🚀 This blog is part of a series featuring real-world insights from business owners who’ve been there, done that—aka the Shortcuts Squad. These are the lessons they’ve learned, the strategies that worked, and the pitfalls to avoid.
đź“Ś Want more takeaways from other entrepreneurs? Find the full series at the end of this post!
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When it comes to selling digital products, there’s no one-size-fits-all strategy. Just ask Bob Grant from Relationship Headquarters, a seasoned entrepreneur who has spent nearly two decades building a thriving business selling relationship advice products to women over 35. His secret? Leveraging affiliate marketing on platforms like ClickBank to generate millions in sales.
The Niche: Relationship Advice for Women Over 35
Bob’s audience is clear: women who are either looking to get married, struggling in their current relationships, or feeling like they have just one more shot at finding love. It’s a highly emotional niche, and Bob has learned how to craft products that speak directly to their fears and desires.
How ClickBank Became a Game-Changer
For those unfamiliar, ClickBank is an affiliate marketplace that connects product creators with affiliates who promote their products in exchange for a commission. Bob has been using ClickBank for nearly 20 years, and he credits it with a significant portion of his success.
“ClickBank is a platform that’s really set up for affiliates. They take care of everything—payments, tracking, taxes—and make it easy to get your product in front of motivated sellers.”
The key to success on ClickBank? A high-converting offer. Bob tests his sales pages rigorously, ensuring they convert at least 2-3% before reaching out to affiliates.
Affiliate Marketing = The Power of Other People’s Audiences
Rather than relying on paid ads or building an audience from scratch, Bob taps into existing email lists by partnering with affiliates. His strategy for getting traction:
- Making sure his offer converts well before approaching affiliates.
- Reaching out to affiliates in his niche with a compelling offer.
- Offering a 100% commission on the front-end product for test promotions.
- Building a buyer’s email list from ClickBank sales.
“A buyer’s list is gold,” Bob explains. “People who buy one product are much more likely to buy again.”
Expanding Beyond ClickBank
While ClickBank remains a core part of his business, Bob has diversified by selling coaching services through SamCart. Unlike ClickBank, which is best suited for digital and physical products, SamCart allows him to sell high-ticket services.
Additionally, he’s re-entering the world of Facebook advertising to complement his affiliate marketing strategy.
The Lifeblood of Digital Sales is Email Marketing
With a list built from ClickBank sales, Bob nurtures his audience through email marketing. His approach:
- Emailing at least three times per week.
- Providing value while subtly promoting products.
- Running major promotions for high-ticket items once per quarter.
“If they’re opening emails, they stay on the list,” he says. “People buy when the timing is right for them.”
What Every Digital Product Seller Should Know
Bob’s experience has taught him several key lessons:
1. The Sales Process Matters More Than the Product
“As a former therapist, it pains me to say this, but the sales process is more important than your product. If you can’t sell it, it doesn’t matter how good it is.”
2. Focus on Lifetime Customer Value
“It’s tempting to focus on making all your money upfront, but looking at the long-term value of a customer is key. A good percentage of buyers will purchase multiple products over time.”
3. Talk to Your Customers
“One of the best ways to breathe new life into an existing product is to talk to your customers. Their language, concerns, and needs evolve, and tweaking your messaging can make all the difference.”
Bob’s Favorite Tools
Running a digital product business requires the right tools. Here’s what Bob uses:
- ClickBank – Affiliate sales platform.
- SamCart – Handles high-ticket coaching sales.
- ActiveCampaign – Email marketing and automation.
- Slack & Trello – Team communication and project management.
Final Advice for Digital Product Sellers
For those just getting started, Bob advises a patient, persistent approach:
“If this is a side hustle, take your time and let it grow naturally. If you go all in, commit fully. People are always buying—it’s just about getting the right offer in front of them at the right time.”
There are multiple ways to succeed in the digital product space and Bob's approach is just one of those. Whether through affiliate marketing, paid ads, or organic audience building, the key is consistency, testing, and delivering value.
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🔥 Want to see how other entrepreneurs are making it work? Explore their strategies, lessons, and unexpected wins below:
đź”—Â How to Build a Seven-Figure Digital Product Business: Lessons from Sarah Masci
đź”—Â How One Entrepreneur Uses Virtual Summits to Supercharge Digital Product Sales
đź”—Â How Dara turned a simple idea into a $200,000 digital product
🔗 How Anthony Kuo’s Simple Approach Fueled His Digital Success
đź”—Â Building a Simple, Authentic Digital Product Business: Lessons from the Island
đź”—Â How Sarah McDugal Empowers Women to Build Digital Businesses
đź”—Â How Mark Turned an 'Impossible' Niche into a 7-Figure Digital Product Business
🔗 Laura Khalil’s No-Ads Approach to Landing High-Paying Corporate Clients
🔗 Stop Overcomplicating Digital Product Sales—This Simple Strategy Made Six Figures