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If 2025 taught us anything, it’s that the economy split. The top concentrated wealth by owning infrastructure while everyone else fought inflation. Heading into 2026, cheap money is gone and the Silver Tsunami takes center stage as millions of Boomer-owned businesses hit the market.

This edition breaks down who won 2025 and the two playbooks to win 2026.

The Trillionaire Trajectory

Elon Musk surged thanks to Tesla’s robotics push and SpaceX’s logistics dominance.

The Cloud Renaissance

Larry Ellison rose as Oracle became the hidden utility powering the AI boom.

The Chip Monopoly

Jensen Huang kept NVIDIA in the center of everything. Massive margins. Massive demand.

The Newsletter and Creator Economy

Not hype. Real businesses.

Morning Brew sold for seventy five million.

Milk Road sold for seven figures in under a year.

1440 reached fifteen million per year with a small team.

The creator economy matured into a stable, cash-flowing sector.

Growth normalizes.

Rates settle but stay elevated.

Inflation cools but stays sticky.

Boomers retire at scale.

The largest small-business transfer in history is underway.

Two ways to win in 2026. Start something lean or buy something boring.

Before we get into the buy vs start frameworks, here’s the quick-hit list of the best opportunities for normal people.

To kick off the new year, I looked into what businesses actually made money in 2025 and where regular operators can win in 2026.

The big winners last year:

Retail. Ecom. Energy. Tech. Healthcare.

But here’s the fun part.

Lean, simple, bootstrap-friendly businesses anyone can start or buy.

Ultra-specific products. Subscription boxes. Solve-one-problem items.

Dropship to start. Build brand later.

One van and a storage unit can turn into a mini Amazon for your city.

Businesses want AI but don’t know how to implement it.

You become the “AI person” for one niche and charge monthly.

Audits. Setup. Monitoring.

High trust and high margins.

Energy audits. Consulting. Brokering installs.

Riding huge demand and generous tax credits.

Specialty coaching. Niche health programs. Micro-telehealth services.

These are simple, profitable operators you can acquire for low multiples and grow with AI, better marketing, or just better systems.

Predictable. Boring. Reliable.

Add pickup subscriptions and revenue jumps.

Residential or commercial.

Easy to buy. Easy to scale with contracts.

Low acquisition cost.

Raise revenue with memberships and online booking.

Tiny but powerful.

Self-storage stays full even in slow economies.

Grooming. Daycare. Mobile baths.

Demand is huge and operators are old-school.

Most are run inefficiently.

Add systems and marketing and it grows fast.

If you can raise capital or secure SBA financing, buying a Boomer-owned business is the fastest route into cash flow.

Targets: HVAC, plumbing, death care, waste management, local creator businesses.

Multiples: 3 to 5 times EBITDA for most service companies.

The only red flag: owner reliance. If everything sits in one person’s head, walk away.

If you build instead of buy, keep it simple and focus on helping businesses move faster.

The AI Automation Agency

Urban farming (microgreens)

Creator-economy support services

Niche B2B newsletters

Local micro-SaaS

Low cost. High upside. Fast to validate.

The smartest move for 2026 is blending old with new.

Buy a boring Boomer business.

Add automation.

Add modern marketing.

Maybe even add a niche newsletter to grow leads and authority.

You get stable cash flow with tech-level margins.

This is where the next wealth wave will come from.

I also built a simple little site to help you find your next business to build or buy. It gives you quick ideas based on your budget, skills, and interest. Try it here

How can we help you grow?

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