Jay Steinfeld | Experimenting and Enjoying the Ride

"You really never know when you set out to do anything, if it's going to work. If you do know, then you're not experimenting enough."

This week's guest is Jay Steinfeld, author of Lead from the Core and founder of Blinds.com, which he sold to Home Depot in 2014. Steinfeld remained the company's CEO until he left in 2020 to not retire but, as he calls it, "rewire." He teaches business and entrepreneurship at Rice University, serves on multiple boards, and is active in charitable organizations.

Jay's predominant approach to life and to business is to learn as much as possible, with the understanding that you're never going to know it all. He believes in experimentation, and in taking small steps to try something new to figure out if it's something he wants to build on. The loss of two important people in his life—his mother when he was a teenager and his wife after 25 years of marriage, both to cancer in their late 40s—also motivated him to learn and come to a better understanding of how he wanted to live his life. Two texts he cites as influential are Man's Search for Meaning by Victor Frankel and The Happiness Hypothesis by Jonathan Haidt.

Jay explains how being value-led drove him in building his company. One of these values is experimenting without fear of failure. By articulating and modeling the core values of the company, he was able to hire people who would not be afraid to speak up and experiment. He was also able to guide his business as it was sold to Home Depot, making sure that the people who had helped him build his business were recognized, appreciated, and well compensated for all they did. Honesty is another value Jay discusses in this episode, where he advises CEOs to "not be chickenshit" but to be the one who tells people what they need to know.

Another value Jay discusses is to "enjoy the ride." Having challenges and facing the unknown have been motivating for him, and he loves working with others to come up with new ideas and solutions. He believes his greatest achievement is assembling teams of people who succeeded at doing things he could never have done alone.

In this episode of Leading with Genuine Care, you’ll also learn:

How the loss of Jay Steinfeld's mother and wife affected how sees the world
How he approaches social media
How he went about planning for his "rewirement" and the one person he wanted to meet
When it might make sense to give up
How to model and send the message to employees that experimentation is valued
What you need to do if an employee is not performing up to expectations
What to do before selling a business