🍦How I'd start over

Allow me to reintroduce myself.

I'm here to help you build a local media company that changes your life. It can be a…

Each week, this newsletter will have one big idea. Today's is…

This isn't hypothetical. I launched a new one two months ago.

First, can your area support a newsletter? Consider:

Naptown Scoop covers 315 square miles with 140,000 people. There are 5 towns that matter; Annapolis is the center geographically and culturally.

You need 150,000 people in a reasonable radius to achieve full-time income. Any less and you're in side hustle territory.

Reasonable radius is subjective. In Annapolis, it's 10 miles. In a rural area, it might be 25.

I like broad local newsletters. Yes, the niches are in the riches. But here, being local is your niche. Unless you're in a major US city (1 million plus people), don't niche down to dog owners or fitness buffs.

Broad local newsletters cover:

I don't cover crime and I never get political.

I also like aggregating. Find 50–100 publications, social media pages, FB groups, and events calendars and curate the best stuff for your newsletter.

For tech, keep it simple. You need a place to send emails, a place to write them, a place to stay organized, and a website (kinda).

Sending emails (ESP): beehiiv, Kit, Substack, Mailchimp or similar. There are tons of tools for this. I use beehiiv because it's easy, built for newsletter-first publishing, and it's priced right.

Writing emails: Don't write in your ESP. Trust me. Write somewhere with collaborative editing. I love Notion.

Stay organized: Again, I use Notion. It's a powerful and customizable all-in-one workspace app. Alternatives include Coda, ClickUp, Tana, and Slite.

I say kinda for the website because you don't need one to start. All that matters is collecting emails and ESPs have forms for that. That said, beehiiv has a powerful website builder on all paid plans.

Before we go any further, would you mind taking a quick survey to let me know who’s reading this? It will help me tailor each week’s big idea to the real needs of readers just like you.

I publish five days a week. I started with one, quickly jumped to two, and 3 years later increased to five. All increases served to sell more sponsorships.

Five days a week is a grind even with my great systems. I recommend starting with one or two. For once a week, publish on Wednesday. For twice, Tuesday and Thursday.

At the end of the day, listen to your readers in three ways.

Getting the first 1,000 subscribers is easy if you're willing to spend money on Facebook ads. Target by ZIP code and target women over 35.

Facebook ads are the single most reliable way to get readers. Sure, tell everyone you know. But with Facebook ads, you can tell everyone in town. You should get readers for less than $1 each, ideally less than $0.75.

You don't have to wait to make money. My first sponsorship happened in the first two weeks. Best $50 I've ever made. I know people who sell sponsorships before sending a single newsletter.

That said, I like to focus on growth early. The ads I do sell come from inbound requests. I always mention that sponsorships are available, but I'm not cold calling asking businesses if they want to advertise to 500 people. I don’t like that look.

When folks do reach out, get creative. Have them sponsor the welcome email or offer them 6 ads to use any time in the next three months.

Don't overthink it. Your first newsletter will suck. But you have to publish one to publish 500. I laugh at my old newsletters. But they taught me everything I know.

Alright. Now get back to work.