5 tips for a successful Startup Weekend


Hi, you wonderful band of crazy, creative, off-the-cuff adventurers known as Startup Weekend attendees. This is Nat Finn. I wish I could be there in person. Life happened. I will be back for the Fall event come Hell or high water. For now, I’m manning the social media & blogs which means I get to give a little wisdom along the way.

I don’t reach out now as a volunteer but as a former winning team member of a Startup Weekend – Cincinnati. Spring – ‘13 to be exact. Along with Kelly Schwedland, the project we were on, MPlanner, went on to receive international acclaim and became a poster child for Startup Success before the project became open source.

Not bad for a team lead by a 14-year-old who just didn’t want to use a paper planner at school.

Below is a little of what Kelly & I learned that weekend

5 Tips to succeed in Startup Weekend Northwest Indiana

1 – It’s a marathon, not a sprint.

Startup weekend starts at 7pm on Friday night and goes all the way till dinner time early Sunday evening. You’ll feel the buzz to go all night, but if you don’t get a little rest then that long Saturday will feel like an eternity. You’ll end up sneaking off and sleeping a couple hours in your SUV during the afternoon. Ask Kelly! :-) (in his defense, he was allergic to cats, didn’t bring meds, and found out once we got to Nick Tippmann’s apartment that Nick’s girlfriend had a cat. BTW – thank you, once again for the crash pad, Nick!)

Kelly was the one with energy. I was the one that pulled an all-nighter before we drove down to Cincy. I was a zombie.

Don’t be like us!

2 – Practice your pitch on Sunday. Then practice again. Then, practice again.

You’ll have an instinctive inclination to believe you have until 5:30pm to get your idea ready for the judges. Bat down that instinct. The truth is you should be done with enough of it by 2pm so that the presenters can go lock themselves away in a room to practice the pitch because that 5 minutes is the biggest chunk to determine whether you win, place, show or settle for the connections you made during the weekend.

What we did: Kelly’s brilliance took this idea a step further. Once we had the idea drafted and a team working on branding, Kelly immediately started Saturday morning on a powerpoint presentation with some wonderful custom templates he had in his pocket. He researched along the way, made tables, marketing charts, and worked back and forth with members of the team coming up with catch phrases and hooks to make the pitch snappy.

Then, Sunday 2pm, Kelly took our presenters – and we only sent the two kids, Emerson and Will, to play on the judges’ sympathies. Kelly grilled them on the presentation. He helped them keep their tempo with the slides, worked on the timing of their one-liners, and had them practice to work on their banter so they could be like Lennon & McCartney on the pitch, Abbott and Costello on the jokes, and Jackie & Bobby during the salutation.

The result: while most had trouble getting halfway through their idea in the 5 minutes allowed and the rest had more unintended pauses than a Pinter play, Emerson & Will captured the hearts of the judges and, just as importantly, the audience. And they did it in 3:20.

3 – Think past Sunday. The judges will.

If you only think of how your idea will look to the judges on Sunday, you won’t be able to present a full solution. Think the idea through: product, price, place and promotion. Have the I’s dotted and the T’s crossed. Marketers: consider verticals, competitors, market penetration. The one with the math background in the group will need to validate any startup funding needed and why the product can be produced at the price point. A little supply & demand. The brand folks, defend the brand name. Tech folk, have a write up about the programming languages and methodology you used and why. “Because it is popular,” won’t get it done.

Everyone: Fraternity and Trust. Consider it.

4 – These judges and mentors have really been through it all. They’re the real deal.

Kelly used his vast connections through past startup ventures, his University of Chicago MBA network, his IU network and his Elevate Ventures venture capital connections to reach out to these judges. They’ve all been through the rigors – and that was just Kelly’s emails :-P. They’re going to be an incredible resource.

Two quick examples

1st example – Bart Loethen, Founder at Synergy Law Group: I first met Bart last year at South Bend Chocolate Company in downtown Valparaiso during the only blizzard that season saw. Steve Dalton (I think, unless it was Kelly) brought him in to see if he could help out. His resume is impressive. He was a mentor at the first Techstars Chicago weekend nearly 10 years ago. He still mentors the landmark event and if memory serves, some of his biggest clients have come from these weekends. He’s helped them from the ground up and now they’re producing and changing the world.

Best of all, Bart still keeps an office in downtown Valparaiso to go with his Chicago location.

Get to know him.

2nd example – Chris Bake, Senior Software Architect. Biziports: Chris started as a classical guitar major in college. Now, he is writing his toccata not in musical notation but in code while simultaneous backboning two product companies and an agency. He cut his teeth along with me and a couple hundred of our friends over the years in the cutthroat internet advertising agency. A client’s got another million dollar TV spend this weekend? No problem. Bake’s seen it before. He’ll see it again and again. He’s still takes his coffee the same way.

5) The simpler the idea, the higher the ceiling

Keep the idea simple. Keep the solution options open. Remember, you have 1 minute to pitch your idea on Friday night and, if selected, 5 minutes to validate it on Sunday afternoon. If you’re learning this for the first time, go lock yourself away in the bathroom and come up with a 30-word elevator pitch. Don’t worry about making it to perfect. Then again…folks love alliterations, but don’t go crazy. Natural voice. Simple tone.

Most importantly!

  1. Have fun! If your idea doesn’t get selected, don’t lose heart. Find a project you think will be fun and jump in. If you don’t like it, go to another.
  2. The weekend is a launching pad for ideas. Note there’s no silkscreen product facilities or paper mills in the building so your idea probably isn’t going into production right away. We did see someone bring in a 3-D printer to Startup Weekend Michiana, but that was for a prototype.
  3. Don’t be those people who walk out once they realize their cat app isn’t being built by Sunday. Such progress is rare. The intention is to test the ideas and get the foundation set. $10,000 in free production labor is a bit optimistic, the priceless connections are a realistic alternative.
  4. Meet the people. Become friends. Get their names and numbers. The weekend is for networking and idea building. Our hope is that both continues to happen once the weekend is done.

Have fun. Go crazy. Change the world. Remember to ask for the swag!

have-fun-at-startup-weekendA free .co domain and more await you. Get on Kelly and Karen for them.

Good luck!

Northwest Indiana and, hopefully, the world will be a different place once we’re done. That in itself is a beautiful thing. Here’s a toast to you. Sip. Drink. Gulp. Get started.