Connecting The Dots

This post is a little longer than my usual paragraph or two so bear with me. It meanders a bit but finishes where it starts, a continuum if you will.

Ever since first seeing Steve Jobs’ 2005 commencement speech at Stanford, his words “You can’t connect the dots looking forward, you can only connect them looking backwards” have rattled around my brain.  Over the ensuing years, this notion has influenced how I’ve reflected on my life’s journey. If you’ve never seen it, I urge you to invest the fifteen minutes – it’s magnificent. From time to time since then, in an experience that I can only relate to deja vu, seemingly unrelated dots in my past will suddenly line up and present themselves; intertwined as if they were all part of a greater plan from the outset. This post outlines a recent example.

I’m an avid mountain biker and last week I spent some time diving into Google Earth trying to find some new trails to ride. What would later amount to an hour drive from home, I found a deep canyon and zoomed in to investigate. The first image is how it appeared when I discovered it. As you can see in the second image when I zoomed in closer and closer, it was apparent that there was a trail meandering along the creek that ran down the center of the fissure.

I told my brother-in-law Ben about it and on Saturday we ventured out to explore it. It turned out to be one of the best riding days we’ve had together in a long time. The canyon was simply stunning, offering us exciting & challenging riding while being quite desolate. While the trail wasn’t perfectly manicured, it was better than we expected and took us through some breathtaking landscape. We were treated to huge red canyon cliffs & walls more reminiscent of southern Utah than Idaho.

I digress, on with the story and a big detour. Back in 2003, Brad Schell gave my partner Phil and me a demo of SketchUp, the product he imagined when he founded @LastSoftware. It was the best live demo I’ve ever seen in my career. He put the mouse in our hands and in just a few minutes, we was created stunning 3D drawings. Shortly after, we wound up co-leading Brad’s Series A round of financing along with Jesse Devitte of Borealis Ventures.

Being investors in SketchUp started to bring us to Boulder regularly which ultimately led to meeting Brad Feld in 2005, who introduced me to David Cohen in 2007 (can you see the dots starting to connect?). I started hanging around the bunker, investing in some of the early Techstars companies including Everlater (co-founded by current Techstars Boulder Managing Director Natty Zola) and SendGrid. David and I were the original two board members at SendGrid and forged a great relationship during those early years. When I decided to wind down Highway 12 Ventures in 2010, David asked me to come join him at Techstars. The rest is history.

To fully connect the dots, Google acquired @Last Software in 2008, in large part because they had created a 3D plugin for Google Earth. The first image is what Google Earth looked like back then and the second illustrates the detail of the canyon we explored last weekend. The third image is a photograph I took of Ben as we entered the canyon.

Thanks in part to @Last Software, we were able to see this kind of detail and scout out a fantastic ride.

Ben entering the canyon

So how do the dots connect here? Pedaling up that canyon, I started thinking about the very small part I played in creating a 3D Google Earth which today allows millions of outdoor enthusiasts like myself to map out new adventures with just a few a few clicks. 15 years later, the dots connect from the canyon all the way back to that live demo, stopping along the way in Boulder and connecting to so many people there and how I ultimately wound up at Techstars.

For me, the most impactful message in Steve’s speech is “You have to trust that the dots will somehow connect in your future. You have trust in something; your gut, destiny, life, karma, whatever. Believing the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path. And that will make all the difference.” 

Outside of marrying Pam, some of the biggest decisions of my life (leaving a great job in Boston to live and raise our family in Idaho, winding down Highway 12 Ventures) were following my heart and venturing far off the well worn path. And for me – yes, that made all the difference. If there’s any advice I’d give to young people, it’s to follow your heart and believe that the dots will connect for you down the road.

  • Phil

    Sometimes it seems like even the most inconsequential decisions lead to exciting most exciting discoveries. Sounds like a wonderful ride, Pards.

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