#10: The Founder’s Dilemma with Diane Jones: Insurance tech Industry Leader

In this episode, we dive deep into the world of the Super Unemployable with Diane Jones from InsurTech. We explore the challenges faced by founders who sell their companies and find it difficult to adjust to being employees again, often leaving money on the table. Diane shares her personal journey of selling her family insurance business and her subsequent experiences working for a larger conglomerate.

We discuss the concept of job autonomy and what it means to Diane, as well as her transition from being an entrepreneur to working within a structured organization. Diane opens up about her struggles with micromanagement, the loss of creative control, and how she eventually found her way back to a role that aligns with her values and need for flexibility.

Diane also touches on her current role at a tech firm, her thoughts on future entrepreneurial ventures, and the legacy she hopes to leave for her children.

Whether you're an entrepreneur, a professional seeking autonomy, or someone navigating career transitions, this episode offers valuable perspectives on embracing the Super Unemployable life.

 

Show notes:

Approximately 40% of startup founders leave their companies before completing their buyout or reaching an initial public offering (IPO). This is often due to various reasons, including differences in vision with new owners, personal choices, or simply because the founders are no longer the right fit for the company as it scales under new leadership​(

Knowledge at Wharton

Kruze Consulting

 

Additionally, around 33% of employees, including founders, tend to leave within the first year of a company's acquisition, often due to organizational mismatches or cultural differences with the acquiring company​(

MIT Sloan