START HERE: 📍Substack Quest
The exact model I used to build a consistent $5k-$10k/month paid newsletter business with AI & Automations, on the side of my 9-5, working 2 hours a day. Updated July 2026.
The exact model I used to build a consistent $5k-$10k/month paid newsletter business with AI & Automations, on the side of my 9-5, working 2 hours a day.
Inside you get the strategies, the tactics, and all the tools.
What in the world is “SUBSTACK QUEST”?
Most people start with building an audience or writing content on Substack. I believe this is fundamentally wrong and that’s why most Substacks stay small. The QUEST has the right method of doing it.
I extracted the frameworks from my 15+ years of experience in product sales and marketing of paid membership in the big tech. I applied this to my newsletter, it worked, now I’m helping others replicate them - inside of the QUEST and with my coaching service.
The SUBSTACK QUEST is action-based training program designed to help you launch, grow, monetize, automate, and scale your newsletter. You’ll get access to strategies that big tech companies use and most writers don’t.
I add new content to the QUEST regularly.
It’s a living growth experience.
Here’s what Jennifer Dragonette said about the QUEST during our live:
Become a paid member to get a full access to the QUEST on Substack. Or get lifetime access to the FULL SUBSTACK QUEST on Teachable
You’ll earn back your investment with your first few paid subscribers!
What is Substack Quest?
This Quest has 7 STRATEGIC DOMAINS. Find the links below to each of them.
#1 Mindset of Achiever - The mindset which helped me build a 5-figure online business on the side in 11 months, and how to develop it. Table of contents:
#2 Positioning Strategy - It’s all about the niche, topic, audience, your content pillars and your unique angle - all the messy stuff most people can’t clearly define. When you nail that part down, everything becomes much easier. Table of contents:
#11 Competition
#3 Product Strategy - Build your irresistible paid offer - research, define, price, validate, present, and launch your Substack. This also includes setting-up your Substack for a high conversion rate, and scheduling your ongoing process of analysis and optimization. AI & Automations.
#1 Kick Off
#11 CASE STUDY: A walk-though my 10-Day Crash Course Freebie that doubled my paid subscribers growth
#13 BONUS: Your Substack Growth Game Plan & How to Set-up for High Conversion Rate
#4 Content Strategy - Define your content pillars, build your content funnel so you don’t burn yourself out trying to figure out what to offer next. Here I’ve prepared: a writing crash course, a copywriting crash course, a SEO crash course, repurposing, digital products, and more. AI & Automations.
#7 Repurposing vs. Repackaging and The ONLY Content Flywheel You Ever Need
#9 Your Content Strategy Map for Value Creation & Delivery Plan
#5 Growth Strategy - Launch your Substack, strategies to grow your free subscribers on autopilot. Use of external sources for growth. Mistakes to avoid. Analyze data and optimize for acquisition, conversion and retention. AI & Automations.
#1 Kick Off
#10 Growth Tactics Outside of Substack: Writing on Platforms like Medium, Using Social Media & Paid Ads
#6 Monetisation Strategy - Grow your paid subscribers, monetize your free subscribers, strategies to further monetize: cross-sell, and up-sell loyal buyers. Key KPIs to measure. Mistakes to avoid. Key strategies corporate companies use (and most writers don’t). AI & Automations.
#12 WORKSHOP: My exact System of how I launched an online business and grew it to >$5k/month using AI
#7 Retention Strategy - How to optimize for retention from day one (because after one year it’s already too late). Key KPIs to measure. Mistakes to avoid. Key strategies corporate companies use (and most writers don’t). AI & Automations.
#1 Kick Off: The Business Model No One Tells You, But Works for Corporates and Generates Billions
#2 Retention Tactics for Paid Newsletters Adapted from The Corporations
#3 Most Common Mistakes of Paid Newsletters that Keep Your Conversion & Retention Low
#8 The Complete Substack Blueprint - here we bring everything together into one single strategy for your newsletter.
#9 The QUEST LABS - the AI & Automations hands-on experience.
#1 Sell on autopilot - the Substack - Kit automation that brought me 100+ paid subscribers
#2 Workshop: Build a high converting sales sequence with ChatGPT
#3 Automatically Turn Every Substack Post into 3 Posts for X with AI Agents
#4 Create an AI Agent in Make.com to repurpose your Substack post into a viral-ready X post
#5 Automatically Repost Substack Notes to Other Social Platforms
#6 Automatically Repost Notes to X, BlueSky, LinkedIn and Threads
#7 Automatically Turn Notes into Carousels & Quote Images for Instagram, TikTok, LinkedIn and X
#8 Automatically Turn Substack Posts into Pins for Pinterest
#9 Automatically Share Your Substack Posts to Facebook, LinkedIn, X and BlueSky
#10 Turn Your Substack Notes into Images and Short Videos for Instagram, TikTok, YouTube & Pinterest
#11 How to create a talking head video using your AI avatar that looks, talks and moves like you
(coming soon) Turn AI into your strategy & implementation advisor (with my new AI trained on everything in the QUEST)
(coming soon) Create a professional-looking video course with AI without the need to record yourself talking in front of a camera.
(coming soon) Build a paid advertising funnel that feeds your growth beyond the limitations of organic content creation.
BONUS: The Unplugged TOOLBOX (coming soon)
Each domain of the program includes some or all of the following 5 QUEST ELEMENTS in a structured, combined step-by-step approach:
COURSE:
Multiple courses with recorded video training
Printable handout from the training, so you don’t have to take notes
Printable to-do check list that you need to implement
CHALLENGE:
Mini challenges within each Domain
Guided way to the Notes and Writing Challenges
Spotlight sessions for the most active members in the Challenges
COMMUNITY:
Accountability progress tracking
Celebrating milestones with special awards
Dedicated community chats for people in the Quest
EXPERIENCE:
VIP Only: Submit to me for review every step you complete
VIP Only: Two reviews of your Substack per year: 1 video & 1 text review
1:1 private chat with me about anything on the Quest or Substack
1:1 private strategy calls with me in the right moment of your journey
Paid members: 1 x 30 min call per year
VIP members: 1 x 30 min + 1 x 60 min call (can be 3 x 30 min) per year
Opportunity to use 50% off of my brand new 1:1 private personalized coaching program built on the Quest workflow. Because strategy is only 20% of the work, the rest is excellence in execution, and that’s where I’m nailing it (based on my 15+ years of being an over achiever in product development, marketing, and sales of subscription-based services)
BONUSES:
The Unplugged TOOLBOX - The Quest WORKBOOK with all handouts, the Quest Handout eBOOK with all trainings, a set of all of my custom GPTs, my Claude skills, including my personal Claude skills I use and my SOPs I use to grow (only available in the Toolbox), tools, courses, templates, formulas, cheatsheets, checklists, handouts and systems I use in my daily work to speed up, organize and stay efficient. I constantly add new GPTs, Claude skills and tools to the library.
BONUS Courses and TRAININGs:
Writing, Copywriting, SEO and AI SEO, Storytelling and much more
AI Use cases and best AI tools for every Quest domain and every content format - text, audio, video
Prompts, templates that help you implement AI on every step of the way
Workflows I use to speed up my daily content creation in any format
VIP Only: How to create your own custom GPT, Claude skills + templates
VIP Only: Behind the scenes video with a sneak peek of the settings of my most popular custom GPTs
CASE STUDIES & WORKSHOPS (I leave nothing behind), some of which are:
My exact System of how I launched an online business and grew it to >$5k/month working just 2 hours per day, on the side, without any writing experience, fancy guru knowledge or upfront cash investment - just me and my professional background (can be applied on any platform online).
My Substack-Kit Automation Funnel that helps me keep a 6.5% conversion rate of my paid newsletter with zero effort. Includes a Kit automation template so you can easily implement
My exact System on Doubling New Subscribers Growth Without Going Viral
Automate Social Media Content Creation and Posting
My paid ads funnel I use to scale to $20k/month
Go Viral on Substack Notes and Gain Hundreds of New Subscribers
and more → find them in each domain
After completing this Quest, you will:
Have clarity about your strategy and the tactics
Have the tools, workflows, and systems to implement them
Have gained the confidence that you know what you’re doing on Substack
And if you have implemented everything consistently, within 6-12 months you should see tangible results:
Have at least 1000 monetizable subscribers
Have earned your first couple of hundred dollars
Have a growing conversion rate, approaching or (why not even) exceeding 5%.
“If you want to monetize your writing, I highly recommend joining Yana’s paid tier. It’s 100% worth it.” — Jari Roomer, Write • Build • Scale
How long will the full Quest take to complete?
It will roughly take you about 6 months to gain enough confidence that you know what you’re doing on Substack.
But Substack is a long game. You might need to revisit it along the way on your Substack journey.
It’s all about doing the things. Test, evaluate, adapt. That’s how you find your best way to grow on Substack.
Who Is This Quest For?
Every writer who takes their writing as a business must have a newsletter and Substack is THE place to be right now, so I won’t go into convincing you this is right.
Take this Quest ONLY if you’re confident the above is true.
If you’re NOT SURE Substack is worth the effort, take this FREE Substack course first.
This Quest is for you, if you’re:
New to Substack, just starting a newsletter and don’t know where to begin. Fiction or non-fiction - this quest will help in both (you won’t find that anywhere else)
Already running a newsletter, and:
struggling to grow your free subscribers consistently
considering opening payments, and start monetizing with paid subscriptions
have payments enabled, but feel stuck growing your paid subscribers consistently
Already growing pretty well, but you still need to:
become a Substack bestseller, or
optimize your conversion rates
This is a beginner-friendly advanced program.
How Did this Quest Come to Life?
Following the high demand in the Unplugged Community I started working on this project a while ago.
I wanted it to be different. To not fall into the traps of courses, coaching programs, and other popular formats in the creator industry. So it took me a while.
But now it’s ready.
It’s the cornerstone of the Unplugged publication and the core of my entire online business. It’s a one-stop-shop for a newsletter business growth.
Become a paid member to get a full access to the QUEST on Substack. Or get lifetime access to the FULL SUBSTACK QUEST on Teachable
You’ll earn back your investment with your first few paid subscribers!
Why trust me?
I won’t show all the you certificates and awards or list polished achievements that mean nothing to you (although I have them).
I’m a data-driven result-oriented person, so I’ll list only facts I can prove:
I’ve become a Substack Bestseller in 3 months after I started implementing my strategy consistently
I’ve reached a conversion rate of 6.5% and growing
I’ve built a six-figure online business on the side of my 9-5, working just 2 hours/day
People who actively use my tools have their Notes go viral, gaining hundreds of new subscribers
Most committed paid and VIP members experience paid subscribers growth, some even in the first month after joining.
My coaching clients achieve amazing results following my QUEST methods:
My methods work, here’s the proof:
You think I did all that using my 15+ years of knowledge and experience leading strategic product development & sales teams in a big tech selling subscription-based services.
You’re right.
But it’s not only my experience or the expertise I have. There are many people with a similar background like me, who try and fail at this. It’s the mindset.
That’s why I start with this in the Quest.
The Quest, how much?
Oh, that part…I’m not gonna ask you to pay on top of what you already pay, because I don’t believe in that approach - you will learn in the Quest why, so…
It’s already part of the Unplugged Paid Membership in two flavors:
Substack Quest - for all paid members
Substack Quest VIP Experience - for VIP members
Get Early Access to the whole QUEST while I’m building it. You’ll earn back your investment within 3-6 months.
Where can you access the Quest?
Use the links from the curriculum described above. Or start below and follow the path - each post links to the next, just like a Quest:
Will the Quest be updated?
YES! Regularly!
And NOT ONLY!
I will add to the Quest new content regularly. It’s a kind of a living growth experience.
You’ll be informed about any new additions or updates.
When does the Quest start?
It’s an on-demand experience. Take it when you’re ready. All paid members have access to it - you can start it whenever you’re ready.
It’s a Quest, meaning it’s structured in a step-by-step basis. First domain comes in the following days, and you have about a week to contemplate on it and implement whatever changes are necessary from you to make.
Once completed, you’ll have access for as long as you keep your paid subscription. It is an on-demand Quest, you can take it at your own pace.
Ready for the Quest?
Here’s the kick-off:
Stay Unplugged!
I see you inside!
Yana
P.S. For this Quest I’ve made myself available for 3 to 6 people (and that’s almost filled) who are serious about Substack and want to work 1:1 with me to accelerate growth. Learn more here.
This looks amazing, Yana! I don't know how you have time to do everything you do.
Highly recommend this Quest, especially as a VIP MEMBER. Her Substack education value more than pays for VIP. Less than that you won’t get everything you need to know. It’s nice to get her updated tools and perks without wondering about upgrading. Yana updates her quest regularly for paid and vip members. And her Ai quest- genius. Saves me hours in editing and content creation with Ai software tools. Love how she’s available with her 30 min 1:1s as well! Shes very honest and helpful. Her platform on substack is simply and all in one space for today’s new internet to stay ahead and not get left behind. -Liselle Kiss American Designer