This was our first monthly live Q&A and it was amazing! Thank you all for joining and bringing your questions - pricing, positioning, automations, podcasts, the new FreeWall feature, growing on Substack as a one-person business… we covered a lot in 80 minutes.
🔥 LIVE Workshop for Unplugged Paid Members 🔥
On 26th of November Devon and I will co-host a live workshop where he’ll share how he grew with 4k subscribers, 67 paid and 7k in ARR in just 30 days. Save the date here:
Here’s every question asked on the call and a short version of my answer, so you can jump straight to the part you need in the recording.
Substack pricing and positioning questions
How long until I know my positioning is working?
Engagement should lift immediately. My growth thresholds: ~300 free subscribers per month, at least 10 per day as a direction. If your free-to-paid conversion is below 3% and not growing by month three, it’s a positioning problem, or maybe, a messaging problem. You might have the best offer there is but if your messaging is off, it won’t work - for free subscribers growth and paid too. Your offer has to be clearly described - must leave zero room for interpretation. Make it clear. In the QUEST LIVEs I’m talking a lot how to optimize Substack for growth.
I want to shift my positioning - do I announce it to existing subscribers?
If you’re only adding benefits, just add them and announce it to your entire list, not only paid. If you’re also raising prices, run a 1–2 week promotion first: everyone who upgrades locks the current price and gets all the new benefits. I did this twice - the August one brought me 202 paid subscribers and the orange bestseller badge. I shared a case study about this campaign in a Monetization Masterclass I had with Kristina God.
How do I know my paid membership description communicates the benefits correctly?
Why is your monthly price almost the same as your annual?
How to grow on Substack
What’s a realistic posting frequency for a one-person business?
I post 10 Notes a day, but 3 per day is more than enough to start with. Use the Viral Notes Writer Skill or custom GPT to make sure they bring subscribers - it’s in the Unplugged Toolbox. For posts: I think two per week is optimal - one free, one paid.
How do I turn followers into subscribers?
Should I put links inside Notes?
They don’t get much traction for me (except when I restack posts). Better: introduce the thing in the Note, invite people to DM you, or drop the link in the first comment - classic social media tactics. Conversation starters work best for me. Use the Viral Notes Writer Skill or custom GPT to make sure you use the right format for a conversation starter - it’s in the Unplugged Toolbox. Also here are five free Notes templates that bring subscribers:
Where do I share my posts and notes to get seen in this community?
In the growth challenges on my website - look for the pinned “share your posts here” and “share your notes here” posts and drop your links in the comments, not in the group chat.
How do I find an accountability buddy for the QUEST?
Post a short intro in the group chat and say you’re looking for a sparring partner — someone who not only keeps you accountable but challenges your assumptions.
🔥 LIVE Workshop for Unplugged Paid Members 🔥
On 26th of November Devon and I will co-host a live workshop where he’ll share how he grew with 4k subscribers, 67 paid and 7k in ARR in just 30 days. Save the date here:
Substack monetization questions
Should I break my $997 course into my paid subscription?
I do it with the Quest and there are pros and cons to that.
Pros: it massively increases the perceived value of your membership, and you never run out of content ideas, and paid posts become easy upgrade paths.
Cons: the publication date is visible (older content loses conversion power even when it’s still valid), and you cap the price - people won’t pay $500+ upfront for a membership.
I tried selling my Quest through an email funnel to free subscribers and it flopped - I got 3 sales from 6,000 subscribers. Epic fail. Now the Quest core sits in the paid tier and the LIVES in the VIP membership — so my founding members get everything included, no upsells on top.
Should I promote my course or the membership as a whole?
Yes, but not directly. Sell the main problem your paid subscription solves, then the secondary ones. In every piece of content you create and also your nurture emails: here’s how to solve your problem — and the content behind the link is paid. In sales emails: this is what you get, the problem it solves, proof it works, the price, and why now. In this mini course I cover exactly how to make your content sell for you:
I have no testimonials yet. What do I use?
How do I attract coaching clients when I’m just starting?
I don’t know what to offer paid subscribers - my lead magnet leads to a 3-month 1:1 program.
Create the do-it-yourself version of the same problem: a digital product or course inside the membership. You can also solve connected problems you solve in your 1:1 by writing about them behind the paywall. In the QUEST Product strategy I go deep into this in the QUEST and here’s the summary of it from the first QUETS LIVE
Email marketing and automation questions
How is your Kit welcome sequence structured?
25 emails: 10 nurturing (longer, educational, with links to my paid content), 10 pure sales emails, and 5 follow-ups for people who clicked but didn’t buy. Kit tracks it all automatically - this isn’t possible natively on Substack. Here’s how to build yours:
Can I build funnel automations inside Substack?
Bestsellers get native automations, but they’re basic: trigger → delay → email, repeat. Workaround until Substack rolls it out to everyone: give admin access to a bestseller you trust and the features unlock. I wrote about this here:
Does the Substack-to-Kit automation require Gmail?
No - Make.com works with any email provider that it supports, including iCloud. Gmail is just what I use (and it now works with personal accounts, not only business ones). Here’s how I set mine:
Does Zapier also work for sending subscribers from Substack to Kit?
Yes, it works well, I just prefer Make because Zapier used to give me a lot of errors.
🔥 LIVE Workshop for Unplugged Paid Members 🔥
On 26th of November Devon and I will co-host a live workshop where he’ll share how he grew with 4k subscribers, 67 paid and 7k in ARR in just 30 days. Save the date here:
Substack features and setup questions
How do I make my homepage look like a magazine?
Dashboard → settings → website → choose custom design → select magazine. It’s simply a different layout for your Substack website - which is a full-fledged website now. I have a very detailed guide about how to design your Substack in the Quest Lives here:
Where do I learn the technical setup - banners, images, design?
I intentionally don’t record how-to videos because Substack changes every month. That’s exactly what the Quest Lives are for: two hours every week, hands-on, settings included. We go live every quarter and recordings available to VIP members.
Can I paywall videos? And what about the new FreeWall?
What about podcasts - do they convert?
I can only speak for video: it converts well for me, because seeing your face is the fastest way to build trust. Substack doesn’t clearly attribute podcast sources in post stats, but either way it’s worth doing.
Can I reply to member questions with voice notes instead of a live call?
Substack has no native voice note feature, but yes - you can collect questions in the chat, then answer with a short Loom-style recording or voice text. It works. Just be careful with formatting a voice text because long blocks of text are hard to read.
Why to choose Substack over Skool?
Should I mirror my Substack on my website (or GoHighLevel)?
Alright, that’s the majority of the question and there are some more in the video. See you on the next live, same time next month.
If your question didn’t make the call, drop it in the chat or book me for a strategy call.
I see you in the next one!
Yana
P.S. Join me on the next Monthly Q&A in November:
