Looks Like Work

From Family Business to Serial Founder (with Ellen Hockley)

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 In this open and vulnerable conversation, Ellen Hockley—three-time founder and consultant—shares her winding path from shredding paper at her family's real estate business to building (and closing) multiple ventures of her own. After launching one of the first eco-friendly event planning companies in NYC, Ellen navigated the collapse of the events industry during COVID while simultaneously starting a sustainable maternity activewear brand—the same week her first son was born. The conversation explores the emotional weight of closing a business, the lessons learned from "fucking up" your books, and why managing 100 employees was never going to be her path. Ellen reveals how each venture taught her something crucial about herself, from discovering she doesn't actually like retail to learning that scarcity creates urgency in time management.

Key Topics:

  • Growing up in entrepreneurship: from paper shredder to potential successor
  • Building one of NYC's first sustainable event planning companies
  • The waste crisis in events: when raising money for education means dumping platters of food
  • Pandemic pivot: closing events while opening an apparel business (with a newborn)
  • The reality of overlapping businesses during COVID lockdowns
  • Why product-based businesses are nothing like service businesses
  • Why closing a business takes over a year (emotionally and practically)
  • Building boundaries: no credit cards, no employees, meetings only 9-noon

    • Notable Quotes:

    • "I had two babies in the same week"—on starting Evergreen the week her son was born
    • "My husband was like, 'You need to find a hobby.' I'm pretty sure he meant sourdough, not start a new business"
    • "I joke that I now have an MBA, both from what I learned, but also what I spent"
    • "To somebody on a podcast recently, they said 'You're just sowing your seeds.' And I was like, that is exactly what I'm doing"
    • "Something there failed, but it wasn't a failure. There were many successes"
    • "The fact that you can deal with things and that you're brave and strong doesn't mean you want to put yourself in a position to deal with it"

      •  

      Ellen's Powerful Question: "Why are you driven to do this?"—A question she believes every entrepreneur must be able to answer, or it's time for a deeper conversation about why you're here.

      Resources Mentioned:

      • Ellen Hockley Consulting - Current venture
      • Chedva on Ellen and Kat’s podcast - Good Ideas + Bad Decisions
      • Ellen’s Linkedin
      • SNL pandemic psychic skit

        •  

        Key Lessons:

        • Service-based vs. product-based businesses require completely different skills
        • Interview your bookkeeper about their specific experience (Shopify ≠ service business)
        • Build from your scars: know what risks you will and won't take again
        • Closing a business is both physical and emotional work
        • Every failed venture teaches you what kind of founder you want to be next
          • ...more
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          Looks Like WorkBy Chedva Ludmir