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Top 50 Transportation Angel Investors in Canada in May 2025

Last updated: May 2025 A list of 50 angel investors that invest in Transportation startups based in Canada. We rank investors based on the number of investments they made in Transportation companies from Canada. We update this investor list every month.

Top 50 Transportation Angel Investors in Canada in May 2025

Investor	Transportation Canada investments
Jacky Chen	13
Ray Muzyka	13
Daniel Debow	12
Tobias Lütke	10
Barney Pell	9
Jevon MacDonald	9
James Lochrie	7
Roger Martin	7
Michele Romanow	7
Rasool Rayani	7
T. Chen Fong	6
Michael Katchen	5
Joseph Fung	5
Harley Finkelstein	5
Marc Altshuller	5
Paul Geyer	5
Tim Draper	5
Boris Wertz	5
Lance Tracey	5
Satish Kanwar	5
Jordan Banks	5
Andrew Wilkinson	5
Lance Priebe	5
Meltem Demirors	5
Alex Norman	5
Bryan Rosenblatt	5
Arjun Sethi	5
Manny Padda	4
Ellen Levy	4
Brice Scheschuk	4
Jamie McDonald	4
Scott Banister	4
Lee Lau	4
Michael Litt	4
Mike McCauley	4
Farhan Thawar	4
Gavin Uhma	4
Arlene Dickinson	4
Mark Pincus	4
Jean-François Grenon	4
Gerry Pond	4
Jason Warner	4
Patrick Lor	4
Mike Edwards	4
Kevin Mahaffey	2
Ryan Holmes	2
Stuart MacDonald	2
Tom Williams	2
Richard Cargill	2
Micheal Hyatt	2

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Investor list

General Partner, Board Director @ Archangel Network of Funds Managing Director (Canada) @ Wharton Alumni Angels

Investment focus

Software, IT, Hardware
Seed, Pre-Seed, Funding Round

Fellow @ Creative Destruction Lab (CDL) CEO & Founder @ ThresholdImpact

Investment focus

Health Care, Software, IT
Seed, Pre-Seed, Funding Round

Founder & CEO @ Helpful Fellow @ Creative Destruction Lab (CDL)

Investment focus

Software, Hardware, Science/Engineering
Seed, Series A, Pre-Seed

Founder & CEO @ Shopify Founder and CEO @ Shopify Plus

Investment focus

Software, Health Care, Financial
Seed, Series A, Series B

Associate Founder @ Singularity University Venture Partner @ Radical Ventures Co-Founder & CTO @ Moon Express Fellow @ Creative Destruction Lab (CDL)

Investment focus

Software, Mobile, IT
Seed, Series A, Angel

Co-Founder @ Startupnorth Fellow @ Creative Destruction Lab (CDL) Founder @ Volta Labs

Investment focus

Software, Data and Analytics, AI
Seed, Series A

Managing/Capital Partner @ Thin Air Labs Associate @ Creative Destruction Lab (CDL)

Investment focus

Software, IT, Other
Seed, Angel, Pre-Seed

Chair in Productivity & Competitiveness and Academic Director @ Martin Prosperity Institute - MPI

Investment focus

Software, Other, Hardware
Seed, Series A

Co-Founder & President @ Clearco Director @ Freshii Co-Founder @ Buytopia

Investment focus

Software, Consumer Goods, Education
Seed, Funding Round, Pre-Seed

Co-Founder & Managing Partner @ Pomme Natural Markets

Investment focus

Other, Mobile, Software
Seed, Angel

Fellow @ Creative Destruction Lab (CDL) Co-Founder @ Calgary Scientific

Investment focus

Software, Science/Engineering, Internet
Seed, Angel, Funding Round

Co-founder & CEO @ Wealthsimple

Investment focus

Software, Apps, Health Care
Series A, Seed, Pre-Seed

Co-Founder and CEO @ Uvaro Co-Founder and CEO @ Kiite

Investment focus

Software, IT, Other
Seed, Angel, Pre-Seed

President @ Shopify

Investment focus

Software, Science/Engineering, AI
Seed, Series A, Pre-Seed

Chairman @ Tacit Innovations

Investment focus

Mobile, Apps, Software
Seed, Angel, Funding Round

Director @ TIMIA Capital

Investment focus

Health Care, Sports, Gaming
Seed, Series A, Funding Round

Founder and Managing Partner @ Draper Associates Adviser @ Bancor Founder @ SpeedUPAfrica Co-Founder & Managing Partner @ DDF Founder @ DFJ VinaCapital Co-Founder & MD @ DFJ DragonFund Founder/Partner @ VenturesLab Founder & Partner @ Gotham Ventures Co - Founder & MD @ Zone Ventures Co-Founder @ ePlanet Capital Founder @ Draper University Ventures Co-Founder @ Draper Dragon Founder @ Draper Fisher Jurvetson

Investment focus

Software, Internet, Financial
Seed, Series A, Series B

Founder and General Partner @ Version One Ventures Lead independent director @ Ether Capital Fellow and Associate @ Creative Destruction Lab (CDL) Co-Founder and Investor @ Kobalt

Investment focus

Software, Mobile, Internet
Seed, Series A, Series B

Founding Partner @ Full Stack

Investment focus

Software, Internet, Community/Lifestyle
Seed, Angel

Investment focus

Software, Financial, Commerce/Shopping
Seed, Pre-Seed, Series B

Co-Founder @ Thunder Road Capital President @ Rogers Media

Investment focus

Software, IT, Other
Seed, Series A, Corporate Round

Founder @ MetaLab Founder @ Pixel Union Director @ Wecommerce

Investment focus

Software, Internet, Financial
Seed, Series A, Pre-Seed

Founder @ Hyper Hippo Games

Investment focus

Software, Gaming, Sports
Seed, Angel, Funding Round

Chief Strategy Officer @ CoinShares

Investment focus

Financial, Software, Other
Seed, Series A, Pre-Seed

Venture Partner @ Entrepreneur First Co-CEO, Founder, Business Developer @ HomeSav Associate @ Creative Destruction Lab (CDL) Managing Director @ TechToronto Canadian Partner @ AngelList

Investment focus

Software, Financial, Internet
Seed, Pre-Seed, Angel

Partner @ Craft Ventures

Investment focus

Software, Gaming, Hardware
Seed, Series A, Pre-Seed

Co-Founder & Partner @ Tribe Capital Board Partner @ Social Capital

Investment focus

Software, Financial, Internet
Seed, Series A, Series B

Founder @ New Avenue Capital Co-Founder @ Liquuid

Investment focus

Software, Sales/Marketing, Community/Lifestyle
Seed, Angel

Managing Director @ Silicon Valley Connect University Advisor @ Arizona State University

Investment focus

Software, Internet, Mobile
Seed, Series A, Funding Round

Chief Executive Officer @ Globalive Capital Co-founder, Director and Chief Financial Officer @ Globalive Communications CFO @ Biometric Update Associate @ Creative Destruction Lab (CDL)

Investment focus

Software, IT, Mobile
Seed, Pre-Seed

Investment focus

Software, Financial, Commerce/Shopping
Seed, Pre-Seed, Series A

Founder @ IRL

Investment focus

Software, Internet, IT
Seed, Series A, Angel

Partner and Co-Founder; Partner and Co-Founder @ Alignvest Management Corporation

Investment focus

Software, Science/Engineering, Hardware
Seed, Convertible Note

Co-Founder and CEO @ Vidyard Co-Founder and CEO @ Garage Capital

Investment focus

Hardware, Software, Internet
Seed

Co-founder and General Partner @ Garage Capital Associate @ Creative Destruction Lab (CDL)

Investment focus

Software, Mobile, Hardware
Seed, Series A

VP Engineering @ Shopify YC Continuity Advisor @ Y Combinator

Investment focus

Software, IT, Other
Seed, Series A, Series B

Cofounder and CTO @ Cape Privacy Co-Founder, CEO @ Sidestory Founder @ Slashjoin

Investment focus

Software, Internet, Data and Analytics
Seed, Series A

General Partner @ District Ventures Capital CEO @ District Ventures Plus CEO @ Venturepark Voice CEO @ Venturepark

Investment focus

Gaming, Food/Beverage, Health Care
Angel, Pre-Seed, Funding Round

Founder @ Reinvent Capital Team Member @ Yerdle

Investment focus

Software, Internet, Media and Entertainment
Seed, Series A, Series B

Managing Partner @ NTF Capital

Investment focus

Consumer Electronics, Hardware, Software
Series A, Angel, Series B

Chairman & Co-Founder @ Mariner Partners Co-Founder @ East Valley Ventures Co-Founder @ Pond-Deshpande Centre Co-Founder @ Propel ICT

Investment focus

Software, Sales/Marketing, Administrative
Seed, Funding Round, Series A

Managing Director @ Redpoint

Investment focus

Software, IT, Data and Analytics
Seed, Series A, Pre-Seed

Associate @ Creative Destruction Lab (CDL) Partner @ 500 Startups Canada

Investment focus

Software, Sales/Marketing, Commerce/Shopping
Seed, Series A, Angel

Chief Executive Officer @ Pioneer Media

Investment focus

Commerce/Shopping, Software, Internet
Seed, Angel

Kevin Patrick Mahaffey is the Founder of Lookout and SNR. He is also the Executive Chairman of Stork Club and an Investor.

Investment focus

Software, SaaS, Enterprise Software
Seed, Series A, Pre-Seed
United States, Canada, Israel

Portfolio highlights

Karman+ — Mining near Earth asteroids
Knostic — Knostic provides need-to-know access controls for Large Language Models (LLMs). Its knowledge-centric capabilities enable enterprises to expedite the deployment of LLMs and drive AI-powered innovation while maintaining value, security, and safety.
Resquared — Resquared has everything you need and more to reach local businesses. Contact data on every local business, optimized email and social outreach tools, and step-by-step built-in playbooks.

Ryan Holmes is the CEO and Founder of HootSuite. Thought leader, dog lover and serial entrepreneur, he has redefined the face of social media - bringing Twitter, Facebook and other social networks out of the dorm room and into the boardroom.Holmes has grown HootSuite from a lean startup to a global leader in social media with 8 million users,including 79 of the Fortune 100 companies. A college drop-out, he started a paintball company and pizza restaurant before founding Invoke Media, the company that developed HootSuite in 2009.Today, Holmes is an authority on the social business revolution, quoted in The New York Times and Wall Street Journal and called upon to speak at TEDx and SXSW Interactive Conferences. An angel investor and advisor, he mentors startups in Canada and around the world. Through HootSuite University, Holmes partners with major universities to deliver social media coursework to the next generation of business leaders.

Investment focus

Software, SaaS, Enterprise Software
Seed, Angel, Pre-Seed
Canada, United States, Hong Kong

Portfolio highlights

Truss — Send and receive business payments online with no limits, no percentage fees and no bullsh*t. Bring your business payments into the 21st century.
Surf — Surf for Brands allows you to generate the highest quality first party data, with consumer opt-in options. Generate ethical, high quality data now - Learn more
Kiwi Grocery — Kiwi Grocery cuts out the grocery store and delivers direct to your door. That means you pay less for your groceries and save on costly service fees. Kiwi users save 35% on their grocery checkout totals compared to other delivery apps.

Stuart MacDonald is a Venture Advisor of Narrative.Fund.

Investment focus

Software, SaaS, Travel
Seed, Funding Round
Canada

Portfolio highlights

Sherpa° — eVisas and travel requirements information for every step of your customer journey.
Swept — Swept is a tech company that develop software solutions for the janitorial industry. Swept was founded by Matt Cooper and Michael Brown in August 2014 and is based in Nova Scotia.

Tom Williams

Investment focus

Software, Health Care, Financial Services
Seed, Series A, Series B
United States, Canada, India

Portfolio highlights

Unito — Enterprise-grade integrations that sync business-critical tools. Secure, low-cost, two-way sync that anyone can set up and manage.
Delphia — Invest with your data, not your money.
NorthOne — NorthOne is an online Business Account with built-in features to make business banking fast and easy. No overdraft fees. No minimum balance. No hidden fees.

Richard Cargill is the founder of Turas Mara.

Investment focus

AgTech, B2B, Internet
Seed, Series A
India, Canada

Portfolio highlights

Toolsvilla — India's leading B2B eCommerce Marketplace for Machinery, Tools & Supplies that solve operational inefficiencies in Indian SMBs specially in the Agri-Food Category.
Milk Moovement — Milk Moovement is a powerful tool that connects all players in the raw milk supply chain. With features for transportation monitoring, production tracking, quality monitoring and producer payment, Milk Moovement is the only tool your team needs to manage raw milk.

Michael Hyatt is the Executive Chairman and Co-Founder of BlueCat Networks and a recipient of the Top 40 Under 40™ Award. BlueCat is a four-time winner of “Deloitte’s Fast 50” and has received Gartner’s highest “Strong Positive” rating. Michael also co-founded Dyadem, a highly successful software company that was acquired by IHS (NYSE: IHS).Michael is a weekly business commentator on CBC Newsworld and has been featured on the cover of Canadian Business Magazine. He is also a finalist in Ernst & Young’s Entrepreneur of the Year Award and an active participant and lender for three special charities: Kiva.org, OneProsper and Future Possibilities for Kids.

Investment focus

Software, SaaS, Accounting
Seed, Series A, Funding Round
Canada, United States

Portfolio highlights

MinuteBox — Secure legal entity management in the cloud. Minute books, transactions, compliance, document assembly, cap tables, e-signature, automated workflows
Enso Connect — Seamless digital guest experience from booking through the entire stay and long-lasting relationships after check-out. Vacation rentals & Hotels remarketing tool.
GoBolt — Elevate your logistics game while reducing your carbon footprint with GoBolt, your trusted 3PL provider focused on sustainability.

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