First-time Tech Entrepreneur

First-time Tech Entrepreneur

Tuesday, 26 February 2013 00:00

Sleepless Nights, Three Business Decisions Keeping Australian Start-up Entrepreneurs Awake At Night: First-time Tech Entrepreneur Blog By Rebekah Campbell

Entrepreneurial insomnia

This article first appeared on June 26th, 2012.


“If you're not embarrassed by your first product release, you've released too late,” wrote LinkedIn founder and start-up guru, Reid Hoffman.


Today, I'm writing from my tiny hotel room in downtown Palo Alto.


We launched Posse two weeks ago and I can report that the time since then has been tough. Everything about starting this company has been hard: raising the first lot of money, hiring then un-hiring multiple people (lawyer, accountant, directors, staff, several technology partners), building the music product only to discover annoying barriers to scale, launching retail to discover customers didn't want to use it, running out of money, raising money again.


Now, it finally feels like we've nailed the right model, have an amazing team and are not about to run out of cash. I really thought that this would be the moment of bliss when everything falls into place. Like coming out of a torrid journey through the desert where you almost died several times, to discover water and a neatly marked track called “home.”


Sure, I recognise our product is still in Alpha, needs a lot of polish, and 80% of the features aren't built yet. However, I expected a moment of joy and peace where we worked in harmony with our users to iterate and evolve.


It would be like dancing, as the platform grew and became loved by all. Unfortunately, that's not how it works!


One question investors like to ask is “What's keeping you up at night?”


There's always an answer. Since launching our site two weeks ago, three things – other than jetlag – have kept me awake.


1. A series of small problems


I think it's important to set deadlines for teams. It helps to focus everyone on a common goal; without a deadline, things tend to slip. When you're burning through cash each month, slipping isn't a luxury you can afford.


So we set ourselves a deadline of 6.30pm on June 12 and stuck a big countdown ticker in the middle of the screen so no one could miss when we went live. We organised a party of friends and investors in our office to celebrate the big moment.


At 6.15pm, we had a call from a lawyer saying that – for various boring reasons I won't go into – we couldn't go live until 9.30pm: Very frustrating for a team who had worked day and night for two months preparing for this time! This was just the start.


My frustration over what happened next is half because I'm a non-tech building a tech company and half because, despite it all, I'm a perfectionist.


Mistakes upset me. As a non-tech person, I struggle to comprehend the immense amount of complex programming that goes behind creating a software platform like Posse.


I just see the end result and am frustrated when things go wrong: Links don't go where you expect; UI interactions that you think are going to make sense, don't; grammatical mistakes in the copy. And so on.


Our team built the site you see today in two-and-a-half months and we put ourselves under enormous pressure to get it out, so we could learn how people use it and make improvements. As such, we released a minimum viable product rather than a perfect one.


But I can't help it – I want a perfect product!


Late on the launch night, I noticed a hyphen out of place on the “about us” page, and that Facebook Share didn't work if you were on Safari. I lay in bed fretting about these things and lost at least half a night's sleep.


It's even more frustrating because, not being technical, I don't know how to fix those things. I don't understand how hard it is to avoid these pitfalls, so my tech team gets frustrated with my frustrations.


I've learnt in the past couple of weeks that moving fast is more important than being perfect. Our head of engineering, Alex, pointed out a Mark Zuckerberg quote, “Move fast and break things. Unless you are breaking stuff, you are not moving fast enough.” It makes a lot of sense.


Every week our site will improve, but there will always be mistakes along the road.


2. Reacting to feedback


Twitter criticisms started the day after we admitted people into the site. Some people didn't like the dog, one said our pivot was “hilarious”, others couldn't figure out how to scroll their town map.


Clarissa, who runs our Facebook and Twitter, also runs user tests and site support so she invited critics into the office to tell us their concerns.


In addition to this, we invited someone into our office so we could observe them trying to use the product every day. I think this process is incredibly important.


We take it seriously and do it well, but it does lead to conflicts over what to prioritise next.  If two people don't like the dog, should we lose the dog?


If people can't figure out how to scroll through their town should we change the layout of the town? Some people don't like the copy, so should we change it? All these criticisms make it difficult to decide.


I believe that you must respond to user feedback but if you respond to everything, you end up losing the vision for what you were trying to create in the first place.


This is where I think books like The Lean Startup fall short. Yes, it's good to launch early, track user interactions, measure and evolve, but this must be combined with a strong sense of product vision and company values.


Our vision is to build a platform that gives people useful, socially relevant search results, is fun for users to curate, and is both informative and useful for retailers. Our values are: everyone wins, delightful, revolutionary, excellence and integrity. We must iterate and we must react to user feedback but, at the same time, we must be steadfast in our vision for the company and our values. Otherwise, we'll end up with another bland product that is acceptable to everyone but delights no one.


We wanted to create a character (Elvis the dog) to direct users through the site rather than just have bland instructional pop-ups. We decided this would be a more delightful user experience, in line with our company values.


We also decided to charge forward and build key new features such as social search and retailer interaction as well as measuring and improving what we already have, because launching these features brings us closer to fulfilling the company's objectives.


It's a hard balance to manage, and everyone in the team has different ideas about what to focus on, but I think we've got it right.


3. Worrying about time and money


This is the third thing that keeps me up at night. At the moment, it costs around $120,000 a month to run Posse.


We gave up revenues when we decided to make the pivot, so investors and our Commercialisation Australia grant fund the company. As CEO, I have many responsibilities, but the number one thing is to remain solvent.


If we run out of money, we have no time for anything else. Until we hit sizeable revenues, (which we're projecting won't be until early next year) I'll continue losing sleep about running out of money. It will remain a huge drain on my time.


Right now, we're funded comfortably through to early next year but already I'm back in Palo Alto talking to investors. In fact, for the past week and a half of the two weeks, while we've been going through all the challenges I've listed (and many more!), I've been travelling, talking at investor meetings by day and to the team on Skype by night.


I realised that the moment where the start-up comes together with ease and grace never arrives. You never escape the desert. That glimpse of water on the horizon, the feeling that everything is about to start getting easier, is a mirage, cruelly designed to trick entrepreneurs into sticking with their businesses until they work.


Worse, this desert has mountains, and your start-up is a series of hikes over them. As soon as you've climbed one mountain, another lies right in front of you. It's bigger, too.


But, even through the stress and sleeplessness, I love this journey!


Rebekah Campbell is a music industry entrepreneur. She started out by organising a music festival to raise awareness of New Zealand’s youth suicide epidemic at the age of 19. In 2008, Rebekah came up with the idea for whilst promoting a tour for Evermore. Rebekah raised over $3 million from investors Australia and Silicon Valley to kick-start the business. launched in music in 2012 and in retail in 2012, with plans to expand to the United States later this year.

Comments (1)

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Hi Rebekah : )

I just wanted to say thank you for taking the time to share. I'm personally in the middle of losing sleep over multiple startups - But I just wanted to say - I found this blog? via a twitter link via... innovation centre sunshine coast... via their linked in profile...

The link was "Do you suffer from entrepreneurial insomnia" and it brought me here...

I was kind of hoping/expecting it to be a "how-to" style article about AVOIDING or EASING the insomnia hahahaha....

: P better luck next time aye?

I haven't slept properly for more than one or two nights at a time for longer than I can remember now - but I suppose one question I have for you is:

Do you have any tips and hints for helping to ease the struggles?

"A sacrifice isn't a sacrifice if you have a goal." Is one little mantra I picked up somewhere which highlights the critical impact of your perspective and or attitude - I suppose I'm just reaching out and hoping that somewhere in this microcosm of cyberspace a real, breathing person will find this comment!

Blessings and luck to anyone reading this : )

Shawn Michel , July 02, 2012
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