It’s taken me a few months to finish this blog post. I’ve started and stopped working on it a bunch of times between the middle of May and today. Every time I’d sit down to work on this, another fire would need to be extinguished somewhere. Over the past few months, I’ve figured out what my professional and personal capacities really are – capacities in energy, time, and willingness to move forward. I’ve discovered what truly matters and what can be offloaded onto others. The past few months have truly lit a fire under me that hadn’t existed up until now.
I talk a lot about the Messy Middle in entrepreneurship – that period between the launch of a product or service and the eventual endpoint, be it a successful exit a decade or so later or closing down a business after a couple of years of struggle. I’d say my journey at EntrePartners is fully within the Messy Middle after two full years of plugging away at every aspect of the organization. From the variety of services I offer, to the types of seminars and courses I run, to the very events that started the organization, there is a lot to build and maintain.
As the Messy Middle goes, there are better days and there are tougher days. There are times where I’m incredibly optimistic about the future of EntrePartners, and there are others where I’m just about ready to throw in the towel. I appreciate everything that our supporters do for us and the doors that they’ve opened over the last couple of years. At the same time, I’m incredibly disappointed in some portions of our local entrepreneurial ecosystem and the large organizations and governmental entities that support them.
It’s been a while since I’ve provided an update – the longest I’ve ever gone on this platform in between updates. It’s not because there hasn’t been anything to discuss, like it was during the pandemic. On the contrary! So much has happened between May and now. There have been a bunch of events across the state and the country that I’ve attended, and I’ve finally learned how to ask potential donors for money. I’ve discovered that I have less patience for those who are unwilling to help themselves and that it’s not worth trying to coach the uncoachable. I’ve also come to realize that the ability to speak my mind is worth every benefit and penalty that it brings.
Prior to my last post at the end of May, I left my new position with 1 Million Cups that I started in March. After six weeks on the job, I still did not have access to half the things I was to manage, the amount of handholding I was going to have to do with some of the team was going to drive me bonkers over time, and the amount of travel and extra responsibilities that were being added to my calendar put me well beyond the “part-time” nature of the position. I’ve seen former colleagues “donate” extra time to other organizations that easily could pay them for that time, and that’s not something I tolerate in my professional life. The number of hours on the contract is a maximum, not a suggestion. I wish the rest of the team the best of luck in fixing what leadership there has been “retooling” for over two years. I don’t expect any changes or improvements in 1MC unless there’s a full leadership change, but it’s thankfully not my problem anymore. Expect the “retooling” to continue for the foreseeable future.
So, after the high school reunion at the end of May, it was full steam ahead in the world of entrepreneurial ecosystem building. EntreFest this past June was an interesting combination of hugs and punches to the face. Even though EntrePartners was the only entrepreneurial service organization in Iowa City not included at headquarters, I had a chance to show off our space to a number of friends and fans who had made the trip to Iowa City for the conference. I made some good connections with a lot of folks who had never heard of us, and I have some new partnerships currently brewing from those three days. There is a lot of pent-up demand for the types of events and services I already run across the state and the region, and EntrePartners will strive to fill those gaps, as we’ve quietly done in eastern Iowa these past two years.
I can’t exactly say why we were the only organization not included in the tabling area at EntreFest headquarters. Perhaps it’s because we don’t pay to play – a scourge that kills even the most functional entrepreneurial ecosystems. The low startup cost and low overhead of the EntrePartners Innovation Center makes the millions Johnson County and Iowa City have poured (and continue to pour) into certain organizations with middling results look incredibly fiscally irresponsible in a time of tightening budgets. Our ability to go above and around much larger and better-funded organizations and deliver higher-quality results doesn’t sit well with those who want to own the space. The festivities are going back to Cedar Rapids next June, which I fully expected. I’ve applied to speak at next year’s conference, and I highly doubt I’ll be chosen. If I’m chosen, I’ll attend. If I’m frozen out by the usual suspects, then there’s really no reason for me to make the trip. Now that there’s a larger, more friendlier alternative in Iowa Startup Week, there’s not much reason for me to attend EntreFest.
So, after three days of alternating handshakes and insults from “community partners,” I decided to review what EntrePartners is doing and how we can better position ourselves going forward. I ended up postponing Startup Weekend Iowa City this year until November 20-22, in order for the event to coincide with Follow-Up Weekend. Even though our messaging is pretty clear for Startup Weekend, there are always questions about whether or not someone can work on their existing idea during the weekend. Combining the two events will prevent those issues and will get more people into the Innovation Center. The more people we can get in the door, the further word will spread that we exist.
I also took feedback about Iowa City Open Coffee and decided to relaunch it with speakers each week. The whole purpose of the event was not to have an agenda, but that really didn’t catch on with a lot of people. We’ve had a lot of folks show up once and then never again, for whatever reason. Since relaunching in August, we’ve had a different speaker each week talk about whatever their pet project is – either it’s something that they are building and want feedback, or it’s an organization that wants to get the word out about the work they are doing in the community, or it’s someone with a particular skill who wants to give a presentation on that skill. We’re not terribly picky about presenters right now. The idea is that the more people we get in the door, the more hearts and minds we unlock with the work we’re doing.
I’ve also been doing a lot of outreach to national organizations as well as local organizations that need low-cost space, in order to bring more programming to the EntrePartners Innovation Center. I’ve reached out to several groups that run business incubator-style programming about bringing that programming here, as I’m solidifying membership in the Innovation Center as being part of an incubator program rather than a loose confederation of people who just want a spot to work occasionally in downtown Iowa City. I’ve shed a few members over the last couple of months who really weren’t committed to making their ideas real, but I’ve also brought on a few folks who seem much more willing to keep moving forward, no matter the obstacles.
One of the partnerships that I hope really pans out in the coming months is with Iowa City Robotics. They were looking for a location to run their FIRST LEGO League program, as their current space is too small and full of parts for the robots their students are building. The EntrePartners Innovation Center has exactly what they need – a bunch of tables, space to move around, and somewhere they can store the projects in progress. I’ve wanted to move into K-12 events and activities, but I haven’t had the bandwidth to work on it. As part of the partnership, I’m working with the students on communication and pitching skills, and gave a talk to the group back in September. Some of them are brand new to pitching in front of judging panels, and like most kids that age, it makes them a bit nervous. I saw improvement in the hour that the group was in the Innovation Center! We’re going to be working on future get-togethers and trainings for students in the future.
I’ve also launched a volunteer program for EntrePartners, since I’m not able to be in the office all the time. For 60 hours of volunteering at different events and in the Innovation Center, volunteers can gain access to a center membership for a year – a $600 value on paper and significantly more valuable in reality for an early-stage startup. I’m limiting this to three people to start, with the idea that one of the three will be interested in working in the space during normal business hours and serve as my proxy when I’m not able to be in the office, due to travel or family commitments. I’ve even developed a frequently asked questions and answers sheet for a potential community manager, as people do show up to the space randomly with questions about our services and programming. Most of my current membership uses the space on evenings and weekends, and I don’t expect any of the paying members to serve as community manager.
I sincerely appreciate those who take part in our events and give their support, either though monetary donations or the time they spend mentoring or spreading the word about the things EntrePartners does. I always teach about the power of networks to benefit the products and services people are building. The people who choose to work with us because they understand the gaps in the ecosystem and the unwillingness of others to fix those gaps are the best people out there. My spirits have been lifted over the past few weeks as both local businesses and individuals have begun to come out of the woodwork and pledge support, either financially or though their time. Some of the support has come completely out of the blue, but most has been due to my travels over the last few weeks.
At the end of September and beginning of October, I spent a week in Des Moines at the inaugural Iowa Startup Week event. I presented on the morning of the final day of the event, running through the basics of taking an idea and turning it into an actual business in 60 minutes. I enjoyed the keynotes and the other talks during the week, and I really enjoyed the social events. As I’ve discussed ad nauseam in this blog, social events are the glue that holds the best events together. Startup weeks tend to have the best social events – not all plain old networking, but there’s always an aspect of that at any business gathering. Conferences and conventions that skimp on the social events tend to be the ones I stop attending over time. Pandemic-era virtual conferences were notorious for a lack of social gatherings, which is why so many people were so eager to get back to in-person events so quickly.
I actually ran out of cards by Tuesday evening’s event. I brought 50 EntrePartners cards with me from Iowa City, and this was the first time I’d ever run out during a startup week. Most of the people attending were new to me, and there was a distinct lack of the usual loudmouths and self-promoters that show up and are lauded at every event in eastern Iowa. The event itself wasn’t a tool for promoting the underlying organization running it – a refreshing change from my experience in June. It was designed to be a vessel for making the statewide ecosystem a more functional place by bringing together and lifting up those who are actually making a difference in our ecosystem, not just friends of the organizers.
Multiple times during the week, I heard variations on the phrase “we wish you were in Des Moines instead of Iowa City” from several different people. The thought of moving my entire organization to central Iowa has crossed my mind many times over the last few years as I’ve been fighting for any sort of recognition in eastern Iowa. The Iowa City Downtown District and Iowa City government can’t seem to be bothered to even feign interest in what we’re building. Greater Iowa City doesn’t really work with us because I’m not willing to pay the chamber of commerce tax. The university decided to open an incubator space a block away from me this fall, potentially in violation of state law regarding direct competition with private entities. NewBoCo has decided to duplicate a good chunk of what I’m doing across the state rather than working together and ceding any publicity. The fiefdoms are still not happy with a new entrant in the space that points out gaps in service and between words and action. So much for rising tides lifting all ships around here.
This is why I’m now in the business of convincing folks one by one that what we’re doing at EntrePartners is the way forward, and why I’m having more success working with folks in central Iowa and beyond the borders of the state. Folks who don’t have a stake in eastern Iowa fiefdoms and siloed programs tend to understand the importance of filling gaps and supporting entrepreneurs from start to finish rather than making sure a certain organization’s name winds up on the 10 o’clock news or in a local business journal consumed nearly exclusively by bankers and real estate agents. Our dwindling local media is more concerned with preserving relationships than actually delivering information, so we’re moving beyond them to podcasts and articles where it counts. I’ve already recorded one podcast interview, with several others on the way. Building an alternate network of influence is the future, and perhaps legacy information sources will eventually catch up.
I spent a few days out in San Francisco and Silicon Valley a couple of weeks ago as part of Gener8tor’s Innovators on a Plane program. I want to integrate what we’re doing at EntrePartners more closely with the Gener8tor system, as there is a fair amount of overlap between some of their initial programming and the things I do for entrepreneurs at the EntrePartners Innovation Center. Having looked at both the Techstars and Gener8tor networks and what each of their pre-accelerator community programs involve, the Gener8tor programs are a much better fit for what we’re doing in eastern Iowa. So, I attended in order to get to know the folks in that network a bit better.
We had a chance to visit with city government and the local chamber of commerce in San Francisco, take tours of Google and John Deere facilities in Silicon Valley, and talk AI with founders in the Bay Area. It was hilarious listening to the representative from city government dance around the reasons why San Francisco had so much trouble retaining talent and companies around and in the wake of the pandemic when we all know the wounds were self-inflicted. We also visited Third Coast Ventures’ office in San Francisco for a working lunch on the first full day and got to network and mingle at an upscale wine bar one evening and a Michelin Bib Gourmand restaurant another evening. On the academic side, we visited a couple of incubator programs at UC Berkeley, one of which is essentially a giant version of what I ran at the BELL, located in what used to be an art museum on campus. Seeing programs and facilities like this as compared to the lack of support I was given during my two years at the university, I really wonder what could have been accomplished.
I made a bunch of great connections during my three days in San Francisco. There was one other Iowan on the trip, and she and I have already met and started planning our work together in the future, along with folks from two other Midwestern university systems. I’ve offered up my space and programs as part of a larger public-private consortium that’s in the works, and I’m really excited to see where this partnership goes. Combine the successful connections from San Francisco with the great week spent in Des Moines, and the past month has been a vast turnaround from the frustration of the few months beforehand.
So, what now? I’m feeling a new energy grow as coalitions are building and support is growing. I have entrepreneurs and changemakers popping into the Innovation Center from all over the state, some of whom I’ve never met before. The word seems to be spreading about what we’re building, and I’m actually feeling a positive energy around Startup Weekend Iowa City that I haven’t felt in a few years. Gathering the best and the brightest from around the region is now the goal rather than relying on our own backyard.
We’re facing a leadership reckoning locally. The Iowa City school district is tens of millions of dollars in the hole due to years of poor leadership with no easy fix in sight. As the same time, the county supervisors tried and failed for a third time to pass a bond issue to build a palace of an administration building with a jail attached. The university is beginning to see the enrollment cliff and has vastly overplayed their hand in the community they try their best to ignore. Budget cuts are laying bare the absolute entitlement some local leaders in both government and local social service nonprofits have for your tax money. As long as local power structures continue to be dominated by the least capable among us, there will be no change and nothing will be fixed. That’s why the goal now is to build something amazing and resilient that does not rely on local tastemakers. I’m building a life raft as the Titanic sinks.
My message to all of you is to build something resilient and portable, because if you’re anything like me, help will be nonexistent to start. Build a ring of support and supporters to start and move from there. As the emcee at 1MC Iowa City for several years, I asked hundreds of folks “what can we, as the community, do to help you?” Outside of my core ring of supporters, I’ve never been asked this question. Meanwhile, the chosen few in this community get chance after chance, one assist after another, with plenty of trophies awarded along the way. Holding this unfortunately realistic viewpoint doesn’t compromise my ability to work with others locally – those folks aren’t willing to work with us regardless, and I’m tired of waiting on the sideline for any shred of acceptance from these people.
It’s taken over two years of grinding away to get as far as I have, and it finally feels like I’m starting to turn the corner. These next two months are going to be critical as I continue to build the nest egg for my organization, finish several different projects that will pay off in 2027, and continue to offer entrepreneurs and creatives a place that actually wants them to succeed. We’re building the future of technology and community without interference. We’re going to break through the local unwillingness to take risks on the future. It’s the only way to compete in our current world. The status quo is broken and non-competitive with our neighbors, and it’s up to us to determine the future.
If you’re willing to join me and actually make a difference, you know where I am.

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