Wander Wealth

I put a question in my chat on Friday and got 51 answers, and it took me until about the twentieth one to work out that Iā€™d asked it badly. The question was simple. Where are you in your Substack journey, and where do you need help? Five options. Growing your audience. Creating offers people buy. Marketing and distributing your content. Understanding the platform. Converting free to paid. 70% of you picked number one.

More people ask me this than almost anything else: Should I start a second publication on Substack or just keep one? It comes up in coaching calls and in my DMs most weeks. I’ve been answering it all year while living the messiest possible version of it. Right now, I run two publications at the same time myself. I started Wander Wealth in spring 2024 and my second, Level Up with AI, one year later in spring 2025.

This morning I did one of my live Substack audits, the “how I’d improve your Substack” Glow-Ups I run for paid members. This time I did it for Margaret South. Here’s what came out of it, and most of it applies to almost every publication I look at. Don’t hide behind the paywall. If the first thing a new reader sees is four paid posts out of five, they leave before they know you. Keep a free Start Here post, pin it, introduce yourself, and make it easy for someone to get in and read.

I jumped on a spontaneous Substack Live this Monday morning. A call fell through, I had 15 minutes, and honestly these impromptu lives are some of the best things you can do here. So I hit go. We covered a lot for a short one. Someone asked how to convert free subscribers into paid ones. My answer: focus on the transformation, not the features. Give people something they can use the moment they upgrade, mix in a social element like a chat or a live, and where you can, add a bit of personalization.

A follower wrote a comment to one of my Notes recently and said something that stuck with me. They told me they don’t subscribe to people on Substack anymore. Too many emails, too overwhelming. But they follow the writers they like, and they trust that the posts will show up in their feed when it matters. That’s how they read now. My first instinct was to think of that as a problem to solve. Then I realized it isn’t one. Here are my two numbers.

Yesterday I had another live audit with one of my paid members. Yay! This time I sat down with Courtney Cunningham ✨, who writes Not a Niche — a publication built on the refusal to niche down. She shares the stories she’s lived and the lessons (really, the reminders) that came from them. She just crossed 1,000 subscribers, so we dug into what could take her further. What Courtney’s already doing well: Her notes are strong.

Two years ago I sat with a notebook and tried to write down everything I didn’t know about growing a newsletter. The list filled three pages. How often to post. What to write when nobody’s reading. When to turn on paid. What to charge. Why some posts bring 40 subscribers and others bring 2. You get it. The list is endless. I had to figure out every single line the slow way, one experiment at a time, 159 published issues and counting. A few weeks ago I finally did something I’d been putting off for a year.

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This week I sat down live and went through Nnamdi’s publication, Worlds Collide. He writes about what happens after you move to a new country, the systems and pressures nobody warns you about. A year in, 1,100 subscribers, and with pretty good engagement on every post. The full teardown is in the video above. But a few things came up that apply to almost every publication I look at, so I wanted to pull them out here for you. 🤩 Substack Tips & Tricks How many Notes per day should you post on Substack?

Recently, I have been reading that Substack is struggling and subscriptions are declining. They talk about subscription fatigue. Now, Iā€™m sitting here having had one of the best months financially since I started my my solopreneur journey 2 years ago. Thanks, July! Not from subscriptions alone, thatā€™s for sure. But through 1:1 coaching requests (which increased by 50%!) Done for your Design Service My new Substack Playbook Offer My new AI skills library And sponsoring of my newsletter.