From Family Business to Serial Founder - Looks Like Work, Season 3, Ep 18

Written By Chedva Ludmir
A photo of Ellen Hockley with the overlay text: From Family Business to Serial Founder with Ellen Hockley. Looks Like Work by Chedva Ludmir. Season 1, Episode 18

What do you get when you mix a paper-shredding real estate intern, a pandemic, a newborn, and a sustainable maternity activewear brand? If you’re Ellen Hockley: a wildly resilient serial entrepreneur with the receipts (and emotional battle scars) to prove it.

In this candid conversation, Ellen shares her journey from growing up inside a family business to building (and closing) multiple ventures of her own—including one that launched the same week her son was born. We talk about the heartbreak and healing of business closures, the difference between service and product businesses, and the boundaries she’s now committed to protecting.

If you’ve ever wondered how to move forward after a venture ends—or if you’re currently juggling multiple hats and considering a reset—this one’s for you.

What We Talk About:

  • The entrepreneurial childhood that started with shredding paper

  • Building NYC’s first eco-conscious event planning company

  • The waste problem in events—and how that led to burnout

  • Why she closed one business and opened another… during a pandemic… with a newborn

  • How service and product businesses are completely different beasts

  • What it really takes (emotionally and practically) to close a business

  • The boundaries that now define her consulting life: no credit cards, no employees, meetings only 9–noon

  • The power of knowing what you don’t want to do again

    Ellen’s Powerful Question:

    “Why are you driven to do this?”
    If you can’t answer that, Ellen says it’s time to dig deeper.

    Key Lessons:

    • Product ≠ Service: They require entirely different skill sets

    • Get nosy with your bookkeeper: Ask about platform-specific experience (Shopify is not the same as Squarespace)

    • Closure takes time: Emotionally and logistically, closing a business is a marathon

    • Boundaries are part of the business model: Credit cards, employees, and time blocks aren’t for everyone

    • Build from your scars: Your past ventures shape your future boundaries

    • There’s no shame in stepping back: And sometimes that step back is exactly what propels you forward

 

"My husband was like, 'You need to find a hobby.' I'm pretty sure he meant sourdough, not start a new business"

 
Chedva Ludmir
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Building a Business That Supports Your Life - Looks Like Work, Season 3, Ep 19
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Tech Cycles, Masculine BS, Career Choices - Looks Like Work, Season 3, Ep 17