Startup Weekend: Fashion Edition and a Great Thanksgiving

If you’ve been following this blog for any length of time, you’ve probably figured out that I absolutely love the Startup Weekend concept. I love attending Startup Weekends and I really enjoy spending an entire weekend building something from idea into an actual, possibly viable business. Add in working with a brand new team of people and potentially doing something outside your comfort zone, and you have one exhausting yet exhilarating experience!

The weekend before Thanksgiving was my third Startup Weekend experience. Sexy Life was my first and ASAP Venues was my second. What would come of my third Startup Weekend? The theme for this weekend’s event was “fashion, technology, and wearables.” I took this to mean that the idea pitched were to somehow fit into that space, as did most of the people that got up to pitch ideas on Friday. There were a couple of ideas that were pretty far out there in left field, but they were not chosen to move on after the voting round Friday evening. All together, 15 ideas moved on to the voting round and 6 ideas were chosen to move on. Of those 6 ideas, 4 teams were able to come together.

On a whim, I decided to get up and pitch an idea. My fashion sense is nearly non-existent, and I thought that there were others out there with the same problem. I consider myself lucky that I’m able to spend time with and associate myself with people who have a keener sense of style than I have, so that some of their fashion sense could possibly rub off on me. The final line of my idea pitch was “somebody, fix this disaster and dress me, please!” So, Dress Me Please was born! A team easily formed around this idea, and we picked a location in the room and got to work.


This was the first I’ve been the idea guy on a team, and by default the team leader. The first task we had on Friday was to get ideas and strategy down on paper. My first challenge as team leader was to deal with a team member that was being uncooperative to the point of nearly sabotaging or hijacking the project for himself. He claimed that he did not “believe in” the Business Model Canvas, and that “we should just target everyone” with our product, rather than pick a target audience. I feel like I handled the situation well, and he didn’t return for the remainder of the weekend. The other team members were on board for customer discovery and seemed genuinely excited to help with this project.

The second challenge that I faced was the management of people over the course of the weekend. Due to transportation issues, one of the team members was stuck on the Cornell College campus, about 30 miles from Iowa City. She was able to conduct some customer discovery on campus, which did help our project. Another team member showed up late both Saturday and Sunday without explanation, and disappeared several times during the weekend, also without explanation, and only contributed a small handful of customer discovery interviews to the project.

The two team members that actually were there and working the entire time contributed nearly all of the customer discovery and competition research, and helped to build out the slide deck for the final pitch, which was much appreciated. They had actually come all the way from Decatur, IL, to participate in our Startup Weekend, as they are planning a similar event in February back in central Illinois (which I will discuss more later in this post.) At times, it felt a bit like herding cats and it makes me appreciate other teams on which I’ve worked where I wasn’t the project manager or team leader.

The third and biggest challenge for me was formulating the pitch. This was both the first time I had gotten up and pitched an idea on Friday and the first time I’d been chosen to give the final project pitch at the end of the weekend, on Sunday evening. Now I know what the other from teams past had gone through on the Sundays of prior Startup Weekends. It’s tough coming up with the right words and the right messaging to get your idea across to the judges.

I put on a tie!

I put on a tie! It’s a momentous occasion.

It’s also tough to distill that message down to only five minutes. It seemed like we got the idea across to the judges, but I ran short on time describing the functionality of the app itself. If we’d had a bit more time or a couple more team members to help build the project while I practiced the pitch, I think that I would have done better with timing during the pitch. I managed to make it all the way through our pitch, but I spent too much time describing the problem and not nearly enough time discussing our solution toward the end of the pitch.

We ended up coming in third behind two teams who had very strong ideas and great pitches. The team that came in first place actually had a functional MVP that involved sending a text and receiving advice by text message – not something we could have done in a weekend, but it worked great with their idea. I consider third place a success for my first time pitching an idea and running a team. Plus, we received some free software licenses from Moqups,, and Sketch – very cool stuff! I’ll have to talk with the two team members who actually helped the entire weekend and see what they would like to have, and I’ll take what’s left. I hope they take the Sketch license, since I don’t have a Mac new enough to benefit from that license… no Linux version, unfortunately, and they both had relatively new MacBooks.

All in all, it was a great experience, and I’m looking forward to the next Startup Weekend. I have a couple of months off, but the next Startup Weekend I have on my calendar is Startup Weekend Decatur, which is scheduled for February 10-12, 2017. If we can scare up a dozen people to go all the way to the Black Hills in South Dakota, we should be able to get a few people together in mid-February to make a much shorter trip to Decatur and show our support for their efforts. Startup Weekend Cedar Rapids is coming up March 3-5, and the next themed Startup Weekend Iowa City is planned for mid-April, with the theme being Games and e-Sports. I know I can round up a bunch of people to either help or participate with that theme – the majority of Team Sexy Life would participate!

It’s hard to believe that I’m already filling next year’s calendar. Add to the above events EntreFEST in May and Denver Startup Week during the final week of September, and I’m going to have to start saying “no” to things much sooner in 2017 than I did in 2016. Honestly, it’s nice to start locking in the calendar this early. I know how much I can take on beyond this, and I will be able to schedule in some time to relax at somewhat regular intervals – something I’ve had trouble doing this year. I’ve had my nose to the grindstone almost non-stop over the last 18 months, and now that we’re starting to move into the holiday season, it’s nice to be wrapping up things for the year and being able to take a bit of time and consume content, rather than just create it.

Speaking of taking time to relax and enjoy the holidays, Thanksgiving dinner with my mom, brothers, and great aunt and uncle was great… at least, until my daughters got tired and started melting down. They got up way too early and decided not to nap, because they were excited to see their uncles. I knew that they were both ticking time bombs – they usually are when they don’t nap enough, even on a regular day. We’ll see how they do on Sunday afternoon when we have another Thanksgiving feast with another part of my family. Luckily, we’re going to that meal a lot earlier than we did at my mom’s house – 11 am versus 3 pm for dinner time.

I’ve already made two batches of my party mix, and I’m planning on making two more batches this weekend. Most of the family requests it over the course of the holiday season, along with my wife’s fudge (of which she’s already made two trays.) My wife will probably make most of the rest of her fudge this week during her last week of vacation before starting her “real doctor job” the first week of December, now that she’s done with residency after 5 long years. It seems like she’s having a lot of fun doing much of the stay-at-home parent stuff that I’ve been doing for nearly 5 years. I’m enjoying not having to worry about shuttling the kids places and making sure that the baby isn’t getting into trouble, now that she’s toddling around the house. Plus, once she starts her new job a week from Monday, her schedule will be the same every day – no more getting jerked around by the university.

I need to get to work consolidating everything that’s happened over the last year and actually get the Christmas cards done this year. I’ve wanted to do them for several years now, but I’ve never been able to find the time. We’ve done so much as a family and individually this year, it will be interesting to sit down and write the script for the cards. I haven’t done any of the Christmas shopping or any of the “Santa stuff” yet, but I didn’t want to deal with any of that yet during the Black Friday madness. I know plenty of people like going to the Black Friday sales, but not me. I did that once, and I will never do it again.

So much left to do before the end of the year. Let’s get to it!