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TitreDateDurée
Why relaunching AJ&Smart drove me a little mad11 Oct 202400:52:20

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
Rediscovering creativity and joy in my work15 Aug 202401:04:17

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
Voicenote: Designing your workspace (so you get more done!)02 May 202400:09:48

This is a new mini-episode format called a Voicenote!

When something comes to mind that I just can’t wait to put out on a Tuesday, i’ll make a voicenote and upload it!

I won’t email you about these episodes, even if you’re on the Substack mailing list (I want to avoid spamming you), so please make sure you’re subscribed to The Unscheduled CEO podcast in any of the podcast apps.

You can find the podcast in any of these places (and more!)

Apple Podcasts

Spotify

On Substack

Lemme know if you enjoy this mini format! You can comment by going to the How To Business Blog

Join my LA business mastermind this summer: https://forms.gle/NKoeFdQH7NsMaKgy5



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
Do this and get ONE NEW CLIENT every month 30 Apr 202400:44:50

It’s Tuesday - let’s do this!

This week’s episode is also available on YouTube if you want to watch some of the examples I talk about. (Just go to youtube and type in “Unscheduled CEO”)

You can find the podcast in any of these places (and more!)

Apple Podcasts

Spotify

On Substack

Lemme know if you enjoy this mini format! You can comment by going to the How To Business Blog

Apply for my LA business mastermind this summer —https://forms.gle/NKoeFdQH7NsMaKgy5

To leave a comment go to howtobusiness/substack.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
Voicenote: Why you never finish anything25 Apr 202400:13:35

This is a new mini-episode format called a Voicenote!

When something comes to mind that I just can’t wait to put out on a Tuesday, i’ll make a voicenote and upload it!

I won’t email you about these episodes after this one, even if you’re on the Substack mailing list (I want to avoid spamming you), so please make sure you’re subscribed to The Unscheduled CEO podcast in any of the podcast apps.

You can find the podcast in any of these places (and more!)

Apple Podcasts

Spotify

On Substack

Lemme know if you enjoy this mini format! You can comment by going to the How To Business Blog

Apply for my LA business mastermind this summer —https://forms.gle/NKoeFdQH7NsMaKgy5

Thanks for reading How To Business ! Subscribe for free to receive new posts and support my work.



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 simple "travel hack" I use to become more successful23 Apr 202400:26:39

This is a super special episode because I’m announcing the very first in-person Unscheduled CEO event!

Listen to the episode first, then fill out this form if you’re interested in applying to attend: https://forms.gle/NKoeFdQH7NsMaKgy5

It’s gonna be a super fun, one-off, special weekend!

In this episode:

* How to spend time with more ambitious people

* How to find more ambitious people

* Why it can be lonely to be ambitious

* How to spend time with people who have “made it” to where you want to be

* The Google form I mentioned: https://forms.gle/NKoeFdQH7NsMaKgy5

Let’s go!

To leave a comment go to howtobusiness/substack.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
Our biggest product of 2023 FAILED and lost us $1,450,000 (here's why...)16 Apr 202400:31:31

We made $1,450,000 (yes that’s “million”!) LESS in 2023 than we did in 2022.

Was it the economy?

Nope (but of course everyone likes to make that excuse).

Ah, must be our industry going through changes? Layoffs?

Nope.

Wait…. Online courses are dead, right??

NO! It’s much more simple than that: We went against our “Zone of Genius” as a company. To leave a comment go to howtobusiness/substack.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
This tactic made us an extra $120,000 this week!09 Apr 202400:33:03

A small marketing experiment is set to bring us in an extra, unexpected $120,000 this week and it signals a change in strategy at AJ&Smart (credit to Dom and Laura for the idea and Rebecca and Ryan for executing it!)

* Why we made LESS money in 2023 for the first time in AJ&Smart history

* Why AJ&Smart not growing can mean the company simply becomes irrelevant

* A marketing tactic we’ve been playing with that boosted our revenue by over 100k this week alone

* Why so many entrepreneurs just never get momentum!

To leave a comment go to howtobusiness/substack.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
97% of entrepreneurs don't know this success hack (seriously)03 Apr 202400:24:02

I hadn’t heard this hack before, but now I’ll NEVER stop talking about it. Let me know what you think in the comments!

* A new success and productivity hack I’m going to teach all the people I’m coaching starting from next week

* AJ&Smart’s first new product using this hack

* A new idea for helping entrepreneurs get s**t done faster

To leave a comment go to howtobusiness/substack.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
E15: I kinda hated running AJ&Smart for years + My favourite business podcast25 Mar 202400:33:49

I’m back from NYC and I’m excited about the business!

* I talk about the process of designing and positioning the product/marketing for our new in-person training

* Why I didn’t enjoy running AJ&Smart

* Why I’m back running the “day-to-day” of the business after delegating everything for years

* Why i’m excited again

* The best thing you’ll ever listen to when it comes to entrepreneurship

To leave a comment go to howtobusiness/substack.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
E13: You're Probably Lying to Yourself About What You Want13 Mar 202400:08:21

My flight got cancelled so here’s a quicky.

Episode recorded on the TP-7 from Teenage Engineering, actually sounds way better than I expected. https://teenage.engineering/products/tp-7

The Derek Sivers chapter i’m reading: https://sive.rs/arv

In this episode:

*How to figure out what you value. That’s it!

To leave a comment go to howtobusiness/substack.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
E12: How to charge more than everyone else for what you do20 Feb 202400:36:02

Hey!

In this episode:

*How to calculate your day-rate

*How to double your day-rate

*This mindset makes you less money

To leave a comment go to howtobusiness/substack.com

Thanks for reading How To Business ! Subscribe for free to receive new posts and support my work.



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
Goodbye, for now (+ Summer Mastermind update)04 Jun 202400:09:30

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/NKPsKydaCfGFCdyZ8

Thanks 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
E11: Is Work Just a Means to an End? 06 Feb 202400:15:07

Hey!

In this episode:

*Can work create any meaning or is it just something you do to make money so you can live your “real life”

* What happens when you treat work as a “means to an end”.

* Am I Tony Robbins now?

To leave a comment go to howtobusiness/substack.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
E10: Where you live actually matters (City or Nature?)30 Jan 202400:19:47

Hey!

In this episode:

*Post-covid patterns that caused many people to play the career game on “hard mode”

*Me sniffling a lot

*That’s it.

To leave a comment go to howtobusiness/substack.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
E9: This Product Solved My Phone Addiction + How To Ruin Your 2024 05 Jan 202400:59:37

Hey there! its 2024!

In this episode:

*My plan to turn around AJ&Smart’s profits in 2024

*A cool new product I got that’s solving my phone addiction

*How to feel terrible in 2024

To leave a comment go to howtobusiness/substack.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
What worked and what DIDN'T work in 2023 22 Dec 202300:49:13

A new episode just before the Christmas break??? Jingle f*****g bells!

In this episode:

*Did we double our revenue in 2023 as I said we would?

*My favourite products and life hacks in 2023

*My new relationship with alcohol

*How I’m setting goals for 2024

No video version this time, couldn’t find the camera.

Thanks for reading How To Business ! Subscribe for free to receive new posts and support my work.



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
New Study PROVES that Money Makes You Happier + This is the FINAL Episode - THE UNSCHEDULED CEO EP.802 Mar 202300:35:22

Guess who's already bored of doing this podcast? HEHEHEHE

*Money makes you happier (New Study)

*Yes, the podcast is dead (for now)

*Pee pee poo poo

Video version:



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
E7: The Remote Work Revolution is DEAD 23 Feb 202301:00:24

Amazon ends its remote work policy, I think it's a good thing.

* Why Remote work isn't always a good thing for employees

* Is the podcast ending?

* That's pretty much it for this week

Join the substack: https://howtobusiness.substack.com/

Video version:



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
E6: How To Hack Life To Get What You Want + Our BEST Team Retreat Ever!15 Feb 202300:54:24

A quick episode this week!

* Team Retreat recap

* Why life is a videogame NOT a movie

* Why you should choose the right role models

* A life & career hack to get what you want



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
E5: How To Figure Out What Makes You Happy (A Simple Exercise) 06 Feb 202302:00:14

* Watch the video instead: https://youtube.com/@theunscheduledceo

* How to figure out what you want to do in life and what makes you happy

* Our upcoming company retreat plans

* and I tell you how we moved from charging by the hour and negotiating with clients to selling packages and getting paid in full



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
E4: Our Business Model Was LEAKED & Sam Ovens Kills His $4 Million Dollar Mastermind30 Jan 202301:27:48

* It’s a video podcast now too! https://youtube.com/@theunscheduledceo

* How to get your dream mentor to help you

* Sam Ovens KILLS his $36,000 private mastermind

* and I react to our LEAKED business model and tell you what’s true and what’s BS



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
03: Our #1 MOST EFFECTIVE Marketing Tactic + How We Started AJ&Smart (by accident)24 Jan 202301:33:29

Didn’t feel like podcasting today BUT DID IT ANYWAY, here’s what I discuss:

* The most effective marketing technique we’ve ever used at AJ&Smart

* How to become the leader of your friend group

* How I started AJ&Smart with zero clients or connections

* The EXACT brand of sunglasses Pierce Brosnan loves

* The secret behind the naming of AJ&Smart

Got a question for next week’s Mailbox segment? Comment below if you’re listening on Substack or find us over on the How To Business substack.



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 don't need to find your "purpose" to make your first million28 May 202400:20:03

It’s Tuesday - let’s do this!

No Youtube this week.

You can find the podcast in any of these places (and more!)

Apple Podcasts

Spotify

On Substack

You 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
02: A New Concept that Will Make You 23% Happier + Giving Away my Unused 7-Figure Ideas17 Jan 202301:45:23

A lot going on in this episode, and I am finding my feet in terms of recording, here’s what I discuss:

* A new AJ&Smart product launch (secret free access)

* A complex negotiation between 2 AJ&Smart departments

* Why “De-Atomization” will make you happier in all aspects of your life

* Money advise i’d give to my daughter when she’s 20

* Giving away an idea that would make us millions but we don’t have time for

Got a question for next week’s Mailbox segment? Comment below if you’re listening on Substack or find us over on the How To Business substack.



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 started a new Podcast! Here's Episode 1!10 Jan 202301:04:47

Testing 1,2,3, is this thing on?

Ummm HEY! I’ve just launched a new weekly podcast called The Unscheduled CEO!

You should be able to get it on all your favourite podcasting apps by next week but for now, you’ll prob have to listen to it in SUBSTACK.

I literally just recorded this so it’s HOT OFF THE PRESS. Like, here’s me recording it one hour ago:

Got a question for next week’s Mailbox segment? Comment below if you’re listening on Substack or find us over on the How To Business substack.



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
Voicenote: I'm feeling a little overwhelmed...23 May 202400:09:26

Phew, it’s been busy!

You can find the podcast in any of these places (and more!)

Apple Podcasts

Spotify

On Substack

Lemme know if you enjoy this mini format! You 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
Forgetting this sales hack probably lost me millions 21 May 202401:06:03

It’s Tuesday - let’s do this!

This week’s episode is also available on YouTube if you want to watch some of the examples I talk about. (Just go to youtube and type in “Unscheduled CEO”)

You can find the podcast in any of these places (and more!)

Apple Podcasts

Spotify

On Substack

You 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
Voicenote: Happy Birthday to Pierce Brosnan 16 May 202400:05:13

The most important day of the year is here!

You can find the podcast in any of these places (and more!)

Apple Podcasts

Spotify

On Substack

Lemme know if you enjoy this mini format! You 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
Every millionaire I know uses the "Canvas Strategy"14 May 202400:57:28

It’s Tuesday - let’s do this!

This week’s episode is also available on YouTube if you want to watch some of the examples I talk about. (Just go to youtube and type in “Unscheduled CEO”)

You can find the podcast in any of these places (and more!)

Apple Podcasts

Spotify

On Substack

You 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
Voicenote: Have you heard of the "Going First" principle?09 May 202400:10:50

It’s Thursday, here’s a Voicenote!

When something comes to mind that I just can’t wait to put out on a Tuesday, i’ll make a voicenote and upload it!

I won’t email you about these episodes, even if you’re on the Substack mailing list (I want to avoid spamming you), so please make sure you’re subscribed to The Unscheduled CEO podcast in any of the podcast apps.

You can find the podcast in any of these places (and more!)

Apple Podcasts

Spotify

On Substack

Lemme know if you enjoy this mini format! You 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
The ONLY Time-Management Hack for Chaotic Entrepreneurs07 May 202400:37:42

It’s Tuesday - let’s do this!

This week’s episode is also available on YouTube if you want to watch some of the examples I talk about. (Just go to youtube and type in “Unscheduled CEO”)

You can find the podcast in any of these places (and more!)

Apple Podcasts

Spotify

On Substack

You 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
How to make work feel like play 11 Jan 202500:39:00

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
My weird hack for setting financial goals.24 Apr 202500:46:29

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
Undiagnosed ADHD Was Ruining My Life24 Mar 202500:29:54

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 March

Cheers 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
Listen to my call with Jason Fried 04 Mar 202500:48:11

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
The Stupid Habit That’s Sabotaging My Business Success 26 Feb 202500:22:07

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
Ok, i'm finally worried about AI. Here's my plan.12 May 202500:32:34

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 Reality

Here'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 assistants

All 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 Saw

In 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 everything

The 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 Last

Here'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 It

Here'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 to

I'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 Now

If 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 am

I 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
The AI tools i'm actually using daily22 May 202501:27:01

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 People

Alen'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 People

What 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 Tools

Here'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 Curve

I'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 Try

If 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 page

The 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,Jonathan

P.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
My new funnel made $100K in the first hour 02 Jun 202500:50:03

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
I've learned an expensive lesson. 10 Jun 202500:49:14

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,Jonathan

P.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
A decision-making theory that changed my life + business 16 Jun 202500:35:56

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,Jonathan

P.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
Exactly how I use AI to get paying clients on LinkedIn (Voicenote)09 Jul 202500:32:02

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
I’m finally ready to tell you about “The Offset” 14 Aug 202500:29:12

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 life

Cheers,Jonathan

P.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
Why I Quit LinkedIn Today11 Aug 202500:43:51

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 stuff

Cheers,Jonathan

P.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
You need a Sacred Space 21 Aug 202500:18:38

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,Jonathan

P.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
What's a CEO actually supposed to focus on? + This is a Weekly Show now!02 Sep 202500:31:18

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
I'm starting to doubt myself...23 Sep 202500:45:31

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 issues

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
Listen to my call with Sam Ovens16 Sep 202501:37:43

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,Jonathan

P.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
56: Chapter 3 of this book will bend your mind!09 Sep 202500:35:57

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
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