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Hindsight versus foresight: When people ask me ‘have I got any regrets’, or ‘what would you do differently?’ I answer philosophically – we made a few mistakes – some very expensive ones, but we still had to try them – they were all part of the learning to discover what next.

Without failures, of course we would not know success either.

There is one thing that I wish I’d got right. I wish I’d backed myself more… or just had a bit more cash to throw at the problem. That is the URL I chose right at the beginning in 2001.

The business was always called RedBalloon, but we called the product RedBalloon days (the product was  a gift of a ‘day’ – ie something to DO rather than a physical gift).

We did find that the URL was already registered to another business… so we settled for

Now with hindsight I can see that I lacked foresight. I should have approached the business who owned the URL to see if they would ‘sell’ it way back then.

A few things happened over the years.

  1. We started doing radio advertising and those in media said we needed a shorter URL for brand recall – our existing one was not ideal.
  2. We did brand research and found that we were being confused with a charity – (I had even had people coming up to me and saying – ‘I sleep my baby on the side’ – they had confused us with Red Nose Days)
  3. We wanted to be unique – and known to be an Australian/New Zealand business – and not confused with any other organization in other geographies that may or may not have the same brand reputation as us even though they were in a similar game.
  4. We began to provide experiences in a box and other experiences that were not necessarily a ‘day’. (eg an astrology reading or olive oil tasting)

So the approach was made and about 4 years ago we purchased the URL

My regret is not just for the wait for 5 years to purchase it – more the regret that it has taken another 4 years to truly get the brand return on this.

It was fear that stopped me from making the tough decision.

We had been working so hard for so long on our search engine position with Google we didn’t want to change anything. So we used the in all communications but then redirected traffic to the main original URL.

But given that we had formally updated our branding to drop the ‘days’ it was completely out of alignment with our brand voice.

So for the past 2 months or so – we have had very many, very clever minds working on the switch. That is to migrate our primary URL to being and referring all the unique ‘days’ URL through.

I shared the delight with our developer team as they learned, discovered and executed a program to migrate the URL… So last Saturday as we all crossed our fingers and toes the switch took place. Now 4 days after the migration we have not seen a dip in traffic, or a reduction in Google rankings. However they tell me that we won’t know for sure for a few more months. (Fingers and toes still crossed).

Sorry team that it was such a big job – when really it is something that could have been done 9 years ago. A massive thank you to the team for cleaning up my lack of foresight.

LESSON LEARNED: If you want to create something big – play a big game, make the investment needed. Big dreams – take big decisions, and resources.

Reader Interactions


  1. This is a nice story… and a type of decision that every startup entrepreneur needs to face. It starts with “do we get office space for the 3 people we are today or for the 20 people we plan to be?” “Do we work with the €2000/day lawyers who have done this before or the €300 flat fee friend who will do it instead?”. It is a dificult balance to play the right line between conserving cash and acting like the world’s greatest company in X from the start. My most recent challenge along these lines was “Do we get the trademark for our company in Spain, in Europe or go for worldwide?” This is a €2000 vs €20,000 decision….

  2. Excellent read. Thanks for posting. It’s amazing how ‘little’ decisions have such huge impact. Of course the issue is that in order to play a big game requires a larger investment which when starting up a business might not be an option.

  3. A lesson I am grateful that you are sharing today. I needed to be reminded.

    Can I add …..
    Big dreams – take big decisions, and resources…and guts .

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