Chat with Chartr Part Deux

📆 Over a month ago, I spoke with Jack Pilcher. This British-ad-sales-beast ran partnerships at Chartr, a newsletter with over 500k subs, recently acquired by Sherwood Media (Robinhood’s media arm).

Our chat was so densely packed with wallet-bulging value that I spread it out over two newsletters. So here we are.

If you missed part one, catch yourself up here.

Lengthy intros aside, let’s dive in ! 🚀

📣 A lot of people are struggling with email deliverability, how do you ensure your cold emails are finding their destination?

I’d recommend signing up for a service like GlockApps. This can check the health and deliverability of your main domains, plus you can set up automated weekly reports that tell you if you’re hitting spam.

Of course, brush up on your DMARC, DKIM and SPF. Step one is to get those in check. Warming emails is a necessary part of any outbound operation these days, so make sure you're using a quality platform for that. Keep mailboxes warming whilst you’re sending emails. We’d be sending 25 emails per day from each domain, with others warming in the background.

To address all the recent updates to email algorithms, I think that Google is genuinely doing this for the greater good. If anything they're just trying to force everyone’s behaviour to be better, whether it works is yet to be seen. 

I get so many sales emails that are not personalised, they’re so obviously blanketed to thousands of contacts, with no unsubscribe button, and finish with “Would you like to chat?”. I know that we can expect a 10% response rate from our targeted efforts, but I bet that most people blasting out like this are struggling with low single-digit percentage replies.

So don’t be generic, tell brands why the outreach is relevant to them and why they should advertise with you. What success have you seen? Who have you worked with? Why are your audiences a great fit?

It’s refreshing that part of maintaining deliverability comes down to quality-focused emails. We send a maximum of 100 emails a day over several domains which has been enough historically to fill our calendar, and then some. 

To summarise, the technical and qualitative aspects are important, it’s simple really. If you’re doing the basic tech stuff right and telling prospects why they should care about your product, with evidence, then you won’t need to worry too much about deliverability.

📣 What is one thing that people can do on the ad sales side that'll be attractive to a potential acquirer? 

Regardless of what type of newsletter you are, try to build around 4 or 5 key (non-salesy) relationships, with companies that share your exact ICP. 1 or 2 years down the line they could turn into a buyer or an exclusive long-term sponsor. It’s at least an open door to a conversation.

A lot of traditional tech companies have the mindset of ‘acquire or build’, which can be very much applied to newsletters. As newsletters have exploded in popularity, I think we’ll see an emergence of the ‘acquire or exclusive’ mindset, where companies will either buy a newsletter or simply broker long-term advertising deals with exclusivity. Sometimes companies want unfettered access to an audience, but they simply don’t have the appetite to ingest and run a whole media startup.

These relationships take time, often 6, 12 or 18 months. Have quarterly calls and just catch up on what's going on in the business. Another benefit of this, is if someone does inbound about acquiring your business, you now have 5 other relationships that you can go to and say “Hey, XYZ wants to buy us, we like you, would you want to explore this too?”.

This is hypothetical of course, but that can create the dream outcome of having a bidding war for your business.

📣 Outlook for newsletters and ad sales in 2024 and beyond..?

It’s fair to say that there will continue to be an increase in the medium. One of the main attractions is that it’s an audience that you own, a tech exec in Palo Alto doesn’t have complete control over your business.

I think it’s a scenario where the pendulum of success will swing back to quality. The cream will rise to the top and those who don’t have best practices will find life very difficult.

On the ad sales side, as more and more inventory becomes available it can be tempting to get caught in a race to the bottom, bottom barrel pricing that is. Especially, as most newsletters are bootstrapped and need ad revenue to survive. 

The best way to combat or avoid these challenges is either having scale (i.e. a large number of subscribers), or being extremely niche. Payload is a fantastic example of how you can build a great business with very few subscribers.

Scale is difficult and expensive, my preference would be to own a high-value niche.