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Escape to leverage.

After 15 years in SaaS leadership, I left corporate in August 2025 to build with AI and buy cash-flowing assets.

Escape was survival. Leverage is design. These posts tell that story in order, so start at the top.

Part 1 · Escape

Why I left, and what made it survivable

Where the money psychology comes from, why I walked away from the corporate track, and the first months after.

6 Years on an Army Cot, and the 14 Investments It Turned Into

Black Monday put my family in a single-wide at the end of a 6 mile rock road. Here's every cash flow source I own now, what each one actually paid over the last 12 months, and what a paycheck would have to pay to match it.

6 min read

A Front Row Seat to the New Industrial Revolution

Why I left a lucrative SaaS executive role for a front row seat to the AI revolution, and how cash flow plus AI made the leap less risky than it sounds.

4 min read

Bob Is My CEO. Bill Handles Bug Fixes. They're All AI.

After 15 years in SaaS, I left corporate to build with AI and buy cash-flowing assets. Here's what happened in the first seven months.

3 min read

Part 2 · Leverage

Building the systems that buy time back

The agents, the second brain, and the build-vs-buy calls behind them.

I Built My Chief of Staff Out of Markdown Files

My personal AI chief of staff runs on a folder of markdown files and a Telegram bot. Here's how the second brain is actually wired, and why it buys back my attention.

6 min read

The Daily Loop: Where the Second Brain Earns Its Keep

The markdown vault was the memory. This is the loop that feeds it, queries it, and patrols it — the morning ingest, the 4-button brief, recall on demand, and the overnight patrol. With a starter version you can set up today.

6 min read

I Cancelled 5 Apps and Built My Own Wealth Tracker in an Afternoon

I cancelled 5 finance subscriptions and built one wealth tracker in an afternoon to handle a dozen entities and a stack of K-1s. The build-vs-buy line is moving, and here's the catch nobody mentions.

4 min read

Howard Caught the Fraud. Then He Fixed My Workout.

My AI chief of staff flagged a $1,500 fraudulent charge my old process would have missed for months. Then I gave him 5 years of health data, and he pulled my best-ever training block out of it. Context is the whole trick.

3 min read

Part 3 · Judgment

Decisions along the way

When to push, when to turn around, and when the math says no.

Turning Around at 13,000 Feet

This year's misogi: 10 hours up Mount Shasta, 6,600 feet gained, no summit. Why I score the day as both a failure and a success, and the one challenge that can never be delegated to an agent.

3 min read

The Silver Tsunami Deal That Looked Like a Layup

A $1.25M manufacturing deal looked like a 33% return on paper. Then I checked what the owner actually did all day, and the math fell apart. A numbers-driven look at why most sub-$1M acquisitions are a job, not a business.

5 min read

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