Willo O'Brien's Life & Career Highlights ~ WilloLovesYou.com

Life & Career Highlights

A few of the ‘Heart-Centered Actions’ I’ve taken on my journey…

To see the latest hits, scroll down to the current year.

  • 1996: Moved to San Francisco
  • 1997: Created my first website; mostly scans of my illustrations, photos & updates about my life (blogging before anyone called it blogging)
  • 1996-1999: Worked directly with Spirituality + Creativity Leaders/Authors, such as SARK, Marianne Williamson, Shakti Gawain, Dan Millman, Gabrielle Roth, Deepak Chopra, Hal and Sidra Stone, Geneen Roth, and more
  • 1999: Worked at my first startup, Care2.com, as an E-Card Production Artist
  • 2000: Flash Animation & Design at Spunky Productions (another startup), animating online cartoons for kids
  • 2000-2007: Web/Graphic Design, Flash Design/Animation, and Custom Illustration; serving companies like First Republic Bank, SGI, BrassRing, Fujitsu/Softek, Omneon, Polycom, Daniel Pearl Foundation, DCResource, Mercury Interactive (HP), and many creative small business owners
  • 2003: Officially self-employed (after fatefully getting laid off), though I had been doing freelance design, illustration & animation for a few years prior.
  • 2007: Launched WilloToons ~ where geek meets rock ‘n roll! My product line of designer tees, organic baby clothing, jewelry, cards, totes and more
  • 2007-2010: Touring with my line + speaking, coaching & consulting creative entrepreneurs
  • 2010: Served as Co-Founder/Chief Creative Officer at Storenvy
  • 2001-2011: Completed 10 years(!) of facilitating Bamboozled; a weekly after school program working with rising high-school teen writers and publishing their work online
  • 2011: Launched a new website and premiered WilloToons Connect Creative Sustainability video series
  • 2011: Co-creator in The Ladies Independent Design League (LIDL) a collective of artists, illustrators, writers & photographers meeting weekly in SF
  • 2011/2012: Served as Co-Founder/VP Marketing at Stitch Labs, where we Raised a $1m seed round & Won Best in Show at SXSW!
  • March, 2012: Co-produced SFEmbassy: 100+ friends under one roof for 10 days during SXSW in Austin, Texas
  • March, 2012: Created/Produced CraftMakerCamp SXSW
  • Aug, 2012: Launched RE:CONNECT (3 courses held Sept + Nov, 2012 & Jan, 2013)
  • September, 2012: Nominated & served as an Advisor for ICON8 – The Illustration Conference (2012-2013)
  • Dec, 2012: Launched Feel ALIVE! (2 courses held in Feb + May, 2013)
  • Feb, 2013: Participated in an 8-Day Hendricks Coaching Training Intensive
  • March, 2013: After 13 years as WilloToons, my online moniker evolved to WilloLovesYou
  • May, 2013: Launched SKYDIVING: One-Day Power Sessions
  • June, 2013: Launched Marketing & Social Strategy Packages
  • July, 2013: Co-created YxYY; launched in March, sold out in 48 hours
  • September, 2013: Launched Community Coaching Calls + began hosting Feeding Founders: potluck dinner parties to feed the mind, heart and bellies of hungry founders, artists & entrepreneurs
  • September, 2013: One of my illustrations was published in Outside the Lines: An Artists’ Coloring Book for Giant Imaginations – alongside some of my favorite famous artists: Keith Haring, Shepard Fairey, Kozyndan, and more!
  • October, 2013: Launched Harvest & Thrive
  • Spring 2014: Delivering keynotes & workshops around the world:
  • April, 2014: Said YES to Love & Adventure
  • July, 2014: Yes And Yes Yes (#YxYY), the 400+ person event I co-founded with four girlfriends, holds a second epic ‘YEStival’ in Palm Springs
  • July, 2014: Participated in another 8-Day Hendricks Coaching Training Intensive, and completed my Hendricks Conscious Living & Loving Certification
  • August, 2014: Left San Francisco after 18 years! Working with clients internationally, traveling around the world; speaking, writing & developing retreats/courses in between.
  • October, 2014: Attended DCBKK and held a Gathering of Badass Activators & Conscious Creators in Bangkok, Thailand
  • October, 2014: Attended Evolutionary Playground with Kathlyn Hendricks in Ottawa, Canada
  • November, 2014:  Held a Gathering of Badass Activators & Conscious Creators in Hong Kong
  • February, 2015: One of 20 chosen (out of 160 nominations) to speak at TEDxWanChai Women’s Preview Night.
  • February, 2015: Launched Momentum + Abundant Expansion Group Coaching Program
  • April/May, 2015: Coaching, Co-Creating & MCing #TEDxWanChaiWomen 2015 in Hong Kong
  • July, 2015: Produced our 3rd annual Yes And Yes Yes (#YxYY), the 400+ person event I co-founded with four girlfriends
  • August, 2015: Led two workshops as a guest speaker at Garage Society in Hong Kong
  • October, 2015: Contributed two workshops at Pioneer Nation 2015 in Portland, OR
  • October, 2015: Attended DCBKK again, and held my 2nd annual Gathering of Badass Activators & Conscious Creators in Bangkok, Thailand
  • December, 2015: Created Wake Up With Willo podcast
  • January, 2016: Happy New Year! Launched redesigned website, which you’re on right now. Welcome!
  • February, 2016:
  • July, 2016: Produced our 4th annual Yes And Yes Yes (#YxYY) – you must join us next year! Afterwards, I traveled around the U.S. after, visiting 11 cities in 6 states over 2 months!
  • October 2016: MC’d TEDxWanChai (2nd year in a row) in Hong Kong
  • October, 2016: Attended DCBKK again, and held my 3rd annual Gathering of Badass Activators & Conscious Creators (the biggest & best yet!) in Bangkok, Thailand. Followed by a week in Phuket co-creating the Abundant Circle retreat with 15 other badass online entrepreneurs!
  • December, 2016: Launched Wake Up With Willo daily email inspiration!
  • Happy New Year 2016/2017! Traveled to Taipei, Taiwan for the first time
  • January 2017:
    • Was called to be a clear channel and stopped drinking alcohol, coffee and recreationally taking any mind-altering substances.
    • Started working out with my awesome online personal trainer, Bob!
  • February 2017: Traveled to the US (4 cities in 3 weeks) – Florida to help my Mom move, then LA for Kyle Cease’s Evolving Outloud event, Dallas for Clickfunnels, then to Austin for co-working/co-living week with my Abundance Circle crew!
  • March 2017: Contributed to the Garden Gathering, an incredible weekend of spiritual sisterhood, in HK
  • April 2017: Traveled to Japan for the first time! Osaka & Kyoto
  • May 2017:
  • June 2017: Speaking at Asia Professional Speakers (APSHK) in Hong Kong
  • July 2017:
    • Participated in a Cacao Ceremony (my first of 3 in 2017!)
    • Produced our 5th annual Yes And Yes Yes (#YxYY)! Afterwards, I spent time in SF, LA, Florida & NY.
  • August 2017:
  • October 2017:
    • Contributed to yet another life-changing Garden Gathering weekend in HK. [Post-event Instagram post]
    • Traveled to Bangkok, Thailand for DCBKK and held my 3rd annual Gathering of Badass Activators & Conscious Creators. Afterwards, I spent some QT time with one of my best friends in Koh Phangan.
  • November 2017:
    • Traveled to Bali for the Abundance Circle retreat (year 2) and stayed in Caangu for another week after.
    • On November 28, I decided on my new last name, and announced it on December 3rd!
  • December 2017:
    • Contributed my two signature talks/workshops in the WonderGarden at the Wonderfruit Festival!
    • Spent Christmas & New Years in Chiang Mai, Thailand
  • January 2018: Happy New Year!


I’ve contributed to the following books:

Outside the Lines: An Artists' Coloring Book for Giant Imaginations

Mentioned or quoted in:


What a grand life it’s been so far.
I wonder where it will take me next!