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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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.

Episode 72: Risk in Every Form with Greg Winchester


ON ADVENTURE PODCAST |  EPISODE 72

Episode 72: Risk in Every Form with Greg Winchester

  

Episode Description

What does it take to keep saying yes to risk, in the boardroom, on the trail, and across all seven continents, for forty years and counting?

Greg Winchester calls himself an armchair explorer, but the title sells him short. Over a 40-plus-year career in commercial real estate, he has worked through the savings and loan crisis, the 2008 financial crisis, and COVID, first as a banker, then as a co-owner, and today as an investor through his family office, Summit Investors. In 2003, he and two partners bought their company from its founders in a management buyout, personally guaranteeing the entire debt with 300 employees and no safety net. As Greg puts it, it was like walking to the end of the diving board and jumping, hoping there was water below.

A lifelong Boy Scout who fell in love with the outdoors in the Roan Highlands of North Carolina, Greg went on to serve on the board of the Appalachian Trail Conservancy and to build a life of generosity that reaches all seven continents, inspired by the book Seven Summits. From an orphanage in Bolivia to a pastors’ training center in Uganda, a nearly thousand-year-old cathedral in Winchester, England, and Sir Ernest Shackleton’s grave on South Georgia Island near Antarctica, he and his wife set out to support smaller, lesser-known nonprofits and build real relationships, not just write checks.

In this conversation, Josh and Greg trace the many forms risk can take. They dig into why leverage is a two-edged sword, how diversification and dry powder let you run into the fire when others are running out, why your gut becomes a kind of superpower after twenty years in any arena, and how setting goals every year since his twenties shaped a life of purpose. Greg also shares the two questions a pair of mentors asked him in his mid-fifties, what is a noble cause you can get involved with, and what do you actually want to do, and why finishing well may be the greatest adventure of all.

Episode Highlights

         00:00  An armchair explorer who spent forty years navigating real estate’s biggest crises

         03:00  Stumbling into commercial real estate from a bank management trainee program

         06:00  The 2003 management buyout: 300 employees and everything personally guaranteed

         12:00  Jumping off the high dive and hoping there is water below

         14:00  A lucky break, a termination fee, and the real mix of hard work and luck

         17:00  Three things that get people in trouble: cycles, capital structure, and diversification

         20:00  Running into the fire in 2008 and why leverage is a two-edged sword

         23:00  The gut instinct you earn after twenty years in any arena

         25:00  Seven Summits and a vision to serve nonprofits on all seven continents

         29:00  Winchester Cathedral, a 950-year-old Bible, and Shackleton’s grave near Antarctica

         38:00  What rises to the top: relationships, faith, family, and friends

         40:00  A Boy Scout in the Roan Highlands and a lifelong love of the trail

         46:00  Moving toward something, not away, and setting goals every year since his twenties

         50:00  Finishing well and the two questions that reshaped Greg’s second act

Causes and Organizations Greg Supports

Here are the people and organizations Greg mentioned in this episode:

•    Summit Investors, his family office investing in real estate across the Sun Belt

•    Auburn University Master of Real Estate Development program, where he serves as an adjunct and industry connector

•    The Appalachian Trail Conservancy, where he served on the board

•    The South Georgia Heritage Trust, stewards of the historic church and museum on South Georgia Island

•    The National Christian Foundation, which helped guide his international giving

Free for Listeners: The Money Trail Guide

Josh’s free resource for everyday explorers is packed with practical insights on planning for any adventure, big or small, minimizing trail waste along the way (yes, that means taxes), and living with confidence toward whatever is most meaningful to you. It also includes key takeaways from recent On Adventure guests to help inspire your next steps.

Grab your copy at ridgelinewealthadvisors.com.

Connect with the On Adventure Podcast

Hosted by Josh Self, financial advisor and everyday explorer.

•    Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms

•    Follow on Instagram for short-form clips and behind-the-scenes content

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•    If this episode resonated with you, leave a review and share it with someone who needs to hear it

Check out this episode!

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

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

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

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

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

3 Simple Ways to Begin Preserving Your Family’s Memories

1. Bring Your Photos Together

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

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

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

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

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

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

2. Make Your Photos Accessible

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

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

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

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

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

3. Share and Preserve What Matters Most

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

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

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

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

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

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

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

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

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

Teresa Cox
Photo Concierge Services

photoconciergeservices.com

Episode 70: Saying Yes to the Right Invitations with Colin Stroud


ON ADVENTURE PODCAST  |  EPISODE 70

Episode 70: Saying Yes to the Right Invitations with Colin Stroud

                              

Episode Description

What if your next great adventure is not a destination at all, but a willingness to say yes to the breadcrumbs life keeps dropping in front of you?

Colin Stroud is a 26-year-old credit card rewards consultant, founder of Go Somewhere, and one of the fastest growing voices on LinkedIn in the points and miles space. He grew up in Fort Wayne, Indiana, the son of an OB/GYN and a nurse midwife who met delivering a baby together, and he was on track for a more traditional path until a six-week Spanish immersion trip to Oviedo at 16 cracked the world wide open. From there it was Italy on a $380 flight, a Catholic mission to Poland, an unlikely run at Ave Maria University in south Florida, an early marriage and a baby on the way before he had even graduated, and a first job in life insurance case design that he knew almost immediately was not it.

What followed is a story about paying attention. A coworker mentioned the Chase Trifecta. A LinkedIn post about points went viral and got picked up by The Washington Post. A side hustle turned into consulting calls, then into a community for business owners, then into a full-time business helping families and entrepreneurs unlock travel they thought they could not afford.

We talk about why early travel rewires you, what it actually takes to leave a steady paycheck, the difference between dopamine and meaning, why family life and entrepreneurship feel like the truest adventures of his life right now, and the surprising decision he and his wife made after almost moving to Hawaii. Colin makes a strong case that the go somewhere life is not always about getting on a plane, and that learning to be rooted where your feet are can be its own kind of expedition.

 

Episode Highlights

00:00  From cheap flights as a teenager to a full-time business helping people unlock travel

06:00  World Youth Day in Poland, six weeks of Spanish immersion in Oviedo, and catching the travel bug

14:00  Marriage, a baby on the way, and a first job in life insurance that did not fit

18:00  Discovering the Chase Trifecta and stepping into the points world

23:00  The first viral LinkedIn post and a Washington Post quote that changed everything

25:00  Quitting in November 2024 and going full-time on Go Somewhere

30:00  Almost moving to Hawaii, pumping the brakes, and rethinking what travel does for young kids

34:00  Why family life and entrepreneurship are the truest adventures of his life right now

39:00  Measuring yourself: finally finding feedback after years of feeling stuck

47:00  The two ingredients behind a viable internet business: clear writing and consistent humility

55:00 What adventure means now and where to find Colin online

 

Connect with Colin Stroud

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Website: gosomewhere.world

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Check out this episode!

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.