After listening to others pitch me just a few completely different job alternatives whereas nonetheless at Google in 2008, it turned clear to me that I might make a greater resolution if I might absolutely discover the bigger panorama of recent firms rising in Silicon Valley.
I had spent the final a number of years specializing in Google’s enterprise outdoors the U.S., and I truthfully felt out of contact with the startup world. Past my objective of turning into a CEO of my very own firm, I had two different ambitions: I needed to assist construct a fantastic client service that might delight folks (doubtlessly in e-commerce) and I needed to construct additional wealth for myself and my household.
To higher consider my choices, I made the choice to give up Google first and discover a method to examine the broader ecosystem of firms earlier than selecting the place to go. Resolved to present myself a “clean slate” earlier than making a remaining alternative, I left Google after I was three months pregnant and joined Accel Companions, a prime Silicon Valley enterprise capital agency and an investor in my earlier startup, in a brief function as CEO-in-residence.
Within the months that adopted, I helped Accel consider funding alternatives throughout all kinds of digital sectors, with a selected concentrate on e-commerce, taking the chance to review these firms I would be part of or consider ranging from scratch.
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One in all Accel’s key companions, Theresia Gouw, helped me brainstorm, becoming a member of my cadre {of professional} clergymen. We had identified each other for over a decade (I initially met her as a younger founder at Yodlee) and had been at related levels of our careers, so I knew she might establish personally with my profession quandaries. Like me, Theresia was pregnant together with her subsequent youngster and at an identical life stage — yet one more commonality.
Picture Credit: Sukhinder Singh Cassidy
Whereas at Accel, I spent a disproportionate period of time testing my macro thesis that on-line buying was about to blow up in new methods. I had seen the rise of e-tailers at Google (many of those firms, comparable to eBay and Amazon, had been Google’s largest advertisers on the time), however most of the main e-commerce websites like Amazon and Zappos nonetheless had a utilitarian really feel to them.
In the meantime, new vogue and décor e-commerce websites comparable to Hire the Runway, Gilt, Houzz, Wayfair and One Kings Lane had been popping up in all places and rising quickly. These websites sought to faucet right into a extra aspirational and entertainment-oriented type of buying expertise and transfer it on-line.
Professional traders like Accel and others had been funding them, and my very own observations urged that this space would yield one other huge wave of on-line client progress. These way of life classes of buying additionally appealed to me personally; I used to be the goal buyer for a lot of of them.
I began to work on an thought for a brand new e-commerce service, a luxurious model of eBay, whereas listening to the pitches of each e-commerce firm that was in search of funding and speaking to a number of that wanted early-stage CEOs. I continued to take heed to non-e-commerce pitches as effectively, merely to present myself a degree of reference for evaluating on-line buying alternatives.
At Yodlee and Google, I had been fortunate sufficient to work with extremely good and gifted individuals who shared my values, and I needed to do the identical at my subsequent enterprise.
I needed to work with nice traders, too, and thankfully I had the flexibility both to work with Accel-funded firms, begin my very own or leverage different investor relationships I’d developed. I hung out with a number of firm founders to attempt to discern who they had been as leaders, along with what they had been engaged on.
By this level in my profession, I had a fairly clear thought of my very own superpowers and values, so I appeared to seek out firms that would benefit from my distinctive items and whose founders or senior leaders had strengths complementary to mine.
Particularly, I hoped to affix an organization with a really sturdy engineering and product administration tradition that wanted a CEO with technique, imaginative and prescient, enterprise improvement, fundraising and team-building experience. Making use of these standards, I turned down a number of alternatives at firms whose founders had talent units too much like mine, reasoning that this overlap would possibly result in battle if I ever turned CEO.
Lastly, I used my time at Accel to suppose lengthy and onerous concerning the dangers I might absorb turning into a startup CEO and whether or not I might afford to fail. My greatest danger by far was ego- and reputation-related. Aware of how precarious early-stage startups are, I feared that I would go away a profitable function as a world govt solely to endure a really massive and visual failure. However the extra I considered this, I confronted this ego danger head-on and concluded that my fame as an govt from Google would hopefully be sturdy sufficient to outlive one failure if it got here to that.
The private dangers of taking over a startup CEO function felt completely different however not higher than these related to my job at Google. Whereas I knew that serving as a first-time CEO whereas having one other new child at dwelling (my son Kieran) can be immensely traumatic, I might doubtless profit from not touring around the globe for days and weeks on finish and dealing throughout a number of time zones, as I had beforehand.
Final, I evaluated the monetary dangers of potential strikes. Though my startup fairness would have unsure worth for a very long time, I judged this a danger price taking, given how excited I’d really feel to have extra impression and duty as CEO. Whereas I misplaced a big monetary package deal in selecting to go away Google and switching to a startup wage, I might pay the payments at dwelling whereas digging into my financial savings solely barely. Underneath these circumstances, I used to be ready to make the leap.
In early 2010, virtually a yr after I left Google, I lastly discovered the best alternative and determined to affix vogue expertise startup Polyvore as its full-time CEO. A precursor to Pinterest, Polyvore was primarily based on the concept that ladies might “clip” on-line pictures to create vogue and décor thought boards digitally that had been immediately “shoppable.”
Thousands and thousands of younger ladies (together with influencers) had been already utilizing the service and beloved it. The founding crew was led by a rock star engineer, Pasha Sadri, together with three different product and expertise people he recruited from the likes of Yahoo and Google.
Pasha was identified for his intelligence, and we had linked informally over time for espresso, every time having nice discussions about enterprise technique. In truth, Polyvore twice earlier than had tried to recruit me to grow to be its CEO, as soon as after I was at Google and once more after I departed that firm in 2008. Again then, I’d spent a productive afternoon with the founding crew, serving to them suppose by way of their enterprise mannequin. I additionally knew Peter Fenton, one among Silicon Valley’s most profitable traders and a number one funder of the corporate. Peter was the one who first launched me to Polyvore and who continued afterward to passively courtroom me.
Having spent a lot time exploring my choices from a number of angles, I used to be now poised to make a fantastic resolution. I felt satisfied that e-commerce was beginning its subsequent wave of progress, and felt excited to be a part of it.
Inside that imaginative and prescient, Polyvore was among the many firms finest positioned to succeed, and I knew I might contribute in important methods to constructing a service that might delight tens of millions. I used to be impressed with the strengths of Polyvore’s founder and traders and anticipated that I might have the ability to complement their efforts properly. Recognizing that my success as a startup CEO hinged on my relationships with the founder and board, I had additionally invested time to get to know them.
In the meantime, I had confronted my concern demons, taking monetary danger however negotiating my supply aggressively to account for draw back situations I imagined, and coming to grips with my ego danger. With all this work in place, I lastly jumped.
After managing a multibillion-dollar revenue and loss and main a 2,000-person crew at Google, I turned the newly minted CEO of a 10-person vogue startup in February 2010.
As we tee up the larger selections in our careers, all of us face essential moments of resolution. No alternative we make will likely be excellent, and all of the frameworks on the planet received’t get rid of danger fully. However we don’t want perfection or freedom from danger. We simply must take the subsequent step.
By selecting thoughtfully, utilizing all of the instruments at our disposal to maximise our upside and anticipate our draw back, we are able to grasp the alternatives out there to us whereas equipping ourselves to deal with no matter challenges actuality throws our means.
Excerpted from “Select Risk: Take Dangers and Thrive (Even When You Fail)’ by Sukhinder Singh Cassidy. Copyright © 2021 by Sukhinder Singh Cassidy. Revealed and reprinted by permission of Mariner Books/Houghton Mifflin Harcourt. All rights reserved.
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