Wakefield Venture Group
Monthly Wealth Insights
September 2026
Road to 250 — Continues
A Month to Remember What We've Built — and Why It Endures
Labor Day · 9/11 at 25 Years · Estate Planning & Legacy
A Note from Chris
September has always struck me as one of the most reflective months of the year. Summer gives way to something more serious — school is back, routines return, and the calendar starts moving quickly toward year-end.
This September carries particular weight. We begin the month with Labor Day, a holiday that honors the workers and builders whose effort created the prosperity we often talk about in financial terms. And on September 11th, we mark 25 years since the worst attack on American soil in our lifetimes — a day none of us who lived through it will ever forget.
Both of these observances fit naturally into our Road to 250 series. American resilience — economic, civic, and personal — is the thread that runs through all of it. This month's feature looks at what happened to markets in the days and weeks after 9/11, and what that chapter teaches us about the relationship between national crisis and long-term financial recovery.
On the planning side, September also feels like the right time to talk about estate planning and legacy. The events of that September morning in 2001 reminded an entire generation that tomorrow is never guaranteed. Having your affairs in order isn't a morbid exercise — it's one of the most meaningful things you can do for the people you love.
As always, I'm here if you'd like to talk through anything.
Warmly,
Chris Wakefield
Wakefield Venture Group
Market Snapshot
August in Brief
August delivered a welcome rebound after July's turbulence, with all three major indexes posting gains — the first positive month for the S&P 500 and Nasdaq since May.
S&P 500 — August +2.5% Closed at ~7,686 · Hit all-time high mid-month | Nasdaq — August +3.5% Tech resumed leadership · Nvidia +8.7% on earnings |
Dow Jones — August +1.0% Closed at ~53,186 · 5th straight winning month | To Watch: September >50% Market odds of a Fed rate hike this month |
Data as of August 31, 2026. Past performance is not indicative of future results.
The month's standout story was Nvidia, which surged nearly 9% after reporting earnings well above expectations and projecting revenue growth of 70% by fiscal 2028. Rising oil prices and Fed Chair Warsh's hawkish remarks at Jackson Hole — where he signaled continued inflation concern — kept a lid on the broader rally late in the month.
Looking ahead: The Fed's September meeting is the market's primary focus. A rate hike — now better than a coin flip — would mark the first increase in this cycle and could add volatility heading into Q4. The VIX, which hit its lowest level of 2026 in August, has historically tended to rise through September and October.
Road to 250 — Feature
Labor Day, September 11th, and What American Resilience Really Means
We observe Labor Day at the start of September as a tribute to the American worker — the people whose daily effort, across 250 years, actually built the economy we invest in. The railroads, the factories, the office towers, the technology campuses — none of it exists without the accumulated work of generations. It's worth pausing, at least briefly, to remember that markets represent real human enterprise, not just numbers on a screen.
And then, ten days into the month, we arrive at September 11th.
September 11, 2001 — 25th Anniversary
"We will not forget. We will not falter. We will not fail."
— President George W. Bush, September 20, 2001
The 25th anniversary is a moment for grief, gratitude, and remembrance. It is also, within the context of this series, a case study in something our Road to 250 journey has returned to again and again: the capacity of American markets to absorb unthinkable shocks and recover.
Here is what that chapter looked like in market terms:
Sept. 11 | Markets Close for Six Trading Days In the immediate aftermath of the attacks, U.S. markets closed — the longest shutdown since the Great Depression. The New York Stock Exchange, located just blocks from Ground Zero, was among the buildings that sustained damage. | |
Sept. 17 | Markets Reopen — and Fall Sharply When trading resumed, the Dow fell more than 680 points — nearly 7.1% — its largest single-day point decline at the time. The S&P 500 lost 11.6% in that first week back. Fear was the dominant market force. | |
Late Sept. | The Fed Acts, Confidence Begins to Stabilize The Federal Reserve cut interest rates aggressively in the weeks following the attacks, providing liquidity and signaling that the financial system would be supported. By the end of September 2001, markets had found a floor. | |
2002–03 | Recovery, Complicated by the Dot-Com Bust The market's recovery from 9/11 overlapped with the ongoing dot-com unraveling. But investors who remained disciplined through both eventually participated in one of the strongest bull markets of the decade — beginning in 2003 and running through 2007. | |
Today | 25 Years On A long-term investor who held a diversified portfolio through September 11, 2001 — and through the dot-com recovery, the 2008 crisis, and the 2020 pandemic — has seen that portfolio grow in ways that would have been difficult to imagine standing in the grief of that September. That is not a dismissal of the tragedy. It is a testament to what American markets, and the people behind them, have been built to do. |
The Lesson That Holds Across Every Crisis
We've now traced American markets through the Revolutionary War debt, the Civil War, the Great Depression, the financial innovations of the 20th century, the 2008 crisis, the 2020 pandemic, and September 11th. The lesson that emerges is remarkably consistent.
Markets are not immune to tragedy, fear, or catastrophe. They price those things — sometimes violently, sometimes for extended periods. But the underlying capacity of the American economy to recover, rebuild, and grow has reasserted itself every single time.
Staying invested, staying diversified, and staying focused on the long term has not required optimism about any particular moment. It has required only trust in the pattern — a pattern now 250 years in the making.
Planning Focus
Estate Planning & Legacy: The Most Important Conversation You May Be Putting Off
The events of September 11, 2001 prompted many Americans to do something they had been avoiding: get their affairs in order. Wills were updated. Beneficiaries were reviewed. Conversations that had been delayed for "someday" were finally had. It was a painful catalyst — but also a reminder that this kind of planning is an act of love, not just paperwork.
If you haven't revisited your estate plan recently, here are the key areas worth addressing:
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A note on timing: Starting the estate planning conversation now — before year-end — gives you time to execute properly without rushing. Year-end gifting strategies and any changes related to the current estate tax environment are best addressed before December.
Let's Connect
Estate planning works best as a team effort. I'm happy to coordinate with your attorney and walk through how your financial plan and estate plan fit together.
Call:931-650-3777
Schedule a meeting:calendly.com/chris-wvg
Website:www.wakefieldventuregroup.com
Chris Wakefield | Wakefield Venture Group | Tennessee
This newsletter is provided for informational and educational purposes only and does not constitute investment, legal, or tax advice. Past performance is not indicative of future results. All investing involves risk, including the possible loss of principal. Estate planning involves legal and tax considerations that vary by individual circumstance — please consult with a qualified attorney and financial professional before making any decisions. Market data referenced is approximate and sourced from publicly available information as of August 31, 2026.
Investment Advisor services offered through Compass Advisory Partners, LLC (CAP) and Csenge Advisory Group, LLC (CAG), Registered Investment Advisors, dba Wakefield Venture Group.
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