Uncovering the World of VC and Angel Funding

Angel Investment

Finding and securing funding can be one of the hardest and most stressful tasks for a startup and rapidly scaling business. Knowing how to identify, locate and apply for financing is key to moving a business from concept to reality. Our investors will speak about the angel and VC model of financing, strategies on what gets their attention, and tips on what turn them away. The secrets from behind the scenes of the world of investors will be explored through short keynotes followed by an interactive panel discussion with Q&A from the audience.


Jess Joss, BA'97
Executive Director, Board Member and Angel Investor, York Angel Investors

With over 20 years of business expertise and almost a decade of investing experience, Jess Joss is Executive Director of York Angel Investors Inc. (YAI), co-founder of Insiteful Solutions and partner in Spyder Capital Corp.

Jess’s passion for entrepreneurship began shortly after university when she founded a web development firm which continues to thrive today. Jess grew Insiteful Solutions, scaling it to an integrated online marketing firm, eventually adding partners. In 2011, with a structure in place, devoting her time to Insiteful Solutions pivoted to investing in the future of start-ups. With extensive business experience, as well as Board and volunteer management expertise, Jess became the Executive Director of YAI in 2014, following many years as an active angel investor with the group.

Leveraging her entrepreneurial, business, and marketing acumen, Jess has worked with the YAI team to grow membership by over 450%, as well as increase deal flow, the number of deals completed and amount invested. Today, YAI now has the largest membership in Ontario and second largest in Canada. Jess was recently appointed to the National Angel Capital Organisation’s Board, as Marketing Chair and is NACO World Angel Investment Summit (Conference) Chair.

In her spare time, Jess enjoys spending time with her family. She is also an active community volunteer, whose roles have included President of the Queen’s University Alumni Association and two terms as President of the local Rotary Club. Her hobbies include photography, Pilates, paddle boarding, cooking, and cottaging.

Menashe Kestenbaumbe
CEO & Founder, Enthusiast Gaming

Menashe began his career in video games when he was 13, writing for IGN, a large gaming media site, where he eventually became a community leader. After studying and subsequently lecturing in the Institute of Advanced Talmudic Law in Jerusalem for eight years, Menashe returned to his passion for the video game industry and launched his first gaming blog, “Nintendo Enthusiast”, in 2011. In 2014, he returned to Toronto and incorporated Enthusiast. He has personally owned and operated gaming websites to a readership of over 2 million gamers, has led Enthusiast and grown a writing and community staff team of over 84 people. An Entrepreneur and trusted leader in the video game sector, Menashe has led Enthusiast Gaming from its roots as a little startup in a basement in 2015, through a 10x revenue growth 2016-2017, and most recently a 2018 public company listing on the Toronto Stock Exchange with over $10M in annual revenue and a $50M market cap.

Shayn Diamond, MBA’11, JD (Law)’12
Partner, Whitecap Venture Partners

Shayn is a Partner at Whitecap Venture Partners. Shayn works closely with Qvella, Affinio, Classcraft Studios, and Bold Commerce. Shayn is active in the community, including involvement with Sunnybrook Health Sciences Centre and Sick Kids Hospital.

Prior to joining Whitecap, Shayn was a lawyer at Wildeboer Dellelce LLP. At Wildeboer, Shayn practiced primarily in the areas of securities, corporate finance and commercial real estate with a focus on corporate finance and mergers & acquisitions.

Shayn holds a JD and an MBA from Smith School of Business, Queen’s University. He also holds a B.A. in Philosophy from the University of Western Ontario.


May 13, 2019
06:00 PM - 09:00 PM
200 Front Street W
30th Floor


Registration is closed

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Jess Joss BA'97
Executive Director, Board Member and Angel Investor, York Angel Investors

Shayn Diamond, MBA'11, JD (Law)'12
Partner, Whitecap Venture Partners

Menashe Kestenbaum
CEO & Founder, Enthusiast Gaming