Sauntering through a Startup Weekend in Wellington in 2020

Not everyone wants to be, or even should be an entrepreneur. But everyone should experience the process at least once.

Some Startup Weekend History

Startup Weekend was founded in Boulder, Colorado by an extreme minimalist and vagabond, Andrew Hyde, in July 2007. Coming from outside the tech world he saw how the hardest thing was to make a start.

He came up with a weekend. Start on Friday, pitch your idea, form a team, and be challenged to launch a working startup by Sunday.

He wanted everyone to know that the entrepreneurial path is not luck, that if you want to create your own future you can.

“People wanting to do what they want to do and making that a reality.”

In 2015 Startup Weekend was acquired and became part of the Techstars collection of startup programs. As of 2020 Startup Weekend’s have been held over 2900 times in 150 countries with over 190,000 participants. Not bad for a vagabond.

Even though Startup Weekend has become a global phenomenon it still holds true to its original ethos of being open to everyone, lots of ideas, lots of energy, lots of fun, and lots of pizza.

New Zealand History

I’m blurry on the exact genealogy of Startup Weekend in New Zealand. I was lucky enough to participate in the recent Wellington Startup Weekend. Which had representatives of every generation of facilitators from the earliest Dave Moskovitz, Dave Clearwater, Dan Khan and Lingy Au to the latest in Georgia McConnon, Lilia Alexander, Michaela Hing, Brandon Kwong, Travis Cornwall, Casey Davies-Bell and Ryan Walker.

There is actually a bit of a renaissance of Startup Weekend happening in New Zealand being driven by old and new hands.

The more competent the team, the more it disappears. There is a similar effect in technology, the better it works the less we notice it. The Wellington team came together and ran things as if they had access to alien technology.

Well setup, well catered, well laid out and well explained. Loads of fun.

The Experience

Wellington and Dunedin could be sister cities. But Wellington has the waterfront flavour of a low-rise Hong Kong with its mixture of old and new architecture. Startup Weekend Wellington was held at Victoria Universities “Orauariki Wellington School of Business and Government.” With picture perfect views of the Beehive across the street.

The complete list of facilitators and mentors stretched to over two dozen people, that worked with over seventy participants. All up one hundred people gathered on a Friday night and the crowd warmed up with a raucous session of paper, scissors, rock.

Forty brave people, with urging from friends and crowd, stood up to call out their ideas.

Everyone proceeded to vote with their feet and twelve teams were successfully formed… Caturdays, Connect, Drop, Flatmaaate, Food Stories, GEM (Greener Events Metrics), Hobby Swap, Mental-Match, Mohua, Sixth Official, Teafly and Weave Talent.

Idea Wall

Teams then morphed, changed names, team members, ideas and target markets as the weekend progressed. They spent the next two days furiously identifying markets, validating ideas, and crafting minimum lovable products. All the while sharpening and polishing their pitches.

Every team and every individual experiences a multitude of lessons compressed into a very short period of time. The pressure and the emotion can run high. Thankfully this weekend didn’t have anyone tossing their toys (it happens).

A small sampling of the some of the lessons and insights that occurred over the weekend…

Holding too tight. One participant said it was their second Startup Weekend. The first one they didn’t make it past the Friday night. Not enough people had chosen their idea to form a team and they had taken it to heart and walked.

This time not only did they loosen their grip but managed to form a team and let another member do the final pitch. That is some serious coming to terms with ones ego versus doing what’s required to get an idea moving.

Because our name. One team started with a name and that name had bound them to an understanding of who they were and what they were doing. They pounded against that trap all weekend. Until they realised it was just a name and what they were, was something completely different. It was like they had been uncorked and with only a few hours left they produced a beautiful pitch.

Bias. We are all biased to some extent or other. It’s how we act upon our bias that counts. That’s the point. One team had confronted this more than most and wanted to change it.

They started with an idea for education and moved forward to understanding there is real value in having different cultural, mental and physical views. If they’re accepted and applied with the right intent they can be a huge boon to companies.

Having powerfully different and divergent views incorporated into a team can reveal problems and solutions that no workshop of the like-minded ever will.

In a complex and increasingly diverse world this team wants to provide the talent that has the diversity to help companies navigate these biases positively.

Invert the paradigm inadvertently. Mental health is a major issue everywhere. What can we expect of a soft bundle with billions of wires and trillions of connections. Things get mixed up. One team was heavily focused on the people at risk and wanted to speed up their access to help. Delays can be disastrous.

In the process they started to look at things horizontally across the country and the idea to do some load balancing across vertical silos of counselling popped up. This led to an insight that helping the counsellors would help more. They flipped their target market.

Novelty and the obvious. Stating the obvious, is a novelty in itself sometimes, and we often laugh when someone does it. But just as often there is a truth in the obvious that we avoid approaching but is powerful when we do.

At least two teams produced the obvious, made us laugh, and made us all ask “why didn’t we think of that?!”

Stuck. Without fail every team got stuck somewhere. An idea, the market, a team member, team dynamics, an implementation, the message, the permutations are endless. Every team seemed surprised that they had got stuck, and every mentor smiled.

Working through the stuck is what starting up is all about.

Opposite inputs. A subset of stuck, every team had to wrestle with the opposites. Team members, markets or mentors (or a combination of all three) giving opposing inputs. Teams had to absorb and decide which input was best suited to their goal at that given point in time. This was fun to watch.

Sorting out the threads

The Pitch

Having negotiated their way through team building, cold calling, active (constructive) criticism, little sleep, much frustration. The pressure comes to a peak for the big pitch on Sunday night.

This isn’t a thirty second “hey this is my idea” this is the full blown five minutes in an auditorium, in front of a hundred of your peers, your friends, your mentors and the judges. This is pedal to metal and it’s the first time for most to ever publicly speak. Pressure!

And we are blown away!

Not a person in the theatre wanted anyone to do anything less than their level best. Hearts were pounding, breaths were held.

Absolutely every single speaker and team rose to the occasion and took it head on. Pitch after pitch (with some rather thunderous applause) was nailed.

You know you’re hitting home when the judges are asking for feature requests.

No one envied the judges Veronica Harwood-Stevenson, John Holt and Stephen Cummins task of trying to sift so many wonderful teams and ideas into some kind of hierarchy. In the end they had to add in a fourth place and a couple of (very well deserved) rising stars to get things in order.

Much applause, quite a few tears of joy, huge amounts of relief and (for those inclined) a very long night of celebration ensued.

The Community

If the teams think it’s hard work, wait until they try organising and facilitating one of these events. It’s a large organisational slog that begins months before, peaks for an intense 54 hours and then whiplashes into the event windup. Why would you want to do all that work of facilitating instead of just participating?

In his beautifully laconic way Dave Moskovitz summed it up with a single word “Naches.”

A Hebrew word, it’s the complete opposite of schadenfreude.

Naches is the joy you get from seeing others succeed.

It’s this kind of joy that attracts the right kind of people and why those people are such powerful community builders.

The Team

Startup Weekends are in marketing speak “the top of the funnel” they’re often peoples first exposure to startup entrepreneurialism and they send ripples throughout the community. They are fabulous, they compress a lot of genuine project based learning into a very short amount of time.

Never underestimate the power of community builders riding on a wave of naches.

A great place to find out when the next Startup Weekend will be happening is to subscribe to the Startup Digest NZ newsletter (follow the link).

Absolutely do make the effort to get along to your next Startup Weekend.


Startup Weekend International

Andrew Hyde


Startup Weekend Wellington

Startup Digest New Zealand




  • A massive thanks to Travis, Claire, Casey and Henna for putting up with me and putting me up.
  • Kieth Shering has the best job title.
  • Shannon Wray has the best housing solution.
  • Mandy Simpson takes her coffee very seriously and it was much appreciated that she wouldn’t accept any lowering of standards.
  • Marwan Jamal is working on his PhD so let’s all ask him when will it be finished? (note: don’t ask someone when their PhD will be finished).
  • Don’t pick a fight with Georgia McConnon, you won’t win. She was seen carrying the entire weekends kitchen supplies in one hand while talking on the phone with the other.
  • Michaela Hing is most likely to become CEO of ANZ, before she does a reverse takeover of HSBC.
  • Don’t get between Lilia Alexander and her camera. She will make you look wonderful.
  • Travis Cornwall should be considering TV.
  • Casey Davies-Bell should have bought his puppy along.
  • Ryan Walker should be in comedy.
  • Lingy Au is the only person who can run an entire Startup Weekend in Germany with only one word of German.
  • Brandon Kwong, you will be missed.
  • Never play paper, scissors, rock with Katherine Blaney.
  • Be very careful slipping out to lunch with Dan Khan.
  • Be very very careful celebrating with all of the above afterwards (5:00am finishes are harsh).
  • A big shout out to the companies and organisations that sponsor these events. Wellington was sponsored by Amazon Web Services (AWS), Raygun, Angel HQ, Storypark, Sharesies, Victoria University of Wellington, NZ Entrepreneur Magazine, Coffee Supreme and SkinnyFizz.
  • Apologies for any omissions. I didn’t take the notes I should have.


Postscript: After writing the above I got to wondering (I’m probably showing my ignorance so correct me if I’m missing something). What happens after? These weekends create some genuinely good teams and ideas, where do they go next?

Are they being followed up on?

Are there channels that are readily available to provide ongoing assistance?

Are there other entry level activities that run throughout the year that provide the same kinds of learning and mentoring?

Would something like this fit into a high school curriculum?

If you have some ideas or answers on any of the above, let me know.