Lindsay Friedman built two tech companies, walked away from the second after a patent asset sale, and swore she'd never build again. Then she became her grandmother's family caregiver — and the thing she said she'd never do again became the thing she couldn't not do.

In this episode, Lindsay walks through the roller coaster of her first startup (a total failure), the patent sale that quietly ended her second, and the night her grandmother fell and broke her femur — the moment that pulled her back into building, this time for reasons that had nothing to do with return on investment. She and KiKi talk about what it's like to still be asking "who am I right now?" years into a pivot, why self-doubt kept her honest instead of stuck, and how being a self-described "control freak" collided with running a business built on things she couldn't control.

Lindsay is now the founder of Care Bloom and LT Care Nav, and hosts the Caregivers Compass podcast. This one's for anyone whose "never again" turned out to be less final than it sounded.

HIGHLIGHTS

• 01:33 — "Everything" — the roller coaster that made her say never again
• 02:28 — The patent sale that quietly closed the door on company #2
• 09:00 — She ghostwrote her grandmother's Holocaust survival story at 19 — years before it would matter
• 12:50 — The fall that turned "never again" into a new company
• 25:33 — "I still look around and go, who am I right now?"
• 32:39 — Why self-doubt is what keeps her on the right path, not off it

• LT Care Nav podcast (Caregivers Compass) + book giveaway on care planning: ltcarenav.com/podcast

Things Go Sideways with KiKi L'Italien is a space for honest conversations about disruption, identity shifts, and reinvention — no tidy bows, just real stories about staying oriented when what you thought was certain collapses.

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