How Josh Spector created an eCommerce store to sell newsletter ads

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If you’re a creator, and you aren’t following Josh Spector, you should be.

Josh is an expert at all things audience building and business, specifically for fellow creative entrepreneurs. On Twitter and through his newsletter, which reaches more than 19,000 people, he provides his followers valuable and actionable ideas to help them “produce, promote, and profit” as creators.

Josh doesn’t just talk the talk. He walks the walk, too. He’s sold countless digital products and booked consultation work with clients through sharing his expertise as a creator.

More recently, Josh has started generating additional revenue for himself through newsletter sponsorships. He was originally hesitant to run newsletter ads over fear that they’d annoy his readers. But a few years ago, he started to change his tune when he realized that ads wouldn’t bother people as long as they provided value.

Fast forward to today, and Josh generates roughly $48,000 a year through newsletter ad revenue alone. That figure is expected to increase as he’s incrementally raised the price of his ads.

Running newsletter ads is a revenue stream that isn’t much of a heavy lift for Josh because of the system he’s put in place. He’s figured out a working sales and fulfillment process that involves automation and the outsourcing of administrative tasks.“My ads are purposefully simple,” Josh said. “There’s no images. It’s just a certain character count and one link.”

How did Josh build his newsletter machine? What tools does he use? He was gracious enough to explain the details to me during an appearance I made as a guest on his weekly 30-minute podcast, “I Want to Know.”

Why can’t you sell an ad online the same way you can sell a t-shirt?

That was the question Josh had when he first started seriously considering selling sponsorships on his newsletter.

There are countless e-Commerce platforms out there that help entrepreneurs set up internet storefronts. In Josh’s mind, he wondered if he could use one of those platforms to sell newsletter ads instead of physical products.

So he and his assistant Emily decided to set up an experiment. They built a digital storefront using Square, launching a website that lived on its own with one of the platform’s basic eCommerce templates.

There were some slight adjustments they had to make that differed from the usual eCommerce buying experience. Unlike a t-shirt, where all that’s needed for fulfillment is a customer’s shipping address, Josh needed a way to receive a company’s brand deliverables.

To achieve this, Josh and Emily realized they could customize the confirmation message that someone received after they purchased. “We did that and that autoresponder basically said, ‘Thanks for buying. Reply to this email with copy (and links) for the ad,” Josh told me.

Once a sponsor sends back their copy, the next phase of fulfillment is managed manually by Emily. She takes their copy and pastes it into a Google Sheet that’s shared with Josh. Then when it comes time to run the ad, all Josh needs to do is open the spreadsheet and copy and paste the messaging into ConvertKit.

But what happens if ad buyers don’t send their copy back in time? Emily has to ping them an email reminder, usually a week out from the date their ad is supposed to run. Fortunately though, this doesn’t happen often and it’s not that difficult to address.

Why Josh limits his ad inventory

Josh offers sponsors a limited number of placements in his newsletter. His daily newsletter features only one sponsor per email while his Sunday edition features a maximum of 7.

Part of the reason for this is simplicity. With a team of only two people to sell and fulfill ads, keeping ad inventory low is easier to manage.

But another reason revolves around manufacturing demand. This is something Josh learned about through his experiences in his previous career producing standup comedy shows.

Here’s an analogy he shared with me, paraphrased for clarity:

Say you’re launching a new weekly comedy show and you think you can sell 70 tickets on a regular basis. For your venue, you have the option of choosing between theaters that hold either 50 or 100 people.

Most show producers’ instincts would lead them to pick the space that holds 100. If you know you can sell 70, why would you lose out on 20 extra sales choosing a venue that’s limited to 50 people?

But the truth is, the better option would be the smaller space. By choosing the venue with a maximum capacity of 50, you create the perception that the event is a hot commodity. Selling out and having 20 people a week who can’t get tickets can generate buzz.

Remember the laws of supply and demand. Take that into consideration when determining how many ad placements you decide to sell advertisers.

Simplicity is a key theme to Josh’s approach

His tools are limited to Square, Google Sheets, and Convert Kit - all of which you can get started with for free. The ads he runs are text-based rather than rich media content like images or videos.

Josh also doesn’t do much outbound prospecting for sponsors. As a creator, he’s built up enough goodwill with his audience, many of whom jumped on the opportunity to advertise in his newsletter as soon as he launched.

So what’s Josh’s advice to creators thinking of building an eCommerce store to sell sponsorships? “The fate of your ads…is not dependent on your tech stack,” Josh said. “Almost anything you choose will work. Some may be better or easier to use than others…

“It’s not as important as the content, the strategy, the value you deliver to advertisers. The way you position the ads… all that stuff is more important.”