We’re all Chicanos on the Train

We’re all Chicanos on the Train

At dinner several years ago with long-time friends, I dug into brick-oven fired pizza while we spoke about ethnic backgrounds. These were not friends who I’d just met or thought lightly of. They were good friends, people who contributed to our community, and who crossed paths in schools and churches. I identified with them, so you can imagine my confusion when one of them turned to me and asked: “So Sid, do you get offended when someone calls you Mexican?” My instinctive response was simple, but wrong on so many levels; and because of this, it has stayed with me these many years. Let me now share with you how I responded and how I think we all share a common card, and motivating force, as minorities of one type or another. My instinctive response My response was as bad as the question. I muttered, “No,” and then changed the subject. In doing so, I validated the notion that calling someone what they are can inherently be a bad thing. And, as it relates to my ethnicity, I perpetuated an existing negative stereotype. I moved to Utah when I was 4 years old–old enough to remember our orange trees in the backyard of our home in Whittier, California, and old enough to remember shying from my ethnicity as I acclimated to Utah. Technically (and I now have an ancestry DNA test that can show you all the beautiful detail) I’m ½ Mexican, ¼ Dutch, and ¼ German. My parents split when I was still young and I was raised by my mom, who hails from the Mexican side. And...
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...
Interesting Trends in Angel Investing

Interesting Trends in Angel Investing

“Tell me about your cap table?” I asked the Founder of an early stage startup. He was clearly passionate about his business, and had assembled a top-notch team to help him achieve his ambitious vision. But the grit and determination that had helped him overcome the challenges of his current and former startups seemed to falter a bit as he considered his response. He had a dirty cap table and he knew it. With some reservation he said, “Our initial angel investors own 60% of the company. I have 35%, and the rest is split up between the team.” He then went on to explain that their aggressive valuation was based on the growth since the last round of angel investment, in which the above-market revenue multiple the angels had chosen set the precedent. I soon found out that this team had struggled to raise money from the other venture capital firms with which we like to syndicate—because they, too, were dissuaded from the conditions that the angel investors had created: small runway, fragmented cap table, high valuation and little strategic support. He described with some frustration how he felt stuck, and that his ‘angels’ no longer fit the heavenly metaphor, but rather the situation felt more like hell. Compare and contrast this situation with a scenario that has become familiar because of it’s frequency within our portfolio of Peak Ventures-backed companies, in which an angel investor known to our team (and often an LP in our fund) introduces us to the founders of a company that he or she has backed (usually at an appropriate valuation for 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...
Entrepreneurship a Long Slog?

Entrepreneurship a Long Slog?

I recently ran one of those races that peppers obstacles and fear-inducing challenges throughout the course. One of those was the Muddy Mile, a long slog through waist-deep mud. The pit was wide enough for several people abreast, which gave cause for some funny moments. While most of us runners kept to the highest ground possible—which meant that we formed into a slowly moving line that snaked its way through the muck, a few brave and impatient souls tried to skip the line by running along side us through the untested mud. Without fail every one of these hit a deep pocket and promptly vanished from view as the sludge completely engulfed them. But those of us who stayed with the impromptu team could see from the people ahead how deep the mud was at those spots, and thus chart a good course. Reflecting on this muddy run experience caused me to think about the doom and gloom that has been in recent media outlets. It seems that the press increasingly views entrepreneurship and business creation as a long slog through icky mud with unexpected pits. Spectacular drops in stock prices like LinkedIn and Tableau caused reverberations across high tech, and SaaS valuations in general have now dropped 57%. The word “unicorn” now has a mixed reputation. And the fund raising environment seems to be tougher. So shouldn’t an entrepreneur expect a long slog right now, a seemingly hopeless journey of bootstrapping and organic growth? A Muddy Mile with hidden pits that will swallow them whole? No. This is the best time to start a business and get into...
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...
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