Hey friend,
Last week I asked for your thoughts on the length of the first Timeless/ly Tuesday email, and here’s what you said:

44 of you wrote back on my very first issue, which blew me away. I replied to every single one of you, too.
So I’m gonna try to keep this a bit shorter, but without sacrificing depth.
Shorter preamble should do the trick!
Timeless: People buy at the point of greatest need
You run a creative business, so your to-do list probably looks like mine: post more reels, fix the website, answer DMs, redo the pricing, start a newsletter, plan the series launch, what about black friday?
Every item feels urgent.
And they also all feel important!
So you do as much as you can and hope for better results.
Last week, I started reading The Power of Moments by Chip Heath and Dan Heath Elli’s suggestion.
Wow, what a great book (so far).
It’s all about how to create more impactful moments in your business and life.
It reminded me of one of the most important principles in sales and marketing, which connects to last week’s newsletter:
People are most likely to buy at the moment of greatest NEED.
Most of the time, I try to fix every part of a business. In reality, only a handful of moments really matter. Not every minute someone spends watching a YouTube video matters. Not every reel, not every newsletter.
So how do you find the moments that matter?
Chip and Dan say to look in 3 places:
- Transitions. A first day, a new start, a new member joining. Last week I told you the welcome emails for Dimitra’s Print Club (her $15 a month print membership) weren’t going out. Those first weeks are a transition, and it’s when about 30% of new members were canceling. Yikes! (fixed now, btw)
- Milestones. Finishing something, hitting a number, a graduation. For a collector, their first year with your painting on their wall. For an artist, your 10th sale. Some sort of psychological threshold that’s crossed.
- Pits. When something goes wrong. A card fails, a painting gets damaged in shipping, a print never shows up. Their advice is to fill the pits first, then build the peaks (the moments people remember because they’re way better than normal).
If I had to rank them on what to focus on it’d look like this:
- Pits
- Transitions
- Milestones
Pits are where the need of the customer is greatest. That’s where people tend to buy. Transitions are important because they make people ask “What now?” Milestones are really improtant once you have customers because it says “look how far you’ve come” making you focus on keeping them around, and ultimately getting them to buy more.
Start with Pits. Find them, then fill them. Then make the moment the fill it (with what you’re offering) a Transition. Then celebrate them with Milestones.
You might be thinking, how do I fill Pits?
Here’s what I recommend:
- List out potential problems or ask people who’ve already bought. What problems did they have. Problems disguise themselves in different ways, like annoyances, or frustrations. It’s usually the root reason or catalyst for why a person makes a change. THEN:
- Find the need. Go to people who already know they have a problem. They’re already shopping, so it’s easier to sell to these people but there’s usually more competition in selling to these people because it’s easier to find them. Unless you have your own list.
Example: about 850 people have bought Dimitra’s art but never joined her Print Club. WOAH. They already love her art on their walls, so it’s an easy invite. (doing this this week, along with another announcement)
- Help them realize the need. Show people a problem they didn’t know they had. Way less competition. Because it’s harder. You have to teach/inform before you can sell.
Example: most people don’t think “I need a newspaper from an artist.” HA! They think “gosh, I’m tired of wasting my time scrolling”, or “I’m spending too much time on my screen, but where else am I going to find inspiration?” and then instead of starting a reel like “Hey I’m doing a newspaper, you’ll love it! Go to the link in my bio to buy it.” we start the reel like “I was so tired of wasting my time scrolling, but honestly, I missed the inspiration that I found occasionally. So I made this newspaper. It’s a curation of beautiful creative work from artists around the world.” Much better reel/ad, right?
Last week we talked about going where demand already exists. This week is about timing that. The magic of content is that if we position our hook right, instagram finds the people who are at that moment. We just have to write the words and film the video that helps instagram match that content with the right person. They’re already out there!
Timeless takeaway: find the moments that matter most (transitions, milestones and pits), and make those great before you polish anything else in your business. Start with filling pits, then focus on transitions and milestones.
Timely: Turnaround reels really do work
I convinced Dimitra to do more turnaround reels because they work and they’re simple.
But here’s what works better: giving people a reason to stick around.
If you’ve never seen a turnaround reel before, click here.
Last week we did two turnaround reels for Dimitra.

If I’m being completely honest, I thought they were going to do better.
So I’m gonna try to understand why one did better and what they both can do better so that we can learn together!
Here’s what the numbers said:
The 90k one:

(bonus: with the 90k reel, we got over 20 new email subscribers on a WAITLIST for the print launch, and over 30 people in total. Probably will be worth at least $5000-$10000 if we nurture well)
The 33k one:

Observations:
- Almost identical rate: skip, share
- Same rate: likes, saves, reposts, comments
So does a 1% skip and .1% share rate really earn 3x the amount of views?
Maybe. But I think it has to do with something in the summary screenshot. I think the reason one got 3x the views is really because of the average watch time. If a viewer watches longer, they probably have a higher satisfaction and are less likely to exit the app, therefore earning Meta more advertising money. So Meta would then show that first reel to more people because it earn more money from that reel.
To put it simply: the longer reel held people better.
But why?
I think there are two reasons:
- The grand reveal: she’s turning around this huge wall, and we double hook with the text on screen (“It took me 80+ hours” and then again tell them “It’s $47,000” creating even more curiosity).
- The environment. We filmed it in our gallery. Less artists have access to filming in a gallery, so this creates almost instant credibility and therefore a stronger reason to watch. It gives visual proof that the $47,000 isn’t just a made up price tag, it’s legit going to sell for $47,000.
BONUS: when sharing this insight with Dimitra, she commented “Plus, there are multiple paintings, so people stick around to see the whole collection.” Absolutely right.
I believe the 33k reel painting has the potential to reach even more people because I think the concept is more unique, but this just goes to show you how important the packaging (how you position something).
I really thought “sculpture + painting” was going to perform better because of the curiosity, but that’s marketing for ya!
All of this brings us back to the book. The Heath brothers talk about the peak-end rule: people remember the best moment and the ending, and forget most of the middle. A reel with a big reveal at the end gives them both at once.
This won’t be the last time we try these. I have other ideas.
Timely tip: before you post your next reel, ask yourself one question. Why would someone watch to the very last second?
Rooting for you,
Jake
P.S. Many of you have asked me about my music and encouraged me to pursue it for myself. I started taking a course recently and we’re building out 4 full songs together alongside the instructors, then making one song on our own. I’m about halfway through the first song. Super excited to share progress on my own music. I’ll probably do that in the P.S.s until I start building marketing around my own music.
P.P.S Would you rate this email for me? Click here