How Do the Mighty BOOST Options Work on Substack, and How Can I Supplement It With Community Power?
Dear beta readers,
Thank you for your valuable feedback on the previous seven chapters, which is helping me refine this book and enhance it as a valuable resource for fellow writers. I have covered seven critical aspects that have helped many readers jumpstart their Substack journey. Receiving gratitude messages daily warms my heart and inspires me to make this book a valuable knowledge source for the community.
As I mentioned in the purpose of this new book, I am not here to tell you what to do and how you do it. Instead, I discuss what has worked for me, what successful people have done, and why some failed quickly. I hope you can draw inspiration from these examples to craft a strategy and plan that aligns with your goals, needs, and aspirations.
What follows is a summary of how I approach growing my audience, meeting their needs, and maintaining a sustainable writing business. We are all unique, and what works for me may not work for everyone. However, proven principles and values can be thoughtfully adapted to fit many situations.
Please remember to leave feedback on this post if possible, as the purpose of sharing this book on this platform is to refine the final version of the book to make it a relatable and valuable knowledge source.
Links to Available Chapters of Substack Mastery Book
Preface of “Substack Mastery” for Beta Readers, Chapter 1, Chapter 2, Chapter 3, Chapter 4, Chapter 5, Chapter 6, Chapter 7, Chapter 8, Chapter 9, Chapter 10, Chapter 11, Chapter 12, Chapter 13, Chapter 14, Chapter 15, Chapter 16, Chapter 17, Chapter 18, Chapter 19…
For those interested in taking their Substack to another level, here is a link where you can buy the Substack Mastery book through multiple online bookstores globally:
Some readers asked whether there was any discounted price for this book. One of my publishers, Smashwords, offered 25% discounts until 31 December 2024.
The funds generated from this book will be donated to the management of the Substack Mastery site for the ILLUMINATION community. This education site also amplifies the newsletters of freelance writers.
Please remember to leave feedback if possible, as the purpose of sharing this book on this platform is to refine the final version of the book to make it a valuable knowledge source. I’d appreciate your review on Goodreads after completing the book.
How My Unpublished Book Hit the Best Seller Rank in Global Marketing Topic in 5 Days
The power of networking, generosity, abundance mentality, and a mailing list to reach a broad audience and build a…medium.com
Purpose of This Chapter
Medium writers are likely familiar with the pilot Boost program — an initiative I once championed with great enthusiasm during my role as a boost nominator. In the beginning, it felt full of promise, and I was genuinely thrilled each time my nominations were accepted. There was a sense of possibility that kept me engaged and hopeful for what was to come.
However, like all things, that initial excitement faded. By June 2024, the program stopped delivering for me. By August, I made the difficult decision to step down, pulling my best publication, ILLUMINATION-Curated, from the program with teary eyes but with optimism and joy. Ultimately, I closed that beloved pub and rebranded it as Curated Newsletters — a bold new direction aligned with a more meaningful vision.
Now, let me be clear: Substack’s Boost program is nothing like Medium’s. It is an entirely different ball game — one that is thoughtfully designed, fully automated, and truly empowering for creators. Substack’s system is grounded in objectivity. When built and managed by ethical people, machines don’t discriminate. They simply do what they are programmed to do — fairly and efficiently.
In this chapter, I will guide you through the power of Substack’s Boost feature. Specifically tailored for newsletter creators — especially freelance writers — it’s a tool designed to help you gain visibility, grow your subscriber base, and, most importantly, convert free readers into paying subscribers.
This is your opportunity to take full control of your content and elevate your audience in ways Medium’s program could never achieve. Here’s what Substack said about their well-designed and implemented boost program nine months ago:
Why and How to Configure Boost Options on Substack Newsletters
You can access the boos options from the settings page of your newsletter, as shown in the following screenshot. I will break down five individual features with relatable examples and best practices for freelance writers.
First , you need to enable the Boost features, and then you can learn about the rest and choose the ones that suit your strategy, plans, goals, and aspirations.
1 — Enable Pre-Unsubscribe Discounts
This option offers eligible paid subscribers a free month when they attempt to cancel their subscription.
Imagine a subscriber is about to cancel after their first paid month. Before they leave, Substack offers them a free month to convince them to stay. This gives you another opportunity to re-engage them with compelling content.
You can use this as a retention tool by publishing your most valuable and engaging content during that free month. For example, if your newsletter covers freelance writing tips, ensure the next issue offers actionable advice on how writers can land high-paying clients.
2 — Enable Teaser Posts
This option allows free subscribers to view one paywalled post in the Substack app to entice them to pay.
Let’s say you have published an enticing paid post. Teaser posts allow free subscribers to read this high-value content and give them a taste of what they’re missing.
For this teaser feature, you can choose one of your most compelling posts—something that offers immense value or solves a pressing problem for your target audience. Teaser posts should intrigue your readers and motivate them to unlock the full experience by subscribing.
3 — Enable Automated Upsell Emails
This option sends automated emails to your most engaged free subscribers with special offers (by default, a 20% discount on an annual subscription).
If a reader regularly opens and reads your free content but hasn’t yet paid for a subscription, Substack will automatically send them a personalized email offering a discount to go paid.
You can customize these emails to reflect your tone and the value of your newsletter. You can emphasize the benefits of subscribing, such as exclusive tips, behind-the-scenes content, or personal Q&A sessions. You need to make it clear why upgrading to a paid plan will enhance their experience.
4 — Enable Multi-Subscriber Offers
This option provides people who just purchased a subscription to another Substack publication a discounted paid subscription to yours.
If a reader has just subscribed to another Substack on similar topics, they will be offered a discounted subscription to your newsletter. This feature taps into the reader’s willingness to invest more when they have just committed to a purchase.
You can create alliances with other writers who cover related or complementary topics. For example, if you focus on writing tips, partner with a newsletter that covers editing or marketing for freelancers. This helps you capture subscribers already primed to pay for content in your niche.
5 — Customize Automated Upsell Email
This option allows you to edit the automated upsell emails sent to your most engaged free subscribers.
Rather than sending a generic upsell email, you can craft a more personalized message highlighting why your content is worth paying for. For instance, if your newsletter focuses on freelance writing tips, you can mention how the paid version provides in-depth guides on pitching, networking, and scaling a freelance business.
You can use language that feels personal and approachable. Highlight paid subscribers’ exclusive benefits, such as deeper insights, access to premium resources, or community interactions. You could also use urgency tactics, like limited-time offers, to encourage quicker conversions.
As you can see, I turned all options to get benefits from each of them.
Best Practices for Freelancers to Maximize Boost Features of Substack Newsletters
Based on my interviews with the best-selling Substack writers, I distill my findings in the following key points that might give you some valuable insights for your boost strategy.
Focus on Value and Exclusivity: When using teaser posts or automated upsell emails, always emphasize the exclusive content, resources, or insider knowledge paid subscribers will get. Freelancers often have niche expertise, so leverage that to make your audience feel like they’re getting special insider access.
Create High-Converting Content: Use your most popular and impactful content for teaser posts. This will give free subscribers a clear reason to upgrade because they’ll see firsthand what they’re missing out on.
Leverage Discounts at Key Moments: Timing is crucial. The Boost feature helps you automatically offer discounts at the right moments, like when readers try to unsubscribe or after they’ve engaged with multiple free posts. Readers are most likely to reconsider and stay on or convert in these moments.
Personalize Your Upsell Approach: Don’t treat all subscribers the same. Use the customization feature to edit upsell emails with tailored messages that resonate with your audience’s needs and aspirations. Show how subscribing will help them grow or solve their biggest problems.
Collaborate with Other Writers: Use the multi-subscriber offer to partner with other writers. Reach out to newsletters that cover similar or complementary topics and offer mutual discounts to each other’s subscribers, creating a win-win situation.
I designed a supplementary Boost program for our Substack Mastery community.
As a community leader, I created a supplementary Boost program tailored specifically for our Substack Mastery community. While Substack’s automated features are impressive, this program takes things further, enhancing the value members gain from our collective efforts.
Our community currently boasts over 100K subscribers — primarily free — but we are proud to have 112 founding members and several hundred freelance subscribers, all with substantial followings. Together, we are building a content ecosystem through my website where writers thrive and audiences grow.
The primary goals of my supplementary Boost program include:
- Increased Visibility and Reach: Elevating your content to a broader audience through strategic exposure.
- Enhanced Credibility: Building trust and authority as your work gains recognition across networks.
- SEO and Social Media Boost: Maximizing discoverability through targeted optimization, ensuring your content ranks higher and gains more engagement.
- Personal Branding: Strengthening your unique voice and positioning yourself as a thought leader in your niche.
- Paid Subscriber Conversions: Turning free subscribers into loyal paying readers, ultimately driving revenue growth.
This Special Boost Program is designed to be a powerful engine for growth, giving writers the tools to build a lasting audience and expand their authority — not just on Substack but across multiple platforms.
Whether you are a seasoned freelancer or a content entrepreneur, this program can help you transform your writing into a sustainable business.
Let me introduce the essential items in my draft design and discuss the benefits.
1 — Curated Guest Post Per Month with a Guest Author Profile
Featuring a curated guest post each month is a smart move for any writer looking to break into new audiences. You instantly boost your visibility and credibility by showcasing your work to a fresh, engaged community.
Plus, by adding your profile as a guest author, you are not just getting a one-time feature — you are building your SEO value and leaving a digital footprint that drives traffic back to your own Substack or website.
Imagine being a freelance writer with valuable tips to share. Through this guest post opportunity, you offer advice to thousands of eager readers and position yourself as an expert in the field.
This kind of exposure is invaluable, helping you grow your audience and expand your reach far beyond your existing circle. It is a win-win that every serious content creator should take advantage of.
2 — Interview Story from My Substack Account with Top 10 Substack Posts of the Writer
Being interviewed by a fellow writer/editor like me provides you with personal and professional exposure. Highlighting the top 10 Substack posts can add to the writer’s credibility and showcase their best work, potentially converting readers into loyal followers or paying subscribers.
For example, if a writer is a business coach, the interview can highlight their journey and top posts, offering the audience practical business advice while promoting the writer’s expertise.
Here are 3 sample interviews I posted to my Content Strategy, Development, & Marketing Insights newsletter on Substack, subscribed by over 28,900 readers, each receiving over 100K views amplified by my website and social media accounts like LinkedIn, which I covered in a previous chapter of Substack Mastery titled:
“How to Increase Paid Subscribers Case Study #1: Social media is good for promoting Substack, but nothing can beat LinkedIn in converting free subscribers to paid ones based on my experience”
This one is for Veronica Llorca-Smith, a Substack best-selling author.
Interview with Veronica Llorca-Smith to Inspire Substack Writers
Lovely Veronica Is a Bestselling Substack Creator, Professional Speaker, Award-Winning Author, Ironman Triathlete…drmehmetyildiz.substack.com
This one is for our legendary Tim Denning, who is also a Substack best-selling author with a billion content views across multiple platforms.
Why Did I Interview My Aussie Friend Tim Denning Again on Medium & Substack?
This highly followed writer, known for their viral content on Medium, is now getting 50 times more views on Substack…drmehmetyildiz.substack.com
This one is for Wendi Gordon a seasoned freelance writer who has remarkable contributions to the mental health field.
Episode 1: Interview with Wendi Gordon
Freelance writer, book author, mental health champion, and former pastor with a social worker and master of divinity…drmehmetyildiz.substack.com
The Medium versions of these stories sadly got a handful of views from direct links, as the Medium algorithm does not distribute interview stories for unknown reasons.
3 — One Well-Crafted Post with Annotation and a Photo of the Author Per Month
The annotation in the post adds personalized commentary, enriching the content and creating a more engaging experience for readers.
The photo humanizes the content, making it more relatable and memorable. This increases the reader’s connection with the writer, leading to stronger engagement.
Annotating a post about productivity with a real-life example from the author’s journey adds depth, making the advice more actionable for readers.
4 — One Weekly Special Social Media Post with Top 3 Stories and Preferred Images of Writers on Multiple Platforms
Posting across platforms like LinkedIn, X Premium, Quora, Facebook, Typepad, and Reddit enables the writer to reach diverse audiences, significantly boosting visibility.
Highlighting their top stories and images on tailored social media platforms can enhance branding and content recognition.
Freelance writers could promote their content strategy stories on a specific platform while showcasing their creative process on multiple other platforms, reaching different segments of potential clients or followers.
5 — One Special Blog Post Per Month with Key Achievements, Top 10 Posts, and Intellectual Properties
Showcasing key achievements and top posts positions the freelance writers as thought leaders.
Highlighting intellectual properties like eBooks, training programs, or mentoring guides can lead to sales and further credibility while summarizing these in a blog post solidifies the writer’s reputation and attracts more subscribers or clients.
For an author who has launched a course on digital marketing, featuring their achievements and posts can drive new traffic and help them sell their course or attract new consultancy clients.
By thoughtfully managing the boost aspects, we can craft a newsletter that attracts paying subscribers and builds a meaningful connection with our audience. We need to emphasize the unique value of our content, avoid common pitfalls, and continuously refine our approach to offer something that truly stands out in a crowded market.
Related to this story from a conversion point of view, you may also check out my monthly progress on eight different platforms in August 2024 as a content developer and marketer, which might surprise you.
An In-Depth Performance Review of 8 Major Platforms I Contributed to This Month: Key Insights and…
Discover an independent and comprehensive analysis of my contributions and performance across multiple platforms…medium.com
Here is a reality check for beginners.
How Ted’s Return to 9-to-5 Made Him Happier After an Online Writing Business Failure
Discover why going back to corporate life made this person happier and wiser and the key lessons aspiring content…medium.com
Community Building on Substack Bridging with Other Platforms
Integrating Substack with Medium is a great idea. To this end, as a community builder, I created a philanthropic organization that will empower creators, freelance writers, and content entrepreneurs with a commercial arm. I documented the strategy and high-level plan in a story. Please feel free to ask questions and provide feedback. Refraining from perfection, I choose a progressive path.
Here are our draft service definitions for creators, freelance writers, and content entrepreneurs. We will explain the details in our upcoming newsletter.
If you are a writer on Medium and Substack, we have a new publication called Substack Mastery. You are welcome to join and share your Substack experience with your fellow writers and discerning readers. ILLUMINATION-Curators curate, feature, and promote newsletters of our contributors in collections like this one. Being part of a community can bring many benefits, such as a fast-growing audience.
For advanced writers, we also have a publication called Curated Newsletters, which replaced the former ILLUMINATION-Curated. As I resigned from the boost program, I now allocate more time to support writers in extending their services to Substack or other platforms.
If you are a writer, you are welcome to join my publications by sending a request via this link. I support 31K writers who contribute to my publications on this platform. You can contact me via my website. I also have another profile to write and curate tech stories. Friend Links to My Sample Boosted Stories for Non-Members of Medium.
New Submission Guidelines for ILLUMINATION and Curated Newsletters
You are welcome to join the ILLUMINATION Community on Medium and Substack and our education tool, Substack Mastery, curated by ILLUMINATION-Curators. Here is the Importance and Value of Medium Friendship for Writers and Readers
Join me on Substack, where I offer experience-based content on health, content strategy, and technology topics to inform and inspire my readers.
Get an email whenever Dr Mehmet Yildiz publishes. He is a top writer and editor on Medium.
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This story was initially published at DigitalMehmet.com. My blogs and website offer free access to inspiring and educational stories for freelancers and content entrepreneurs. Membership Tiers and Benefits of ILLUMINATION Substack Mastery Community. Please use this portal to contact me with inquiries and feedback.
Thank you for reading my perspectives. I wish you a healthy and happy life.
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