AUGUST 20, 2024

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Welcome to The Tilt, a twice-weekly newsletter for content entrepreneurs.

Best Upselling Strategies for Content Entrepreneurs

Strategic upselling is a game-changer for content entrepreneurs who want to boost revenue and delight their customers. It’s all about knowing your audience inside and out, crafting offers they can’t resist, and using tech to streamline your approach.

Here’s the magic: When you deliver real value and customize your offers to fit your audience's needs, you’re not just boosting your revenue — you’re building stronger, more meaningful connections with your customers.

However, many content entrepreneurs shy away from upselling, fearing it might seem pushy. But with the right techniques, your customers will gladly spend more.

Knowing your audience inside and out can make all the difference for your lead generation and upselling efforts. To identify your customer needs and preferences:

• Analyze purchase history: Check what content your customers love — guides, case studies, instructional videos, articles, or podcasts. Then, look at what they've bought in the past — ebooks, courses, memberships, or one-on-one consultations. Additionally, see if they've picked up complementary products, like a webinar with an ebook. And review their feedback to spot what they like and what needs tweaking.
• Monitor competitor offerings: Keep tabs on what your competitors are offering to spot industry trends and gaps. If they’re bundling online yoga classes with wellness guides, outshine them with exclusive diet plans or personalized one-to-one sessions.
• Segment your customers: Divide your audience by interests or behavior. For instance, target fitness fans with advanced workout plans and mindfulness seekers with stress relief courses.

You can also use CRM (customer relationship management) tools to track interactions — website visits, email opens, and social media engagement — to build detailed profiles based on interests, purchase history, and timing.

Once you've gathered insights, leverage them to create personalized upsell offers:

• Mention the customers’ previous actions in your upsell offer, like, “Since you’ve been exploring our blog and webinars about billing, enjoy a free week of access to our premium software.”
• Address your audience personally to avoid a generic pitch. Personalize your messaging to resonate more with them.
• Deliver upsell offers at the right moments, like suggesting an advanced workshop or ebook right after the user completes a beginner’s course.

You can also offer related products or courses in follow-up communications after users attend your webinar. And create personalized landing pages to guide them to upsell offers based on their past interactions.

Just making a personalized offer isn’t enough — you need to make it so compelling customers can’t wait to say yes. Package your content products. To create a tempting bundle:

• Keep it simple: Offer a few well-curated bundles that directly meet their needs or goals.
• Use limited-time offers: Promote bundles with a time-sensitive discount or bonus content to get customers to act fast before it’s gone.
• Elevate your packaging game: Use high-quality design and eye-catching visuals to make your bundles look premium and desirable.
• Pair high and low-value items smartly: Make sure they deliver real value and fit well together. Otherwise, customers might feel tricked and skip your bundles.

Additionally, showcase the bundle’s benefits upfront so customers instantly see the impact. You can also use testimonials or case studies to make your offer more convincing.

Regularly test different bundle combinations with your billing software to find what works, and use these insights to refine your offers.

To ace upselling strategies, your pricing model needs to be spot-on. A clear pricing model shows each option’s value, making it easier for customers to see why upgrading is worth it. Plus, it keeps you competitive by showcasing compelling value propositions that set you apart.

Here are a few popular pricing plans to choose from:

• Tiered pricing offers different versions of a product or service at varying price points, each with additional features. This lets customers pick what suits them best while tempting them to upgrade for more comprehensive features.
• Subscription pricing involves charging for ongoing access to exclusive content, courses, and community memberships. To boost upselling, you can bundle premium products at a discount to make add-ons more tempting.
• The freemium model attracts users with free resources to give them a taste of your value. Once engaged, they are more likely to upgrade to pay for advanced tools or exclusive insights.

When you nail these strategies, you will watch your content business thrive like never before.

-Eduard Klein

​For real-life examples and information on how tech can help, read the blog article.​
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Entrepreneur: Russell Nohelty

Biz: Russell Nohelty

Tilt: Helping writers build more sustainable businesses

Primary Channel: Newsletter (40K)

Other Channels: Website, X (23.6K), LinkedIn (1.1K), Substack​

Time to First Dollar: 6 months

Rev Streams: Books, courses, events, webinars, sponsorships, paid community

Our Favorite Actionable Advice

• Use crowdfunding to validate your content product: Russell used Kickstarter to raise money for his work, but it also allowed him to know when he stumbled onto a good idea.
• Build partnerships: Partnering with Monica Leonelle of The World Needs Your Passion, the two created numerous courses to help authors find success and bring in revenue for both.
• Value newsletters: Russell launched a newsletter in 2015, growing it to 27K subscribers before moving the newsletter, Author Stack, to the Substack platform in 2023. He provided free memberships for the first three months and removed anyone who didn’t open the newsletter in that time. It culled the list to 16K, but he’s now grown it to 40K.

-Marc Maxhimer

Join Russell and the Lulu team on Wednesday, Aug. 21, for a special webinar to learn how to build an audience … that’s ready to buy your books. Register now for this free event.​

​Read Russell Nohelty’s story.​

Know a content creator who’s going full tilt? DM us. Or email tilt@thetilt.com.

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• ​How To Write a Crime Novel (Content Inc.)
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• ​Reddit's Big Opportunity for Brands (This Old Marketing)
• ​Tilt Your Business, the weekly conversation for and with content entrepreneurs, returns on Tuesday at 1 p.m. US EST.
• ​How To Build an Audience From Scratch…​​​​​​​​​That’s Ready To Buy Your Books (Free Webinar)

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