S01E47: Coaching Session: Tips from a Newsletter Pro — with Josh Spector of For The Interested
— A one-paragraph newsletter shows you simple, proven ways to use writing to grow your business based on how others have done so.
1hr listen
How The Rollup is growing fast while maintaining high engagement
Think finance newsletters are all charts and numbers?
Think again.
Meet The Rollup – Sam Klemens' unconventional finance newsletter that's rewriting the rules.
Kicking off in early 2023, Sam has turbocharged 'The Rollup' to an impressive 14k subscribers in less than a year while maintaining a 60% open rate.
And we're diving in to find out how.
In this week's Friday Feature, learn how Sam rapidly scaled The Rollup, crafted content that gets engagement, and nailed a monetization strategy that's as flexible as it is effective. And like usual, we're laying out the blueprint so you can do it too.
Here’s a sneak peek how Sam is…
- being innovative with content curation and personalization
- wisely investing in growth
- being flexible & adaptive with monetization
Let's jump in.
#1 - Innovative Content Curation and Personalization
In a sea of similar newsletters, The Rollup shines by stepping away from conventional finance news and embracing content from alternative sources like Substack, Twitter, and YouTube.
Not only that, Sam takes The Rollup’s content a step further by infusing his personality with humor and varied interests, making finance more approachable, unique, and fun.
🧐 Why it’s awesome
→ Distinctive Edge: Unique, unconventional content sources set you apart in a crowded market.
→ Enhanced Engagement: Personal touches and humor can deepen reader connection and loyalty.
→ Niche Mastery: Carving a specific niche attracts a dedicated audience.
🙋 How The Rollup does it
Sam actively curates content from non-mainstream platforms, offering fresh investment insights. He incorporates memes and AI images, blending financial insights with light-hearted elements.
Exhibit A:
Exhibit B:
✏️Steal this for your newsletter
When everyone in your niche is zigging, you zag by getting unique, unconventional, and obscure (get a little weird—but not too weird).
- Explore beyond the conventional: Dig into niche platforms for content that resonates with your audience's interests.
- Express yo’self: Don't be afraid to let your personality shine through your content. Everyone has their own sense of humor and tone of voice. Find yours and USE it.
- Balance and blend: Mix in elements that add value and enjoyment to your core content.
- Test, iterate, improve, and test again: Keep an eye on metrics and feedback to figure out what’s working and what isn’t. People might love your unconventional approach, or they might be unsubscribing in droves.
🎧 Bonus: Learn about other creative ways Sam is curating & crafting unique content for The Rollup in our recent chat →
#2 - Smart Investment in Growth
Michael Houck first shared with us how he heavily reinvested 100% of his newsletter profits into growth.
Sam is doubling down on a similar strategy—and has become another prime example of the power of investing newsletter revenue back into growth.
By using SparkLoop’s Upscribe widget to make paid recommendations, Sam effectively offsets his advertising costs, creating a flywheel for growth and expansion—and Upscribe revenue allows Sam to spend even more on growth than he otherwise could.
🧐 Why it’s awesome
→ Sustainable Growth: Reinvesting revenue into growth strategies ensures long-term expansion.
→ Cost-Effective Marketing: Offset advertising expenses with revenue from paid recommendation programs like SparkLoop’s Upscribe.
→ Boosted Acquisition: Paid strategies complement organic growth, accelerating subscriber increase.
🙋 How The Rollup does it
Sam uses SparkLoop’s Upscribe widget to make paid recommendations.
He then reinvests his Upscribe earnings into paid ads, allowing him to grow his newsletter much faster.
✏️ Steal this for your newsletter
Smart newsletter operators like Sam and Michael are reinvesting newsletter revenues back into growth.
Bottom Line: Upscribe is the easiest way to unlock extra newsletter revenue and have your subscribers loving the recommendations.
We’ve seen newsletters in all shapes, sizes, and niches unlocking meaningful revenue with Upscribe.
One partner has already earned nearly $100k in a single month making paid recommendations via Upscribe:
🧮 Bonus: how much can YOU earn when you activate Upscribe? Find out with our earnings calculator →
#3 - Flexible & Adaptive Monetization
Sam's journey with The Rollup highlights the importance of adaptability in monetization strategies.
He assumed the magic number for selling ad spots was 10,000 subscribers. So he hit 10k subs and started pitching ads—but all he heard were crickets:
“I thought a $100 [ad spot] sounded like a fair price to advertise to a 10k subscriber newsletter, and I naively thought that if I threw that offer out there, a lot of people would take me up on it,” Sam shared with us in our podcast chat.
He quickly adds, “and... they did not."
So Sam shifted his thinking, taking a page out of another newsletter operator’s playbook.
🙋 How The Rollup does it
After struggling to bag $100 for ad spots in The Rollup, Sam saw what Anthony Castrio was doing for his Bot Eat Brain newsletter:
→ pitch ridiculously low ad rates to attract advertisers and “sell out” ad spots—then gradually increase ad rates as each edition sells out.
🧐 Why it’s awesome
→ Attract Initial Advertisers: Low rates can be more appealing to first-time advertisers.
→ Build Credibility and Demand: Gradually increasing rates as your audience grows demonstrates value.
→ Consistent Revenue: Early and consistent ad revenue supports newsletter operations.
✏️ Steal this for your newsletter
Newsletters big or small struggling with selling newsletter ads can leverage this strategy.
→ Start Small to Attract Big: Introduce low advertising rates to reduce supply while increasing demand.
→ Scale with Growth: As your newsletter grows and editions sell out, incrementally increase your rates.
→ Showcase Success: Use past advertising successes as case studies to attract higher-paying advertisers.
Adding it up…
Sam Klemens isn’t just running a newsletter; he's mixing things up with 'The Rollup'. And it’s working.
Unique content? Check. Clever reinvestment strategies? You bet. And don’t forget about those adaptive, flexible ad prices.
And with more and more finance newsletters being published all the time, Sam is well-positioned to stand out among the rest.
Here are 3 things to do next:
- Check out The Rollup if you haven’t already →
- Listen to our whole chat with Sam Klemens on our podcast →
- Give us your take: what newsletter is doing something different and innovative we should feature next? Maybe it's yours... EMAIL US and let me know!