I Wish I Knew These Things Before Selling My Company Selling my business was a financially rewarding yet emotionally challenging journey. It taught me that, beyond contracts and negotiations, the hardest part is letting go of the culture, identity, and community I built.

By Kelly Bayett Edited by Micah Zimmerman

Key Takeaways

  • Assumptions can be costly – Clarify your long-term role before finalizing the sale.
  • Transparency matters – Keeping employees informed prevents confusion, and fosters trust during transitions.
  • Selling a business is a loss as much as a milestone.

Opinions expressed by Entrepreneur contributors are their own.

I always see a lot of information about buying businesses, yet there is a striking lack of resources dedicated to the intricacies of selling them. Having sold my own business, I can tell you that no matter how skilled your lawyers are in negotiating contracts, you may still have many questions, and those questions aren't always obvious. They are often emotional — ones that lawyers aren't built to address.

I started my business as a single mom with my boyfriend (now husband). We started in our rented house with nothing but a credit card and a pipe dream, and 13 years later, we built it into bustling recording and music studios in New York and Los Angeles. The company established a remarkable culture where everyone truly felt like family; many of them worked with us for a decade or longer. Deciding to sell was tough, but with another business thriving and my now being mom to four, I felt it was time and that I had taken it as far as it could go.

Related: Selling Your Business? Do These 6 Things Right Now

When we finally made the decision to sell, we were very diligent in our requests. We wanted to keep the company culture intact and ensure that our valued employees would not be replaced. We agreed that I would continue to be recognized as the founder, and both my husband and I would be involved for one full year to make sure the transition was seamless.

Looking back, there are several important things I wish I had known and done differently before selling:

With a five-year payout arrangement, I had assumed that I would always be somewhat involved as I still had an active stake in the company. An advisor eventually pointed out a harsh reality: my husband and I were essentially debt to the new owners and had no real power or say in the company's future. I was gutted, but it was also my fault. I didn't ask for involvement or say — I had made an incorrect assumption.

My name was removed from the site after the year was up. In fact, the new owners didn't want me around at all. We were cut off from everything. I genuinely wanted to remain involved; I missed the vibrant community we had built and, even more than that, the people who had become like family. But as they said, they had to rip the band-aid at some point, and they felt the year mark was it. I became depressed and felt like I had lost a piece of my identity. While they had every right to make this decision, my own assumptions about my role made it harder for me to cope.

I also had to let go of what I wanted the company to be and how it operated. The company I had nurtured with transparency and openness began to shift towards a more corporate environment under the new leadership. The initiative to foster the culture we had built was replaced with a more structured approach, with numerous emails and meetings outlining expected behaviors and processes — which was confusing to me. We had always simply embodied our culture without needing formal guidelines; we just lived it and worked through everything together. It felt more corporate than it had ever been before. But again, it wasn't mine anymore, and maybe this is what it needed to expand.

Related: What to Know About Selling Your Business

Since I assumed we would be involved until the payments were complete, I wasn't as open with the staff as I should have been about the sale. We had created a culture of transparency, and I thought presenting the new owner as our partner would ease concerns because my husband and I would always be there, and nothing would change. I also didn't want to create unnecessary fear among employees who were all invaluable to us. But by keeping people in the dark, we created confusion. Because we were a group that was so tight-knit, what we thought would keep people calm and together instead created panic and uncertainty. Looking back, I realize how unfair it was to them, and I should have been more transparent about the sale because people are intuitive and feel change. However big or small, change can make some feel unstable, and that is valid.

This entire process has been a battle emotionally, but at the end of the day, I am so grateful for the sale because I believe it did come at the right time. People always say, "You are living the dream! You built something from nothing and were able to sell it!" While that is true, it doesn't lessen the sense of loss I experienced mourning the business I built. For a long time, I felt like I was trapped in a dark cloud.

I struggled to find advice on the emotional toll of selling a business. So here's my two cents: While selling is something to celebrate (always), it's normal and okay to feel a sense of loss. It's okay to mourn — but always remember why you sold and the gifts that come with selling. Move through it to the other side, where you can let go and know that you have served the business and the people who make that business home. Remember, everything is going to be okay — because it always is.

Kelly Bayett

Entrepreneur Leadership Network® Contributor

Founder of Barking Owl and Managing Partner of Love Song

Kelly Bayett is Founder of award-winning sound studio Barking Owl and Managing Partner of newly launched production company Love Song. Over the course of her career, Kelly has built a reputation as a creative leader and mentor, as well as a passionate challenger of the status quo.

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