Episode 109
June 7, 2022

From Spinout to Standalone

with Maggie Winter, Co-Founder and CEO of AYR

About this episode

Maggie Winter joins the show today to chat with Lee about her journey to becoming the Co-Founder and CEO of AYR, otherwise known as All Year Round. Originally born as a sister company to Bonobos in 2014, AYR spun out a year later into its own standalone company. AYR is a women's wear brand that designs seasonless and ageless apparel for everyday life. In this episode, Maggie talks about the separation process from Bonobos and what it was like to take the business into her own hands, the challenges she faced running out of cash, and how she had to adjust her mindset from employee to business owner.

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In This Episode You’ll Hear About:

  • (3:40) Her life growing up in Hershey, Pennsylvania, and what it was like working at the Hershey Chocolate Factory 
  • (11:30) How connecting the dots from things she's interested in, to things she has to do but lacks interest in has helped her in her CEO journey
  • (12:20) What her time working at J.Crew was like, and what she learned directly from the CEO
  • (19:54) How she got connected to the Founder of Bonobos and got to pitch him her idea for AYR
  • (28:52) What she learned in launching a brand, and the advice she has for others 
  • (38:47) Why she chose to take AYR into retail, knowing that it would be a great place for customers to connect with the brand 
  • (40:10) Some of the biggest challenges she faced in running out of cash, and how she had to adjust her mindset from employee to business owner.
  • (57:42) The advice she has for those aspiring to become entrepreneurs, that you should talk yourself out of it until you no longer can

To Find Out More:



“You learn things as you have to learn them.”

“You can always connect the dots backward, but you can never get them forward.”

“You want to interact with customers directly with the product as often as you can.”

“Adjusting from the mindset of being an employee to being a business owner took time, and getting comfortable with conflict and confrontation and making changes that weren't going to make everybody happy took some time.”

“Don't do things the way that you think they should be done, or the way that you're told they should be done. You have to do what's right for you. And you have to figure out how to be yourself in the world.”

“When you're a CEO and you're responsible for the health and the performance of the company and the people in it, you can change everything. It is all in your control.”

“Everything that we make has to be really comfortable, it has to be really versatile, and we will go anywhere in the world that we can source the best version of a product.”

“You can do anything, but you have to do it.”

“You have to hire people that you trust and respect so that you can manage them with trust and respect.”

“There are so many different ways to be involved in the excitement, learning, growth, and the journey of a startup without being the founder or the CEO. So I would try to talk yourself out of it, talk to friends who you trust and respect, and get them to try to talk you out of it. And if at the end of the day, if you can’t be talked out of it, good luck, you gotta do it.”

Read the transcript

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