To sell or not to sell.
While it may seem like a no-brainer to say yes to an acquisition to the tune of millions—or even billions—it can be hard to later rest easy thinking about how much more you could have made independently.
Of course, in both of these instances, the founders are now members of the ultrawealthy and made far more by waiting versus selling out early. However, this isn’t the reality for everyone.
And while the payday was substantial, it was not as rewarding for the cofounders as they anticipated.
There’s no question that in each of these cases, the acquisition had a positive impact on each company’s overall success. And while the founders of YouTube, Reddit, or Instagram may have missed out on billions more in wealth (Systrom, for example, has billionaire status today), their early sell provided security, resources, and freedom that they otherwise might have never received.
It remains a nearly impossible game to predict if the startups could have scaled on par without their new corporate parent. But ultimately, these examples underscore just how the decision to sell can be one of the toughest—and most impactful—an entrepreneur may ever make.
