Jay Owen

Good customers want the truth, told kindly. They can tell when you're flattering them.

Business owners: what's one task you handed to AI this year that you'd never go back to doing yourself?

Anthropic gave analysts an AI agent randomly set to lean one way on judgment calls. They went with its lean 86% of the time, and 77% repeated its arguments. Decide what you think before you read the agent's recommendation.

Retrain your team on AI before you replace anyone. Most teams are more ready than their leaders think.

I gave my team a new rule. When you walk out of a client meeting, do as much of the work as you can right then instead of making it a task. Context is freshest right after. With AI, the recap and the follow-up email can be done before you're back at your desk.

People: "I don't trust AI with my data." Me: "But you use gmail?" People: "yeah." Me: "That's kind of the same thing."

Delaware is drafting a law that would let an AI agent run a whole company. I run my companies with agents doing a lot of the work, and every one has a person on my team whose name is on it. Keep a person accountable at the top.

What was your client dealing with the moment they hired you? Build your marketing around that situation.

Spent the weekend in a room with business owners who run AI inside their companies every day. Nobody gave a keynote. Each owner put their real system up on the screen, and the rest of us picked it apart. Some of it was held together with duct tape. Some of it was better than software people pay for every month. Everybody walked out with a list of things to fix on Monday. If you're building with AI by yourself, go find a room of people who will tell you the truth about your setup. You'll learn more in an afternoon than in a month of watching videos.

Talk to AI like a smart friend who knows a lot about a lot. There's no secret syntax.

Be humble enough to be wrong and confident enough to decide anyway.

Spend an hour researching your big idea before you spend a dollar on it.

Right now I'd hire for continual curiosity over almost any credential. Curious people keep checking whether last month's broken AI tool works today.

Your business was never only yours. Run it like something you'll hand back.

Someone explain to me why @SouthwestAir thought that garlic and onion pretzels were a good flavor choice with 200 people stuffed in a metal tube?

Southwest: the internet is free, but it’s useless. @Starlink for all!! 😅

When I’m in situations where I have to type instead of talk to my computer it makes me very aggravated. That’s about as first world of a problem as you can get.

Every yes is a no to something else, and too often it's the dinner table.

103 nonprofits applied for our $50,000 Nonprofit Service Grant. Today our whole team gave the one we picked a full day of strategy, design, video, and web work. Here's the order we did it in, and why it matters for anyone building a brand. The nonprofit is Hadassah's Hope, a Jacksonville ministry that goes to women who are being exploited and trafficked. They show women the love of Jesus with a hot meal and a real friendship, then walk with each one toward safety. We spent the morning on messaging and strategy. Everyone sat in one room and worked through the StoryBrand framework with their team until the message was clear enough to say in one breath. Then we divided and conquered. Video, the website, landing pages, social content, and more, all built from that same message. That order is the whole lesson for me. When the message comes first, a whole team can build at the same time and it still sounds like one organization. When it comes last, you spend months fixing copy that never fit. They'll roll it all out in the new year. This was also launch day for Nonprofit Builders, our new division for nonprofits and ministries: nonprofitbuilders.com We're doing this again next year. Tag a nonprofit leader who should apply.