My Journey from Entrepreneur to VC: a Different Kind of High

My Journey from Entrepreneur to VC: a Different Kind of High

Checking my phone as I boarded a long international flight back to the US, I noticed a flurry of LinkedIn notifications congratulating me on my 2-year anniversary at Peak Ventures.   A rush of emotions hit me when I saw those notifications as I reflected on this path in venture capital, my transition from entrepreneur to investor, and what I’ve learned in these few years. Transition As an entrepreneur, I assumed that venture capital, though different, would have some of the same highs—and maybe even more of them on account of being involved with many companies instead of just one.  But although it’s been exhilarating in its own right, venture investing is a different high—more moderate.  As an entrepreneur, you experience higher highs and lower lows.  Everything rides on your business’s success– financially, emotionally and otherwise.  When things look bleak, desperation swoops down to grasp you in its painful claws.  And so too, when execution and opportunity align, exhilaration lifts you up to the thrill of the highest of highs. Venture capital is more like second-hand smoke.  Don’t get me wrong, I get buzzed with excitement every day in my line of work from the challenge-driven passions of the entrepreneurs we back (and in many ways I appreciate that I’m not a user of the entrepreneurial drug anymore)—but I’ve had to reset my own expectations of how I define success and feel joy.  It’s like transitioning from being the athlete on the court to coaching my 8 year-old’s team.  Hey now, don’t misunderstand and think that I’m calling any founders children… it’s just that I’ve experienced withdrawals from missing the...
Inside the Mindset of Top Young Talent

Inside the Mindset of Top Young Talent

Hiring veteran executives to fill out your C-suite is a luxury most startups will never enjoy.  Hiring young, untapped or junior talent, however, is a challenge that all startups face.  Moreover, growing green talent capacity into C-suite capability layers on yet another set of difficulties to the already strenuous life of a startup.   Navigating this is less science, more art. Some founders rely on being highly extroverted, others in having established credibility within specific industries or groups, and some—to some extent all of us–just power through conversations and interviews in bringing together that band of people who will man the boat and struggle to make it out of the tides and into deeper water. When we do stumble onto the winners in our teams, those people who seem to magically tackle anything thrown at them, retaining them is critical.  Losing them?  Unacceptable. Several years ago, while driving back to Utah from a team off-site, one of my colleagues, Caleb, shifted uncomfortably in his chair, and in a strained tone let me know that he had accepted a position at another company.  He was a natural star, a fast learner, and someone who lifted the energy of our team, so I was shocked!  I stumbled through a discussion over why he left and ultimately wished him well in the transition.  I think he was the first direct report that I had regrettably lost, so I didn’t feel entirely prepared for the difficult discussion, but fortunately for the both of us we parted ways on a good note, and our friendship remained intact. Fast forward a few years.  A group of...
The Beautiful Madness of March & Majerus

The Beautiful Madness of March & Majerus

March Madness is on!  Such a great time to enjoy college hoops, the powerhouse schools and the Cinderella underdogs.  I was reminded recently that few experiences prepared me more for startup life than my time 18 years ago as a college basketball walk-on and before the 1998 NCAA tournament. Last month I was in Phoenix, Arizona, for a board meeting.  The night before, at an evening EdTech meet-up hosted by CampusLogic, from the corner of my eye I caught what appeared to be an old teammate from my days playing basketball at the University of Utah.  “Tony? Nah,” I thought, but naturally I had to find out.  Sure enough, it was, in fact, an old acquaintance and talented teammate from more than a decade and a half earlier. We chatted for a few hours that evening and I was drawn back to stories and memories from my time around a legendary coach and remarkable team.  With March Madness descending upon thousands of us basketball junkies, here’s a reflection back to one of the many lessons learned on the court. Being a walk-on athlete coached by Rick Majerus left no room for a half-hearted effort.  And the result was special…   Basketball walk-ons, by design, have to fight for their place.  During tryouts it was an all-out battle to scrap for the ball, defend relentlessly, and hopefully sink a few buckets.  For me they also turned out to be a good excuse to remove the studs in my newly pierced ears (yes, my hallmarks of the 90s and college freshmanhood).  It’s a long-shot, maybe a crapshoot, to make the team...

The Flavors of Utah Venture Capital

This past week I spoke with a friend in New York City who was fascinated with the impressive growth of Utah’s tech companies, but (like many) was unfamiliar with how the venture scene has helped shape them. Those of us with roots in Utah tech are proud of what’s happening and can point to a time when things were different. You know: “Why, when I was raising money back in the early 2000s…” My friend is not unfamiliar with Utah or its people, so he understands some of the generally accepted reasons Utah is gaining momentum. The questions he posited to me were, “Who is funding these companies? What’s the venture scene in the state?” Similar questions hit me nearly four years ago, a few years before I ultimately made a career shift from full-time operator to VC. I remember a phone call I made from a Sheraton hotel room in the Winter of 2011. My startup had exited just months prior and this was a visit to our new HQ to get to know members of the new [larger] team. I called a long-time friend, and now my partner at Peak Ventures, to shoot the breeze. His business was growing well and he had started angel investing in the state. I was jealous- for many tech founders, the notion of backing the next generation of builders is 2nd only to the excitement that comes from building yourself. And, Jeff and I had a commonly-held belief that investing in the state was still in its infancy. Neither of us had found a perfect investor fit in-state. He had bootstrapped...

The Single Truth in Startups

A decade ago I embarked on the daily grind of the startup.  My company, Zinch (since acquired by Chegg— NYSE: CHGG), was hell-bent to change the way universities connected with high school students.  We aimed to bring ease and simplicity to a market filled with ignorance and complexity.  With visions of the impact we could have on millions of people who could discover the best university for their interests and potential, my co-founders and I sought advice and capital from the supporting system that prevailed in that day.  How different the startup world was back then!  Do you remember business plans (oh, the pain!)?  And how many hoops you had to jump through to raise capital?   Accelerators weren’t yet widespread  (Y Combinator debuted in ’05, Techstars in ’06, and in our state local accelerator BoomStartup didn’t start until 2010), venture capital under management was half of what it is today ($28B invested in 2006 vs. $65B in 2014), and the advice given to us seemed so formulaic (“Write a business plan, go win a competition, give away the majority of your company to us, follow only known pathways, and let us govern your operations from our perch on high!”).  Said another way, the journey of a startup was more arduous, less informed, and had both fewer mentors and capital support.  But at the time, it was hard to have this perspective, because being an entrepreneur, leaning forward, being face-down in the grind…I believed that the people in the know knew truth–that the formula for success would work–and who was I (young & inexperienced) to believe otherwise? Now fast forward...
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