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 huge risk.

With just a few more details you’ll see how dramatically different this story of risk can appear.

You see, Anne is a repeat entrepreneur, having sold her last company to Monster.com, where she was a senior VP. Anne had lived in the Bay Area for years since her graduation from HBS, and Georgetown before that. In other words, Anne had a stellar career from the East Coast to the heart of tech in the West coast. When she joined our team, she moved to Utah, (which at the time wasn’t nearly as cool as it is now.) What’s more, she moved to Provo, Utah. And yet that’s still not all — I recall walking around with Anne, a single woman, and eventually finding a convenient residence for her in an apartment located in Brigham Young University married student housing! You can imagine, not necessarily what she envisioned in her career, at least geographically, I’m sure. Thinking back, I don’t know why she did it. But, I’m glad she did. A true pro, leaving the heart of tech where she had many offers, to join a startup in Provo, Utah, dominated by a group of young guys that sort of all looked the same.

I’m deeply indebted to Anne, and clearly see who was taking risk on whom.

If you are all-in, you will have to take risks on others, and they will likely be taking risks on you — whether that’s your boss, your employees, or your soon-to-be CEO.


Here’s a link to part 1 of this series:Whole-Hearted Risk: Problems to Solve & The People Involved

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About Sid Krommenhoek

Sid Krommenhoek is a repeat entrepreneur. Most recently Sid cofounded Zinch, an ed-tech company connecting students globally with opportunities in higher education, and led the company through concept, venture capital, international expansion, acquisition (Chegg, Inc.) and IPO (CHGG, NYSE).

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