Successful entrepreneur Justin Dry speaks to honesty in startup culture

 In General

Justin Dry is very honest. He wants you to be honest?
But are we ready for honesty?

For the uninitiated, Justin is not just a passionate startup guy; as the Co-Founder and Co-CEO of Australian wine startup Vinomofo he has helped form ‘the ‘best wine deals website on the planet.’ Going great-guns in Aussie, the Mofo’s launched into New Zealand in 2016, in what can only be described as a boom of a year. I mean, how else would you define taking a cool 25 Mill’ (AU) in investment from Blue Sky Private Equity and launching into the goodness that is NZ in the same 12 months?

A year and a bit on, and Justin is sipping wine and spilling his guts in front of a room of Auckland founders, recounting tales of “when I lost everything for the second time,” the pressure, the stress and his lack of separation between work and life. As part of BizDojo‘s Founders Central Program, the inaugural Founders Night was designed to bring the founder community together – which involved networking, lots of awesome food, wine, a screening of The New Hustle, and a fireside chat with the man himself – Justin.

There were plenty of great lessons both in the film, and in the fireside chat that followed between Jonah Merchant (BizDojo Co-Founder and Co-Founder and Director of Founders Central) and Justin, and you can read about that around the ecosystem.

Justin talks on Founder Mental Health, as Jonah Merchant looks on.

But a thing that struck a chord with me was a topic we have heard mentioned before at meetups, with visiting speakers and within the people that call GridAKL / John Lysaght home. Honesty. This may seem inconsequential to some, I mean one of the first lessons you are taught as a child is not to lie, but in the startup world, things are sometimes not as they seem.

“New Zealand is really small, and everyone knows everyone. Something that I have personally found… and this is a little bit of a confession… people think we are doing amazing, people take what they see on social media and hear around the traps, and in your head, you are like – are you serious? How do you balance keeping people thinking that you are doing incredible work, and being honest about the fact that this sh*t is really, really hard.” – Audience question to Justin during the Founders Central, Founders night – fireside chat.

Justin, who by the time that the above question popped up has told us his life story. Shared details about losing everything, about his demons and the gory detail of the VinoMofo journey – including a hilarious story about a scooter and a Superman cape, which he follows-up with through gaps in laugher “do you think I’m crazy yet?” They are big on honesty over in Mofo land; it’s built into the way they do things, from how they hire and manage people, to how Justin and his Co-Founder relate to each other. Getting honest quick and getting sh*t on the table is how Justin puts it, and as he spoke there was a number of nodding heads in the room. Mine included.

But when the question above was asked, Justin responded “this is a hard one”, and that is because – it is.

The positives for increased honesty in the eco-system are abundant. They include the ability for people to learn real lessons from other founders. The ability to build trust, and therefore real collaboration and connection between businesses. Increased honesty could even create more avenues for support, and less of the “tall poppy syndrome” that so many talk about and experience. With increased honesty, founders could say “this is really hard and I’m having so much trouble with ____” , crowdsourcing solutions.

But, we aren’t there yet.

What followed after the question was a conversation about the need for founders to be honest, while also appearing confident, in-control and on the money for customers and more importantly investors, creating a complex tension.

So what were people in the room saying about the New Zealand founder community and honesty? 

  • To get buy-in to the dream, the general feeling is you have to be very positive about your position, but at what point does positivity become overselling?
  • Does talking about one’s business positively, getting great press, etc. give people a perception of you not needing help or support? Or even worse, does being more visible mean an increased likelihood of criticism, sometimes during some of your businesses most difficult times.
  • The startup community would likely feel more secure in general about their positions if people were more honest about their situations. This openness could create a community of real collaboration and support between founders.
  • Increased openness relies on an investor community that sees vulnerability as positive; not as a reason to skip investing.

If you are feeling as though you are left with more questions than answers, you aren’t alone. But these questions are now not ours alone, mind-benders to be debated internally (and eternally) between the time our head hits the pillow and we fall asleep.

Instead, they are, thanks to Founder Night, and Justin questions to talk about, thoughts to muse on and debates to have in the founder community.

While we may not be ready for radical, ‘get it all out there’ honesty ecosystem-wide – at least we are ready for honesty between founders, and maybe that is all we need right now?

This blog post was written by GridAKL / John Lysaght Building team member Anya, if you have a story you think she would love to write about tweet her about it.

Leave a Comment