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!

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.

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.

AI Will Not Replace a Great Advisor. It Will Almost Certainly Replace a Good One

And why some clients will need a human in the room more than ever. 

I want to say something that I think a lot of people in my industry are afraid to say out loud.

Artificial intelligence is going to replace a great many financial advisors over the next decade. Probably most of them. The advisors who run a tidy practice doing solid, competent work – gathering documents, building plans in commercial software, rebalancing portfolios on a quarterly schedule, screening for tax-loss harvesting opportunities, drafting client letters that sound like every other client letter – those advisors are in real trouble. Not because they are bad at their jobs. Most of them are quite good. They are in trouble because the things that make them good are the things AI can now do faster, cheaper, and at three in the morning.

I am not predicting this from a distance. I use AI every day in my own practice. Anyone in my industry who tells you the technology is overrated has not actually used it. It is not overrated. It is one of the most consequential tools to come into financial services in my career, and it is improving on a timescale that should make every advisor pay close attention.

So let me be clear about what I am claiming and what I am not. I am not claiming that the human advisor disappears. I am claiming that the bar for being worth what you cost is rising quickly and that the people who used to settle for a good advisor will, before long, get a better version of that good advisor for free, or close to it, from a chatbot. The gap that survives is between the great advisor and the AI. And great is harder to define than most of my colleagues like to admit.

What AI is genuinely good at – and what “good” advisors mostly do

If you sit down and list the actual tasks a competent advisor performs in a typical week, a sobering thing happens. Most of them are tasks AI either already does well or is about to. Pulling in a client’s documents and summarizing what is in them. Comparing two retirement scenarios. Calculating a Roth conversion. Drafting a quarterly letter. Researching a tax law change. Evaluating an annuity contract. Building a cash flow projection. Spotting a missed beneficiary designation.

None of this is glamorous work, but it is most of the work. And it is the work that, until very recently, justified a full time person doing it. That justification is eroding. Software that costs a client $30 a month can now do a credible first pass on most of these tasks, and within a few years it will do a near-final pass. The advisor who built a career on being the diligent middle layer between the client and the financial machinery is being replaced from underneath by a tool that does the diligent middle layer for free.

That is the bad news. Now the good news, which is also the more interesting news.

The clients AI cannot serve well

There is a category of client for whom AI will never fully be enough, and the reason has nothing to do with technology. It has to do with the structure of the problems they are trying to solve. In my experience, three characteristics tend to define this group. Many of the people I work with fit these characteristics. The clients who need a great advisor likely have all three.

First, complicated financial situations. I am not talking about a household with a 401(k), a Roth IRA, and a mortgage. AI handles that beautifully. I am talking about the business owner whose personal balance sheet is wound around an operating company, a holding LLC, a real estate entity, and a buy-sell agreement that has not been updated since the partner left. I am talking about the family that has wealth flowing across two generations, with trusts that were drafted in different decades by different attorneys with different assumptions. I am talking about the executive whose compensation includes restricted stock, performance shares, deferred comp, and a non-qualified plan that interacts with their cash flow in ways that change every year. AI can produce a remarkably good overview of any one of these pieces. Where it struggles is in the connective tissue, the place where the entity structure, the estate plan, the tax exposure, the family dynamics (always the gasoline on the fire!), and the operating reality of a closely held business all touch each other. That is where decisions actually live, and that is where the analysis is messy enough, and the data is incomplete enough, that you need a human who has seen this kind of mess before.

Second, a high regularity of consequential decisions. Some clients live a financial life with very few decision points. They save into their plan, they hold a diversified portfolio, they rebalance on a schedule, they retire on a date, and most of the work is just steady execution. They benefit enormously from a sound plan and a low-cost portfolio, and frankly, AI can carry a lot of that load. But other clients face a steady drumbeat of real decisions. Should I take the buyout offer or hold out for a better one? Do I exercise the options now or wait? Should we sell the second home or keep it? Do we lend to our son’s startup or write a check we cannot ask back for? Do I move the trust to a different state? Do I take the partnership stake? Do I retire in eighteen months or push it three more years? When decisions of this kind arrive every few weeks rather than every few years, you do not need a tool. You need a thinking partner, someone who knows your situation cold, who you trust, who you can call on a Tuesday afternoon and say, here is what I am turning over in my head, what am I missing? That kind of relationship is not something a chat window provides, no matter how clever the chat window gets.

Third, high consequences and costs attached to those decisions. A wrong move on a $40,000 401(k) contribution is forgivable. A wrong move on a $40 million liquidity event is not. A misread on the timing of a Roth conversion can cost a few thousand dollars; a misread on the structure of a business sale can cost seven figures and a strained relationship with a sibling. When the dollar amounts get large enough, or when the decisions become irreversible enough, the value of being right goes up, and the value of being wrong goes up faster. Clients in this position are not paying for information. They are paying for judgment under pressure, and they are paying for someone to share the weight of the decision with them. That is fundamentally a human service. It always has been. AI does not change it. If anything, AI raises the stakes, because the people on the other side of these transactions…the buyer, the IRS, the opposing trustee, the estate attorney…are using AI too, and the playing field at the high end is getting more sophisticated, not less.

What “great” actually means now

I have been thinking a lot about what separates the advisors who will thrive in the next ten years from the ones who will not, and a lot about the clients who will need them. It is not credentials. It is not technical knowledge.  AI is a great equalizer on technical knowledge, and the playing field there is collapsing fast. There is no longer a scarcity premium added to knowledge.  The advisors who will thrive are the ones who do the work AI cannot do, and that work has a specific shape.

It is the work of being a thinking partner before a decision, not just a report generator after one. It is the work of pushing back when a client wants to do something you believe will hurt them, and doing it in a way they can hear. It is the work of holding a conversation across years, remembering what the client said three Christmases ago about their daughter, and connecting it to what is being decided this Tuesday. It is the work of judgment in places where the data is incomplete, the stakes are real, and the answer is not in any model. It is, in a word, presence.  The kind of presence that does not scale, cannot be automated, and is exactly the thing that the right kind of client will pay for as long as I am alive to provide it.

If you are a client of mine reading this, I want you to know I take this seriously. I am using every AI tool I can get my hands on, not to replace what I do for you, but to free up more of my time and attention for the part of the job that actually matters when your number is called. The diligent middle work…the research, the modeling, the document review, the first drafts…should be done faster and cheaper every year. That is good for you. The real work, the conversation that happens when something hard is on the table and you need someone in the room with you, is exactly where I want to be spending more of my time, not less.

And if you are reading this and wondering whether you have the kind of financial life that justifies a great advisor – whether the complexity, the decision velocity, and the stakes really warrant the relationship – that is a fair question to ask. For some people, the honest answer is no. A good chatbot, a target-date fund, and a disciplined savings habit will get them where they are going. For others, the answer is firmly yes, and the cost of being wrong about it is too high to leave to a tool that, however brilliant, has no skin in your game.

Knowing the difference is itself a financial decision. And it might be the most important one you make this year.

 

On Adventure: Lessons from the Edge

Two Walks Off the Well-Marked Path

What a 10,000-mile hiker and a credit card points cosultant have in common – and what it means for the rest of us.

If you had told me, when I started the On Adventure podcast, that two of my favorite recent conversations would be with a long-distance hiker who walked the equivalent of more than four cross-country trips in a single calendar year and a Midwestern dad who built a thriving business around airline points, I would have raised an eyebrow. On paper, they have almost nothing in common. But spend an hour with each of them and you start to hear the same note ringing underneath the very different music.

Madison Blagden and Colin Stroud both did something that scared them. They both stepped off a well-marked path. And they both came back changed – not because of the mileage or the revenue, but because of what those experiences taught them about who they actually are when the safety rails come off. I think there is a lot in their stories that the everyday explorer – and frankly, the everyday investor – can put to work this week.

Madison: Walking 10,000 Miles, Planning Almost None of It

Madison Blagden spent last year on her feet. Through-hiking the Appalachian Trail, the Pacific Crest Trail, and the Continental Divide Trail in a single calendar year is itself an audacious goal – only a handful of people have ever done it. Madison didn’t stop there. She set her bar at over 10,000 miles, walking from Florida to Newfoundland and weaving the three big trails together into a feat that no woman had previously completed. She finished. She also raised the women’s record by a couple thousand miles in the process.

What surprised me most, though, was not the scale of the accomplishment. It was her relationship to planning. Here is someone who built her year around weather windows, snowpack, and resupply logistics – and her advice to anyone considering something hard was, in her words, plan as little as you have to. Whatever you think it will cost, double it and save that much. Then go.

Her reasoning is worth sitting with. So many things will happen that you cannot predict, she said, that the energy you spend trying to control them is energy you will need later for the things you actually have to face. The hikers who do best on a long trail are the ones who can pivot – who do not get emotionally locked into a schedule or a route. The ones who white-knuckle a plan tend to suffer more, finish ragged, or quit. Madison described last year’s mid-season injury as the moment she finally let go of the last bits of control she was still holding. From that point forward, every setback, every weather change, every wrench in the gears became something she just folded into the trip.

If you have ever opened a financial plan and felt the urge to nail every variable to the wall – the exact return, the exact retirement date, the exact tax outcome – Madison’s advice translates directly. A good plan is a flexible one. Whatever you think things will cost, plan for more. Then walk.

Colin: The Quiet Quit That Wasn’t Quiet at All

Colin Stroud’s adventure looks nothing like Madison’s, and that is the point. A few years ago, Colin was sitting in an insurance brokerage in Indiana, watching his wife and two of his brothers-in-law build real audiences on the internet. He was good at his job, but it bored him, and he had been passed over for a promotion he wanted. Around the same time, he had stumbled into the world of credit card points and travel rewards as a way to take his young family on a vacation they otherwise could not afford. He started writing about it on LinkedIn, mostly to see if anyone would care.

They cared. The Washington Post quoted him after one of his earliest posts. People started asking if he would get on the phone for an hour to walk through their points strategy. He charged forty-five dollars. Then a little more. Then more. About fifteen months later, he resigned from his W-2 job and went all in on a one-person consulting practice he calls Go Somewhere. Today he is running consulting calls, building a private community for business owners, and partnering with another points expert to scale a white-glove travel-research service. He does not yet know how big it gets. He does know that nothing in his prior career – the standardized tests, the promotions he did not get, the jobs he was not great at – comes close to what he is feeling right now.

What hooked me in our conversation was Colin’s description of why entrepreneurship lit him up the way it did. It was not the income, though the income matters. It was the daily measurement. Every day he gets feedback on whether he is where he thought he was. Every post, every sales call, every new client tells him something true about his actual capability. He used the word ikigai – that overlap of what you love, what you are good at, and what people will pay you for – and said for the first time in his life, every part of him feels activated at once.

Colin also said something I want every entrepreneur and every parent listening to this to take seriously. He has experienced more dopamine, more excitement, more flow from building this business than from any travel destination he has ever been to. And his family life, while quieter, is the most meaningful thing he does. Travel, in other words, is not the adventure. The adventure is the life he is building around the people he loves. The travel is just a way to bring them with him.

What the Everyday Explorer Can Take Home

Different as they are, Madison and Colin pointed me toward the same three lessons, and I think they apply just as much to the way we manage money and build a life as they do to long trails and online businesses.

The first is that uncertainty is not the enemy. It is the proof that you are doing something real. Madison built her year around variables she could not control. Colin walked away from a paycheck without knowing what would replace it. In both cases, the willingness to live with not-knowing was what unlocked the experience. We tend to treat uncertainty in our financial lives as a thing to be eliminated. It cannot be. The better question is whether your plan can absorb a surprise without breaking – and whether you have left yourself enough margin, financially and emotionally, to keep walking when the weather turns.

The second is that the people who do the most talk about it the least. Madison observed that on trail, the loudest people in the room have usually done the least. The ones with the real accolades sit quietly in the corner. I have seen the same dynamic in money. The truly wealthy people I have worked with rarely tell you anything about it. The ones loudly counting their wins are usually the ones with the most to prove. If you are doing the work, the work will speak. You do not have to.

The third – and this is the one that has stuck with me longest – is that the cliff edge is the whole point. When I asked Madison what she would say to someone standing on the edge of a decision that scared them, her answer was just, do it. Not because every adventure works out. Some do not. But because nobody she has met in the trail community regrets going and finding out it was not for them. The ones with regret are the ones who stayed home. Colin’s version of the same line was that everyone has a hundred-thousand-dollar idea sitting in their Google Drive, and most people will never act on it.

You probably have a version of this too. A trip you have been talking about for five years. A career move you keep telling yourself you will make next year. A conversation you have been avoiding. A plan you have been afraid to commit to on paper. The everyday explorer is the person who, knowing they cannot control the outcome, takes the next step anyway – and trusts that whatever shows up next, they will figure out how to keep walking.

That, more than anything else, is what I keep hearing from the guests on this podcast. And it is the kind of mindset I want for the people I am lucky enough to work with at Ridgeline. A flexible plan. A long view. The honesty to admit you cannot know everything in advance. And the willingness to walk into the unknown anyway, because the alternative – staying parked at the trailhead, indefinitely – is not actually safer. It is just stiller.