trail. Some happen when you ask someone what they need and mean it, or when you pass along something that would disappear if you kept it to yourself.

Stay safe and stay on adventure.

— Josh

You can listen to the full conversations with Gil Jackson and Aaron Saft on the On Adventure podcast, available wherever you get your podcasts.

Q3 Letter to Clients

The Economic Landscape

If Q1 felt like driving into a headwind, Q2 was the stretch of open road that followed. Markets staged a powerful recovery, more than erasing the losses that rattled investors earlier in the year. For the quarter, the S&P 500 gained roughly 14.5%, the Nasdaq Composite surged approximately 19.7%, and the Dow advanced around 11%. Small-cap stocks were the quiet standout: the Russell 2000 returned approximately 20.8%, capping its strongest first half since 1991.

Importantly, the rally was not built on hype alone. S&P 500 companies reported first-quarter earnings growth of about 28% on revenue growth of nearly 12%, and market leadership broadened meaningfully, with Consumer Staples, Real Estate, and Healthcare joining the conversation by late June. Inflation, however, remains elevated. The Consumer Price Index hit 4.2% on an annual basis in May – its highest since April 2023 – driven largely by energy costs. Core CPI, which strips out food and energy, was more encouraging at just 0.2% for the month, suggesting the broader pass-through from the energy shock is still limited.

Making Sense of the Headlines

The conflict between the U.S., Israel, and Iran has been the dominant macro story of 2026, disrupting roughly one-fifth of the global oil trade and pushing average gasoline prices as high as $4.56 per gallon in May. By mid-June the picture shifted: the U.S. and Iran signed a memorandum of understanding on June 17 to extend the ceasefire and begin reopening the Strait of Hormuz, sending crude oil down roughly 20% from its 2026 peaks. That is real progress, though the situation remains fluid and a permanent deal is still being negotiated.

On the monetary policy front, the Federal Reserve held interest rates steady at 3.50%–3.75% at its June meeting – the fourth consecutive hold and the first under new Chair Kevin Warsh. The updated dot plot told the bigger story: half the committee now envisions at least one rate hike before year-end, a sharp reversal from March projections that still implied a cut. The Fed also raised its 2026 inflation forecast to 3.6%, up from 2.7% just three months earlier. The message is clear: the central bank is not in a hurry to ease.

Staying the Course in a Noisy World

Wars, inflation, and Federal Reserve posturing are not comfortable topics. We know the headlines can feel heavy. But if the first half of 2026 has reinforced anything, it is that markets reward patience more than prediction.

In late March, after the worst of the oil-shock selloff, the S&P 500 had pulled back to around 6,344 – roughly 7% below where it began the year. Investors who stepped to the sidelines would have missed one of the sharpest quarterly recoveries in recent memory. Those who stayed invested, rebalanced, and leaned into the discomfort were rewarded with a double-digit rebound in a matter of weeks.

This is not a new lesson, but it is one worth revisiting in every market cycle. Volatility is not risk. Volatility is the price of admission to long-term compounding. Risk is permanently impairing your capital by abandoning your plan at the wrong time. We continue to believe that a disciplined, diversified approach – across asset classes, market capitalizations, and geographies – is the most reliable way to build and protect wealth over time.

Protecting What You Have Built

So much of our work together focuses on growing and investing your wealth. But the plans we build only work if the foundation underneath them is solid – and that brings us to a topic that does not get enough attention: your insurance coverage.

Summer is a natural time to review your property, auto, and umbrella policies. Home values, replacement costs, and liability exposures can shift meaningfully from year to year, and your coverage should reflect the life you are living today, not the life you were living when you last renewed. If you have not looked at your policies recently – or if you have questions about whether your umbrella coverage is adequate given changes to your net worth, real estate, or vehicle situation – we would love to help. Just reach out and we will walk through it together.

As always, we are grateful for the trust you place in our team. Half the year is in the books. There will be more headlines, more volatility, and more reasons to worry between now and December. But there will also be more reasons to be thankful – for the progress we have made together, for the plans we have built, and for the lives those plans are designed to support. We hope your summer is full of rest, adventure, and time with the people who matter most.

Stewarding Significant Wealth: Navigating Complex Financial Decisions

At a certain point, the financial conversation shifts.

For most people, the early stages of building wealth are focused on accumulation. Growing a business, investing consistently, and creating a sense of security. But when wealth reaches a level of real significance, the questions change. It becomes less about whether you have enough and more about what you do with it, how you protect it, and whether it continues to reflect what actually matters to you.

That is the work of stewardship. And it looks very different from standard financial planning.

The complexity is real

Ultra-high-net-worth families face a different set of decisions than most financial plans are built to address. A portfolio may span public investments, real estate, private companies, philanthropic structures, and multigenerational planning. Each layer adds another decision point. Taxes matter more. The structure of asset holdings matters more. Family dynamics matter more.

And here is something that surprises many people: the margin for costly mistakes does not shrink just because there is more money on paper. In some ways, it grows. Complex wealth requires more coordination, more intentionality, and a plan that is built around your specific situation, not a template.

Tax planning is not an afterthought

For families managing significant wealth, tax planning is often where the most valuable work happens. Not because every decision should be made to save taxes, but because the tax consequences of major decisions deserve to be considered before they are made, not after.

The most effective planning weaves together investment strategy, estate considerations, charitable giving, and liquidity needs. When those pieces are coordinated, families can be much more deliberate about timing, ownership structures, and how different assets fit into the larger picture.

Beyond a traditional portfolio

Many families at this level begin exploring opportunities outside of a standard investment portfolio. Real estate, private companies, alternative investments, and family-office-style structures can all offer meaningful diversification and long-term potential. But they also entail greater complexity, more due diligence, and a need for clarity about how each piece fits the overall plan.

The question worth asking is not just “What is the return on this?” It’s “How does this serve the life and legacy we are building?”

Using wealth well, right now

One of the most common patterns we see is this: families who have worked hard to build significant wealth end up waiting too long to use that wealth intentionally. There is always a reason to hold off. Another milestone to hit. Another uncertainty to resolve first.

But wealth is most powerful when it is engaged with intention now. That might mean funding the experiences that matter most to your family. Supporting causes that align with your values. Helping the next generation understand both the opportunity and the responsibility that comes with what they will inherit. Sometimes it simply means giving yourself permission to live fully into the life your planning has made possible.

Good stewardship is not about being cautious to the point of paralysis. It is about making decisions that are values-aligned, tax-aware, and built to last, while also actually living.

The real work

At the highest levels of wealth, financial planning is not primarily about performance. It is about making sure the decisions you make today reflect who you are and what you want your wealth to do.

That requires a plan that accounts for complexity, a team that understands the landscape, and the clarity to know what you are building toward. Not just financially, but in life.

Wealth creates opportunity, but it also creates responsibility. If your financial picture has grown more complex and your planning has not kept pace, it may be time to revisit whether your strategy truly reflects the life you’re building. Reach out to our team to start the conversation.

Base Camp Thinking: What Mountaineers Know About Volatile Conditions

There’s a sentence Ed Viesturs likes to repeat, and we’ve been thinking about it a lot lately.

“Getting to the top is optional. Getting down is mandatory.”

Viesturs is one of the most accomplished high-altitude mountaineers in history – one of a handful of climbers to summit all fourteen of the world’s 8,000-meter peaks without supplemental oxygen. He’s said he didn’t make it home that many times by being brave at the wrong moments. He made it home by being disciplined at the right ones.

Markets aren’t mountains. But the principles people use to come home alive from volatile conditions translate surprisingly well to financial life planning. And in a stretch like this one – energy shocks, persistent inflation, consumer confidence at all-time lows – we keep returning to a few of those principles.

Base camp

No one summits straight from the road. The first thing you do is build a base camp – a stable, well-supplied position you can return to when conditions deteriorate. You sleep there. You eat there. You wait out storms there.

In a financial life, base camp is the cash reserve. It isn’t where you live – it’s what you fall back on when the weather turns. And the function it serves isn’t really about the dollar amount. It’s about giving you the freedom not to make decisions out of panic.

Households with an honest base camp don’t necessarily make different long-term decisions than households without one. But the experience of difficult conditions is fundamentally different. One is decision-making from a position of strength. The other is decision-making from a position of fear.

Acclimatize before you climb

Altitude doesn’t care how strong you are at sea level. The body has to be allowed to adapt to thinner air, in stages.

Building a financial life has a similar rhythm. Big decisions – a new house, a business move, an early retirement, a significant inheritance – work best when there’s time to acclimatize. To live with the implications. To stress-test how they feel. To see what assumptions hold and which don’t.

Most of the financial regrets we hear about aren’t bad ideas. They’re good ideas executed too quickly.

Pre-set turnaround thresholds

Climbers set turnaround times before they start the summit push. If you haven’t reached the summit by, say, 2 p.m., you turn around. Period. The decision is made in advance – in calm conditions, with clear thinking – precisely because at altitude, in bad weather, under pressure, the mind isn’t reliable.

A financial plan with pre-set thresholds works the same way. Rebalancing triggers. Cash buffer minimums. Withdrawal rate guardrails. Spending floors during retirement transitions. These aren’t constraints – they’re decisions made when your head was clear, so you don’t have to make them when your head isn’t.

The team you bring

No one solos K2 by accident. Every expedition has a team – sherpas, climbers with complementary skills, an extended network at lower altitudes. The team is part of the equipment.

In a financial life, the team is the people you’ve intentionally chosen to walk alongside you – the spouse you talk through decisions with, the CPA, the estate attorney, the advisor, the family members you trust. The point isn’t to outsource judgment. It’s to have other clear minds in the room when yours is tired.

One more thing

The mountains have a way of revealing what was already true. Volatile financial conditions do the same.

If your plan is built well, hard stretches are uncomfortable but not catastrophic. If it isn’t, hard stretches reveal what was missing – and they tend to do it at the worst possible moment.

We’d rather have those conversations now, in calm air, than at the top of the ridge.

When the Tank Costs More: Energy, Inflation and the Family Budget

Walk into almost any conversation with friends right now and the cost of things is bound to come up. The grocery bill. The fuel cost. The summer travel that suddenly feels more expensive than it did last year.

We want to make sense of what’s actually happening – without spin and without panic – and offer a calm way to think about the household budget through this stretch.

Where the pressure is coming from

A few things are converging.

Gas prices are up sharply. The U.S. national average for a gallon of regular sits around $4.48 in late May, an increase of nearly 50% since February. The driver is largely geopolitical – disruption to oil supply routes through the Strait of Hormuz, which historically handles roughly a fifth of the world’s seaborne oil.

Headline inflation is moderate but persistent. The Consumer Price Index for April came in at 3.8% year-over-year, up from 3.3% the month before. That doesn’t feel huge until you remember it’s stacked on top of several years of similar increases.

The cumulative effect is real. A common framing – a basket of goods that cost $100 before the pandemic now runs about $126. That’s where the “everything is more expensive” feeling comes from. It’s not your imagination.

Why oil ripples beyond the pump

Higher oil prices don’t only show up when you fill the tank – they show up indirectly in almost everything you buy. Nearly every product spends time on a truck. Shipping costs feed into grocery prices, into building materials, into the cost of a hotel room two states over. The pump price is the most visible piece of a broader effect.

That’s why the budget pressure right now isn’t only about gas. It’s about gas plus the things that gas touches.

The line we’d encourage you to draw

There’s a simple distinction worth making, and we find that families do better when they make it explicitly.

Essential – the things that have to be paid no matter what. Housing, utilities, basic food, insurance, transportation to work, medical.

Discretionary – everything else. Some of it is meaningful to you. Some of it has crept in through habit.

Both categories deserve respect. We’re not in the camp that says cut every latte. Discretionary spending is often where life happens. But knowing which line items are which gives you choices, and choices are what reduce anxiety in a stretch like this one.

Sticky vs. temporary

A second cut worth making – which price increases are temporary, and which are likely to stay with us for a while?

Gasoline is sticky in the sense that it stays elevated until the underlying supply story changes. We don’t know how long that takes.

Some household items are temporary – they spike for a season and ease back.

Some are structural. Housing, healthcare, insurance – these tend to grind higher over time regardless of headlines. They’re the line items that quietly do the most damage to a long-term budget, because they don’t make the news.

For most families, the leverage is in the structural line items. A modest, deliberate review of housing-related expenses, insurance, and recurring services often produces more breathing room than cutting variable costs.

A few starting places

Not advice for your specific situation – just a frame.

Re-price what you can. Insurance, internet, streaming, subscriptions – these are line items most households don’t revisit annually, and there’s often room.

Refresh the emergency cash number. The familiar “three to six months of essential expenses” rule still holds, but the dollar figure has moved. Your reserve from 2022 may now cover less ground than you think.

Be honest about discretionary creep – not to shame it, to see it. Choices are easier when you know what you’re choosing.

If you’d like to walk through any of this in the context of your own situation, that’s what we do. The numbers feel less heavy when there’s a structure around them.

“Will We Be Okay?” The Question Beneath the Question

Of all the questions we’ve heard in this work over the years, the one that’s been coming up most often lately isn’t really a question – it’s a feeling. The words around it shift depending on who’s asking and what kind of week they’ve had.

“Will we be okay?”

Sometimes it sounds like a market question. Is the portfolio set up for this? Sometimes it sounds like a household question. If we have to absorb a few more shocks, how do we look? Most of the time, when we listen carefully, it’s neither. It’s a question about whether the plan can hold.

We want to talk about that question – because it deserves a real answer, not a market forecast.

What clients are really asking

When we sit with someone who’s worried, the surface question is almost never the deepest one. The surface might be should we cut back on travel this summer? The deeper question is does our life still have room in it for the things that matter to us, if conditions keep getting harder?

That’s not a market question. That’s a planning question. And it has a real answer.

Resilience isn’t a guess

A financial plan, built well, doesn’t depend on the next twelve months going a particular way. It’s designed to absorb the months we can’t predict. That’s the whole point.

The pieces that actually answer the “will we be okay” question aren’t headlines – they’re structural. A cash reserve sized to your real fixed expenses, not the version of your budget on a calm day. A clear picture of which expenses are truly fixed and which feel fixed because they’re habits. An understanding of which goals are non-negotiable and which are timing-flexible. A goal that can wait six or twelve months without doing damage is fundamentally different from one that can’t. And a relationship between your portfolio and your actual time horizons – money you need soon shouldn’t be at the mercy of money you don’t need for fifteen years.

When those pieces are in place, the answer to “will we be okay” is mostly already written. It’s not a prediction. It’s a structure.

What we’d say if you asked us today

We’d say what we always say – it depends on the plan you’ve already built, and we can walk through it together. We’d look at your fixed-expense floor. We’d look at where your goals have room to flex. We’d look at the cash reserve relative to today’s prices, not last year’s. And we’d revisit time horizons.

That conversation is rarely as scary as the one in your head.

A small word on the headlines

Consumer sentiment hit an all-time low in May – lower than during the 1970s oil crisis, lower than 2008, lower than the early days of the pandemic. That’s a fact worth knowing, mostly because it means two things at once. If you’re feeling unsettled, you’re not imagining things, and you’re not alone. And feelings are not forecasts. The economy will do what it does. Your plan can be ready for a wider range of outcomes than you might think.

If “will we be okay” has been a question on your mind, we’d love to sit with it. That’s what we’re here for.

Your Photos Are Part of Your Legacy – But Is Your Family Prepared?

Guest post by Teresa Cox: Simple ways to organize, preserve, and share your family’s memories – now and for the next generation

When most people think about leaving a legacy, they focus on financial assets – investments, property, estate plans.
But in my experience, families often aren’t prepared to pass on the most meaningful
assets: the photos, the stories, the family traditions, and the moments that capture a life
over time.
Today, photos are everywhere – on phones, computers, external drives, and across
multiple websites or cloud services. At the same time, many families have decades of older
memories – photo albums, printed photos, slides, and home videos – tucked away in closets
or attics, slowly deteriorating or becoming harder to access.
There’s rarely a single place where everything lives. And often, no one else knows how to
access it – or has a clear plan for how those memories will be organized, preserved, and
shared.

Most of the families I work with aren’t in crisis.

They’re simply at a stage of life where they’re starting to think more intentionally about the future – especially parents who have spent years documenting their children’s lives and want to make sure those memories are organized, protected, and easily shareable with the next generation.

3 Simple Ways to Begin Preserving Your Family’s Memories

1. Bring Your Photos Together

Over time, photos tend to get scattered across devices, platforms, and accounts.

It’s very common to have photos on your phone, older computers or hard drives, in cloud services like iCloud or Google Photos, and in printed albums or storage boxes.

Rather than leaving everything spread out, begin thinking about how to gradually bring your photos together into fewer, more centralized locations.

If your printed photos and older media are stored in multiple places around your home, consider consolidating them into one general area.

Labeling boxes can also be incredibly helpful – especially with timeframes like years or decades, if known. Even simple labels make it much easier to navigate your collection.

If you happen to know family connections for older or heritage photos – like which side of the family they came from or who is pictured – that information can be incredibly meaningful to future generations. It doesn’t have to be perfect – just capturing what you know is often more than enough.

2. Make Your Photos Accessible

Once your photos are more centralized, the next step is making sure they can be accessed when needed.

For digital photos, this may involve sharing passwords or using built-in legacy settings for your online accounts.

If you use an iPhone, Apple offers a Legacy Contact feature.
If you use Google services (Android), there’s a similar tool called Inactive Account Manager.

Accessibility also means that someone else could step in and understand what you have. Even simple organization and clear labeling can make a big difference.

Most people don’t realize how difficult it can be for someone else to piece all of this together without guidance – but a little bit of planning now can make things much easier later.

3. Share and Preserve What Matters Most

Once your photos are more organized and accessible, the next step is to begin sharing them intentionally.

This doesn’t have to be complicated or time-consuming. In fact, some of the most meaningful moments come from simply pulling out old photos or home videos and enjoying them with your children or grandchildren.

Many families have older memories – slides, printed photos, and home movies – that haven’t been viewed in years. Digitizing these items not only preserves them, but makes it possible to easily watch, share, and enjoy them again.

There’s something incredibly special about seeing old family videos come to life – hearing voices, watching personalities, and experiencing moments that might otherwise be forgotten.

You might also consider creating something simple but meaningful, like a small photo book that tells the story of your life or your family. It doesn’t require hundreds of photos – just a thoughtful collection that captures the moments and people who matter most.

The goal isn’t perfection. It’s making sure your memories can be experienced, shared, and enjoyed – both now and for years to come.

If this is something you’ve been meaning to get to “someday,” consider this your gentle nudge to take a small first step – whether that’s gathering your photos into one place, labeling a few boxes, or sharing a favorite memory with your family.

Many people don’t realize there are professionals who specialize in organizing and preserving photo collections – this is the kind of work I help families with every day. 

If you’d like guidance or support along the way – even just a starting point – I’m always happy to help.

Teresa Cox
Photo Concierge Services

photoconciergeservices.com

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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Episode 18: Into the Wild with Tim Matthews


In today’s episode, we embark on a deeply personal journey with Tim Matthews, a seasoned adventurer and outdoor enthusiast who just happens to be a retired Navy one-star Admiral. In this conversation, Tim shares his profound insights and experience, both personal and professional, offering a glimpse into the transformative power of outdoor pursuits in shaping his life. From heart-pounding rock climbing expeditions to soul-soothing solo backpacking trips, Tim reveals how each adventure has left an indelible mark on his spirit.  I find this incredibly inspiring.

As we navigate the conversation, you will hear how Tim has learned more about himself amidst the awe-inspiring beauty of nature. From the exhilaration of summiting towering peaks to the quiet contemplation of remote wilderness trails, Tim shares his lessons learned and the deep connections forged with the natural world.

Ultimately, through detailing his outdoor experiences, Tim uncovers the threads that weave together resilience, growth, and the unyielding spirit of adventure. I am certain that you will be encouraged to embrace your own call to the wild, which is an awesome call. 

Enjoy my conversation with Tim Matthews.

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Paying twice with Thom Asta


It is a treat to be surprised to learn something amazing and interesting about someone you have known for a long time.  My hour or so conversation with Thom Asta fits this description perfectly.  I have known Thom for going on 20 years but the things we discussed blew me away and gave me a new level of respect for a man that I had a ton for already. 

This podcast is about how and why the Everyday Explorer continues to find, and then expand, his or her limits.  But it is not just about the adrenaline story.  I want to know what they learn through the challenge of adventure, and how it changes them moving forward.  Thom points out that sometimes this exploration is intentional, but sometimes it is not.  And these surprise challenges usually are the most difficult, most dangerous and full of ‘gold’ if one should make it through. 

Be sure to stick with this to the end as his story reaches a peak event that he never saw coming, and the gratitude and vibrancy for life that was the gift he received on the other side.  I was on the edge of my seat and left searching for words by the end.  I know you are going to love Thom Asta!

Check out this episode!