Living the Messy Middle Each Day

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I’ve made a career out of helping people who reside in the Messy Middle, that 10 to 12 year span between the launch of a business and an eventual positive or negative exit. It’s an interesting space to be in for someone who likes to be in the weeds, but for everyone else, it seems pretty boring and mundane. For the most part, I’ve been on the outside looking in – helping build things as a contractor or peeking in as an advisor. I’ve started startups in the past. However, nothing could prepare me for the adventure that is the building of EntrePartners.

We officially celebrated one year of the Innovation Center back at the beginning of September. Most of the membership that joined in the first year is still around – I have no idea what the churn rate should be for my program, but I feel like we’re doing okay. People are actually starting to find us through our Web site and through the grapevine rather than by first meeting me. In September, I nearly doubled the membership of the Innovation Center – three new full-time Innovation Center members and two Coworking + Accountability members joining on Saturday mornings. Events are starting to fill up, and word is spreading throughout the region that we exist.

Building something like EntrePartners really shows you who is in your corner and who just pretends to be there. For the most part, people landed where I thought they would land. I’ve been a bit disappointed by the handful of people who ended up in the latter group but not surprised. The great part about this process of separating the wheat from the chaff is finding out there wasn’t much chaff – I’ve built such a great network over the past decade that the few obstacles in my path are easily avoidable. Doors have opened for me during this journey that wouldn’t have opened if not for the positive work I’ve put into building our local entrepreneurial ecosystem.

Over the past few months, I’ve embarked on the “We Exist” tour across the state, getting meetings with everyone from local economic development agencies to state government, area nonprofits and small business. In several cases, folks may not have known we exist but have heard of the work I’ve done – they’re either subscribed to We Are All EntrePartners, knew about my turnaround of the Undergraduate Incubator, or had the chance to work with me previously (or some combination of the three.) My message in this blog of reaching out to people all across the region and learning from what they are building has helped build the network needed to make this grand experiment work.

When I named the organization EntrePartners, I didn’t know how important the “partners” part of the name would be. As a one-man operation, I rely heavily on my partners to fill in the gaps and spread the word about what we’re doing. I’m incredibly appreciative to everyone who has been willing to spread our flyers across the area, repost our social media messages without thinking twice, and show up to our events no matter what time of day they occur. It’s hard work launching events, courses, and services, but I can see the good in what’s being done. I want the restore the energy we had around startups in downtown Iowa City pre-pandemic, even if the well-funded entities aren’t interested. Those who have partnered with us remember how it was and want the same outcome.

The trick now is to turn that level of organizational support that we’ve built and turn it into financial support. I would love to turn EntrePartners into more than just a one-man operation but can’t do that without the funding to pay people. I’m running a capital campaign at the moment called $50K for EntrePartners in order to raise the funds to upgrade equipment and pay people for their time. I can’t be in the office constantly, so it would be nice to be able to hire a community manager to be there when I’m not. We also need some new IT equipment – a paper printer and a 3D printer are the two most requested items on the wish list, and it would also be nice to replace the 20-year-old computer powering the Podcast Studio. As of this writing, I’ve raised about 10 percent of our goal, with letters and emails going on this weekend.

Beyond the capital campaign, I’m also tossing around the idea of an “angel club” as a way to help fund our operations. This idea hit me after one of our new members came to me specifically to help his company raise institutional money. There are plenty of folks in the area who qualify as accredited investors but just don’t realize it, and there are others who know they qualify but don’t have access to deal flow. EntrePartners could function as a mediator for deal flow, as more startups come to us seeking help with fundraising.

We don’t really focus on startups looking to raise money, but people are coming to us because the big players in the ecosystem won’t give these startup founders the time of day. The stories I’m hearing from people coming to EntrePartners for help are disappointing but not surprising knowing with whom they are interacting. Giving someone an audience only costs a few minutes of time and absolutely zero dollars, and you never know what dividends might come from that investment of a few minutes. But, I guess if you want to continue being rude to people even as you struggle to find funding after your main benefactor passed away, that’s your call.

As I’ve stated since the beginning, EntrePartners is here to serve folks that other organizations don’t want to serve. As long as a founder if willing to be coached and as long as they aren’t wedded to a particular solution, any startup is viable. Most of the people we serve just need some moral support and connections to others in the community – neither of these things cost any money and don’t require any kind of special facilities. Basic entrepreneurship doesn’t require expensive offices – in fact, it thrives in places that others have forgotten. Even if I were swimming in funding, I’d still keep the folding tables, second-hand chairs, and complete lack of walls between myself and the people I serve. You can’t build a community if you hide in a private office all the time.

Building EntrePartners has kept me rather tethered to home – one of the reasons I’m raising money is to bring on someone who can be here while I return to travel, both regionally and across the country. The only travel I’ve managed to do over the past few months has been tied to my role as Vice President of the Main Street West Branch board, going to the Iowa Downtown Conference in Muscatine back in August and the Main Street Iowa Fall Training in Waterloo just a few weeks ago. These were both great opportunities to meet other economic developers and people working to improve the statewide business community, and I’m glad I had the chance to attend each of those events. I made a number of connections across the state, and I’m looking forward to bringing EntrePartners programming to their communities.

There’s not much external activity on the horizon for the rest of 2025 – the InnoVenture Challenge event won’t be taking place in December like the last couple of years but will return some time in the first half of 2026. Internally, we’re coming up quickly on Follow-Up Weekend, November 14-16 at the EntrePartners Innovation Center. Global Entrepreneurship Week is also coming up the week of November 17, with several events planned during that week. I’m opening the doors to the Innovation Center that entire week for Open Coworking, and our Open House on the afternoon and evening of the 21st should be a lot of fun. After Global Entrepreneurship Week, the holiday season begins, and the entrepreneurial event calendar comes to a close for the year.

I’m starting to work on my traditional two-part post for December 31. While I haven’t traveled all that much – I’ve actually not traveled by plane all year for the first time since 2021 – there’s going to be a lot to cover. I’ve done quite a lot at EntrePartners and through the Main Street West Branch board this year while slowly continuing to work on Cider Finder. Grinding away on businesses is not nearly as externally exciting as traveling and attending entrepreneurial events, but looking back on the progress made is just as fun. Beyond a couple of book reviews, I won’t be posting here again until then.

I hope you’re going to join us either at Follow-Up Weekend or at one or more of EntrePartners’ events during Global Entrepreneurship Week. If you haven’t visited the EntrePartners Innovation Center yet, I’d love to give you a tour. It’s a lot of fun to show off what we’re working on in Iowa City’s best-kept secret.