Crafting Style Experiences with Anya Cheng

Experience by Design

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Recently my life of skirting the law caught up to me…..twice. My attempt to thumb my nose at the Deep State was met with the power of law enforcement when I was pulled over at two different times for the transgression of an expired inspection sticker for my car. It is now the month of June and my sticker expired in May…..of 2024. So that means for you keeping score at home that the last time my car was inspected was May 2023.

Both times that I was pulled over in the span of one week, I was asked the same question: why did you let your sticker expire for so long?

Fair question. But to provide an honest answer I would have to dig into why I have any of the unhelpful patterns in my life. At first I just forgot to get it done. Then I got ashamed I didn’t get it done. Then that shame just became a larger pattern of my life which came to define me. Then to get it fixed would be to wonder who would I be without that expired sticker?

After the second time getting pulled over, I promised the officers that I would right away get it fixed. And true to my word, I did. $35 and 15 minutes later, I now have a 2026 expiration sticker. I have to say that I feel oddly relieved.

I also have to say that in both cases the officers were extraordinarily nice, and included one trainee who did a fine job with approaching my car.

I think the moral of the story here is that we sometimes need help from others to get over the old patterns of our lives and to create new patterns that allow us to move on in healthier and better directions.

My guest today on Experience by Design also has built a business to help people create a new version of themselves. Anya Cheng is the Founder and CEO of Taelor, a leading men’s clothing subscription service that provides personal styling and curated rentals for their customers. But that’s not all. They help their customers through a combination of expert stylists and AI. So when we are looking for example of AI being used for good, here you go. When you look amazing in your new outfit and people ask, Where did you get that? You can say, AI.

It’s not surprising that AI can help in this way because any time I’ve seen an AI character in a movie, they’ve dressed well and looked cool.

Beyond Taelor, Anya is a Girls in Tech 40 Under 40 honoree, having led eCommerce and digital innovation teams at Meta, eBay, Target, and McDonald’s.

We talk about a range of topics, such as helping customers make changes in their lives, trends in fashion across different cultures, quiet luxury versus conspicuous consumption, long-term launches versus short-term disruption.

We also talk about her career in journalism, and how telling the stories of others and knowing how to stand around both served her well in her career.

Experience effortless style with rental and personal styling services any time of the year with the following special for ExD listeners:

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