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Top 20 Legal Angel Investors in Canada in April 2025

Last updated: Apr 2025 A list of 20 angel investors that invest in Legal startups based in Canada. We rank investors based on the number of investments they made in Legal companies from Canada. We update this investor list every month.

Top 20 Legal Angel Investors in Canada in April 2025

Investor	Legal Canada investments
Sergio A. Escobar	2
Ignacio Plaza	1
Daniel Klass	1
David Naiman	1
J. Taylor Crandall	1
Conrad Whelan	1
Hanif Joshaghani	1
Vinny Lingham	1
Brian Cartmell	1
Matt Mastracci	1
James Lochrie	1
Michael Bluestein	1
Neil Grunberg	1
Lorne Abony	1
Gary Kivenko	1
Todd Bissett	1
Andrew Chau	1
Jack Newton	1
Josh Kivenko	1
Niccolo Masi	1

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Investor list

Sergio has a diversified investment portfolio of companies across the United States and Canada ranging from B2B Cloud & SaaS startups (leveraging Artificial Intelligence, Big Data, Analytics and Security) to B2C Consumer startups (leveraging Mobile Apps, IoT/Wearables and eCommerce). Sergio has +15 years of experience as a multiple timestech entrepreneur with startups in Aerospace, eCommerce, Manufacturing, AgTech and Financial Technologies. Over the last 8 years, he has been deeply involved in the international entrepreneurial scene (incubators and accelerators) through his involvement in Founder Institute, Techstars Startup Programs, McGill X-1, Startup Chile, Startup Peru, Startup Bootcamp FinTech London, MsB Tunisia, Flat6Labs Tunisia, Kuwait National Fund, World Bank 'Tech Entrepreneurship Program for Innovation in the Caribbean', Krypto Labs in the Middle East and Creative Destruction Lab in Artificial Intelligence. He has been pioneering the Canadian investment scene by launching one of Canada's very first super angel funds: BCFventures.vc

Investment focus

Software, SaaS, Real Estate
Funding Round, Seed, Series A
Canada, United States

Portfolio highlights

FightCamp — FightCamp delivers the most exhilarating and effective form of home fitness through interactive boxing workouts, streamed to your device on demand.
JITbase — JITbase helps to improve workforce efficiency and increase production capacity by collecting data from machines that no one else can access.
Athennian — Athennian's cloud-based legal entity management software is trusted by law firms, legal departments, and corporate secretaries for entity governance and compliance. Learn more.

Ignacio Plaza is a partner at Draper Cygnus.

Investment focus

Legal, FinTech, Finance
Seed
Canada

Portfolio highlights

Roxom — Roxom is the first Bitcoin Stock, Commodities and Crypto Exchange in human history.
iComply Investor Services Inc. — iComply is a global and intuitive digital compliance administrator that helps compliance teams cut down on tedious KYC work and better manage AML risk throughout the customer lifecycle.We use AI to automate multiple layers of data validation: facial biometrics, document authentication, AML search compilation and results filtering to cut the totalcost of compliance by up to 90%.

Daniel Klass is an experienced private equity investor with a BSC in Mathematics, MBA in Finance / Accounting, and a CPA. Daniel practiced accounting for a few years and then spent 10 years at TD Capital and EdgeStone Capital Partners (two of Canadaâ€™s largest merchant banks) before raising his own fund. As a result of his true passionfor the lower end of the mid market, Daniel created Klass Capital. He thrives on working closely with his portfolio partners and helping them to build successful, sustainable and scalable businesses. Klass Capital Fund I, LP, founded by Daniel in 2010, is driven by integrity, imagination, partnership and entrepreneurial spirit.

Investment focus

Software, SaaS, Legal
Series B, Pre-Seed
Canada, The Netherlands

Portfolio highlights

Lawbrokr — Lawbrokr™ is the on-demand legal marketplace for your transactional legal needs. Lawbrokr allows you to search, connect, and communicate with verified lawyers throughout North America, removing the friction of finding a lawyer that is right for you!At lawbrokr, we believe that the consumer experience of getting access to verified lawyers shouldbe simple, fast, and effortless. For Solo Practitioners, lawbrokr’s end-to-end platform puts each lawyer in control of their own demand by driving practitioners to be quick, and responsive to support the growth of their practice.Our goal is to help Solo Practitioners reduce monthly ad spend through traditional channels, and leverage lawbrokr’s technology to drive new business opportunities that are right for them. No lawyer should be sitting on page 25 of a directory waiting to be found. Through lawbrokr, lawyers can review, and accept prospective engagements when they want, reducing cost per acquisition, overhead, and billable hours.
Wonderflow — Wonderflow is a platform that turns the Voice of the Customer into winning decisions. Millions of product reviews are written every day. Wonderflow is the simplest AI-based solution to analyze them and turn this extremely vast stream of customer feedback into winning decisions.Wonderflow's unified VoC analytics help B2C companies extractvalue from consumer feedback like online reviews, support center records, and NPS. Its AI analyzes the Voice of Customers from all over the world, both from your buyers and your competitors'. The Natural Language Processing (NLP) technology then provides you with easy-to-digest insights, not complicated procedures, so that everyone in your company can access the best information in seconds.
Coconut Software — Create valuable experiences for both customers and staff with real-time insights, and grow your business with a simpler way to engage.

Founder at Wherewithal Partners Inc.

Investment focus

Apps, Legal, Mobile
Seed, Private Equity
Canada

Portfolio highlights

Coreio —
Capture.it — Capture.it is a billable time capturing application that automatically tracks billable minutes, which slip by during quick calls or email exchanges on its users’ smartphone or desktop. Running securely in the background and integrating with its users practice management system, the application records and allocates time and client details so usersdon’t have to. Capture.it was designed by lawyers on 2014 and is based in Toronto, Ontario.

J. Taylor Crandall is a Managing Partner of Oak Hill Capital Partners and has been part of the firm since 1986. Mr. Crandall has senior responsibility for originating, structuring and managing investments for the firm's Media and Telecom and Technology industry groups. Prior to joining Oak Hill, Mr. Crandall was a Vice President withthe First National Bank of Boston, where he managed a leveraged buyout group and the bank's Dallas energy office. Mr. Crandall earned a B.A. degree, magna cum laude, from Bowdoin College, where he has served on the Board of Overseers.

Investment focus

Legal, FinTech, Finance
Seed
Canada, United States

Portfolio highlights

Wine By Design, Inc. — theFactor - Revolutionizing the alcoholic beverage industry with innovative consulting. Specializing in content creation, strategy, and partnerships in New York, LA, and Napa.
iComply Investor Services Inc. — iComply is a global and intuitive digital compliance administrator that helps compliance teams cut down on tedious KYC work and better manage AML risk throughout the customer lifecycle.We use AI to automate multiple layers of data validation: facial biometrics, document authentication, AML search compilation and results filtering to cut the totalcost of compliance by up to 90%.

Conrad Whelan

Investment focus

Marketplace, Internet, Information Services
Seed, Pre-Seed, Series A
Canada, United States, United Kingdom

Portfolio highlights

Boxhub — Buy new & used shipping containers with Boxhub. We make buying a shipping & storage containers easy - get it delivered right to your door. Shop today!
Nana — Nana is a vertically integrated student-to-operator trade skills school, today focused on Appliance Repair. We work with some of the 35 million people who will lose their jobs by 2030 to tech automation, teaching them trade skills, building their experience through our mentorship program, and connecting them to good jobs on our marketplace. Byperfecting this pipeline and teaching life skills to a new generation of tradespeople, we are accelerating the retooling of America’s workforce and creating millions of economic opportunities.
Shackle — Shackle is an app uses by hotels to provides and maintain hassel free hospitality services in a digital way to guests and travelers.

Hanif is a serial entrepreneur who has raised $150M USD across the 4 companies he has founded and invested in over a dozen startups.

Investment focus

FinTech, Software, Financial Services
Pre-Seed, Angel, Series A
Canada

Portfolio highlights

Helcim Inc. — Helcim is a payments company that lets businesses accept credit cards with ease. Helcim focuses on delivering a better payment service by making it easier to sign up, providing smarter payment tools, and making it more affordable to get paid.
Flahmingo — Saving and investing are not intuitive financial skills for the majority of Canadians. Many Canadians believe investing is only for the rich or that it requires significant capital to start. However, the 'next generation' of investors is changing this narrative by learning by doing and investing early. These new investors are being morethan just conscious of their financial return by also seeking a social return, by investing in brands they know and love, trust, and whose vision they support.Flahmingo is a native mobile application that allows DIY investors to begin investing with as little as $5. Using our proprietary Pies and Slices technology, Flahmingo enables users to build a portfolio of their favourite companies and exchange traded funds (ETFs). Using scheduled deposits and automagic round ups (both investment automation strategies), users seamlessly grow and maintain a diversified portfolio through the purchase and sale of fractional shares'. These fractional shares allow Flahmingo users to own as little as $1 in companies like Tesla, Alphabet, Amazon and even Berkshire Hathaway.
Littlebird — Littlebird's Toddler CareTracker tells you where your child is, who they are with, and how they are doing. Littlebird has an expanding suite of features including cellular connection, GPS, heart rate, temperature, activity and mode trends and dynamic activity feed connecting you with your little one's caregivers.

Vinny Lingham is the Co-Founder and CEO of Rumi.ai(Waitroom). He previously worked at YPO as a Member. Vinny Lingham attended Harvard Business School Executive Education.

Investment focus

Blockchain, Internet, Cryptocurrency
Seed, Funding Round, Angel
United States, South Africa, United Kingdom

Portfolio highlights

Glif — Interoperable tools for the Filecoin network
Afterparty — Afterparty is a technology company behind the new Web3 platform enabling creators to directly monetize and manage NFT collector relationships
Collectibles.com — Collectibles is the Home of Collectors: Cards, Comics, Coins, Stamps and more. Connect with Likeminds, Trade and Showoff your Collection for free

Brian Cartmell has over 20 years of experience in information technology systems, working as a programmer to CEO of eNIC, the second largest domain registry company in the United States before it was acquired by Verisign in 2001. Cartmell was invited to testify before the United States senate in regards to Internet Governance by ICANN, is theinventor of five issued U.S. patents, led the successful battle against Hormel for the right to include the word "Spam" in trademarks that relate to email services, and is a major shareholder and board member of companies ranging from identity authentication services to all-natural zero calorie sodas.

Investment focus

Art, B2B, Legal
Seed, Pre-Seed
United States, Canada

Portfolio highlights

Binded — Binded lets creators claim their copyrights on the blockchain and protect them for free. A creator uploads their art or photos to Binded via our website or integrations with creative tools like Instagram. We create a timestamp in the Bitcoin blockchain and give a certificate as proof. We are developing technology to create uniquefingerprints for all copyrighted works and store them on the blockchain. Like Youtube’s Content ID system for the entire internet. For every copyright claimed, we scan the web and show matches for possible copyright infringement. In 5 years we hope to be the main way copyrights are registered and utilized.
Approve.com — Tipalti helps drive business growth by automating and simplifying accounts payable, mass payments, procurement, and employee expenses in one connected suite.
Vimba —

Matt lives to pursue challenging technical problems and push the envelope of computing. He served as CTO of DotSpots, and previously worked on building scalable and fast solutions for energy companies, both as desktop and web applications. Along with Ryan Perry, he worked with StumbleUpon to build a newest generation of IE Toolbar prior totheir acquisition by EBay.Matt has a BSc in Electrical and Computer Engineering from the University of Calgary

Investment focus

Legal, Software, Child Care
Seed, Angel, Convertible Note
Canada

Portfolio highlights

NOBAL Technologies — Adaptable to any environment, anywhere in the world, our interactive intelligent mirror solutions are designed to easily integrate with your physical space.
Athennian — Athennian's cloud-based legal entity management software is trusted by law firms, legal departments, and corporate secretaries for entity governance and compliance. Learn more.
CareGuide — We believe good people deserve the best care. Connect with housekeepers, nannies, pet sitters, and elder \ care providers with ease. Trusted and secure.

James Lochrie is an entrepreneur, angel investor, venture capitalist and volunteer. He is the Co-founder of the global fintech company Wave. He is a Partner at Thin Air Labs, overseeing Thin Air Fund 1 and the Capital team. He has worked with thousands of entrepreneurs to help them scale their companies and #BuildWhatsNext.

Investment focus

Software, Analytics, Health Care
Seed, Angel, Pre-Seed
Canada

Portfolio highlights

SomaDetect — SomaDetect measures every critical indicator of dairy quality (fat, protein, somatic cell counts, progesterone) from every cow at every milking. It uses no consumables (no chemicals, no cartridges, no lost milk), is extremely quick (results in seconds, not minutes), and accurate.
PayShepherd — PayShepherd helps manage contractor billing for industrial facilities and simplifies billing processes. Save time, money, and headaches.
StellarAlgo — Drive fan engagement and revenue across the entire fan journey. For Major Leagues, Emerging Leagues, Live Events, Media & Gaming, and Corporate Partnerships.

Michael Bluestein is a senior corporate and securities lawyer with about 10 years of experience; his strengths include driving for results, strategic thinking and superior client service. His goal is to provide clients with practical solutions to problems while being cognizant of turn-around time and budget. He attended the University of Torontoand Schulich School of Business - York University.Michael Bluestein have a strong background in M&A (purchase and sale of businesses) and corporate finance deals including helping companies incorporate, complete angel/vc financings, complete secured financings and achieve their IPOs. Michael Bluestein have advised public issuers and helped to create two new stock exchanges from the ground up. Michael Bluestein also have extensive tech company experience from his counsel roles as well as from founding a tech start-up. Corporate Counsel seeks to provide Bay Street expertise and service without the Bay Street price. We feel that clients should pay for great advice and not fancy overhead. We take a fixed-fee approach to most matters to ensure that you have a handle on legal fees.

Investment focus

Apps, Legal, Mobile
Seed
Canada

Portfolio highlights

Capture.it — Capture.it is a billable time capturing application that automatically tracks billable minutes, which slip by during quick calls or email exchanges on its users’ smartphone or desktop. Running securely in the background and integrating with its users practice management system, the application records and allocates time and client details so usersdon’t have to. Capture.it was designed by lawyers on 2014 and is based in Toronto, Ontario.

Neil Grunberg serves as Co-Founder and Vice President of Strategy and Corporate Development at AlayaCare Inc. Mr. Grunberg has spent more than 17 years focused on workforce management, mobility, and operational software. His breadth of expertise ranges from consulting and project management to pre-sales and then eventually onto managing sales andmarketing for a successful startup before joining the Vortex Connect team and then onto AlayaCare.

Investment focus

Software, SaaS, E-Commerce
Seed, Pre-Seed
Canada, Australia

Portfolio highlights

Lawbrokr — Lawbrokr™ is the on-demand legal marketplace for your transactional legal needs. Lawbrokr allows you to search, connect, and communicate with verified lawyers throughout North America, removing the friction of finding a lawyer that is right for you!At lawbrokr, we believe that the consumer experience of getting access to verified lawyers shouldbe simple, fast, and effortless. For Solo Practitioners, lawbrokr’s end-to-end platform puts each lawyer in control of their own demand by driving practitioners to be quick, and responsive to support the growth of their practice.Our goal is to help Solo Practitioners reduce monthly ad spend through traditional channels, and leverage lawbrokr’s technology to drive new business opportunities that are right for them. No lawyer should be sitting on page 25 of a directory waiting to be found. Through lawbrokr, lawyers can review, and accept prospective engagements when they want, reducing cost per acquisition, overhead, and billable hours.
Bloks, Inc. — Built purposely for venture teams. Works intelligently behind the scenes by eliminating all the busy work so you can focus on what matters -> picking and building winners
Monark — At the Monark Ventures, we help great ideas live up to their fullest potential. We create, lead, and succeed.

Lorne Abony is the Chairman of the Board at EMMAC Life Sciences. he was a former CEO and Chairman at Vested Finance.

Investment focus

Software, Apps, Legal
Seed, Series A
United States, Canada, Israel

Portfolio highlights

Socati — At Socati we produce customizable cannabinoid ingredients in a food-grade facility. Quality, with unrivalled consistency.
Schoold — Looking for an app that will make your college life tenfold easier? Here are the seven educational apps for students that deserve to be on your smartphone.
Voxia — Amy collects and analyzes information from all over the web and provides actionable insights about your leads, prospects and clients, all in one click.

Gary Kivenko is an experienced management professional with specialties in both operations and marketing strategy. Gary has worked in both large enterprise organizations, as well as emerging businesses. As Cyclica’s Vice President, Operations, he oversees business planning and execution, ensuring that the business is scaled and delivers tocustomers.Gary Kivenko has worked in emerging businesses as well as corporate enterprise, providing management, strategy, leadership, and solutions to problems for nearly 20 years. As Cyclica’s Vice President, Operations, he oversees operations planning and management, client in-take and engagements, project management, and lights-on activities. Prior to joining Cyclica, Gary spent considerable time undertaking independent management consulting projects mainly for start-up clients, as well as developing early stage investments in new ideas. His experience includes strategic planning and execution in IT, marketing and business development, and operations. Prior to this, Gary worked in wireless telecom as well as with consumer prepaid products in various marketing, operations, and planning roles. Gary’s well developed sense of planning, derived from years of cross-functional project success, and a just-do-it mentality, has been honed to help emerging companies find their footing and execute well. Gary is a graduate of the University of Toronto Rotman School of Management where he obtained an MBA, as well as Carleton University’s School of Computer Science where he obtained a Bachelor’s Degree in Computer Science.

Investment focus

Apps, Legal, Mobile
Seed
Canada

Portfolio highlights

Capture.it — Capture.it is a billable time capturing application that automatically tracks billable minutes, which slip by during quick calls or email exchanges on its users’ smartphone or desktop. Running securely in the background and integrating with its users practice management system, the application records and allocates time and client details so usersdon’t have to. Capture.it was designed by lawyers on 2014 and is based in Toronto, Ontario.

Todd Bissett is a corporate and commercial lawyer and partner in the Waterloo office of Miller Thomson. Todd practices primarily in the areas of private equity and venture capital, equity and debt financing, mergers and acquisitions and general corporate and business law. Todd co-heads Miller Thomson's Emerging Growth & Venture Capitalpractice group.Licensed in California as well as Ontario, Todd has previously practiced in Silicon Valley, California and for several years in Greater China, and frequently advises on complex, cross-border transactions and business arrangements. He represents both issuers and investors in investments, and sellers and buyers in M&A transactions, having worked extensively with major institutional and strategic investors, venture capital and hedge funds, and with companies and issuers from early stage start-ups to multinational public and private organizations. Todd has broad industry experience including software, telecommunications and value-added services, manufacturing, gaming, financial services, education, biotech and medical products and services.

Investment focus

Legal, Legal Tech, Information Services
Angel, Pre-Seed
Canada

Portfolio highlights

Alexi — Alexsei provides high quality comprehensive answers to legal questions, at a fraction of the cost and an unprecedented turnaround time - enabled by cutting edge scientific research, artificial intelligence and NLP technologies. Alexsei’s advanced artificial intelligence platform delivers affordable and high-quality answers to legal questions inmemo format.
Skout Deals —

Andrew Chau is the co-founder of Neo Financial He used to be the co-founder of SkipTheDishes. He handles business development and strategy for this company.

Investment focus

Apps, Software, Art
Seed, Angel, Pre-Seed
Canada, United States

Portfolio highlights

Resq — At ResQ, we're obsessed with simplifying the repairs and maintenance experience so you can focus on doing what you love. Talk to a ResQ Expert today!
Peggy — Peggy is a social marketplace that allows you to discover, buy, and sell investment-worthy art. A place for the art-curious and the art-expert, for the art gallery and artist. A new way forward for the art world.
Sanzo — The 1st Asian-inspired sparkling water, Sanzo uses real fruit + no added sugars to deliver refreshing taste. Whether these flavors are a taste of home or a source of discovery, we're excited to bring you authentic flavors in the most delicious way we know how.

An experienced business leader, software developer and entrepreneur, Jack provides the strategic vision that has made Clio a leader in legal cloud computing.

Investment focus

Legal, Legal Tech, Software
Seed, Pre-Seed, Series A
United States, Canada

Portfolio highlights

Tangibly — Tangibly is a platform for businesses to manage their intellectual property by securing their trade secrets in legally enforceable form.
Clearbrief — Do Justice to the Facts. Select any sentence in your Word doc, and our AI instantly finds the best evidence you have to support your argument. 1-Click TOA.
Hello Divorce — Hello Divorce makes divorce easier and more affordable. Learn about our affordable online divorce plans with as little or as much help as you need, and read our free divorce resources.

Josh Kivenko - Interim Principal @ Sweet Farm Capital

Investment focus

Apps, Legal, Mobile
Seed
Canada

Portfolio highlights

Capture.it — Capture.it is a billable time capturing application that automatically tracks billable minutes, which slip by during quick calls or email exchanges on its users’ smartphone or desktop. Running securely in the background and integrating with its users practice management system, the application records and allocates time and client details so usersdon’t have to. Capture.it was designed by lawyers on 2014 and is based in Toronto, Ontario.

President and CEO at Glu Mobile.

Investment focus

Apps, Legal, Gaming
Seed
United States, Canada

Portfolio highlights

Capture.it — Capture.it is a billable time capturing application that automatically tracks billable minutes, which slip by during quick calls or email exchanges on its users’ smartphone or desktop. Running securely in the background and integrating with its users practice management system, the application records and allocates time and client details so usersdon’t have to. Capture.it was designed by lawyers on 2014 and is based in Toronto, Ontario.
Astrocade AI — Astrocade AI is an AI-powered social gaming platform that allows anybody to create games and interactive experiences.
Autoverse Studios — Autoverse Studios offers Auto Legends, a competitive social auto racing game, focusing on car culture and player engagement, offering a multi-platform experience for real-time tuning and customization.

Investors by industry