The term “Hipster, Hacker and Hustler” was coined in 2012 and describes the “dream” startup team. It consists of a hipster (designer) to make your product look great, a hacker to build it, and a hustler to think about strategy and marketing. Many VCs and seed funds swear by this mix, and admit that it affects your chances of funding and acceptance into accelerator programs.  After starting Vine Trails, I think I’m a convert.

Starting with a Team of One
I’m a software developer by trade, and I assumed I’d have a “head start” on creating a startup, because I have the skills to build it myself.  Plus, I could spend more time on fun things I actually wanted to build.

Nope!

I totally busted that idea within about a week. I was researching market sizes, volumes of goods, tourism numbers, checking out other competitors in the wine space, seeing how the existing industry worked, wondering how to build two sides of a marketplace concurrently, and how to attract people to a new product. I had lots to do, and was unsure of the best use of my time at any given point. Most importantly, I didn’t write a single line of code, unless you count a landing page (I don’t.)

Wanting to Share
About two weeks in, I realised I wanted a business co-founder, aka “hustler”. Someone who had skills in analysing a market, connecting with other businesses, or getting word out to consumers.  I lacked a lot of this experience myself, and it would be great to learn from someone else who’s done it before. I could also see the advantage of splitting tasks according to areas of expertise, achieving more in a shorter time frame.

Complexities
The tricky thing is finding your co-founder. You can’t pick any random person – it should be someone you respect and trust, has a complementary working style, and shares the same passion in the product as you do. Someone I meet at a hackathon is unlikely to fill that description. Also, someone who has my exact skill set isn’t going to add much diversity to the team – although it is more fun working with people you already know.

Every person you introduce brings a communication overhead, and potential divergence of product vision. There’s a chance you’ll move slower, because there are more people you need to convince before you try something. (Of course, there will be a lot of new ideas brought to the table too, which is both positive and negative as you’ll need to weigh up new ideas for goodness and feasibility.)  A couple of really interesting articles by SNTMNT and Derek Dukes talk about this issue.

There is also an issue of balancing time and dedication to the startup – what happens if one person has more time to dedicate than another? Or feels like they have more interest in the project, or is willing to invest more effort? No situation is perfect, and people bring their own imperfections to the mix as well.

Benefits
The immediate benefit I can see of the Hipster, Hacker and Hustler is keeping your momentum when you run into problem “X” – where X can be anything from “a good strategy for cold calling someone”, “analysing user metrics” or “how to make this cross browser compatible”.  Right now when I run into something I don’t know, I hit up Google, open about 10 tabs, read a bit, think a bit, find out if there’s any meetups about it, see click bait for an unrelated topic, read the twitter page for the author… and say goodbye to another hour of productivity.

If you split your tasks up, you can reclaim mental space that used to be dedicated to marketing, or tourism research, or whatever.  Sharing gives you more time and focus on what you do best. You also get the benefit of new ideas, another person who’s vested in driving the idea forward, and two chances of having a great day for the product overall.

My Experience
Vine Trails currently has one person who’s spent a lot of time on research and data (me), and two others who are part time enthusiasts. We’re definitely further along than if it was just a single person working on the product. However, we’ve had some hurdles too – everyone has different amounts of time they can spend on the project, and it can be challenging to bring everyone on the same page when we meet up. It’ll be interesting to see where we go from here.