2 weeks ago, I bought a newsletter.

My friend Joe Portsmouth reached out saying he wanted to sell his list to pursue a passion project. We’re in a similar space (he’s a copywriter), but I was apprehensive. It’s a considerable investment with considerable risk.

But on June 13th, I told him I was in.

What changed?

Confidence.

Let me explain.

A question I’ve been wrestling with recently is, ‘Where are you playing to win vs not to lose?’

I realised a lot of my actions were the latter. Don’t get me wrong, I’m taking the pursuit of mastery for writing very seriously. It’s a lot of fun being ‘all in’ on a skill you love.

But I was playing it safe in other areas, like growth.

For reference, I reinvest most of my earnings into index funds and other ‘safer’ investments when I should’ve been investing in the business.

But I avoided paid growth for one reason:

I didn’t think I was a good enough writer.

I thought most of the attention I’d buy would be wasted—like pouring water in a leaky bucket.

But self-belief is self-fulfilling. Sometimes you gotta take actions that force you outside your comfort zone if you want to keep improving.

So, I’ve decided to bet more on myself, and this newsletter purchase was the perfect way to begin.

The deal (part 1)

You can’t just ‘buy’ a newsletter and import it to your list.

So Joe and I wrote 3 emails together explaining the move to his subscribers. Every event is an opportunity to share your story, so we made it clear that Joe was pursuing his passion, and I was passionate about keeping his work alive.

Before the swap over, I also sent an email to his list giving several free copywriting gifts.

You want to begin your newsletter relationship on the right foot (this is why I give a free course to anyone who joins my list, never underestimate the power of first impressions).

In each email, we also invited people to leave pre-transition.

Around 1% did.

This made sure we had no complaints about the swap. After importing (which we did gradually over a week to make sure I didn’t tank my sender reputation), we only had 3 emails asking who the hell I was out of 9,439—not bad for 50% open rates.

Regarding money:

Joe and I agreed a $1.75 per subscriber purchase.

But to further minimize risk, I asked that I only pay on those retained 2 weeks post-subscribing. It would be naive to think everyone enjoys my emails and I’d rather not pay for people who leave immediately.

Joe kindly agreed.

One reason this is good is because 2 months prior, I built a new welcome sequence—a 12-day series containing my best ideas, resources, and, of course, pitching High Impact Writing.

Unfortunately, I don’t know my conversions as well as I should because my business feels like it’s glued together with various software.

Carrd. Convertkit. Thrivecart. It’s hard to know my funnel figures properly.

But by my estimates, each subscriber of my new welcome sequence is worth $2.1. You work this out by tracking purchases throughout the sequence, including upsells and order bumps.

Technically, for anything under $2, I should be growing AND making a profit.

But that’s in an ideal world—which business rarely is.

One consideration is the source of subscribers. Most of mine come from social media. Many who join my list know and trust me. Joe’s list is colder—so I’m shooting fairly blind.

And this is where I leave you today.

I finished importing the list last Wednesday. I’ve already made several thousand dollars back from the first few emails (please don’t ‘nurture your list’ for 2 weeks—buyers wanna buy).

But I won’t know the figures for several more weeks.

The purchase cost depends on how many are retained, and the ROI on how many pick up my products.

If it’s a loss, I’ll have plenty of time to make up for it. I have Magnetic Emails coming, plus other cool ideas for the biz.

But if I break even, that’s a fantastic result.

Considering it’s taken 4 years to build a 30,000-subscriber newsletter, getting roughly 9,000 subscribers in several weeks is a massive leap forward (although I also removed 6,000 cold ones, so it’s a bittersweet win).

There’s also the potential I make a profit on the deal.

If I do, I’ll pretend to have a clue what I’m doing whilst breathing a sigh of relief.

I’ll be in touch with the numbers by the end of July.

Otherwise, it’s a pleasure sharing the process with you.

Hope you found it interesting,

Kieran