Keep thinking about this. I’ve shouted from rooftops for yrs… but chicago will not change rep with data, published reports, or PR. A 14sec vid just got more 👀 than yrs of “branding” work. As long as founders believe it’s much easier to raise elsewhere, they’ll go elsewhere.

Chicago is literally a cleaner New York and I’m in love. It’s 8 AM and there’s so many people wandering the streets, this city feels alive 😍

I'm glad my "manifesto" of sorts has continued the discussion on Chicago tech community. I have exactly zero desire to run for any public office ever. However, if @EzraMoGee appointed me to run the show with Day 0 being this Monday, here's what my full-court press would be: 1/n

I was not on the CH call the other day & have exactly zero desire to ever be on that dumb app. However, as someone involved in the Chicago tech community for the last decade as a founder, early-stage employee, and author of 2 reports pre-P33, I have some thoughts on things... 1/n

Chicago’s best tech CEO: now montana/michigan It’s 30yo young gun ceos: practically all in Miami It’s most prolific capital raiser: relocated to LA But local ecosystem “leaders” all like

I have always admired founders that build in public. So @iambrentsanders and I are opening up @AvocadoAudio with a weekly podcast. We'll take you through the highs & lows of starting a company in the creator economy. Subscribe & share with your friends avocadoaudio.com/post/the-fo…

1/ Great thread that covers, at a high level, the story of @Udemy. The $3mm Series A was done at 6mm pre. I guess you could say it was rough terms but to the earlier point, no one else was willing to invest. We did the round because we believed in @erenbali’s vision but...

There are two Chicago tech communities The one with the talking heads saying the same things for a decade. And the one with the kids building weird stuff and working their hearts out. Press cares about the former because it’s easy. Invest into the latter because it’s harder.

Chicago, let's stop 1) looking to management consultants for answers 2) celebrating false milestones 3) trying to build "Chicago" companies. More risk capital & convicted investors. Founders who win, stay & invest here. Wins where many common shareholders get $$. That's it.

A trend I'd love to see is more SF-based tech companies opening up Product & Eng offices in non-coastal cities, such as Columbus, Indianapolis, St. Louis, Boise, Milwaukee, Omaha, Nashville, Louisville etc.