# Top 40 Retail Angel Investors in Canada in May 2026

## Tom Williams
- Type: Angel
- Location: San Francisco, California, United States
- Relevant deals: 3
- Stages: Seed, Series A, Series B
- Focus: Software, Health Care, Financial Services

Tom Williams

## Diplo (Thomas Pentz)
- Type: Angel
- Location: Los Angeles, California, United States
- Relevant deals: 3
- Stages: Series A, Seed, Angel
- Focus: Apps, Media and Entertainment, Financial Services

Diplo is an investor of Thomas Wesley Pentz, born November 10, 1978, better known by his stage name Diplo, is a Grammy-nominated American DJ, music producer, rapper and songwriter based in Los Angeles, California. He founded and manages record company Mad Decent, as well as co-founding the non-profit organization Heaps Decent. Amongother jobs, he has worked as a school teacher in Philadelphia. He is also the co-creator and lead member of the electronic dancehall music project, Major Lazer. His 2013 EP Revolution debuted at number 68 on the US Billboard 200.During his rise to fame, Diplo worked with British musician M.I.A., an artist who is credited with giving him exposure in his early career. Later, he and fellow M.I.A. producer Switch created a Jamaican dancehall project titled Major Lazer. Since then, Diplo has worked on production and mixtape projects with many other notable pop artists, such as Britney Spears, Beyoncé, No Doubt, Justin Bieber, Usher, Snoop Dogg, CL and G-Dragon. His alias, short for Diplodocus, derives from his childhood fascination with dinosaurs. He is the co-producer of several tracks on Madonna's 2015 album Rebel Heart (2015) and he collaborated with Skrillex to create the group Jack Ü.Source: 

## Harley Finkelstein
- Type: Angel
- Location: Ottawa, Ontario, Canada
- Relevant deals: 2
- Stages: Seed, Series A, Pre-Seed
- Focus: Artificial Intelligence, Machine Learning, Apps

Harley Finkelstein is the Co-Founder of Firebelly Tea and the President of Shopify. He previously worked at C100 as a Board Member. Harley Finkelstein attended the University of Ottawa and Concordia University.

## Roham Gharegozlou
- Type: Angel
- Location: San Francisco, California, United States
- Relevant deals: 2
- Stages: Seed, Series A, Pre-Seed
- Focus: Blockchain, Software, Cryptocurrency

Roham is founder and CEO of Axiom Zen, an award-winning venture studio that specializes in emerging technology. Axiom Zen’s first public blockchain project, CryptoKitties, is the world’s most successful blockchain game and the first decentralized application to effectively engage a consumer audience. CryptoKitties has been covered by Fortune,Bloomberg, and the BBC, accounting for roughly a quarter of the Ethereum network’s traffic within a week of launch and introducing hundreds of thousands of new users to blockchain technology. Axiom Zen was named first among Canada’s Most Innovative Companies by Canadian Business. Their products have touched 200+ million consumers and are used by the world’s leading companies, including Facebook, Microsoft, and NASA, as well as by eminent academic institutions and government organizations. They pride themselves in diversity of talent: a team of ~80+ creatives includes published authors, over a dozen former founders, diversity from 20+ national origins, and decades of collective experience at startups and Fortune 500s alike. Axiom Zen has been working with Bitcoin and various forms of blockchain and distributed ledger technologies since 2014. Axiom Zen is also the team behind ZenHub, the world’s leading collaboration solution for technical teams using GitHub; and the developer of Timeline, named Apple’s Best App of January, Editor’s Choice in 10 countries, and Best New App in 88 countries. Axiom Zen is the creator of Toby, recognized as Top Chrome Extension of the year by both Google and Product Hunt, and the parent company of Hammer & Tusk, a leader in the world of immersive experiences (AR/VR). Axiom Zen's work has been featured in TIME Magazine, The New York Times, Vice, and Fast Company. History Prior to founding Axiom Zen, Roham served with the Rising Tide Fund bas

## Russell Cook
- Type: Angel
- Location: San Francisco, California, United States
- Relevant deals: 2
- Stages: Seed, Series C, Series D
- Focus: Food Delivery, Logistics, Delivery

Russell is the Co-Founder & President of FitOn, Founder of AllTrails (sold to Spectrum Equity), former SVP Operations / Angel Investor @ Postmates (sold to Uber) and former CTO of beRecruited (sold to The Raine Group). He studied electrical engineering, computer science and economics while attending Duke University.

## Manny Bahia
- Type: Angel
- Location: Toronto, Ontario, Canada
- Relevant deals: 1
- Stages: Seed
- Focus: Retail, Fashion, Marketplace

Manny Bahia - CRO @ Daily Hive

## Caroline Somers
- Type: Angel
- Relevant deals: 1
- Stages: Seed, Angel
- Focus: Retail, Fashion, Shopping

Caroline Somers - Chair @ Capital Angel Network

## Markus Frind
- Type: Angel
- Location: Vancouver, British Columbia, Canada
- Relevant deals: 1
- Stages: Seed, Series A, Series B
- Focus: Retail, FinTech, Financial Services

Markus Frind

## Lev Ekster
- Type: Angel
- Location: New York, New York, United States
- Relevant deals: 1
- Stages: Seed, Series A, Series D
- Focus: E-Commerce, Consumer Goods, Lifestyle

Lev Ekster is the Chief Strategy Officer (CSO) at Bowlero Corporation . Lev Ekster attended New York Law School.

## Jamie True
- Type: Angel
- Location: London, England, United Kingdom
- Relevant deals: 1
- Stages: Seed, Angel
- Focus: E-Commerce, Video, Retail

Jamie is the CEO and driving force behind LifeWorks. Combining energy and positivity, he is deeply passionate about technology and how it can be used to create positive change in our world today.With a proven track record of growing technology companies from the ground up, Jamie set up his first business at the age of 17 which merged with itslargest competitor in June 1997. He co-founded and invented Interclubnet PLC, creating an online trading platform that most major football clubs worldwide used to buy and sell players akin to a Bloomberg terminal "X-tranet". In August 2000 the company floated on AIM with a market capitalisation of £30 million. Turnover in Year 1 totaled £8.1Million.In January 2004, Jamie launched a 9 patented service called ONSPEED which became the largest Internet accelerator in Europe. The group subsequently floated under a holding company called Z Group PLC in June 2005 for £25 million on AIM.In Jan 2010, Jamie started Grapple mobile, a patented mobile application platform. Grapple won the most Innovative Mobile Agency of 2012 and 2013 and was successfully acquired by Monitse PLC (MONI) AIM for up to £39million in Sep 2013.Jamie founded WorkAngel in 2013, the powerbrand that drives employee engagement, retention and satisfaction for some of the largest companies in the World. WorkAngel merged with Ceridian LifeWorks in 2016 with Jamie serving as the CEO of LifeWorks.

## Simon Whitfield
- Type: Angel
- Location: Vancouver, British Columbia, Canada
- Relevant deals: 1
- Stages: Seed
- Focus: Retail, Cycling, Consumer

Simon St. Quentin Whitfield (born 16 May 1975 in Kingston, Ontario) is a retired Olympic triathlon champion from Canada.

## Brenda Irwin
- Type: Angel
- Location: Vancouver, British Columbia, Canada
- Relevant deals: 1
- Stages: Seed, Series A
- Focus: Communities, SaaS, Music

Brenda Irwin joined the Providence Health Care Board in 2012.Brenda is the founder of Angel Links Capital, managing investments for private investors across a range of sectors, including health and wellness. Previously, she was a venture capitalist for 13 years as a member of BDC Venture Capital’s life sciences team. Before entering the worldof finance, Brenda enjoyed a career as a middle school science teacher.Her other non-profit experience includes tenure as vice-president for the Take A Hike, Youth At Risk Foundation while it went through a decade of program growth and community expansion. She is dedicated to mentorship and finds time to explore British Columbia’s beauty when training for triathlons. Brenda has a BSc from the University of Guelph and an MBA from the University of British Columbia.

## Reetu Gupta
- Type: Angel
- Location: Markham, Ontario, Canada
- Relevant deals: 1
- Stages: Seed
- Focus: Retail, Fashion, Marketplace

Reetu Gupta is the Co-founder & Chief Strategy Officer at Rogue Insight Capital Ltd. Reetu attended the Schulich School of Business.

## Anna Sinclair
- Type: Angel
- Relevant deals: 1
- Stages: Angel
- Focus: Retail, Fashion, Shopping

Anna Sinclair is an award-winning entrepreneur, early-stage investor and CEO of Total Mom Inc. She produced Canada’s largest holistic festival for moms called “The Total Mom Show” in partnership with some of North America’s largest brands. Recognized as one of the Top 100 Most Powerful Women In Canada, top 50 influential women leaders, and Womenof Influence, Anna has been featured in Forbes as a contributor and Business Council member.She grew a massive community network of moms juggling motherhood and business. This online e-learning education community platform helps women grow, start, and grow their businesses with a focus on growing social and financial capital through a profitable and sustainable business model.Today, Total Mom has an annual reach of 24M + in Canada & US. She supports ambitious founders through a community of 20k+ moms, making it known as one of the fastest-growing online professional networks of mom entrepreneurs. Her experience working with over 350+ brands gives her the knowledge and experience to touch any aspect of a project from top to bottom. She secured over 3 million in sponsorship dollars to date through her firm Sinclair Creative Agency Inc., where she advises both individuals and consumer lifestyle brands on branding and business strategy, content marketing, and asset development.

## James Appleyard
- Type: Angel
- Location: Toronto, Ontario, Canada
- Relevant deals: 1
- Stages: Seed
- Focus: Software, Machine Learning, B2B

James Appleyard is an experienced technology investor and operator, with a desire to combine strong investment outcomes with human progress. Having spent the past decade helping build the fundraising technology company Artez Interactive into an international success, with presence in Canada, the U.S., Australia, and the U.K, the company'ssale in 2013 has enabled him to focus on supporting other entrepreneurs. A graduate of The London School of Economics and the Rotman School of Management at the University of Toronto, James has contributed to building a number of innovative companies and other organizations.

## Ryan Holmes
- Type: Angel
- Location: Vancouver, British Columbia, Canada
- Relevant deals: 1
- Stages: Seed, Angel, Pre-Seed
- Focus: Software, SaaS, Enterprise Software

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.

## Ben Narasin
- Type: Angel
- Location: San Francisco, California, United States
- Relevant deals: 1
- Stages: Seed, Series A, Pre-Seed
- Focus: Financial Services, Software, Mobile

Ben Narasin is the Founder and General Partner at Tenacity Venture Capital. He attended International Christian University, Babson College, and Harvard University.

## Jonathan Ehrlich
- Type: Angel
- Location: San Francisco, California, United States
- Relevant deals: 1
- Stages: Seed, Pre-Seed, Series A
- Focus: E-Commerce, Software, SaaS

Jonathan is a Venture Partner at Foundation Capital.Jonathan joined Foundation Capital as an EIR in January, 2013. Prior to Foundation, Jonathan co-founded Utah Street Labs, a Foundation portfolio company. Mr. Ehrlich was previously the Director of Marketing at Facebook. From November 2003 until 2007 he was the Executive Vice-President, Onlineat Indigo Books & Music Inc. (TSE: IDG), Canada's largest book retailer, where he was responsible for that company's Online business. Prior to joining Indigo, Mr. Ehrlich was an Entrepreneur-in-Residence at Mosaic Venture Partners and before that was a Co-Founder and Vice President of Marketing for MobShop Inc, a pioneer in Online eCommerce. MobShop was funded by GE Capital, Visa International, Mayfield Fund and Marc Andreessen. His previous business experience also includes several years at CYBERplex interactive media and MacLaren McCann advertising.He holds an MBA from the Richard Ivey School of Business and a BA in Political Science from the University of Western Ontario.

## Mike McCauley
- Type: Angel
- Relevant deals: 1
- Stages: Seed, Series A
- Focus: Software, Consumer Goods, Apps

Mike McCauley was co-founder of BufferBox (acquired by Google), a network of automated package delivery lockers. One year after its founding, BufferBox was awarded the 2012 Velocity Venture Fund, and went through the Y Combinator program in Silicon Valley. Mike is now Product Manager of early stage Google X projects and is based in Silicon Valley.Most recently he co-founded a start-up fund to help early-stage tech firms in the Waterloo Region in 2014. Mike completed a BASc, Mechatronics Engineering from the University of Waterloo in 2011 and is passionate about sharing his expertise as a founder with others.

## Jordan Banks
- Type: Angel
- Location: Toronto, Ontario, Canada
- Relevant deals: 1
- Stages: Seed, Series A, Corporate Round
- Focus: Software, Machine Learning, Information Technology

Jordan Banks is the Co-Founder at Thunder Road Capital. Jordan Banks attended York University - Osgoode Hall Law School.

## Jon Claydon
- Type: Angel
- Location: London, England, United Kingdom
- Relevant deals: 1
- Stages: Seed, Angel, Pre-Seed
- Focus: Software, SaaS, App Marketing

Jon Claydon

## Greg Kidd
- Type: Angel
- Location: San Francisco, California, United States
- Relevant deals: 1
- Stages: Seed, Series A
- Focus: FinTech, Mobile, Payments

Believer that ones identity credentials should be truly portable and owned by individuals themselves rather than corporations or governments. The trade-off between security and privacy can meet the needs of both traditional institutions worried about compliance and risk, but also consumer protection advocates who care about the underserved andunderbanked.Adviser/Investor via hardyaka.com for numerous startups in the exchange space including Shift, Ripple and 3taps, and previously Square and Twitter. Previously a director at Promontory Financial and a senior analyst for payments at The Board of Governor of the Federal Reserve. Senior Associate at Booz Allen. Founded and took Dispatch Management Services Corp public on the NASDAQ. Have worked as an instructor/leader for Outward Bound and the National Outdoor Leadership School.Specialties: Portable identity, digital currencies and exchange markets for goods, services, and information with functional emphasis on messaging, payments, and reputation/trust/risk. Well versed in visualizations for risk reporting and controls.

## Don Tapscott
- Type: Angel
- Location: Toronto, Ontario, Canada
- Relevant deals: 1
- Stages: Seed, Series A
- Focus: Retail, Shopping, E-Commerce

Don Tapscott, CEO of The Tapscott Group, is one of the world’s leading authorities on the impact of technology on business and society. He has authored 16 books including Wikinomics: How Mass Collaboration Changes Everything which has been translated into over 25 languages.Don has been advancing ground-breaking concepts for over 3 decades. His1992 bestseller Paradigm Shift helped coin the seminal management concept, and in 1995 his book The Digital Economy changed business thinking about the transformational nature of the Internet. Two years later he helped popularize the terms “Net Generation” and “the Digital Divide” in Growing Up Digital.Don’s most recent and perhaps most ambitious book is co-authored with his son, startup CEO and bitcoin governance expert Alex Tapscott. Blockchain Revolution: How the Technology behind bitcoin is Changing Money, Business, and the World has been a bestseller in Canada since its release in May 2016, and has been featured in nearly every major publication in North America since then. Blockchain Revolution is also in the process of being translated into 12 languages. In 2015, Don became a member of the Order of Canada, and was ranked the 4th most influential management thinker in the world by Thinkers50. He is Adjunct Professor at the Rotman School of Management, an Associate at the Berkman Klein Center for Internet and Society at Harvard University, and Chancellor of Trent University in Ontario.It is hard to imagine anyone who has been more prolific, profound, and influential in explaining today’s technological revolutions and their impact on the world.

## Kevin Liles
- Type: Angel
- Location: New York, New York, United States
- Relevant deals: 1
- Stages: Series A, Seed
- Focus: Music, Retail, Fashion

Kevin Liles, CEO, and Co-Founder at 300 Entertainment. He attended Morgan State University.

## Arlene Dickinson
- Type: Angel
- Location: Calgary, Alberta, Canada
- Relevant deals: 1
- Stages: Angel, Pre-Seed
- Focus: Food and Beverage, Health Care, Wellness

Dickinson, owner and CEO of Venture Communications, a company she grew from a small, local firm to one of the largest independent agencies in Canada, is also the CEO of District Ventures and Youinc.com. Companies all aimed at helping market, fund and grow entrepreneurs and entrepreneurial companies. She is a two times best-selling author,accomplished speaker and is best known to Canadians as one of the venture capitalists on the award-winning CBC series’ Dragons’ Den.

## Aubrey Graham (Drake)
- Type: Angel
- Location: Toronto, Ontario, Canada
- Relevant deals: 1
- Stages: Seed, Series A, Angel
- Focus: eSports, Shopping, Gaming

Aubrey Graham (Drake) is the Founder of OVO Sound.

## Farhan Thawar
- Type: Angel
- Location: Toronto, Ontario, Canada
- Relevant deals: 1
- Stages: Seed, Pre-Seed, Series A
- Focus: Software, Information Technology, SaaS

Farhan Thawar is the VP Engineering at Shopify. Attended University of Toronto - Rotman School of Management.

## Arjun Sethi
- Type: Angel
- Location: San Francisco, California, United States
- Relevant deals: 1
- Stages: Seed, Series A, Series B
- Focus: Software, Financial Services, FinTech

Arjun Sethi is a serial entrepreneur, investor, and executive, as well as a Co-Founder of Tribe Capital.Tribe Capital is a top-quartile venture capital firm focused on capturing a perpetual edge in venture and crypto using artificial intelligence and data science. Some of its noteworthy investments include Apollo.io, Carta, Docker, Kraken,Relativity Space, and Shiprocket.Arjun was previously a Partner at Social Capital where he led the Venture Team consisting of six full time GPs with a broad focus on early stage investing in the consumer and enterprise sector. Arjun has a long history of sourcing, winning and leading early stage deals. Arjun’s investments at Social Capital include notable companies such as Front, Carta, Swarm (Sold to SpaceX), Slack, Cloud Kitchens and Relativity Space. Arjun's track record includes being recognized as one of the top 100 angels in Silicon Valley through advisory, direct, and secondary investments across various stages. He has invested in high-profile names such as Frax, Snapchat, Lyft, OpenDoor, and Gusto. Prior to his work in venture, Arjun co-founded and sold two successful companies. After his second company, MessageMe, was acquired by Yahoo, he joined the executive team, where he was instrumental in driving mobile product usage from 100M to 1B monthly uniques and was a Board Observer on Alibaba. Before that, Arjun was the Founder and CEO of LOLapps, a mobile gaming company that grew to 100M monthly users and sold for $240M.

## Basem Hanna
- Type: Angel
- Location: Mississauga, Ontario, Canada
- Relevant deals: 1
- Stages: Seed
- Focus: Retail, Fashion, Marketplace

Basem Hanna is the Founder, Chairman, President & CEO. He previously worked at Ledn Inc. as an Advisor. Basem Hanna attended Ivey Business School at Western University.

## Danny Zhang
- Type: Angel
- Location: San Francisco Bay Area, California, United States
- Relevant deals: 1
- Stages: Seed, Pre-Seed, Series A
- Focus: Retail, Software, E-Commerce

believer and executor of data-centric, metrics-driven engineering developmentmath/science ==> profitable productdeliver; deliver; deliver.Specialties: 1) c++ / java / perl / python2) search / search advertising platform (E2E) / hadoop / data pipeline / linear optimization / solr /lucene3) no life, when I am at work;4) no work, when I am enjoying my life.

## Kevin Lin
- Type: Angel
- Location: San Francisco, California, United States
- Relevant deals: 1
- Stages: Seed, Series A, Pre-Seed
- Focus: Gaming, Information Technology, Video Games

Lin is the COO of Twitch, the world’s leading social video platform and community for gamers. He was instrumental in the 2011 launch of the platform when he joined Justin.tv in 2008. His role included attracting the site’s largest broadcasters and building out the partnership team among other activities which have helped grow the Twitch brand.Currently more than 100 million gamers gather every month on Twitch to broadcast live video, watch and chat about gaming, making the platform an industry leader.

## Andreas Penna
- Type: Angel
- Location: Miami Beach, Florida, United States
- Relevant deals: 1
- Stages: Seed, Series A, Pre-Seed
- Focus: Mobile Apps, Machine Learning, Artificial Intelligence

Andreas Penna - Co-Founder & General Partner @ West Quad Ventures

## Chris Rickett
- Type: Angel
- Relevant deals: 1
- Stages: Seed
- Focus: Retail

Chris Rickett, co-founder of Digital Main Street.

## Craig Hunter
- Type: Angel
- Location: Toronto, Ontario, Canada
- Relevant deals: 1
- Stages: Seed, Series A
- Focus: Retail, Lifestyle, Home Decor

CEO at Dwelling.co, angel investor in 60+ companies.
Previously was early Uber (first 50), first GM at Ritual ($160m+ raised), CEO at Bitmaker (acquired by General Assembly), and VP Growth @ ChefHero ($12m+ raised).

## Jason Green
- Type: Angel
- Location: San Mateo, California, United States
- Relevant deals: 1
- Stages: Series B, Series C, Series A
- Focus: Software, Enterprise Software, SaaS

Jason Green is a Founder and General Partner at Emergence Capital. He was a Member of Board of Directors at Yammer. He attended Harvard Business School.

## Kevin Pan
- Type: Angel
- Location: Shanghai, Shanghai, China
- Relevant deals: 1
- Stages: Series A
- Focus: Retail, E-Commerce, Consumer Goods

"Kevin Pan is an Associate of Sequoia Capital China. Prior to joining Sequoia in 2006, Kevin was a Vice President with China International Capital Corporation Ltd. (CICC), the leading investment bank in China. Kevin was involved in global and domestic equity offerings, M&A and financial advisory services. Prior to his investment bankingcareer, Kevin worked with the Private Equity Group of CICC. Kevin holds an MA and two BA degrees from Shanghai Jiao Tong University." (Source: 

## Dejana Dua
- Type: Angel
- Location: Toronto, Ontario, Canada
- Relevant deals: 1
- Stages: Angel
- Focus: Retail, Fashion, Shopping

Partner

## Matt Mullenweg
- Type: Angel
- Location: Houston, Texas, United States
- Relevant deals: 1
- Stages: Seed, Series A, Series B
- Focus: Software, Mobile, Apps

Matt Mullenweg is the CEO at Automattic Inc. Matt Mullenweg attended the University of Houston.

## Suraj Gupta
- Type: Angel
- Location: Toronto, Ontario, Canada
- Relevant deals: 1
- Stages: Seed
- Focus: Retail, Fashion, Marketplace

Suraj K. Gupta is the Co-Founder, President & CEO at Rogue Insight Capital Ltd. Suraj attended Columbia Business School.

## Mona Patel
- Type: Angel
- Relevant deals: 1
- Stages: Seed
- Focus: Retail, Fashion, Marketplace

Mona Patel, Founder, Vasant Cosmetics.

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