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The burden of a startup CEO's roadmap

October 22, 2013 @ 8:43am

One of the best things about talking to the startup CEOs I advise is that they often remind me of stories or good advice that I've forgotten to share on my blog.

A few weeks ago I was talking to one of my favorite entrepreneurs. He was venting about some of the personality conflicts on his company's dev team and I knew he needed to switch to a positive perspective. So I had him step back and look at how far his team had come in very little time. I explained that a startup's roadmap can be defeating, but it's because you're on the inside. The outside world sees the three amazing products you've released, but entrepreneurs see the next seven they have yet to build — or even start. It can be difficult to pitch customers and investors when you have all those missing pieces cluttering your mind.

I told him that I have a trick to help me switch perspectives.

I imagine Steve Jobs in January of 2010 in a limo heading to the Yerba Buena Center for the Arts where he will announce the first iPad. During the ride he continues to rehearse his speech, using an iPad 6. His iPad 6 has a full color holographic projection of him delivering today's speech, plus interactive 3D playback controls. As the limo ride ends, he rolls up his iPad 6 like you or I would roll up a sheet of paper and he slides it into its special carrying tube, one that acts as both a wireless charger and a 6G cellular signal booster.

On stage, all he can think about is how heavy this first generation iPad feels and how crappy the 1024x768 screen is. It's a piece of junk. Who would buy this thing? But he takes a deep breath and reminds himself that his audience has never seen an iPad yet:

"iPad is our most advanced technology in a magical and revolutionary device at an unbelievable price. iPad creates and defines an entirely new category of devices that will connect users with their apps and content in a much more intimate, intuitive and fun way than ever before."

"It's very thin. What this device does is extraordinary. You can browse the web with it. It's the best web experience you've ever had."

Everything he said that day was true for everyone else on the planet. The first iPad was magical and revolutionary for the rest of us.

Just not for the guy with the iPad 6 in his pocket.

Update: I continued this post with behind-the-scenes stories from the launch of The Daily.

Newer: Launching The Daily

Older: Hack attack!