Welp, it’s been a few weeks.
If you know me in real life or follow me on social, you know I decided to jump back into the sports newsletter game and that’s been taking up a lot of my time. I launched Bears By 7 just a day before the NFL Draft and if you haven’t checked it out, you should.
It’s been great so far. I’m nearing 500 subscribers after just two weeks and I think it’s a solid product. People seem to enjoy getting it in their inbox by 7 (yep) and I’m excited to see what it can be.
But why did I start it now?
Well, it’s been a little over three months since I was laid off and it was important for me to start building something as I go through the different stages of finding what’s next.
After four years of being consumed with building CHGO and ALLCITY, the sudden stop was difficult to deal with. Scrolling LinkedIn all day isn’t good for anyone’s mental health and I always feel better when I’m writing or planning something.
Plus, I’ve never really been one to sit around and wait for something to happen.
Bears By 7 has also given me some of my identity back as well as a project to be proud of. Getting a call from WGN to be on their Saturday night sports show just a few days after making the newsletter public was really nourishing to my mental space. (I don’t know if Nate, Josh or Andy know how much that meant, but they should.)
I’d had the idea for Bears By 7 for awhile now, but kept futzing around with the approach and waiting for the “perfect” time or an even better concept. When I realized the NFL Draft was coming up, I knew it was time to pull the ripcord and just fly. Otherwise, I’d likely have to wait until late July to have the best
Beehiiv makes it ridiculously easy to launch a newsletter/website these days and I went from nothing to something that looked really good in about the span of three days using the platform.
I used Claude for inspiration on design and color ideas (not a strength of mine). It also gave me feedback on my conversion copy for landing pages and runs a workflow that gathers that day’s Bears news and important story links for me to consider when I sit down to write each afternoon or night.
And then, like that, Bears By 7 was out in the open.
I started off this newsletter by saying “always have a newsletter.” A few months later, I think I should add “always be building” to that advice.
It’s good to be back in the game.
Want to try out Beehiiv on your own? Use my referral link to get a free 14-day trial and 20 percent off your first three months.
Things I’m Currently Enjoying 🥇
The Geosports App game (like everyone else).
The 2025 Chicago Bears Complete Offensive Manual by Bobby Peters. (It’s a surreal feeling to be rooting for a Bears team with someone who actually knows what they’re doing on offense.)
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