The Solo Chief

As someone running a one-person business and often collaborating with other independent workers, I cannot help feeling amused when I see large, hierarchical enterprises struggling with artificial intelligence. The traditional firm doesn’t seem fit for the age of hyper-acceleration. Some authors even think multinational corporations are on their way out, to be replaced by networked agentic organizations (NAOs). Is that true? Or is it wishful thinking?

If you’re a leader or change-maker, you’ve probably got a graveyard of failed frameworks and org designs behind you. The scaling model that needed a 500-page manual. The organizational change model that only transformed cash into catastrophe. The agile framework rollout that made everyone busy and nobody happy. You want something that could actually work, not just another method.

I’m a founder, intrapreneur, and former CIO rethinking governance for the one-person business, navigating sole accountability in the age of intelligent machines—informed by plenty of scar tissue. All posts are free, always. Paying supporters keep it that way (and get a full-color PDF of my book Human Robot Agent plus other monthly extras as a thank-you)—for just one café latte per month. Sometimes you realize you’ve done no actual work today. You attended meetings. You replied to messages.

When deciding between outsourcing and do-it-yourself, rent the plumbing but keep the memory, logs, and control plane under your roof. When should you outsource the infrastructure for agentic workflows, and when should you build it all yourself? I felt conflicted. For the past year, I’ve outsourced the hosting of every technology that sits underneath my AI agents (with Fibery, Make, Google Drive, and the rest). I want everything running in the cloud, and I’m happy to pay for that.

I sense an interesting paradox of technology. Let me give you some examples. I’m a founder, intrapreneur, and former CIO rethinking governance for the one-person business, navigating sole accountability in the age of intelligent machines—informed by plenty of scar tissue. All posts are free, always. Paying supporters keep it that way (and get a full-color PDF of my book Human Robot Agent plus other monthly extras as a thank-you)—for just one café latte per month.

Your LinkedIn strategy for 2026 should stop chasing reach and start publishing citable articles that both people and AI can find. Are you sick of LinkedIn carousels and infographics? Join the club. LinkedIn influencers are like CEOs of broadcast stations, fighting over shrinking territory and optimizing their irrelevance. Every piece of LinkedIn advice I’ve read in 2026 tells solopreneurs the same things. Make better carousels. Sharpen your hooks. Avoid AI sludge. Comment more.

A map of 16 second brain practices to help solo operators remember decisions, recover context, and stop breaking their own systems. Just this morning, I spent several minutes looking for the official documents of the notary. And when I found them, I thought, “Why are they here, for God’s sake?” That was at least the fifth time I’ve been looking for those same documents. Most likely, I’ll be searching for them again next year. Last week I opened a Make scenario I’d built in February.

Widesizing means AI lets one capable person do what once took a team. The economy isn’t shrinking; it’s fragmenting into smaller, scrappier units. Large tech companies shed people with the same solemn theater used for royal funerals, and half the internet reacts as if paid work itself just fell off a cliff. Yes, Block cuts jobs. Oracle cuts jobs. Amazon cuts jobs. Every week another CEO waves some consultancy’s AI slide deck around and calls it their new strategy playbook.

While most people chat with bots, a few solopreneurs run autonomous AI agents that operate their businesses 24/7. That capability gap is your temporary window to build something competitors can’t replicate. You have no time to lose. I’m a founder, intrapreneur, and former CIO rethinking governance for the one-person business, navigating sole accountability in the age of intelligent machines—informed by plenty of scar tissue. All posts are free, always.

I’m a founder, intrapreneur, and former CIO rethinking governance for the one-person business, navigating sole accountability in the age of intelligent machines—informed by plenty of scar tissue. All posts are free, always. Paying supporters keep it that way (and get a full-color PDF of my book Human Robot Agent plus other monthly extras as a thank-you)—for just one café latte per month. I wrote this piece for class 22 of ScaleUpNation‘s Board Program.