Aren’t we the best species in the history of the planet at building community? Idk, I probably got a C in that class too. But I think we’re pretty good at it, and I’m certain that we lost a step in our togetherness groove over the last four years. So, my “startup community” has been on the mind.
How did I lose my grip on it in the first place?
Well, around 2017, at the conclusion of what some call “a startup CEO’s worst nightmare” (aka “down round”) that led to a new beginning, I put my head down and lost touch with my cherished local startup community. I figured I’d climb back to where our first company needed to be on traction, get to the exit, and then return to the community for my second go-round.
Did that. Came back. And thought to myself: “wait, …where the hell is everybody?”
We got older. Went remote. Felt the comfy-ness of our pajamas. Researched the Netflix catalog. This that and the other thing adding warm layers to the shell of our comfort zones.
Time to snap out of it. Time to rebuild the community.
I want “in” ! Maybe you do too?
If so, hit me up, I’ve seen some things that you should know about. Three of them happening in Chicago include…
- An AI engineer cultivating a tight knit cohort of seasoned founders going back to 1871.
- A former “Future Founders” kid gathering an under-the-radar rapidly growing dinner club.
- Two well known investors forgoing the big annual party for a series of small intimate discussions.
Let me show you what I mean…
1. Eric’s Density: “…because working on your startup alone sucks”
In partnership with 1871 / Betsy Ziegler, my friend Eric Mills formed a program called Density.Ventures that I eagerly joined. We’re a tight knit founder group that comes to our shared office 4 days a week mainly because, as Eric put it to me in his invite, “working on your startup alone sucks.”
I knew he was right about that, so despite the hassle of getting 2 kids to daycare and catching a train from the suburbs to the city, I haul over to the Merchandise Mart daily. It’s the best thing I’ve done for myself & our company.
Here’s what I get out of being on the Density team:
- Momentum – “Daniel & Adam (NinetyNine) closed another deal?!” I holler & high five, then buckle down, because now I’m due to go get a bucket.
- Shared exec team / braintrust – we’re each attuned to the other’s business/goals by way of our bi-weekly “founders forum” + daily lunch chats, dissecting each other’s product & GTM problems together. We want each other to win, and we get what we give.
- Discipline – the last thing I want to be is the one chump who rolls into founders-forum without a tight grip on how we tracked against the targets Danny & I communicated to the group last time.
2. Sunny’s Dinner Club: experimental home cooked meal gone right.
He started it in his studio apartment, cooking homemade Indian food for strangers. Sunny Shah didn’t have some flashy founder or VC resume, didn’t have a CRM of entrepreneurs. He just wanted to gather a community. So he hosted a dinner. Then another.
Today, Sunny’s Chicago Dinner Club has a food sponsor that covers the dinner, a VC providing the space, and most important of all, a threaded community of founders – some known, many unknown – gathering for family-style dinner.
I wonder… What might this evolve into next? What ideas & teams might connect? And to think, it all started with an experiment conducted by a young person who got bored and decided to do something uncomfortable.
On that note – while Sunny didn’t yet run a company when he started his dinner club, now he does. SunnyCreators launched last week!
3. Bailey & Eddie: investors going small, and Canh’s growing tribe
And lastly, I’ve seen two separate investors in town – Bailey Moore & Eddie Lou – organizing carefully curated small group gatherings. Something about these felt different. They were more about intimate connections, vulnerability, and sharing failures, rather than volume of attendees & one-up showcasing.
Most recently, my longtime friend & investor Bailey Moore decided to forego doing a big annual party for Wintrust Ventures, and rather allocated that budget to a series of small dinners, one of which I got to be a part of. At dinner, I got to know Canh Tran, CEO/co-founder of RippleShot.
I could instantly tell that Canh was a masterful story-teller, and his thought-provoking questions are a big part of why we were the last table to leave the restaurant that night, but what struck me the most was Canh’s talk of “tribe”. By all means Canh has done it all in his career, and yet he listened to everyone with a fascination for them, ideated a range of ideas and repeatedly talked about expanding his “tribe.”
I left dinner wanting to be more like Canh, and hungry for more stories.
So tell me – who else is doing what when? I want “in”. Entrepreneurship is a jungle, and thus I’ll leave you with the final line of one of my favorite poems, portraying the law that binds us all:
“…this law runneth forward and back. For the strength of the pack is the wolf, and the strength of the wolf is the pack.”
PS – just as I finish writing this, I see the following post from my old pal Karl Hughes. Hell yes, Karl.
