How I run a Startup Weekend

Before I get to the good bits, I’d just like to thank Shane Reiser for his “How I run a Startup Weekend” blogpost which was one of the first resources I read when I first started organizing, and is also the inspiration for this post. His account of how he tackles the Startup Weekend program inspired me to run my own experiments in organizing a Startup Weekend and have an observer’s mind that made me learn so much after each event no matter what role I played. Thanks for putting that blogpost together, Shane!

I’ve always personally considered the priority of a Startup Weekend to be the participant’s experience. After they leave our event, we want them to be empowered enough to start their own ventures, or become engaged members of the community.

A Startup Weekend event has the same core flow as all its other instances no matter where you are in the world. As Shane said, it’s really hard to f*ck up a Startup Weekend. It has email templates, checklists, guides, and sample pitch decks that make your life so much easier as an organizer. The only difference between events, I observed, are three things: 1) the event’s goal 2) the community’s culture and, surprisingly, 3) the supporters’ engagement.

I’d like to talk about my take on these three things, as I think attention to them is what makes my way of running a Startup Weekend slightly different. I’d also like to share these thoughts in hopes that organizers (or organizers-to-be) who are reading this will take a more flexible approach in structuring their programs; to still make it a Startup Weekend but to know that they very much have the capability to make it their community’s Startup Weekend.

The Event’s Goal

It’s important to define what the metric for success is in any kind of venture you start, even for events. Here are the goals I’ve set for past events I’ve organized to give you a better picture:

More than 70% of our participants are professionals
Any major department in government is involved before, during, and after the event
Have 60 students participate in all 3 days of the event not because they are required by their schools but because they genuinely want to

Hopefully those three examples give you an idea now of what I’m talking about. One event can have multiple goals, of course, but you can always start off with one and work up from there as you get more experience.

The importance of defining a goal is that it will give you a direction on how to run the rest of the event. For example, since I want 70% of my participants to be professionals rather than students, I’d decide to boost marketing efforts in cafes and coworking spaces instead of colleges and organizations. Instead of creating pre-events catering to beginners, I’d likely want to organize a more advanced prototyping workshop requiring participants to have moderate to advanced knowledge in design and development. It’s decisions like these that give an event a distinct flavor compared to past events, even though they have the same program.

The Community’s Culture

I always like to take into account the general demeanor of a community. Are people from this city naturally timid? Or are they an outgoing sort, already used to the startup way of things? Are there certain cultural norms that allow (or not allow) for certain interactions between participants?

Once I’ve gotten a general feel of the crowd we’re dealing with, I then work with the organizing team to make program, layout, and resource decisions that align with what we think is the best way to have participants engage.

For example, organizing a Startup Weekend for people in Bohol is still quite different from organizing a Startup Weekend for people in Cebu despite how close the islands are. Bohol is a more timid island and will probably not have as many foreign participants as Cebu so choosing to have mostly local mentors and adding one or two foreign mentors will be enough to keep things interesting but not too petrifying that participants are always on edge. The last thing we want is for them to feel too conscious about saying or doing the wrong thing in an environment that’s supposed to encourage crazy ideas and learning by trial and error.

I experienced this culture factor more strikingly when I had the opportunity to facilitate a Startup Weekend in Brunei. There are certain times in the day that called for “prayer time” and it was an important time for many of the participants (and the other inhabitants of the building we were holding the event in) so we had to make sure that there wasn’t any loud music or noises during those times. So workshops, major gatherings, and other activities within the program that required a lot of people coming together and engaging should be mindfully rescheduled to a different time within the event to be sensitive to the needs of the community.

It was such an amazing experience to see how the organizing team communicate to their partners to move the program points around to accommodate this schedule. It’s attention to nuances as big or small as these that really make a Startup Weekend your own.

The Supporters’ Engagement

“The community makes the Startup Weekend” is what I’ve always believed in, and bringing in important stakeholders to actively engage with the event gives so much value to both them and the participants’ overall experience.

An example of this are the mentors during Startup Weekend Cebu Youth who decided for themselves to try a new way of doing mentorships. Since many of them had already experienced Startup Weekends and similar programs, they identified problems they experienced during traditional mentorship sessions and proposed a new way of doing Saturday mentor sessions for our youth. They worked with the organizers in preparing materials and scheduling and managed to create an experience that lowered the instances of “mentor whiplash” where one participant is feeling confused as they are receiving critical yet misaligned feedback from different and disconnected mentors. It was a glorious thing to behold where everyone felt engaged and the participants really felt a connection with the mentors which boosted the kids’ confidence throughout the event.

It’s moments like these that you want to foster in your event, where supporters feel as though they’re as much of a part of the event as you are and that they’re not only there to give money and knowledge but to also make relationships with the people that are there.

I found that scheduling an evening mixer inviting only the committed mentors, judges, and sponsors to come together for an evening and have some drinks helps a lot in triggering collaboration. The format of the night is to have one speaker talk about the purpose of the event, who we’re doing it for, and what we hope to achieve, then leave the rest of the night to socials. What usually comes out of it are ideas like I mentioned above; efforts initiated by people that want to help make your Startup Weekend the best one ever.