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4 Things Startup Weekend Will Teach You (and why everyone should go at least once)

February 11, 2014

Over the weekend I attended Startup Weekend Honolulu—an event for entrepreneurs and entrepreneur wannabes to get together, pitch some ideas, and spend 54 hours working like crazy to build a deliverable. It was SO MUCH FUN! The event was hosted at The Box Jelly, a coworking space in Kaka’ako (very cool neighborhood with something of a hipster vibe). What the teams build gets presented to a panel of judges on Sunday night, and winners get bragging rights… along with some damn good experience if they intend to continue on with their business idea. Some teams come already formed, others form organically at the event.

Everything kicked off Friday night, and the place was absolutely crackling with positive energy and ideas. Entrepreneurs, social media personalities, spectators all worked the room, greeting old friends, making new ones, and talking about what ideas they might pitch. C and I made friends before we even walked in the door—and it turned out that the two people we started talking to were a) both military and b) one was from Manchester! I swear the world keeps getting smaller.

I jumped in with both feet and volunteered for the warm-up activity before the pitches. Just as an aside– if someone asks you to say a random word on ‘3’, don’t say hippopotamus. Or onomatopoeia. Trust me.

No, not Tiny Rhino.

No, not Tiny Rhino.

Pitches are quick—60 seconds to describe your project and ask for who you need on your team: designers and developers being the most in demand, with hustlers a close second. C & I joined the Team myFocusBook, an app with a new twist on productivity. Jenée Dana, President & Chief Focusing Officer of FocusOpus (the company behind myFocusBook) is an astonishing lady. At 29-years old she can already boast some pretty impressive career accomplishments, including a book that debuted at #1 on the Amazon Best-Seller List and a time management system that she created based on her own experiences at UCLA, where she struggled with ADD and undiagnosed reading disabilities yet still managed to graduate a year early. I met Jenée during the social portion of the evening and we hit it off, so I decided to jump on her team. We ended up with 5 hustlers (read: business people with zero design/development capabilities) trying to create a web app for her program. Them’s the breaks! Here’s what I learned this weekend:

  1. It’s not about the project: Startup Weekend is all about testing the waters of your idea to see what’s below the surface. People spend a lot of time thinking about their ideas, and it all comes down to whether or not they can convince anyone else that it’s got legs. There were SOOOO many interesting pitches that didn’t even get picked to move on to the second phase of the weekend. Despite the buzz of ideas, I think that the really important part of the experience is about your team. You will learn a lot about yourself working under pressure, and a lot about other people. I learned, in particular, what kind of people I don’t like working with. Knowing that is as important as knowing what kind of customers you want to attract. Thankfully, in real life it’s easier to pick your team with care and precision. When it’s time, do that, and avoid the blowhards who can’t focus.
  2. You learn more from losing: Not gonna lie—I bet that winning last night would have felt AMAZE-balls. They had big fake checks that they were handing out (even though no money was on the line), and I loves me some bragging rights. As it is, though, I learned so much this weekend that I can’t even be sad. I feel like my mind has been blown open to an entirely new world of possibilities that I was scarcely aware existed! Most people never see this side of the startup world. I heard about investors, ideation, and pitching pitching pitching. This is without a doubt the place to be for those wanting to dabble in entrepreneurial ventures, but come forewarned: If you’re transitioning from a more traditional field, as I did, prepare to do a lot of Googling—this is a whole new ballgame, complete with jargon. And remember that it doesn’t matter if your team “wins” or not. In startups, as in life, those who come with the desire to learn get more than those with the desire to win.
  3. Take the time to look at what other people are doing: Probably my biggest regret from the weekend is that I didn’t walk around more and see what other teams were up to. You shouldn’t make the same mistake! Get up from your table and go mingle—it will serve you well on several levels. Firstly, you need to work off some of the calories from the omnipresent pizza and donuts (p.s. the food is sooooooo tasty)! Secondly, it gives you the opportunity to meet folks and just chat, about anything really. Talking about the projects is great, but I overheard lots of interesting conversations and even managed to have a few of my own when someone new dropped by our table. Make the effort, stretch yourself, and you might even get a little networking out of it. You may also see what another group is working on and have an epiphany! Won’t know unless you unglue your butt from the chair, right?
  4. Network, network, network: I’ve touched on this a little in the other sections, but I think the biggest benefit to Startup Weekend is the opportunity to meet like-minded folks working on interesting things. My best connection from the weekend came out of the pitch session on Friday night—I met the woman who I think is going to become my co-founder on a new project. It’s all very secret squirrel right now, but I will share more when the time is right. What does this mean for you? Come prepped with business cards, a smile, and the genuine interest in what someone else has to say. That’s all that networking really is anyway, in my opinion.

Why YOU Should Go to a Startup Weekend

Fun little secret? You don’t have to participate to observe the pitches or see the Demo Day on Sunday afternoon. It was absolutely fascinating to see the variety and quality of ideas/pitches being presented, and I think it would be worthwhile for anyone to spend an hour or two listening to that. The things that come from Startup Weekend are The Next Big Things. These are the ideas, and the people, who will be changing your life (and possibly the world). Seeing that in action is priceless. Startup Weekends happen all over the world, and all around the calendar. Chances are there will be one near you soon, and I encourage you to go check it out, and maybe even participate.

Pro-tips if you go:

  • Try not to stand in the corner looking grumpy when your project isn’t chosen. We’re all grownups here.
  • Try to join a group that you’re actually interested in. Try NOT to work by yourself because of the first tip.
  • Try to find some way to be useful. C, who has absolutely no business background, still managed to be vital to our team in the research process. I saw several people, though, who just sat around/did nothing/left early because “there was nothing to do”. Find some way to be useful! Create a Twitter handle, or some other social media presence for your group. Go out and survey folks to get validation for your idea. Create a Kickstarter page. You get the idea. There is so much to do that doesn’t involve design or development! I had the privilege of listening to George Kellerman from 500 Startups at lunch on Saturday, and he reminded us that the only constraints on us were in our heads. This advice doesn’t only apply to the startup world. Remember that.

The biggest thing I got from this weekend is the reminder that you get what you put it. If you come to Startup Weekend with the intention of contributing, you will contribute. It works the other way too. So—what are you waiting for? Start dreaming now, and maybe at the next event it will be your team on the stage holding a giant fake check and a sense of endless possibilities.



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2 Comments leave one →
  1. February 11, 2014 17:26

    And now I wish I had gone to Startup Boston! Next year. Let’s start a biz called Bootstrap Sisters…

    BTW you want to write copy for my website?


    • February 11, 2014 20:56

      G, it was such an awesome experience in so many ways!! Definitely go. I suspect that each SW has it’s own regional flavor, so when I come home for good I’ll go with you! Also yes and yes 🙂 Email me!


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