Newsletters

My new, Morning Brew-like newsletter gets an F

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A few days ago, I mentioned a guy named Scott Oldford, who is buying up other people’s newsletters. Yesterday, Oldford tweeted a long thread about what makes a newsletter worth buying.

I got my popcorn ready and I sat down to read.

As I’ve mentioned before, I’ve started a new, Morning Brew-like newsletter in the health space.

I told myself from the start to make it sellable. Not because I want to necessarily sell it. But simply because if it’s sellable, it’s more likely to be the kind of business that’s viable for the long term, and that I’d like to be involved in.

I stuffed my mouth full of popcorn and started reading down Oldford’s list. And though it’s still early days for my newsletter, I started feeling pretty good about myself.

Diverse traffic sources: check.

High engagement: check.

Not a personal brand: check.

Diverse monetization strategies: getting there. Like I said, it’s still early days, but monetization is something I know how to do.

​​But then, I got to this part of Oldford’s thread:

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5. You need everything inside of your media brand segmented and process driven & it shouldn’t require you whatsoever.

If I see a business and the founder is running everything— it’s not valuable.

If I see it and the founder is working 5hr/week— it is.

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I stopped chewing my popcorn and I swallowed hard. Fact is, I’m working way more than 5 hours a week on this thing. And I’m doing everything myself.

The biggest time suck is simply the research — keeping on top of all the news stories, tweets, podcasts, blog posts, YouTube videos, and science papers relevant to my newsletter.

​​Like I’ve written before, better ingredients, better emails. If you want to write an interesting newsletter, you have to have interesting things to write about. And that takes time.

So here’s where I hope you can help me:

I might in the end simply have to hire somebody trustworthy and competent to do all this research for me. ​But I’m holding out hope that there’s a technological solution to this problem. Some combination of automated polling of all these resources… machine transcription… AI-based parsing of what’s interesting or not.

​​Something that can reduce this research work by 50%, 80%, maybe 95%.

Something that can take this aspect of my newsletter from an F to maybe a C. Or who knows, a B or even an A.

Maybe it’s a pipe dream. Maybe not.

If you have any info here — whether you yourself have skills and experience to create something like this, or you know someone who does, or you have somewhere to point me to — write in and let me know.

​​All I can promise in return is my gratitude. But who knows — maybe there’s a business in here as well, because there are a million and one newsletters like mine, and I imagine most face this same problem.

Dentists vs. copywriters: Who wins the better customer battle?

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Here’s a new perspective I found insightful, about who you sell to. Maybe it can save you some headache and even failure:

A few days ago, I was talking to a newsletter strategy consultant. He was telling me about his own newsletter, and the paid advertising he is planning for getting paid subscribers to it.

I won’t name this guy — I’m not sure he would want me to — and I won’t reveal the kinds of people he will be targeting with his ads — not so relevant to others but maybe very valuable to him.

So what’s left?

What’s left is the people he will not be targeting with his ads. And this I believe is relevant whatever your actual business is.

The newsletter expert said he will not be targeting independent newsletter creators. Why? Because, as he told me, they are “a little short term and flaky.”

How could it really be any other way?

If somebody has no employees, no office, no expensive and custom equipment, no contracts to fulfill, and in general no obligations, what’s keeping them going if things ever get bad? The answer is nothing.

That’s why it’s in general better to sell to, say, dentists, who are tethered by a million hooks to their businesses, than to, say, copywriters, who can decide from today to tomorrow to close their laptops and go work as a park ranger or to maybe roast coffee for a living.

That’s not to say you can’t make money selling to people who are a little short-term and flaky. But it exposes you to more risk, and it limits what you can sell and for how much.

That’s something to keep in mind whether you sell to other businesses (hopefully, chained and burdened dentists) or direct to consumers (hopefully, people with an unavoidable problem or an all-consuming obsession).

Last point:

​​I found an interesting new newsletter recently.

This newsletter gives the perspective of somebody who manages to profit from short-term and flaky independent newsletter creators. That somebody is Scott Oldford, who has been buying up independent newsletters and then investing in them and scaling them up. Scott writes about his adventures here:

https://investing.scottoldford.com/