C&C Pod - Roy Rubin, Co-Founder of R-Squared Ventures & Magento

This week Bill and I are joined by Roy Rubin, Founding Partner of R-Squared Ventures & Co-Founder of Magento, joins the C&C Pod to mix up a classic low-ABV classic cocktail - an Americano - and talk about Roy’s lessons from founding and growing one the seminal commerce platforms of all time. We also explore Roy’s perspectives on the commerce tech market as it exists today, now as an investor.

Roy co-founded Magento back in 2008, and led the open-source commerce platform’s explosive growth. Magento was of course later acquired by eBay and then still later by Adobe, where it is now known as Adobe Commerce Cloud. More recently, Roy has gone on to co-found R-Squared Ventures - an early stage investment fund that invests in a number of software domains including Fintech, Digital Commerce, Marketplaces, and even AgTech.

I’ve enjoyed knowing Roy for many years, and it was great to bring him and his perspectives on the show.

So please pour yourself something to sip along with us and enjoy the conversation.

Cheers!

Episode Chapters:

* Intros and Americano cocktail history, cocktail culture, and connection

* “Hey Kai”: Understanding venture capital for kids, and the rest of us

* R-Squared’s investing approach & thesis

* The founding story of Magento

* Lessons learned from founding and scaling a high growth commerce start-up

* How to think about open source in today's market

* Innovation in the Israeli startup ecosystem, and how its responded to the ongoing conflict

* The AI revolution in commerce

* Taking a sabbatical, and the transformative power of travel - on yourself and family

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This week’s cocktail - an Americano

First thing, the Americano cocktail is not a coffee drink, it is a quintessential aperitivo with a storied history that reflects both its Italian origins and its role in the evolution of modern mixology. First appearing in the 1860s at Gaspare Campari's Caffè Campari in Milan (it’s still there!), the drink was originally known as the ‘Milano-Torino’, named for its two primary ingredients: Campari - from Milan, and Turin’s sweet vermouth. Served over ice and topped with a splash of soda water and a slice of orange, this low-ABV cocktail became a popular choice for Italians looking to ease into their evenings with something light, bitter, and refreshingly effervescent while warming up their appetites.

By the early 20th century, the drink gained popularity among American tourists in Italy during Prohibition, earning its new moniker, the Americano, in their honor. Its simplicity, balance, and accessibility made it a gateway to the world of bitters and aperitifs for many. The Negroni owes it’s origin to the Americano, emerging as a stronger variation when Count Camillo Negroni supposedly requested gin be used instead of soda water in his Americano the late nineteen-tens. This evolution further cemented the Americano as a foundational pillar in the cocktail canon - mixing bitters with sweet vermouth.

As a credential to its suave, easy sophistication, the Americano was actually the first cocktail James Bond orders in Ian Flemming’s first Bond book, Casino Royale - well before the Vesper.

A great template, over the decades the Americano has seen countless creative reinterpretations, from variations incorporating flavored bitters or different vermouth styles to updated presentations in highball glasses or with artisanal mineral waters. Yet, its essence remains unchanged—a harmonious blend of bitter, sweet, and sparkling elements. Today, the Americano serves as both a nod to its rich history and a modern-day ambassador of the Italian and European aperitivo tradition, proving that even the simplest cocktails can leave a lasting imprint.

Cheers!

Americano Cocktail Spec (Serves one)

1 1/2 oz (~ 45ml) - Campari

1 1/2 oz (~ 45ml) - sweet vermouth

Soda water, chilled, to top & taste

Garnish: orange twist

The process:

Fill a rocks or highball glass with ice, then add the Campari and sweet vermouth. Top with the soda water and stir gently to combine. Garnish with an orange twist.

Please share! There is plenty of room for others at the cocktail party! Why not share a drink and an interesting perspective to talk about while you enjoy it! Please share with you network or workplace today. Thank you!

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Be well, be safe, and here is to good business! Cheers! - Brian & Bill

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