The Bootstrap Awards
The Annual Bootstrap Awards celebrate the achievements of self-capitalized businesses that have successfully grown with little to no external funding. These awards recognize the resilience, creativity, and determination of founders who have “bootstrapped” their ventures to commercial success.
Presented by The Ottawa Network, the Bootstrap Awards honour early-stage companies across all industries, both for-profit and non-profit, through a range of distinct, criteria-based categories.
Eligible recipients are entrepreneurs and organisations based in Eastern Ontario or Western Quebec that have been in operation for fewer than seven years and have raised no more than $750,000 in external funding (excluding non-convertible debt and grants).
Event Details:
This year’s Bootstrap Awards ceremony will take place on Tuesday, May 5th, 2026 from 5-8pm as part of Tech Tuesday with generous support from event sponsor Wesley Clover.
Award Categories
GREEN AWARD
The winner demonstrates how their company or organization is striving to improve the environment or contribute to environmental health or awareness through a combination of environmental and economic (commercial) sustainability.
INNOVATION AWARD
The winner demonstrates how their company has applied scientific and/or engineering expertise and technology to solve a problem in a way that is unique and innovative.
AI IN ACTION AWARD
The winner demonstrates how their company uses AI First and/or Agentic AI to provide a future-resilient product that has customer uptake and enthusiasm as shown in creative use of AI, number of customers, and/or growth.
MARKETING AWARD
The winner demonstrates how they used innovative marketing strategies to attract media attention and stakeholder involvement while cost-effectively acquiring customers and clients.
BOOTSTRAP CAPITAL AWARD
The winner demonstrates their ability to self-finance and “bootstrap” their enterprise with limited or no help from Angel or Venture Capital investors, and grow their business while remaining economically viable and profitable.
DISRUPTOR AWARD
The winner demonstrates how they are boldly trying to turn a business or paradigm on its head or changing an industry and have received some early traction from supporters. This award celebrates those who have a big vision and are taking a risk to make their vision a reality.
COMMUNITY IMPACT AWARD
The winner demonstrates how their efforts or organization has had an impact on the community in terms of social good by improving diversity, providing a service or product to an under-served community, raising awareness of a cause or initiative through a unique event, campaign, or fundraising program and by using innovative and/or entrepreneurial techniques. This award may be given to an individual entrepreneur or company.
FOUNDER OF THE YEAR AWARD
This winner demonstrates exceptional leadership and ability to grow their company and build their business through stakeholder engagement and networking, and/or shown themselves to be a leader and influencer in the business community, acting as a peer role model for other founders.