How do I decide which business idea to pursue?

Three questions, every time:

"Can this 10x? Does the math work? Can AI handle 80 percent?"

What if two ideas both pass?

Only one gets the next operating period. I score them on:

• Upside
• How fast I'll get evidence
• How much output it gets per hour of my time
• Fit
• Cost of proof
• Downside
• My own capacity

Each idea ends in one of four calls: commit, test, park or stop, with a metric and a stop condition. And once I've chosen a vertical, I don't reopen it.

What makes an opportunity worse than it looks?

Time and custom work. I compare revenue potential, time burden, custom-work burden, how much can be automated and productized, whether it could support dedicated management when it's bigger, and whether it concentrates or fragments momentum.

A business that makes money but keeps me stuck in support or bug fixing can be worse than a more concentrated one.

Many small customers or a few big ones?

A few bigger ones, usually. My priors lean toward productized, reusable systems, automation, small human teams, larger-dollar customers and recurring revenue. I want to avoid fragmented revenue that leaves me managing lots of tiny high-touch businesses. Those are priors, not laws.

How do I come up with better ideas in the first place?

Talk it out with AI on your phone. Use ChatGPT by voice and talk to it like you'd talk to me. Give it your situation and your constraints, for example: a digital business related to the outdoors, launchable in the next four weeks, for less than $1,500. Then ask for obvious and non-obvious ideas.

• Say "non-obvious." If you don't, it'll keep handing you the most obvious ideas.
• Ask it to remix. When an idea is pretty good but you don't love it, have it merge a few ideas together.

Merging two ideas into one niche is often where the winner is.

How do I split time between a main bet and side bets?

Weight it heavily toward the one most likely to succeed with what you already have. In early 2026 my proposal was 80% on Local Media HQ, where we already had an audience and relationships, and 10% each on two side projects. The side bets weren't there to win yet. We just wanted them running so we weren't starting from zero later. Then give the main push about three months of going after it hard.

What if I have to pick one thing this month?

Pick what can make money soonest. When someone pushed me to choose one product in mid-2026, I picked the service that could make money right now, because the legacy brands in my network weren't doing it. I hadn't even figured out pricing yet. Picking it meant I had to go prove it.

Later that summer the same question came up again. The software I'd been working on for about 16 months was super complicated, so betting the short term on it wasn't smart. My signup form product was close: focus on it for two weeks and it'd be 100% ready. I picked the form. A peer on that call put it simply: go with whatever has the shortest path to income and buys you runway.

It helps that my bets aren't really separate. Consulting, both software products and my own local media company all serve the same customer, so I think of it as going all in on local media. The software even brings in consulting clients.

What do I do with ideas I'm not pursuing?

Park them where I can find them. I have so many good ideas that it scares me I'll lose them. I keep a Notion gallery of business ideas. Each card has the one-sentence idea and a one-sentence summary, and opens to the potential, the strategies, how AI would do it, cost per order and a small test checklist, with tags for cross-referencing.

An AI agent learned the template, so I can say "save this as a business idea" anywhere and it makes the card. Saving starts no work and no spend. Parked is the default.

How often do bets on people pan out?

Rarely, and that's fine. From working with a lot of would-be local media operators, I'd say it's not even 10% who take action and really go after it. More like 2%. You're going to be wrong most of the time. Keep giving people a shot anyway, because the one who executes can be a big win.

For what happens after you pick, see should I launch before I have a full plan.