The 50,000-eyeball open rate—a newsletter story

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Chris Gillespie

How many content programs do you think survive their first year? What about their third? I’ll bet that curve looks much like that of new business closures, only briefer. Which is why I find myself so impressed with what Caleb Newquist, Editor-at-Large at the payroll software Gusto, has done with his newsletter for accountants. It has endured, grown, and become a fixture in his readers’ work lives.

His mailing “On the Margins” goes out twice per month to 100,000 accountants, certified public accountants (CPAs), and bookkeepers. Each time, half of them open. (Sometimes, as many as 60 percent.) And they don't just glance, they actually read—and “flock” to the links at the bottom. (That pun will make sense later.)

Who is Caleb? How big is his newsletter team? Can other marketing teams repeat his success? What sort of content operation is needed? Caleb shares all that and more in our interview, and spoiler alert, it all comes down to finding an author with a voice and letting them be.

Caleb Newquist is Editor-at-Large at Gusto, a 2,000-person HR and payroll software company. He’s on the PR team. If you’re also thinking of starting a newsletter and have questions, shoot him a note on LinkedIn. Also, here’s a Fenwick study on the subject.

I began as a CPA and frankly, just always loved writing

Caleb Newquist: I began my career as a CPA. I got a master’s in accounting right after undergrad and went straight into practice. But writing was always a thing I had my mind set to. I remember asking a senior person at the firm for advice on writing for practice journals, even though I really had no experience. I did end up writing an article for the Denver Business Journal which was quite gushy about the utility of an accounting degree, and a senior partner at KPMG wrote me an encouraging email saying I’d cast the profession in a positive light. I think if I went back and read it I would cringe pretty hard.

I switched over to writing during blogging’s heyday

When I started, blogs were the thing. People weren’t doing video or social media yet. It was blogs. You just heard about them everywhere, and people became well-known for starting them.

I began keeping a professional blog because I felt I needed something to express myself. That was very useful to me. I was reading a lot of great writers like Frances McKenna, Jim Peterson, Bess Levin, and the folks at The Intelligencer, and I took to that style of bloggy snark—gossipy and fun. That influenced me a lot. After I’d written maybe a dozen articles about accounting, I was connected with David Lat who wanted to start an accounting blog that would become Going Concern.

He said, “I like your style. That’s what we’re looking for.” And that was that. I became a journalist and wrote all day every day for three years straight.

This is when I started focusing on it as a craft, always through the lens of accounting. I was thinking about what accountants wanted to read about. Careers, trends in the industry, all those kinds of things. If I had to characterize that work, it was reading a lot and then getting those conversations I was having with myself down on paper.

My approach to writing really is that simple. I have these thoughts banging around in my head and I just get them down.

If you want good writing you have to pay for GOOD writers

If I think back to my time at Going Concern, which is a media property, publishing is a very difficult business. Very low margins. It is not for the faint of heart. Hopefully, you have some money to burn. But what I took away from it is if you want quality, you have to pay for writers.

I think a lot of people have the attitude that writing is just a commodity. Lots of people can do it. But how many can do it really well? You need someone who has a voice, and that’s actually quite rare. Someone who’s just naturally prolific. Who can pound out 1,500 words in an hour and a half and not think much of it. And you read it and think, wow, this person has something to say.

"You need someone who has a voice, and that’s actually quite rare."

The hard thing is identifying people who are saying interesting things and giving them a shot

I think this is what people find most difficult about starting a publication—asking, “Who seems like they have something to say?” And identifying those people and giving them a shot. I owe my entire post-accounting career to this guy I mentioned earlier, David Lat, who’d written at this big political blog. He started out writing this anonymous blog while working in a U.S. Attorney’s office called “Underneath Their Robes” about judges. They found him out and he got in trouble. So then we went on to found Above the Law and he’s made a real interesting career for himself.

When he wanted to start this accounting blog, I was nobody. I had just moved back to Denver from New York. I’d been laid off during the financial crisis. I wasn’t from the East Coast. I didn’t have a fancy education. But they liked my work and gave me a chance.

If you want to start something, you need someone who has an eye for talent

Let’s be clear, I’m not suggesting you replicate my situation. But you do need that person on your team who’s going to recognize that voice in others and say, “That’s it. That’s what we want.” Someone with an intuitive eye for talent.

That’s what brought me here to Gusto. The Chief Marketing Officer here at the time, Tolithia Kornweibel, noticed the freelance work I was doing for Gusto and said, “I’ll be in Denver, want to grab coffee?” It’d be interesting to get her perspective, but I recall her basically saying, “That’s what we want. We want more of that here.”

Find the right person and let them be

After you identify someone with a voice, the second really important thing is you just have to let them do their thing.

At Gusto, once we landed on the name “On The Margins,” we set ground rules and people left me alone to do what I do. That was huge because I never felt creatively restricted. I had what felt like full autonomy. I got to write what I wanted to write.

Because, you can’t tell a person with a voice what to do. You have to let them be. I don’t know. Is it really as simple as that? I think it is. But it is so hard and so rare. Lots of companies like to talk about how they’ll do it, but you actually have to do it.

"You can’t tell a person with a voice what to do. You have to let them be."

How’d we get to 100,000 subscribers? We cheated, honestly

We kind of cheated to get to that number, to be honest. We cheated in the sense that an early conversation we had was that we wanted the newsletter to be quickly splashy and notable. Someone on the team pointed out that accountants agreed to receive emails from Gusto when they signed up. What if my newsletter was one of those emails?

I was very conscious that nobody likes to be thrown onto a list. People have mixed feelings about that approach. I had mixed feelings. But I also didn’t necessarily want to build it completely from scratch, and there was some urgency around getting it out there quickly.

So we compromised and had people receive a really clear email saying, “Look, here’s what this is, here’s why you’re getting it. If this is not what you want, go right here and you’re off, no problem.”

Most people stuck around. In the early days we were seeing open rates in the 20 percent range, and we were getting lots of good qualitative feedback from direct responses. A great majority was positive. The unsubscribes remained low, we purged the list of inactives from time to time, and it just grew.

You must decide what kind of newsletter you want

If you read newsletters, you probably have an idea of what you enjoy. Like most people, I write things that I’d want to read. That’s the voice and tone of it. From there, you need a theme or topic, and that should be pretty obvious because hopefully you’re already reading a lot about that stuff.

The ideal thing is to land on a subject matter expert who wants to write. I wouldn’t call myself an accounting expert but part of my appeal was I was an accountant, then blogged about accounting. That gives you a broad understanding of all you’re supposed to write about, and taste for what’s interesting.

I guess none of what I’m talking about is any different than being a fiction writer. If you read Stephen King’s book On Writing, he says, “The best way to become a good writer is to just read, read, read, read.” Same deal.

Your newsletter is a news service. Simply find the right things for your readers

There’s definitely a place for newsletters that are simply collections of things you should be reading because the internet is vast and full of garbage. Finding good stuff to read is hard. And if your readers don’t have a lot of time to do that, and they trust your take, and you do it in an engaging way, you’ve got it. Those are the ingredients.

Though for me, my writing is very much focused on editorializing. And the newsletter is fairly long.

We do look at the performance based on what people click and sometimes the most popular links are all the way at the bottom, so we know people are reading through.

Put the funnest links last

The funnest links are always at the bottom. That’s something I just learned over the years. You don’t put the most interesting one at the top because then people won’t read to the bottom. There’s a method to that particular part of the madness.

As for where I find those, a lot of times, it’s in other newsletters. Twitter is a good source for a lot of stuff too. I find myself linking to pictures of birds right now because I love birds, and there’s just so much great bird photography on Twitter, and I’m just like, “Look at this kingfisher. This is so cool.”

The rest is just from the serendipitous nature of the internet. Remember StumbleUpon? I don’t even know if that’s still a site or not, but you’d just find the strangest things. That kind of discovery is what makes the internet fun and good.

From a recent issue of On the Margins

Operationally, it’s quite simple. It’s a Google Doc, a person, and an email

In terms of running On The Margins, it’s mostly just me. There are lots of people I can ask for things, but I’m very self-reliant. I ran a very small blog operation that serviced a lot of readers so I’m used to being self-sufficient. In fact it’s actually better if it’s a smaller operation. Sure it’s a lot to ask of one person. But there’s also usually someone who wants the job.

We also memorialized its purpose at the outset so if anyone came around from marketing and said, “Hey what’s this all about, can we change it?” we could say, “Well these are our guidelines and this is why we do it this way.” If there’s strict guardrails and they’re written down, the person running maintains their autonomy.

To actually write it, I start with an empty Google Doc template and just start reading things. Or if it’s early in the week I’ll bookmark things and save them for later.

The newsletter goes out on Friday, so Wednesday’s are my big newsletter days. I draft it. An editor reviews. I run everything through Grammarly. One of my worst writing tendencies is I omit articles and Grammarly makes my writing much cleaner than it used to be. Then I also use Hemingway Editor because I like that they have different approaches to copy. Grammarly is a catch-all whereas Hemingway is like, “Is this punchy?”

And that’s kind of it. Load it in Marketo and schedule it.

Sure it’s a lot to ask of one person. But there’s also usually someone who wants the job.

"Sure it’s a lot to ask of one person. But there’s also usually someone who wants the job."

On the side, Caleb also hosts a podcast called “Oh My Fraud”

My buddy Greg Kyte and I have been creating stuff together for 10 years now. We just know each other very well. Greg is still a CPA, but he’s also been a standup comedian. The chemistry we’ve developed in those webinars had us thinking we should try something else too. We’re the classic comedy duo. I’m very much the straight man and he’s the joke guy.

True crime is having a moment—I mean, it’s always been a thing since Truman Capote, but true crime for accountants seemed like the thing. They can’t get enough of that stuff. Fraud is catnip to accountants. I pitched Greg on the idea, we found a distribution partner, and it came together.

I’d never tried a podcast because of a fear of failure. I didn't want to fail at that. It made me really patient for the right thing. Right time, right topic. A lot of luck. But also just, recognizing the topic when you see it.

Listen to Oh My Fraud →

A recipe for building a successful newsletter

If I were to summarize everything I’ve learned from Caleb, I’d say you need:

A subject expert who wants to write
A topic and a charter about what it’s for and how it works
Google Docs
An editor
An email tool
A starting email list
Someone to build the emails
To read, read, read, read
To write 15 versions of every headline (read Caleb’s for inspiration)

Want more? Here’s study of 100 newsletters by Fenwick →

Want to read more of Caleb’s writing? Follow him on LinkedIn.

His one piece of advice will surprise no one: Write. “It’s the best way to get good. Not much more complicated than that.”

Also, check out this dark-eyed junco.

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