What We "Lose" When We Sell Our Startup

"Is there any downside to selling a startup? I always read the big headlines about how much Founders sold for, but after that, I never really hear from them about how it went. Is there a cost to selling a startup that no one talks about?"

January 6th, 2021   |    By: Wil Schroter    |    Tags: Strategy

When we sell our startup, it's not the simple financial transactions we all think it is. While we zero in the wealth event and the "freedom," we rarely take stock of the significant cost that comes with it.

Our startups aren't just about an income stream — it's not just a job. It's a part of us, something we created from scratch and worked tirelessly to bring into this world (I'm really trying to avoid a child-birthing analogy, out of respect to any woman who's delivered an actual child!).

When we think about selling, we need to think about all of the things that are going to be taken away, not just the dollars and freedoms that will be added. We often find that our startups provide a much deeper reward than what just having a job implies — and we lose a lot in that process.

We Lose Purpose

Nothing creates purpose like the act of creation, especially when we're talking about startups. Everything we do, from registering that domain name to landing that first client to securing a little bit of investment feels like a rewarding step. Sure, there are lots of frustrations, but the payoffs are undeniable.

When we sell, we just don't have those same wins anymore. We try like hell to backfill those wins with a great day on the golf course or time spent with loved ones, and those things matter — they just aren't the same feeling. That's why most Founders after they sell invariably rush to start something else. We just need that sense of purpose back. We need the reward.

We Lose Importance

There's something powerful about being needed. At some point, it feels like a burden and a curse, and yet when it's taken away, we long for it. Ask any parent watching their kids leave home. The first week is all about "Freedom!" (insert Braveheart meme) but after that, we soon long for those silly conversations and engagements to pick back up.

Founders were the center of a universe for one moment and then irrelevant to that universe the next. There's something just brutally gutting about the title "Former" anything. It implies something has been taken away, and that loss often comes in the form of no longer feeling needed or wanted around something we felt so strongly about.

We Lose the Ability to Fill a Day

When we have zero free time, the idea of selling the business and having "all the time in the world" sounds incredibly appealing — and it is in theory. But the only reason it sounds appealing is because right now, we don't have that time. Once we're granted all the time, and we've caught up on our house projects, vacations, and NetFlix queue, we realize all of a sudden that it's really, really hard to fill 16 hours a day — forever.

Our startups not only fill up our time, they fill it up in a way that has purpose and reward. It's very hard for many Founders to find some sort of hobby or activity that consistently creates the same outcome for many, many hours every single day. When we sell, we're trying to eliminate the risks and frustrations, but we often don't realize those same risks and frustrations were the cost of having that engagement, to begin with.

We easily take for granted all the rewards our startups provided when — poof! — they all disappear. The only way we can truly appreciate the value our startups bring is to take a hard look at what we would actually be missing without them. It's often more than we think.

In Case You Missed It

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How Do I Get People to Take me Seriously? (podcast). Join Wil and Ryan as they take a deep dive into why it takes so much work to be taken seriously as a new Founder and what we can do to thumb the scales in our favor.

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About the Author

Wil Schroter

Wil Schroter is the Founder + CEO @ Startups.com, a startup platform that includes BizplanClarity, Fundable, Launchrock, and Zirtual. He started his first company at age 19 which grew to over $700 million in billings within 5 years (despite his involvement). After that he launched 8 more companies, the last 3 venture backed, to refine his learning of what not to do. He's a seasoned expert at starting companies and a total amateur at everything else.

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