Some Uber-Valuable Reminders + My Top 10 Entrepreneurial Lessons


Last month I was asked to deliver a masterclass on “How to Launch a Successful Small Business” presented by Uber and General Assembly (GA).

I’ve been a GA Instructor for a few years now so I’ve done a number of purpose-run classes where a corporate teams up with General Assembly to provide value to their clients, employees, or network.

But for some reason, when I turned up to the venue and the elevator doors opened up to a room full of Uber drivers, I was surprised.  I suppose I’d been expecting a mix of aspiring entrepreneurs invited from the network of Uber customers and GA students, not men and women who already have their own small businesses as Uber drivers.

For some reason, I instantly turned into “Negative Nelly” and thought, ‘Oh man, my presentation has not been tailored to this group. These people already have their own small businesses – they’ll be so bored.’

By the time I was on deck, ready to present, it was standing room only and I was still thinking that they were really only there for the free food.

But, boy, was I wrong.

When it came time to wrap up my talk and move into Q&A, I still had little indication that what I presented had resonated with anyone in the room.  I asked if anyone had any questions and for a few moments…. crickets.  I even started to slide stage left, thinking “oh well, job done.”

But then the floodgates opened.  One after another, audience members raised his/her hand — there were lots of “thanks”, questions and, best of all, stories of their own side businesses and ideas.

One man described how he’d just quit his job thanks to Uber and was now a full-time driver developing a startup on the side.  And, while listening to his story and the others like it, it struck me how in line the Uber opportunity is with the ideals that drive Workible — giving people the power to customise their own work lives.  Whether Uber is a supplementary income, a full time business or a means to another end, it’s empowering men and women to achieve their goals.

Even after the Q&A, I had a swarm of people continuing the conversation, swapping cards, and requesting the slides.

For me, the experience was a reminder of the futility of snap assumptions and the value of sharing our stories and knowledge, whether directly or indirectly relevant, because you never know when a lightning bolt may strike.

So, with that in mind, here are 10 of my own personal entrepreneurial lessons that I shared with the group that night:

  • Get uncomfortable — Never in my life have I been so consistently faced with opportunities to step out of my comfort zone as I have as an entrepreneur.  The more I take those opportunities, not only the less scary and more invigorating they become but they are the most sure-fire way to take a giant leap forward.
  • Don’t be afraid to ask. The worst that can happen is they say “No.”  — That goes for investment, sales, customer/ user feedback, employee engagement, partnerships and more.  You’re not going to get anything or anywhere if you don’t speak up. 
  • Do everything you can manually, then automate/ build. — You can waste a lot of time and money rushing to automate a process that you haven’t thoroughly tested.  Best to avoid shortcuts and understand the in’s and out’s first.  
  • Make it work, then make it better. — This one falls under the “fail fast” adage in startup world.  Don’t overcomplicate things.  Do the absolute minimum required to test and see if something works/ is wanted, then take the next step. 
  • You’re going to make mistakes. Mistakes are good as long as you learn from them and bounce back.
  • You can’t do everything, but in the beginning you’ll have to.  Know when it’s time to let go.
  • Your time is precious. Be picky with who you spend your time with (especially potential clients who despite loving you or your product – after weeks, months, sometimes years – just aren’t ready to buy).
  • Keep your competitors in your peripherals, but don’t let them distract you.  It’s important to know what’s going on in the industry, but if you’re always looking over your shoulder, how are you supposed to get ahead of the wave? 
  • Get out of your own way, stop worrying about “what if” and do what’s best for the business.
  • No one really knows what they’re doing.  There is no right time or perfect pedigree that prepares you to kickstart a new business – just jump in and get dirty, learn and fail, get knocked down and get back up. You’ll never regret it.
Some Uber-Valuable Reminders + My Top 10 Entrepreneurial Lessons

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