Pancakes and Booze Art Show Returns
Chicago's underground art scene was on full display as the Pancakes and Booze Art Show returned to Reggies on February 28th. The popular event, known for its vibrant atmosphere, featured work from dozens of emerging local artists alongside free, all-you-can-eat pancakes for attendees.
The Pancakes and Booze Art Show, which started in a small Los Angeles apartment in 2009, has grown into a significant pop-up art event, having hosted over 500 shows in more than 40 cities across North America and Europe. Founder Tom Kirlin's initial idea was to create a more accessible and fun art gallery experience, using free pancakes to draw in crowds for emerging artists who might not fit the traditional gallery model. Platforms are increasingly turning payments from a cost center into a primary revenue driver through "embedded payments." This model involves integrating payment processing directly into their software, allowing them to earn revenue on transactions. Vertical SaaS companies, in particular, can increase customer revenue by a factor of two to five by embedding financial services like payments. Leading platforms like Shopify and Toast have demonstrated the power of this model. Shopify monetizes by charging transaction fees, earning more when merchants use their native Shopify Payments, and even adds fees when merchants use third-party gateways. Similarly, over 80% of Toast's revenue comes from financial services, primarily payment processing and lending. This strategy increases customer stickiness and lifetime value. For platforms not ready to become a full "PayFac" (Payment Facilitator) due to the high costs and compliance burdens, a "PayFac as a Service" (PFaaS) model has emerged. PFaaS allows software companies to offer integrated payments and earn revenue while a third-party provider manages the complexities of risk, compliance, and onboarding. This significantly lowers the barrier to entry for monetizing payments. The push for faster payments is creating new monetization opportunities. Real-time payment networks are seeing massive growth, with transaction volume on the RTP network increasing 28% between late 2024 and late 2025. Platforms can monetize this demand by offering instant payouts for a small fee, bundling faster payments into premium subscription tiers, or using it as a retention tool for high-value users. This shift transforms payments from a simple transaction into a critical part of a platform's value proposition. AI is further revolutionizing payment infrastructure by optimizing everything from fraud detection to transaction routing. AI algorithms analyze vast datasets in real-time to identify anomalies, reduce false declines, and select the most efficient payment processors, lowering costs. For enterprise sales, discussing AI's role in automating compliance, mitigating risk, and personalizing checkout flows demonstrates a forward-looking understanding of payment systems. Moving from mid-market to enterprise sales in the fintech space requires a strategic shift from selling a product to selling a trusted partnership. Enterprise buyers are more sophisticated and the sales cycles are longer, demanding a deep understanding of their business, regulatory needs, and technical stacks. Key metrics for enterprise sales leaders include average contract value (ACV), sales cycle length, and win-rate by vertical. Mastering the enterprise sales cycle involves identifying internal champions, building a compelling ROI case with clear metrics, and proactively addressing compliance and integration risks. Negotiation in this arena is less about discounting and more about creating value; successful negotiators prepare extensively, understand peer pricing benchmarks, and are prepared to walk away. Building a sales team for this market means hiring for deep domain fluency in payments and regulatory frameworks, not just sales acumen.