Following the amazing post I published last week, me and Timo went live for almost an hour.
I completely lost track of time. That doesn’t happen often.
I was joined by Timo a creator who grew on Twitter/X before switching to Substack, and has a very refreshingly contrarian take on the whole “engagement strategy” advice that’s floating around the creator space.
We covered a lot. So I’m doing something I don’t often do: writing a proper recap.
Here’s what we talked about.
Substack is not like any other social media. And that’s actually the point.
Timo said something early on that I keep coming back to.
On Twitter/X, when he was just starting out, he’d send DMs to other creators. Maybe three or four out of ten would reply. And even then, it depended a lot on whether you had status: followers, verified badge, something that signalled status.
On Substack? He said everybody replied. Even the big names.
I believe him. Because I’ve experienced the same thing.
It’s not that Substack people are nicer. It’s that the platform itself is built differently. There’s no follower count on your profile that tells someone whether you’re worth a conversation. There’s just your writing, your notes, and whether what you say resonates.
And because we’re all essentially running email lists, there’s a natural incentive to help each other. You can appear in someone else’s inbox through a collaboration. That’s a lever that doesn’t really exist anywhere else.
The engagement myth nobody admits
Ok, here’s where it got interesting.
Timo came in with a take I wasn’t expecting: he doesn’t recommend the “comment on notes to grow” strategy. At least not for people who have a 9-to-5 and limited time.
It’s not how I understand growth on Substack, but he has a point.
If you’re commenting just to be seen, it becomes a procrastination task. You’re not doing it because you have something to say. You’re doing it because you’ve been told it’s how you grow. And then it stops feeling like connection and starts feeling like a chore.
I agree with a version of this.
Because what works (what actually drives subscriptions) is when you leave a comment because you genuinely had a thought. When you restack something because it was actually worth sharing, not because you’re hoping for a restack back.
You know me, I lean on data. And what I’ve seen in my own numbers is this: every time I answer comments on my own Notes, even when the person isn’t asking me anything, even when it’s just an exchange of a few sentences, there’s a spike in new subscribers.
Not huge. But consistent. Every single time.
It’s not the commenting strategy that works. It’s the actual conversation.
The funniest engagement fail EVER
Someone once commented on one of my notes with: “Sub to me, bitch.”
Yes. Exactly that.
I clicked on their profile out of pure curiosity. And the same energy was across everything they’d posted. So I just thought, ok, that’s just who this person is.
Didn’t subscribe. Obviously.
But Timo made a good point about this. The comment was strange enough to make me click. Standing out worked. What didn’t work was having nothing behind it.
If you’re going to be loud, at least be loud about something real.
Lives: the underrated growth lever on Substack
Timo has done almost all of his lives with other creators. He said this is his actual workflow:
Reach out to someone.
Do a collaboration post or guest post.
Then the live is the natural next step of that relationship.
I love this because it’s actually sustainable. You’re not manufacturing content for the sake of it. You’re deepening a connection that already exists and creating something neither of you could do alone.
From my side, lives have been more spontaneous. Some are tied to promotional moments - if I’m launching something or supporting an affiliate partner. Some are spotlights for the most consistent people in my writing challenges. And some just happen because I get excited about something and want to talk about it.
What’s important is this: I once got about 20 new subscribers from a single live.
That’s real. That’s not hypothetical growth advice. That’s what happens when you show up live with someone who has an overlapping audience.
Do the work first. Then network.
This was probably my favorite part of the conversation.
Timo’s philosophy (and I share it) is that random networking is mostly procrastination.
He had a thread go viral on Twitter/X once. 5.5 million views. (It was about the mafia in Bali. I’m genuinely curious about that story for another time.)
And here’s what happened: he didn’t have to DM anybody after that. People came to him. Sponsorship opportunities. Fellow creators wanting to connect. It all just arrived.
His takeaway? Good work is the best networking strategy. Reach out only to people where there’s a clear, direct reason to connect. People in a similar niche. People you can actually help, and who can help you back.
I’ve said something similar in my work before.
Substack makes this easier than most platforms because the collaboration tools actually reward it - restacks, guest posts, Notes reposts. When you do show up for someone else’s audience, they actually see you.
That’s a different game.
Kit vs. Substack: the honest breakdown.
I run a daily curation newsletter on Kit. Three links, under a minute to read, high engagement rates. I started it before Substack even existed for me.
So why do I keep it on Kit instead of moving to Substack?
Three things, basically.
First, segmentation. On Kit, I can tag subscribers and send different links to different segments. If I’m pushing an affiliate offer that’s only relevant to part of his audience, I can exclude the others. On Substack, that’s not really possible.
Second, data. I can see which specific links got clicked, at the individual email level. That tells me what his audience actually wants to read, which makes curation better over time.
Third, design and control. Kit just gives more options if you care about that sort of thing.
But Kit costs money. Hundreds per month once you’re using the full feature set. Substack is free. And Substack’s organic discoverability is significantly higher.
We agreed on a recommendation for someone starting out: Substack. If you’re below 1,000 subscribers, the growth engine is worth more than the feature set.
My principle is similar but for email marketing platforms in general. If you’re below $1K in revenue, stay free. Then think about scaling.
Substack’s automated sequences
Something came up in the conversation that I want to be transparent about.
Substack is rolling out drip campaigns - welcome sequences, win-back sequences, free-to-paid nurturing sequences. This is a big deal for anyone who’s been wanting that Kit-style automation inside Substack.
I wrote about this here:
But right now? It’s a Bestseller-only feature. And very limited - no tags, no actions, no flows…
I’ve been testing it. And I’ve also been giving them feedback on it. Because while it’s a great step, it’s still way too limited for me to switch from Kit.
On Kit, when someone upgrades from free to paid, they’re automatically removed from the upgrade sequence. So I’m not sending “become a paid subscriber” emails to someone who already is one. On Substack, that kind of conditional logic doesn’t exist yet.
And I’m obsessed with subscriber experience. Sending someone a conversion email after they’ve already converted is exactly the kind of thing that I want to avoid.
So yes, the features are coming. And yes, I think they’ll eventually be available to all writers. But if customer experience and segmentation matter to you, Kit is still ahead, for now.
The Stripe problem. And why it matters more than people realize.
One of the audience members brought this up, and I agreed immediately.
Stripe (which is Substack’s only payment processor right now) isn’t available in every country. There are readers who genuinely want to pay for your newsletter but can’t. India came up specifically in the chat.
And if you’re a creator in a country where Stripe isn’t enabled, you can’t monetize on Substack directly at all.
This is a real gap. I’ve pushed for PayPal as an alternative. I’ve also pushed for one-time payments, as not everyone wants a subscription model, and if we could sell lifetime access or digital products directly on Substack, that changes the economics significantly.
Until then, Gumroad integrates well. And I’ll tell you exactly why in a second.
The real math on Substack income.
I said something on the live that I’ll repeat here because I think it surprises people every time.
Less than 30% of what I make on Substack comes from paid subscriptions.
The rest is digital products, high-ticket services, affiliates, sponsorships, and collaborations.
This matters because a lot of people think that if they can’t turn on paid or can’t hit their subscriber targets, they’re stuck. They’re not.
My Gumroad approach: I launched free products with bump offers and upsells in the checkout flow. The freebie generates traffic from Gumroad’s own marketplace — that’s the one place where “sales on autopilot” is actually true. And some percentage of those freebie downloads convert to paid products.
Timo’s rule of thumb: if you’re under $1K in revenue, use Gumroad. After that, consider something like ThriveCart — one-time fee, 3% transaction cut, no monthly cost eating into your margins.
The principle across all of this is simple. You write the content. You link to the product. You let the tools do the rest.
The TLDR, if you want it.
So what’s the actual takeaway from an hour of conversation?
Engagement works when it’s real. When you’re commenting because you have something to say, not because you’re farming subscribers. When you’re doing lives because you have a relationship worth showing on screen, not because you’re checking a content box.
Substack is a community in a way other platforms like Medium aren’t. But you have to treat it like one.
Do the work. Connect with purpose. Let the platform tools amplify it.
And don’t let the absence of one feature — Stripe availability, Kit-level automation, one-time payments — convince you that you have no options. You always have options.
Yana
P.S. Big thank you to Timo Mason🤠 for being such a great conversation partner. If you want to check out his work, find him on Substack: he’s building something really interesting.
👉 Start a discussion in the Unplugged community! Get help or simply introduce yourself and connect with like-minded members, and create meaningful connections.
Kickstart Your Substack Growth:
Get a FREE 10-Day Substack crash course to grow your first 1000 subscribers
Join my free Masterclass on how to start making consistent $5,000/month with AI
Join the One and Only Substack Quest to build a high-converting Substack
Work with me to get your Substack up and growing
Save Tons of Time! Use My Custom GPTs:
The Title Generator that gives me headlines that stop the scroll
The Notes Writer that writes Viral Notes, bringing me hundreds of subs
The Writer Pro that turns my Notes into >90% human drafts (here’s the free version).
Or get the bundle with all the tools, now at a very special price ;)
Become an Affiliate:
Earn 30% from each sale. Apply here (I approve everyone).
My Newsletters:
FREE Daily BiTES: A daily mail with just 3 bullets from the most helpful things I read about writing and making money online with AI
Have a GUT Time: A weekly short but powerful technique to build a growth mindset and achieve anything you want
Unplugged: The place to be if you want to grow an AI-powered paid newsletter and create content that sells itself.
Become a sponsor:
Reach thousands of engaged buyers.
