Chicago-Style Hustle: The Story Behind Lynn’s Chicago Pizza

In this episode of The Pizza King Podcast, I sit down with Lynn from Lynn’s Chicago Pizza to hear her incredible journey from a simple at-home pizza night to running a thriving pizzeria on Chicago’s South Side.

Lynn shares how she and her partner, Chef Brandon, accidentally stumbled into the pizza business after making a deep-dish pizza from scratch at home. What started as a fun experiment quickly turned into something bigger as friends and family raved about their pizzas. Before they knew it, they were selling personal-sized deep-dish pies at a local bar, taking bulk orders, and making a name for themselves.

We talk about how they went from running pop-ups to securing a lease for their first brick-and-mortar location—competing against another concept in a pop-up challenge and winning over their community with great food and a full-on experience (DJ included!). Lynn also opens up about the challenges of funding their startup, the reality of small business finances, and how they had to get creative to make it all work.

One of the biggest takeaways from our conversation is the power of marketing and community engagement. Lynn and Chef Brandon have used Instagram, social media influencers, and local events to build a loyal following. They’ve turned their restaurant into more than just a pizza shop—it’s a community hub with live music, open mic nights, wine dinners, and more.

If you’ve ever thought about starting your own pizzeria, this episode is packed with real-life lessons on taking risks, building a brand, and betting on yourself. Lynn’s story is proof that sometimes the best businesses happen unexpectedly—you just have to be ready to run with it.

📍 Want to check out Lynn’s Chicago Pizza? Follow them on Instagram or Google them to find their location.

🎧 Listen in, get inspired, and if you're in Chicago, go try that Dorchester deep-dish—trust me, it sounds like a must!