Bill Gallagher

Markets go up and down. Things move left and then right. Another week goes by. The candles burn out but soon new candles take their place. I'm grateful for this moment.

Nothing collapsed. The team was better without me in the middle. I’ve been sitting on that realization for 16 years. Finally writing the book. Busy Is Broken — September 2026 BusyIsBroken.com

In 2009 I was the bottleneck for everything in my own company. Classic founder trap. So I spent 10 months learning to actually let go. Then took my family to Italy for a month in 2010. Zero calls. Zero meetings. I was certain something would collapse.

In the midst of so much fear and real suffering around the world there is also love and whimsy. Enjoy some frosting and sprinkles on your pie today.

A business lesson I learned from sailing: Less Sail, More Speed linkedin.com/pulse/less-sai… via @LinkedIn

@Aviation_Intel Galloway in another arena

You know what's disappointing? When someone can't just say "sorry, I don't know" or "that's not my wheelhouse, can't comment accurately for you." What i have seen is REALLY qualified people get platformed and deservingly so, about their experience and expertise. They are brilliant people. BUT then after the 20th podcast, 100k X user, 50th network news hit, they turn into an improv troop player and adopt the term "yes, and." In other words, they now answer all questions about anything with the same conviction that they do about the things they truly know. They are addicted to having all the answers and the attention. They would never do this in a professional setting surrounded by experts. I see this with NATSEC people, a lot of intel folks, that become sort of celebrities. They are awesome to hear, then, after becoming a known name, they get asked a defense tech question and holy shit they answer the most crazy thing and use statistics that don't exist etc with the same conviction as they talk about their core field. Then you realize, 'holy shit, is this person just totally full of shit now?' Only a few people would realize how crazy batshit their answer are on these topics. And it's not just one answer it's the second, and the 10th. All total garbage. So if they are doing this with just the little area I know about, it must be other areas beyond their core field too. Then I mark them off as lost. They got addicted to the attention and destroyed their credibility in the process, maybe not with most but with some. It's wild to watch. The most powerful thing you can say when being asked a question is "I don't know." This has become taboo in our culture. People are so fearful of not having all the answers. But it works in the opposite. Saying I don't know builds tremendous trust immediately. It's a amazing what a tiny bit of fame can do to people. Not even money, petty influencer fame.

How Do Leaders Stay Clear-Headed in the Age of AI with Bill Gallagher player.captivate.fm/episode/93d0fb…

@tom_peters Miss your presence.

This is my first tweet in a long, long time. Period. I’ve missed you all. Plan on coming back, at least to some small extent. Yippee!

Last quarter I rolled out Microsoft Copilot to 4,000 employees. $30 per seat per month. $1.4 million annually. I called it "digital transformation." The board loved that phrase. They approved it in eleven minutes. No one asked what it would actually do. Including me. I told everyone it would "10x productivity." That's not a real number. But it sounds like one. HR asked how we'd measure the 10x. I said we'd "leverage analytics dashboards." They stopped asking. Three months later I checked the usage reports. 47 people had opened it. 12 had used it more than once. One of them was me. I used it to summarize an email I could have read in 30 seconds. It took 45 seconds. Plus the time it took to fix the hallucinations. But I called it a "pilot success." Success means the pilot didn't visibly fail. The CFO asked about ROI. I showed him a graph. The graph went up and to the right. It measured "AI enablement." I made that metric up. He nodded approvingly. We're "AI-enabled" now. I don't know what that means. But it's in our investor deck. A senior developer asked why we didn't use Claude or ChatGPT. I said we needed "enterprise-grade security." He asked what that meant. I said "compliance." He asked which compliance. I said "all of them." He looked skeptical. I scheduled him for a "career development conversation." He stopped asking questions. Microsoft sent a case study team. They wanted to feature us as a success story. I told them we "saved 40,000 hours." I calculated that number by multiplying employees by a number I made up. They didn't verify it. They never do. Now we're on Microsoft's website. "Global enterprise achieves 40,000 hours of productivity gains with Copilot." The CEO shared it on LinkedIn. He got 3,000 likes. He's never used Copilot. None of the executives have. We have an exemption. "Strategic focus requires minimal digital distraction." I wrote that policy. The licenses renew next month. I'm requesting an expansion. 5,000 more seats. We haven't used the first 4,000. But this time we'll "drive adoption." Adoption means mandatory training. Training means a 45-minute webinar no one watches. But completion will be tracked. Completion is a metric. Metrics go in dashboards. Dashboards go in board presentations. Board presentations get me promoted. I'll be SVP by Q3. I still don't know what Copilot does. But I know what it's for. It's for showing we're "investing in AI." Investment means spending. Spending means commitment. Commitment means we're serious about the future. The future is whatever I say it is. As long as the graph goes up and to the right.

Any allergies? Yes, checked luggage gives me hives.

@PeterDiamandis Maybe it’s time to think about another path. More flow, better code, more efficient processors, innovation over force, a little less caffeine.

It’s all about power, connectivity, GPUs and Caffeine!

It’s Friday. Time soon to stop working. Be with family. Go on a date. Move your body. Sleep well. Reset. Write down your ideas, but save the real work for later. And whatever you do—don’t email, text, or call your team this weekend. Take the break.

So here’s my question for you: What do you and your family really need from you right now?

Lesson: there’s never a “perfect time” to step away. You have to decide, trust your team, and do it.

In 2010 I finally did something I thought was impossible: stepped away from my company for a whole month.

I turn 61 today. Grateful for the wisdom gained from 40 years of cycles and challenges—and still energized to innovate with AI and new ideas. Confidence, perspective, and gumption all in the mix. Onward.

In 2010, we went to Italy. I was fully present. The team thrived without me. That summer I learned: scaling with less struggle isn’t about someday finding the right team. It’s about changing the way you lead. It starts with the person in the mirror.

So I told my team: next summer I’m gone for a month in Europe. Then I spent 10 months practicing a new habit: stop giving answers, start asking questions. “What would you do if I wasn’t here?”

In 2009 my company was on the verge of a breakthrough. My kids were 10 & 12—the window my wife & I had promised we’d take them on long trips. But like many founders, I couldn’t imagine stepping away. The business needed me. Or so I thought.