Wiley Cerilli is a serial entrepreneur and founder of companies like Seamless Web, SinglePlatform, and Good Uncle. He was previously the VP and General Manager of Constant Contact after they acquired his company SinglePlatform for $100 million. Throughout his career, Cerilli has experienced immense personal and professional growth, including overcoming the tragic loss of his father at a young age.
The interview covers Cerilli's inspirational journey, from losing his father while in high school and becoming "CEO" of his family, to the lessons he learned from successful exits at Seamless Web and SinglePlatform. He provides tactical advice for entrepreneurs on topics like fundraising, hiring, sales, product development, and maintaining work-life balance through difficult times. Cerilli stresses the importance of community and resilience when dealing with trauma and chaos. He shares vulnerable stories and actionable frameworks like "Test, Tune, Scale" that provide invaluable insights for young founders. This emotional yet practical interview exemplifies how entrepreneurs can draw strength from hardship, build empathy and vision, and manifest success through perseverance.


OUTLINE:


(00:00:00) Intro
(00:00:31) Introduction to Wiley Cerilli's background and entrepreneurial journey
(00:02:39) Losing his father to cancer at a young age and the impact on his family
(00:05:50) Overcoming adversity and tragedy through entrepreneurship
(00:07:15) Getting his start in startups at Seamless Web
(00:10:00) Starting Single Platform and lessons on fundraising
(00:14:02) Founding ghost kitchen startup Good Uncle
(00:17:02) Entrepreneurial mindset and creating urgency
(00:22:39) Exiting Single Platform to Constant Contact
(00:28:27) Research on childhood loss and achievement
(00:31:36) Starting the non-profit Experience Camps
(00:35:18) Balancing urgency and breaking people in business
(00:43:22) Being ahead of the market with Good Uncle
(00:52:14) Building sales teams and call centers
(01:00:38) Emotions after a big exit
(01:06:14) Grieving as an entrepreneur
(01:10:00) Skipping steps when scaling companies
(01:15:11) Selling Good Uncle to Aramark
(01:17:02) Founding House Account and digitizing home services

 
EPISODE LINKS:


Wiley’s LinkedIn: https://www.linkedin.com/in/wileycerilli/
Wiley’s Twitter: https://twitter.com/wileycerilli?lang=en
Seamless Web: https://www.seamless.com/
SinglePlatform: https://my2.singleplatform.com
Good Uncle: https://www.gooduncle.com/
Experience Camps: https://experiencecamps.org/
David and Goliath Book: https://www.amazon.com/David-Goliath-Underdogs-Misfits-Battling/dp/0316204374
Thinking Fast and Slow Book: https://www.amazon.com/Thinking-Fast-and-Slow-audiobook/dp/B005Z9GAJG
The Perfect Storm Movie: https://www.imdb.com/title/tt0177971/

PODCAST INFO:


Podcast website: https://forwardobsessed.com/
Apple Podcasts: https://podcasts.apple.com/us/podcast/forward-obsessed/id1615760781
Spotify: https://open.spotify.com/show/2TrkOZ7xL7WSlzc2mrwXuC?si=aa5e7790aca64e05
YouTube Full Episodes: https://youtube.com/playlist?list=PL-ldUUGxQZ5b9WPqVXz_qlfXgK3hHPs4z
YouTube Clips: https://youtube.com/playlist?list=PL-ldUUGxQZ5Yt0LiPml0y6pNUSrqHzWql

 
SUPPORT & CONNECT:


Digital Surgeons Website: https://digitalsurgeons.com
TikTok: https://www.tiktok.com/@digitalsurgeons
Instagram: https://www.instagram.com/digitalsurgeons
LinkedIn: https://www.linkedin.com/company/210497/

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