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The Unscheduled CEO

Jonathan Courtney
The Unscheduled CEO
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  • Ok, i'm finally worried about AI. Here's my plan.
    Hey friends,I just got back from San Francisco, and holy s**t, I need to write this down before I forget the intensity of what I'm feeling right now.For the past year, I've been in the "AI is cool, but whatever" camp. I mean, I figured it would eventually matter, but not enough to reshape how I run my business today.That mindset is completely gone now. Like, completely.After a week of non-stop conversations with founders, watching demos, and seeing how businesses are actually using these tools, I'm convinced: If my company doesn't fully, deeply integrate AI tools into everything we do, we will be irrelevant in 1-2 years. It's as simple as that.The 10X RealityHere's what hit me hardest this week: right now, with just a few AI tools (ChatGPT Pro, Claude, and some other specialized apps), I'm effectively working with the productivity equivalent of:* Me* 3 junior employees* 2 assistantsAll for about $320/month. I mean, that's f*****g crazy when you think about it.That means my 14-person company at AJ&Smart could effectively operate like a 50-person agency if we get this right. Or more terrifyingly, our competitors could do the same thing. This isn't just about efficiency anymore. It's not about like, "how do we make this as efficient as possible?" It's about having a massive unfair advantage or being on the wrong end of someone else's unfair advantage.The Warning Signs I SawIn just the last two weeks:* Shopify's CEO announced they'll only hire people who are fluent in AI tools* Duolingo's CEO went further: they're eliminating contractor relationships entirely because AI + employees will be 10x more productive* Fiverr's CEO warned their freelancers that if you're just "good" at your job, AI is already replacing you* Y Combinator is focused on funding companies that turn "40-hour jobs into 40-minute tasks"These aren't edge cases. This is the beginning of a massive shift. Guys, if you think that Duolingo, Shopify and Fiverr are just outliers, they're not.Being in SF changed everythingThe internet can't give you what being physically present can. Sitting with founders, watching their workflows, seeing their laptop setups with all these AI tools running — it hits different.Every single conversation I had (and I was EVERYWHERE this week, I'm so socially drained) was about use cases. I'd come back to my hotel each night and immediately set up whatever new thing I'd learned about.I literally collected AI use cases like Pokemon cards this week. I'm just obsessing over every single person I've met, asking exactly how they're using these tools.The Subsidized AI Window Won't LastHere's something important you might not know: The current pricing of these AI tools ($20-100/month) is heavily subsidized by venture capital.OpenAI has already said publicly that once businesses start replacing employee tasks with AI (which is happening NOW), these tools will become exponentially more expensive.That $320/month I mentioned earlier? In 2-3 years, that could easily be $5,000-20,000/month.And by then, if you haven't become fluent in how to use them, you might not even be able to afford them anyway because your business will be crushed by competitors who jumped in early. You know what I mean? Like, your company might not even be big enough to be able to pay for how much these things are going to cost.What I'm Doing About ItHere's my action plan, which you can steal:* Tab-always-open rule: ChatGPT is now permanently open beside whatever I'm working on (like having water at your desk so you remember to drink)* Learn by collecting use cases: Every conversation I have now includes "how are you using AI in your workflow?"* Company integration: At AJ&Smart, we're building AI into everything we do - not just for efficiency but to 10x our output* Go where it's happening: Being in SF this week, surrounded by people building and using these tools, accelerated my understanding by months* Focus on what AI can't do: For me, that's facilitating in-person experiences. The feeling of being in a room working together still has immense value.A prediction you can hold me toI'm recording this prediction now: In 12-24 months, nearly every major company will announce some version of "AI fluency required" policies, just like Shopify, Duolingo, and Fiverr already have.Your clients are going to start asking themselves, "Why do I need to hire this person when I can just f*****g get an agent to do it? Or, like, a much cheaper person who controls multiple agents?"What You Should Do Right NowIf this post does anything for you, do this TODAY:* Pay for premium AI tools (ChatGPT Pro at minimum)* Cancel Netflix if you have to - this is more important* Learn how to use them properly (there are a million YouTube videos)* Have the tools open while you work - like, you need to always have your ChatGPT tab open next to whatever you're doing* Start collecting use cases like I amI don't have any f*****g skin in the game here. I don't care if you pay for this or not, and it's not like an affiliate. I'm just trying to give actual advice I would give to people I care about.If you're thinking "I'll wait and see," by the time you decide to jump in, the price will have skyrocketed, and your competitors will be years ahead in knowing how to use these tools effectively. You don't want to end up being one of those people like, "Oh, the market is fucked, and so I can't get work," which just means that you didn't predict what was coming.I'm telling you what's coming. Everyone is telling everyone what's coming.This isn't a trend anymore. It's a complete transformation of how work gets done. I can no longer lie to myself and think that this is something that's just like a passing trend.And unlike most changes in business, this one is happening at insane speed. It's a bit scary, but it's also very cool.Cheers,JonathanSummer Camp 2025 is SOLD OUT. Waiting list here: Join the Waitinglist. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com
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  • My weird hack for setting financial goals.
    OOPSIE, i’m back early from my sabbatical…Imagine if you could pay for the life you wanted WITHOUT leaving it up to “let’s see how this year goes” or being constantly at the whims of the shaky economy?Well… listen to this!Summer Camp 2025 is SOLD OUT. Waiting list here: Join the Waitinglist.Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com
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  • Undiagnosed ADHD Was Ruining My Life
    I didn’t really want to believe that ADHD was making my life worse. I thought ADHD was a superpower… that it wasn’t really a “real” problem.I’m starting to think I was very VERY wrong, and that’s what this week’s episode is about.Summer Camp 2025 Info:* Coming to Summer Camp? Tickets are here!* Book a call with Laura from my team to see if Summer Camp 2025 is for you!* Sales close Friday 28th of MarchCheers and love,JonathanP.S. I’m not a doctor or a therapist. Do your own research. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com
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  • Listen to my call with Jason Fried
    This is a call recording of Jason Fried, CEO of Basecamp, helping me out with some motivation issues I’ve been having. We didn’t know if we’d release it. It’s VERY raw and, of course, unedited.Here’s what we talk about:* Me losing some of my business “mojo” in recent years* Growing AJ&Smart to 10 million… or not* Why Jason thinks I need a real break from the business* A surprise reveal about some medication I’m testing out!Jason is the first-ever guest on this podcast And coincidentally, Jason was also the first ever guest on the Jake and Jonathan podcast 7 years ago!I hope some of you guys enjoy this one. Let me know if we should record one of our chats again!Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com
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  • The Stupid Habit That’s Sabotaging My Business Success
    Hey friends!Recorded this one in the car, posted without listening back so don’t know how bad it sounds.Comments—→ www.unscheduledceo.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howtobusiness.substack.com
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About The Unscheduled CEO

This podcast is like getting an occasional voice-note from an entrepreneur who's running a multi-million dollar (profit) business. It's raw, completely unedited but most importantly: actionable! Honestly, this should be called "Diary of a CEO", but that's... like.... taken already I think. The Unscheduled CEO, hosted by Jonathan Courtney is counterintuitive advice on running a Small Business by someone who's been running one for over 13 years. Jonathan Courtney is the CEO of AJ&Smart.com and Workshopper.com Got a question you want to be read out on air? Comment on the current episode here: https://howtobusiness.substack.com/ howtobusiness.substack.com
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