Ben Yoskovitz

Founding Partner at Highline Beta | Author of FocusedChaos.co

πŸ“ Toronto, Ontario, CanadaπŸ”„ Updated October 2026πŸ’Ό 6 investmentsπŸ“… 15 years investingπŸ—“ Last invested Mar 2025𝕏 @upgrade_to_unlock
Operator-angel🌍 Canada
6
Total investments
5
Early stage
1
Mid stage
0
Late stage
15y
Years active

Portfolio

6 investments Β· sorted by recency
All investments
Early stage
Mid stage
Late stage
Board Member
Mar 2025
Reconnecting humanity, one conversation at a time
Board Member
Aug 2023
At Flora Fertility, were on a mission to empower the next generation of parents, by putting control of your reproductive health outcomes back where it belongs: in your hands. By creating the first indivdually-owned fertility benefits solution, were revolutionizing the way womens health and family building are funded. With affordable insurance options and a supportive community, Flora is breaking down barriers and making fertility care more accessible to all.
early stageInsurance
Board Member
Aug 2021
Requity Homes is creating a fair, feasible, & flexible new path to owning a home.
early stageReal Estate
Board Member
Apr 2019
Relay is built for both wholesale brokers and retail agents. It equips them with a friendly interface to easily add specialty lines to their client proposals. Relay lets agencies and brokerages quickly add Cyber Insurance to any quote, and also supports Management Liability and Small Commercial/BOP. Forward-looking agencies and brokerages in North America use Relay to place more business, faster and better.
early stageInsurance
Board Member
Apr 2015
We help modern sales teams create, send, track, and e-sign winning proposals, contracts, and agreements. Proposify is the proposal software that gives you control and insight into the most important stage of your sales process: the close. From design to sign-off, get the confidence and consistency to dominate your deals. This is how you close.
Board Member
Jul 2011
Localmind gives you the ability to know what's happening in the world, right now. By temporarily and anonymously connecting you to someone at the location you are interested in, you are able to ask any question you want about that location, and get an answer, in real-time.
Experience Β· 11 entries
All (11)
Investments (6)
Founder (3)
Board (6)
2025
Board Member
Mar 2025
Reconnecting humanity, one conversation at a time
2023
Board Member
Aug 2023
At Flora Fertility, were on a mission to empower the next generation of parents, by putting control of your reproductive health outcomes back where it belongs: in your hands. By creating the first indivdually-owned fertility benefits solution, were revolutionizing the way womens health and family building are funded. With affordable insurance options and a supportive community, Flora is breaking down barriers and making fertility care more accessible to all.
early stageInsurance
2021
Board Member
Aug 2021
Requity Homes is creating a fair, feasible, & flexible new path to owning a home.
early stageReal Estate
2019
Board Member
Apr 2019
Relay is built for both wholesale brokers and retail agents. It equips them with a friendly interface to easily add specialty lines to their client proposals. Relay lets agencies and brokerages quickly add Cyber Insurance to any quote, and also supports Management Liability and Small Commercial/BOP. Forward-looking agencies and brokerages in North America use Relay to place more business, faster and better.
early stageInsurance
2016
Founding Partner
Jul 2016
Highline Beta is a hybrid corporate venture studio and VC firm that evolves the traditional management consulting model to put things into action, not just strategize in the clouds. We work with large corporates and family offices to identify and validate new growth opportunities and build ventures (spin-ins and spin-outs). We help companies and family offices design, build and run corporate venture studios, enabling them to repeatedly develop new businesses. Some of our clients include: RBC, AB InBev, Colgate-Palmolive, Cincinnati Insurance, Greenshield Canada, Munich RE, Mattel, 1848 Ventures and others. We work with executives to build new ventures both inside and outside of their organizations to unlock new areas of growth. We bring a startup mentality and execution capabilities to our corporate clients to help them grow beyond their core. Highline Beta is led by entrepreneurial leaders with track records of starting successful businesses and building incredible value, and we work with some of the world’s best-known companies to help them solve their growth innovation challenges.
Show all 11 entries ↓
Investment activity
2011–2025 Β· 6 investments
201112015120191202112023120251
Recent (last 2 years)Earlier