Advantages of Being an Underdog: The Top 3 Qualities I Look for in an Entrepreneur

One thing that really gets me fired up is feeling like I’m an underdog.  I’ve felt this way most of my life, actually, regardless of the successes that may have come.  I need challenge.  I enjoy the fight.  Without a battle the wind goes out of my sails, and so sometimes I even create tension just to experience that positive conflict that helps my passions rise.  Reflecting on why being the underdog is so important to me, I’ve found that there are three fundamental qualities that an underdog develops in the quest for victory:  the will to win, the ability to lead and rally a team, and big vision.  These qualities have been essential to me on my own journey of entrepreneurship.  And therefore are the qualities I look for when investing.  Let me share with you what each of them means to me.  First, though, a bit of context. This is me as a high school basketball player.  At 5’8″ and 165 lbs. I felt like an underdog in every game.  This is Scott Pollard, 6’11” and 278 lbs., who you see here blocking Shaq (Scott is that big).  I played against Scott in high school, and remember one particularly painful moment when he dunked all over me.  As he landed, pounded his chest, and screamed in victory to the crowd, I remember feeling small and insignificant.  Nothing that I could have done would have blocked that dunk.  Sometimes you aren’t built to win, or at least it appears that way.  But if you are an underdog you have to find a way.  You’ve got to hustle and...

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...

A Powerful Lesson for Fathers-to-Be in a Startup

Last Friday at 3 am, baby Evie was born strong and healthy to the delight of her parents. Her father is a founder of one of Peak Ventures’ portfolio companies. Her mother is now a Mom of both baby and startup. The parallels between birthing a baby and a startup are rich and have been explored by many writers before. They are momentous times filled with excitement and dreams and trepidation! But I’m going to skip the usual metaphors in order to share with you a more personal and meaningful story. You see, the most critical role for me is also the one that ironically receives the least attention. It’s the mother! As a father of eight (four children and four startups), I had hoped that the lessons learned from one child to the next would be retained and improved upon, and ultimately lead me to a state of Leave It to Beaver-like parenting perfection. In reality, however, each child is unique, as are the challenges they bring. Responsibilities compound and distract, and frequently lead me to feeling unsettled and overwhelmed. You fellow entrepreneurs out there who have felt the low moments when your business and/or your marriages are reaching the breaking point know what I mean. These are hard times filled with tears and anxiety and confusion! Fortunately for me, I had mentors along the way who brought needed perspective through timely and spot-on advice when I needed it the most, and helped me to take care of the most important person for both my startup and growing company. Here’s a reflection on a few of those mentors,...

An Introspective Look Back: Peak Ventures Year 1

How do you celebrate your birthday?  It used to be cake, music and parties for me.  Now I prefer quieter and slower moments of reflection to look back and think about people I care about and the things we have accomplished together. During these moments I also account for the hard lessons learned in order to make sure I don’t lose the valuable impact people and experiences with them, have had on me.  A month or so ago, we celebrated the first birthday of Peak Ventures, the official closing of Fund 1.  I wish I could somehow give you cake and presents!  But in the spirit of reflection, here is something that’s hopefully useful:  some lessons further internalized & memories from our first year together. First, some background. Peak Ventures began on a solid foundation, namely 21 investments in what we now call ‘Fund 0’ that were made beginning in 2009–all in preparation for the raise of our official Fund 1. These deals have yielded great returns and are a testament to the strength of Utah entrepreneurship. A byproduct of this success is the lessons learned backing tech founders, including insights into governance, the types of entrepreneurs we love to back, raising rounds & exiting. The returns–coupled with the solid year-over-year performance of Peak Capital Partners–pushed us to formalize our venture activity in Peak Ventures. These combined forces made the road-show for Peak Ventures fun and effective, helping us to raise $23M in commitments within a matter of weeks. Utah seems to be a magnet for remarkable people finding their way back to the state and leaning in, and...

Never Make These 4 Startup Mistakes

In September of 2011, alone in Copenhagen after a full day at an industry conference, I sat in my hotel room on the phone with my good friend Anne Dwane. She was the CEO of our company, Zinch. For weeks we had debated whether to sign a term sheet for a series C venture financing or to sell the company, and this call was the news that our decision to sell was complete. Anne delivered it in her own style: factual, brief, and with a simple congratulations. It was all the call needed. I hung up the phone, paused for a minute, and then burst into tears. I didn’t know why I cried, but it was probably something between joy and cathartic relief. In those moments I experienced an overarching reflection on the 5 years of struggle to launch and build Zinch, the highs and the lows, the triumphs and the abject failures. As I looked in the mirror, so to speak, on my life, and who I had become, I realized that somewhere amid all of the good decisions, my bad decisions and mistakes had profound impact on me and my team. I want to share four of these mistakes with you, and I’m going to try to avoid the tactic of thinly veiling one’s strengths as weakness (you know what I’m talking about: the interview in which you’re asked about your weakness and out comes “I’m impatient for great results” or “I’m hard on my team and sometimes push too much towards success”).   No self-complimenting here. This will be raw Sid, mistakes exposed in all their ugly...

Improve Our Tech “Ecosystem” By Eliminating It From Our Rhetoric

I live in Utah, a state where 90% of what you find in the growing tech scene is fabulous: a strong pool of talent, willingness to delay gratification, and founding teams that think big. And my friends who’ve come from other states/countries and who’ve decided to lay roots here agree—we’ve got a lot going. Period. But not end of story. For us, there’s room to improve if measurable startup outcomes (or at least progress) are a priority. The principle of focusing on outcomes vs. activities was shared with me early in my startup by an investor and now friend & mentor, Chris Michel. Applying this within your startup is critical and, I’ve found, applying the same principles with external parties to your startup is just as critical. This world consisting of startups and the numerous (and growing) interested-in-startups parties is often referred to as the “ecosystem.” Looking back, I don’t think I ever used this term during my time as an entrepreneur. I only started noticing it when I moved to the investor side of the table. Now, ask any Utah investor or local talking head on our startup scene and they’ll inevitably use the word ecosystem. At first I played along, as it sounded nice, evoked images of squirrels and muskrats and plankton, and seemed to denote that we were all for one and one for all.   But then I noticed that many who spoke of the ecosystem seemed to be focused on that, sometimes, instead of building a successful service/product. For someone providing a service to entrepreneurs, that’s just fine. And it makes sense—build your network, work the...
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