About Outlines Venture Group

Anne Kennedy and Gillian Muessig are field-tested entrepreneurs and investors, startup mentors, brand whisperers . . . and cheerleaders, too. Keynote speakers worldwide, and fearless and enthusiastic travelers, they joined forces to help online companies launch, grow pivot and thrive to build better ways to live and work together. With more than 80 years experience between them, Gillian in software and Anne in services, they formed Outlines Venture Group in 2013 to turn around and use the know-how they garnered – often the hard way -- to give other entrepreneurs a hand up and smooth the ride for CEO’s running growing companies.

Together, Anne and Gillian invested in and mentored early stage Internet companies in return for equity and board seats, in a limited portfolio of carefully screened start ups which show promise to scale.  In 10 years they saw four exits between them, on invested capital of $4.8 million and generated revenue of $475 Million. 

In 2018 they launched a new fund, The Sybilla Masters Fund, women-led venture capital to invest in tech startups led by women, and tap into a $4.4 trillion business opportunity. Their superpower is attracting well-versed partners to their venture, all experienced entrepreneurs and investors. Outlines Venture Group serves as Managing Directors for the new fund, trademarked 'Mastersfund'.

To continue to share what they have learned with emerging businesses, Gillian and Anne speak all over the world to conferences, universities and business associations about funding women-led women start ups, digital marketing, leadership and organization development.

On CEO Coach Podcast on Webmasterradio.fm  Anne & Gillian chat chief to chief on issues facing entrepreneurs, with frequent guests who have founded, raised and often sold companies themselves.

Outlines Venture Group values:

  • Simplicity
  • Clarity
  • Accountability
  • Liquidity
  • Execution


Gillian Muessig, CEO & Co-founder

Anne F. Kennedy, President & Co-founder