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  • Writer's pictureAmi Kassar

AmiSight 6/12: The Strategic Entrepreneur: Ben Smith on Risk and Reward

Before starting this project, my basic understanding of entrepreneurial risk was that it’s highly calculated as opposed to brazen and impulsive. But what exactly gets factored into that calculation? The other month, I was thrilled to speak with Ben Smith, a very focused and conscientious entrepreneur with a background in project management and an unwavering commitment to processes. When I first asked him about which bucket he might fit into, it was no surprise that he took a moment to consider all the variables that play a role. This prompted some reflection on the subjectivity of risk: that defining oneself in a singular bucket can be ignorant of the nuance of challenges and how our approach varies accordingly.


As a specialized expert with a masterful technical skillset, Ben was happy to be climbing the corporate ladder for the majority of his career. But when a disappointing experience left a bad taste, he decided to pivot to entrepreneurship at age 54, a time when most of his peers were beginning to wind down. This again highlights the subjectivity of risk. While an intrapreneur might see founding a smaller business as a step away from the comfort of corporate support, an entrepreneur almost certainly is enticed by the ability to be in control of their day-to-day and business goals. For an entrepreneur, the risk of losing that control far exceeds any gamble that may come with running their own business.


Ben’s calculation of this acquisition risk included his previous work experiences with businesses around the globe, his trust in his highly developed skillset, and his process-oriented mindset that so often ensured smooth sailing. But he notes that his calculation was imperfect and that employing the right personnel proved to be a wildcard with a valuable lesson attached. As always, he mitigated this risk by falling back on process, evaluating his decisions, and adjusting his protocol. With this acquisition under his belt, Ben is ready and eager to take on another. He can now rely even more on a robust entrepreneurial skillset that’s been forged through trial and error.


Ben remains strategic and calculated in his desire to begin another acquisition, with a reasonable expectation of planning rather than acting on impulse. If entrepreneurship is a gamble, Ben will likely pass on games of pure luck and chance, preferring to play his cards at a table where he can employ his wit. This approach would grant him the same appealing level of control he first encountered a few years ago.

Check out the highlights of our conversation below!

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