In this August 31, 2026 episode of the One of a Kind Financial Show Daily, host Mike Milligan, a Certified Financial Planning Professional, reviews three key August milestones: the U.S. national debt topping $40 trillion, a strong market performance for the month, and ongoing U.S.–Iran tensions that could affect oil prices. He explains why each milestone matters for personal tax and financial planning, especially the debt’s impact on future tax policy and Roth conversion decisions. Milligan then recaps a two‑week “Guru Arc” that highlighted ten influential financial voices—Michael Burry, Robert Kiyosaki, Jim Cramer, Michael Saylor, an AP reporter, Ray Dalio, Cathie Wood, Dolly Parton, Jamie Dimon, and YouTube—as sources of distinct investment frameworks. He stresses that listeners should synthesize the lessons that fit their unique situation rather than follow any single guru. The episode moves to a market outlook for the week leading up to Labor Day, noting historically low trading volume, seasonal weakness in August/September, and upcoming data releases (August jobs report, PCE inflation, September FOMC) that could amplify price moves. Milligan advises listeners to adjust budgets for fall expenses such as tuition and childcare. The show closes with a reminder of the host’s mission, contact information, legal disclaimer, and a call to subscribe.
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It's the One of a Kind Financial Show Daily. I am Mike Milligan, Certified Financial Planning Professional. I'm in San Juan, Puerto Rico today to close out the month of August, August 31st. It's 28 days until I turn 50 years old. My mission is to educate, coach, plan, and my motto is to never miss a moment. That's going to be especially true in September. But first, as we close out August, it was a big month. 3 milestones I want every listener to write down and put to memory. We recap the 10 Guru profiles we did the last 2 weeks, and we chart the week ahead, the last unofficial week of summer. College is already back in, most K through 12s back by next Tuesday. Markets closed a week from today for Labor Day. Sharpen your pencils, get out that notepad. Let's go.
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If you retained only 3 things from August, 2026. Retain these. Milestone 1, the United States national debt topped $40 trillion. I want you to write it out, a 4 followed by 13 zeros. Total US government debt crossed that $40 trillion number on August 19th, per the Treasury Department, as reported by CNBC, Reuters, and CNN. Just 5 months ago, it was at $39 trillion. A decade ago, it was at $19.4 trillion. We have doubled, more than doubled our national debt in 10 years. Per usdebtclock.org, that is roughly $360,000 of debt per US taxpayer. If we paid down $1 billion every day, On the US debt. It would take more than 109 years, more than 99.9% of people's life expectancy to pay off our debt. That's according to CNN's math. Why does this matter for your plan? Because sustained high debt is one of the reasons Jamie Dimon warns about sticky inflation and higher rates for longer. And because how the government eventually deals with the debt— taxes, spending cuts, or letting inflation eat the debt— is the single biggest tax planning variable for the next 20 years, Roth conversion decisions today are made under the shadow of $40 trillion. Milestone number 2, the stock market is on pace for a winning August. Per CNBC's market coverage heading into the month-end last trading day of today, which is today, the Dow's up about 2.1% in August, its 5th consecutive monthly advance. The S&P is up about 3%. That's the first month that's up since— would be up since May. NASDAQ up about 4%. S&P and Dow both hit all-time highs earlier this month. This is a market that spent the summer worried about tariffs, Iran, and rates and still climbed. The AI CapEx story, and just look at Nvidia's print of their earnings last Wednesday, was the fuel line. Friday closed mixed where, well, actually closed where all major indexes were down. Dow Jones was down 0. 2%. S&P down a quarter, NASDAQ down 0.52%, and S&P was down— I mean, Russell 2000 was down 1.39%. Bitcoin over the weekend though ended at about $77,800. That was milestone 2. Milestone 3 for the month of August is the geopolitical strife is not over. This weekend, the United States struck Larak Island in southern Iran. The first attack against Iran in weeks, per Al Jazeera, and confirmed by a US official. The strike targeted 2 IRGC launchers preparing to fire rockets carrying sea mines toward the Strait of Hormuz. Roughly 20% of the world's oil flows through that strait. Oil ETF USO closed Friday at $129.70, before this weekend's action. Watch it Monday morning. Higher oil is the fastest way sticky inflation gets stickier, which is the fastest way the Fed's September decision on rates gets complicated. 3 milestones: $40 trillion, a winning August, and a live Iran situation with oil in the middle. Write those down.
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No new profiles this week. Instead, rapid recap of the 10 voices we studied, 10 different lenses on the same question. How do you protect and grow money? Again, the point of those 10 profiles was how do you protect and grow money? Number 1, Michael Burry, the Big Short investor. His lesson, be willing to be early, be willing to be alone. He was when he made the call in 2006 that came to fruition. in 2008. Robert Kiyosaki, Rich Dad Poor Dad lesson, financial education beats a paycheck and assets are what pay you while you sleep. Jim Cramer, August 19th, Mad Money host and CNBC regular. His lesson is to diversify, do your homework, and know what you own, not just the ticker. Michael Saylor, his strategy, he's a Strategy, the name of his company is, and he's a Bitcoin architect. The lesson is conviction concentrated on one asset is a strategy and a huge risk. And since we portrayed him, he's looking a whole lot smarter now with Bitcoin rallying over 22%. Sweet. AP reporter's lesson: the best financial minds Read the news critically, consume finance journalism like a professional. And we learned about that from the Accenture internal memo talking about foregoing August, foregoing that last vacation with the kids before they go to college, the last one with a parent who may not see next summer. And then week 2, we hit Ray Dalio, Bridgewater. The lesson is the all-weather portfolio built for every economic season, not just the current one. We talked about Cathie Wood, ARK Invest. The lesson, thematic conviction and disruptive innovation held through volatility. In honor of Dolly Parton's death on August 25th, we did a tribute, the country legend who owned her intellectual property. Lesson, own your assets, build businesses, and give while you're alive. That's a living legacy. Last Thursday, Jamie Dimon from JPMorgan Chase. Lesson, build a fortress balance sheet, be pessimistic. And he actually does that from an institutional standpoint, but personally be optimistic. And then we closed our profiles with YouTube itself, the biggest financial influencer on earth. The lesson, Verify credentials. Look at the sources. Separate education from marketing. 10 voices, 10 frameworks. Zero of them build a one-of-a-kind financial plan for you. Your plan should be one of a kind because you're unique. Take the lessons that fit your life and leave the rest.
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Here's what a typical week leading up to Labor Day looks like in the markets and what makes this specific week different. The typical pattern is the week before Labor Day is historically one of the lowest volume weeks of the year. Portfolio managers are on vacation trying to squeeze a little bit more time out of summer. Trading desks are lightly staffed, volumes drop, and light volume can amplify moves in either direction on any surprise headline. Per Bespoke seasonal data, the S&P 500's median performance in the week around Labor Day over the past 10 years has been slightly negative, 0.1% decline. Historically, August and September are the 2 weakest months of the year for US equities. What this specific week holds, when the markets open, or Tuesday on September 1st, the markets are open and we're going to get the first trading day of a new month. We're going to see some drift Tuesday through Thursday on light volume, and then Friday we're going to see August job reports from the Bureau of Labor Statistics. This is the last big data point before the September FOMC meeting. A weak print keeps September in flux. Do they hold or do they increase? And then next Monday, Labor Day, US markets are closed, but guess what? We'll still be here on the One of a Kind Financial Show Daily with a special report. Later on the news backdrop, $40 trillion of debt in the news, US strikes on Iran this weekend, and the PCE inflation still running hot at 3.3% core. The Fed wants 2%, remember. Light volume plus heavy headlines is a recipe for moves that look larger than they should. Do not let a thin volume Wednesday, Tuesday, Thursday, Friday. Change your plan. One reminder, many colleges are already back. Most K through 12s will be back by this time next week. Family cash flow shifts this week to tuition, childcare, extracurriculars. The fall bills start hitting. This is the week to look at your September budget, not next week, guys.
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I'm learning, guys, and I'm training you to be a hungry learner. Estoy aprendiendo. So are you. 3 things to remember from August: $40 trillion market looks to end up, and 10 gurus, 1 plan, and that 1 plan should be yours. We're not chasing returns as much as we're building the one-of-a-kind financial plan. My mission again is to educate, coach, plan, and My motto is never miss a moment. If you want to connect with me, text the word IDEAS, I-D-E-A-S, to the number 600-700, or call our office at 757-909-7151. That's 757-909-7151. You can also subscribe to this daily podcast on YouTube. At 1, the number 1, dot oak radio. I'm Mike Milligan, Certified Financial Planner. I'll see you tomorrow. This has been the One of a Kind Financial Show Daily. This show is for educational purposes only and does not constitute personalized investment, tax, legal, or accounting advice. Investing involves risk, including loss of principal. Past performance does not guarantee future results. References to any person, company, or security, including Nvidia, JPMorgan Chase, ARK, Bridgewater, Berkshire Hathaway, Strategy YouTube, and the individuals profiled in the 2-week Guru Arc are for illustration and education only and are not recommendations to buy, sell, or hold any security. Debt figures, market performance figures, geopolitical events, and consensus numbers attributed to the US Treasury, theusdebtclock.org, CNBC Reuters, CNBC or CNN, Al Jazeera, the Bureau of Labor Statistics, the New York Stock Exchange, and other named sources are those sources' reporting and not those of Mike Milligan, 1031. Financial, or any affiliate. Consult your own licensed certified financial planning professional, certified public accountant, or attorney before acting. I am the founder of One Oak Financial. That's www.oneoakfinancial.com.
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