Build a Business Quicker Than Flight NZ1
The mentors at Startup Weekend Wellington

Build a Business Quicker Than Flight NZ1

Imagine having an idea for a business, validating it, assembling a team, building your product and getting your first paying customers - all in the time it takes to fly on NZ1 from London to Auckland.

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That’s the inspiring process I was humbled to be involved in last weekend. I was privileged to be a mentor at Startup Weekend Wellington. Not one, but three businesses got from idea to customer over the weekend. Still more had expressions of interest from customers, clients, partners or suppliers. All in less than 54 hours.

So what was it about, how did it run, and what did I take from it?

Startup weekend is a great mix of real-world entrepreneurship and business building, and deep-dive experiential learning. Real businesses, real lessons. It’s a safe (if intense) environment for anyone to bring their idea to, for exploration, validation, construction and feedback.

Friday 5pm-11:30pm

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It’s early Friday evening. Full of excitement and nerves, a roomful of people mingle and play a game of “Half Baked” to get the ideas and the laughs flowing. A long line of entrepreneurs is formed. One by one, they take the floor, with exactly a minute to introduce themselves and their idea, and share with us what skills they need - design, development or business. Quickly out of the room to draw up a poster for their idea, then back in to see the other pitches. All done! Now it’s time to mingle, ask, suggest, group, vote and form teams around the most popular ideas. We start with 13 teams for the weekend, 13 potential businesses.

Let’s go!

As mentors, after our briefing and intros, in pairs we mingle with the teams to ask, understand, challenge and support. The thinking, discussion, debates and decisions are flowing. It’s now around 10pm. In most teams, plans are afoot for how to validate ideas and assumptions in the morning. A few teams are making use of contacts in other time zones to run surveys overnight, to gain precious hours. Creative, I like it!

Saturday 8am - 11:30 pm

It’s the main day of the weekend. Judges will be looking for three things in the pitches tomorrow, and that shapes priorities for today. The three main criteria are validation, execution and business model. I’m fascinated to see how the different teams approach the work for today; especially those where the value proposition isn’t yet clear. 

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There is a good spread of pivoting through Saturday - some team’s ideas haven’t changed much. Others are quite radically different, now that a range of diverse experiences have fed into the discussion. We’re down to 12 teams now - one having disbanded overnight after considering more closely whether their idea would fly. That said, most of the team’s participants found other groups to join for the weekend. Sketches and ideas are starting to turn into slick mock-ups and viable prototypes. The day finishes with the very first practice pitches - the 5 minute presentations of the purpose, product and financials.

The mentors meet several times to discuss which teams might need what support, and who of us will be best placed to ask the right questions. We always work in pairs to help us make sure we don’t stray into coaching (or even directing). Our job is to use questions to challenge and support thinking, not help with making decisions.

Sunday 8am - 8pm

We’re at the sharp end now. Has the idea been validated enough? Have we learned things that mean our idea won’t actually fly? Will anyone actually buy our offering? And how the hang will we make money!? There are a lot of pretty tired people around, but huge energy. There are so many impressive brands, designs, and prototypes already.

Today is about execution and sustainability - the product and the business model.

There are two rounds of practice pitches through the day, then the main pitch presentation around 6pm. Today is when painful crash-and-burns turn into polished performances and slick start-points get even better. That most tricky of startup conversations - costs and pricing - tends to come late in the day for most teams, and causes some angst. Especially when the pressure is now starting to build around putting across a slick presentation. 

As mentors, the nature of our conversations is starting to change from challenging thinking to supporting and building confidence around strengths. Working in different pairs through the days gives us a huge amount of learning too, from each other and of course from the teams.

Cometh the hour, cometh the startup

It all comes down to this. It’s 4:30 pm on Sunday. Down tools and get back into the main conference room. This is it. No more time to debate, tune, validate, tweak or make decisions.

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Against incredibly tight timescales and against all reasonable odds, every team puts on a professional, authentic and believable pitch. It's fair to say there is a broad range of presentation styles... Three business have paying customers already. 

Viable businesses built in 34 official working hours in a 54 hour period.

What a stunning achievement. And what an incredible learning experience for everyone there. I know I learned a huge amount.

Is It For You?

Maybe my experience at Startup Weekend Wellington 2019 has inspired you to get involved, with an idea or as a mentor? Having mused on it, I wanted to share some of the things I personally took from the event. Some are learnings and some are challenges or reminders of things learned but perhaps not done as well as I could...

Ten Things I Took From SWWLG19:

  • The power of diverse teams - many people with the same goal but different view points can make amazing things happen by working together and looking at a challenge through different lenses
  • The value of validation - only customers can tell you about the true value of your offering, and sometimes they give you surprises (good and bad). Never stop listening to people who can explain what your offering means to them and their life.
  • The reward of totally focused time - most of our jobs ask us to balance time and priorities every day. How much could we get done if we parked the noise for just a couple of days, and instead focused the time on one single challenge?
  • The golden age of prototyping - the tools available now to turn ideas into compelling visual mockups and even working systems are astonishing. Time invested in learning some of them means ideas can be up and running as systems in hours, not weeks. Validation can be real, not theoretical.
  • Simplify, simplify, simplify - As an analyst, much of the mentoring I did was around clarifying propositions. Could the teams’ ideas be put in a way that a 5 year old could understand? That forces us to use simple words, clear concepts and hold on that side order of detail, thanks… The detail can be talked through once people are hooked on the concept.
  • Know when to talk and when to do - Some teams were 100% clear on their business idea by 10pm on Friday. Others pivoted several times during the weekend to find their core purpose and offering. Regardless of the journey, the teams that did best worked out when the debate was revisiting old ground, agreed on decisions and took at least some action to explore the route forward.
  • Being Socratic is difficult but rewarding - The first rule of Mentor Club is to only ever ask questions - to be Socratic. Why would we do this? (just my poor joke :) ) Ironically perhaps, I found this quite difficult having come from a few years in startup and growth businesses. I had to park the rapid “situation, options, decision, actions” directive mind-set I’d been in. I like asking questions anyway, but still I enjoyed the challenge of figuring out what line of questioning might help with the point I wanted to explain or explore. The weekend grew me as a mentor, I think. 
  • Mentoring - take a stand - Thanks to Dan Khan for this one! Dan’s advice to the mentors in our briefing was to stand whilst mentoring. If mentors sit down, we risk becoming part of the team and taking over or taking some ownership that is not ours to take. It also stops you hovering around and bugging the team when they just need to crack on! Great advice, bit trickier to follow when we were all tired on Sunday afternoon… :)
  • Generalism is a skill too - In a mentoring team full of talent in different spheres and businesses, I was really concerned that I wouldn’t have much to add. Sure I can ask awkward questions (that’s my job), but how would that help in such a focused situation? This was good for me - it forced me to think about how to up my mentoring game. The pairing of mentors also worked really well here - matching specific and general knowledge allowed the mentors to have really diverse discussions with the teams. I also learned and was reminded of a load of start-uppy things by being in these discussions.
  • Run with random ideas - some ideas pitched on the Friday night were the result of quite a bit of clear preparatory thinking. My favourite pitch of the opening night though was probably the last one, where the opening comment was pretty much “this idea has just come to me, what the hang I’ll share it anyway” - and that was one of the original 42 ideas that ended up as a business pitch on Sunday. Don’t miss flashes of inspiration just because they only flash once.

Keith Shering is a perennially curious analyst and imaginative problem solver. He's a Business Solutions Consultant at Redvespa Consultants Limited, based in Wellington, New Zealand. He's the author of "The Flow of Purpose - Design and build a better business through shared purpose." He hung his head in shame at Startup Weekend Wellington after what he saw the teams do in a weekend, because his first startup took years to build. At least his second startup took only 8 days to launch. Still, he’s marked his scorecard “must try harder” :)


Awesome write up Keith! A must read for anyone who wants an insightful look into what a StartupWeekend is.

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