Writing A Winning Newsletter with Dan Oshinsky

Using email to build meaningful, engaging relationships with your audience


Dan Oshinsky, former Director of Newsletters at The New Yorker and BuzzFeed and founder of Inbox Collective, an email consultancy, joins Stew Fortier to discuss how to harness the power of email to build engaging, meaningful relationships with your audience.

The summary below was prepared for Compound Writing, a paid invite-only community of online writers. Apply here

1. Email drives impact that other channels can’t match. 

Email is so ubiquitous these days that it’s easy to overlook how powerful it can be when it is executed well. Dan has dedicated his professional career to the optimization of email and is continuously impressed with its dynamism.

“The thing that always amazes me with email is just how much of an impact it can have, even if you don't have the world's biggest audience. For me email was just one of those tools where it was such a powerful way to actually have real conversations with folks.”

Dan reiterates that in order to do email well, you have to acknowledge that email communications are, in essence, a relationship.

“It's got to be more personal, it's got to be more curated, and it's got to be really powerful and useful. It also has to be a little more conversational. I want to have emails in my inbox where people are asking me things and giving me a chance to reply. I want to start a conversation. I want to learn more about you and give you the chance to learn more about me. The people who take advantage of that relationship part of email, the conversational part of email, tend to do really well."

2. If your newsletter is for everybody, it’s really not for anybody.

To grow a successful newsletter, Dan believes in defining your audience as specifically as possible.

“Usually, if your newsletter is for everybody, it's really not for anybody. Having a really specific audience in mind and knowing how you uniquely serve them is really important. People tend to miss that. Their product is just too general” 

He stresses that the most important question you can ask yourself as a writer is how you provide value to your reader.

“You really have to earn your place with your readers. Ask yourself ‘Why would they spend their time on this thing?'"

3. Do non-scalable things to get your first 1000 subscribers. The long-term returns might surprise you.

While it’s natural to want to grow your newsletter quickly, Dan encourages writers to really put in the personal legwork for the first one thousand subscribers.

“A lot of what you're doing at the start are things that don't scale. A lot of it is personal outreach, having conversations on other platforms, doing press, doing media, and thinking about the stuff that allows you to get to that first one thousand true fans --  the people who have a relationship with you, have spoken with you, know you and trust you. Once you're there, then you get into the fun stuff of being able to grow, like trying a referral program in your newsletter or creating some sorts of lead magnets.”

Those relationships that you build in the early days of your newsletter have the power to yield exponential growth over time. Dan reminds fellow writers:

“...as you scale and grow, your audience does a lot of the work for you in being evangelists for your product. The really hard part is the first thousand or two thousand people. You have to get to scale before you can expect your audience to do some of the legwork for you.” 

Learn more about how you can join Compound Writing, a paid invite-only community of online writers.

4. Introduce yourself to your readers with a well-crafted onboarding series. 

If there’s one thing that Dan believes most newsletter writers should set up, it’s a strategic email onboarding series.

“The welcome series is awesome because it does a number of important things. First, it allows you to build a real relationship with your audience and tell your audience what you’re about. The best onboarding series are all about just telling a story of who you are and what you’re about over the course of a couple of weeks. Secondly, an onboarding series is really good at converting people to supporting your work. If you're asking people to subscribe and pay for something, become a member, etc, emails are really, really good. That onboarding series is a great way to get people from point A to point B."

What is one of Dan’s favorite things about an onboarding series?

“It's automated! It does these things in the background for you while you're sleeping.” 

5. Collaborate with other writers to create something that is greater than the sum of its parts. 

Although Dan currently works solo, he acknowledges the benefits of collaborating with other writers to create a high-value product and avoid burn-out.

"Right now we're seeing a couple different writers or creators collaborate together, and this makes a lot of sense to me. It allows you to expand your reach, gives you a support network that's built-in, and it means that you are not the solo person doing this thing.” 

6. “Email is the duct tape of the internet.” 

At the end of the day, Dan encourages everyone to appreciate the fundamental power of email.

“Email is kind of like the duct tape of the internet. It just works. It always seems to work. It's never the sexiest thing in the world, but it does its job really well.”

You can learn about Dan Oshinsky and his published works by visiting his website. You can follow him on Twitter here.

Next cohort starts
May 1st

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.