Selling a company you've poured your heart and soul into can be an emotive journey for any leader. It's a rollercoaster of feelings, often encapsulated in what's known as the grief cycle.
Selling a company might be hailed as a triumphant entrepreneurial achievement, but the underlying emotional turmoil is rarely discussed. Past the financial ramifications, many entrepreneurs grapple with a deep sense of sadness when relinquishing their life's work. In 2023, the small business acquisition market saw some stability, with 9,093 businesses sold in the US, a slight upward trend from the previous year's 9,054. The total value of these transactions escalated to $6.5 billion from $6.3 billion.
While these deals are prevalent, the emotional toll they take often goes unacknowledged. Kelly Bayett, co-founder of the audio post-production company Barking Owl, shares her story of selling the business and embracing her new venture, Love Song, alongside co-founder Daniel Wolfe.
“Nobody talks about the mourning part,” Bayett admits during a phone interview. “Everyone thinks selling a company is the dream, but there's this sadness of realizing it’s no longer yours. It’s like, ‘I built this thing, and now it’s gone.’”
The Bittersweet Goodbye
For Bayett, Barking Owl wasn't just a business—it was her baby, a testament to her creativity and collaborative spirit. The decision to sell took time and contemplation. After years of success and a team culture that felt like family, she recognized that the offer to sell aligned with both her professional and personal aspirations.
However, the sale definitely wasn't the end of the story. As Bayett explains, the emotional aftermath was a complex, heart-wrenching journey. The transition became particularly challenging when the new leadership brought changes that seemed to shift Barking Owl's culture—much like sending a child off to college.
“You’re still in their corner, but they’re on their own now,” she muses. Despite her attempts to remain connected, she felt the sting of separation, especially when realizing she’d lost influence over the company's future.

Embracing the New Chapter
Accepting and processing grief was a crucial step for Bayett. She grappled with profound sadness, from the absence of daily interactions with her team to the tangible ache of being replaced. Yet, she came to understand that loss is often a precursor to growth. “You have to lose something to gain something,” she reflects.
This realization allowed her to shift her focus towards Love Song, the commercial production company she co-founded during her transition. Love Song grew rapidly, drawing acclaim from major brands like Adidas, Vans, and Apple, and quickly became a formidable presence in the industry. Bayett poured her heart and soul into creating a company culture that mirrored the values she cherished at Barking Owl: mentorship, community, and, above all, love.
Building Love Song gave her a refreshed sense of purpose. “I see what I can do here,” she explains. “I'm taking a look at what the culture of Love Song is, and how can I make it culturally relevant, filled with love, and focused on mentorship?”
Among the Heartbreak and Hope
One key takeaway for Bayett is allowing space for emotions during transitions. “It's okay to mourn it,” she stresses. While the financial and professional benefits of selling are undeniable, she emphasizes that these choices also require emotional alignment.

She urges entrepreneurs to own their decisions fully. “You’re constantly torn by the decision you’ve made,” she admits. “But ultimately, the key is to focus on why you made the choice and what it allows you to achieve.”
At Love Song, Bayett has taken up the mantle of leadership once again, armed with a newfound perspective. Her experiences at Barking Owl continue to shape her leadership style, but she's also grown in ways she never anticipated. Letting go of her first company has offered her a more comprehensive perspective.
Lessons for Entrepreneurs
Bayett's journey presents valuable insights for entrepreneurs contemplating the sale of their businesses:
- Foster Emotional Resilience: Embrace your emotions as you journey into the unknown, understanding that tears are part of the process.
- Keep your Eye on the Horizon: Look beyond the present and focus on what lies ahead, aiming to shape your new beginning with purpose and optimism.
- Cultivate Values: Keep your core values at the heart of all your ventures, ensuring a sense of continuity in your leadership and vision.
- Own Your Decisions: Your exit strategy should be a choice driven by both your professional ambitions and personal priorities, leaving you in control of your journey.
Selling a company built from the ground up is more than just a financial transaction; it's a deeply emotional and professional milestone. By acknowledging and navigating the complexities of such transitions, entrepreneurs can move forward with strength and resolve.
“It’s okay to be emotional about it,” Bayett concludes. “Mourn it, but don’t lose sight of what you can build next.”
- Kelly Bayett, co-founder of the sold audio post-production company Barking Owl, now focuses on Love Song, her new venture with Daniel Wolfe, which she calls a 'love song'.
- Bayett shares that selling Barking Owl was bittersweet, as she felt like she was losing her 'baby', and grappled with business grief cycle during the transition.
- Cheryl Robinson, a contributor at Forbes, highlighted Bayett's leadership development journey and advice for entrepreneurs who are exiting a company, emphasizing the importance of emotional resilience.
- In 2023, several founders who sold a company experienced a 'business grief cycle', and sought guidance from leadership experts like Kelly Bayett, as they navigated the emotional aftermath.
- According to leadership research, many entrepreneurs go through a 'business grief cycle' when exiting a company, but leadership development programs often prioritize financial and operational aspects over the emotional turmoil associated with selling.