Whole-Hearted Risk: Don’t Take Yourself Too Seriously

Whole-Hearted Risk: Don’t Take Yourself Too Seriously

Career risk is real and can be daunting– whether it’s risk-taking at your present job or starting a startup.  A few months ago, I was invited to share thoughts on the topic “whole-hearted risk” at a Women Tech Council summit held in Salt Lake City, Utah.  In the process, I realized that though it is difficult to isolate the risk I’ve taken, let alone give it so grand a descriptor as “whole hearted,” I am able to more clearly call out the risk taken by those with whom I’ve operated.  I cited three stories from different points in my last startup and have broken each story into three bite-sized blog posts.  Here’s the third… Part 3 – Life’s Too Short for Taking Yourself Too Seriously Final story, final chapter of our business.  Our company was acquired in 2011, which is a credit to Anne (see Part 2) and a stellar team, life-changing for us as founders, and a win for our other stakeholders.  I continued to build with the acquiring company for several years before our eventual IPO.  Part of that journey included plans for international expansion, which, at one point, meant that I needed to pitch the plan to my CEO. In the final slide of that pitch, I had a series of requests. My last request was for “our CEO’s blessing” on my plan. As I presented the plan remotely and over the phone, our CEO, Dan Rosensweig, responded, “Sid, how do Mormons give a blessing?” I was taken aback. “What?” I mumbled. He continued, “I know you’re a religious guy.  I’m a Jewish kid from New...
Whole-Hearted Risk: Those Who Take Risk on You

Whole-Hearted Risk: Those Who Take Risk on You

The second of three short stories from my last startup. Check back next Tuesday for part three. Career risk is real and can be daunting — whether it’s risk-taking at your present job or starting a startup. A few months ago, I was invited to share thoughts on the topic “whole-hearted risk” at a Women Tech Council summit held in Salt Lake City, Utah. In the process, I realized that though it is difficult to isolate the risk I’ve taken, let alone give it so grandiose a descriptor as “whole hearted,” I am able to more clearly call out the risk taken by those with whom I’ve operated. I cited three stories from different points in my last startup and have broken each story into three bite-sized blog posts. Here’s the second… Part 2 — Taking Risks on Others & Others Taking Risks on You As our young startup grew, so did the demands on our team and the needs in leadership. The needs of our growing business seemed to outpace our abilities as founders to scale with the business. We were fortunate to have a stand-out advisor who, just a few years into our startup, agreed to join as CEO as we charted rapid growth domestically and international expansion. Enter Anne. Thoughtful, intelligent, and as tough as nails. And yet our newest risk, or so we thought, was handing over the reins to someone different than us, not part of the early crew, and who we frankly had no doubt was capable but who we were still getting to know. At the time, handing over our baby startup felt like a...
Whole-Hearted Risk: Problems to Solve & The People Involved

Whole-Hearted Risk: Problems to Solve & The People Involved

The first of three short stories from my last startup. Check back next Tuesday for part two. Career risk is real and can be daunting — whether it’s risk-taking at your present job or beginning a startup. A few months ago, I was invited to share thoughts on the topic “whole-hearted risk” at a Women Tech Council summit held in Salt Lake City, Utah. In the process, I realized that though it is difficult to isolate the risk I’ve taken, let alone give it so grandiose a descriptor as “whole-hearted,” I am able to more clearly call out the risk taken by those with whom I’ve operated. I cited three stories from different points in my last startup and have broken each story into three bite-sized blog posts. Here’s the first… 1st Story — Problems to Solve and the People Involved A decade ago, my startup co-founders and I were young pups confident that we had ample resources to give our idea some lift- a little cash and some technical ability. What’s more, we were tackling a problem that all of us, the sons of 1st generation college students, could appreciate: a better way to find, choose, and get into college. We felt we were every bit the “young stars” that this magazine cover indicated. Only downhill from here, right? However, there came a time just months before this picture was taken and early in our startup, when my personal life came to a screeching halt with the unexpected passing away of my kid brother, Stephen. He’s is just four years younger than I. We shared a room growing up, so...
Utah Tech’s Tipping Point: For Founders, By Founders

Utah Tech’s Tipping Point: For Founders, By Founders

Co-authored by Andrea Houchens, reprinted from Silicon Slopes Magazine, Spring 2017 In 1994, Hush Puppy shoes were on their deathbed. They had sold a weak 30,000 pairs of shoes the previous year, and the parent company was about to kill the brand. Two years later they sold approximately 1.7 million pairs. Malcolm Gladwell, after recounting this story in his book The Tipping Point, then asked, “How does a thirty-dollar pair of shoes go from a handful of downtown Manhattan hipsters and designers to every mall in American in the space of two years?” The answer? Preferences of a few quickly escalated to the appeal of many, and tipped the scales to success. Without the initial interest of a handful of trend setters, Hush Puppies would likely have disappeared. Every entrepreneur faces the harsh economics of tipping points. In 2007, my Zinch cofounders and I had burned through most of our $750K angel investment. We needed to grow enough of a critical mass to survive. We needed a tipping point, but fighting on our own we would never get there. When we laid off most of our team—paying the remaining members in equity alone—it was local entrepreneurs who came to our rescue. They saw our potential and stepped in with capital and coaching. Their involvement tipped the scales, and the business was ultimately acquired and taken public. I remember like it was yesterday sitting in a Santa Clara hotel shortly after our company had been acquired, staring at a celebratory bottle of wine left for me (and that I couldn’t drink), remembering one of those who had lifted me up along...
Entrepreneur Is Just Another Label

Entrepreneur Is Just Another Label

This startup scene is familiar: we’re sitting on a comfy green couch in a wall-to-wall glass room; I’m surveying the room and feel at home. A dozen employees in an open work format sit on bar stools, with wooden floors below them, brick walls around them, and an etched wood carving of the company logo on the wall. Each employee sits in front of two screens, listening to music and chatting excitedly about the next product launch. Freshly Picked—a darling of the Provo start-up scene—has all the trappings of a successful, trendy, fast-growing tech company. The conversation, however, quickly reveals a difference in this startup, or at least its founder: the CEO talks about her startup success, and just as quickly transitions the topic to her other priorities, each just as important, some perhaps more so, than her successful venture. For most stargazing startup founders, achieving success comparable to that of Freshly Picked is a once-in-a-blue-moon scenario; Susan Petersen seems to have arrived, is relatively casual about it, and talks to us about other stars in the distance. In a community spilling over with startups, an all-in culture has emerged. Entrepreneurs make the company’s agenda top priority and tightly align those driving it. Commitment to a startup plays to our tribal tendencies and produces somewhat of a badge of honor. As a founder myself, I recall all the military-like comparisons: “I pulled the cord and left my job . . . I’m starting a startup!” “We’ve burned the ships!” “You’ve got to get in the trenches!” “It’s a battle!” You get the idea. And there is an all-out startup...
Out of the Office, Into the Paint

Out of the Office, Into the Paint

Two years ago we started playing basketball with local startups.  The purpose is to get to know people in a setting different from the way you typically meet VCs. It was spur-of-the-moment at first– a way to simply get a foot in the door with a company we were interested in. And all our team enjoy the sport, so why not? For me, it’s turned into something more fundamental to how I think about the relationships in my corner of the venture capital industry. This past week we enjoyed a best-of-five series with an exciting Utah company, ObservePoint (pictured). The time together was valuable, the sweaty exercise a plus. Here’s why: Know your people, business aside. I’m not talking about life philosophy or feel-good business tactics here. Look, every venture capitalist is in the business of backing great people. We all say this. And it’s not lip service. We track all our best deals back to remarkable individuals. Fighters. Scrappers. Winners. And if VCs at large are people-focused, then early stage VCs are hyper-focused. Why? Because with more business uncertainty & greater odds of failure that’s a recipe for “you better have massive belief in these people.” And belief in a person in the very earliest of stages is all about knowing everything you can about them other than their business. Their business has little to no history for goodness sake! I will frequently stop an entrepreneur from telling me about how they started their business to repeat, “No, please tell me about you, before your business, aside from your business, and what will make you tick after your business.” Press the flesh. A friend of mine and now fellow investor, Nobu, hails from Japan and happens to...
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