Affinity Insider | June 2026

Big transitions have a way of compressing decisions that deserve more space. We recently closed on a new home and the experience reminded me of something I see in financial planning constantly. The difference in outcomes usually isn’t access to better information. It’s having a clearer sense of what you were trying to protect before the pressure arrived.

This edition of the Affinity Insider is about staying deliberate when the environment is pulling you toward reaction, and what it looks like to lead with intention rather than urgency, whether you’re managing equity compensation through a liquidity event, thinking through your financial plan in an inflationary environment, or simply figuring out what the next chapter is supposed to look like.

Here’s what you’ll find inside:

💸 Your Finances in Focus — A practical framework for reviewing your financial plan in an inflationary environment, with an interactive checklist to help you identify what actually applies to your situation.

📈 Market & Investing Commentary — What strong earnings, narrow market leadership, and a shifting inflation picture mean for disciplined long-term investors.

🎁Featured Article— A planning framework for navigating IPOs and liquidity events with clarity — putting life, risk, and taxes in the right order.

📊 Did You Know? —  A century of bull and bear markets, and what the historical record actually says about staying invested.

🏡Behind the Scenes — The story of finding our home, what made it work, and the planning lesson hiding inside the whole experience.

I’m grateful you make room for this newsletter each month. There’s no shortage of financial noise out there, and I don’t take lightly that you’ve chosen to spend a few minutes here instead. My goal is always that something in this edition earns that time.

Let’s begin.

💸Your Finances in Focus

Is Your Financial Plan Built to Handle Inflation?

Inflation is back in the headlines and this time, it’s hitting close to home for many families.

Consumer prices rose to a three-year high in May, reaching 4.2% over the past 12 months, the highest annual rate since April 2023. Energy costs have been the primary driver, with the ongoing conflict with Iran continuing to push gasoline and other energy-related prices sharply higher. And while some moderation is expected ahead, most economists don’t expect inflation to return to the Fed’s 2% target until sometime next year.

In other words, this isn’t a headline that disappears next month. It’s a season worth planning around thoughtfully.

Elevated inflation has a way of quietly creating pressure across multiple areas of a financial plan at once: cash flow and budgeting, debt and asset allocation, retirement income, tax planning, and insurance coverage. Not every area will be relevant to your situation, but it’s worth taking a few minutes to think through which ones might be.

To help with that, I’ve shared an interactive checklist that walks through the key issues to consider during periods of high inflation. Whether you answer “yes” to one question or several, it can be a helpful starting point for a conversation.

👉 What Issues Should I Consider When Dealing With High Inflation?

📈Market & Investing Commentary

Steady Gains, Narrow Leadership, and a Shifting Backdrop

Markets extended their strong run in May, with the S&P 500 gaining 5.3% and setting multiple new all-time highs, pushing the index’s year-to-date gain to roughly 11%. Beneath the headline, though, the picture has grown more nuanced  and a few important developments are worth understanding as we head into the second half of the year.

Three Developments Shaping Markets:

1. 📈 Corporate earnings remain exceptional
With roughly 97% of S&P 500 companies having reported results by late May, approximately 85% topped earnings estimates, well above the five-year average of 78%. Goldman Sachs projects S&P 500 earnings per share of $340 for 2026, representing roughly 24% annual growth, with AI infrastructure beneficiaries expected to account for approximately half of that growth. Strong underlying fundamentals remain the primary reason markets have continued to make new highs despite an uncertain macroeconomic backdrop.

2. 📊 Technology is carrying the market and that’s worth watching
May’s gains were not broadly shared. Technology led all sectors with a 16% monthly return, while eight of eleven sectors finished lower, led by declines in Energy, Utilities, and Consumer Staples. A small group of AI-driven companies continues to account for a disproportionate share of index-level gains, which means the headline returns many investors see may not reflect how the broader market is actually performing. This concentration isn’t a reason to abandon a long-term plan, but it is a reason to stay intentional about diversification.

3. 🏦 The inflation and Fed picture is shifting, potentially for the better
Rising energy costs, driven largely by the conflict in Iran, have been the primary force pushing inflation higher this year with the annual CPI rate reaching 4.2% in May, its highest level since April 2023. That backdrop led the Federal Reserve, under newly appointed Chair Kevin Warsh, to hold rates steady at its June meeting while signaling that a rate hike, rather than a cut, is now possible before year-end.

The more encouraging development: a U.S.-Iran peace deal was announced over the weekend, which has already begun putting downward pressure on oil prices. If energy costs continue to moderate, that could meaningfully ease the inflation picture and give the Fed greater flexibility to hold rates steady or avoid hiking at all.

The Bottom Line

The underlying story in markets remains constructive: earnings are strong, the economy continues to expand, and long-term investors have been rewarded for staying disciplined through a volatile stretch. The variables most worth watching in the months ahead are whether the Iran peace holds, how quickly energy prices respond, and what that means for inflation and the Fed’s next move.

As always, we remain focused on helping clients stay disciplined, diversified, and aligned with their long-term goals amid short-term market moves.

🎁Featured Article

When Your Company Goes Public, Start Here

An IPO or liquidity event can create life-changing opportunities, but it can also bring significant pressure to make the “right” financial decisions. Questions about taxes, stock options, lockup periods, and diversification often arrive all at once, making it tempting to focus on tactics before stepping back to consider the bigger picture.

In this month’s featured article, we explore a planning framework designed to help employees, executives, and founders navigate liquidity events with greater clarity and confidence by putting decisions in the right order: life first, risk second, taxes third.

Inside the article, you’ll learn:

• Why the best IPO decisions begin with your life goals
• How concentration risk can affect both your portfolio and your future flexibility
• The behavioral traps that often influence decisions around company stock
• Why taxes should optimize a plan rather than drive it
• The key planning opportunities that often occur years before an IPO ever happens

Whether your company has recently gone public, is preparing for an IPO, or you’re simply building wealth through equity compensation, this article offers a practical framework for making thoughtful decisions when the stakes are high.

Click here to read the full article.

Did You Know? 👇

Stock returns are volatile, but a century of bull and bear markets shows that the good times have outshone the bad.

• From 1926 through 2025, the S&P 500 Index experienced 18 bear markets, or a fall of at least 20% from a previous peak, ranging from —21% to —80% across an average length of 10 months.
• On the upside, there were 19 bull markets,  or gains of at least 20% from a previous trough. They averaged 54 months in length, and advances ranged from 21% to 936%.
• When bull and bear markets are viewed together, it’s clear equities have rewarded disciplined investors.

Financial takeaway: The stock market’s ups and downs are unpredictable, but history supports  an expectation of positive returns over the long term.

📰🎧🍿What I’m Reading, Listening To, and Watching

🤖 The Trillion Dollar Gap | Aswath Damodaran on SpaceX, AI and the Big Market Delusion (Excess Returns)
An exploration on the growing disconnect between compelling narratives and underlying value, offering a thoughtful framework for evaluating today’s AI-driven market optimism.

💼 Predicting AI job exposure (Benedict Evans)
An examination of which types of work may be most affected by AI, emphasizing that technological change often reshapes jobs more than it eliminates them.

🍎 An Ode to Restraint: Lessons from the Tim Cook Legacy (Musings on Markets)
A framework for evaluating which software businesses may benefit from AI adoption and which may see competitive advantages erode as AI lowers barriers to entry.

⏳ Time’s Irreplaceable Value (First Trust)
A simple but powerful reminder that financial planning is ultimately about using money to support what matters most with the limited time we have.

📊 Social Insecurity, Surprise Edition (Mauldin Economic)
An insightful look at the latest developments surrounding Social Security and what they may mean for future retirees and long-term planning decisions.

🏡Behind the Scenes

Bouncy Grass & Big Decisions

We bought a house.

Not just any house. The one where our son, who turns four in July, ran across the backyard grass to make sure it was bouncy enough. The one where I picked him up and sat him on the ledge near what will be his bedroom window, looking out at the street below. The one that felt, from the first walkthrough, like something we could grow into.

That’s the thing about a home search. You’re not just evaluating square footage. You’re imagining a life.

Where the kids will play and whether there’s enough grass to actually run on. How the holidays will feel with a full table and people staying over. Whether Stephanie’s research and my client conversations each have the space they deserve. Whether the backyard is the kind of place a child remembers when they’re grown.

We found it. But we didn’t find it alone.

Carmen Ceja, our real estate agent, showed up to every conversation prepared, patient, and genuinely invested in what was right for our family, not just what was available. Joe Soto, our longtime lender, kept the financial picture clear and steady from the first call to the final signature. Every professional involved played their part. The right team doesn’t just make things easier. They make better outcomes possible.

Getting here wasn’t simple. Stephanie is pregnant with our second, due this fall, and was managing her career demands throughout. I was running a growing business. We were chasing a spirited child through open houses across multiple cities (squeezing in car naps where we could, which he accepted with surprising grace). There were moments of genuine excitement, moments of real uncertainty, and more than a few late-night conversations about what we actually wanted.

As I write this, the house is still mostly empty. Our son has declared it the world’s greatest hide and seek venue. He hides in his closet every single time, with the quiet confidence of someone who has invented an entirely new strategy. We are not correcting him.

We’re settling in. A new home, a new baby arriving soon, and a family that keeps growing in all the right ways. What made this process work wasn’t luck. It was knowing what we were looking for before we started looking. That’s a planning lesson as much as a real estate one, and it’s what a three-part article series launching soon is all about.

P.S. ~ The best financial decisions we make usually start the same way, not with a number, but with a question. What is this meant to support? If you’re facing a big decision and haven’t asked that question yet, it might be worth starting there.