"Wrong turns are as important as right turns. More important sometimes." - Richard Bach
Life’s a bitch. It’s no secret. We ride the roller coaster daily. We’re giddy on the way up and terrified on the way down. No one is immune to the inevitable lulls. In recent memory I (was)
#bad
accused of being shady by a prospective customer, and
called selfish by my most important customer, my mom
forfeited a life-long friend due to a trivial, verbal spat that lingered and metastasized, and
went from making $3K per week in finance to $385 per week in unemployment
blindsided by the simultaneous resignation of my 2 co-founders while I was on vacation, and
duped by a well-known VC after they publicly awarded Sidewalk, my company, a $10K cash prize in a pitch contest and then sidestepped their way out of paying it
These were not easily digestible, nor were they deathly debilitating. The VC incident, in particular, still stings. While $10K is a trivial, rounding error for many, it represents 8 months of subsistence salary for me and thus is anything but trivial. Moreover, the ethical blow and relational disregard are the true travesties. I digress. We all face setbacks, most of which rarely make headlines. But over the years, a few lulls brought me to my knees.
#worse
In November 2012, the departure of both of my co-founders triggered a fire-sale of Sqoot. In some respects, I wish it happened earlier. The market moved so fast and we were so green that opportunities abound passed us over. After months of discussions and shopping the business, we entered into a LOI and exclusive negotiation with a well known, strategic acquirer. We quickly agreed on a modest, 7-figure, all cash, asset deal, and opened the kimo. We shared the intricacies of our publisher and advertiser relationships, stellar tech stack, pricing model, and sales and marketing strategy, the combination of which allowed us to punch well above our weight. We were told that our B2B focus complemented their B2C focus, our tech stack was a long overdue upgrade to their aging infrastructure, we’d be engaged as consultants to help with the transition, and that the combined companies would be the smallest, big fish in the massive offers space. We ate it up. We had no reason not to. A few days prior to executing an APA, the once crystal clear deal began to cloud up. Now, BigCo wanted to retain and relocate Sqoot’s team and add a substantial equity component, citing that their BOD was uncomfortable. In short, a 7-figure, all cash, asset deal morphed into a 5-figure, primarily equity, stock deal. I went from counting estimated payouts to investors and team to reminding them to count their blessings. We fervently rebuffed the offer. I was furious at BigCo for toying with us like a Great White toys with a seal before devouring it. We were adrift at sea, in a rudderless ship, with a beleaguered captain, no first mate, and a crew that long bailed. It turns out that the tides of acquisition, like the tides at sea, are notorious for shifting swiftly and silently. Just ask Andy Miller of CardStar, Alexa Andrzejewski of Foodspotting, or Chris Stanchak of TicketLeap. All that glitters is not gold.
#worst
As the son of a single mother, the brother to a sister, and a staunch liberal, never could I imagine that I’d be accused of sexism. On March 20, 2012, just that happened, and worst of all, it was true. In short, in an effort to hype a company-hosted hackathon, Sqoot, my company, used an appalling call to action in an event page. In hindsight, it was offensive, embarrassing, and undoubtedly sexist. I was a moron for not vetoing the call to action on the spot, a dud for half assing an initial apology, and an amature for underestimating the gravity of the situation. Upon realizing our horrid mistake, we immediately changed our offensive language, spent hours Tweeting “We’re sorry” to seemingly everyone in the Twittersphere, issued an initial response, and reissued a proper apology. At last count, 14K+ people read it but it was all for not. We were roasted at the spit both publically and privately, and mostly deservedly so. For a full blow by blow, just Google “Sqoot hackathon”. I personally fielded hundreds of inquiries from angry starters, bewildered friends, skeptical customers, and eager reporters. I even received a handful of death threats, which is never OK, but I was so numb that I could barely process them. I didn’t leave my apartment for almost a week but it felt like a month. It felt like the world was against me. I wouldn’t wish that feeling on my worst enemy.
You’re probably expecting an unlikely, happy ending. After all, that’s how these triumph after tribulation stories end right? Wrong. While I’m trying to put others first, my mom astutely reminds me that trying is far from doing. While I’m in a better place with Avand and believe he forgave my shortcomings, I still haven’t spoke to Andreas, my life-long friend. While I recovered from what was at the time a seemingly insurmountable economic blow, I gave up on pursuing that VC. My name is no longer synonymous with sexist pig, but my actions are permanent and unforgotten. While we eventually sold Sqoot, it was at a fraction of the price and more importantly, nearly at the expense of a friendship.
Life’s a bitch. Stay grounded whether you’re 456 feet up or 4 feet under.
