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

Episode Summary

Conway, with a background marked by innovative ventures and strategic decision-making, delved into various facets of entrepreneurship, startup financing, and the importance of effective communication and self-awareness. His narratives, rich in personal anecdotes and practical insights, provided listeners with invaluable lessons applicable not just in business, but also in personal development and networking.

Conway initiated the conversation emphasizing the significance of self-awareness, urging individuals to reflect on their unique strengths and weaknesses. He advocated for a profound understanding of one’s capabilities, highlighting that such awareness is crucial for excelling in the competitive realms of real estate and entrepreneurship. Sharing personal stories, Conway underscored the transformative power of embracing one’s unique skills, while also acknowledging and working on areas of improvement.

The discussion seamlessly transitioned to Conway’s experience on Shark Tank, providing a behind-the-scenes glimpse into the show and its impact on his entrepreneurial journey. Conway recounted the spontaneity of his participation, emphasizing how the exposure and opportunities garnered from the show played a pivotal role in shaping his career. He reflected on the evolution of Shark Tank over the years, providing a comparative analysis of his time on the show and its current state, highlighting the increased opportunities and exposure it now offers to entrepreneurs.

Delving deeper into startup financing and strategic decision-making, Conway shared a critical moment in his journey, detailing a significant funding opportunity and the intricacies involved in negotiating term sheets. He underscored the importance of strategic leverage, transparency, and the ability to make informed decisions under pressure. Conway’s narrative shed light on the complex world of startup financing, emphasizing the necessity of negotiation skills, foresight, and a deep understanding of the startup ecosystem.

The conversation further explored the realm of company equity, particularly in the context of sales or acquisitions. Conway imparted valuable lessons from his past experiences, stressing the importance of equitable distribution among employees and clear communication regarding financial outcomes. He highlighted the responsibilities of leadership in ensuring transparency, fairness, and the fostering of a positive company culture, especially during pivotal moments of transition.

In the concluding part of the podcast, Conway shared his approach to fostering deeper, more meaningful interactions, both in personal and professional settings. He emphasized the value of intentional dialogue, encouraging listeners to engage in conversations that transcend superficial exchanges and foster genuine connections.

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