When That Big Break Just Might Break You

When That Big Break Just Might Break You

From 21 Hats Podcast by 21 Hats

May 5, 2026 · 43 min · Episode 292

About this episode

Liz Picarazzi shares her experience of a high-profile failure that ultimately transformed her business, while Lena McGuire discusses the challenges of upgrading business systems.

Every business owner looks forward to that big break—the moment that you land a big client or a major retailer, or do something that puts you on a national stage. But those opportunities don’t just reward you. They can also expose you—especially if you have to take on debt or ramp up production or do things you haven’t done before. Four years ago, when Liz Picarazzi won a high-profile installation for her trash enclosures in Times Square, it was exactly that kind of opportunity. Her enclosures were put to the test in as public and as challenging an environment as she could imagine. And, by any reasonable measure, they failed. In pursuing that opportunity, Liz took a risk that led to what she calls the worst day of her professional life. It also turned out to be, as she tells Lena McGuire, the best thing that could have happened to her business. That moment forced changes she might never have made otherwise, pushing her to innovate faster and sending her business on a very different trajectory. Meanwhile, Lena is dealing with a quieter version of the same problem: what it really takes to move your business forward. She knows her systems need an upgrade. She’s bought the software…

People in this episode

Host: Lena McGuire

Guest: Liz Picarazzi

Topics covered

  • business challenges
  • innovation
  • risk management
  • entrepreneurship
  • operational upgrades

Keywords

  • big break
  • business failure
  • entrepreneurship
  • risk
  • innovation
  • operational efficiency

Mentioned in this episode

Places: Times Square

More episodes of 21 Hats Podcast

Explore listener stats, chart rankings, contacts and more on the 21 Hats Podcast podcast page.