Early Shopify Investor Bessemer Turned A $5 Million Bet Into $500 Million. It Could Have Been $22 Billion Today

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Shopify’s soaring stock has one venture capital firm looking at a $22 billion windfall that never was

Photo: Depositphotos.com/unomay

Thanks to skyrocketing demand for its online business-building tools, the Ottawa-based e-commerce giant has brought a windfall to its public market investors. Its value peaked at $84 billion last week, briefly making it the most valuable company in Canada, and pushing the net worth of its 39-year-old CEO Tobias Lutke north of $6 billion.

But for one of its earliest investors, San Francisco-based Bessemer Venture Partners, the hype around the company is bittersweet. The firm first invested $5.5 million in the company’s initial funding round, and after additional investments built a 26% stake worth $500 million when it went public in 2015. Though as is the typical modus operandi of venture capital firms — hold onto investments while the company scales and cash out following an IPO — Bessemer had redistributed all its shares back to its partners by the end of 2018, when the company was worth $15 billion.

Today Bessemer’s stake would currently be worth close to $22 billion, the firm says. In the past month, Shopify’s share price has doubled after it generated $470 million in revenue in the first quarter, as demand for its online tools has skyrocketed from brick-and-mortar retailers who have been forced online by the COVID-19 pandemic. Founded in 2006, it now has more than 1 million businesses using its platform, which provides a one-stop shop for companies to create websites with payment processing, order fulfillment and ad management. 

By exiting Shopify two years ago, Bessemer left at least $17 billion on the table. “I couldn’t comprehend that they would have this massive amount of success at that time,” says Alex Ferrara, the Bessemer partner who led Shopify’s initial funding round in 2010.

Even though a global pandemic does not factor into the forecast of most investors, Bessemer’s stake in Shopify stands out as a significant missed opportunity in venture investing because it is rare that a venture capital firm would have built such a large stake in a hot startup, says Will Gornal, a professor at the University of British Columbia’s Sauder Business School. “They’re probably kicking themselves.”

Venture capital funds are typically under pressure to post returns on investments in private startups over a relatively short period of time, between five and 10 years, says Gornal. Once a company goes public, a venture firm will often sell its shares back to its own investors, which include pension funds and university endowments, giving them the option to hold their stake in the company or cash out. This kind of mission isn’t conducive to reaping bigger returns that come years after a public offering, like those generated by other tech giants such as Amazon and Google. 

Shopify is among a handful of technology companies that have surged in value as the COVID-19 pandemic has forced society to rely on online tools. The big technology firms  Amazon, Microsoft and Google have floated around the $1 trillion valuation mark. The pandemic boosted the rise of newer arrivals, including Zoom, the video-conferencing firm that is now being used not only to connect office meetings but to hold family gatherings. After going public last year, the San Jose-based firm is now worth $44 billion, almost triple its value at the start of the year. Investors such as Emergence Capital Partners, which took a roughly 12% stake early in the company’s growth and says it still holds some of its shares, have had time to benefit from that public-market boost.

Some of Shopify’s early investors were being minted as billionaires even before the pandemic struck, including its CEO Lutke, his father-in-law Bruce McKean, and a couple who invested $750,000 early-on, as Forbes reported in February. But Bessemer is not alone among early investors in Shopify for exiting the company before the height of its riches were truly clear. Felicis Ventures, which invested alongside Bessemer in 2010, has since redistributed its shares back to its limited partners, the firm says.

While Bessemer’s one-time stake in Shopify might prove a once-in-a-lifetime type tech position, Ferrara says the firm will gladly take its realized returns on the deal: between 80x and 100x its initial investment. Says the venture capitalist: “We didn’t have a crystal ball.”

David Jeans, Forbes Staff

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