Our special guest for this Member Brief was Mat Ellis – Founder & CEO of Sixty AI and Managing Partner of Sunny Ventures. Although Mat is best known for founding Cloudability, which was acquired by Apptio in 2019, we know him as one of our most generous and stalwart supporters in the Portland ecosystem.

As a former Brit living in Portland, OR, naturally Mat boasts an extensive tea collection. He also knows his way around a poker table; watch out if he sits at your table. In this member brief we’re going to catch up with Mat and pick his brain on topics across the wide spectrum of his experience… as a serial, exited founder, as an investor, and as a startup junkie dedicated to supporting the Portland ecosystem.

Sixty AI helps you take back your time. They use AI and machine learning to solve one big problem of modern technology: its constant demands for more and more of your attention.

Bob Crimmins is a seasoned entrepreneur with 25 years of experience as a startup founder, mentor, advisor, writer, speaker, and organizer. He is the founder and general partner of Startup Haven Ventures, a pre-seed venture fund and accelerator that has grown into the largest founder and investor community of its kind, with over 2,500 members across the U.S.

Bob’s entrepreneurial journey began early in life, working in his family’s business at age nine and launching various ventures throughout his youth, from selling Blow Pops in middle school to founding a consulting firm in college. Bob’s career in technology startups began as a software engineer, writing his first program on punch cards in high school, at a time when when it was neither cool nor lucrative to be a teenaged programmer.

Over the years, Bob has founded/co-founded four venture-backed startups and held leadership roles as CEO, CTO, CMO, and CRO. He has also been a highly-rated mentor for numerous accelerator programs, guiding over 300 startups and serving on the advisory boards of more than 20 companies. Bob’s diverse experiences and deep commitment to the startup ecosystem have made him a respected figure in the entrepreneurial community.