Mike Dendy on M&A mastery: how entrepreneurs can navigate exits and private equity

On this week’s episode of The Roadmap, we are thrilled to have Mike Dendy, the co-founder and CEO of Caryn Health, join us. With a wealth of experience in the healthcare industry and a track record of successfully navigating the M&A landscape, Mike shares his journey of building and exiting businesses, offering invaluable advice for entrepreneurs looking to scale and eventually sell their companies. From the intricacies of private equity to the importance of strategic planning, this conversation is packed with insights that every business owner should hear.

Key Takeaways

1. Mike Dendy discusses the origin of Caryn Health, which was born out of a need to address the healthcare needs of small businesses and the gig economy. The company’s foundation was built on the innovative idea of creating software that could modernize healthcare operations, which led to a year-long pause in operations to develop the necessary technology.

2. Unlike his previous ventures, Dendy shares that Karen Health was the first business he built with a clear exit strategy in mind. This approach allowed for meticulous planning and structured growth, eventually attracting significant interest from private equity firms.

3. Dendy reflects on his first business exit, where he felt he could have negotiated a better deal. This experience taught him valuable lessons about the importance of having strong advisory support during negotiations and understanding the true value of what he was selling.

4. The interview delves into the often complicated relationship between entrepreneurs and private equity firms. Dendy highlights the differences in mindset: Private equity focuses on short-term financial gains, while entrepreneurs may prioritize long-term business sustainability and employee well-being.

5. Dendy explains the concept of “leaving money on the table” in an M&A deal, where entrepreneurs might retain a percentage of equity post-sale, hoping to benefit from future growth. He shares his experiences of balancing this with the understanding that private equity may not always align with the entrepreneur’s vision.

"I've learned that private equity firms are masters at financial engineering, but as an entrepreneur, I was more focused on the longevity of my business, sometimes taking two steps back to ensure its future. It's a delicate balance, but understanding that difference is crucial when considering an exit." - Mike Dendy.