48 Adventure-filled Hours in the Valley

Little did I realize that my 48-hour adventure in Silicon Valley would begin with a run for the border.

We were delighted and a bit intimidated to learn back in October that BigRoad had been chosen to join 20 other startups for C100’s 48hrs in the Valley. The 48hrs in the Valley program, which has been running for about two years, brings promising Canadian startups to Silicon Valley to meet up with Canadian expats now living in California for two full days of mentorship, workshops, investor meetings and networking.

All kinds of questions were running through my mind when I learned of our acceptance to this elite, biannual program.  What should I say in my pitch? Will folks appreciate and “get” our business value proposition? But it never dawned on me to question the expiration date on my passport.

November 12 arrived and with my bags packed I headed for the airport – only to be turned away by border agents at Toronto’s Pearson Airport. Whoops. My passport has self destructed on October 30, just two weeks before my departure day.

With a tinge of desperation I headed via airporter to Niagara Falls, where I proceeded to make a second attempt to cross the border on foot traversing the Rainbow Bridge and paying 50 cents.  With the wind howling and hair blowing I made my border crossing. I was San Francisco bound at last.

With my travel plans just a bit unwound, I flew out of Buffalo via Newark New Jersey, arriving in San Francisco at 10:30 PM – alas, too late for the opening reception. The story proceeds to head uphill from here – fortunately for me and for BigRoad.



The C100 crew met the next morning at Rocketspace – and awesome accelerator for high growth tech startups to hear a presentation by Cassie Doyle, Canada’s consul general for the San Francisco Bay Area. We were joined at the event by many other Canadian entrepreneurs and regaled with stories and anecdotes from other alumni of the 48hrs program, many now rising stars on the Canadian tech scene, including Frank and Oak,  Shopify, Achievers, and Top Hat Monocle.  I was pleased and very interested to learn that the Rocketspace facility offers a Canadian Pavillion (CTA@SF) where Canadian startups can apply to participate in three-month sprints.

Business development advice and mentorship are a key benefit of the C100 program, and we had it in spades through our brief time in the Valley.  The Canadian e pat network and Silicon Valley entrepreneurs were incredibly open about sharing their war stories and experiences with their fellow wide-eyed start-ups.  We sat in on presentations from a wide array of tech gurus and companies including Jonathan Ehrlich, co-founder of Copius (formerly at Facebook, Indigo, Albright) and Ranjith Kumaran, co-founder of YouSendit and now Punchtab.

I can only characterize my meetings with mentors as truly amazing.  To an individual the folks we had the privilege of meeting were inspirational, generous with their time and very eager to assist in any way – including introductions to venture capital firms and other technology gurus.  Let me say now it is a good thing I am not a very wealthy man.  If I were, I would have invested in almost every entrepreneur I met.  I was simply dumbfounded by the innovation and creativity I experienced in so many different fields from all areas of Canada.

48hrs in the Valley enabled me to meet with corporate venture executives from from Google, Salesforce, IBM, Microsoft and to learn about each company’s investment criteria. With our pitches refined, we were off to Sandhill Road on a bus to meet up with our three assigned VCs. I was intrigued to learn that each firm was quite different, offering a unique “brand” experience, from the nature of conversation, to their attire, office décor, and architectural choices.

I then spent an extra day meeting with four other VC’s that showed interest in BigRoad, with the fourth meeting coming together at the last minute on the morning of my last day. The email request to meet arrived on my Android phone while I was sitting in a Starbucks in Palo Alto. Serendipitously I was only two blocks away from the VC’s office.  Within 20 minutes I was presenting my pitch. There’s something to be said about being in the right place at right time, and this bit of luck has me thinking that BigRoad needs to spend more time hanging out in Starbucks in the Valley.

My 48hrs in the Valley ended as it started – with a run for the border. Thinking I had time to kill before my flight home, I decided to wander the Stanford University Campus.  After spending too much time ogling the statues, the architecture, the grounds, and the beautiful California people, I turned to catch a cab – only to learn they are as scarce as hens’ teeth in that part of California.  So my journey ended with a three-mile walk, suitcase in tow. Red in the face, and desperately in need of a defibrillator, I finally arrived at the San Francisco airport to catch my red-eye flight back to Canada.


I can’t say enough about C100 team. The activities they lined up for us, the people we met and the value we were able to bring back is simply invaluable to our company. Atlee Clark, the entire C100 crew and its mentors were wonderful to deal with; selfless, humble, helpful, insightful, gracious and smart.

As a C100 48hrs alumnus, I am invited back to participate in next year’s events.  I’ll be happily involved in anything they ask me to do.

And rest assured my passport will be up to date.