2018: The Year of New Beginnings

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Want to compare where I am now versus where I was one year ago? Check out 2017’s Year in Review.

It’s always fun to sit down and start writing down all of the things done during a year. These retrospective posts at the end of each year are always my favorite to create – to celebrate a year of successes and to reflect on how to improve for the following year. Looking over the items I’ve written down, I’ve covered a great deal of ground in 2018. Trips to Denver, Kansas City, and several to Des Moines were some of the major highlights this year. In the second part of this post, I will discuss plans for 2019, which includes trips to several new locations throughout the United States. For now, let’s reflect on the year that was.

I did a lot of mentoring this year – more than I realized before I sat down and wrote out everything. Between college students, the Mandela Fellows from sub-Saharan Africa, and even a few junior high-aged kids, I spent a great deal of time working with folks who are trying to turn their ideas into viable businesses. I participated in the Iowa Startup Games both in the spring and the fall – I’ve mentored so many times now that I could go an entire week wearing nothing but Iowa Startup Games t-shirts. I really love hearing the idea that the student teams develop over the weekends, and it’s a way that I can feed my Startup Weekend addiction without walking away with a new project. A win-win, really. The time I spent with the junior high kids was talking more about marketing, which was a nice departure from talking straight business model development, as I had the year prior.

In the spring and summer, I spent a great deal of time traveling to and from Des Moines – three different trips over the course of March and April, and another trip back in July. The trips involved two happy hours, two trips to 1 Million Cups in Des Moines, a conference with CEOs and venture capitalists, and another conference with young entrepreneurs from all over the world. If you look back at my “looking ahead at 2018” post, only one of these trips was planned ahead of time. I wouldn’t be surprised if the same thing happens in 2019 – but will Des Moines be the location?

Looking over the four trips in and back this year, two of them involved attending the Freelancer Happy Hour at Gravitate’s location in West Des Moines. The first one I attended was the first one ever, and there was a decent turnout of freelancers from across Des Moines, plus myself and Mr. Google Hat himself from Cedar Rapids. The timing of the event was great, because James and I were planning to attend 1MC in Des Moines the following morning, to see what Governor Reynolds had to say about entrepreneurship in Iowa. The governor’s presentation ended up being more tightly controlled than what we were expecting, without the usual Q&A from the audience, which was disappointing. However, it was still nice to connect with the entrepreneurial community in Des Moines again.

Just after returning to eastern Iowa, I was pinged on Slack by the CEO of Dwolla, letting me know about a new get-together they were putting together called Monetery, with limited free access for entrepreneurial movers and shakers from across the region. I jumped at the chance to get a ticket, and I was very pleased with the result. I was able to rub shoulders with some of the biggest names in the entrepreneurial community in the Midwest and beyond, and the speakers they chose were outstanding – the lineup even included Brad Feld, the ultimate entrepreneurial ecosystem builder!

Just a couple of weeks later, I returned to downtown Des Moines for the Young Entrepreneur Convention, back for its third iteration. I was pleased with how seriously the organizing committee took suggestions from past attendees, including myself. I thought that this year’s event was a great improvement over the past years – the event was a lot less of a “bro-fest” than the past two years, with much of the social media influencer nonsense cut out or moved into its own track. I stuck to the tech and entrepreneurial track, and I thought the speakers did well. Both Monetery and the Young Entrepreneur Convention are on my list for 2019, and I’ll talk more about what I hope to get out of each event in part 2 of this post.

My final trip to Des Moines in July was also unplanned – Ben McDougal asked me to come over to 1MC and present Cider Finder, as well as talk about Startup Weekend Iowa City, as that event was coming up the following weekend. I wasn’t planning to start presenting Cider Finder this early, but I’d already been asked to pinch hit once, at 1MC Iowa City. I noticed that the Freelance Happy Hour also was to take place the evening before, so I agreed to come in and make the rounds one more time. The happy hour wasn’t as well attended this time around, but the few of us who were there talked and enjoyed beverages until late into the evening – honestly, a much better experience than it would have been with a larger crowd. 1MC also went very well, and I walked away with some great new ideas for Cider Finder, some of which I’m working into the first version of the app.

This was also the year of the Great Entrepreneurial Divorce of 2018, with Cedar Rapids and Iowa City splitting into two 1 Million Cups chapters. As many of you know, Cedar Rapids and Iowa City had shared one chapter for many years, as one of the first 1MC chapters established beyond Kansas City. Our ecosystem, together was “the corridor,” was originally strong enough to sustain one chapter and one coworking space each in both Iowa City and in Cedar Rapids. Over the last five years, much had grown and much had changed in the entrepreneurial landscape – much of which I’ve documented in this blog. Cedar Rapids now has four competing coworking spaces, and Iowa City has an amazing space in MERGE and a future innovation center planned for the old Art Building on the U of I campus. Much of the original entrepreneurial effort had clustered itself in Cedar Rapids in the last couple of years, with those of us in Iowa City feeling as though we were playing second banana. Honestly, the split was bound to happen sooner rather than later.

So, in May, we fired up 1MC Iowa City for the first time as its own chapter, with a reformatted Iowa City Open Coffee before the event each week. It was definitely a struggle at first, with many people confused about the schedule change (and some people still are confused about it), and the Cedar Rapids chapter hanging onto all of the years-old, well-established social media accounts. The old franchise stayed up north, and we were the expansion team. It was up to us to either flounder along, like most expansion teams do at the beginning, or try for major success right from the start. Our organizing team has put in a ton of effort, made some minor tweaks to the format, and have managed to schedule some amazing presenters from throughout Iowa and the Midwest. We’re managing to bring in 30-40 people just about every week, including about 15-20 for Open Coffee. Some weeks, we’re well over 50 people crammed into “Iowa City’s Living Room.” Not too shabby for a scrappy little expansion team!

Local entrepreneurial success also extended to the relaunched Startup Weekend Iowa City this past July, with nearly 25 people participating on five different teams, most of which were led by either high school or college students. Most of our participants were from eastern Iowa, but people came from as far away as Des Moines and Mason City to take part in the event. I had spent months reaching out to coworking spaces and entrepreneurs across the entire state, and spread the word on just about every free channel I could find. We ended up raising enough money from sponsors to keep ticket prices low, and we wound up doing just better than breaking even for the weekend. Not bad for the only Startup Weekend in the state this year! The organizing team and I have big plans for 2019, and I’ll talk more about those in part two of this post.

One event that moved out of Iowa City this past spring was EntreFEST, which took place in Cedar Rapids back in May. The move wasn’t related to the Great Entrepreneurial Divorce and due mainly to the still-ongoing remodeling of the Ped Mall in Iowa City. However, there was definitely the feeling in the air during the event that the splitting the market in two played into the move; that it was Cedar Rapids’ chance to shine. Unfortunately, Cedar Rapids – specifically the NewBo neighborhood – really isn’t set up to handle events like EntreFEST the way that the Ped Mall in Iowa City is. Several major streets run through the area, and with the redevelopment of the neighborhood occurring mostly in the last five years, there is minimal shade in public outdoor areas. So, pick your poison – nearly get run over by a car moving between sessions or fry in the sun during an outdoor keynote that starts nearly half an hour late.

I’ve been suggesting for a while now that the EntreFEST organizers (and really anyone else planning a large scale entrepreneurial event in this part of the country) attend part or all of Denver Startup Week or another event like it. While I don’t suggest that they try to completely replicate Denver Startup Week locally (we saw how well replicating SXSW went for Go Cedar Rapids), there are things about the event in Colorado that could be copied to improve our event in eastern Iowa. The pub crawl at the end of the first full day of EntreFEST was a step in the right direction, highlighting some of the local establishments in downtown Cedar Rapids. However, there was this strange lack of cohesiveness when traveling between venues that I ended up leaving early – not to mention the party at the Backpocket brewpub turned into this weird in-group bro-fest nightmare, at which point I left. Also, other than the awesome keynote by Scott Belsky, much of the break-out session content seemed either recycled from years previous or featured the same dozen or so presenters. It’s not terribly conducive to return attendees.

I plead with you, local entrepreneurial event organizers! Attend conferences and startup weeks outside the area. Bring the best of the best back with you, and create something amazing here! Do something that is greater than yourself or your organization. Our local entrepreneurial ecosystem is counting on it.

Denver Startup Week was amazing once again this year. It was set up much the same as in 2017, but some of the locations of the events changed. The weather was also much nicer this year than last year, with sunshine nearly the entire time as opposed to the nearly constant cold rain of 2017. I was able to attend the entire week of activities, and I was able to snag tickets to all of the headline events, including the Kickoff Breakfast and the Daymond John sit-down interview. Honestly, doing the entire week, even scheduling myself with more breaks each day, was a bit overwhelming. In 2017, I was only about to do about three and a half out of the five days, and that seemed just about right. I think Monday through Thursday of the week is the sweet spot, and might be what I schedule for 2019. Part 2 of this post will have more discussion of this.

Roughly a month later, I was back on the road, heading to Kansas City for the 1 Million Cups Organizers’ Summit. I’d driven through Kansas City in the past, but I’d never actually visited the city. I left both impressed with Kansas City itself and what the Kauffman Foundation is doing for entrepreneurs throughout the United States. This summit was really the icing on top of the cake with regards to the theme for this year: don’t feel like you’re alone in your entrepreneurial journey, because there are others with the same struggles, same battles, and same worries. As I put at the end of my Freelance Media Newsletter each month, we’re all in this together.

Nearly all of the events I attended this year reinforced this feeling of togetherness, from Scott Belsky’s talk on the “messy middle,” to the Denver Startup Week session on being a parent and a creative, to the message conveyed during the 1MC Organizers’ Summit. Nobody should feel as through they are building a company in a bubble. There are people out there willing to listen and to help, and it’s just a matter of finding those connections as an entrepreneur or facilitating those connections as a community builder. This is why it’s vital that we have community programs for entrepreneurs like 1 Million Cups, Startup Weekend, meetings like the Freelancer Meetup and Open Coffee, and public pitch competitions. Entrepreneurs and creatives need to be able to bounce ideas off each other in spaces where people keep an open mind. 2019 should be a banner year for this type of community building, and I’ll share my plans for facilitating this in part 2.

These were the biggest events and revelations of the year. Of course, there were some other things with which I help or other events I attended – I’m still struggling with saying no to things. If you want more detail from the past year, feel free to read back over the last twelve months of posts. So, what’s next for 2019? Continue onto the next post!