Cocktails & Commerce Podcast

This week Bill and I are joined by Scot Wingo, founder and CEO of early-stage agentic commerce start-up, ReFiBuy and the podcast and Substack Retailgentic - where he focuses on Agentic Commerce. When we wanted to focus on the topic of Agentic Commerce, we could think of no one better than Scot to come on and talk about.Scot is a serial entrepreneur with an impressive and long background in commerce. Scot founded Channel Advisor in 2001, and later took it public in 2013. He later started Spiffy to explore digital car care services and this year he started ReFiBuy. Scot is also active in the VC community in North Carolina’s Research Triangle. Besides Retailgentic, Scot co-hosts the Jason & Scot Show - a podcast with friend of Cocktails & Commerce, Jason Goldberg.We cover a lot of agentic ground on the episode, so please pour yourself something to sip along with us and enjoy the conversation with Scot.Cheers!Episode Chapters:* “Wake me up and F*** me up,” introducing the Espresso Martini* Hey Kai, defining Agentic Commerce* The Future of Agentic Shopping: Trends and Predictions* Challenges in Payments and Transactions* Building trust in Agentic Commerce* Navigating the new landscape of Retail and AI* The role of context and authority in Product Discovery* The future of Retailer-Agent interactions* Agentic Commerce’s impact: Winners and losers* Monetization models in Agentic Commerce* Transforming the marketing tech stack* Imagining the future of Agentic Commerce* What’s up with one ‘t’ in “Scot”?For more on Agentic Commerce see our last C&C newsletter on Substack: Surf’s Up! The Next Wave of Commerce is Here - Amplified and Shaped by AI Thanks for listening to Cocktails & Commerce! Subscribe to receive all our content - including industry analysis and cocktails! This week’s cocktail: Espresso MartiniThe Espresso Martini’s origin story is as sleek and irreverent as the drink itself. In the late 1980s, Dick Bradsell - then bartending at Fred’s Club in London - was cleaning up after an espresso training in the afternoon when he was approached by a young model with sunglasses on who asked for something that would, “Wake me up, and then f*** me up.”Bradsell turned back to the espresso machine and went to work - pulling together vodka, fresh espresso, coffee liqueur, and sugar syrup together in a shaker and created what was originally called the “Vodka Espresso.” Served in a V-shaped glass with a creamy head and three coffee beans as garnish (a nod to the traditional Italian garnish symbolizing health, wealth, and happiness), the drink quickly became a London staple. It was later rechristened the “Espresso Martini” during the ’90s martini craze, cementing its place in cocktail history.Fast forward to today, and the Espresso Martini is having a moment. Many claim it is among the most over-rated of cocktails, but it’s popularity ensures it is everywhere there is a party brewing. The drink bridges two once disparate worlds—caffeine and spirits—and appeals equally to cocktail neophytes and seasoned enthusiasts.On Instagram feeds, in dive bars, and at high-concept cocktail dens, the Espresso Martini has evolved from a clubbing indulgence to a canvas for mixology: think cold brew riffs, mezcal substitutions, and even non-alcoholic versions for the sober-curious.Bradsell unfortunately left us early, but his creation didn’t just survive decades of shifting tastes—it influenced them, proving that a well-balanced drink can be both a pick-me-up and a cultural icon. For more on Bradsell and the Espresso Martini see C&C Issue No. 18Espresso Martini Cocktail Spec2 oz - vodka (or sub gin or tequila)1 oz - Kahlua or other coffee liqueur1 oz - strong, fresh, cooled espresso1 tsp - simple syrup (optional)Garnish - 3 coffee beansStepsAdd all ingredients to a cocktail shaker and shake vigorously until well chilled. (Dry shake optional to increase foam). Serve up in a coupe or martini glass. Garnish with the coffee beans set in the foam.Please share! There is plenty of room for others at the cocktail party! Thank you!As always, it’s great to have you here! If you enjoyed this episode, please subscribe, share, rate (it helps!), and let us know your thoughts. We love to hear from our listeners.REMINDER: SEND US YOUR QUESTIONS! Call or Text our Google Voice number: +1 831-704-6665Be well, drink well, and here is to good business! Cheers! - Brian & BillCocktails & Commerce™ is a wholly owned subsidiary of StrategyēM, LLC. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cocktailsand.substack.com

Maju Kuruvilla, Founder and CEO of Spangle AI, has an impressive background with leadership roles at Bolt and Amazon. He discusses how Spangle leverages generative AI to personalize the commerce experience, transforming how consumers shop online. Maju explains the innovative 'ProductGPT' and the concept of agentic commerce, where AI-powered shopping agents enhance customer interactions. He also emphasizes the urgency for brands to adapt to shifting consumer behaviors driven by technology. Join them for a delightful cocktail conversation!

Bobby Morrison, Chief Revenue Officer at Shopify since 2022 and a former executive at Intuit and Microsoft, dives into the dynamic world of enterprise commerce. He discusses Shopify's strategic focus on B2B markets and its plans to expand into new verticals. Bobby emphasizes the importance of partnerships and the urgent migration to Shopify's platform. They also explore the rise of non-alcoholic beverages, insights on digital commerce's future, and how AI will shape the landscape. It’s a rich blend of business insight and personal anecdotes!

This week Bill and I are joined by Raj De Datta, Founder and CEO of Bloomreach to mix up a Kir Royale cocktail and talk about Raj’s perspective on the market, his many lessons from founding and leading Bloomreach, and AI’s impact on the future of commerce experiences, digital marketing, and how merchants and marketers work going forward.Many of you will know Raj, Co-Founder and CEO of Bloomreach, a significant player in commerce search, personalization, and marketing automation markets. What you may not know is that Raj is a multiple-time entrepreneur, investor, and very into tennis - including serving on the Council for Player Development at the US Tennis Association.I have known and of course worked with Raj for many years, and always enjoy our conversations about the market and where things are headed. We cover a lot of ground, so please pour yourself something to sip along with us and enjoy the conversation.Cheers!Episode Chapters:* Cocktail chat - the Kir Royale & Wimbledon* Hey Kai, understanding Bloomreach* Raj’s Bloomreach Founder’s Story* Navigating challenges: Pivots and strategic shifts* AI’s impact on consumer experiences* The evolution of digital marketing: From workflow to data* The impact of AI Search and aggregators on Digital Commerce* The future skills needed for marketers and merchants* The growing importance of business agility* Lessons in category creation & evolving Bloomreach + The Exponea acquisition story* Thoughts on the future of the Commerce Tech market* Tennis as a metaphor for entrepreneurshipPlease subscribe! We want to be sure you make it to the next party! Cheers!This week’s cocktail - the Kir RoyaleThe Kir Royale is a variation on the Kir, a once popular French drink combining dry white Burgundian wine with crème de cassis that dates back to the 19th century and was further popularized after World War II. Crème de Cassis is a sweet, dark red liqueur made from macerated blackcurrants, traditionally from the Burgundy region of France. It originated in the mid-19th century, evolving from a medieval French medicinal elixir, and rose to prominence thanks largely to the Kir and Kir Royale. You can use many sweet liqueurs in a Kir, and Brian used Crème Yvette in his. This is a violet liqueur originally produced in the late 19th century in the U.S., made with parma violets, berries, citrus peel, honey, and vanilla. After disappearing from the market for decades, it was revived in 2009. Slightly drier in flavor than Cassis it is perfect for classic cocktails like the Aviation or to make a Kir Yvette.The Kir Royale sets itself apart by specifically calling for Champagne, while another variation, the Kir Imperial, calls for sparkling wine and raspberry liqueur rather than cassis.Aside from being delicious, the best thing about the Kir Royale might be how easy it is to make. Great for brunches and large gatherings (Mother’s Day people!). The scant half ounce of crème de cassis permeates the Champagne, resulting in a gorgeous cocktail with a hint of berry sweetness. Be sure to pour the liqueur into the glass first, followed by the Champagne, which ensures the ingredients will mix naturally. A bit more or less cassis can fine tune the cocktail to one’s individual taste, turning any glass of bubbly into something a bit more special.Cheers!Cocktail spec: Kir RoyaleScant 1/2 ounce - Crème de Cassis or Crème Yvette (see note)To top - Dry Champagne (or other dry sparkling wine or Prosecco)Garnish: Lemon twistThe process:Pour the creme de cassis into a Champagne flute. Top with the Champagne. Garnish with a lemon twist, and voilà!Notes:* “Scant” here means just a bit less than a ½ ounce, but make them to your taste.* Use of Crème Yvette will add a violet note and lead to a slightly drier Kir. Also wonderful in an Aviation.Please share! There is plenty of room for others at the cocktail party! Please share with your network or workplace today. Thank you!As always, it’s great to have you here! If you enjoyed this episode, please subscribe, share, rate (it helps!), and let us know your thoughts. We love to hear from our listeners.Be well, be safe, and here is to good business! Cheers! - Brian & BillCocktails & Commerce™ is a wholly owned subsidiary of StrategyēM, LLC. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cocktailsand.substack.com

This week Bill and I are joined by Travis Hess, CEO of BigCommerce to mix up a C&C original cocktail with us and talk about BigCommerce - his vision, where BigCommerce fits, contrasting BigCommerce & Shopify, and where the commerce platform and technology market is headed.Travis took the reins at BigCommerce this past September, rising from President to lead the company’s transformation. Travis has an extensive background in commerce, but much of it on the services side including leadership roles at LiveArea, BVA and The Stable, and then Accenture - and was a part of numerous successful exits.It's a lively, fun, and a terrific conversation, so please pour yourself something to sip along with us and enjoy the conversation.Cheers!Episode Chapters:* Cocktail talk: The Gran Comercio Caliente* Hey Kai, understanding BigCommerce* Taking the reins at BigCommerce* Navigating Market Challenges & The Evolving Landscape of E-commerce* The Future of Commerce: Agility, AI, and Composability, and Orchestration* Understanding the Competitive Landscape - Contrasting BigCommerce & Shopify* Building a Strong Team and CultureMore about LALO Tequila LALO is a wonderful, additive-free, artisanal tequila from third-generation tequila makers in Jalisco, Mexico using a time-honored approach. Just cooked and steam rolled agave, then fermented and into the bottle. It’s wonderful, clean and delicious - and we love mixing with it! Find it here.Please subscribe! We want to be sure you make it to the next party and get all of our commerce industry content! Cheers!This week’s cocktail - the Gran Comercio CalienteThis week's cocktail is a C&C original. A riff on a Negroni spec, this is a well balanced cocktail with just a hint of spice. Careful with those spicy bitters!Cheers!Cocktail: Gran Comercia Caliente1 oz - Blanco tequila (LALO Tequila Blanco recommended).75 oz - Campari.5 oz - Palo Cortado Sherry (substitute Amontillado sherry or Cream Sherry).5 oz - Ancho Reyes Chile liqueur2 drops - Tres Amigos cocktail bitters by Infused Bitters or Bitterman’s Hellfire cocktail bittersThe process:Add ingredients to a cocktail mixing glass, add ice, and stir until well chilled (~30 seconds). Strain into a rocks glass or coupe. No garnish.Please share! There is plenty of room for others at the party! Thank you!As always, it’s great to have you here! If you enjoyed this episode, please subscribe, share, rate (it helps!), and let us know your thoughts. We love to hear from our listeners.Be well, be safe, and here is to good business! Cheers! - Brian & BillCocktails & Commerce™ is a wholly owned subsidiary of StrategyēM, LLC. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cocktailsand.substack.com

Welcome everyone to another episode of Cocktails & Commerce. This week Kiri Masters joins us to mix up a ‘Walk in the Park’ mocktail and talk about the world of retail media and how it is poised to change quickly.Kiri was the founder of Bobsled Marketing, an agency focused on helping marketplace sellers with their strategy to compete and gain exposure. Bobsled was acquired in 2022, and Kiri is now host of the ‘Retail Media Breakfast Club’ - a daily podcast and newsletter focused on the retail media landscape. She is also a contributor to Forbes.Please pour yourself something to sip along with us and enjoy the conversation.Chapters:* Introduction and the ‘Walk in the Park’ mocktail * Hey Kai, Retail Media * The Fractured Retail Media Landscape* The Dominance of Amazon and Walmart* Brands' Perspectives on Retail Media Spending* Technology Solutions in Retail Media* Impact of Retail Media on the eCommerce Customer Experience* The Future of Retail Media Advertising* Evolving eCommerce Experiences and the impact of Agentic agents on Retail Media + The Role of Loyalty Programs in AI Shopping* Some Personal Insights from life in ThailandThe Walk in the Park mocktail:1 ½ ounces mango puree¼ ounce simple syrup (1:1)½ ounce fresh orange juice½ ounce fresh lime juiceGarnish - slice of mango & mint sprigSteps:Add ingredients to a cocktail shaker, add ice, and shake vigorously until chilled. Strain in a cocktail coupe or other cocktail glass This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cocktailsand.substack.com

This week Bill and I are joined by Rick Nash, Founder & CEO of Spotlight, to mix up a Horsefeather from Rick’s hometown of Kansas City, and talk about analyst relations and how to think about that.Spotlight is among the leading analyst relations firms that help technology and services companies with analyst relations strategy and execution.I’ve had the pleasure of knowing Rick for many years, from way back when I was an analyst to later, as a customer of Spotlight - it was great to reconnect and have him on the show.So please pour yourself something to sip along with us and enjoy the conversation.Cheers!Episode Chapters:* Intros exploring the Horsefeather* Hey Kai, understanding Analyst Relations* The Birth of Spotlight and Rick’s Founder's Story* Engaging analysts in new categories* Misconceptions of Analyst Relations* The Evolution of analyst firms with influencers and thought-leaders (asking for a friend)* Strategic AR steps for startups* A few personal reflectionsPlease subscribe! We want to be sure you make it to the next party! Cheers!This week’s cocktail - the HorsefeatherThe Horsefeather is a lesser-known yet highly enjoyable variation of the classic buck cocktail, a family of drinks that combine a spirit, citrus, ginger beer (or ginger ale), and sometimes bitters. Bucks, also known as mules, gained widespread popularity in the early 20th century, particularly with the rise of the Moscow Mule in the 1940s. The Moscow Mule, a simple but effective blend of vodka, lime, and ginger beer, was born out of marketing necessity—a joint effort by John G. Martin, who was struggling to sell Smirnoff vodka in the U.S., and Jack Morgan, who had a surplus of ginger beer at his L.A. bar. Served in copper mug that Morgan also had a surplus of, the drink took off with the Hollywood crowd and cemented the mule (or buck) as an entire cocktail category.While the Moscow Mule put bucks in the limelight, the family of drinks long predates it. The Kentucky Mule (with bourbon), Mexican Mule (with tequila), and London Mule (with gin) all follow the same template, allowing the base spirit to shape the drink’s profile. The buck itself dates back to the 19th century, when drinks like the Horse’s Neck (a ginger and bitters-based highball) laid the groundwork. The defining characteristic of a buck is its balance between spice, sweetness, and acidity, making it a refreshing and versatile template for bartenders to play with.The Horsefeather mule variation originated in Lawrence, Kansas, sometime in the 1990s, making it a relatively modern entry in the buck lineage. It swaps vodka for rye whiskey, adding Angostura bitters for depth and complexity. The result is a spicier, more robust take on the mule—where the peppery bite of rye and the warmth of ginger beer complement each other very well. Often served in a highball glass over ice, the Horsefeather remains a regional favorite in the Midwest, though its appeal is slowly spreading beyond Kansas. Its name, while whimsical, remains a bit of a mystery, but like many great cocktails, its charm lies in its balance of the simple and the bold. Cheers!Horsefeather Cocktail Spec (Serves one)Absinthe, to rinse1.5 oz (~45ml) - Rye whiskey or bourbon4 oz (~30ml) - Ginger beer (Fevertree recommended)4 dashes - Angostura bittersGarnish - Lemon wedgeThe process:Add a bunch of ice to a tall Collins or highball glass, add ingredients and stir. Express lemon wedge, stir again and enjoy.Thanks for reading Cocktails & Commerce! This post is for everyone, so feel free to share the party!As always, it’s great to have you here! If you enjoyed this episode, please subscribe, share, rate, and let us know your thoughts. We love to hear from our listeners.Be well, be safe, and here is to good business! Cheers! - Brian & BillCocktails & Commerce™ is a wholly owned subsidiary of StrategyēM, LLC. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cocktailsand.substack.com

This week Bill and I are joined by Jamie Anderson, President of UserTesting, to mix up a legendary Scottish cocktail - the Bobby Burns - and talk about the importance of customer feedback, testing, and balancing qualitative and quantitative customer input. We also touch on Jamie’s unique career journey from engineer into sales, then into marketing, sales leadership to today as President at UserTesting.Jamie has an impressive, and unique background - including his time as a rock musician fronting Scottish band Big Wednesday before moving into software - with stops at Siebel, SAP, Marketo, Xcactly, and now UserTesting - the market leader in usability and a solution provider uniquely able understand human reactions to digital experiences at scale.We’ve had the pleasure of knowing Jamie for many years, including working closely together at SAP. It was great to reconnect and have him on the show.So please pour yourself something to sip along with us and enjoy the conversation.Cheers!Episode Chapters:* Intros and exploring the Bobby Burns cocktail* Hey Kai, understanding UserTesting* The value of customer feedback* Leveraging AI at User Testing* Democratizing research and insights* Journey to leadership: A personal evolution* Comparing GTM across global software markets* The impact of AI on sales and marketing* Scotland's tech scene: Talent and opportunities* The musician's journey: Lessons in resilience and connectionPlease subscribe! We want to be sure you make it to the next party! Cheers!This week’s cocktail - the Bobby BurnsThe Bobby Burns cocktail is a sophisticated classic that pays homage to Scotland’s national poet, Robert Burns. This elegant mix of Scotch whisky, sweet vermouth, and Bénédictine is a close cousin to the Rob Roy but with a unique herbal twist. Its origins trace back to early 20th-century cocktail culture, appearing in various forms in classic bartending guides like The Savoy Cocktail Book. The drink is a perfect example of how Scotch, often seen as a sipper, can be transformed into a well-balanced cocktail with depth and complexity.Much like the Rob Roy, which is essentially a Scotch-based Manhattan, the Bobby Burns follows a similar formula but substitutes a portion of the vermouth’s sweetness with Bénédictine, a French herbal liqueur. This small addition brings a layered, botanical quality that distinguishes it from its better-known counterpart. Some early versions of the cocktail even called for absinthe or Drambuie instead, but Bénédictine ultimately became the defining element of the drink. It adds a nuanced, honeyed herbal character that plays beautifully with the smoky, rich notes of the blended Scotch.Bénédictine itself is an intriguing ingredient, steeped in mystery and history. First created in the 19th century, it’s made from a blend of 27 herbs and spices, giving it a complex, slightly medicinal yet sweet and aromatic profile. When mixed into the Bobby Burns, it rounds out the cocktail with a velvety texture and a hint of spice, making it a perfect sipper for cooler evenings. Whether enjoyed as a toast to poetry or simply as a refined alternative to the Rob Roy, the Bobby Burns is a timeless choice for lovers of Scotch-based cocktails.Cheers!Bobby Burns Cocktail Spec (Serves one)Absinthe, to rinse1 oz (~30ml) - Blended Scotch whisky (Johnny Walker Black Label is a good choice)1 oz (~30ml) - Sweet vermouth (Carpano Antica recommended).5 oz (~15ml) - BénédictineGarnish - Lemon peelThe process:Add the scotch, vermouth and Benedictine to a mixing glass, add ice to cover, and stir until well-chilled. Strain into a cocktail glass. Twist a lemon peel over the glass to release its oils and then drop it into the drink and enjoy!Please share! There is plenty of room for others at the cocktail party! Thank you!As always, it’s great to have you here! If you enjoyed this episode, please subscribe, share, rate (it helps!), and let us know your thoughts. We love to hear from our listeners.Be well, be safe, and here is to good business! Cheers! - Brian & BillCocktails & Commerce™ is a wholly owned subsidiary of StrategyēM, LLC. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cocktailsand.substack.com

This week Bill and I are joined by Scott Silverman, Co-Founder of CommerceNext and long-time commerce community builder, to mix up some classic Sazerac cocktails and talk about the keys to building a vibrant professional community and hosting a great event. We also gain Scott’s perspective on the health and state of the commerce community in the U.S. today.Many of you either know Scott or have seen him on-stage, online, or at an event. Scott joined Shop.org in 1999 and rose to become Executive Director shortly after that, leading that organization as it became a critical part of the National Retail Federation. Scott went on to co-found CommerceNext in 2017, where he continues to drive what is today the most meaningful community of digital commerce leaders in the United States. As we head into (yet another) NRF it was great to connect withI’ve had the pleasure of knowing Scott for many years, and it’s great to have him on the show.So please pour yourself something to sip along with us and enjoy the conversation.Cheers!Note: We recorded this prior to the recent tragedy in New Orleans. We talk about that great city and share experiences we had at Jazz Fest and all the good times we have had in that vibrant, amazing city. Our thoughts are with the people and community impacted by the recent tragedy in NOLA - and unfortunately elsewhere - as we release this episode.Episode Chapters:* Exploring the Sazerac cocktail* Hey Kai, understanding CommerceNext* The post-pandemic commerce landscape* Keys to building meaningful professional communities* Crafting engaging events with solution providers* “Hot or Not” - a run down of commerce and digital marketing trends* NOLA Jazz Fest and the joys of music* Closing thoughts and signature cocktailsPlease subscribe! We want to be sure you make it to the next party! Cheers!This week’s cocktail - the SazeracFew cocktails capture the spirit of a city quite like the Sazerac, the official cocktail of New Orleans. Its history begins in the 1830s, when Antoine Amédée Peychaud, a Creole apothecary, introduced his bitters as a remedy in the city’s burgeoning French Quarter. His creation, a mix of his proprietary bitters, sugar, and Sazerac de Forge brandy gained popularity at a time when medicinal tonics often doubled as recreational libations. Legend has it that Peychaud served his mixture in an egg cup, or “coquetier,” possibly giving rise to the very term “cocktail.” While the origin of the term ‘cocktail’ remains debated, the Sazerac's place in the pantheon of classic cocktails is indisputable.The Sazerac's story took another turn when phylloxera, the 19th-century vine pest that devastated European vineyards, necessitated a shift to rye whiskey - a substitution that gave the drink its spicy backbone and American identity. The addition of absinthe - with Herbsaint substituted during absinthe’s prohibition - introduced a touch of herbal complexity.By the 20th century, the Sazerac was firmly entrenched as a pillar in the canon of cocktails, featured in cocktail books and celebrated in bars across the United States. Its codification as New Orleans’ official cocktail in 2008 cemented its cultural importance, ensuring its legacy endures. The Sazerac is more than a drink—it’s a story of resilience, reinvention, and the enduring charm of New Orleans - embodying the cultural crossroads that is New Orleans, a place to come together.Cheers!Sazerac Cocktail Spec (Serves one)Absinthe, to rinse1 - sugar cube (Demerara recommended)1/2 teaspoon (~2.5 ml) - Cold water4 dashes - Peychaud’s bitters2 1/2 oz (~75 ml) - Rye whiskeyGarnish: lemon peelThe process:Rinse a chilled rocks glass with absinthe, discarding any excess, and set aside. In a mixing glass, muddle the sugar cube, water and the Peychaud’s bitters. Add the rye whiskey, fill the mixing glass with ice and stir for 15­–20 seconds, until well-chilled.Strain into the prepared glass and twist the lemon peel over the drink’s surface to express the peel’s oils, then garnish with the peel.Please share! There is plenty of room for others at the cocktail party! Thank you!As always, it’s great to have you here! If you enjoyed this episode, please subscribe, share, rate (it helps!), and let us know your thoughts. We love to hear from our listeners.Be well, be safe, and here is to good business! Cheers! - Brian & BillCocktails & Commerce™ is a wholly owned subsidiary of StrategyēM, LLC. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cocktailsand.substack.com

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 familyThanks for reading Cocktails & Commerce! Please subscribe! We want to be sure you make it to the next party! Cheers!This week’s cocktail - an AmericanoFirst 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) - Campari1 1/2 oz (~ 45ml) - sweet vermouthSoda water, chilled, to top & tasteGarnish: orange twistThe 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!As always, it’s great to have you here! If you enjoyed this episode, please subscribe, share, rate (it helps!), and let us know your thoughts. We love to hear from our listeners.Be well, be safe, and here is to good business! Cheers! - Brian & BillCocktails & Commerce™ is a wholly owned subsidiary of StrategyēM, LLC. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cocktailsand.substack.com