Hey, Jai here.

This is my journal where I brain dump interesting things i’ve learnt or done recently.

You’re in the 0.5% of my audience that get to read this. Here’s the latest (<5 minute read):

I’m no longer making videos on Youtube.

For the last 9-ish months i’ve had my trusty german film maker Flizzy travelling with me on and off helping me document in public.

He flew out to Japan with us in feb for one last hoorah and we’re cooking up our last edits together.

Truthfully I haven’t been that inspired to create. Everywhere I look is the same old shit. More people starting communities, more people making youtube vlogs, more people running founder houses.

From a macro perspective, I think it’s dope…. these things are net positive for the world.

But from my own personal inspiration, it makes me want to draw back and chart a new course. To go left when everyone else is going right. I think that’s where true differentiation is born, and ‘competitors’ no longer exist.

I would rather create, than compete. The TLDR is that i’m pulling back from the usual ‘build in public’ once our last few videos go live this month. Once I figure out a new way to create that feels like play and not work, you’ll see more videos from me :)

In March I planned to fly from Japan to Argentina, but decided to stop in Hawaii to break up what would have been a 37 hour journey with 4 layovers (rip)

…and then I never left.

6 weeks solo (except for my brother Flynn coming to visit) in a lil beach shack on Oahu. Check it out on my insta.

When most people think of Hawaii they think of surfing, hiking & sunshine… at least I did before I arrived. Reality was more like 3 wild storms, days of power outages, severe flooding and a receding tan line.

Despite this it still felt like home.

I think it’s because Hawaii reminded me of a place I spent many impressionable years growing up on… the Cocos Islands. A paradise that’s also kind of a dump. Beautiful tropical beaches as far as the eye can see, right next to run down shacks and old rust buckets that vaguely resemble cars.

I like the small town feeling it brings. Makes me feel like i'm one of only a few people who've ever experienced it haha

In Hawaii I had a lot of time alone with my thoughts, and made some major progress in biz too. Here’s 3 big examples:

1. We spun out the Founder Sports Club into it’s own company and gave away equity for the first time ever. To an old friend and mentor, Max.
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   ​Interesting facts about Max:​
   - He wanted to acquire my first company Brand Boostr back in 2022, but I didn’t want to sell it (I should have)
   - He later sold his agency Megaphone Marketing for $20M and bought 10% of consulting.com from Sam Ovens (Iman Gadzhi then bought it last year)
   - He started an anti-acne pillow case brand after making 5 websites and attempting to sell different products via meta ads, then refunding all customers immediately. He wanted to know which products naturally had a higher CTR in ads and therefore more marketing potential. The pillow cases stuck and he spent a year developing the product before scaling it to $35M valuation in year 2. The market caught up and he ended up shutting it down.
   - He once had a youtube channel where he mastered a new skill every month. How to kickflip, play piano, speak a new language, etc.
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   You’re probably starting to see why we wanted him on our side, huh?
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   We’re at a stage of business where Evan and I are growing something beyond what we’ve ever done before. We’re essentially going in blind and hoping for the best. Our bet is that being willing to share some of the ownership with veterans will yield a much greater result, and then we all win in the process.
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   That’s the theory at least.
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   If i'm honest with myself, I've been feeling a little sheepish about the Founder Sports Club for a while now. Because it's just SO far from what I believe it can and will be. We're stripping everything back and building new. Listening to customers --> Improving product --> listening to customers --> improving product --> etc.
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   Big swings are needed, and now in motion. I’ll report back on progress in these journal entries.
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2. We hired COO’s for both WLTH WLKS and Founder Sports Club. Their names are Khaleelah and Sunil, and they were both running or previously sold companies for $20M+. Either we were very convincing, or they care deeply about our mission (hopefully the latter!)​
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   ​The vulnerable share here is that our companies probably aren’t in the position to afford senior roles like this, and we had to get creative to do it. But great companies are the sum of it’s people and we believe it’s putting trust in great people that will bring the growth and opportunities we’re looking for. Kinda like investing your life savings in Bitcoin in 2014.
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   In any case, it continues to free up Me & Evan's time to focus on speaking to our customers, making better products, and creating more content (like this journal entry).
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   What was really cool about this hiring process is seeing how powerful building in public has been for attracting great talent. Often these people had been watching me or Evan’s youtube videos since 2024, and finally decided it was the right time to explore a career alongside us. Talent acquisition might have the longest sales cycle ever, haha.
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   btw our process for promoting new roles is this: design a great job description/challenge and then share it via email and IG story once. That’s usually enough to uncover the calibre of talent I mentioned above.
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   That said, i admit we’re pretty privileged to be able to say this. Hiring usually sucks. It’s one of the most talked about topics in Art of Mondays.
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   …which brings me to update #3
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3. Max (mentioned above) owns a business that helps you find great overseas talent at a fraction of the cost. We partnered with him to create mondayhires.com for our community (and now, our internet friends like you as well).
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   ​I’m talkin’ video editors, VAs, engineers, strategists, media buyers, even folks in other languages like german, spanish etc.
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   We’re at capacity currently but will be opening up more spaces in the coming weeks. Drop your email on the waitlist if you wanna find out more. Very limited but worth a share anyway :)
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4. Bonus update because the rest were all business focused.
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   ​I’ve been dropping in at Crossfit while here in Hawaii and despite it costing me an arm and a leg for adhoc classes (like $50 AUD/session wtf), i’m lifting heavier and feeling fitter than I have for probably 2 years.
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   For the fitness nerds - i’m about 84kg and <10% bodyfat at 6”3. Crossfit gets a bad rap sometimes but i’ve found it to be the most enjoyable style of training for me. I get to feel like a fucking animal throwing weight around and feel genuinely exhausted and sweaty afterwards. Throw in a couple cans of LMNT salts and it’s a days job well done.

Random things that have given me great value lately:

1. I read this article by the founder of Superhuman on finding Product Market Fit and found it SO useful.
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   We used the same 4-question framework to survey our customers and uncovered holes I didn’t even know existed, like how we have several ICPs (Ideal Customer Profiles) that use our products, but 2 of them by FAR outweigh the others. They pay more, stay longer and cause less headaches. Now we know who to focus on and make bette products for :)
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   This article is like my bible now. If there’s one thing you take from this entry let it be this!
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2. ​The Fish That Ate The Whale. A book about the guy that influenced the banana trade and built an empire.
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   A really fascinating read because 1) I fucking love bananas and 2) business 200 years ago was weirdly similar to business today. So many micro lessons on consistency, positioning, and finding opportunities where nobody else is looking.
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   Did you know a banana is technically a berry (not a fruit) because a banana tree is actually a herb, not a tree? Crazy ahh fact if you ask me
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3. I gotta give a shoutout to the MFM podcast. Literally the only pod I listen to every episode of. Great storytelling, always tactical takeaways I can apply to life or business.

Big Idea:

If any of this journal entry has been useful to you, I have a small ask: I’m looking for a contact at Claude or OpenAI, or a similar AI company.

I want to land a partnership deal where we integrate their tool into our ecosystem (of 100,000+ entrepreneurs) and they pay us a monthly sum to do it. I believe the biggest risk to AI companies today is consumer loyalty. How many of you have ditched Chat to start using Claude recently??

I think we can add $$millions/yr to their bottom line, and I would love a warm introduction to someone that can make it happen. If that’s you, here’s an email you can send and loop me in. Thanks internet homies!

Subject line: Art of Mondays <> (their company)

“Hey (name),

Introduding you to Jai, the founder of Art of Mondays.

He runs a couple of entrepreneurial communities (100,000+ founders in their ecosystem). Many, if not all, are daily users of AI.

He’s interested in partnering with (name of company) to build in public using (name of their product). Are you the right person for him to speak to?

If you don’t want to, that’s cool too. I'll leave you two to chat.

(your name)”

If you put me in contact and the deal pulls through, i'll send you $5k AUD to say thanks xx

What’s next for me:

I always seem to write these entries from a plane. I guess i’m more reflective at 40,000 feet.

I’m leaving Hawaii, and pretty sad about it tbh. Feel really connected to the place and its people.

Onwards to Argentina, Paraguay and then Spain by the end of April. Will park up there in May for a couple of Residencies and a team High Leverage house.

June: Wide open

July: France for our first annual Camp Mondays event

Then, make some more dreams a reality I guess 😈

And finally, a thought to ponder.

I believe entrepreneurship is the greatest form of self improvement. It sets you on a path that forces curiosity, constant failure and learning new skills.

It’s why i’m so drawn to helping other people find their path and the freedom that comes as a result.

and why i’ll open an alternative school (or many schools) some day.

Growth doesn’t come from repeating what you’ve always done. Just like you don’t get bigger muscles without increasing the weight or reps.

Are you increasing the weight in your business (or life), or just doing the same shit expecting a different result?

Seeya when I have something worth saying.

Big love,
Jai
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PS. Sending love to the ppl of the North Shore who are still cleaning up after the floods <3

PPS. Byron Bay video (Flizzy's handiwork) just went live on Youtube. It seems YT doesn't like that i've been fairly quiet over there recently so any love you can throw it is appreciated 🙏

Journal Entry // April 17th, 2026