How Gretchen Rubin and Nico Cerdeira Learned How to Sell Ads in Their Newsletters

This case study is presented by Who Sponsors Stuff, which gives you and your team the tools to quickly find and reach out to relevant sponsors for your newsletter. They track 500+ newsletters, have direct contact information for 8,000+ sponsors, and keep you on the cutting edge of who’s spending money in the email advertising space. Find out how their Sales Pro product can supercharge your ad sales operation today.

Renowned happiness expert, best-selling author, and podcaster, Gretchen Rubin, has been regaling audiences for over a decade with tips and resources on living happier, healthier, more productive, and more creative lives. She has amassed over one million newsletter subscribers who eagerly anticipate her weekly Five Things Making Me Happy edition in their inbox. But it wasn’t until recently that Gretchen and her team, led by CEO Anne Mercogliano, started to incorporate sponsorships into their successful newsletter product.

In November 2023, Inbox Collective, in collaboration with Who Sponsors Stuff founders Ryan Sager and Jesse Watkins, launched their Ad Sales Lab pilot program geared towards newsletter operators who needed support with their ad strategy, from ad pricing to ad products, sponsor prospecting and negotiating, and outreach tactics. Over 100 newsletter operators applied to be part of the Lab. A handful were selected, including the team behind Five Things Making Me Happy.

For Gretchen and Anne, participating in the lab was a game changer. “We went from zero to 100,” Anne shared on a recent call, four months after being selected for the pilot. “We were only comfortable launching this revenue program because we were part of the Ad Sales Lab and got to work with Who Sponsors Stuff. The program wouldn’t exist without them.”

Learning to ask the right questions about advertising

When it comes to newsletter growth, Gretchen, Anne and the team have a clear strategy. They deploy podcast promotions, pop-up widgets on site, optimize their SEO and publish quizzes to encourage engagement — there’s no shortage of tried-and-true levers to pull to reach new and existing audiences. Monetization was largely built around driving readers to purchase products, like books or merchandise from the Happiness Project Store, or nudging readers towards their app, Happier, which offers a premium subscription. But when it came to monetizing the newsletter through ads, the team treaded carefully. Value alignment was, and remains, of utmost importance.

“We look for brands that can be part of the overall value prop to our subscribers,” said Anne. “Gretchen has, of course, done specific partnerships with larger sponsors. But it wasn’t until the Ad Sales Lab program that we really thought, ‘How can we work with advertisers who work really well in our ecosystem?’ The nice part about working with Who Sponsors Stuff is that you get to see the variety of sponsors and also where they are in other newsletters. So based on the other newsletters they track, we felt really confident that we could find brands that make sense and would work well within our newsletter based on the topics we cover.”

Sales Pro, the flagship database from Who Sponsors Stuff, tracks over 8,000 potential sponsors and more than 500 newsletters. As part of the Ads Sales Lab, Gretchen, Anne, and the team were able to access the tool for free and narrow down which sponsors align thematically and which have sponsored other newsletters in their space.

“It’s a really innovative way of thinking about advertising,” added Gretchen.

But it’s not enough to identify which advertisers might be a good fit. From conversations with Who Sponsors Stuff, Gretchen and Anne started to identify questions they needed to answer to properly build out their ad strategy:

• Start with the big questions — How often do you expect to include a sponsored unit? How many units do you want to deploy in every newsletter? Where in the newsletter would you like for the unit to appear?
• Why is this the right advertiser for your audience? — The best newsletters share with subscribers why this brand matters to you, what difference the product has made in your life, and why you’re recommending it.
• How do you want to display the product? — Adding a visual component is key. Newsletters are a visual medium. Remember you can also show (a photo of the product or experience), not just tell.
• Is there something special you can offer readers? — Starting out, see if you can identify a tangible takeaway, like a free sample, as you ease your readers into seeing more sponsored content from you.
• Can you build long-term partnerships? — Finding partners who want to work with you over a longer window of time often works better than offering one-and-done ads. Those partnerships are better for your newsletter’s bottom line, but building relationships over time also helps subscribers understand how the advertiser fits into your life and how it can fit into theirs.
• Are you meeting your own ad standards? — If you offering advertising elsewhere, as Gretchen does on her podcast for instance, uphold those standards for your newsletter. Value your newsletter the way your audience does and the way you expect a brand partner to. 

Building an outbound strategy

Leveraging Who Sponsors Stuff’s Sales Pro isn’t solely beneficial to those brand new to newsletter monetization. 

Nico Cerdeira of the newsletter Failory was also selected to partake in the Ad Sales Lab despite selling sponsorships for his newsletters going on two years. In fact, he said on a recent call from his home in Argentina, sponsorships are the largest source of income for his digital products.

“I recently increased the frequency of the newsletter from one email to two emails per week,” explained Nico, whose newsletter reaches 40,000 subscribers, mostly in the U.S. and Canada. “All of the sponsorships that I got over the past few years came organically. They were companies that found our Failory newsletter, they’d reach out to me and sponsor one or more issues. But when I increased the frequency, I realized that the amount of leads that I was getting organically from sponsors was not going to be enough to fill all of the new sponsorship slots. I needed to do some cold outreach to find sponsors. And that’s where [Ad Sales Lab] came in.”

Consulting with Ryan and Jesse enabled Nico to identify relevant sponsors who’ve run sponsorships in similar newsletters, find their contact information, and craft outreach copy. This outbound strategy has so far resulted in four new sponsors in as many months.

“My goal is to have a 100% fill rate for the sponsorships,” said Nico. “50% to 60% comes from organic leads, so my goal is to get 40% of sponsors every month from this cold outreach strategy.”

Nico shared a sample outreach copy that he’s come up with, following conversations with Who Sponsors Stuff:

Hey Rachel,

I hope you’re doing well! My name is Nico, and I’m the founder of Failory, a weekly newsletter for startup founders.

I’m currently bringing on sponsors for the next few months. I’m reaching because I’ve seen you’ve sponsored other newsletters in the space.

We have an audience of 40k+ subs, mainly from the US. The majority of them are founders, 50% of whom are making $10k/mo.

I think Failory might be a good fit with Deel. Would you have some time to discuss this over this week?

In the future, Nico said, he hopes to utilize Sales Pro to expand into new verticals for even more sponsorship opportunities. He sees the potential for advertisers in the personal finance space, for instance, who’d align nicely with his audience of startup founders and investors. 

Finding the right advertisers to work with

“Alignment between a publisher and a sponsor depends on a lot of different things,” said Jesse Watkins, co-founder of Who Sponsors Stuff. “Using our database, you have a lot of that intelligence already there for you: I can see exactly what copy this sponsor is running in which newsletter, I can check the sponsor’s social channels and their different brand messaging, product lines or offerings that they’ve advertised and determine if there’s alignment there with my brand. And ultimately, it’s important, because if it’s a brand that doesn’t make sense for my audience, it’s just not going to perform well.”

“Sales Pro is a prospecting tool for newsletter publishers,” he said. “Through the lab, we gave people access to the database and worked with them to stand up their first few ad sales deals. So they could prove out, ‘Oh, this is how we monetize this audience.’”

“We worked with these newsletters as if working with a publisher,” said Jesse. “This is how you should think about prospecting, these are the types of sponsors that I would go after, this is how I would talk to the sponsor, these are the newsletters that you should keep an eye on for sponsors, as well as tactically, when reaching out: This is how I would reach out through email, this is what I would say. We got granular.”

While the database is accessible for a fee for most, Who Sponsors Stuff provides ample free advice — as well as a useful ads calculator — on their website. “It’s a pretty good starting point for people who haven’t sold an ad before. It helps to know, Okay, I’m within market here,” Jesse said.

“Our mission in the space is to help stand up independent media brands with new revenue streams,” Ryan said. “In so much of the web, you’re dealing with traffic arbitrage games. You’ve got companies chasing after scale, whereas a newsletter can come in–an owner-operator or a very small team —  create something phenomenal in terms of content and quickly monetize. And that is what our product is designed to do, to give that person or team a tool that they can use to go out and prospect and do their own ad sales and own their own revenue.”

For those owner-operators or small teams starting out, Ryan and Jesse emphasize that while growth is important, there is no universal audience size that sponsors look for. “Some B2B newsletters can monetize at 5,000 to 10,000 subscribers,” Jesse said.

The most important lesson was one they emphasized both to Gretchen and Nico: The more you know about your readers, the better you can explain the value of the audience to potential advertisers.

“Knowing your audience well is first and foremost when approaching new business,” he added. “I can’t sell what I don’t know, right? If I don’t know anything about my audience, how am I supposed to sell access to this audience?”

This case study is presented by Who Sponsors Stuff, which gives you and your team the tools to quickly find and reach out to relevant sponsors for your newsletter. They track 500+ newsletters, have direct contact information for 8,000+ sponsors, and keep you on the cutting edge of who’s spending money in the email advertising space. Find out how their Sales Pro product can supercharge your ad sales operation today.