How to Produce a Weekly Newsletter

Illustration by  Venetia Berry

Illustration by Venetia Berry

Body of Work 

Last week, to celebrate my own birthday and the one-year anniversary of the Underwire newsletter, I took myself to the Olympus Spa. 

Legendary in the Seattle area, the Olympus Spa is a Korean-style jimjilbang, or women-only bathhouse. This spa is known for two things—full nudity and the body scrubs administered by Korean ajummas, the “aunties” with the no-nonsense warmth and authority.

At Olympus Spa, the heart of the experience is the bathhouse with soaking pools, a sauna, and steam and scrub rooms. This is the place you go to level set and reconfirm that despite how fucking hard it is to run a business and do anything different and worthwhile, you're probably doing just fine.

While you’re soaking in the pools, you pretend not to notice everybody else. This is hard to do because it's ALL on display in the bathhouse. Full nudity is the great female equalizer. It's comforting to notice that even the tautest twenty-something jiggles on the scrub table. 

Just as there is no “perfect” body, there is no perfect business. 

Remove the armor of clothing and identity and we are all lumpy, droopy, soft and tender.

That founder that gets all the media attention and seems to be everywhere, all at once? Probably has saggy ops. 

The bootstrapper with a steady revenue stream? Yeah, she’s got killer upper arms AND her boobs still skim her belly. 

You are where YOU are with your business. Hang in there. And remember, it must be jelly cuz jam don't shake like that! 🤣


Naked 

Since April 24, 2018, I’ve produced 37 issues of Underwire. From the outset I wanted to use the newsletter format to find my voice as a feminist businesswoman and determine if there's a business model in here (working on that for year two). 

I’m proud of this body of work. I didn’t grow my subscribers as fast as I wanted. But I nailed my goal of consistent production. I went weekly in September. 

For your content marketing efforts, I thought it might be interesting to read about the tools and process I use to produce Underwire.

Content Production

  • Every issue begins in Bear, a note-taking app that collects my ideas, links, screenshots, etc. I pay for Bear because of the interface and organizational structure.

This how I track the funding. Throughout the week I add updates in the precise format they’ll appear on the newsletter and website. This was last week's update. This info also gets tracked in a Google Sheet.

This how I track the funding. Throughout the week I add updates in the precise format they’ll appear on the newsletter and website. This was last week's update. This info also gets tracked in a Google Sheet.

  • Each day I read the Crunchbase, Term Sheet and GeekWire newsletters for funding announcements. I verify funding updates in the Crunchbase app on my iPhone. 

  • I track all female-founded VC fundings, as well as exits, in a public Google Sheet. I have not seen another comprehensive listing like this that’s free. Frankly, it’s a pain in the ass for me to do this, super time consuming, but it’s important. If one woman gets VC funding because she sees an investor on this list, or makes an important connection, then it’s worth it. 

  • I also read widely across mediums for issue inspiration. One of my favorite places for inspiration is the Everett Public Library. They have an impressive array of periodicals and art and business books. I regularly sit myself in their gorgeous barrel-vaulted reading room with a stack of materials and plan future “Ifs” issues. 

  • Every Monday morning by 8am I open Mailchimp, copy one of the custom templates created by the incredible human Hannah Templer, and write the words that appear in each issue. I often create a first draft in Word, but I always finish editing in Mailchimp. 

  • While writing each issue, I listen to my Mellow Groove or Underwire Spotify playlists, cranked loud, especially when this song comes on. Somewhat of an anthem. 

  • For graphics, I use Canva. Their paid version allows you to create a Brand Kit with your fonts, color palette, logos and other core graphics. Canva isn’t as robust as Adobe Photoshop (very expensive) but it’s fun to use and works just fine for now. 

  • Prior to hitting “schedule” in Mailchimp for 11:45am Monday delivery, I upload the issue to Squarespace. I moved away from Medium for issue archiving at the start of 2019 to improve my SEO. This was a key lesson from Ren and Will at Otis Solutions, who are helping me with a new offering for 2019. BTW, Medium sucks your SEO juice. 

  • After an issue is live, I cross post to LinkedIn (usually on Tuesdays) and Instagram (throughout the week). I’m not personally on Facebook, so I’m sporadic on posting Underwire there. LinkedIn is the best channel for direct engagement with readers.


A few more of the generous and talented people who helped to create the Underwire brand:  

  • Stephanie Mennella designed the logo and pushed me to find my unapologetic voice. 

  • Gabrielle Goldman built my visual identity and brand style guidelines, which were the best early investments made in helping to bring consistency to everything I do. 

  • Kate Reingold took Gabrielle’s work to the next level, refining the website and interpreting the brand into illustrations and Canva templates. 

  • Nicole Proctor inspired the Polaroid style for the CEO photography and shot most of the profile stories.


The moodboard that jumpstarted the Underwire visual identity.

The moodboard that jumpstarted the Underwire visual identity.

The one-page Underwire style guide that I use all the time.

The one-page Underwire style guide that I use all the time.


Top Issues by Open Rates

1. Retail therapy — 70.6% 

My “mad as hell” moment. The most emotional issue, by far, which is not easy for me because I’m private and generally believe that my white privilege isn’t all that interesting in the grand scheme of things. From this I learned that the stronger emotions lead to better engagement with readers. 

2. Vacation — 63.4%

Fruit of our labor, also happens to be my favorite issue because it features the Peach Madre CEO and it's when I connected in my own head how many of us there are out there. 

3. Tits Up — 60.3%

Part 2 of asking for help, wherein I detail HOW to flex the Ask muscle, in addition to quoting Twyla Tharpe and correlating our work to that of Midge Maisel from The Marvelous Mrs. Maisel. 

4. Bumps — 61.6% 

The pregnancy issue featuring the Zephyr Teachout ad from the 2018 New York Attorney General primary race. I broke down how to create a brand that stands for something. 

5. Aretha — 58.9% 

An obituary for Aretha Franklin, wherein I learned that she always got paid upfront before performing. I will never forget that. Not all of us are in a position to demand that, but I will continue to push myself and others to ask for what they deserve.


Final Insight 

The CEO Profile open rates are far lower, averaging 35%. I keep doing them because I believe we're going deeper with their stories than other media coverage. 

I think these issues are lower performing because of the high word count. Tons of wisdom if you take the time to read them. I'll eventually get all of these on the Underwire website and SEO the shit outta them to help with long-tail visibility. 

I’m astounded by what I’ve learned from these conversations. Look at the incredible women I talked with last year!

Clockwise from upper right: Kristen Miller (Stylyze), Laura Clise (The Intentionalist), Richa Prasad and Lucy Liang (Coach Viva), Nancie Weston (Raiin), Michele Mehl (Excy), Dani Cone (Cone & Steiner), Jana Kleitsch (Wanderlust Society) and Sarah LaFleur (MM. LaFleur)

Clockwise from upper right: Kristen Miller (Stylyze), Laura Clise (The Intentionalist), Richa Prasad and Lucy Liang (Coach Viva), Nancie Weston (Raiin), Michele Mehl (Excy), Dani Cone (Cone & Steiner), Jana Kleitsch (Wanderlust Society) and Sarah LaFleur (MM. LaFleur)

Underwire