Boosting Employee Productivity: Overall’s Co-Founder and CEO Jon Cooper

In this episode we speak with Jon Cooper, Co-Founder and CEO of Overalls, a new kind of employee benefit platform that helps make employees’ lives easier by assisting on things like making financial and insurance decisions, choosing vendors for your home, and handling other personal time-draining tasks.

Jon is the Co-Founder and former CEO of, a pioneer insurtech company that successfully recast digital customer engagement for life insurance.

Three key takeaways from this episode include:

  1. People miscalculate the concept of risk when it comes to entrepreneurship. It can be a lot riskier taking a job and being an employee, rather than building your own business.

2. Entrepreneurs need to have the spirit of “test, learn, experiment.” Always be willing to second guess the assumptions you made going into a project.

3. You don’t need to innovate on every aspect of your business. Innovate on one thing, and be as traditional as possible on everything else. This will allow you to channel all your energy into figuring out the key driver of your business.

Listen on iTunes or Google Podcasts.