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,...

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...

Five Things to Expect From Your Seed Investor

It’s been nearly 8 years since I raised my last seed round and 1 year since I led my first seed investment. In both cases, the entrepreneurs were in their twenties, the businesses had interesting traction… and the companies faced some intense challenges. As an entrepreneur I can look back and draw a bit from those experiences, and now as I wear the investor’s hat I appreciate anew those challenges because I see the critical role seed investors play in backstopping founders solving big problems. What should an entrepreneur expect from their seed investor? Here’s what hits home for me, in no particular order: Safe conversations and tough love. I’ve never understood the posturing that occurs by founders to their investors–especially in board meetings. Summarizing events since the last board meeting or investor update would be ok if founders needed their backers to only serve as an audience…but in reality, they need to help move big rocks! So let’s talk less and spend more time finding the right leverage to lift those rocks. This means we have to talk and identify the obstacles, which requires trust and working through our discomfort in talking about sensitive problems. You get the idea. Maybe with partners, customers and all other external stakeholders, some level of puffing is to be expected, but with your investor partner, get to a “safe” zone early and often.  At the same time, your investor should not be a pushover—and you shouldn’t be looking for one. Presumably, when you raised, you did so knowing that you had blind spots and that new minds with and occasional muscle to...

Backing Degreed’s mission to jailbreak the degree

It’s a good night when you can enjoy college basketball at its best alongside friends. It’s a great night when you’re enjoying the game alongside friends like Chris McCarthy and others with whom I’ve worked alongside building businesses at Zinch, Chegg, & now Degreed. Yesterday, Degreed announced a series A raise led by Signal Peak Ventures in which we at Peak Ventures also participated; we are delighted to be one of the investors backing this amazing team. Here’s why: Vision: Degreed is redefining how we measure and think of learning. I met David Blake, founder and CEO of Degreed, in 2008 when he joined our founding team at Zinch. We set out to change how colleges viewed students-this was only a starting point for Dave. As he perfectly explained today to an audience at the ASU+GSV Summit, he has long held an interest in how we measure learning and education. That interest grew into a passion that has blossomed into an obsession. Simply put, whereas most of us default to where we went to college or what we majored in, one’s education is more completely captured over time by not only what we learn in a formal setting, but informally and through our experiences. Enter Degreed and their vision: “Jailbreaking the Degree.” + Execution: Dave’s vision for education is playing out after a gritty persistence that endears anyone familiar with Degreed’s history. Sometimes getting to execution is just a patient journey dotted with sacrifice. It’s hanging on long enough to find the right complementary pieces and partners. It’s finding the leverage in the business, and business model, that takes...
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