Why I Built Free Resources for Chicago Founders

Last month, I interviewed Brad Feld at our Drive Capital Chicago office for the release of his new book Give First. 

For those who don’t know, Brad co-founded Techstars, wrote the book Venture Deals, and helped build the startup ecosystem in Boulder, Colorado from the ground up.

His new book talks about how strong startup communities are built, and we dug into one of his core themes: help without keeping score. Brad told me that “startup communities thrive on mentorship freely given, not just capital or connections.” That line has echoed in my head ever since.

It got me thinking about how much time founders spend just trying to find the basics. In a city like Chicago, the resources exist, but they aren't always easy to track down.

After years of coffees, pitches, and “got a minute?” DMs, I kept seeing the same questions pop up: who funds pre-seed rounds in Chicago? Which coworking spot has 24-hour access? Where do I find a grant instead of another SAFE note?

So one weekend, I opened a fresh Notion doc and started listing every Chicago-specific resource I could think of. That document became bullishonchicago.com, which is a free, living guide for anyone trying to build something in this city.

It includes every VC, accelerator, and angel group I could find, all tagged by check size and sector focus. There’s a section for workspaces, with notes on pricing, perks, and neighborhoods. I added communities like Slack groups and pitch nights, especially for founders from underrepresented backgrounds. 

I even built out a growing list of grants and tax credits.

And I rounded it out with an event calendar so you know which meetups are worth leaving your laptop for. Anyone can submit updates, and I’ll try to update it as frequently as possible.

The site works because the community helps keep it alive.

I also write a weekly email: Landon’s Loop.

Every Monday, it summarizes the most important Chicago tech news, highlights top events and office hours for the week ahead, and ends with one short take on why it all matters.

It only takes five minutes to read, and tens of thousands of founders, operators, and investors use it to stay plugged in. Every week, I hear from readers who forwarded it to someone who should’ve been in the room.

To me, this is what it looks like to build an ecosystem from the ground up. Policy helps. Capital helps. But real progress happens in day-to-day work when founders share what they’ve learned, lend a hand, and make things easier for the next person in line. 

By making information free and visible, we shrink the distance between those two people.

If you want to help, it’s simple: 

- Skim my site and let me know if I missed anything.

- Subscribe to my newsletter and hit reply with a tidbit worth shouting about.

- Offer one hour of feedback to someone a step behind you.

- Give first and Chicago’s flywheel will keep turning.

That’s the story Brad told me.