Investing your way to your next career step. Is it the future?

  1. Vice President, Fortune 500 — Several weeks ago I was talking with a friend and colleague of mine who happens to be a Vice President. We were catching-up about the goings-on in life, he knew of my private investing activity through 2c9 Ventures, and mentioned that he recently had the chance to invest in a local startup. His investment was substantial enough that he now sits on the board. Nothing surprising here. What was interesting was his perspective about how much value and personal learnings he gains from his experience sitting on the company’s board. In making this investment, is he receiving an equity stake in the company’s potential future upside, but he’s also invested in access to new education and relationships with other peer board members. Just from being involved in the quarterly board meetings, and wrestling with the questions management faces, he’s been able to learn a tremendous amount which he’s brought back to his day job. Now not everyone is a VP at a Fortune 500 company and therefore has the disposable income to make an investment sizable enough to merit position on the board of a startup. But that doesn’t preclude you from taking the same fundamental steps of aligning how you allocate your capital with your professional development and career goals. In this second anecdote, we’ll see how another investor landed himself a job.
  2. Senior Leader, $50M Startup — I was having another conversation this past week with a senior leader of a $50M startup and he casually mentioned — as part of his sales pitch — that he believed in the idea so much that he invested in their seed round, before he ever worked for them. He had a prior successful exit and was working for a large corporate when he decided to invest in a seed round of this startup. He eventually went on to take a leadership role with the company, leveraging the early investment he had made.

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