The Unscheduled CEO

Hey listeners!This week’s episode of unscheduled is about my new focus at AJ&Smart… or outside of it. Lot’s to discuss and lots more in the coming weeks!ENJOY!Cheers,JonathanGet notified when a new episode drops:https://unscheduledceo.comMy active companies:AJ&Smart: https://www.ajsmart.comFacilitator.com: https://www.facilitator.comStudio: https://ajsmart.com/studioPartners: https://ajsmart.com/partners This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey all,Not in the mood to do a full pod this week so I recorded this little voicenote for you on my drive home today.Hope it tickles some of you.Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

You guys know me by now.I’m a moody, inconsistent, chaotic motherfucker. But… I still get s**t done. A lot of s**t! Isn’t that weird?It’s even weird to me! Anyway, this episode is about how I actually manage to get myself to do stuff even though I barely know anybody lazier than me.Cheers and love,JonathanP.S. leave a comment so I know you’re paying attention you cuties!!!! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey friends,I recorded a poddy about something I do that makes my life easier. A lot easier! Like… 23% easier i’d say.Enjoy!JonathanSummer Camp Mastermind Tickets: https://ajsmart.com/summercampGet notified when a new episode drops:https://unscheduledceo.comMy active companies:AJ&Smart: https://www.ajsmart.comFacilitator.com: https://www.facilitator.comStudio: https://ajsmart.com/studioPartners: https://ajsmart.com/partners This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

So the markets are turbulent again.Another recession? Who the hell knows!What I do know is that it’s STILL my job to make sure my company both survives and thrives through whatever happens.Here’s my plan to deal with it.Summer Camp Mastermind Tickets: https://ajsmart.com/summercampGet notified when a new episode drops:https://unscheduledceo.comMy active companies: AJ&Smart: https://www.ajsmart.comFacilitator.com: https://www.facilitator.comStudio: https://ajsmart.com/studioPartners: https://ajsmart.com/partners This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey!In this weeks episode of the Unscheduled CEO I show off my very simple system for turning strangers into clients.I also review some new water and talk about videogames.Oh, and I announced Summer Camp 2026 which you can get tickets to right here: https://ajsmart.com/summercamp This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey friends!This week I talk about the biggest problem i’m seeing with CEO’s using AI tools. Hint: THEY’RE MAKING LESS MONEY BECAUSE OF IT.But it’s even worse then that, because while they make less money, they get more and more lost in the AI-HOLE.Listen or watch on Youtube for the full breakdown. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

The title you’re reading isn’t an exaggeration: I’ve had a severe phobia for over 30 years and in many ways it’s controlled my life.After over 5 years of therapy and COUNTLESS other approaches, I finally faced it last week.This episode is about what happened.Oh and also I review a can of sparkling water.Thanks to everyone for listening to this absolutely useless nonsense. I love you all.Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Releasing an episode on a Sunday??Let’s chat about our first ever Experimental Creative Retreat…Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

This was a BIG week, first I got 50k views on a Youtube video… then I had my FIRST viral tweet!The only question is: what will I do with my new found fame?Let’s find out!Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

I just built a new funnel that would have taken 6 weeks and $20,000 in a few hours.This isn’t hyper or exaggeration, this is where these tools are at right now.Uhhhmm… that’s what this weeks episode is about.You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

You guys ask me all the time: “How do I get more clients???”So here I (mostly) talk about it.Enjoy!You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

HEY LOVELY PEOPLE,This is a juicy episode all about how I deal with feedback, criticism and online trolls.It’s a spicy one. Don’t listen if you don’t want spice.You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Ok ok ok, it finally clicked for me after using a new, crazy tool.The AI hype makes sense.I haven’t been this pumped about technology in like… a decade?Let’s talk about it.You can join the webinar I mentioned is right here.You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey! What’s up?This week i’ve got the beautiful Chad Littlefield (my mortal enemy) and we chatted about:* The Contribution Method (and How to Stop Exhausting Yourself Running Events)* AI is Going to Expose That Most Jobs Were Never Real* Ditching the Smartphone (and Why It Actually Worked)* The Return of In-Person Gatherings (and Why You’re Betting Big on Them)* Spirituality, Meditation, and Listening to Something BiggerThis episode was a mess audio-wise and there was a slight delay in our connection, but you’re not listening to this crap to transcend or some s**t right?You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

IM BACKYOU READY? Yeah? Ok.In this episode I talk about* How to get what you want by understanding Agency* Other stuffYou can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey!We made it to the final Unscheduled CEO episode of 2025! PHEW!In this episode I talk about* Results of my 1 year ADHD medication experiment* My life-changing mindset going into 2026* My favourite book of the year* How to make sure you stay bold in 2026See you all next year.You can listen to this episode anywhere you listen to podcasts and its also on Youtube: https://youtu.be/vDRPov6g0RkCheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey!This week I brought my friend and mentor Blake on the podcast for an open-ended conversation which ended up getting pretty personal.We talked about:* The panic attack I had after a 2-day marathon business/life design session * Why I sometimes feel sad when I see my favourite artists perform* Blake transitioning from artist to business-man back to artist* Intuition, spirituality and romantic relationshipsChapters: 00:00 - Where do I know Blake La Grange from?03:07 - Why Blake’s conversations hit so hard17:40 - Coaching with honesty, love & the pain of true feedback23:15 - When your business stops fitting you and who you are26:53 - The core moment that helped Blake understand me31:24 - The Squid Gods are making decisions for us35:40 - Finding a way to channel intuition on purpose39:44 - Everyone has intuition (but most people choose productivity instead )48:13 - How Blake knew it was time to leave his business54:35 - Finding your medium & seeing others live your potential1:04:17 - The Two-Mountain Life: Success vs Meaning1:11:10 - Prodigy, talent & why Jonathan’s using only 1%1:21:26 - Pressure & environments where Jonathan thrives1:26:28 - The feeling of actually doing the thing you’re talking about1:31:19 - Acting vs Delusion: Why doing the thing makes it real1:34:41 - A moment that changed Blake’s life1:44:50 - The call to create & resisting practicality1:45:48 - How to contact Blake (If you’re doing something interesting)You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Here’s a question for you: Why do the companies who make some of the most used Remote Work tools on the planet not work remotely?Why do most CEO’s benefit more from remote work than employees?Lots to get into in this episode. Please listen before you post your comment about how remote work is actually very valuable to you etc.You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,JonathanP.S. I did a little office tour video you can watch right here. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

For over 5 years i’ve been telling people that i’ve sort of lost my “business mojo”.Not that i’ve lost my ability to make money, but that' i’ve started to feel aimless, a bit fatigued and finding it hard to get excited about what i’m doing.Over these 5 years i’ve tried a lot of things, spent a lot of money on coaching, therapy, starting new businesses, trying new creative projects… but I keep ending up in the same place: losing interest and feeling a bit checkout-out.Oh, and, I even tried ADHD medication…. which kinda worked… till it stopped working.BUT finally, F*****G FINALLY, all of that exploration has lead me to an “Aha Moment” which has started to bring back some of that energy and purpose I thought was maybe gone forever.That’s… basically what this episode is about.Hope you get something from this.Oh, I also launched a Patreon.You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,JonathanP.S. I updated the podcast art to make it more serious and business-like This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

About a decade ago a company’s internal blueprint for everything they do was leaked.It changed everything about my business.That’s what this episode is about.You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,JonathanP.S. I updated the podcast art to make it more serious and business-like This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

From this week until March 15th 2026 i’m going to be focussing on ONE thing to grow AJ&Smart.And it’s really, reallllly simple.You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,JonathanP.S. I updated the podcast are to make it more serious and business-like This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

This week i’m talking about my day-rate, which some people are a little shocked about when they hear it.I also talk about a conference I just spoke at!You can listen to this episode anywhere you listen to podcasts and its also on Youtube:Cheers,JonathanP.S. I updated the podcast are to make it more serious and business-like This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

This week i’m talking about a success trait that’s not only measurable, but apparently learnable.Soo… yeah that’s what this is about.If you missed it, I have a new company: www.alreadythere.com You can listen to this episode anywhere you listen to podcasts and its also on Youtube: Cheers,JonathanP.S. I updated the podcast are to make it more serious and business-like This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

I finally launched the thing i’ve been too scared to create for years.I hope some of you love this and some of you think it’s extremely pointless.Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Something’s wrong. Something’s making us less happy, more lonely, feel less purpose… numbing us.You can also watch this weeks episode on Youtube if you don’t want to just listen.Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

It’s been years since Jake and I did an episode of a podcast together and this one goes DEEEEEEEP into our struggles with creativity, adhd and whatever else comes up!You can also watch this weeks episode on Youtube if you don’t want to just listen. Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

This week I talk about my struggle finding balance between being too busy and too bored and not really finding a middle-ground.I also talk about a few other things:* Our huge collab with Pip Decks* Trying to simplify some of the mess i’ve created around me* A new drink is reviewed!You can also watch this weeks episode on Youtube if you don’t want to just listen.Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

In this episode I revisit my chronic motivation issues and ADHD-related problems.I also talk about a few other things: * AJ&Smart turning 15* My favourite non-alcoholic drinks (ranked!)* How i’m planning on dealing with my motivation issuesYou can also watch this weeks episode on Youtube if you don’t want to just listen.Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey! If you haven’t heard yet: The Unscheduled CEO podcast is now on an every Tuesday schedule…. till I get sick of doing it. This Tuesday is a special one because I’m chatting with someone who’s influenced my life in more ways than I can count: Sam Ovens.He’s the CEO of the inanely successful Skool.com, which has over 17 million users, and ran one of the first and most successful businesses in the online education space: Consulting.com.Sam is fascinating, he’s obsessive, he’s unconventional. This might be an episode worth watching on the Youtube channel if you have the time this week: Cheers,JonathanP.S. You can leave comments at www.unscheduledceo.com, I read every one of them This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Let's get ESOTERIC. Also: I got food poisoning, it was super fun!Watch on Youtube: This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey everyone!Some big news in this week’s episode:* The Unscheduled CEO is back on Youtube, so if you prefer to watch and listen, you can do it right here!* I’ll no longer email you about episodes, so please subscribe either on Apple Podcasts, Spotify or Youtube if you want to keep up with the show. * The show is going to a weekly format (for an experimental 6 weeks). Episodes will land Tuesdays at 7PM PT/10AM CET* I’ll experiment with recording LIVE on Mondays. Still figuring out when exactly, but if you’re subscribed to my channel, you’ll see when i’m live.Let’s go!Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey,You need to design a Sacred Space to make work feel more special. Some weird audio issues in this episode… not sure why… :) * How to build a sacred workspace you actually love. Your environment shapes your creativity, your mood, and how seriously you take yourself.* I’ve always found that when you buy ahead of where you are. Whether it’s a bigger office, better tools, or just stuff that excites you, you naturally grow into it.* Being an entrepreneur is about taking leaps and committing—those little risks create the stakes that force you to figure it out and level up.Cheers,JonathanP.S. You can leave comments at www.unscheduledceo.com, I read every one of them This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

A second episode in one week??This one’s pretty personal.* The Offset * Why my creative life suffered in my 20s and early 30s* How i’m bringing more play and creativity back into my lifeCheers,JonathanP.S. You can leave comments at www.unscheduledceo.com, I read every one of them This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Heyyyyy,Today I decided to take a minimum 1-year break from LinkedIn. In this episode I talk about that!I also talk about:* My recent trip to California* Why I also quit instagram in 2020* I do a lot of accents* Other stuffCheers,JonathanP.S. You can leave comments at www.unscheduledceo.com, I read every one of them This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey everyone,A quick iPhone voicenote for you this week.I promise you that 99.9% of people using LinkedIn to grow their audience and get clients are doing it wrong. They might be getting engagement, but nobody’s reaching out to work with them, nobodies really making money.I am. Here’s how I do it. Cheers,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey everyone,You know those big life decisions like when to quit a job, whether to buy a house or the painful “to stay or go” decision in relationships?These kinds of decisions rarely have a clear answer and can cause a massive dilemma. Here’s my take on how to make these decisions feel easier.Cheers,JonathanP.S. it’s www.unscheduledceo.com now! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey everyone, For the last 6 years i’ve spent millions on experiments in the pursuit of making AJ&Smart more “scalable” and “sellable”.99% of them failed and we lost money and momentum.Here’s what I learned and why we’re growing again without scaling.Cheers,JonathanP.S. I’m back. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

Hey hey!As i’m recording this, a funnel I launched with my team on Wednesday has generated over 100 high-quality call bookings and over $220K in revenue. It’s only been 3 days since I switched it on.In this episode I talk about the behind-the-scenes of a brand new, hyper-successful funnel!You can see the funnel right here: book.facilitator.com A lot to unpack in this episode.Cheers,Jonathan P.S. Waiting list for Summer Camp: https://go.ajsmart.com/summer-camp This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

HEY! Ok, I recorded another episode even though I keep saying i’m taking a break.It’s too exciting!!!!Today I had Alen, a business partner, on the podcast to talk about how we're actually using AI tools in our businesses. This was only the second time I've had a guest on the show, but I figured after my AI wake-up call episode, it made sense to dig deeper with someone who's been using this stuff way longer than me.Alen's been trying to get me interested in AI for months, and I kept ignoring him. I mean, I just wasn't that excited about it. But now that I'm in full obsessive mode (you know how I get), I wanted to learn from someone who's like three chapters ahead of me, but not so far ahead that it's not relevant.Super Whisper: Just say stuff and it happens!One of the tools I'm most excited about right now is called Super Whisper. When I mentioned this at an event with 60-70 people last Friday, literally nobody knew about it. Not one person.Here's how it works: instead of typing, you just talk to it like you're explaining something to a person. But it's not just transcription, it actually understands the vibe you're trying to get across and formats it properly.I had a flood in my apartment this week (my bathtub burst), and normally dealing with that kind of admin s**t in German would be a nightmare. But with Super Whisper, I just rambled into it like: "Okay, so my bathtub burst. I need them to understand this is serious and timely. Here's what happened, put it in German, make sure it doesn't sound passive aggressive."Then I paste that into Superhuman (my email app), which takes the context of previous emails in that thread and polishes it even more. The whole thing took maybe 2 minutes instead of the 20 minutes it would normally take me to craft that email.It just feels light. No mental overhead. Just ramble your thoughts and let the AI figure out how to make it digestible.Lindy: Automation for Non-Tech PeopleAlen's been using this tool called Lindy AI, which is basically automation but with intelligence built in. It's different from Zapier because it can actually understand context.Here's a real example from his business: he used to spend a full day every month categorizing expenses for his accounting. Now he has an automation that looks at invoices in his email, extracts the amount, date, and vendor, and puts it in the right category in his Google Sheet.The cool part is the intelligence, it knows that "OpenAI LLC" should go under "Software/AI" and "HubSpot" should go under "CRM." Old automation tools couldn't do that.For DMBA, they built a flow that takes meeting transcripts from their application calls and automatically drafts personalized invite emails. Not generic templates, actually personalized based on what was discussed in the call. Their admissions person just has to check if it's correct instead of writing it from scratch.The Bigger Picture: More Output, Not Fewer PeopleWhat I'm realizing is this isn't about firing people. It's about abundance. If my 14-person team at AJ&Smart gets fluent with these tools, we effectively become a 50-person company.Like our head of finance Kyle, if he automates the boring invoicing stuff, he can help me with more creative forecasting work. Figure out how to increase profit margins. Look at interesting tax strategies. The fun stuff that actually moves the business forward.My brother Adam (who's amazing at sales but terrible at admin) is learning n8n right now to build automations for his follow-up process. If he can automate the copying and pasting, he can take three extra calls per day.Why This is Different from Previous ToolsHere's what's wild about these AI tools compared to old automation: they don't need to be compatible with each other. ChatGPT can just look at your Google Doc visually, even if there's no API integration.You can literally say "I want a dashboard that shows this, this, and this" and it'll either build it for you or explain exactly how to build it using other tools. The compatibility problem is basically solved.The Learning CurveI'm in full ADHD hyperfocus mode right now, watching every video and reading everything I can find. But what I'm learning is that I need to be the role model at AJ&Smart. I can't just tell my team to use these tools. I need to learn them first and show them how.The level of inefficiency we still have compared to what's possible makes me realize how long it's going to take most small businesses to even understand what's happening here. Which is kind of an opportunity for those of us who jump in now.What You Should TryIf you want to dip your toes in:* Super Whisper, start talking instead of typing for emails and messages* Superhuman, if you use email a lot, the AI features are genuinely useful* Lindy or n8n, for building custom automations that actually understand context* ChatGPT voice mode, just dump your thoughts for 5 to 10 minutes instead of staring at a blank pageThe key is finding tools that work with how you actually work, not forcing yourself to adapt to some generic solution.I'm still early in this journey, but having conversations like this with Alen is helping me figure out what's actually useful versus what's just hype.Alright BYE,JonathanP.S. HERE’S THE LINK TO THE FORM I MENTION NEAR THE END. https://forms.gle/ByUHDuP4c3ETfT5T8 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

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 www.unscheduledceo.com

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 www.unscheduledceo.com

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 www.unscheduledceo.com

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 www.unscheduledceo.com

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 www.unscheduledceo.com

Hey friends!It’s been a while, I wanted to say hey and tell you what i’m changing in 2025.Lot’s of news and new stuff. 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 www.unscheduledceo.com

Hey friends!Many of you have probably already seen and heard that last week we relaunched AJ&Smart.But what you don’t know is the process of getting there.It wasn’t easy. 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 www.unscheduledceo.com

Hey friends!Just got back from a life-changing few weeks in California and wanted to update you all. This is a long episode, but I think it’s an important one.Cheers and love,Jonathan This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

This is the final episode of the podcast for the summer, the year, I don’t know! You’ll now find me occasionally co-hosting Greg Isenberg’s Startup Ideas Podcast, like here: Final call for the LA Mastermind here: https://forms.gle/NKPsKydaCfGFCdyZ8Thanks everyone! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com

It’s Tuesday - let’s do this!No Youtube this week.You can find the podcast in any of these places (and more!)Apple PodcastsSpotifyOn SubstackYou can comment by going to the How To Business Blog This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.unscheduledceo.com