Building generational wealth isn’t about chasing fleeting trends or gambling on speculative bets. It’s about patiently investing in businesses with enduring competitive advantages, resilient cash flows, and the ability to compound value over decades. In Canada, two standout companies—Shopify (TSX:SHOP) and Constellation Software (TSX:CSU)—consistently demonstrate these qualities, making them potential cornerstones for growth-oriented investment portfolios designed to thrive across generations.
Constellation Software stock: The silent wealth multiplier
If there’s a masterclass in compounding, Constellation Software delivers it. This tech conglomerate operates like a well-oiled machine, quietly acquiring and integrating niche software businesses that serve mission-critical roles in industries like healthcare, logistics, and public services. These aren’t flashy startups; they’re essential tools with low substitutability, ensuring steady demand even during economic downturns.
What sets Constellation apart is its self-sustaining growth model. The company funnels cash flows from more than 1,000 subsidiaries into new acquisitions—each carefully chosen to bolster its ecosystem. This strategy has fueled revenue and earnings growth at a jaw-dropping +20% annual clip for over a decade.
Even as shares approach $5,000 apiece (up from about $1,200 in 2020), CSU stock remains surprisingly reasonably priced. With a forward price to earnings (P/E) of 38.7 and a somewhat reasonable P/E-to-growth (PEG) ratio under two, investors aren’t just paying for past success—they’re betting on a future where Constellation’s disciplined capital allocation continues to unlock shareholder value.
Constellation Software’s numbers speak volumes: 15.2% revenue growth and 17.3% operating earnings growth in the past 12 months, alongside strong returns on equity (ROE) consistently above 20%.
But the real magic lies in its predictability. While tech giants often rely on moonshot innovations, Constellation thrives by turning overlooked software gems into cash-generating pillars. For long-term investors, this isn’t just a steady capital growth stock—it’s a legacy-building engine.
Shopify stock: Powering the future of global commerce
E-commerce isn’t slowing down—it’s evolving, and Shopify sits at the center of this multi-decade revolution. SHOP’s e-commerce platform has become synonymous with entrepreneurship, empowering everyone from solo artisans to Fortune 500 companies to build and scale online stores. Recent strides, like capturing 12% of the U.S. e-commerce market (in Amazon.com’s backyard) and expanding into Europe and Japan, underscore its global ambitions.
After navigating post-pandemic turbulence, Shopify has emerged stronger. Revenue soared 25.8% year-over-year in 2024, while operating income swung from a $1.1 billion loss in 2023 to a $1.4 billion profit.
Shopify is sustainably generating positive free cash flow, giving it ample fuel to invest in artificial intelligence (AI)-driven tools, international expansion, and strategic acquisitions—all without diluting shareholders.
Critics might balk at Shopify stock’s forward P/E of 95.3, but context matters. This premium reflects its position as a gateway to the $6.3 trillion global e−commerce market. With zero debt and a fortress-like balance sheet, Shopify isn’t just surviving—it’s profitably shaping the future of how the world buys and sells.
Why Shopify and Constellation Software stock belong in your family’s financial blueprint
Generational wealth isn’t built overnight. It requires patience, foresight, and a long-term investment focus on businesses that can adapt and grow through economic cycles. Both Shopify stock and Constellation Software stock check these boxes—but in vastly different ways.
Shopify thrives on disruption. It’s a bet on the unstoppable rise of digital commerce, where small businesses and global brands alike need agile tools to connect with customers. Constellation Software, meanwhile, is the epitome of quiet consistency. Its success hinges on identifying undervalued software assets and integrating them into a cash-generating mosaic.
Together, they offer a balanced approach: one stock riding the wave of global innovation, the other mastering the art of disciplined execution. For investors with a 10- to 20-year horizon, this combination could anchor a portfolio designed to grow richer with each passing year.
Foolish bottom line
Creating generational wealth isn’t about timing the market—it’s about owning several exceptional businesses that compound value through thick and thin. Shopify and Constellation Software represent two sides of the same coin: visionary growth and methodical execution. While their paths differ, both share a common thread—the ability to turn today’s investments into tomorrow’s legacies. The two Canadian giants offer more than just lucrative returns; they offer a foundation for financial freedom that could last lifetimes for investors willing to hold through volatility.
