SKEPTIC’S GUIDE TO INVESTING

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“We’re getting close to peace” is one of the most dangerous sentences in politics, especially when the next headline is about more missiles, more strikes, and more promises to hit harder. We take a hard look at how the word peace gets used today and why it can feel like a mirage, with leaders describing escalation as a “road to peace” while people keep dying on the ...

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Cash is the one asset everybody thinks they understand and it’s also the one most people never size on purpose. We sit down as skeptics and ask a simple question with expensive consequences: how much cash should you hold in a portfolio, and when should that number change? Steve Davenport argues that raising cash can be a rational planning move, especially when you’re funding a known ...

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SpaceX’s IPO didn’t just light up the charts, it raised a harder question: are you buying a business, or buying belief. We look at the spike after the debut, the slide back toward the offering price, and why that pattern can lure long-term investors into making a short-term decision without a risk plan.

From there, we get practical about fundamentals. We put profitability at t...

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“The Strait is open” is a comforting headline, but we don’t think it’s an investing thesis. We dig into the new US-Iran memorandum that’s being sold as a breakthrough and explain why the fine print, the missing signatures, and the political incentives make it look more like a memo of misunderstanding than a real peace agreement.

We talk through the biggest fa...

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The midterms are not just a politics story. They are a pocketbook story, and the loudest message might be the giant number on the gas station sign. We connect the affordability squeeze to the Iran war and explain why even a real ceasefire may not translate into quick relief at the pump, keeping inflation anxiety alive for months. That day-to-day pressure shapes turnout, swing voters, and the moo...

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Betting has gone mainstream, and now it’s wearing an “investing” costume. We take a skeptical look at prediction markets like Polymarket and Kalshi and ask what they really are: useful information tools, entertainment, or a fast track to bad financial habits. The moment you put real money on a short-horizon yes or no outcome, you’re not valuing a business or building a po...

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When a semiconductor ETF can rip higher in a month and a mega-cap can spike 35% in a day, it’s hard to know whether you’re watching real value being created or pure market heat. We sit down with Stephanie Lang, CFA, former Chief Investment Officer at a multibillion-dollar wealth management firm and founder of ArmorPoint Advisors, to get a fundamentals-first read on what’s actua...

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New York City can look unstoppable right up until incentives flip. We sit down with Fraser Rice to take the temperature inside the “belly of the beast” near Grand Central and talk about what a tax-the-rich political wave means for the business community, Wall Street, and anyone trying to build wealth in a high-cost, high-tax city. Ranked choice voting, media-savvy leadership, and sym...

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A summit can look monumental while changing almost nothing, and that gap is where investors get hurt. We take a hard look at the US China leader meeting and ask a simple question: what parts are pageantry, and what parts can actually move markets? Along the way, we challenge the familiar talking points about “opening China” and “reform,” and explain why those phrases ofte...

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The next wave of mega-IPOs may not be another software company. It might be SpaceX, a business that blends satellite internet, rocket launches, and defense-adjacent capabilities into one name that could be too big for investors to ignore.

We talk through what SpaceX actually is from an investing perspective: Starlink as a broadband communications network in orbit, launch services that ben...

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Tim Cook never led like a headline magnet, and that’s exactly why we wanted to stop and take his record seriously. With news swirling around Apple’s leadership structure and succession, we zoom out and ask a practical investor question: what does Cook’s style actually mean for Apple stock, for the Apple brand, and for the next decade of decision-making?

We talk through w...

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Most people think greatness is about raw talent. Then you meet someone who wins because they never waste a shot, never waste a moment, and never pretend the work is optional. That’s what I remember from caddying for Jay Siegel at The Country Club in Brookline, and it’s why this conversation stuck with me for decades.

I’m joined by author John Riley to talk about his biog...

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A ceasefire headline is easy to trade. The Strait of Hormuz reality is harder: crowded sea lanes, mixed flags, sanctions workarounds, and one “accident” that can yank oil prices and risk assets in a single day. We dig into why the probability of disruption can stay high even when diplomats say the right words and why the nightmare scenario is an incident involving a Chinese-flagged o...

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A portfolio can look “wrong” on paper and still be rational in real life. We pull back the curtain on what we actually hold, why one of us is willing to sit on a huge cash position, and how a downside-first investing philosophy changes every decision. If your main goal is staying in the game through market volatility, this conversation is built for you.

We dig into practical p...

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“Leave it alone” sounds comforting until you’ve watched a concentrated stock position implode, or you’ve lived through a year where both stocks and bonds drop together. Clem and I sit down to walk through Steve Davenport’s portfolio mindset, and the through-line is simple: risk management is not a side hobby, it’s the job. We talk about why he’ll trim po...

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Money advice sounds simple until real life shows up. We sat down with Don Jay Rice of Drumbeat of Wealth to talk about the part of personal finance most spreadsheets ignore: the emotions, beliefs, and old memories that steer our money decisions when no one is watching. If you’ve ever felt anxious opening a bill, oddly angry during a budget talk, or certain you “should” feel sec...

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A tariff isn’t a headline. It’s a line item that can turn a $100 auto part into $172.50 before you even add shipping, labor, boxes, marketplace fees, insurance, or a modest profit. We sit down with Mike Musheinesh of Detroit Axle to translate trade policy into the day-to-day reality of running a U.S. small business in the auto parts industry, where margins are thin and pricing errors...

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A six-mile shipping corridor can do more to your cost of living than a dozen earnings calls. We zoom in on the Strait of Hormuz and unpack why a disruption there can quickly push oil prices, gasoline costs, and LNG markets higher, even when energy stocks only make up a small percentage of major indexes. The real question isn’t whether you “own energy” today, it’s whether ...