3 Rules for Investing in Volatile Markets

In This Issue: 

  • How to Invest in Volatile Markets: The Art of Discipline and Downside Protection

  • What We’re Watching: Intel’s Manufacturing Troubles, Trump’s Gameplan to Acquire Greenland and Blue Origin’s Satellite Play

  • Deal of the Week: We found a cash flowing Winery & Vineyard Business in Michigan ($408k of Cash Flow). Click HERE for the listing (Deal Review Below)

3 Rules for Investing in Volatile Environments

Markets are dislocated. Greenland acquisition headlines compete with AI valuations hitting escape velocity. Policy uncertainty is the only constant. The VIX feels structural, not episodic.

But volatility isn't chaos—it's mispricing at scale.

The question isn't whether to invest, but how to deploy capital when newsflow overwhelms fundamentals.

Rule 1: Buy fear, sell greed

Buffett's principle isn't platitude—it's arbitrage.

When market sentiment detaches from business reality, the gap is your edge:

→ A 30% drawdown on a business with unchanged cash flows, sticky customers, and no leverage isn't risk. It's repricing.

→ The work is separating temporary dislocation from permanent impairment.

Most investors won't do the work. That's the opportunity.

Rule 2: Concentration builds wealth, diversification protects it

AI infrastructure will compound for years. That doesn't mean it should be your entire book.

Risk isn't just volatility—it's the probability of permanent capital loss multiplied by position size.

One macro shock. One regulatory change. One technical disruption. Any can crater a concentrated bet overnight.

Spread exposure across uncorrelated cash flows:

  • Businesses solving boring problems in different sectors

  • Different geographies

  • Different demand drivers

Conviction is good. Survival is better.

Rule 3: Boring businesses compound through cycles

HVAC repair doesn't care about Greenland. Roofing demand isn't correlated to gold prices.

When a pipe bursts in February or AC dies in August, the call gets made—regardless of what's happening in Beijing or on CNBC.

Non-discretionary, recurring revenue businesses with negative working capital and inflation pass-through aren't sexy. They're durable.

Recessions reveal which businesses were actually good and which were just riding momentum.

Own the former.

Volatility creates opportunity for investors who do the work while others react to headlines. Capital deployed with discipline during dislocation earns asymmetric returns.

The rest is noise.

WHAT’S HAPPENING IN THE MARKETS?

  • Intel's Manufacturing Crisis Deepens

    Intel dropped 17% despite beating earnings—weak guidance and supply shortages in its foundry business spooked investors. After rallying on government subsidies and investments from SoftBank and Nvidia, the market now demands execution.

    Why it matters: Intel's foundry pivot underpins U.S. chipmaking independence. Supply issues signal operational failure. If Intel can't deliver for customers, those subsidy dollars become sunk cost—and the TSMC alternative looks stronger.

  • Trump's Greenland "Framework" Stays Vague

    Trump announced a NATO-backed "framework deal" on Greenland after threatening European tariffs. Details remain sparse beyond "total access" for military use. Denmark insists sovereignty isn't negotiable.

    Why it matters: Arctic access means rare earths, northern shipping lanes, and forward positioning against China. If the U.S. locks in basing rights, watch defense contractors and rare earth supply chains. The tariff threat worked—now comes execution.

  • Blue Origin Enters the Satellite Internet Wars

    Bezos launches TeraWave—5,408 satellites targeting enterprise and government clients. First deployment Q4 2027, competing with Starlink and Amazon's Kuiper.

    Why it matters: Low Earth orbit is bifurcating: consumer vs. enterprise. Data centers need low-latency; governments want non-Musk alternatives. Blue Origin on schedule fragments SpaceX's dominance. Long satellite infrastructure and data center connectivity plays.

DEAL OF THE WEEK

Gravity Vineyards & Winery
Price: $3.9M | SDE: $408K | Multiple: 9.6×

Investment Summary

Established winery on 30 acres in Southwest Michigan's wine corridor, 90 minutes from Chicago. Produces 8,000 cases annually across 30 acres of vineyards (12 owned, 18 leased through 2033). Revenue of $1.5M with 27% margins. Fully absentee with seasoned team in place for 10+ years.

This is experiential retail dressed as agriculture—customers pay premium for the setting, not the product. The wine is the excuse. The experience is the margin.

Financials & Structure

  • Revenue: $1.5M

  • SDE: $408K (27% margin)

  • Real Estate: $2.9M included

  • Second location: 2,000 sf tasting room in South Haven

  • Traffic: 15,000–20,000 visitors annually

Investment Thesis

Berrien County sits at the intersection of Chicago disposable income and Midwest lake vacation demand. Over 20 wineries cluster here because the economics work: affluent tourists on 2–3 day trips, repeat visitation, and limited competition from established metro wine regions.

The multiple looks steep at 9.6×, but 74% of the purchase price is hard assets—land, buildings, equipment. Strip out real estate and you're buying the operating business at ~3× on $1M. The vineyard and production infrastructure create optionality: expand case production, host weddings, or lease capacity to other producers.

The South Haven tasting room extends revenue beyond seasonal weekend traffic, capturing beach-goers who won't drive inland. Absentee ownership with a tenured team (winemaker and vineyard manager both 10+ years) signals operational maturity.

Key Strengths

Proximity to Chicago creates built-in demand from high-income weekenders. $2.9M in real estate provides downside protection. Two locations reduce seasonality risk. Experienced team removes key-person dependency.

Critical Diligence

Revenue mix: What % tasting room vs. wholesale? Tasting room carries 70%+ margins at $25–$40/bottle. Wholesale at $8–$12 might be break-even after distributor cuts.

Team retention: Winemaker and vineyard manager stability is the thesis. Comp structure? Non-competes? Losing either post-close destroys value.

Event revenue: Is the property hosting weddings? If not, why? Permitting, insurance, or choice? This is the path to $600K+ SDE.

Lease terms: South Haven location—favorable rent? Locked in? Grape lease secure post-2033?

Bottom Line

Premium-priced lifestyle asset with legitimate cash flow in a high-traffic tourism corridor. The opportunity isn't operational efficiency—it's unlocking wedding and event revenue that wineries in affluent vacation markets command. Add digital marketing targeting Chicago, expand events, build a wine club. $408K becomes the floor, not the ceiling.

Listing is still available here.

This newsletter is for informational purposes only and does not constitute investment advice. The content is based on publicly available information, and the author makes no representations about its accuracy or completeness. Readers should conduct their own research before making any investment decisions.