Affinity Insider | August 2026

August has a way of gathering people. Weddings, reunions, one last trip before the school year resets everything. It’s a month built for showing up for each other, and for noticing who shows up for you.

Good financial planning shows up the same way, in both the big moments and the small ones. It’s there for the liquidity event, the retirement date, the year everything changes at once. It’s also there in the beneficiary form updated before it’s forgotten, the tax projection run months ahead instead of in a scramble. Different scales, same commitment. Showing up reliably, whether anyone’s watching or not.

This edition of the Affinity Insider is about the client conversations that keep coming up as lockups end and jobs change, a market that’s been stronger than the headlines suggest, and a wedding that reminded me how much of this work often has nothing to do with numbers.

Here’s what you’ll find inside:

💸 Your Finances in Focus — The client situations we’ve been working through this month, from lockup expirations to career transitions.

📈 Market & Investing Commentary — A record earnings year, oil and inflation moving together again, and a Fed that’s saying less than it used to.

🎁 Featured Article — How my wife and I built our home search team, and the buyer brief that changed every conversation before it started.

📊 Did You Know? —  What today’s valuations are, and aren’t, telling us.

🥂 Behind the Scenes — A wedding, a five-year client relationship, and what it looks like when people really show up for each other.

Thank you for making room for this each month. It’s a small thing to ask for, and I don’t take it for granted.

Let’s begin.

💸Your Finances in Focus

How We’ve Been Helping Clients Recently

Financial planning rarely comes down to one isolated decision. Here’s what’s actually been on clients’ minds lately, in case any of it sounds familiar.

“My lockup period is ending. Now what?”
RSUs, ISOs, NSOs, cost basis, AMT exposure. We’ve been building sell-down strategies that spread the tax impact across years instead of triggering it all at once.

“Should I actually be in this DST?”
For clients holding alternative investments, we’ve been digging past the pitch deck: tenant concentration, lease terms, sponsor track record. Real diligence, not a rubber stamp.

“I’m thinking about leaving my job. What does that actually look like?”
Whether it’s going independent or stepping away from full-time work entirely, we’ve been modeling the cash flow bridge: health insurance, rollovers, and what income really looks like on the other side.

“This is going to be a big tax year. Now what?”
Equity comp, bonuses, distributions: we’ve been running bracket projections and giving strategies now, so April doesn’t bring surprises.

“What happens to what we’ve built?”
Estate planning and charitable giving strategies have come up more this year, as clients think through how their assets move to the people and causes they care about.

The quiet stuff we check anyway
Old 401(k) allocations that no longer match the timeline. Beneficiary designations that haven’t been touched in years. Account titling that’s out of date. Nobody asks about these. We look anyway.

None of this happens in isolation. Taxes, investments, career, family, retirement: it’s all connected, and the earlier we’re looped in, the more options there usually are. If something above sounds like your year, don’t wait for your annual review to bring it up.

📈Market & Investing Commentary

Broad Growth and a Quieter Fed

Markets spent July absorbing two stories at once. One is a genuine earnings boom. The other is a reminder that geopolitics and monetary policy haven’t gone anywhere. Both are worth understanding as we head into the fall.

Three Developments Shaping Markets

1. A record earnings year, broadly basedS&P 500 earnings are now tracking toward roughly 32% growth in 2026, up sharply from earlier estimates. Mid- and small-cap earnings are close behind, both near 23% growth. This isn’t a story about a handful of mega cap names. It’s showing up across the market, a shift worth noting after years of narrow leadership.
2. Oil and inflation moved togetherRenewed conflict in the Middle East pushed oil sharply higher in July. Inflation followed, running well above the Fed’s target. It’s a reminder that global events still show up directly in household costs.
3. A Fed that’s talking less, not moreNew Fed Chair Kevin Warsh has stepped back from the detailed guidance markets got used to. No more dot plot, shorter statements, fewer hints about what’s next. His view is that the Fed should react to data, not forecast it. The tradeoff is more uncertainty for markets trying to price the next move, which is part of why yields have been choppier heading into Jackson Hole.

The Bottom Line

Growth stocks led the market up in the first half of the year, then gave some of it back in July. Small and mid cap stocks, by contrast, are having a strong year, and their earnings are backing it up. This is exactly why we don’t build portfolios around one story, one sector, or one company’s earnings call.

As always, our focus remains on helping clients stay disciplined, diversified, and aligned with long-term goals amid short-term market movements.

🎁Featured Article

The Home Search: Turning Vision Into Action

Knowing what you want in a home is only half the equation. The other half is building a search around it, the right team, the right process, and a way to turn clarity into an accepted offer.

In this month’s featured article, I share how my wife and I built our home search team, the buyer brief that changed every conversation before it started, and what actually moved us from vision to offer.

Inside the article, you’ll find:

• Why the buyer brief mattered more than any single conversation with an agent
• How to sequence your team: financial advisor, agent, and lender, and why the order matters
• The financial conversation we hadn’t fully finished, and why it turned out to be about identity, not just affordability
• What we learned from the home we almost bought, and why we’re glad we didn’t
• A downloadable Home Buyer Brief template you can use to build your own

Whether you’re actively searching, assembling your team, or just starting to think about what a search might look like, this article offers a practical framework for turning a clear vision into a confident, accepted offer.

Click here to read the full article.

Did You Know? 👇

Stocks are trading a bit rich by historical standards, though not off the charts, and one of the more encouraging reasons why has to do with earnings, not just prices.

• Forward P/E ratio, or price-to-earnings ratio, measures how much investors are paying today for each dollar of company earnings expected over the next year. A higher number means investors are paying more for that same dollar of earnings, which usually means expectations are running higher too.
• The S&P 500’s forward P/E currently sits at 19.9x, above its 30-year average of 17.2x, but still inside the index’s typical range of 13.9x to 20.5x.
• Dividend yield measures how much a company pays out in dividends relative to its stock price. The current yield is 1.4%, below the 30-year average of 2.0%, another sign investors are paying more for future earnings than they have historically.
• Why valuation matters: it doesn’t predict what happens next month, but it does shape what kind of long-term returns are reasonable to expect. Buying in at a high valuation has historically meant more modest returns over the following years, while buying in at a low one has meant the opposite.
• One reason the current P/E isn’t more alarming: corporate earnings are growing faster than stock prices are. Analysts expect S&P 500 earnings to grow roughly 30% this year, well ahead of the index’s price gain of around 14%. When earnings grow faster than price, the P/E ratio comes down even as the market keeps climbing, a healthier way for valuations to normalize than a price drop.

Financial takeaway: A P/E above average isn’t a signal to time the market, and right now it’s being supported by real earnings growth rather than speculation alone. The bigger lesson is the same one that’s always true: valuations matter over the long run, but a plan built around your goals will always matter more than guessing when the next pullback starts.

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

🙃 The Upsidedown: Financial Chicanery and the Reality of the AI Bubble
Whitney Baker’s contrarian case that tightening dollar liquidity, not AI fundamentals, is the real story underneath the market’s blow-off top.

📊 US Stocks: Margin Math Tests the Earnings Story
AllianceBernstein argues that most of this year’s earnings growth is coming from margin expansion, not revenue, and margins can’t climb forever.

🧮 Moat or Mirage? The Arithmetic of AI Lab Valuations
A hard look at whether AI labs, rather than the hyperscalers building their infrastructure, end up capturing the real value.

🎙️ How to Raise a Few Billion Dollars
Fundraiser John Kim on the three laws of fundraising and why persuasion is really just desire minus fear.

⏳ Why $100 in Your 20s is Worth $500 in Your 60s
Nick Maggiulli on why the same dollar buys more joy earlier in life, and what that means for how you save versus spend.

🏡Behind the Scenes

Finding Your People

My son made a new best friend. He met him at a wedding celebration, somewhere between the cornhole boards and the lawn, and within minutes the two of them were running around like they had known each other since birth. No introductions, no small talk, no résumé exchange. Just an immediate and total commitment to being silly together.

Sometimes that is all it takes to start a meaningful friendship. An easy fit, a natural connection, nothing forced about it. What makes one last is showing up again and again for each other.

Stephanie and I were also there to celebrate a client couple who have become good friends. They were married officially in 2025, at the San Francisco courthouse, with only their closest family present. This was the celebration for everyone else. Friends and family gathered at the Long Beach Museum of Art, ocean in the background, the evening settling in over the water.

We have been working together professionally for about five years now. That is not long compared to almost everyone else in that room, some of whom had known this couple since childhood. But it has been five years of real life. Transitions, decisions that could not be undone, seasons where the plan had to change because the circumstances did. Our job in those stretches was to carry the financial parts so they could focus on the rest. That kind of work builds something. You end up genuinely invested in how someone’s story turns out.

The speeches were the heart of the evening. Friends described one of them as the person who looks out for everybody, the big sister of the group, the one who notices when you have gone quiet. The other, they said, is simply the guy you can count on. Reliable in a way that does not require explanation. Speaker after speaker landed on the same two words: kind and steady.

Things I already knew to be true. But I also learned plenty I had never heard. Where they came from. Who shaped them. The setbacks that happened long before we ever met.

I am always curious about that history. Partly because I enjoy learning how someone became who they are, and what they are building toward now. Mostly because it is impossible to give good advice without it.

This is the part of financial planning that does not show up in a projection. You can run every number correctly and still miss the person. Two households with identical balance sheets will make completely different decisions, and the difference lives in their history, their fears, what they watched their parents go through, and what they are quietly trying to build for the people they love.

Character shows up in a room like that, too. You see it in who came. How they spoke. How carefully our hosts thought about everyone’s comfort, right down to the coloring books at the kids’ table. That is not an accident. That is a couple who invests in people, consistently, over years.

There were others in attendance that evening I was glad to see. Households I have worked with for years, whose faces I knew well from our calls and whose kids I had heard plenty about but never met. Standing next to them, shaking their hands, meeting their families, was the best part of my week. Our work runs largely on video and phone meetings by design, and it works beautifully. But an evening like that one has a special kind of premium.

Here is what I keep coming back to.

Character compounds. The people who show up for others, reliably and without keeping score, end up surrounded by people who show up for them. That room was not a coincidence. It was a return on years of deposits.

Context is the whole job. The technical work is the price of admission. What actually makes advice useful is whether it fits the life in front of you, and that requires knowing the life.

The big decisions carry the weight. A good life, like a good plan, turns on a handful of high-leverage calls made carefully. Who you build it with. Where you put your energy. What you say no to. The smaller stuff can be treated as experiments. The big ones deserve real deliberation.

Congratulations to a wonderful couple. Thank you for including us. And thank you to my son’s new best friend, wherever you are.

P.S. ~ Be good to your people this month. They are the whole thing. And if you need anything from me, just hit reply.