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Happy Tuesday! This week features a guest interview featuring my friend Jessica Lackey of Deeper Foundations.

If you don't know Jessica, she is a business growth strategist for expertise-based solo business owners. This quote from her About Page sums her up really well:

Jessica has one of the best newsletters geared toward solo business owners.

It's deep, thoughtful, and nuanced, the kind of newsletter that you read while sipping your morning beverage. I've been a devoted reader since she first suggested that we do a newsletter swap almost exactly three years ago, and I've missed maybe two newsletters since I subscribed.

Rereading her responses, it's interesting to see how how her newsletter has evolved over time, and how her approach is so deeply connected to all aspects of her businesses. It's also giving me some ideas about how I can strengthen my own approach and deliberately weave in my frameworks and methodology that I established at the beginning of the summer.

Here are some of my favorite takeaways from Jessica's interview:

• Newsletters as a "body of inquiry" vs. a weekly content obligation
• Approaching newsletters as a way to diagnose a topic and publicly workshop your ideas
• People quoting back to you your ideas as a way to show that your newsletter is "working"
• How newsletters can benefit not just the people you're trying to market and sell to

What inspired you to start a newsletter, and how did you settle on Kit?

I've always wanted to write a newsletter. I've been writing about once a week since 2018, starting with my very first blog, Jessica's Wellness Corner, which was a nutrition blog. Then it became a life coaching newsletter that I sent weekly through Mailchimp from 2018 through 2021, before I transitioned to business consulting.

I moved to Kit in March 2022, when Mailchimp became increasingly unusable for me and started raising its prices. At the time, I'd seen people talk about ActiveCampaign, and I'd been in the back end of ActiveCampaign enough to know it was too much for what I needed. This was also pre-Substack becoming what it is now. Kit was the creator option that was the clear choice.

Who is your newsletter geared toward?

My newsletter is geared toward the expert business owner: coaches, consultants, and service providers who increasingly need to build the business and the business ownership skills around their expertise.

It's usually a 1,000–1,500 word essay every week deconstructing some aspect of how expert businesses work.

I'm not necessarily writing for someone who needs a quick marketing tip. I'm writing for someone who wants to understand the business they're building: how the pieces fit together, why something isn't working, and how to become as skilled at owning the business as they are at practicing their craft.

How often do you send your newsletter? How did you end up at this cadence?

I send my newsletter once a week, at 10:00 a.m. Eastern every Sunday.

A week works because it’s enough time for me to think about the newsletter, notice what's happening with my clients and members, and formalize a point of view.

I'm usually thinking about three or four different topics at any given time. But more importantly, I'm almost always thinking about a series.

That's become a defining feature of how I write.

Right now, for example, I'm revisiting my point of view on business models. In 2023, I came up with seven different business models for expert businesses. Three years later, I'm revisiting those models one week at a time: Where's the nuance? What did I miss? What needs to be explained differently now?

Before I started writing the series, I had a nine-part arc constructed in advance.

Earlier this year, I did something similar by revisiting the six systems in a business and asking what had changed in my thinking about each of them.

(Note from Bev: You can catch up on Jessica's past newsletter series here.)

And when I'm launching something, I'll often do a series leading up to it. But it's not really a "launch sales series." It's a “let me excavate my thinking around this topic in a deeper way” series.

Instead of treating a newsletter as a weekly content obligation, I can treat 4, 8, or 12 newsletters as a body of inquiry. I can start with a hypothesis, explore it from multiple angles, discover where I'm wrong or where there's more nuance, and come out the other side with a much more developed piece of intellectual property.

How has your newsletter and content evolved over time? How has writing it informed your work?

The newsletter used to be observations I was having, things I was thinking about, and occasionally rants I needed to get out of my head.

Over time, it has become increasingly a way to interrogate my own intellectual property and support my other creative projects.

For about two years, for example, I was essentially writing my book through the newsletter. I wasn't publishing chapters of the book, but I was taking ideas I thought would support those chapters and exploring them in essays.

The writing became illustrations. Those illustrations became things I would teach. The teaching became YouTube videos. Those ideas ended up back in the newsletter and eventually back in the book.

It's a loop.

When I started writing, the newsletter was much more "what Jessica thinks." Then it became, "How am I articulating the ideas that might become this book?" Now it's increasingly, "I'm diagnosing a topic. How do I use the essay to workshop my ideas in public through a serialized lens?"

It probably took me three or four years of consistent writing to understand what my body of work was actually going to be.

How do you measure whether your newsletter is "working"?

Replies are great, of course.

But one of my favorite measures is when people in my programs or membership quote "me back to me."

They'll use a phrase I've used. They'll reference a framework in talking about their own business. They'll bring an idea from an essay into a coaching conversation. That's how I know people aren't just opening the newsletter; they're integrating the ideas.

One of the nice things about having a membership and a long-term client base is that I'm not only writing to generate new sales. I'm writing to my current customers and clients, too. I'm sending them things they need to hear, things they need to know, and new thinking that will help them do their work better and it arrives on schedule every week.

So I think of the newsletter as being for my whole audience, not simply as a marketing tool.

That creates an interesting challenge, though.

After six years of doing this work, I've developed a lot of frameworks and shorthand. My longest-tenured clients and readers know exactly what I mean when I use them. A person who subscribed last Tuesday doesn't.

So I'm increasingly thinking about the infrastructure around the newsletter: How does my welcome sequence orient someone to how I think? How can my blog, Kit sequences, and YouTube channel help a new reader understand the canon of my work without requiring me to stop pushing my thinking forward for the people who have been reading for years?

That's one of my next projects: not just having a welcome sequence, but creating "best of" guides and sequences around different bodies of work. A new reader could get the foundational thinking—the original canon—and then dive deeper if they want to.

In addition to inviting people to sign up directly for your newsletter, you also offer a free email course. How did you decide on an email course as a "lead magnet"?

I want people to sign up for the writing, not a freebie. So if they aren’t interested in the newsletter and the writing in and of itself (which I want to be so good they want to share it!), they might not be my reader or my client. Most people who see the newsletter page directly actually came from low volume Meta ads actually about the newsletter, so they’ve already seen some of my copy and my work.

I think having a way to quickly indoctrinate, for lack of a better term, someone into my way of thinking using an email course is a wonderful way to increase the amount of time people spend with my work at the outset, which often reduces conversion time. It’s also promising a concrete outcome which is more impactful than just “sign up for my newsletter.” (And spoiler alert? I’m switching it up now so that my Welcome Sequence to the newsletter is just the email course, regardless of the packaging).

(Note from Bev: Sign up for Jessica's Email Course, The Predictable Revenue Roadmap, here.)

Take it one step at a time,
​Bev