Inside Chicago Southsider: How We Reached 100 New Subscribers Organically in 5 Days
How one weekend of focus, consistency, and experimentation led to our biggest growth breakthrough.
Hey family,
If you’re new here, welcome. This is our exclusive series for paid subscribers, and I’m so glad to have you on this journey with us.
Inside Chicago Southsider is a behind-the-scenes look at how we’re growing this platform and navigating one of the most fragile and uncertain times in the news industry. Disruption, layoffs, and volatility have become the norm.
Think of this series as our version of a shareholder update. However, Inside Chicago Southsider is more transparent, more personal, and shared in real time.
Right now, the news ecosystem is incredibly fragmented. Layoffs continue at major outlets, and AI is rapidly changing how information is created and consumed. Journalism is feeling the pressure, and we’re not immune.
Many people don’t understand how journalists actually get paid or how local news stays alive — and that lack of awareness creates a dangerous gap. In future editions, I’ll break down the economics behind what we do so you can better understand the systems we’re working within and the challenges we face.
For now, let’s talk about growth, grit, and why I’m stepping out of my comfort zone to make sure Chicago Southsider doesn’t get left behind.
Between May 31 and June 4, we gained 100 new newsletter subscribers — organically.
No paid ads. No fancy tools. Just a light bulb moment.