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Journey of an Entrepreneur

Journey of an Entrepreneur

I was speaking at the Heroku innovation lab for Salesforce last week – and whilst I had a wonderful time sharing my own journey, the real insights came from the questions asked of me at the end.

Brandon approached at then end as I sat chatting…. and he asked me “What was the pivot moment?” and I responded that we have adapted over the years but fundamentally there has never been a ‘pivot’ we are still in the same business servicing the same customers. He said “No, I don’t mean that, I mean that critical moment when you knew you would be okay?”. He continued, “For me it was when I realised people were all rushing around busy doing things – but I did not know if it was working or not — so I went to the reports guy and asked him to print out all the reports that he did every week and I shared the pile of documents with the leadership team and asked ‘which of these do you use all the time’, they responded ‘none really’.”

In that moment he realised that people did not know what the critical measures of the business were. They sat down and worked out that there were three numbers which really drove everything in the business.

“So we changed everything – the reports guy produced the three critical numbers and we got into the habit of meeting every Monday morning to discuss these critical numbers”. Brandon said, “This was the pivotal moment when we began to experience success – we went from losing money, being unorganised to focusing on the few things we needed to get done, it took another 15 months but everything changed.”

My pivotal moment —way back when at RedBalloon we put the Big Hairy Audacious Goal (BHAG) up in lights at the centre of the business. Anyone visiting RedBalloon saw the number and asked what it was… it gave every team member an opportunity to not only talk about the vision, our passion and the journey we were on — but we could always see our progress.

Our job as leaders is hard, but simple. It is about vision, values and alignment — holding people to the plan.

When people would come up with an idea or program, we would always check the scoreboard as if it was our north star and say does it help with this game — in or out?

I have been asked a lot about my ‘road to success’ and when did I know that ‘everything’ would be okay. This of course is never guaranteed. No business is ever set and forget.

Below however are some of the steps on my own entrepreneurial journey. They are not the ‘right way’, they are simply my way… but it might give you insight.

As I spoke to other members of the audience about ‘success’ I also reminded them that each of us is on our own journey and comparing yourself to others is not constructive. Your success is determined by what you said you wanted to do, be, have or experience.

So please don’t read the below and say “Am I there yet”. Instead, take a note book and reflect on those moments of your own accomplishment. When did you feel really great about something? Make your own journey of success… it is okay to reflect on your own fabulousness.

Here is a glimpse into my journey…


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  • Happiness:
Think less, Feel more;
Frown less, Smile more;
Judge less, Accept more;
Watch less, Do more;
Complain less, Appreciate more;
Fear less, Love more....
Give it a crack 😎on a weekend like this what's to stop you! #naturalbeauty #happiness
  • Friday drinks must be here soon surely ... or I'm out! #friyay
  • In the 90s I left my cushy job at Apple.

I’d be a squillionaire if I still had my stock options.

I don’t regret it. Here's why:

After 10 years of corporate, I wanted to ‘do my own thing’. I started with freelance marketing.

My strategy? Hard work and build strong brands.

It seemed to work - new clients came from referrals.

But after 18 months, I came to a realisation:

All my clients wanted was “more customers”, not complex branding plans.

SO I thought I’d build a brand of my own. Something to get them “more customers”. RedBalloon was born. The purpose? Give people amazing experiences.

16 years on, RB has delivered 3.8 million customers to 2000 small businesses.

Now, when I give talks, I always get the same question: “How did you build such a strong brand?” Funny how it comes full circle.

I can’t answer that with a time limit.

Though I think I found a way - an online course. “How to Build your Business Brand” - years of experience in one place (link in bio if interested). But, that’s not the point of this post.

If I stayed with Apple I’d be unbelievably wealthy.

Quitting was still the best thing I’ve ever done.

So if you want to take a leap of faith, do it.

All I ask you is this:

Trust yourself and never underestimate the power of brand.
  • #tbt the originals circa 2004 🎈 it reminds that an entrepreneurs journey is long and full of twists and turns. What a ride! @redballoonexperiences
  • I have always been rushing! I need to remind myself of this one regularity. I'm intentional, not frenetic. Choose the one thing that needs to get done to make everything easier! #inspiration


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