Dan Oshinsky’s Post

What percentage of your social audience can you reasonably expect to convert into subscribers to your newsletter? Here’s a rule of thumb based on my work with indie newsletter operators: ❶ Add up the number of Facebook, Instagram, LinkedIn, and Twitter followers that you have to get the size of your overall social reach. ❷ Most people are able to convert at least 2% of that total audience to newsletter subscribers. The very best operators might convert up to 10% of their audience to their newsletter. So multiply your overall social audience times .02, and then .10, to give you an estimated conversion range. That doesn’t mean that you’ll convert this many readers on Day 1 — it may take months to bring some of these readers over! And a lot depends on the tactics you use to convert readers into newsletter subscribers. But this is usually a good starting point to help you set that initial conversion goal.

There’s a lot I wish I’d known when I launched my first newsletter. And I was curious what others wished they’d known, too. So Claire Zulkey and I asked other newsletter operators — like Jennifer Flanagan, Geoff Sharpe, Sarah Ebner, Jason Feifer, Max (Marketing Max) Bidna, Meagan McGinnes, MBA, and Joanna Ericta — for the advice they wish they’d gotten when they were first starting out. From content strategy to growth best practices, here’s what they told us.

Weekends are different now as a new dad. Before my son was born, I’d often spend a little time on the weekend doing some work. That might mean a little time on a Saturday morning doing some writing, and then time on Sunday evening prepping for the week ahead. If I had the time, I might cross a few other things off my to-do list. Of course, becoming a dad changed all that. For a the first few months of my son’s life, I might be able to sneak in time to get 1-2 work things done on a weekend. And I’ll be honest: For a while, that felt a like failure. What I needed was a shift in mindset. Getting 1-2 things done on a weekend isn’t a failure — I’ve got a kid now! I’ve got other responsibilities! If I get 1-2 things done, that’s a very good day. Now, if I know I might I get a few hours to take care of work on a weekend, I’ll look at my to-do list and figure out what the priority task (or two) is. If I get through those tasks faster than expected, I don’t go back to the to-do list for additional tasks. I leave everything else for Monday morning. Getting those 1-2 things done is more than enough.

One mistake I see, particularly in the subscription business, is when newsletters set the price of their subscription based on the price they see others charging. It’s why so many paid newsletters charge $5 a month or $50 a year for their subscription — it’s a fairly common price point. But it may not be the right price for your newsletter. Before you set a price for a subscription, I’d encourage you to consider some key factors: ⃗→ How big is your potential audience? Do you write for a massive audience or a niche one? ⃗→ How easy is it to find the content you create? Be honest: Are there lots of other writers or creators in this space, or will readers find this content exclusively in your newsletter? Hard-to-find content for a niche audience, like a business-focused newsletter, might be worth hundreds or even thousands of dollars per year. Content that’s easy to find elsewhere and that’s intended for a massive audience might be worth less than $100 per year. Think about where your newsletter falls on the spectrum below, and use that as a starting place to price your offering. Smart newsletters often start with a slightly higher price point and then offer occasional discounts, or they’ll use free trials where a reader enters their credit card upfront but is not charged until the end of a specific window, which could be as short as a week or as long as a month. 

The next time you make an email mistake, just remember: Everyone does it — including The New York Times. Here’s an email a reader of mine got last week from the Times. The subject line was about Pete Wells’ top 100 restaurants, but here’s what they saw inside: ——— “Wirecutter headline (or some version of it) goes here” “You can often use the Wirecutter web summary here. write a short intro that introduces/sets up the article, but doesn’t summarize it fully. Try to employ curiosity gap and not give away too much in the inbox. We want them to click to read the piece.” ——— To eliminate big mistakes, make sure you build out a pre-send checklist for your newsletter. Don’t hit send on an email until you’ve checked all the boxes: ✅ Is the sent-from name, subject line, and preheader text right? ✅ Are we sending to the right audience? ✅ Is the email scheduled to go out at the right day and time? ✅ Are all the links working? ✅ Are there any typos in the email? ✅ Did we run a check for accessibility? ✅ Does the mobile version of the email look good? And if an error still slips through, come up with a plan for how to handle the mistake. Here’s what the Times sent out: “An earlier draft of this email was mistakenly sent. We are resending the correct version now. Our apologies.”

When I say stuff like, “Your newsletter doesn’t work unless it works for you,” this is EXACTLY what I mean. Here’s a perfect example from Puck’s Matthew Belloni. His newsletters, which cover the business of entertainment, always come out on Sundays and Thursdays. The Sunday night edition is great — it’s a tone-setter for anyone who works in Hollywood. But Matthew dropped this note into today’s edition: “My kid is getting older, I need to be available for sports and other activities on weekends, and it’s been tougher and tougher for me do all that and keep up the quality that readers deserve. Delivering the best product is the top priority, so Mondays and Thursdays it is.” I love two things about this: ✅ He’s adjusting the newsletter to fit his schedule. ✅ He’s clearly explaining the change to readers. Whatever you work on, make it work for you.

Don’t be the newsletter where every CTA says “Click here.” Here are six tactics you can use to improve those CTAs: ❶ Try the “Yes, and” approach — The reader’s just finished reading an email that they agree with — they’re already nodding their head “yes.” Now give them the CTA to have them take the next step: “Yes, I’ll support your work!” or “Yes, I believe in this mission!” ❷ Identify the value that readers care about most — There are a lot of things readers might value about your newsletter — this list can help you identify a few ideas — so mention those right in the CTA. For instance, if you’re selling a course or ebook designed to help readers overcome an obstacle, mention that here: “Let’s take the next step together!” or “Get the solutions you need!” ❸ Tie it back to a specific number — Let’s say you’re giving readers a special half-off discount. A great CTA might mention that: “Get 50% off now!” Or if you’re a non-profit offering matching funds, mention that in the CTA: “Triple your impact today!” ❹ Utilize two CTAs together — If there are multiple purchase options, try stacking two buttons on top of each other. An org driving donations might have one button with a link to donate monthly and another for one-time donations. A newsletter selling tickets to an event might have a button for general admission tickets and a VIP offer. ❺ Add an emoji or icon to the CTA — Don’t overdo it (too many 🚨🚨🚨 emojis might annoy readers), but an emoji that adds a bit more context could drive more clicks. You could also try adding something small, like an arrow emoji (→), as a reminder that there’s a next step. ❻ Adjust the design of the CTA — Test out different colors or button sizes to see if any make a difference. Or see what happens if you embed the CTA within a paragraph instead of using a button.

A few weeks ago, a reader sent me a note — and they had their own first name as their Gmail address. Not firstname.lastname@gmail.com. Not firstname75@gmail.com. Just firstname@gmail.com. Turns out they had a friend who worked on Gmail when it was first launching 20 years ago, and they were one of the earliest readers to sign up. I can’t ever recall being more jealous.

I was just re-reading this interview that Judd Apatow did with Mel Brooks for The Atlantic (https://lnkd.in/ewsidjbc). This latest interview closed with a fantastic back-and-forth between Mel and Judd: ——— Apatow: Your body of work is so enormous. How do you look at it now? Brooks: I don’t look back at it. I simply don’t. I just know that we did a lot of good things. Apatow: Well, there’s a quote from you where you said, “We should enjoy life; we should not *future* ourselves so much. We should *now* ourselves more.” Brooks: Yeah. Apatow: Has that always been your philosophy? Brooks: No, I just made that up at the moment. ——— The closing punchline aside, it’s that line — “we should not future ourselves so much” — that stuck with me. I know I’m guilty of getting ahead of myself and worrying about what might happen in a year or two or five. But I don’t know what will happen in the future, and neither do you. Stay in the moment. Enjoy the moment. *Now* yourself a little more.

We’ve got a great story this week on Inbox Collective — I talk with Zain Kahn of Superhuman, Quinn Emmett of Important, Not Important, and Pete Huang of The Neuron about how to build a newsletter that brings in $100k a year. But I owe a special thank you to Tyler Denk, Beehiiv’s CEO. He personally stepped in to make introductions and make sure we got the interviews to make this piece possible. Thanks to the Beehiiv team for their support of Inbox Collective this quarter — and a big thank you to Tyler for his help with this story. He went above and beyond for this one.