I’m Sure This Proven Bad Idea Will Totally Work This Time

Reading Time: 12 minutes

Each time I sit down to write one of these blog posts, I am under the delusion that I can finish the thing in one sitting. I have my list of topics to cover – events I’ve attended or run in the past month or two, developments in my many different projects, creative projects that I’ve finally wrapped up, and what’s coming up on the horizon. I’m trying to break myself of the thought that there will ever again be a time where I can sit down, interruption-free, and hammer out something from beginning to end. That line of thinking is a pipe dream when one juggles as much as I am right now.

Spring rushed headlong into summer over the past month or so. The kids are finished with the academic year, and they’ve had their dance recital. June felt like such a long time away when I last wrote a blog post, but with the last couple of years of corona-related time distortions, I forgot how time seems to compress during the month of May. This year was more compressed than any other in the past few, between the long drive to Traverse City, Michigan, and back for Startup Weekend, and then diving right into coaching at the Hawkeye Student Accelerator. Add to that all of the other plates I’m spinning, and the momentum has continued right into the first couple of weeks of this month.

As I mentioned in my last post, my last Startup Weekend trip for the spring took me nine hours to the north and east, to northern Michigan for Startup Weekend Traverse City. I had never been that far north in Michigan, having only ever been around the Grand Rapids area. I took a bit longer going up than I did coming back, as I had roughly two days to get to my destination. I stopped at the halfway point on Thursday to enjoy a bit of cider at Peat’s Cider Social, a bowling alley located just off of Interstate 94 before Interstate 196 branches off to the north. I had a nice chat with the staff and got to see some of the bowling machinery in the back of the building. Before I left, I had a growler filled with their orange zest cider, which I brought back to Iowa at the end of the trip.

I spent Friday driving along the shore of Lake Michigan, passing through a number of towns and a lot of countryside. I was expecting a decent amount of forest, but I was surprised how hilly it was for a good amount of the distance north of Grand Rapids. I followed Highway 31 right into Traverse City to my hotel, got checked in and took a shower, and then drove over to Northwestern Michigan College, where the event was to be held. The Startup Weekend event was the finale to the Startup Week that the organizers had been running all week, with the demo day held at the City Opera House. One of the things that I love about traveling to different places to facilitate Startup Weekends is getting to see new and interesting venues where the community comes together to make great things, and this was no exception.

This was the smallest Startup Weekend that I’ve facilitated – only 9 participants distributed among three teams. However, this was the first group where every single person participating got up and pitched some sort of idea on Friday evening. I had gotten close to 100 percent participation at one event in San Antonio – I think we were two or three people short of full participation there. I really like to facilitate smaller events because I get to know the participants better. The event in Columbia at the end of February, with around 100 participants, was so large that I really only got to know 15-20 people over the course of the weekend. The size of the event doesn’t matter when it comes to the quality of the ideas turned into startups during the weekend – it completely depends on the people involved.

I had a great time working with the participants, getting to chat with all of them over the course of the weekend. Dinner on Saturday evening was a cookout in front of the college’s library – the weather was absolutely perfect, the burgers were great, and it was a nice way to connect with everyone at the midpoint of the event. After the demo day, most of the group stuck around for an after party at the bar on the first floor of the City Opera House. Before I went back to the hotel for the night, I made a stop at the Taproot Cider House, just to see what they had on tap and grab some dinner. They had a number of Michigan ciders available, so I got a flight of a few ciders that I hadn’t had before. I’m glad that I was still able to make the trip to Traverse City, even though I didn’t get to stay in Michigan the following week to judge at GLINTCAP, instead driving the entire nine hours home on Monday morning and afternoon. On the way back, I took Highway 131 instead of following the lake, as nearly the entire return route was divided highway and interstate.

After getting a good night’s sleep, it was time to head to campus to meet the students participating in the undergraduate Hawkeye Student Accelerator. There are 11 companies going through the program this summer, ten of which have solo founders. I was assigned to five of the students, to help guide them through the basics of startups and hopefully to a point this summer where they are actively selling something by August. One of my mentees already has a product for sale both online and in brick and mortar stores and is working on product number two during the accelerator. Another has some technology developed, but hasn’t started selling it just yet. The others are still much closer to the idea stage, and I want to get them to the startup stage with minimum viable products by August. Four of the five startups involve physical products or services surrounding physical products, while the fifth is developing an app/online platform. (Most of the other students that I am not directly mentoring are developing physical products as well – maybe we’re finally over the app for everything hump?)

The graduate cohort of the Hawkeye Student Accelerator meets every Tuesday evening, so I hopped on that Zoom call after I got home from campus and had something to eat. The graduate cohort is huge – something like 25 teams, many of whom are solo founders or teams of two. The curriculum for this group is a bit different than the undergraduate group – it moves significantly faster, and it’s designed for scaling businesses more than moving ideas to the startup stage. I have three mentees from this group – one who is purely in the idea stage, another in the startup stage, and the third who has a product and is trying to figure out how to sell and scale. All three of my graduate mentees are going to present at 1 Million Cups this summer – two of them already have, and seem to have taken away some great information and contacts from the community members who were in attendance.

Speaking of 1 Million Cups, I got a chance to emcee this past week when we had our biggest crowd since returning to in-person events, thanks to EntreFest coming back to Iowa City (more on EntreFest later in the post.) It was such a great feeling seeing the room fill up the way it did, and the students did great jobs presenting their businesses in front of a bunch of people new to our event. There were just as many first-timers as there were people from Cedar Rapids who made the trip since their event was canceled. I hope that a number of those who joined us liked what they saw and decide to join us at future events. I’m also hoping that we continue to have awesome attendance numbers the rest of the summer, as the other students give their presentations through the end of July.

I won’t be emceeing again until the end of August because I finally have the go-ahead to travel to Uganda on July 18 in order to teach entrepreneurship in Arua through the Mandela Washington Fellowship Reciprocal Exchange! About a week and a half after I wrote my previous post, I finally heard from the folks at the Mandela Washington Fellowship that my in-person proposal was approved and I could contact the consulate to set a security briefing and arrange with the fellowship’s vendors to obtain plane tickets and a visa into the country. I was starting to wonder if they wouldn’t approve the in-person version of my project, since they were taking so long to let me know the decision.

This is my first trip outside the United States, so I’m a bit nervous. I’m trying to get everything together well ahead of time, so that I don’t end up forgetting anything here at home, since I’ll be half a world away for a month. It’s not nearly as easy to source things in that part of the world, so there’s a great deal of stuff I have to take along just to teach a class: all of the technology and handouts have to make it over there with me. I’m also making sure I have a month supply of medicine and toiletries, so I’m not having to find a pharmacy when I am most likely going to be on foot. While I have my plane tickets figured out already, I’m relying on my partners to find me a decent hotel room – I’m not looking for anything fancy, but air conditioning would be nice since I’m going to be so close to the Equator.

The curriculum is coming along pretty well. I’m planning eight lectures plus a demo day over the course of three weeks – Monday, Wednesday, and Friday evenings at a local restaurant, and possibly a bigger venue for the demo day where I can record the presentations and put together a polished video to show people back here at home. I don’t trust our Internet streaming capabilities to get the job done, but I’m going to try to stream it live as well. On Tuesdays and Thursdays, I plan to hold office hours for the students to ask questions and get feedback through individual coaching. During some other down time, I’ll get the b-roll and individual interviews for the polished demo day video. It’s going to be a solid four weeks of work on the other side of the world. What an amazing opportunity!

I’ve also started selling tickets for Startup Weekend Iowa City and meeting with the rest of the committee for that project. The Iowa City Area Development Group is completely on board this year helping promote and host the event, along with finding prize sponsors and financial contributors. I’m glad that I have a team to help this year – with the number of things I have going on right now, I don’t know if I’d be able to pull this thing off alone this year. We’re also planning to have a number of teachers and potentially some high school students join us, so they can see what the full version of the weekend is like after participating in the abbreviated Design Dash event a couple of months ago. I have a couple of emails to send out to our Iowa EdTech Collaborative and Jacobson Institute partners, in order to drive up ticket sales.

Speaking of Design Dash, the event was a smashing success! We had about 80 students and a dozen teachers take part in the six-hour blitz, where we provided the ideas, and the student-led teams had to turn those ideas into potential businesses. At the end of the event, students created posters and gave an elevator pitch to a panel of judges. The judges and I went through and picked “winners” of a number of categories – we didn’t name a first, second, and third place like we usually do at Startup Weekend. We wanted all of the teams to walk away with something fun at the end, and focus more on cooperation than competition. I heard nothing but great feedback about the event, and I’ve been told that the Iowa EdTech Collaborative is already planning to hold another installment of the event sometime in late September or early October and another sometime in mid- to late March – far enough into the semester where a field trip to Iowa City would work for the teachers and students, but early enough in the semester so that finals aren’t affected by the timing. I was told that they would like me to facilitate again, both at the fall event and the spring event. I’m incredibly honored that they have so much trust in my abilities to lead this thing that they’ve already renewed me for at least two more events.

EntrePartners was officially approved by The James Gang as one of its newest endeavors! I got the news at the end of April, several weeks after I pitched the idea at the April meeting. Just like the Reciprocal Exchange project, I was starting to get worried due to the delay in news from the board. I got the bank account up and running in May, and now the organization is slowly launching. The first outreach event was two weekends ago at the Diversity Market on the south side of Iowa City. I brought handouts for all of the current events – Iowa City Open Coffee, Startup Weekend Iowa City, and 1 Million Cups. Over the course of the three hours I was there, I talked to about a dozen people, and many of them seemed interested in the cause. I still haven’t had a chance to put together the logo, Web site, and social media accounts for the organization just yet, which might have been nice while I was doing community outreach. I’m glad I had the opportunity to table at that event, since I’m still trying to figure out ways to connect with that community. My support of the Builders + Backers Idea Accelerator program is starting to help, but there are always ways to improve outreach beyond the usual crowd of entrepreneurs who already show up to my events. (Speaking of, the next cohort of Builders should be announced sometime in the next couple of weeks!)

As I mentioned earlier, we had a great crowd last week for 1 Million Cups and Iowa City Open Coffee because EntreFest was finally back in Iowa City after several years. I haven’t attended EntreFest since 2018 due to a number of reasons – GLINTCAP being the main one – and the event hasn’t been in Iowa City since 2017. From the number of comments I received, people were very happy that it was back in Iowa City. Since it was back here at home, I wanted to attend as much of it as I could, so I cleared my schedule and made the time to be there Wednesday evening through Friday afternoon. There were a number of people who were going to be there and I hadn’t seen in person since 2019, and I don’t think that I was the only person with this mindset during the week.

I went to a number of social events, including the kickoff event on Wednesday and the Iowa Startup Accelerator Demo Day program. On Thursday, I went to a couple of sessions where people I knew were presenting, but I spent most of the day catching up with a number of friends over coffee and other beverages. The keynote address by John Henry on Thursday afternoon was probably my favorite session of the entire conference. His story is amazing, and his storytelling ability is top notch. I didn’t get a chance to see the Venture School pitch competition because the room was full and about 30 degrees warmer than the rest of the convention hall, so I stayed out in the reception area and caught up with a number of old and new friends. I did get to see who won the competition before heading to a small get-together with the rest of the JPEC folks, where I had some great conversations. I’m really enjoying being part of this group, and we’ll see what their plans are for me in the fall and beyond.

I only made it to one session on Friday – the future of educational technology. I’m glad I made it to this session, because I was recognized for my work with the Iowa EdTech Collaborative and the Design Dash program. Like I said before, I really had a great time facilitating this program, and I am really looking forward to the next edition of Design Dash this fall. I stuck around and talked to a number of people after the session was over, and then tried to avoid the rain on my way back to MERGE, in order to get a bit of work done. I tried to go the entire conference without dealing with email, but there is so much going on right now, that turned out to be completely impossible.

Due to taking a long lunch, I decided to hang things up early and follow a number of friends over to the wrap-up party location and start wrapping up EntreFest a little before the party officially started. This allowed me to spend a bit more time with some people who I hadn’t seen in person in years, and others with whom I had never spent time in person, having met them during the pandemic through different channels. I also got to spend a bit of time with some of the students during the wrap-up party, and got to find out what they took away from the event. All in all, this was a great event! I would be fine with the prospect of EntreFest not leaving Iowa City again – I know it will at some point, but one can hope.

So, what’s next? Startup Weekend Iowa City is in roughly four weeks, and then I get on a series of planes bound for Uganda, by way of Chicago and Qatar. I have so much work to do before I can get on any of the planes, not just related to the trip, but with everything else in play at the moment. EntrePartners needs a lot of work done, and Cider Finder is still moving at a snail’s pace. I always say that I should have time coming up, but I need to break myself of that delusion right now. It’s going to be a grind for the next four weeks – lots of late nights and early mornings in my immediate future.

I’m hoping to have a chance to write a post before I leave for Uganda, but I don’t know if that will happen. Like I said before, I don’t trust my ability to do much online once I leave the United States, and that includes posting on the blog. Deep down, I’m actually looking forward to being mostly off the grid for a month. I’m going to be experiencing so much during my trip, I’m not going to have time to mess around online, even if I had the kind of connectivity that I have at home. If I don’t get something online while I’m there, expect a lengthy recap right when I get home. I have a series of flights that add up to about 20 hours, so I’ll have a bit of time in the air to get some writing done.

Wish me luck as I attempt the impossible over the next four weeks!