A Startup Retrospective

A few weeks ago, I started to pull back work on Vine Trails, and committed to just one day a week.

My co-founder Matt and I weren’t able to keep the same schedules – I was full time, while Matt was only available for a day. At the time I thought it would be better to change my hours to suit his, and have everyone progressing on the same page at the same time. But later, I realised that by agreeing to cut down my hours, I had actually declared that my interest was fading. It just wasn’t for me.

Everyone talks about the fact that you need to be really passionate about your startup idea to succeed, because things will get hard at some point. Your passion is what will drive you through the dip to see the other side. As the weeks progressed, and we learned more things, we adjusted the idea and the focus of the product. But Vine Trails was turning into something I was getting less interested in building.  I was running into barriers, and didn’t possess the drive to break through them.

My original idea was purely travel related – a trip itinerary generator. I wanted to build something that could answer this question:

I have three weeks for a holiday, and I want to go to New Zealand.

What should I do while I’m there?

That’s an enormous problem, and difficult to know where to start. So I decided to cut it down to a really focused vertical that was easy to define: wine tourism. Vine Trails was born.

The thing is, I really like wine. I enjoy travelling to wine regions and tasting wine. I would love if a product like Vine Trails existed already, and I would use it.  But there’s a difference between wanting to use a product, and having the drive to turn an idea into something real. I have friends who like to read about new wine releases, participate in forums, research wine regions, and subscribe to winery mailing lists. For them, that’s just fun and they love reading about it. For me, it would be necessary research rather than something I’d choose to do. When we started putting more focus on Vine Trails appealing to wineries, it just got less interesting to build.

I realised that the data element of the product is what I was passionate about – taking information about their wines and making it available in a new format, or letting people search through it in unusual ways.  I find analysing and visualising data really interesting – and it doesn’t really matter whether that information is about wine, or public transport, or economic growth. Making data accessible is where my interest lies.  I am passionate about data at a completely different level than I am passionate about wine tourism.

Lesson learned.

(Along with other things I learned about startups and team composition.)

Vine Trails still exists, in the capable hands of my co-founder Matt and my husband Niall, two of the biggest wine nerds I know. They’re both working on it part time, which means it will take a little longer to mature, but it’s definitely in the pipeline. I will be pitching in occasionally, but I won’t be the principal driver any more.

In the meantime, if you know anywhere in Sydney looking for data nerds, please drop me a line.

The Hipster, Hacker and Hustler

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.

On Starting Up

I’ve been working on my own project recently, a tourism related startup called Vine Trails. Its aim is to help people understand and navigate Australia’s wine regions based on wines they already like.

I’m really enjoying it so far, and feel like I’ve learned an enormous amount in the last six weeks. I love seeing what’s fun, what’s difficult, and what kind of tasks I enjoy doing.  It’s been an intense, energetic, self-driven and rewarding experience so far, with some occasional bouts of confusion, doubt and contradiction. Learning to manage the emotions around ups and downs is high on my priority list, but discovering that I am a good analytical business thinker is nice.

Hacking to Learn

I’ve learned that a lot of the early stages in a startup are basically hacking things together to learn something about your customer, or your market. It’s known as the “wizard of oz“. As a developer, I really, really, really dislike hacking things if I know I’m going to have to repeat it multiple times, so I found this stage of learning pretty challenging, even though I ultimately found what would/wouldn’t be viable in this process.

Shaving those Seventeen Yaks

I’ve also learned that startups are about balancing learning with action.  It feels like you need to explore seventeen different avenues at the same time, but how do you prioritise them all when you’re just one person? You want to know how big the market is, what’s the likelihood of conversion, what business model would succeed, where you can get the data from, who’s currently a competitor, how is your idea different, what problem are you trying to solve, how do you make it look good cheaply, and ultimately does the customer really want it?

Coding – Not Really That Critical

My biggest surprise is that most of my six weeks has been spent on research/thinking/analysis/adminstration, with only about 20% on code. Here is a sample of technologies or tasks I’ve worked on recently:

Code:

  • Twitter bootstrap
  • jQuery
  • AngularJS
  • Font Awesome
  • Node
  • Neo4j
  • Google Maps technologies

Non-code:

  • Hosting research – Heroku, Amazon, GrapheneDB, Bitbucket
  • Trying to work out a name (this is torture, since most of the internet is parked-up)
  • Reveal.js presentation framework
  • Domain name providers
  • Online wireframing – mockingbird
  • Design and colour schemes – kuler
  • Researching free HTML5 themes
  • Image providers / creative commons implications
  • Cost of freelancing for certain tasks – data entry, design
  • Researching wine regions
  • Writing up itineraries in wine regions (the “wizard of oz“)
  • Co-working spaces and trialling them
  • Building a lean canvas
  • Learning about startup accelerators
  • Looking at business cards
  • Researching statistics on wine tourism
  • Putting together a pitch
  • Going to networking/tech events – How to start up in Sydney, Women Pitch, SheHacks, SydJS, Women Who Code
  • Trying out Google AdWords
  • Researching potential revenue models
  • Registered GoogleApps for business account
  • Working out product/market fit for product iterations
  • Creating a mailing list organisation on Mailchimp
  • Google Analytics
  • Built & customised landing page
  • Investigating grants
  • Data entry
  • Checking out potential new meetups or events that are worth going to

Exploring the startup scene

I’ve enjoyed going to some of the entrepreneurial meetups, co-working spaces and courses around Sydney (at FishburnersGeneral AssemblyTank Stream Labs) to name a few. Taking the time out of your product development to explore the ecosystem is really important, to get exposed to new ideas and meet new people.  I’d even say that not doing this will lessen your chances of success dramatically.

Learning to Delegate, and Learning to Pay

Actually paying for something made me realise there was a lot of value in delegation. I’d rather spend the money on this service to solve my problem instead of trying to do it myself, or trying to shoehorn a free version into what I wanted to do.  There are loads of service providers that will help you bootstrap your idea, for example mailchimp for a free mailing list. It’s just a matter of researching what’s there for free, or deciding you are happy to pay for something that’s well-known that will save you time.

Keeping a Diary

I’ve started keeping a diary, just a sentence or two covering what I did that day, and how I felt.  It really helps to show me what I achieved in the last day/week/month. It’s nice to read over when you’ve had a crappy day.

The Non-Traditional Path

I’ve reached a point where I feel comfortable calling it a “startup”, but a lot of other people were calling it that before I was able to. I felt that there was a certain level of maturity needed to warrant the label “startup”, compared to a hobby you work on in your spare time. There’s also a lot of expectation from other people when you start calling it a “startup” (dealing with comments like “fantastic, tell me when I can buy shares!”)

While I don’t happen to be traditionally employed at the moment, in my mind I actually have a job, and I keep hours that make it feel like I have a job (though I am frequently thinking/researching at night or on weekends too). I appreciate my weekends much more when working on a startup idea. It definitely doesn’t feel like I’ve been on a weekly treadmill that will repeat exactly the same for the next 6 months.

Trying the startup life has freed me up to really think about what I like and want to do. I look at the few months I’ve had off as a chance to learn things I wouldn’t have otherwise, and they’re great. No matter what happens with Vine Trails, I’ve learned a ton.