Sleepless Nights

I have a lot on my mind these days.  My soon to be 18 year old son, who is graduating from high school this June, is still trying to figure out his path forward….go to university in the Fall, take a gap year, or a plethora of other good options.  As much as I want to figure it all out for him and make it “easy,” I know that I can’t.  I can guide, I can advise, I can help, but in the end…it his life and his decision.  We all want the best for our kids…but knowing exactly what that means isn’t simple or even maybe possible.

The unknown is stressful sometimes.

I am discovering that the same is true when you are an angel investor.  As I lay awake in bed at 4AM this morning, it struck me hard.  Over the last month, I invested a significant amount of my money in two separate early stage start-ups.  There is no product yet…just two great ideas that are under development, and that I happen to feel very connected to in purpose and passion.  Like my son, the path forward for these companies includes a lot of unknowns and, I am certain, ups and downs along the way.  There will be pivots based on new knowledge and experimentation.  There will be successes, and there will be failures.  It is all a part of the journey.

As a virgin entrepreneur and impact investor, all of these things seem very scary, yet, somehow invigorating.  After spending 20 years in the same business, doing progressively more responsible, but similar work…it is refreshing to venture a little deeper into the unknown.  By working closely with both companies (and directly for one of them), I have already learned so much in such a short period of time…including the nuances of the different types of  investment stages (Angel, Series A, Series B), Shareholder’s Agreements, building a company on a bootstrap, working with different entrepreneurial leadership styles, and so much more.

It’s not to say that there won’t be a lot more sleepless nights, as I continue down this road, and as my son navigates his way into adulthood. But, the benefits and the potential for success, financially, but more importantly, for the positive impact these companies (and my son) can have on the world, far outweigh the dark circles that appear every now and again under my eyes.

One thought

  1. Pingback: But It’s All A Priority! | TOSO

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