The FORT Podcast: Sean Conway

Sean Conway is an avid traveler and former CEO of Pillow, a company he co-founded. Pillow partners with Multifamily property owners to provide short-term rentals as an amenity to their residents. Pillow’s turn key software makes hosting easy, profitable, and compliant. Sean held leadership positions from conception to $17.5 million in funding and a successful acquisition by the Expedia Group in September 2018. Prior to Pillow, Sean was the Co-Founder of Notehall, an online class and study notes provider, which was acquired by Chegg in 2011. For Sean’s ingenuity, he was named one of the “Top 25 Entrepreneurs Under 25″ by Business Week in 2009. Sean is an active angel investor and enjoys mentoring startups/programs, such as BUILD.

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01:18 – Sean’s Recent Blog Post
05:30 – Sean and Chris’ Experience Traveling to Other Countries
11:11 – How does the meaning of entrepreneurship change as you start more companies?
12:44 – Sean’s Experience on Shark Tank
17:07 – Notehall
19:00 – What is it like to exit a business in the technology industry?
30:28 – Do you fall out of love with your business when the opportunity to sell becomes a reality?
33:35 – How was your experience selling Pillow and Notehall? How did you tell employees?
42:05 – Do you want to stay in a similar industry, or are you moving on?
44:00 – Meditation and Journaling
45:49 – Expedia & Sean’s Goal to Not Start a Company for 3+ Years
46:23 – Employee Turnover When You Sell a Company
48:18 – Favorite Interview Questions & Using Executive Recruiters
56:07 – Growth Hacking a Network