Every year, my dad and I go on a father son trip somewhere for the weekend. We go wherever he wants to go. This year we are going to Chicago – I’m heading out in about an hour. In the past, we’ve gone to Las Vegas, Los Angeles, San Francisco, San Diego, Austin, Miami Beach, Las Vegas again, and a few other places.
I think Chicago will be perfect for us. Our goal is just to hang out. This afternoon we are doing the Chicago Architecture Foundation River Cruise, having a drink with my long time friend Jeff Hyman (my very first VC investment was in his company Career Central, which ended up changing it’s name to Cruel World, which was fitting for its ultimate demise), and then dinner at Swift & Sons.
Tomorrow morning I’m going for a long run, we are going to the Cubs game, getting a tour of Wrigley Field, and then having dinner at Coco Pazzo with Troy Henikoff (who runs Techstars Chicago) and his wife Kristin. We are heading home Sunday morning.
There will be a lot of chocolate ice cream. It’s our favorite food and we will have it at least twice each day.
Maybe we’ll have it three times on Saturday if they sell it at Wrigley Field.
My only regret about my father son trip with my dad is that we’ve only been doing it for a decade. I wish we had started 40 years ago. If you are a father and your son is at least ten years old, I strongly encourage you to consider this tradition. If you are a son and you are at least 20 years old, I encourage you to take the initiative and just start doing this with your dad.
I’m not a big city guy, so one of my favorite things to do when I find myself in a big city is get up early, before the city wakes up, and go for a run. There’s something about the silence echoing throughout a vast developed physical space such as LA that calms me down and builds up some reserves for me for the day.
I was in LA all day yesterday – starting with a Fireside Chat organized by David C Murphy. It was a full room of entrepreneurs and what I hope was a stimulating and useful conversation for them. I got in an Uber and traveled across town to Nix Hydra, a company run by two remarkable young women that we recently invested in. I got in another Uber and returned to Santa Monica where I attended the Innovators Collective Dinner, hung out with some old friends, and met a few new ones. Today I’m at the Disney Accelerator and tomorrow I’m at Oblong.
At dinner, I sat with my long time friend Matt McCall. Matt and I were on the FeedBurner board together and he’s got a powerful connection between LA and Chicago – another city with an incredibly thriving startup community. Matt’s part of Pritzker Group Venture Capital which has offices in Chicago and LA as a result of where JB Pritzker and Tony Pritzker call home (Chicago and LA respectively). While they invest nationally, they have deep roots in both cities and are key players in the respective startup communities, along with the cities at large.
As I was talking to Matt, it rolled around in my head that there are a lot of similarities in the growth of both the Chicago and LA startup communities. Our engagement with each is similar – we have Techstars programs in each (Techstars Chicago and Disney Accelerator), we’ve made investments in each over the years, and they are each cities that I have personal affinity for and have spent a lot of time in, even though I’m not a big city kid.
I came back to an email in my inbox from Troy Henikoff, the Managing Director of Techstars Chicago, which closed the loop on this thought for me. Troy has been a key part of the development of the Chicago startup community and we’ve been good friends from the moment he first reached out to me about developing an accelerator in Chicago.
Troy reminded me about the Chicago Venture Summit, which is coming up on 10/14 and 10/15. The lineup looks incredible and includes keynotes from folks like Travis Kalanick (Uber), Padmasree Warrior (Cisco Chief Technology & Strategy Officer), Ted Leonsis (Revolution Partners and previous AOL CEO), and Peter Thiel. Not surprising, JB Pritzker is one of the leaders of the event. In the note that Troy sent me, there are confirmed attendees from VC firms such as Founders Fund, DFJ, NEA, GE Ventures, Motorola Ventures, Accel, Revolution, First Round Capital and Andreessen Horowitz. Yes, it’s a serious event worth attending if you can.
Since I started thinking about Startup Communities in 2010, a few years before I wrote the book Startup Communities: Building an Entrepreneurial Ecosystem in Your City, I believed the discussion about entrepreneurship would spread far and wide. If we could have the amazing things going on in Boulder that we were experiencing at the time, there was no reason every major city in the world couldn’t have a vibrant startup community. It’s a joy to see this developing fast, and in a powerful and sustainable way, in cities like Chicago and LA. Sure, there’s always been significant entrepreneurial activities in both cities, but the essence of the startup community in both places feels different – and more powerful – this time around.