Today I’m trading Love Park for Buckingham Fountain. The mint for the merc. Independence Hall for the Water Tower. The Eagles for the Bears. The Schuylkill for Lake Michigan. Cheesesteaks for deep dish.
Yes, I’m moving with my family back from Philadelphia, to Chicago.
What brought me to Philadelphia in 2013 was a good and worthwhile cause: joining the acquirer of ProOnGo Expense for the journey of integrating strategic assets into a bigger, stronger, better funded cloud offering, and sticking around to do my part in helping it flourish into something important and relevant to an exponentially larger number of small businesses around the world. The ride was fulfilling. I was surrounded by great customers, colleagues, and investors at work, and the friendliest of neighbors on the homefront.
But yet, something pulled me back to Chicago, despite the logistical hurdles of moving a family the better part of 1,000 miles in time for the school year. What’s so special about Chicago, to make it worth the complication? Many things, but here let me focus on the macro factors that make Chicago a special place for entrepreneurs, and why it will continue to be for the long haul.
- Serial entrepreneurs giving back: It would be hard to imagine a month where you don’t find the founders of GrubHub, Groupon, Braintree, CleverSafe, and countless other luminaries talking about their experiences and counseling founders embarking on their own journeys. Those entrepreneurs benefitting from star-studded advisory boards will in turn pass along the favor to the following generation. The gift of advice and encouragement, sans obligation, is one of the most remarkable characteristics of Chicago’s entrepreneurial environment.
- Ecosystem infrastructure: 1871, TechNexus, the Chicago Innovation Exchange, and a dozen others are providing both the physical venue and more importantly the connective environment that brings together a diverse group of contributors who have a shared motivation to build the next great thing. I believe it to be a critical mass of ecosystem infrastructure that has unstoppable momentum. Gone forever are the days of a four-person startup trying to navigate the details of a triple-net lease, or wondering what central location they might linger at in hopes of catching a few brief words with a prospective board member, investor, or team member.
- Investors with risk/reward preferences that tolerate, no seek, early-stage investment: in 2008 when I began raising capital for ProOnGo, it was hard to find angel investors that had familiarity with the norms of early-stage investing, and that hurdle made the startup process all the more challenging. I was blessed to find a group of tremendous businesspeople that were willing to take a risk on me, and I’m forever grateful for that. They truly were visionary in their willingness to bet on early-stage Chicago ventures (mine being just one in their broader portfolios) and to encourage others to join them for the wild ride of such investments. In comparison to the challenges of raising capital in those days, now there is a feel of fluidity to the conversations about capitalizing startups in Chicago. There is a comfortable belief that a great idea with a great team can find the resources they need to advance through their milestones towards great outcomes.
So farewell Philadelphia, and see you in Chicago. And if your growing company yearns for a more efficient and effective interviewing process, please meet me over at RIVS where we’ll make quick work of advancing your interviewing process into the digital age.
