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When Acquisitions Feel Hard

Over my last decade of coaching, I’ve worked with various founders whose companies were acquired. And suffice it to say the TechCrunch posts and LinkedIn updates do not tell the whole story. My intention in writing this piece is to help other founders anticipate what might be hard about acquisitions so they can “see around the corner” and feel a bit more prepared.
Here are 7 things that can feel unexpectedly hard about leading your company through an acquisition:
# 1 — When you’ve managed to land your team/product/brand somewhere, but it wasn’t a financially life-changing event for you.
There are several scenarios that can unfold where your company “gets acquired” but you don’t personally gain financially in a way that changes your life. (Note: Typically most founders think of “life-changing” as receiving the certain dollar amount that would make working for a salary optional for them for the rest of their lives. Everyone has a different number which qualifies as life-changing. Other, younger founders might define life-changing as something relatively smaller like “a cash infusion that allows me to buy my ideal house in my ideal location” even if that amount is well below “never having to work again” cash.)
Sometimes it’s not obvious to the outside world that this happened to you, so other people make inaccurate assumptions about your wealth moving forward. Sometimes what is hard is grappling with the ambivalence (i.e., feeling a confusing mix of emotions that don’t cancel out). You or your family may feel the increased financial pressure that has accumulated over years of working for below-market salary without the big payoff at the end. Other times, you are grieving the deep disappointment and loss of that financial upside while trying to celebrate the upside of being able to land your company somewhere (which so many other founders are never able to do).
# 2 — When the acquisition was a financially life-changing event for you, but…
Getting the huge financial upside isn’t without its own challenges:
Distance: Some founders experience an unnerving distance that a relatively sudden infusion of wealth can create. People start asking you for money (for philanthropic causes, for angel investing, for personal loans, etc.) in…