What Happens When Your Startup Fails - And Your Name Is on the Door | Cecily Motley
In this episode, I sit down with Cecily Motley — founder of Harriet and previously the CEO of Motley, a direct-to-consumer jewellery brand that raised millions before collapsing in the wake of Apple’s privacy update.
We talk about the emotional toll of shutting down a business with your name on the door, the lessons she brought into building a venture-scale B2B company, and how she's leading a startup while raising two young children.
This is a conversation about resilience, reinvention, and what happens after your startup fails.
⏱️ CHAPTERS:
00:00 - Intro: Cecily’s story in 20 seconds
01:15 - Why her first startup, Motley, shut down
04:33 - The hidden costs of DTC and the iOS14 death blow
08:10 - The emotional experience of failure as a founder
12:00 - Starting Harriet: a complete pivot to B2B HR tech
15:45 - What Harriet does and why it matters
18:20 - Lessons from DTC applied to B2B SaaS
21:30 - Fundraising post-failure: the mindset shift
25:00 - What makes a defensible company in 2025
28:00 - Building while parenting: realities vs LinkedIn myths
32:40 - Maternity & paternity leave: how founders should lead
36:15 - Advice for founders dealing with failure
39:00 - The importance of self-identity beyond the startup
42:00 - Final reflections and Cecily’s founder advice
#Startups #Founders #B2B #DTC #Harriet #Leadership #TheEverydayFounder #Entrepreneurship
Hosted on Acast. See acast.com/privacy for more information.
