How to Reinvent Yourself & Start Over with Jenna Lyons, Fashion Icon & Founder of LoveSeen

Dubbed by the New York Times as ‘the woman who dresses America’, Jenna Lyons, is a fashion icon and the co-founder/CEO of the beauty brand, LoveSeen. 

Having kicked off her career as an intern at Donna Karan, Jenna went on to join the design team at J.Crew, eventually becoming its President. She is recognized as the main driver behind its incredible rise to success, and is a regular feature in print and online media, including having been recognized as one of Time Magazine’s 100 most influential people.

After 27 years at J.Crew, Jenna was finally ready to start her own empire. She launched her company LoveSeen, a direct-to-consumer beauty brand that is reinventing fake lashes, which was largely inspired by her genetic condition that impacts her lash growth. And she was most recently, the Executive Director and main star of her reality competition show, Stylish with Jenna Lyons on HBO Max.  

On today’s episode, you’ll hear how Jenna’s challenging childhood experiences shaped who she is and how she experiences the world today, including her attitude to finances and her love for fashion. She tells us what it was like to live in New York in the 1980s and discover a new standard of beauty which was largely different from the beach town she grew up in. Jenna reveals what it was like to work with Mickey Drexler, former CEO and Chairman of J.Crew Group, the skills she needed to develop to manage the people she worked with, and what it was like to enter the public eye. 

You’ll also hear why Jenna decided to reinvent herself later in her career, how she overcame the most difficult transition in her life when she left J.Crew, what she loves about working in beauty when compared with fashion, and the biggest lessons she’s learned on running her entrepreneurial ventures.

In this episode, we’ll talk to Jenna about: 

* The impact of Jenna’s mother’s attitude towards financial independence on how she approaches money today. [3:10]

* How knowing you can take care of yourself affects fear and trust in relationships. [4:30]

* The poignant experience of interest in her work and style when she began to make clothes after growing up feeling unattractive. [5:20]

* What it was like to grow up with a genetic disorder and how sewing a skirt led to a popular girl in school asking Jenna to make one for her too. [6:40]

* What it was like to live in New York in the late 1980s. [9:04]

* How Jenna didn’t meet the standard of beauty in the beach town she grew up in. [10:30]

* The discovery of Antonio Lopez as a pivotal point in discovering her own beauty. [11:38]

* How she came to intern at Donna Karan and study at Parsons University in the 90s. [12:35]

* The listing that led Jenna to take a job at J.Crew without asking about the salary. [13:35]

* Why she was so unhappy at the start of her career at J.Crew. [15:48]

* The dramatic change at J.Crew that completely turned things around [17:20]

* What it was like working with Mickey Drexler (CEO of JCrew); his alchemy skills, attunement, and insight. [18:18]

* Jenna’s lifelong drive to make beautiful things that she could be proud of. [18:43]

* How she needed to develop skills to manage people she worked with. [21:20]

* What she learned from Mickey’s desire to hear from everyone. [22:18]

* Entering the public eye starting with Domino Magazine, then Vogue with Annie Leibovitz, and the internal struggle Jenna experienced. [25:01]

* Find out how Jenna navigated different transition periods in her life. [28:29]

* The nine-month period of silence that helped her regroup and see what’s important. [29:10]

* Being approached to do television and what it was like to shoot the reality show. [31:43]

* What Jenna loves about the beauty scene: she doesn’t have to think about size. [36:05]

* How Jenna realized t