#29: Sean Conway - Launching Brands & Being on Shark Tank

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. For more information on Chris Powers and Fort Capital, visit www.fortcapitallp.com. Follow Chris on Twitter! @fortworthchris Connect with The FORT by emailing us at thefortpodcast@gmail.com. 01:18 – Sean’s “Snag Your Ticket Aboard the Magic School Bus” 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

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Here, we uncover the proven strategies, insights, and inspiring stories of today’s greatest leaders in the worlds of business, real estate, entrepreneurship, and investing. Each episode’s mission is to help you to level up your entrepreneurial game by hearing directly from the men and women in the arena. Chris is able to uniquely uncover things not commonly discussed because he is an entrepreneur himself. We not only cover business, but we also cover the personal side of entrepreneurship. The Fort began in 2018 as a way for Chris to publicly explore the fascinating world of entrepreneurship. Since he was a child, he’s been characterized as obsessively curious about the world around him.  The Fort has now been downloaded over 2M times, across more than 50,000 unique listeners. Each week features conversations with entrepreneurs, Founders, CEOs, and Executives from some of the leading companies in America. Past guests have represented companies such as JLL, Hillwood, S2 Capital, Chick Fil A, Morning Brew, Founders Podcast, Tiny Capital, Permanent Equity, Fort Capital, Matthews REIS, Bonobos, and ConvertKit. 🐦 Follow Chris on Twitter: www.twitter.com/FortWorthChris 💡 Follow Chris on LinkedIn: www.linkedin.com/in/chrispowersjr/ 📹 Subscribe to The FORT on YouTube: https://www.youtube.com/@FORTpod