Plenty of Ups and Downs: Riding the Rollercoaster of a Startup

After more than 15 years as an executive at Meta, eBay, and Target, Anya Cheng set out to launch her own venture, Taelor. Her company uses artificial intelligence and personalized styling to rent clothing to men who dislike shopping, but need to look put-together for professional and social occasions.

As she candidly shares this week, her two-year-old company has encountered a full buffet of challenges — from limited resources, both financial and human, to the steep personal transition of relying entirely on her own judgment.

Drawing from her successes and missteps, Anya offers ten actionable recommendations that every new and most established businesses should heed. Be sure to have a tablet or pen available to take notes.

Above all else, Anya’s journey underscores the grit and adaptability required to build and maintain a new business in today’s startup landscape.

Monday Morning Radio is hosted by the father-son duo of Dean and Maxwell Rotbart.

Photo: Anya Cheng, Taelor
Posted: May 19, 2025
Monday Morning Run Time: 47:07
Episode: 13.46

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