Dan Oshinsky’s Post

A big shout-out to Stephanie Griffith, whose Email Preview tool (https://emailpreview.io/) is absolutely indispensable when it comes to saving emails. I can't tell you how many times I've used it this month, and how many times clients go, "Wait, there's a magic tool that can take my newsletter and turn it into a .pdf???" Bookmark it, use it (and maybe buy her a coffee too as a thank you for such a great free tool!). p.s. if you do want to buy her a coffee → https://lnkd.in/eXbeu78i

If you deliver your email at the wrong time, you’re significantly less likely to get a response or the action you’ve requested. And that’s an issue. It’s why I use the 7-to-7 Rule — I try to send emails only between 7 a.m. and 7 p.m. Why? Some clients check email before 7 a.m., and some do it after 7 p.m. But for most of my clients, they’re not going to act on something if it’s sent outside that window. My goal is to send email during that window where they’re most likely to be on their work email and ready to take action on whatever I’m asking. Does it mean I don’t check email after 7 p.m.? Actually, no! I usually do a quick scan of my email first thing in the morning, and I’ll hop onto email in the hour before bed. The only catch is: I won’t send the email until 7 a.m. the next day. When it comes to the 7-to-7 Rule, Gmail’s scheduling feature has been an absolute gift. If I realize on Saturday morning that I have something to ask a client, I’ll write the email immediately but schedule it for Monday at 7 a.m. The result? More of my emails get answered at a time that’s convenient for both of us — and when we can move quickly to get the work done.

A well-built landing page can help you grow your newsletter faster. Let’s look at a few of my favorites, including those from: Tom Alder’s Strategy Breakdowns The Atlantic Chenell Basilio’s Growth in Reverse The Wolf of Franchises Dense Discovery Boktugg AB I think you’ll find a lot you can learn from these seven pages — and hopefully a few things you can bring back to your newsletter’s landing page!

OK, storytime... When I started at The New Yorker, I quickly ran into an issue: On major holidays, our team still wanted to send out our daily newsletter, but we didn’t have the editing or staffing to put together a newsletter on those days. The solution: We put together a special holiday send of the daily, where a handful of writers would recommend feature stories they liked. We could get the copy written and schedule the email well in advance, so it worked well for our team. But one year, I made a mistake: I was finishing the newsletter on a Friday afternoon before a long holiday weekend, and I accidentally typed in it’s instead of its. The copy editors caught the error, but I forgot to fix the typo before scheduling. Worse: The error came in a paragraph that was originally written by a senior editor of the magazine. When I got back to the office after the holiday, we had dozens of emails from readers, many of whom said, with no exaggeration, that they weren’t sure if they could trust a newsroom that could make such a mistake. Some threatened to cancel their subscription. I was at The New Yorker through a few controversial moments, but I never personally saw our audience as angry and upset as they were after my typo. It was a small mistake, but for some of our readers, it was a significant one. We decided not to send a correction out to the full list — plenty of readers missed the mistake or never opened the email, and it felt odd to call attention to a typo — but I did work with our team to craft an apology email, and sent it every reader who’d written back. Minor email mistakes like this happen all the time. Some require a big apology email, and some require smaller steps. (But remember: “its” is the possessive one!)

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.