There comes a point in one’s life where one realizes that they’ve had just about enough. You wake up one morning and realize that you need to put your foot down and stop playing along with people who don’t actually like you. It’s a gradual process, and then it hits all at once. I’ve come to this realization in the past couple of months – oddly enough, because my high school class is having its 25-year reunion this May.
Realizing that I’ve just acquired a terminal case of old, it hit me gradually and then all of a sudden that there are a lot of things I really don’t have to do or to go along with, and there are a lot of people I don’t have to humor anymore. This isn’t burnout – I’ve suffered from burnout in the past and that feels different. Burnout, at least in my case, involves a complete shutdown of all productivity and more of a depressive state. This feels more like a revelation or an awakening. Only a handful of people are truly on your side, interested in what you’re doing or building. The rest can be removed from your life.
I attribute this revelation to the way a good chunk of my cohort has acted over the past 25 years, coming under the microscope in the class Facebook page. Most of the people exclaiming “I want to know what you’re up to!” unfriended me at some point over the past 20 years, for one bit of wrongthink or another. I am under no obligation to share what I’ve been doing with people who had access to that information and canceled that access because we disagreed on some insignificant topic. Also, knowing how one-dimensional most of my former classmates were 25 years ago, we’re probably going to run out of things to discuss even if I contributed to the conversation.
As former classmates post pictures from high school, I realize that I’m not in any of them. I didn’t socialize much, but then again, I wasn’t really invited to anything social outside of hanging out with a couple of friends with whom I’ve lost touch and a couple others with whom I still occasionally talk. I became much more social in college, becoming better friends with some of my high school classmates who attended The University of Iowa along with me. The last time that this hit me was when my wife and I were planning our wedding in 2009 – I invited only a couple of people from my high school, as most of my friendships dated from August 2001 and beyond.
Am I going to attend the reunion? Of course! It’s much more fun (and probably less abrasive) to interact with people in person than it is on the Internet. There are some people planning to attend who I actually want to see and with whom I wouldn’t mind catching up. A handful of us got together over Zoom during the height of the pandemic, but we really haven’t talked much since 2022. Including them, there are probably 20-30 people who I actually want to see, but a few others may have changed their ways and could surprise me. The rest of them will probably be as obnoxious as they were in the late 1990s.
This class reunion isn’t the only thing that has popped up on my calendar over the past month or two. It looks like I’m finally going to be heading back out on the road more this year than I did last year. Most of the travel is EntrePartners or entrepreneurship support-related, but some of it is cider related as well. I ended up staying close to home a lot in 2025 because I underestimated how hands-on building an organization from nothing would be. It’s still pretty hands-on at the moment, but I’ve gradually been able to create systems for most things that come up over the course of a week, and there are very few drop-ins each month. Most of the time, there’s someone else in the office who can answer questions, and I’ve created handouts for just about anything that comes up. I’m usually at my desk three or four days a week, so the one or two days per week that I’m gone doesn’t matter all that much.
I didn’t get the chance to attend CiderCon this year out in Providence, Rhode Island. I was really bummed about that, since I’ve never been to Rhode Island and wanted to check it off my “visited all fifty states” list. I did have a very good reason for not attending though – I had to drive to Kansas City for an interview with the Kauffman Foundation for a position with 1 Million Cups. I made the final round, which involved creating a 20-minute presentation on the program and how I would perform the job. The presentation was part of a 2-hour interview with the top program staff at the foundation. I drove the nearly five hours there, did the interview, had some Whataburger, and drove back home all in the same day – it’s wild to start out before the sun rises and not finish the day before the sun sets.
I applied for one of the positions being filled back in December, nearly a month prior to writing my year-end summary post. Honestly, I didn’t think anything would come of it, as most applications I complete seem to go into the circular file. However, I was moved to the online group interview round in January and then invited there for an in-person interview in February. I didn’t want to say anything about it to anyone, because I’m stupidly superstitious. I didn’t start telling anyone about the process until a couple of days before the in-person interview because I needed someone to drive me to the rental car place the day before the trip.
Once I made the final round, I was a bit of a nervous wreck. I didn’t sleep well for a couple of days prior to the trip, and I was running on adrenaline the entire drive southwest and during the 2-hour interview. Once I stopped for a burger and fries, I felt my sympathetic nervous system finally disengage. Even after drinking a gallon of coffee and a gallon of Dr. Pepper with my burger and fries, I didn’t need to use the restroom until I was 10 miles or so from Iowa City. I may have sped a bit those last few miles to get to a restroom.
While I was in the last part of the interview talking with one of the program leaders, another open position was mentioned – the Organizer Relations Representative. I can’t remember if I saw this job description when I applied for the other position. I said that I’d be happy to take a look at the job description and apply for that as well, if they thought I might be a good fit for it. I sent in a separate application for that with a slide deck and report answering some questions they posed. I guess they liked what I submitted, because I was offered the Organizer Relations Representative position!
Throughout this experience, I’ve had to dust off some knowledge from decades ago – I haven’t spent this much time in Excel in years, and I haven’t taken statistics since 2005. When I was routinely putting together charts and graphs for presentations in high school, college, and graduate school, Excel and PowerPoint had far fewer features than they do today (let along all of the AI stuff interspersed into the software.) I’ve also started learning some new platforms both for this new position and for what I do at EntrePartners and Cider Finder. I signed up for the free online version of Tableau and have been watching some videos to learn about it. For EntrePartners, I’ve been diving into the Notion ecosystem. Cider Finder has taken me into the AWS ecosystem, and for both EntrePartners and Cider Finder, I’ve been going down the generative and agentic AI rabbit holes. Between all of the new (to me) software, all of the updates on older software I mastered as a kid and a young adult, I’m starting to feel my age.
So, with this new position comes more travel. I’ll be heading down to Kansas City for the better part of a week at the end of April for the official group onboarding at the foundation along with the others who filled these new positions. I also had to head down there most of the week of March 16, as my position must be completely up and running prior to the week in April with the rest of the group. A good chunk of what I will do in this role is administrative, both for our communities across the country and for the organizers, but there is a bit of public facing work as well. Also, we open our applications for new communities at the beginning of May, so that process had to be elucidated this past week so we can get everything properly prepared prior to the end of April. I’ll be traveling to Kansas City about every four weeks or so for these first few months, and I’ll also be visiting some of the 1MC communities around the Midwest starting in May.
I’m also going to be involved with the big summit at the end of July – I attended last year’s summit thinking it was going to be my last one. I was holding out for one last big event down there after so many years of online programming during and after the pandemic. I had attended the 1MC Organizer’s Summit in 2018 and 2019, and 2020 was supposed to be my third and last, as I was planning to retire as an organizer had the pandemic not happened. I stopped attending the online events after about a year, both regionally and nationally, as it was clear that those events weren’t designed with organizers in mind (or, at least, that’s how they ended up coming off.) The best part of events like that is the ability to chat and network with others in similar positions across the country after the officially programming had concluded, and the online meetings just weren’t designed for that. I was glad that they brought back the in-person version of the summit this past summer, and it’s going to be exciting to be on the organizing side of the program this year.
Another big event on the calendar in a couple of months is the Great Lakes International Cider and Perry Competition in Grand Rapids, Michigan. When I knew I wasn’t going to be able to make it to CiderCon, I immediately put GLINTCAP on my calendar and submitted my steward application right when it opened. I’ve always had a lot of fun at that event each time I’ve attended, and it looks like at least a few of my cider friends are going to be there as either stewards or judges. Plus, the steward room usually turns into a giant party by the end of the day – they were a bit stricter about consuming beverages during judging a couple of years ago when I last volunteered due to a shortage of samples. Hopefully, they’ve resolved this problem, and we can relax a bit behind the curtain.
I always enjoy my trips up to Grand Rapids, especially when some of my friends from CiderCon make the trip as well. The drive up there isn’t usually too bad, as long as the traffic around Chicago is light. When I made the trip a couple of years ago, I somehow lucked out and didn’t hit any stopped traffic between Joliet and Michigan City – usually, there is at least one stretch where traffic is stopped or slowed due to construction or an accident. Sometimes, it takes as long to get through Chicago traffic as it does to get from the Indiana-Michigan line and Grand Rapids!
The ticket page for Startup Weekend Iowa City is already live, taking place June 12-14 this year in order to line up with EntreFest. I’ve decided to not bother asking the folks at Greater Iowa City to donate their space for the event – next year might be different so long as certain staff finally retires. It’s really exhausting waiting out people as they take forever to retire – this seems to be a major problem around here. My entire career is littered with coworkers who didn’t know when to pull the plug and burned out in place. I beg of all of you – if it’s time for me to go, please be honest and tell me.
I was planning to work with EntreFest to host breakout sessions in my Innovation Center space. However, they’ve decided to work with other locations downtown due to “partner considerations.” Reading between the lines, I’m being frozen out by either the university, Greater Iowa City, or NewBoCo. Over the past two years, I’ve tried to make it quite clear that my organization’s mission does not interfere with any of the existing players in the community and have attempted to build relationships across the region, but it’s obvious that the large players have picked their winners, and I’m not among them. Therefore, I’m done being nice and playing along – unapologetic stepping on toes will commence.
So, during EntreFest, we’ll be running complementary programming in the EntrePartners Innovation Center, based on the “experiences” I attended and visited at SXSW a couple of years ago. The EntrePartners Lounge will offer networking opportunities, informal talks, and a chance to try out our podcast studio. The schedule is still being designed, but we’ll be done by noon on the 12th, so we have time to reset the space for Startup Weekend Iowa City. Stay tuned to EntrePartners’ social media channels for more information. We’ll be showcasing everything we do in the space that week, and I can’t wait to share what’s in store!
Between the EntrePartners Lounge and Startup Weekend Iowa City, I’m going to be doing one more pass for corporate and individual sponsors in the coming couple of weeks. I’ll be reaching out to organizations large and small to support what we’re doing – everything from food and drink support for events to ongoing support for the Innovation Center. If a company or a state agency is willing to support EntreFest, they should be willing to support a much more cost-conscious event like the ones in the Innovation Center that same week. No one organization owns entrepreneurship in the state of Iowa, and firmly reminding some people and organizations of this is top priority. This will be the week of never-ending emails and messages, but I’m looking forward to it.
Startup pitch competition season is well underway across the country, and I’m starting to receive requests to judge competitions again this year. I specialize in first-round judging where I get a stack of applications and grade on a rubric – it’s not difficult, and it’s a lot of fun reading through the applications. There are always a couple of applications in group I get that seem like obvious winners, and almost always, they end up in the final round. If you’re subscribed to my Unfireable newsletter, you could end up in some amazing pitch competitions!
There are still a lot of moving pieces and projects I’m working on right now that I can’t yet announce. I’m hoping to write again in May with more good news, prior to Startup Weekend Iowa City. I’ve found that I have the most success when I throw things at the wall, not caring if they stick or not. I still need to get over being so nervous and overly analytical when things actually start going well. With as much good work as I’ve put in over the years, I deserve to have some things go well We’ll see if karma continues to pay me back this year – so far, so good.