Joe Casabona I help solopreneurs replace manual tasks with a reliable system so they can take time off worry-free. Olivia Rodrigo's super cool stage at SNL I was watching Noah Kahan, the SNL musical guest over the weekend, when I came to a realization about why I've had a pretty big resurgence in my interest in the show lately. Yes — part of it is the 50th anniversary last year and the increased media coverage around the show. Part of it is the sketches are available on YouTube and Peacock+,...
12 days ago • 4 min read
Picture this: you wake up and you have this weird feeling…but you can’t quite put your finger on it. This feeling of doubt…like you’re struggling to think clearly. Like you’re in a bit of a brain fog. “I’m sure it’s fine,” you think. Some coffee will clear that right up. You go about your day. You notice you have an issue with your website. You ask Claude, “My website isn’t displaying my podcast episodes the right way. Can you fix it?” Of course! Claude pinpoints the problem and then asks if...
26 days ago • 3 min read
For all of my talk about how terrible LLMs (AI, colloquially) usually are, it might seem surprising to you that I shelled out $100 for a month of Claude MAX*, and will likely do it again. But my beef with LLMs isn't that they exist. It's almost entirely the way people are using them, which is almost directly a result of the way AI advocates talk about them. Case in point: Cal Newport's latest podcast episode, Is Claude Mythos Terrifying? | AI Reality Check, completely debunks what Anthropic's...
about 1 month ago • 5 min read
My absolute favorite task manager is Todoist. I’ve been around the block and used all the major ones — from Remember the Milk to OmniFocus and everything in between. Todoist is the best for me. But a task manager only tells part of the story — it tells us what we got done. It doesn’t tell us anything about how we were feeling that day. How many tasks we moved or ignored. How many we checked off just so we’d stop seeing them. And it shouldn’t. I use Todoist so I know everything I have to do. I...
2 months ago • 3 min read
There’s a trend that’s giving me a ton of hope lately, where Gen-Z are ditching smart phones for dumb phones, or getting music players instead of streaming music from their phone. 2026 might finally be the year where we decide to go back outside — because they are thinking more about the purpose and use of their devices. When they help, and when they hurt. I feel like I’ve been thinking about my devices a lot lately too. Yes — the gear that we work on contributes to our productivity perhaps...
3 months ago • 3 min read
Elite athletes don’t give 100% every single day. They know better. When they’re training, they know to push themselves to get better, while not pushing so hard that they’ll get hurt. They know they need to take breaks if they’re going to perform at the best possible level when they need to. It’s something that we all need to do if we’re running a business too. Over the last month or so I’ve been trying to nail down a positioning statement that communicates the value and benefit of my...
3 months ago • 3 min read
Earlier this month, I went to Podfest 2026 and it was a blast. I gave a talk about not letting AI do your work for you. I also got to spend time with my brother, who works at Disney World. Now, for an extrovert like me, conferences are life-giving. I love meeting new people, having great conversations, and learning things to make my business, and me, better. But between the long conference days and the long Disney days, I was beat. 40-year-old me doesn’t bounce back as well as 25-year-old me....
4 months ago • 3 min read
I remember when Nextel came out with their Walkie-Talkie feature for their phones — you could push to talk over cellular. I won't deny this served in some practical settings, but it largely amounted to a bunch of ding dongs yelling into their phones at the mall, having short, fragmented conversations for all to hear. This is likely what made me hate talking to my phone. If I had the ability to type discretely while I was in public, why would I opt to tell the whole world? They don't need to...
5 months ago • 2 min read
Hey Reader, School starts this week for my kiddos. The summer flew by! Something I've been working on is revamping my welcome sequence —and along with it, a new set of emails I'll be sending out soon. This should help you — both newer subscribers who haven't gotten a proper welcome sequence, and long time subscribers who've been through this journey with me — understand what I do a little better. Look for those soon! Why You Need to be on LinkedIn if You’re a Creator with Kathleen Celmins If...
just now • 2 min read