EP10: Lucy Yeomans, Fashion Tech Entrepreneur, Founder and Co-CEO of Drest

To kick off the second season of The Midlife Entrepreneur Podcast, host Jo welcomes Lucy Yeomans, founder and co-CEO of Drest, the innovative fashion styling app that’s transforming the way we interact with luxury fashion through gaming and technology.

They discuss her remarkable career and the innovative fashion styling app that's merging luxury fashion with gamification. From her transformative role as the editor-in-chief at Harper's Bazaar and Net-a-Porter to launching Drest in 2019, Lucy has continually reinvented herself and stayed ahead of industry shifts. 

Lucy shares the lightbulb moments that led to the creation of Drest, the challenges of navigating the tech and gaming worlds, and the importance of personal well-being in entrepreneurial success. The episode also delves into Lucy's approach to building a supportive team, leveraging the fusion of real and virtual experiences, and the ultimate goal of making luxury fashion accessible to everyone.

 00:00 Welcome to the Midlife Entrepreneur Podcast

00:14 Introducing Lucy Yeomans and Drest

00:27 Lucy's Career Journey and Vision

00:42 The Birth of Drest

00:54 Challenges and Collaborations

01:01 The Evolution of Drest

01:33 In-Depth with Lucy Yeomans

01:38 What is Drest?

02:34 The Lightbulb Moments

02:46 The Gaming Inspiration

03:14 From Harper's Bazaar to Net-a-Porter

03:39 The Changing Media Landscape

04:09 The Rise of Gaming

07:52 The Drest Audience

10:24 Building Drest from Scratch

10:39 The Reluctant Entrepreneur

11:58 The Importance of the Right Team

17:16 The Real Virtual Real Concept

21:18 Creating Immersive Experiences

23:08 Personal Challenges and Growth

26:41 Finding Energy and Balance

28:39 The Energy Required to Run a Business

28:56 Gaming and Fashion: Breaking Stereotypes

29:46 The Importance of Physical Activity

31:10 Balancing Work and Personal Life

32:16 Goals and Milestones for the Business

33:59 Three Investments Worth Every Penny

36:37 Two Things I Wish I Had Done Differently

42:26 The Value of Experience and Relationships

46:29 One Person to Thank

50:58 Conclusion and Final Thoughts

Lucy's 3,2,1s:

3 things you've invested in that have been worth every penny:

1. Good People, it's essential. 

2. Time for myself, and investing in my wellbeing. 

3. My child's education, it makes me so happy to know that she's somewhere that's looking after her when I have to work away (they have flexi boarding) and where she's really happy. 

2 things you wish you could have done differently

1. More due diligence in the tech and gaming space beforehand. It slowed us down. 

2. I wish I'd trusted my instinct more. 

1 Person you'd like to thank:

My investor, Graham Edwards, for his excitement and belief in the vision. 

Support the show

Edited and produced by Jo Glynn-Smith 2025.
Recorded at Eight Works Podcast Studios, 1 Dysart Street, London, EC2A 2BX
For bookings: [email protected]

Jo Glynn-Smith is an entrepreneur, professional coach, writer, and speaker from London, she is an expert in career transformation and change.

Instagram @jojoglynnsmith
Contact: [email protected]
www.joglynnsmith.com

MUSIC CREDIT Easy Money by REX BANNER licensed by Artlist.io
PHOTOGRAPHY by JONATHAN GLYNN-SMITH www.jonathanglynnsmith.com