Try the easy version first.

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I first started offering sponsorships in this newsletter back in late 2022, when I had somewhere around 35,000 or 40,000 subscribers.
I don't remember the exact number, which I think is useful to point out because there isn't some magical subscriber count where you’re suddenly “big enough” to sell sponsorships. All I knew at the time was I had a pretty specific audience and that 65% of them opened my emails every week. I figured there were probably a lot of companies that might want to get in front of some highly engaged readers.
The problem is that I had absolutely no idea how sponsorships were supposed to work. So my wife, Jennifer, and I sat down and started doing some research.
Fast forward a few hours and we had about a million tabs open explaining everything from sponsorship software to media kits to packages and pricing to custom deals, images, recommendations, and how prominently the product should appear.
And for every opinion we read on what was best, there was an equally compelling opinion to do the opposite. By the time we were done sifting through all of the information, we were convinced that we had to get on calls with potential advertisers, negotiate a bunch of different packages, write custom copy, and take selfies holding the product. That just didn’t fly with us.
The more we read, the more we hated the idea. I remember at one point I said to Jennifer, “Why does this have to be so complicated?”
We were running the entire business ourselves, and had zero interest in creating some new advertising agency inside of it. If we were going to offer sponsorships, it needed to work the way we wanted it to work. Simply. There had to be a straightforward process that the two of us could run without adding any meetings, back-and-forth, or complex admin work.
So we closed all those tabs, grabbed a piece of paper, and started to sketch out exactly how to do sponsorships our way.
The first thing we did was design a simple page we could put on the website that would explain exactly what a sponsor got and answer all of their questions. How much did it cost? Where would the sponsorship appear? How many characters could their copy be? What could they include? What wasn't allowed? We wanted to make sure that everything was covered without having to hold a meeting or exchange clarifying emails. No extra work.
At the very bottom of the page was a simple buy button to purchase a sponsorship and a calendar where they could choose an available date.
After a customer bought, they'd get an automated email ten days before their sponsorship ran, with a link to a form where they could enter everything we needed. On Mondays, Jennifer opened up the email, copied and pasted everything over, and we were done. Today, a custom AI does the same work.
That was the entire operation. The whole sales process. There would be no meetings, no negotiations, no logos, and certainly no selfies. Companies either liked what we offered or they didn't. And it turned out that enough of them liked it to continue doing it our way.
Over time, the newsletter grew to more than 200,000 readers, and sponsorships became more valuable because there were more people clicking through. But the simple way we sell them never became more complicated.
Looking back, I think we could've easily gone in a completely different direction and ended up like so many of the lifestyle entrepreneurs I advise. Bogged down by complex processes and admin work that takes them away from focusing on the real work of growing their business.
We could've flexed on what we offered. Maybe a company wants to buy a sponsored social post or a custom package of 10 sponsorships. Or marketing teams would want to jump on a call before booking and brainstorm the best way to work together. Those requests are completely reasonable, and some of them definitely would've made us more money.
But every new thing we agreed to would’ve also become something we had to remember, deliver, schedule, discuss, and manage. And with no employees to help with that process, it just didn't work for us.
The nice thing about having an audience, a product, a skill, or anything else that people actually want is that you have leverage. You don't have to accept every possible transaction. You can decide what you're willing to offer, explain it very clearly, and let the other person decide whether or not it works for them.
When you have something people want, you get more say in how you sell it.
That doesn't mean you'll always get your way. If nobody bought our sponsorships, we would've had to change something. Maybe we would've lowered the price, or beefed up the offer, or decided to allow logos or do calls.
But making a change after a product or service isn't working is very different from adding complexity to it before anyone's even asked.
I still see entrepreneurs doing this all of the time when they're building out something new.
They don't have a single customer, yet they've designed ten different packages, made room for every little special request, and purchased expensive tools they might eventually need someday.
I highly encourage you to avoid doing that.
Instead, find out whether the simplest version works first.
When we started accepting sponsorships, we had no idea what we were doing. All we knew was that we had a group of readers that companies wanted to get in front of, and we wanted to make it easy for those companies to do that. The one caveat?
It couldn’t make the business harder to run.
So we put the offer on a simple page, told people exactly what they would get, and gave them a button to buy it.
Four years later, that’s still exactly how it works.

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