The Turnaround Decision

Summit fever has a financial cousin – and the cure is the same in both places. Decide what would make you turn around before you’re standing there.

There’s a phrase climbers use for the thing that gets people killed, and it isn’t weather or altitude or bad rope work. It’s summit fever – the pull that takes hold when the top is close and every reason to keep going suddenly sounds more convincing than it did at breakfast.

Stefan Gruber described it well in a recent On Adventure conversation. He’s turned back from the Grand Teton twice. What stayed with us wasn’t the turning around; it was how he thought about the times things worked out anyway. There’s a certain store of luck, he said, and it runs out eventually. Surviving a bad decision doesn’t make it a good one.

We’ve thought about that line a lot, because we watch a version of it play out at desks and kitchen tables all the time.

The Financial Version

Summit fever in a financial life doesn’t look dramatic. It looks like reasonableness, which is exactly what makes it hard to catch.

It’s the concentrated stock position that has done so well that selling any of it now feels like quitting early. It’s the business someone meant to step back from three years ago, still going, because this year is finally the year it all pays off. It’s the rental property that stopped making sense a while ago but has become part of how a person describes themselves. It’s the goal set at forty-five that nobody has re-examined at sixty, still quietly driving decisions.

In every case the pattern is identical. The commitment was sound when it was made. Conditions changed. And the reasons to keep going are being generated by the part of us that has already decided.

That’s the tell. When we notice ourselves reaching past the original reasons for new ones, something has usually shifted.

Why It’s Hard in the Moment

Standing a few hundred feet below a summit is the single worst place to evaluate whether you should be there.

You’re tired. You’ve spent real money and real time. Everyone around you has too. The thing you came for is right there, and the effort already sunk feels like an argument for continuing rather than what it actually is – gone either way, and irrelevant to the decision in front of you.

Financial decisions inherit all of it. Add in the fact that turning around usually means admitting the plan changed, which people hear as admitting the plan was wrong. It wasn’t. Conditions changed. Those aren’t the same thing, and conflating them is what keeps people on routes they’d never choose fresh.

Then there’s the quiet distortion Stefan named: if the last three times you pushed through it worked out, the lesson you absorb is pushing through works. The sample is too small and the stakes are too asymmetric for that to be a lesson at all.

Set the Criteria Before You’re Tired

Here’s the part climbers actually do, and the part most of us skip.

Serious parties set a turnaround time before they leave camp. Not a feeling – a time. If you aren’t at the summit by then, you go down, whatever the weather is doing and however good your legs feel. The whole point is that the decision gets made by the version of you that’s rested, unhurried, and not staring at the top.

The financial equivalent is the same move. Decide in advance what would change your mind, write it down, and let the calm version of yourself bind the tired one.

That might sound like:

  • “If this position passes a set share of our investable assets, we trim on a schedule – regardless of how it’s performing or what we think happens next.”
  • The business. “If I’m still working past a certain date, or if these specific conditions are met, we run a real conversation about transition – not a mental note, a meeting on the calendar.”
  • A property or venture. “If it hasn’t cleared this bar by this date, we sell. Not because it failed, but because that’s what we said.”
  • The plan itself. “We revisit the assumptions every year on a set date, including the ones we’re most attached to.”

The specifics belong to the family. The structure is what matters: a condition, a date, and an action, decided while nothing is on the line.

Turning Around Isn’t Failure

This is the piece worth saying plainly, because a lot of capable people carry the opposite belief.

Changing course is not the same as being wrong. Stefan will go back to the Grand Teton. The two attempts he walked away from didn’t cost him the mountain – they’re the reason he’s still available to climb it. Alex Potts, in another recent conversation, made the related point from the other direction: being fit enough to push harder isn’t the same as knowing whether you should. Experience is largely the accumulated ability to tell those apart.

The families we see handle change well aren’t the ones who never adjust. They’re the ones who built permission to adjust into the plan from the beginning, so that when the moment comes, it reads as judgment rather than defeat.

The summit will still be there. The point was never to reach it on this particular day. The point was to keep being someone who gets to go back.

If you’re carrying a decision like this right now – a position, a business, a goal you’ve outgrown but haven’t said so out loud – we’d be glad to sit down and think it through with you.

Ridgeline Wealth Advisors

This material is for general educational purposes and does not constitute investment, tax, or legal advice. It is not a recommendation of any particular strategy or security and does not account for any individual’s circumstances.

When the Market Feels Too High

What to do with the sense that this can’t keep going – and why the answer is usually a calendar, not a forecast.

We’ve been hearing a version of the same sentence in a lot of conversations lately. It comes out differently depending on the person, but underneath it’s always the same thing.

This feels too high. It can’t keep going up like this.

Nobody says it as a prediction. That’s the interesting part. It arrives as a feeling – a kind of low-grade unease that sits in the background of an otherwise good year. People aren’t asking us to confirm a thesis. They’re asking whether they’re the only one who feels it.

They aren’t. And we don’t think the feeling is irrational or something to be talked out of. But we do think it’s aimed at the wrong question.

The Feeling Is Real. The Question Underneath It Is Better.

When someone says the market feels too high, the literal question is about market levels. The real question, almost always, is closer to this: if something goes wrong, does it reach me?

That’s a much better question. It’s also an answerable one, which the first question isn’t.

Nobody knows where markets go from here. We don’t, and neither does anyone who tells you otherwise with confidence. What we do know – with a fair amount of precision – is what a given family needs to spend over the next several years, and where that money is currently sitting. That second thing is entirely within our control. The first never has been.

So when the unease shows up, we tend to stop talking about markets and start talking about a calendar.

Matching Money to When You Need It

There’s a way of thinking about portfolios that institutions have used for a long time, usually under a name that does it no favors – liability-driven investing. Pension plans use it because they have to. They know roughly what they owe and roughly when they owe it, so they build the portfolio around those obligations rather than around a benchmark.

Strip the jargon away and the idea is simple enough to explain on a napkin. Money you need soon shouldn’t be exposed to things that move a lot in the short run. Money you don’t need for a long time can be.

Families have obligations too. They just don’t call them that. Tuition in three years. The roof. The gap between retiring and turning on Social Security. A parent who may need help. A business that will need working capital before it needs anything else.

Once those are on a timeline, the portfolio starts to organize itself. The near-term needs get funded with cash and shorter-term bonds, where the point isn’t return – it’s certainty about the number and the date. The long-term needs get funded with assets that can grow, because they have the one thing growth assets require: time to recover from being wrong.

Everything in the middle gets sorted accordingly.

Why This Answers the Feeling

Here’s what changes when a plan is built this way.

A decline stops being an event that threatens the whole structure and becomes an event that affects one part of it – the part you weren’t going to touch for a decade anyway. You’re not selling into it, because the money for the next several years of living was never in there to begin with.

That’s the whole mechanism. It isn’t clever. It doesn’t require predicting anything. It just means that when markets do what markets periodically do, the household’s actual spending doesn’t depend on the timing.

Experienced parties in the mountains don’t manage risk by predicting the weather. They manage it by carrying enough food, fuel, and daylight that bad weather becomes an inconvenience instead of an emergency. The forecast is interesting. The margin is what gets you home.

How much margin is right depends entirely on the family – on what’s being spent, what else is coming in, how the rest of the picture is built, and honestly on how a given person is wired. Some people sleep fine with less. Some need more, and that’s a legitimate input rather than a weakness to be corrected. This is a conversation, not a formula.

What This Doesn’t Do

Two honest caveats, because we’d rather say them out loud.

This approach doesn’t make you more money when markets rise. Holding several years of spending in cash and short-term bonds has a cost, and the cost is opportunity – in strong years, that money would have done better elsewhere. What you’re buying isn’t return. It’s the ability to not be forced into a decision at the worst possible time.

And it doesn’t eliminate the feeling. You may still look at a statement and think this can’t last. You’ll just be looking at it from a position where the thought doesn’t require you to do anything about it.

That, in our experience, is most of what people are actually after. Not certainty about markets – nobody’s selling that – but the ability to hold an uncomfortable thought without it turning into an action you regret.

The Question We’d Ask Instead

If the feeling has been visiting you lately, try trading the question in.

Instead of is the market too high, ask: how many years of my actual life are already funded, no matter what happens next?

If you know that number and it sits comfortably against your timeline, the feeling loses most of its teeth. If you don’t know the number, that’s not a market problem – and it’s a much easier one to fix.

We’re always glad to walk through it. If you’d like to see what your own version of that number looks like, we’re here and happy to help.

Ridgeline Wealth Advisors

This material is for general educational purposes and does not constitute investment, tax, or legal advice. It is not a recommendation of any particular strategy or security, and it does not account for any individual’s circumstances. Allocation approaches involve risk, including possible loss of principal, and no approach guarantees a particular outcome.

Episode 77: The John Muir Trail, Leadership, and Running Toward Adventure with Alex Potts


What happens when you stop running away from the pressures of life and start running toward the life you actually want?

Alex Potts grew up in Sunnyvale, California, riding BMX bikes through the apricot orchards that would eventually become the heart of Silicon Valley. Raised by a single mom who taught elementary school and worked hard to keep their family afloat, Alex learned early lessons about money, service, resilience, and taking care of other people.

Those lessons followed him into a remarkable career.

Alex spent more than three decades helping build what became Loring Ward, a firm that helped pioneer the fee-based model used by independent financial advisors today. Along the way, he discovered that the most meaningful work wasn’t simply about accumulating assets. It was about helping people solve problems that actually mattered.

Then, while still in his 50s, Alex stepped away from the top job.

And that’s where another chapter of his story really began.

In this episode of On Adventure, Alex and I talk about business, family, friendship, endurance, and the pull of wild places. We explore why running became an outlet during one of the most stressful periods of his life, how the John Muir Trail helped reshape his relationship with adventure, and why some of his strongest friendships have been forged while doing difficult things outdoors.

We also get into a frightening day in the Grand Canyon when Alex—despite being in some of the best shape of his life—learned just how quickly an adventure can turn dangerous.

A mile and a half from the top, in extreme heat, his body started shutting down.

What helped turn things around?

A total stranger and a bag of beef jerky.

This conversation is ultimately about much more than hiking or business. It’s about service, wisdom, community, and getting busy living while you still have the opportunity.

In This Episode

We talk about:

  • From Silicon Valley to financial industry leadership — Alex’s upbringing in Sunnyvale, the influence of his parents, and his three-decade journey helping build Loring Ward.
  • Building a life around service — Why Alex believes great businesses, advisors, and leaders put helping people ahead of products, assets, or “wallet share.”
  • Running away vs. running toward — How running initially became an escape from the pressures of work and family before adventure evolved into something Alex intentionally pursued.
  • Adventure, friendship, and community — From the John Muir Trail and Mount Whitney to the Excellent Adventure group, Alex explains why difficult experiences shared with others create unusually strong friendships.
  • Knowing your limits—and having each other’s backs — What a dangerous Grand Canyon rim-to-rim hike taught Alex about preparation, humility, listening to his body, and the unexpected kindness of strangers.

Episode Timestamps

Episode Timestamps

00:00 – From Silicon Valley Roots to Loring Ward
Alex’s childhood in Sunnyvale, being raised by a single mom, and the unlikely path that led him into financial services and eventually to building Loring Ward.

08:00 – Building a Business Around Service, Not Sales
Why Alex rejected the traditional asset-gathering mentality and built a culture centered on genuinely helping advisors and their clients solve meaningful problems.

18:00 – Where the Drive to Help Others Comes From
Alex reflects on his mother, his father’s recovery from addiction, and how both shaped his belief in service, compassion, and taking care of people.

21:00 – The Day Running Changed His Life
Overwhelmed by a demanding career, young children, and little sleep, Alex started running—and discovered the value of exercise, solitude, and uninterrupted thinking.

24:00 – The John Muir Trail and Finding Sanctuary Outdoors
Backpacking through Yosemite and the Sierra Nevada, encountering ancient forests, and discovering the peace and perspective that come from extended time in wild places.

31:00 – Running Away vs. Running Toward Adventure
How Alex’s relationship with the outdoors evolved from a coping mechanism and escape into an intentional pursuit of adventure, challenge, and joy.

33:00 – Why the Best Adventures Are Shared
From Mount Whitney to the Excellent Adventure group, Alex and Josh explore friendship, companionship, and why doing hard things together creates such powerful bonds.

41:00 – Knowing When to Push—and When to Stop
Why fitness isn’t enough in the backcountry, how experience builds wisdom, and the importance of checking your ego when conditions or your body tell you something isn’t right.

43:00 – Grand Canyon Survival, Beef Jerky & Trail Magic
A rim-to-rim Grand Canyon hike in 110-degree heat goes sideways, a stranger’s bag of beef jerky helps Alex recover, and the experience becomes a powerful lesson in humility and having each other’s backs.

A Few Takeaways

Adventure can change from escape to pursuit.
At one point, running and the outdoors gave Alex a way to cope with stress. Eventually, something shifted. Instead of running away from something, he began running toward experiences he genuinely wanted.

Fitness and wisdom aren’t the same thing.
Being capable of pushing harder doesn’t always mean you should. Experience teaches us to recognize the signals our bodies—and sometimes our lives—are sending.

The best adventures are often about the people beside you.
The summit matters. The trail matters. But years later, it’s often the people who struggled, laughed, helped, and celebrated alongside us that we remember most.

Service is a way of being.
Whether you’re helping a client navigate a family crisis, staying at the back of a hiking group to make sure everyone gets home, or opening a door for someone at the grocery store, the principle is the same: I’ve got your back.

Resources & References Mentioned

  • John Muir Trail — The roughly 200+ mile Sierra Nevada trail Alex has backpacked in sections

  • Yosemite National Park — One of Alex’s favorite places on the planet

  • Pacific Crest Trail (PCT) — Alex discusses encountering thru-hikers while on the JMT

  • Henry Cowell Redwoods State Park — Near Alex’s home in the Santa Cruz Mountains and home to magnificent old-growth redwoods

  • Undaunted Courage by Stephen E. Ambrose — Alex’s recommended account of the Lewis and Clark expedition

  • Arthur Brooks — Referenced during the discussion of “deal friends” versus “real friends”

  • Dimensional Fund Advisors — An important part of Alex’s professional story and later his son’s career

Final Thought

One of the most memorable ideas in this conversation is also one of the simplest.

When you’re on a trail and someone is struggling, you help.

You don’t ask whether they’re part of your group. You don’t calculate what’s in it for you. You recognize that today it’s them—and tomorrow it could be you.

Alex has carried that philosophy from his childhood into business, from business onto the trail, and from the trail back into everyday life.

Maybe that’s part of what adventure is here to teach us.

Take care of the people around you. Know when to push and when to turn around. Find places where the voices go quiet. And don’t spend your whole life running away from something.

Find something worth running toward.

Keep the Adventure Going

If this conversation resonated with you, share it with someone you’d want beside you on the trail.

Subscribe to On Adventure wherever you listen to podcasts, and check out The Money Trail Guide for practical ideas to help you plan for adventure, minimize “trail waste” along the way, and use your resources to move toward the life that matters most to you.

Because someday isn’t the goal.

The adventure is happening now.

Check out this episode!

On Adventure: Lessons from the Edge

Two recent conversations from the On Adventure Podcast – and what they have to say about the lives the rest of us are building.

Every so often we like to step back from the individual episodes and notice the thread running between them. The two most recent conversations on the On Adventure Podcast came from very different places – a bike-shop classroom on the California coast and a rotating string of mountain towns out West – and yet they landed in almost exactly the same spot. Both are about choosing the harder, fuller life on purpose, rather than drifting toward comfort or putting it off for some vague day down the road.

That turns out to be a financial question as much as an adventuring one. So here are the two, and a bit of what stayed with us.

Episode 75: Hard Things Are Worth Doing with Justin Smith

Justin Smith teaches high school in Santa Cruz, where his classroom is a working bike shop – teenagers learning to fix bikes, build résumés, and solve real problems with their own hands. On his own time, he’s an ultra-endurance athlete who has ridden the 2,700-mile Tour Divide from Banff to the Mexican border in sixteen straight days, raced the Fiji Eco-Challenge, and lined up at the Ironman World Championships in Kona.

What we appreciated most was how ordinary he made all of it sound. Justin talks about the “pain cave” – the dark hours before sunrise on day two of a race, when the body starts asking what exactly you’re doing out here – not as something to conquer but as a room you learn to redecorate and settle into. Comfort, he says, is what gets sold to us. Hard things are what actually move the needle. The line he repeats to his students and his daughter has stuck with us: a ship is safe in its harbor, but that is not what ships were built for.

Listen to Episode 75 →

Episode 76: Do It While You Can with Stefan Gruber

Stefan Gruber grew up in Raleigh, studied engineering at Western Carolina, and today works a remote job for a technology company he’s been with for about six years. But the more interesting thing about Stefan is what the remote job makes possible. Where a lot of us build our lives around our work, Stefan has quietly done the reverse – he’s built his work around the life he actually wants to live.

For the last couple of years, that life has been a moving target, in the best sense. When his wife Sarah began travel nursing, the two of them packed a car and a trailer and started following her contracts – Bozeman, where they later got married in Glacier; Idaho; and now Colorado Springs, in the shadow of the Garden of the Gods. Almost everywhere they land, there’s climbing within twenty minutes of the front door. Stefan describes climbing the way Josh describes the trail: one of the rare activities where you’re so locked into the next move that everything else – work, stress, the noise – simply melts away. He’s an unusually good photographer, too, a habit that started when he found an old camera lens in his parents’ attic and went looking for the camera to match it.

He was refreshingly honest about the cost. Living on the move means no steady circle of friends – the hardest part, he admitted, of the whole adventure. But when Josh asked him to boil it all down to one lesson, Stefan didn’t hesitate: get out and do these things while you can. We only live once, we’re a little older every day, and the experiences, he said, end up meaning more than any car or house ever could.

That’s a sentence we think about a lot on the financial side of the desk. The only real value of money is in its use – spending it on what’s genuinely of value to you, whatever your version of that is. It’s easy to spend a whole career building bigger buckets for a someday that keeps receding, only to arrive less healthy, less able, or not at all. Stefan’s life is a working argument for the alternative: decide what matters, and go live some of it now.

Listen to Episode 76 →

What We Took From Both

Put the two side by side and the lesson from the edge is really one lesson. The worthwhile life rarely happens by default. It gets chosen – on purpose, against the pull of comfort, and without waiting for permission or for the perfect moment that never quite arrives.

That’s the heart of how we think about planning, too. A good plan isn’t about the number for its own sake. It’s about being able to do the hard, meaningful things on purpose, to stay present through the long stretches, and to spend a life – not just save for one. We’re grateful to guides like Justin and Stefan for the reminder.

If either of these resonate, they’re worth a full listen. And if you’d like to talk through what you want your own version of “do it while you can” to look like, we’re here and happy to help.

Ridgeline Wealth Advisors

Legacy Is Caught, Not Taught: Raising Kids Who Can Carry What You Build

There’s a line from a recent On Adventure conversation that we haven’t been able to shake. Talking about his own children, ultrarunner Aaron Saft said that legacy is something children catch rather than something we teach. He wasn’t talking about money – he was talking about the way his kids absorbed a love of the outdoors by watching, not by being lectured. But the more we sat with it, the more it felt like the truest thing anyone has said about passing on wealth.

Most families we work with have thought carefully about the mechanics of transferring assets – the wills, the trusts, the beneficiary designations. Far fewer have thought about the harder question underneath it: will the people who inherit this be ready to carry it? And that readiness, it turns out, is caught long before it’s ever formally taught.

The Quiet Curriculum

Children learn how money works in a household the same way they learn a first language – by immersion, years before anyone sits them down to explain it. They watch whether money is a source of tension or calm. They notice whether generosity is a habit or an afterthought. They pick up on whether work is something you resent or something you take pride in. By the time a family is ready to talk openly about the estate, the deeper lessons have usually already been absorbed, for better or worse.

This is good news and hard news at once. The good news is that you have far more influence than a single conversation could ever carry. The hard news is that you can’t outsource it to a document. A beautifully drafted trust can protect assets, but it cannot manufacture judgment, gratitude, or a sense of purpose in the person who receives them.

What Actually Gets Passed Down

When we ask families what they most hope to leave behind, almost no one leads with a dollar figure. They talk about work ethic. About generosity. About the sense that the family stands for something. The money is real and it matters – but it tends to be the vehicle, not the destination.

That reframing changes how a plan gets built. If the goal is simply to transfer the largest possible sum, the plan is an exercise in tax efficiency. If the goal is to transfer capacity – the values and the competence to steward what’s been built – then the plan has to include the people, not just the assets. That might mean bringing adult children into age-appropriate conversations earlier. It might mean letting them practice with real decisions while the stakes are still small. It might mean being honest about how the wealth was built, including the setbacks, so the next generation inherits the full story and not just the balance sheet.

Small, Repeated Signals

Because legacy is caught, the signals that matter most are usually small and repeated rather than grand and occasional. A family that gives together, even modestly, teaches generosity more effectively than a one-time gift ever could. A parent who talks openly about a financial mistake teaches resilience and honesty. A household where money is discussed calmly, without shame or secrecy, raises children who can do the same as adults.

None of this requires a fortune, and none of it happens on a deadline. It’s the accumulation of ordinary moments – the same way a hundred-mile race is really just one mile run a hundred times.

Where a Plan Fits

This is where the financial and the personal meet. The structures still matter enormously – thoughtful estate planning, clear documents, and a shared understanding of who does what and when can spare a family real pain down the road. But the structures work best when they sit on top of a family that has been quietly prepared to receive them. One without the other tends to disappoint.

If you’ve been thinking about what you want to pass on – and, just as importantly, to whom, and how ready they are – that’s a conversation worth having out loud. We’re here and happy to help you think it through.

This article is for general educational purposes and is not intended as legal, tax, or investment advice. Please consult your own advisors regarding your specific situation.

Ridgeline Wealth Advisors

The Owner’s Long Trail: Planning the Years Before You Sell

Ask a seasoned hiker about a big route and they’ll tell you the summit gets all the attention, but the descent is where people get into trouble. Ed Viesturs, the mountaineer, put it plainly: getting to the top is optional; getting down is mandatory. We think about that a lot when we sit with business owners, because selling or handing off a company is a lot like the descent. The years of climbing – building the thing, making payroll, growing it – get all the glory. The way down gets far less planning than it deserves, and it’s where the real risk lives.

For many owners, the business is the single largest asset they’ll ever hold, and often the least liquid. The transition from owning it to having sold it is one of the biggest financial and personal shifts a person can go through. It rewards the people who start early, and it tends to punish the ones who wait until a buyer is already at the table.

The Trail Starts Years Before the Sale

The most common regret we hear isn’t about price. It’s about timing – specifically, about how little runway an owner left themselves. The moves that most improve an eventual outcome tend to take years, not months: cleaning up the financials so the numbers tell a clear story, reducing the degree to which the business depends on the owner personally, building a management team that can run things without you in the room, and documenting the systems that live only in your head. A buyer pays more for a business that can thrive without its founder – and, not coincidentally, that same work makes the business easier and more enjoyable to run in the meantime.

Starting early also creates options. An owner with a five-year horizon can be patient, wait for the right buyer or structure, and walk away from a bad deal. An owner with a five-month horizon is at the mercy of whatever offer appears. Time, on this trail, is leverage.

Liquidity Is a Different Animal

There’s a particular disorientation that comes with turning an illiquid asset into a liquid one. For years, wealth has been tied up in something you could see, touch, and influence. After a sale, it becomes a number in an account – and suddenly the questions change entirely. How much is enough to support the life you want? How should proceeds be positioned when they arrive all at once, rather than earned gradually over time? What are the tax implications of the deal structure, and how do they ripple across the years that follow?

These aren’t questions to answer in the closing week. They’re far better handled in advance, when there’s still time to shape the structure of the sale itself rather than simply react to it. The decisions made before the transaction often matter more than the decisions made after.

The Question Nobody Puts on the Term Sheet

Then there’s the part that no valuation captures: who are you when the business is no longer yours? For many owners, the company isn’t just what they do – it’s a large part of who they are, the thing that organizes their days and their sense of contribution. We’ve watched financially successful sales leave people unexpectedly adrift, simply because no one planned for the identity transition alongside the financial one.

The owners who navigate this well tend to have thought ahead of time about what the next season is for. More time with family. A cause they want to pour into. A different kind of work, or the freedom to explore. The money is what makes those things possible, but it isn’t the thing itself – and knowing the difference ahead of time makes the descent far steadier.

Where We Come In

A good transition plan pulls all of these threads together: the operational work that makes a business more valuable and more sellable, the financial planning that turns a lump sum into lasting security, the tax and structural thinking that’s most powerful when it’s early, and the personal question of what comes next. None of it has to happen at once. But the sooner the trail is mapped, the more control you keep over how it ends.

If a transition is somewhere on your horizon – even a distant one – it’s worth starting the conversation now, while time is still on your side. We’re here and happy to help you think it through.

This article is for general educational purposes and is not intended as legal, tax, or investment advice. Please consult your own advisors regarding your specific situation.

Ridgeline Wealth Advisors

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.

Episode 74: Carrying a Language Home with Gil Jackson


Episode 74: Carrying a Language Home with Gil Jackson

Episode Description

What does it mean to be so connected to a place that even your name carries it?
Gil Jackson, known by the Cherokee name Dohi, meaning outside or outdoors, was born in
Robbinsville, North Carolina in 1951 and today lives on 30 acres just 200 yards from the spot
where he came into the world. He is a fluent Cherokee speaker, one of roughly 130 left, an elder
of the Snowbird community, and an educator who has taught at Stanford, UNC Asheville, and
Duke. In 2014, he thru-hiked all 2,200 miles of the Appalachian Trail, walking in part to honor
his ancestors on the Trail of Tears.

In this conversation, Gil takes Josh inside a tight-knit upbringing built on Gadugi, the Cherokee
construct of community, where neighbors came together to cut wood, harvest crops, and care for
anyone in need. He explains why family kept him rooted in Western North Carolina even when
opportunity called him elsewhere, how a community school preserved the language while the
wider world pushed assimilation, and why Cherokee is considered one of the ten hardest
languages in the world.

They also talk about why Gil keeps walking. From a 48-mile day in the Great Smoky Mountains
to the ladder-strewn West Coast Trail on Vancouver Island, his adventures are less about
conquering anything and more about seeing the creator’s creation. Most of all, this is a story
about a race against time: preserving a language, the knowledge of medicinal plants, and the
sacred sites that risk being lost before the next generation can carry them forward.

Episode Highlights
• 00:00 A name that means outdoors, and a home built 200 yards from where he was
born

• 02:00 The Cherokee tradition of burying the umbilical cord to connect a child to the
land
• 05:00 Why family kept him rooted in Western North Carolina despite chances to leave
• 06:00 Growing up in 1950s Snowbird: one gravel road, one light bulb per room, no TV
• 08:00 Gadugi explained: the community coming together to help in times of need
• 13:00 An aunt’s middle-class home, new clothes, and the family that raised him
• 21:00 Selling moss for 25 cents a pound to buy a guitar he still owns
• 22:00 A community school that taught English while protecting the Cherokee language
• 24:00 Only about 130 fluent speakers left, and losing two and a half each month
• 27:00 What makes Cherokee one of the ten hardest languages in the world
• 29:00 Degrees in education, administration, and planning, and leading a language
immersion school
• 33:00 How Cherokee end-of-life traditions have changed over a lifetime
• 35:00 Finding the therapeutic in streams, trees, and birdsong
• 39:00 Why he thru-hiked the Appalachian Trail in 2014 to honor the Trail of Tears
• 43:00 The brutal West Coast Trail on Vancouver Island, with 100 ladders and 10 hours
for six miles
• 45:00 A tense night cooking near foraging bears in Virginia
• 46:00 A trail family of five speaking four languages, all wanting to learn Cherokee
• 53:00 Losing the knowledge of edible and medicinal plants, and the sacred sites that
hold the stories
• 57:00 Rapid-fire: Gvgeyu (I love you), favorite sunrises, beloved teachers, and the White
Mountains

About Gil Jackson
Gil Jackson (Dohi) is a fluent Cherokee speaker, elder of the Snowbird community in
Robbinsville, North Carolina, and a lifelong educator who has taught at Stanford, UNC
Asheville, and Duke and served as principal of a Cherokee language immersion school. He
remains committed to preserving the Cherokee language, traditional plant knowledge, and the
region’s sacred sites, and is an avid long-distance hiker who thru-hiked the Appalachian Trail in
2014.

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Hosted by Josh Self, financial advisor and everyday explorer.
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Check out this episode!

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.