Asking GTP-4 your newsletter questions, plus an interview with Kyle who acquired a 75K newsletter business

Hey there ,

In this weeks issue:

  • Asking ChatGPT-4 newsletter business questions

  • Asking Kyle Scott why he acquired a 75K sub newsletter


Leveraging ChatGTP-4

If youre not paying to use ChatGPT-4 youre missing out. Its answers are so much more comprehensive than its predecessor, and it can now summarize web pages such as the most recent blog post on beehiiv. This is the type of output I can now generate:

You can also use it to make business decisions for you

I ran a poll asking whats the most people would pay for the new AI content package I created and wrote about:

Here was the post on X, the results only show on the web version of this post:

60% of people said $199/m, and 25% said $499/m. Based on the results, I asked ChatGPT-4 to analyse and tell me how much I should price:

It said to optimize revenue keep it at $499/m which is what Im doing.

I also asked it the following questions and got great replies (something I wasnt getting previously in GPT-3.5):

  • What is a typical newsletter sponsorship CPM?

  • If you were an affiliate of beehiiv, how would you generate more referrals?

  • How can you get more sponsors for your newsletter?

As I continue to play with GPT-4, integrating it with a bunch of tools, and continuing to improve prompts, Im starting to feel like I should launch a SaaS tool to satisfy the lower end of the market

Dont forget that the beehiiv done for you setup offer is just $99 this November (normally $199) and includes my product The Newsletter Is The Business.

Buying vs Building

Below is an interview I did with Kyle Scott who recently acquired the 75K subscriber daily newsletter Tip News:

For context, in 2009, Kyle founded the Philly sports website Crossing Broad which became the go-to independent website in the city. It grew to millions of readers and had a 7-figure online store and affiliate business. It became the lead site in a network of sports and betting sites that was sold to XLMedia in 2020.

If youve had an exit or acquisition and would like to be featured just hit reply.

What was your transition into newsletter businesses?

After selling my last site and leaving the company that bought us, I immediately took an interest in newsletters for probably all the same reason everyone else takes an interest in newsletters-- you aren't at the whim of Google or social media and you own your audience. And it's a great format. So I started a small site covering the Jersey Shore, where there is basically no media coverage, and it was an immediate hit.

But that will be a slow burn to becoming a big business (we're working on monetizing through real estate), and so I looked to what could scale quicker. But so many people these days are doing niche newsletters, and my specialty from a content perspective has always been creating for a mass-market audience.

And so then I found Tip News.

Why did you choose to acquire Tip News rather than start a daily news brief yourself

I'm bad a growth. I've been operating with a sizable audience for a decade, and then my partner and I acquired another site, combined our businesses, and partnered with other sports sites in our last business, so it had been a longtime since I had to build an audience from scratch, and frankly I'm kind of impatient.

What was your experience of acquiring on Duuce?

Duuce was great a very helpful. It's how I found Tip News. It was a site I checked almost every day, and when I saw something with scale for a more general audience, it caught my eye. The team at Duuce was very helpful in getting me more information and connecting me with he founder. I look forward to the marketplace offering expanded services to make the process even more seamless!

I see you have a managing editor for the newsletter - was this person in place with the newsletter business previously?

The Managing Editor is James Kratch, he used to work for NJdotCom and I worked with him briefly at XLMedia. I put a job posting on LinkedIn a few weeks before the sale because I knew the current writer wouldn't be coming over, and when James reached out it was a pretty easy decision.

What's your plan to grow monetization going forward?

My background is in affiliate marketing, but I've also had success with direct ads and products. Immediately, I'll aim to improve upon ad sales efforts, particularly with the ad market bouncing back a bit, but also double down on affiliate, which can work really well when you find the right products and offers.

Over time, once I learn more about the audience, I may look to launch spinoff verticals that might have higher value advertising opportunities. I would like to get the the site to beehiiv eventually but I'm a bit hesitant to move that size of a list which has such high open (and low spam) rates.


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Disclaimer: Not financial or business advice. This newsletter is strictly for information and education purposes. There are affiliate links to beehiiv in this issue.