Hey friend,
So I decided to give my newsletter a name.
Welcome to the very first Timeless/ly Tuesday.
Let me explain.
First, I want you to know exactly what you can expect each week. I want you to have a reason to open my emails. I want there to be a little spark of excitement every time you see my name in your inbox because you know that you’re going to read something that will actually help you in your own creative company that you’re building. That’s my hope with this.
So I thought, what actually matters to creatives?
Timeless principles and Timely Strategies and Tactics.
Something that you can use forever, and something that you can use right now (hopefully).
Timeless/ly.
Oh, and Tuesday alliterates.
Enough exposition! Let’s get into our very first edition.
Timeless: Channel demand, don’t create it.
Have you ever tried to teach a 3 year old to read?
It’s tough.
I started the hard way: little crayons in the bubble bath, drawing an A on the side of the tub. Drawing letters on a page. We even tried painting the letters, thinking that the paint would make it more fun!
None of it really worked.
Then I realized Zion doesn’t care about learning to read. As a 3 year old, he doesn’t understand the value of it.
So I asked a different question. What does he care about?
The answer is simple: Zion loves cars.
In fact, he’s obsessed with them. He knows more models than me AND literally owns 200+ hot wheels and match box cars. He even started his own art business selling paintings to pay for more cars (it’s still in the startup phase).
So I started using cars to make the shapes of letters, and all of a sudden he was riveted.
Customers work the same way.
They’ve got their own thoughts and beliefs and lives going on in their heads, and they really don’t care what we have to say until it connects to something they already want.
Most of us try to create demand. We make what we love, post it, and hope strangers will come to want it. Then we wonder or complain about how long it’s taking to grow our instagrams.
The faster path is to find where the demand already exists. Where money is ALREADY BEING SPENT. Where there is a market. Where people gather. Where activity is already happening.
Just posting in that place doesn’t count, either. You have to find out where the demand is, then figure out what those people care about, the problems they have, the pains, the desires, then connect what you create to what they care about. That’s the secret sauce. Always lead with why they should care.
I know, this is easier said than done.
It’s why I think business and marketing is deeply empathetic. You have to spend a lot of time trying to understand who you’re trying to serve.
Here are some examples of how this works in art businesses: people already set money aside for weddings, funerals, retirements, a new baby, their pets, birthdays, anniversaries, gifts, moving, retirement, the list goes on.
They’re going to spend their money on that thing whether your painting is an option or not. That is a much easier sell than convincing someone who wasn’t planning on spending any money why your thing is valuable and worth more than the money you’re asking for.
If you love painting exotic animals, your best collector might be someone who owns one. (Any individual who owns a tiger is gonna be rich. Fact. And they probably live in Texas.) So when you’re making content, talk to the person who owns one. Or someone who secretly wants to own one but would never admit it to other people. Talk to the people who love going to zoos. Don’t worry about appealing to everyone, you can’t.
Talk about an interest that they have, some interesting thing that only people who spend a lot of time around tigers would know, or something that someone obsessed with tigers would appreciate. Then state that as the reason you paint tigers. You’ll get a lot more eyeballs on your content. That’s going where the demand is. Not just physically, but psychologically.
You can also physically go where demand is by finding the right show. Or being in the right gallery. Or presenting to the right business.
“Right” depends on who your product speaks to.
Demand already exists. Your job is to find out who already wants something you make, and where they’re spending money right now.
That’s exactly where I’m starting with Dimitra’s Print Club, because the people most likely to join are the ones who already love her art.
Timely: Growing Dimitra’s Print Club
It’s $15/month. Every month, members get a new 5x7 print and the Dreamers Collective, a super awesome 8-page newspaper we launched this summer, sent via snailmail.
Now that I’m done refilming the business section of the Mastery Program, I’m lazering in on Dimitra’s Print Club (in the spare 5-10 hours I have a week lol).
Whenever I’m going to improve something, the most important first step is to get an accurate picture of what REALITY is. Not what we feel, or hope. But the numbers and our confidence in the accuracy of those numbers.
Then, once we have an accurate picture of reality, we look for the constraint(s).
The things that are holding the business/product/project from achieving the goal.
So this week I traced every one of the 832 sign-ups since the club opened in August 2025 back to where it came from (Claude did most of the heavy lifting). Three things jumped out:
- Two thirds of the club joined in only 21 days(!!!) 568 of the 832 signups joined on the days the cart was open during our three 2025 launches when there was a small window that people could sign up each month. Very interesting…
- The best 4 days of 2026 wasn’t an ad. When Dimitra announced the new newspaper in July, 19 people joined in four days, about eight times her normal pace. Meanwhile we’ve spent $14,063 on Facebook and Instagram ads for the club in the last year, which works out to about $127 for every member they brought in. A member is worth roughly $146 to us (and counting). Quite a long time to wait for a $19 total return! Most of this was earlier on, I saw this trajectory months ago and cut the ads down dramatically so now we’re just retargeting people from the website. Since then we’re only spending around $20-60 per customer (depending on whether we’re using Meta’s attribution or ours). Worth it either way.
- We’re losing about 9% of members every month. Just holding steady takes about 40 new members a month.
And now something that I’m deeply ashamed of: the new welcome emails for members haven’t sent once since August 31. It’s completely my fault. I switched email platforms for Dimitra from Kit to Klaviyo and in my haste to finish stuff before our Italy trip, I didn’t double check that it was working. 🤦
None of the new members since then got the welcome emails because of a single filter setting. About 30% of new members are gone within their first two issues, which is what I was trying to improve when I made that sequence with her. 🙃
So here’s the plan:
- Fix the welcome, so every new member hears from Dimitra in those first weeks.
- Small, but important: Dunning. 39 members are paused because a card failed, and most of them joined in that first 2025 launch. A plain “update your card” note should bring some of them back. And I need to set an automation to fix this on an ongoing basis.
- Make every newspaper issue news. One post, one reminder and one email per issue, with some honest urgency: join by this date to get this issue.
- Give people a strong reason to join, probably in November around a newspaper issue we’ll do something that gives people a stronger reason to join (that will also benefit existing members), and invite the roughly 850 people who’ve bought Dimitra’s art but never joined. Still gotta work on what this will be exactly.
- Figure out the exact USP (unique selling proposition). Essentially, where is the demand that I can tap into and what do they care about? For Dimitra, this is best done through testing a lot of different angles through content bc she has 500k followers across platforms. This is the biggest lever. Once we find what works really well in terms of the messaging via IG and email, we need to stick with that and then we can test out ads to a cold audience again and scale profitably. Since we redesigned the page and launched the newspaper, the page converts at about 4%, which is AMAZING. We just need to get more of the right people to the page.
- Consider going back to a small sign up window each month…
To put it simply:
- Make it so that people stay longer and spend more
- Get more people.
Sounds so easy when I say it like that!
Our goal is to get to 1000 members. I was hoping to do so by the end of the year, but honestly, that won’t be possible unless we have a reel that goes viral promoting the print club. Obviously that would be amazing, but that’s hard to engineer. Building a system that predictably improves over time is something better to work towards, while still trying for the virality, of course! haha
That’s how I’ve built Milan Art. That’s how I’m gonna build Dimitra Milan Art. And that’s how I want to build Creative Company.
Timeless principles applied Timely:
- find the constraint
- double check work
- give people a reason to buy
- find out who the customers really are and why they should care.
A quick favor
This is the first Timeless/ly Tuesday (on a Thursday), and I want this to be really valuable to both of us. So if you read this far pretty please hit reply and tell me at least one word: shorter, longer or just right.
Rooting for you,
Jake
P.S. I listened to this song on repeat for the 3 hours or so that I worked on this. That helps me get into a flow state. It’s on my Focus playlist.