Leah Solivan, the visionary founder of Taskrabbit, dives deep into her entrepreneurial journey and the gig economy. She shares the quirky inspiration behind Taskrabbit, sparked by a snowy night and a dog food emergency. Leah discusses her transition from startup founder to venture capitalist, highlighting the vital questions entrepreneurs should pose to investors. Her insights on scaling challenges and the significance of mentorship shine a light on her path. Plus, she hints at her upcoming podcast, Breaking Precedent!

One snowy night in Boston, Leah Solivan ran out of dog food for her 100-pound yellow lab. She wondered: shouldn’t I be able to resupply Kobe without going to the store? That was the origin of TaskRabbit, an online errand service that matches users with “taskers” to do deliveries and other chores. When Leah left her IBM job to start coding the service, the peer-to-peer economy was still in its infancy. But she saw that three important developments—mobile, location services, and social media—were about to converge. She recruited errand-runners from Craigslist, and took an expensive gamble on a 15-minute meeting with Tim Ferriss to get advice and investors. After some management hiccups and a difficult rebranding, TaskRabbit sold to IKEA in 2017. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Leah Solivan, founder of Taskrabbit, shares her entrepreneurial wisdom while advising tech founders on their unique challenges. She discusses how Kate can make her digital greeting cards stand out, and provides insights for Shahn on user acquisition for his couples coaching app. Leah also explores strategies for Allen to achieve product-market fit for his children's music education platform. Emphasizing community support and adaptability, she offers actionable tips that every entrepreneur can benefit from.