When I sit down to pull together a summary of each year, I begin by writing down all of the different places I’ve been, different events I’ve attended, and any major lessons learned over the course of the year. Since I began this process nearly a decade ago, the list has grown longer each year (with the exception of 2020.) I think about all of the people I’ve met and the lives I’ve touched in the last twelve months. Last year felt like the kickoff to something amazing – a chance to restart. This year felt like the continuation of that momentum combined with the culmination of a lot of hard work done prior to the pandemic.
I’ve planted a lot of trees since 2014, and many of them started to bear fruit this year. We talk about the hockey stick in the world of entrepreneurship, and that’s what happened this year – everything seems to creep along for years, and then all of a sudden everything pays off. In fact, I may have planted too many trees. I didn’t expect everything to mature in such a short period of time – a good problem to have, of course. However, it leads to a year where the number of days I’ve taken off from some form of work can be counted on my fingers.
Last January feels like a lifetime ago. There’s been some sort of weird time distortion this year in the opposite direction of 2020’s time distortion. While that year felt like it dragged on at a snail’s pace, 2022 seemed fragmented into several years’ worth of time crammed into twelve months. In particular, it felt like three years of time containing eight years of progress. The trip to Virginia for CiderCon at the end of January does not feel like it was in the same year as the trip to southern California to facilitate a Startup Weekend in late March, or the same year as the month spent in Uganda. I spent nearly a sixth of the year living out of suitcases, significantly more than I’ve ever done before.
Not only has time distorted due to travel. Reflecting on the year, I’ve created more digital stuff this year than I had in any previous year, even stretching back to my stint at the Institute for Public Health Practice when I was building all of that stuff in Flash. I spent a surprising amount of time in front of a keyboard and mouse creating curricula and content, even with all of the travel. Between Startup Weekends, 1 Million Cups, and the Reciprocal Exchange video series, I created and published over 100 videos and still have several to finish in the first part of 2023. From January to August, I generated a bunch of Google Docs and slide decks, and then had to relearn Microsoft Office when I started at the Undergraduate Startup Incubator. I haven’t had to use Office since 2011, and it’s changed a bit in the last decade. I built a few Web sites along the way as well, with a couple of site refreshes still in the pipeline.
I had the honor of facilitating Startup Weekends or similar events each month for a six-month stretch, from December 2021 in San Antonio; through January 2022 on Discord at Startup Weekend Iowa Online; February 2022 at Columbia, Missouri; March 2022 at California State University Channel Islands; April 2022 at the inaugural Design Dash; to May 2022 at Traverse City, Michigan. I took June off before returning to organize and facilitate Startup Weekend Iowa City in July, Demo Day in Uganda in August, and the second Design Dash in October. Half of these events wouldn’t have happened if not for my guidance, persistence, and love of the startup ecosystem here in eastern Iowa.
Neither of the Design Dash events would have happened without me. I led the team through the process of very heavily modifying the three-day Startup Weekend model to fit into a 6-hour event for high school students. I’d already modified it down to 26 hours in the case of Startup Weekend Iowa Online, and had to simplify things further with 20 fewer hours available. The fall Design Dash wouldn’t have happened had I not suggested the committee begin to meet a month before the event. Even if you’ve run an event in the past, there are a number of logistical things that need to be done prior to the next event – you can’t just show up the day of the event and expect things to work exactly the same. I guess I do such a great job pulling the levers behind the scenes that nobody even notices anything is happening.
I do know that there are people who notice. I wouldn’t have had the chance to spend a month in Africa if I hadn’t made connections years ago. I wouldn’t have been tasked with leading the Undergraduate Startup Accelerator through its comeback from corona if I hadn’t shown that I know my way around entrepreneurial ecosystem building. I wouldn’t be called on to facilitate events time and again if I weren’t doing something right.
I don’t win awards or trophies, but I certainly get results. Over 500 people started or accelerated their entrepreneurial journeys in the past year through events I facilitated and classes I taught. On multiple occasions, people have said that programs I’ve run inspired them to start or restart a business or startup. It’s a huge impact on an individual level, and it’s all part of leaving this place in better shape than I found it. That should be the goal of each and every person building something, somewhere, and in a perfect world, the rewards would be equal to the effort input. Unfortunately, that’s not the case.
As I’ve always said, there’s an inverse relationship between attention paid to someone and the actual amount that someone is contributing to the community or society at large. It’s much easier to hype the flavor of the week rather than encourage someone through the messy middle. The messy middle doesn’t generate flashy results, but it’s at the core of everything that’s every been built. One of the core tenets that I’m building into the Undergraduate Startup Incubator is some sort of reward system for hard work in the messy middle. First-time entrepreneurs can easily become former entrepreneurs without reassurance and guidance, and college students especially so. This seems like hardcore hand-holding, but it could make a huge difference ten or twenty years down the line.
It’s about playing the long game – you plant the trees now, but they don’t bear fruit for years.
One of the awesome outcomes of this year was the separation of my entrepreneurial ecosystem building events from my program and project facilitation and content creation activities through the formation of EntrePartners. I finally built a separate home for a number of community activities and I’ve finally focused the freelancing side down from the always nebulous “media producer” to something that makes more sense to people outside of the content creation space. EntrePartners has branding, and the freelancing side will be rebranded in the coming months away from small, one-off projects, to building larger, more sustainable visions for the future. I want my freelance work to focus more on facilitating dreams coming true and making ideas real rather than just being some guy who creates videos and Web sites, and for events like Iowa City Open Coffee and Startup Weekend Iowa City to function as fully community-driven events rather than just “events run by Jay.”
The Undergraduate Startup Incubator is in a much better place now than it was this summer during the Accelerator program. Taking on the leadership of that program involved the sharpest learning curve I’d ever encountered in my professional life, and I know I’m still not off the curve. All of my students received some form of an A this past semester, and I’d probably give myself a B- as the shepherd of this herd of sharks. There were a number of moments of panic during the semester, and for several weeks, I was doing nothing but meeting with students and working on program recruitment. It seems to have paid off – I’ve already doubled the size of the class from fall to spring semester based on the class list. The key for this coming semester will be to cement a number of systems in place that were nonexistent when I started in August, and attempt to streamline or automate other things, so I spend less time sending emails and repeating tasks.
One of my duties at the Undergraduate Startup Incubator is to continue working on 1 Million Cups, something I was hoping to retire from this year. Working with the national organization has become an absolute chore. I participated in something called a Collaborative Learning Circle during the first part of the year, and it absolutely put me off ever helping the organization again. It was the most disorganized mess of a program led by people who didn’t seem to know what they were doing. There was no guidance, and our solutions that we proposed could never be implemented due to the stubbornness of the folks at the headquarters in Kansas City. By the end of the program, I was just showing up so I’d get paid at the end.
After the Collaborative Learning Circle debacle, they decided to replace the scheduling Web site with something from Salesforce, probably costing the organization tens of thousands of dollars for something that completely upended the workflow of scheduling, includes a bunch of features nobody asked for, and is missing half of the features of the old system that were actually helpful. The launch was an unmitigated disaster, and nothing has been fixed in the four months in which we’ve been dealing with this. I haven’t been sending any of our potential presenters to that Web site – I’ve been scheduling them in a Google Sheet shared with the rest of the Iowa City organizing team. (Thankfully, we were duplicating info in this sheet before the new Web site was launched, so we didn’t lose data like other communities.)
I’ll only attend 1MC Organizer Summit again if it’s in person down in Kansas City. They insisted on a third online 1MCOS in 2022, and I didn’t attend. From what I’ve heard about it, I’m glad I skipped it. I wonder if the attendance was just as sparse as 2021, when there were only about 40 people attending, with even fewer communities represented. The entire point of going to 1MCOS is to connect with other community organizers – something the folks at Kauffman either don’t seem to understand or don’t want to happen. I also skipped the holiday party this month – again, you go to a holiday party to talk with your peers, not to sit and listen to the “important people” give a lecture. I’m really starting to think that 1MC has run its course and it’s time to consider moving on from the program. We’ll see how much support we receive in 2023 from the national organization – I’m not holding out much hope.
EntreFest finally returned to Iowa City this past June, and I was part of the organizing committee. Beyond picking some of the speakers, we really didn’t do all that much. We didn’t have anything to do with planning the social events and didn’t do much to work through the session scheduling. The actual event was a lot of fun, and it was great to see the Accelerator students get out there and talk with other attendees. I had challenged them to find someone who fit into every category of entrepreneurial ecosystem actor from Brad Feld’s book The Startup Community Way. A couple of the students were actually successful in finding everyone! I saw a few people who I hadn’t seen for a while, but a number of the regulars from past events weren’t there. Let’s hope that those folks make an appearance next year.
Over 12 months, I covered tens of thousands of miles by air and road, shook thousands of hands, ate food that I’ve never eaten before, learned about cultures I’d never heard of before this year, shot days worth of video, wrote hundreds of thousands of words, read a couple dozen books, partied at a gas station, had three different currencies in my wallet at one time, and watched the sun set behind the Rockies while sipping a cider. 2022 was a year I’ll never forget, and 2023 should be even more interesting. Continue on to part 2 to see what I have planned for the next 12 months.