How to Win Startup Weekend: A Good Team and a Little Magic

08/22/2015 | By Alexis Milesky

This post originally appeared on

The most frightening thing I’ve done recently also turned out to be the most rewarding.

About a month ago I attended a Startup Weekend in my resident city. I knew no other enrolled attendee and next to nothing about the process. But I had a keen interest in business, startups, and the unique opportunity SW offers to potentially build a business from the ground up. Within a weekend.

When I arrived on Friday night I was filled with a mix of anxiety, excitement and ambition.

I wanted some magic to happen.

After some ups and down moulding a good team, ours started working on a concept I felt had good potential. We were following the Lean Startup method and had worked out a problem, a solution and who our potential customers would be by the end of Friday night.

On Saturday morning we left the building to do some market validation. Unfortunately, after spending hours gathering data and customer validation we discovered that not only did our solution already exist, but in nearly the exact same form we’d envisioned.

We were disheartened and exhausted. But we still wanted to work together. We wanted to finish the weekend. We just needed a new business idea.

After a couple hours brainstorming over beer and craft hot chocolate we were left grasping at straws and coming up short.

We returned to the building together for what we thought would be our last meal as a team: fresh paella, a Startup Weekend Wellington tradition.

After the meal, we were prepared to disassemble and go home to a decent night’s sleep.

And then a little magic happened.

A Startup Weekend mentor approached us with some sage advice that changed our weekend.

She said, “I want you to know, every team reaches this point. Not only that, but every business reaches this point. When there seems no possible way forward and that no solution exists, it’s those who find a way and a will that succeed.”

Boom. We were back in. I forgot my own need to sleep and forgot the daunting fear of failure.

Our team chose to persevere over the remainder of the weekend and we pulled out a turn-around so profound that we earned the ‘Boomerang’ award from the SW mentors Sunday evening.

We were also the honourable recipients of the first standing ovation Dave Moskovitz, our lead mentor, longtime global Startup Weekend facilitator and organiser, has ever given a team during pitch practice in his entire Startup Weekend history.

And he stood and applauded us again when we were announced the weekend’s overall winner.

What began as an exercise to stretch my comfort zone became one of the most fulfilling 54-hour work periods in my recent memory. Meeting and joining the incredible team of my now-co-founders and winning Startup Weekend Wellington has started me (and I hope us) on a journey.

And I’m not sure that where that journey will take us nor where it will end. But I feel we can rest assured there will be more magic involved.

Co-founders of Voilà  (Team HousitLook at SWWLG).