Rejected: Unfiltered Tales of Rejection and Vulnerability in the Tech Badlands

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You have to admire their courage—after writhing in vicarious empathetic pain.

Ten speakers took the stage at the Venture This!: Rejected event on June 29 at the Hootsuite offices, part of a “live event series featuring real stories about life, love, and work experienced through tech-coloured glasses.”

Put on by Rain City Chronicles and Hootsuite Labs, the event featured speakers discussing their unique “entrepreneur’s journey,” experiencing rejection and developing resilience in the tech wastelands, and encountering the underside of entrepreneurship that you don’t hear about amid the noise of IPOs and acquisitions: the uncertainty, the unforeseeable circumstances, the unexpected snowballing, and the sometimes-messy intertwining of life, romance, and startups.

The event echoed the sentiment of James Altucher, the master of vulnerability storytelling, emphasizing that while there are a plethora of blogs and presentations that tell you how to create a successful business, very few explain what to do when you’ve sunk in the effort and it’s yielded nothing, or worse. As Altucher put it:

People always write me, “but how do you take that first step when you are lying on the floor.” They don’t add: in the fetal position, crying, drunk, poor, and so on. It’s assumed.

This series is here to put that in front of you, but with the softening effect of elapsed time and a dusting of humour to lessen the sting. The speakers are in the Vancouver community, with unique paths and narratives, but with the common experience of having to navigate events beyond their control or plans gone awry, all before the backdrop of tech, startups, and social media.

Without betraying the confidence of the speakers, as they only wanted to share their stories with the hundreds in attendance and the internet, here are a few of highlights that illustrate the content.  Imagine:

  • Going to New York to seek out buyers for your company in 2008, fondly remembered as a year of utter prosperity and joy.  But not only are you doing so in 2008, you’re landing on the tarmac the day Lehman’s collapses.  Not to be discouraged, you turn your eyes to London, only to land on the Heathrow tarmac the day the European markets collapse.
  • Joining a fund in 2007 that was revealed to be simple real estate flipper on a billion-dollar scale, and proceeding to leave investment banking without a job to go to, instead running to the mountains of Argentina to become a ski instructor, where an skiing anecdote encapsulated as much wisdom about risk as a career in accounting and investing ever did:  Don’t actually try to navigate the whole mountain in one go.  Go instead from the safe spot you’re in to the next safe spot that you see.
  • Having a meltdown while talking to national media after a social activism tweet goes viral and puts you at the center of a fiery and ongoing civic discussion, with powerful and high-profile advocates and adversaries insisting in polite and not-so-polite terms that you lower your expectations.
  • Realizing university doesn’t fit your character, and grappling with the assumption that you’re the square peg, and that more adjustment will finally enable you to swim effectively against the stream, only to finally admit a lack of ‘institution-person’ fit, leave the conventional path, tumultuously create your own across continents and companies, to ultimately land in a nice spot…for now.

The above is only a whisper of the richness of the personal accounts at the Venture This! event.  With humour and honesty, the presentations provided relatable, cathartic, and cautionary stories of adversity, of external and internal origins, and coming out the other side alive.

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