I’ve attended quite a number of events over the past ten years. Entrepreneurial events are the lifeblood of the community, bringing people together to create the kinds of “creative collisions” that can lead to great things. That’s why I run Startup Weekend events every year, in order to bring complete strangers together in order to spur ideas and move things forward. However, Startup Weekends aren’t the only way potential business partners can find each other. Conventions and Startup Weeks are both multi-day events that can get people together and talking.
I had a chance to attend three major nearby events in 2023 – EntreFest in Iowa City back in June, the Rally Innovation conference in Indianapolis in late August, and Denver Startup Week just a few weeks later in September. I want to compare and contrast these three events, covering what I think works for entrepreneurial events and what events need to do in order to increase the impact of their events on the startup community for the future. Some things are relatively minor – free coffee for attendees, for instance – and other things are somewhat major and structural. With any event, there is always room for improvement.
Headquarters
Every entrepreneurial event should have some kind of headquarters – maybe it’s the center of the convention hall surrounded by exhibitor booths, maybe it’s an unleased retail space used for the duration of the event, maybe it’s a tent. Whatever the location, it should be somewhere attendees can gather, do a bit of networking in between sessions, take a call or a Zoom meeting, or send some emails. Even at the most action-packed events, I’ve also found a session or two where there aren’t any scheduled talks that interest me, and I usually need a few minutes a day to triage emails – no lengthy responses, but just making sure that there are no fires that need to be put out. Occasionally, I have to hop on a meeting during a convention – there are some meetings that are completely impossible to reschedule. It’s nice to have a space, no matter how large or small, where this can be done during a convention or conference.
One thing that every convention HQ needs is free coffee. Most events I’ve attended have this small amenity. I was disappointed that Rally didn’t have free coffee or water – I was lucky enough to grab a free ticket through my work on their pitch competition committee, but there were some attendees that paid close to $1000 to be there. If people are shelling out that kind of money to be there, there’s a few hundred dollars in the budget for some coffee. To their credit, the venue in which Rally took place may not have allowed this – it was in a convention center, and all of the concession stands were open. However, I’m not paying $6 for convention center coffee. I specifically bring a travel coffee mug with me and fill up at the hotel before the walk over if I notice a lack of free coffee at the event.
Event Structure
The way an event is structured can make or break the experience. If there aren’t enough interesting sessions to attend, one can feel like the money paid for admission was wasted. If there are too many sessions, fear of missing out can kick in. It’s hard to know how good a session will be just by reading the description in the program or on the conference app. I’ve been to events where every session that I chose was amazing, but that is a rare occurrence. Usually, one or two sessions end up turning into complete duds – either the content being presented wasn’t as interesting as the session description made it out to be, or the speaker or panel just are not engaging. You walk a fine line each time you choose a session.
All three of the entrepreneurial events that I’m highlighting in this post had a wide variety of choices during the breakout sessions. However, only Rally and Denver Startup Week have the attendee numbers to justify the number of choices they offer each hour. One of the main complaints that I heard from my students last summer was that EntreFest offered too many choices, and in the sessions in which I presented, there were only a handful of attendees present in each session. In both my panel discussion on the first full day and my individual presentation at the end of the second full day, there were fewer than a dozen people in attendance. Reducing the number of sessions to fit the number of attendees should be a priority in future years.
Rally, on the other hand, had two or three presentations during each breakout session that looked promising, and each of those breakout sessions had attendance that filled up at least half of the room, if not the entire room each time. They seemed to lean more heavily into panel discussions than other conferences that I’ve attended in the past, which may have helped strengthen the schedule. This past year, Denver Startup Week had fewer sessions running concurrently than in past years – I hadn’t really experienced low attendance at any Denver Startup Week sessions in the past, but I don’t know what their registration numbers looked like in 2023 versus other years.
Staffing and Signage
Signs are a critical part of finding your way around an unfamiliar area, and for events looking to bring people in from outside the area, being able to find speaker venues is one of the most critical jobs that needs to be done. Most of the bigger entrepreneurial events do a great job pointing people in the right direction, with signs, banners, or flags posted outside buildings and next to conference rooms. The three events on which this post focuses all had directional signage and some signs outside the venues. However, there could always be improvement.
Since Rally was contained to one large convention center, signage was probably the easiest. Each of the breakout rooms had signs outside that were changed for each session, and at the center of the action near the registration desk, there were large signs pointing you toward the main areas of the convention – the keynote auditorium, the trade show, and the breakout rooms. Denver Startup Week probably has the toughest time with signage, as events are located all over the downtown core. However, there are usually banners or signs outside each of the buildings where events are taking place, and the headquarters is nicely signed. However, since many of the events take place somewhere inside large office buildings, the signage sometimes lacks clarity, meaning that a volunteer has to point you in the right direction.
EntreFest sits in between these two events – it’s not all contained inside one large convention center, but the events aren’t scattered nearly as widely as they are in Denver. Directional signage at the headquarters does the job of pointing you in the right direction initially, but some of the venues didn’t have any signs outside or inside the buildings, making it someone difficult for people new to the event or the area to find where they needed to go. Denver solves this problem with volunteer staffing at some locations, but that wasn’t the case for at least one of the venues in which I presented, which may have cut into the attendance for that session.
Volunteer staffing is the stopgap solution for that “final 500 feet” problem – once you’re in a building, where exactly do you go? Rally didn’t need this kind of staffing, since the entire program (except for a couple of external partners who were easy to find) was in the Indiana Convention Center. Denver Startup Week always seems to have enough volunteers spread throughout their different venues – usually the venues are the offices of sponsors, and the volunteers are employees of that sponsor business. The only event of the three that seems to have difficulty with volunteer staffing is EntreFest.
My solo presentation during EntreFest last summer was in a smaller room on the top floor of the MidWestOne bank building. It’s a room I’ve been in before, so I knew where it was and got there a few minutes early to get everything set up. However, there was not a volunteer at the door on the ground level, and no signage that I could find that would lead people from the elevator to the room in which my presentation was being held. I don’t know if this happened to other presenters during the event, but this is something that should be addressed. In previous years, it seemed like program staffers spent more time talking with each other than helping attendees find their way. I’ve brought this up in the past, but it unfortunately hasn’t been corrected in the present. It’s a huge area for improvement.
Keynotes and Big Events
Keynotes and big events are the most expensive part of running a large convention in a startup community. The keynote speakers are usually external to the community, and the big events are meant to showcase the best of what the community has to offer, either highlighting nightlife locations or other significant part of the entrepreneurial ecosystem – events like pitch competitions do this well, especially when held in amazing venues. Sometimes conventions can go a bit overboard with the keynotes and other signature events, to the point where you can end up with “keynote fatigue.”
I’ve found that one or two keynote speakers or big events per day of the convention works the best, usually bookending the rest of the content of the day. Rally went a bit overboard on the keynote speakers, with four per day. I would have rather spent some of the time at breakout sessions, as the keynotes were hit or miss. I didn’t end up watching any of the pitch competition, as so much time was already spent in the main room during keynotes, and I ditched out on the final keynote of the conference so that I could get back home a few hours sooner. In future years, I’m hoping that they cut the number of keynotes in half or drastically increase the quality of what they were paying for during those sessions.
Denver Startup Week this past September seemed to drastically scale back the number of keynote speakers, mostly through eliminating the kickoff breakfast on Monday morning. The kickoff breakfast was one of my favorite events in past years, even though it would start to drag toward the end. Having a cup of coffee and conversations in the cool mountain air in early fall made getting up a few hours earlier on Monday morning exciting. Also, the breakfast foods served at those events were usually pretty amazing. I hope that they reconsider having the kickoff breakfast in future years – hopefully 2023 was just a fluke, either due to a scheduling conflict or a funding issue.
Social events are also key to an amazing entrepreneurial event. Denver Startup Week leads the way in social events during those five days each year. There is always something to do each evening – from the big events on Monday and Thursday evenings to the happy hours and the art-focused after parties, I found myself out until the wee hours of the morning each day. There weren’t as many social events planned in 2023, which was a disappointment. I did make it to a pitch competition that also had a social hour afterwards, but the energy that had been there in previous years was lacking.
Rally and EntreFest both also feature social events during their runs. Midwest House ran a spectacular event during the entire duration of Rally, with special breakout sessions during the day and social events late into the night. There were also a couple of social events specifically put on by Rally, but I found that the Midwest House events were superior. EntreFest has no shortage of social events, and they tend to mix things up each year, which I appreciate. My students last summer were impressed by the number of opportunities they had to socialize with other entrepreneurs and creatives in attendance. We’ll see what they have in store in 2024 when the event moves back to Cedar Rapids.
Event Location
Location can make or break your event. Sometimes, large convention centers are the best place to hold an enormous entrepreneurial event. However, I tend to enjoy the events that take you outside and around the community more than events that are stuck in one space, where you are breathing conditioned air the entire day. If the point of your event is to highlight the best of your local community, you should bring the event to the different corners of the community, and this is a great opportunity for sponsors to get involved, such as is done during Denver Startup Week.
However, if your events are spread too far apart, this can lead to poorer attendance at the more far-flung venues throughout your community. When choosing sessions during Denver Startup Week in past years, I’ve had to be careful not to pick venues too far apart based on the amount of time between sessions. In 2023, they seemed to contain the sessions to a smaller area – perhaps attendees in past years had mentioned something about venues located too far apart. It’s always a shame when you have to choose whether or not to attend an event based solely on how far you have to walk or whether or not you have to find a ride share to get there.
The layout of a convention center can also hurt attendance at certain events. The part of the Indiana Convention Center that was used during Rally was one long hallway between the large ballroom spaces and meeting rooms, and both floors of the building are utilized along that hallway. Smaller sessions were relegated to the smaller rooms on the second floor, and a few of the rooms were incredibly far from the main areas where people were congregating between sessions. I’m not sure if there is anything that can be done about this in future years, and I’d love to know how the layout affected the attendance in some of the sessions.
Location can also refer to the city in which the event is being held. EntreFest rotates between Iowa City and Cedar Rapids. Downtown Iowa City is built for events like EntreFest – incredibly pedestrian-friendly with lots of restaurants and bars to take meetings and connect with old and new friends over a bite to eat, along with a selection of hotels for visitors to use. The NewBo neighborhood in Cedar Rapids features multiple through streets and empty lots, with only a small handful of restaurants and no hotels. The closest walkable hotel is twelve blocks away, with other hotels located miles away by car.
Conclusion
Entrepreneurial events are the highlights of any developing or developed startup community. They are great ways to bring together people from all different backgrounds and roles in the ecosystem, and these events are sometimes responsible for the creation of great new partnerships. While I’ve highlighted three larger conference-style events in this post, entrepreneurial events can take many different shapes. Most events are significantly smaller, on the order of 10-20 people. Community meetups, open coffee events, and Startup Weekends are great ways to catalyze your startup community and get people with shared interests talking to each other and potentially creating amazing new things.
If you have the opportunity to attend events in your entrepreneurial ecosystem, big or small, seize it. Participating in these events will show that the community supports the organizers’ efforts, and more events will take place in the future. If your community does not hold regular events, be the change you want to see in your community. A lot of work goes into these large events, so start small! Grab a friend or two and plan an informal meetup in your office, complete with coffee and donuts in the morning or a few pizzas and beverages after work. You have the power to make your entrepreneurial ecosystem the best it can be.