Serving Writers & Restaurant Workers Through "In The Weeds" 🍽️
A new series about newsletter operations, starting with Kailey DelloRusso
Hello Bleeders!
I’m in the midst of a March residency for
all about newsletters. My official stance is that every writer should have a newsletter, so hopefully, this course helps you wrap your head around how to start, optimize, and grow yours. Head on over to the Substack to catch up and subscribe to receive upcoming lessons in your inbox.As a supplementary series, I tapped a bunch of my favorite newsletter writers to share their trade secrets, and I’m going to run Q&As with these brilliant newsletter purveyors RIGHT HERE.
Today, we’re kicking things off with Write or Die founder
, who you may recognize as a former guest on The Bleeders.Kailey’s also the founder of a newsletter/podcast called
. Let’s go behind the scenes.
What’s the basic premise and tagline of your newsletter?
KD: In the Weeds is a newsletter where I dive into the process of writing my first novel while also working in the service industry, specifically waiting tables at a country club.
Tagline: “Untangling the writing life while working as a waitress.”
When and why did you start your newsletter?
KD: I started In the Weeds in January of 2023, but it wasn’t until a few months later that I started posting more consistently. I wanted a place where I could be honest and shed light on the often stigmatized yet incredibly flexible roles in the service industry, like bartending and waitressing—a world I have been a part of for over ten years. These jobs, often labeled as 'dead-end' or 'not real'’ are, in fact, lifelines for many creatives like me, providing the financial stability and flexibility needed to pursue our artistic endeavors. But we still seem to shame people for working them! I wanted to talk about making money while writing. The service industry is funny and fascinating and filled with story ideas, so I knew I would have some content to work with.
Who’s your main audience?
KD: Writers from all different stages of their career.
How is your newsletter differentiated from the other newsletters in your niche?
KD: Although I talk about the writing process and novel writing, I also talk about jobs and the balancing act of managing your creativity with practical demands like making money. I don’t see many writers talking about how they make ends meet through jobs often viewed as menial or low status—the grunt work like waiting tables.
I recently added a podcast to the newsletter where I have candid conversations with published authors about their time working service industry jobs and how that intersected with their writing life. It's a blend of industry talk and deep dives into the creative process, shedding light on the less glamorous but equally important aspects of a writer's life. It's been so fun so far!
What’s your editorial strategy? Including: What kind of content are you focused on offering? What’s your publishing cadence? How far in advance do you plan your content calendar?
KD: I aim to post every Wednesday. This has been a recent strategy for me as I’m trying to be more consistent with my posts. The only part I plan out far ahead is the interviews for the In the Weeds podcast. Those need to be scheduled, executed, and edited, so it takes a lot of time. Plus, I only post those monthly. For written content, I don't want to be too prescriptive. Since so much of what I write about is my novel writing process and how I keep the creative process alive, I find that my best pieces come when I just follow a curiosity or an idea that comes to me on a whim. Or sometimes, something funny or ridiculous happens during my waitressing shift that I could never have planned ahead of time to write about. I try to plan my months ahead of time, but to be honest, it rarely happens.
I focus on offering novel updates for those who are interested in seeing my process for writing my first novel, restaurant stories, conversations about work, and monthly podcast interviews.
How many subscribers do you have?
KD: I run a few other Substacks for Chill Subs x Write or Die and between all of them, it's about 15k subscribers.
Do you offer paid memberships?
KD: I have some ideas brewing about paid content I would like to offer. The In the Weeds community has grown consistently over the last month and I’d love to offer them more ways to engage with me and one another.
Have you tried any other methods of monetization?
KD: I haven’t yet.
Tell us about your newsletter’s growth trajectory. What have been the most effective ways for you to promote your newsletter? Did you have any growth spurts, and what did you learn from those?
KD: It was slow until I caught my stride and understood more about what I wanted to write about and what my readers were interested in. When I began to post consistently on Wednesday, it felt like I saw a lot of growth there. I have also found Notes to be an amazing resource. In my experience, if you are authentic and engage with others, people are more likely to follow you and see what you write about. I’m also a member of
’s community and she provides weekly threads to get conversations going. In one such thread, I posted, commented, and met a lot of interested people. My subscriptions went up substantially in just one weekend! Notes is my go-to for promoting and finding others to read and follow.What’s been your most popular content, and your guess as to why?
KD: My most popular content has been my posts about writing my novel. I recently finished my 4th draft and have been very transparent about my ups and downs, the goalposts I have moved, the failures I have encountered, and how my process has changed in the three years I have been working on it. I’m personally obsessed with reading about other writers' processes, so I think I’m not alone here. Writing can feel so lonely, and I think it feels good to see other writers struggling or questioning or succeeding like you are.
How has your newsletter served your career as an author?
KD: The novel I’m writing is centered around working in a country club restaurant. My hope is that writing about my process and the topic of working grunt jobs to make ends meet while working towards a literary career will help engage the types of readers who will be interested in my book when it gets published. (I’m only sending out positive vibes! Yes, when it gets published!) So, right now, it's serving as my author platform community builder!
What’s your #1 tip for writers who want to start a newsletter?
KD: Just do it. I tell everyone to start a Substack because I think it's one of the best things on the internet right now. It keeps you writing, it keeps you consistent, and it allows you to explore the things you are obsessed with. I’m thrilled I get to talk about waiting tables and how I hate outlining and how hard yet wonderful it is to write a novel. Thinking of what I’ll share next brings so much joy to my days. If you have an idea for a newsletter, follow it. You don’t know how it could evolve and what you will learn about yourself as a writer along the way.
What’s your #1 tip for writers trying to grow their existing newsletter?
KD: Engage with others! Comment authentically. Read other newsletters and share your favorite quotes with a personal anecdote. Find ways to collaborate with newsletters that have bigger sub counts than you. It's all about community, baby.
Shout out another writer-newsletter that you admire and enjoy consuming.
KD:
by
: For those obsessed with the writing process, Danielle is your girl! Her Revision Season series took us through how exactly she revised her entire novel. So. good.by : Brittany shares a lot about her writing life and how she balances it through motherhood and teaching. She’s funny and honest and writes so beautifully.
by : Laura’s newsletter is a countdown to the publication of her debut novel, where she takes us through the entire process.
Anything else you’d like to add?
KD: Check out my podcast episode with
! She talks about how working as a waitress and a barista shaped her path as a writer and so much more.Thank you, Kailey!
Give her a follow on Instagram and, of course, subscribe to
.To catch up on the newsletter course thus far, check out the following posts:
Introduction: Start with Why
Lesson 1: Premise, Purpose, and Market Fit
13 Newsletter Creators Share Their # 1 Tip for New Writers
Lesson 2: Who's Your Who? Identifying Your Target Reader Avatar
Summer Brennan on Her Dangerously Good Newsletters and How They Serve Her Writing Career
Lesson 3: What to Post in Your Newsletter
Lesson 4: When: Editorial Calendar and Cadence
So… ROLL CALL! 🗣️
Do you have a newsletter? If so, let’s connect! Drop your link in the comments below.
Let’s connect on social media! I’m @courtneykocak on Twitter and Instagram. For more, check out my website courtneykocak.com.
 | A guest post by
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Restaurants x Publishing is very much my niche. Can’t wait to learn more about you and your novel, Kailey!
Thanks for the shout out, Kailey!