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, Ja...
Mar 04, 2025•48 min•Transcript available on Metacast 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
Feb 26, 2025•22 min•Transcript available on Metacast 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 howtobusiness.substack.com
Jan 11, 2025•39 min•Transcript available on Metacast 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 howtobusiness.substack.com...
Oct 11, 2024•52 min•Transcript available on Metacast 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 howtobusiness.substack.com
Aug 15, 2024•1 hr 4 min•Transcript available on Metacast 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 howtobusiness.substack.com...
Jun 04, 2024•10 min•Transcript available on Metacast 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 howtobusiness.substack.com...
May 28, 2024•20 min•Transcript available on Metacast 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 howtobusiness.substack.com...
May 23, 2024•9 min•Transcript available on Metacast 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 howtobusiness.substack.com...
May 21, 2024•1 hr 6 min•Transcript available on Metacast 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 howtobusiness.substack.com...
May 16, 2024•5 min•Transcript available on Metacast 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 howtobusiness.substack.com...
May 14, 2024•57 min•Transcript available on Metacast 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! Y...
May 09, 2024•11 min•Transcript available on Metacast 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 howtobusiness.substack.com...
May 07, 2024•38 min•Transcript available on Metacast 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 ...
May 02, 2024•10 min•Transcript available on Metacast 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...
Apr 30, 2024•45 min•Transcript available on Metacast 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 kno...
Apr 25, 2024•14 min•Transcript available on Metacast 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 ...
Apr 23, 2024•27 min•Transcript available on Metacast 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 bon...
Apr 16, 2024•32 min•Transcript available on Metacast 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...
Apr 09, 2024•33 min•Transcript available on Metacast 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 episode...
Apr 03, 2024•24 min•Transcript available on Metacast 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 t...
Mar 25, 2024•34 min•Transcript available on Metacast 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 howtobusiness.substa...
Mar 13, 2024•8 min•Transcript available on Metacast 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 howtobusiness.substack.com...
Feb 20, 2024•36 min•Transcript available on Metacast 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 howtobusiness.substack.com...
Feb 06, 2024•15 min•Transcript available on Metacast 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 howtobusiness.substack.com...
Jan 30, 2024•20 min•Transcript available on Metacast 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 howtobusiness.substack.com...
Jan 05, 2024•1 hr•Transcript available on Metacast 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 acc...
Dec 22, 2023•49 min•Transcript available on Metacast 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 howtobusiness.substack.com
Mar 02, 2023•35 min•Transcript available on Metacast 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 howtobusiness.substack.com...
Feb 23, 2023•1 hr•Transcript available on Metacast 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 howtobusiness.substack.com
Feb 15, 2023•54 min•Transcript available on Metacast 
