48. She Quit Law Twice, Then Invented a Water Scooter | B Student | Lindsay Kiley

Lindsay Kiley did it twice. She stepped away from law to raise her kids, went back to try again as a lawyer, and still something didn't feel right. It wasn't until she invented the Swelly water scooter that she finally built something that felt in alignment.

In this episode, host Ashley Billings talks with Lindsay about what those in-between years looked like: the failed ventures, the slow realization that returning to law wasn't the answer, and what it takes to keep going when nothing is working.

The overnight success part? It's the smallest part of the story.

We get into:

Leaving law, returning to it, and leaving againThe Campable startup experiment and what it taught herEntrepreneurship while raising kids, the parts nobody posts aboutHow Swelly went from a garage idea to retail shelvesWhat she'd tell anyone who feels like they've missed their windowIf you're mid-pivot, stuck, or rebuilding, Lindsay's been there. More than once.

This episode is part of B Student: Summer School, a limited series featuring entrepreneurs and professionals who have gone through Winter Park Chamber of Commerce leadership and talent development programming

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Time Stamps:

00:00 Introduction + Meet Lindsay Kiley

02:45 Leaving Law + Entering the Unknown

05:30 Trying Again (And Why It Still Didn’t Fit)

08:10 Failed Paths: Campable + In-House Role