Constellation Software Shares Insights in its Annual General Meeting and Robinhood Enters the Canadian Crypto Market with $250 million CAD WonderFi Acquisition
Constellation Software Discusses the Future of its Business and Crypto Currency Firm Acquired in a Move to Further Expand in the Canadian Market
I often refer to Constellation Software as the gold standard for serial acquirers in my Substack, LinkedIn, and website posts. Their ability to compound returns for investors has been staggering. As one of the top performing companies on the TSX, Constellation’s share price has increased more than eightfold over the past 10 years. Looking further back, the company has been more than a 100-bagger, delivering a 280-fold return for investors since its IPO in 2006.
As an overview, Constellation Software is one of the world’s largest serial acquirers, with a market capitalization of over CAD $100 billion. They acquire and manage mission-critical software businesses that specialize in the specific needs of industries such as energy, healthcare, and real estate. On their website, they outline their acquisition criteria, which all serial acquirers can learn from.
Unlike most other publicly traded companies, Constellation does not conduct quarterly earnings calls. Their annual general meeting is where investors and other serial acquirers can learn how management is thinking about their business.
In the meeting, we learned a few things:
Despite macroeconomic uncertainty and increased competition from private equity and others emulating their model, the deal environment for VMS transactions remains unchanged. They aim to deploy $500 million to $800 million per year on small VMS transactions with an eye on larger deals.
Constellation is sharing best practices around how to use AI internally and noted that AI will accelerate software development. While management emphasized that the company operates in niche markets that have high switching costs or barriers to entry, they also acknowledged that there will likely be greater competition in less concentrated verticals.
Whether you’re an investor, founder, or serial acquirer, it’s definitely worth watching their annual general meeting for more insights on how the best in the business are viewing the landscape and preparing for technological disruptions like AI. Watching their annual general meetings has certainly become a yearly ritual for me to grow and stay on top of the latest developments in the serial acquirer space.
Toronto-based Acquisition Marks Robinhood’s Formal Entry into Canada’s Crypto Market
Robinhood, a U.S.-based trading platform that features a crypto wallet offering, has deepened its involvement in the space with a CAD $250 million acquisition of WonderFi, a Toronto-based cryptocurrency firm. This deal marks Robinhood’s formal entry into the Canadian market, a move strengthened by WonderFi’s standing as a key player in the country’s crypto landscape.
With this acquisition, Robinhood not only gains market access but also benefits from WonderFi’s track record as a serial acquirer. WonderFi currently owns two of Canada’s oldest and largest regulated exchanges, Bitbuy and Coinsquare, both of which will continue to operate under their existing brands.
Robinhood’s SVP Johann Kerbrat has described Canada as a “pretty attractive region,” noting that while there are no immediate plans to launch its broader product suite in Canada, the acquisition provides a foundation for growth, similar to Robinhood’s expansion in the U.S. and U.K. A full rollout in Canada could eventually position Robinhood to compete with local players like Wealthsimple, which manages over $73 billion CAD in assets. By comparison, Robinhood reported $187 billion USD in assets under custody as of March 2025.
Kerbrat emphasized Robinhood’s commitment to working closely with Canadian regulators, praising the country’s crypto framework as one “you can work with.” He added that Robinhood will continue to learn from WonderFi as it scales its crypto offerings globally.
This acquisition follows Robinhood’s purchase of Bitstamp in 2024 and aligns with its strategy to use crypto for growth worldwide. It also comes during a more crypto-friendly U.S. regulatory system, where the company contributed USD $2 million to President Trump’s inauguration earlier this year, aligning with the administration’s goal to make the U.S. “the crypto capital of the world.”
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Buffett’s Blueprint for Serial Acquirers
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LeadDyno has seen outstanding growth in 2024, with monthly EBITDA up 163% year to date. This success is the result of strategic pricing changes, product enhancements, and a user-first approach that continues to drive strong engagement and retention.
Excited to see what’s ahead for LeadDyno as it builds on this momentum!