The Pitch

Jesse Middleton, seasoned VC with deep fund experience. Jamie Gin Lewis, founder of Wiggle Room building childcare management tools. Celine King, CEO of Greener creating fleet-level carbon accounting. Amaka Uchegbu, founder of Uche AI using barcode scans to inform textured-hair brands. They pitch fast on product, go-to-market, data integrations, revenue models, channel partnerships and scaling plans in rapid-fire conversations.

Marco Benitez, founder of Rook, built an API that integrates and cleans wearable data for insurers and hospitals. Elizabeth Yin, venture investor at Hustle Fund, asks sharp questions and evaluates founder-investor fit. They discuss Rook’s integrations, go-to-market, fundraising dynamics, runway concerns, and the importance of vibe and partner alignment in raising capital.

Elizabeth Yin, a VC investor at Hustle Fund known for direct, no-nonsense feedback, joins the pitchroom. The conversation covers Climatta’s 30-second utility invoice scraper and how it finds billing inefficiencies. They discuss sales tactics that landed pilots like 7-Eleven, the focus on manufacturing customers, and why investors raised concerns about repeatability and venture-scale growth.

Charles Hudson, a venture investor known for sharp PMF and pricing questions, and Joe, co-founder of Minimis building Flow AR smart sunglasses for runners and cyclists, take center stage. They demo a prototype with live stats and navigation. They debate form factor vs. flat glasses, pricing at $699, manufacturing timelines, and market validation after big-tech moves. Tension over fit, weight, and customer targeting fuels the conversation.

A founder with lifelong robot obsession demos VR-powered tools that let anyone teach robots new skills using video and glasses. They discuss making robot training software that works across many robot brands, marketplaces for robot skills, and one-shot transfer from egocentric footage. Conversations cover B2B use cases like warehouses, agriculture, airlines, and the tension between task-specific robots and humanoids.

Meet Jesse Middleton, an investor and recovering CRO who grills go-to-market plans, and Meghan Scanlon, CEO of Aleoop and former enterprise sales leader who turned a lost deal into an AI that mines sales feedback for product signals. They demo Aleoop ingesting Gong, Slack, Jira and CRM data. Conversation covers labeling, integrations, pilot traction, pricing strategy, conversion risks, roadmap priorities, and early fundraising.

Jesse Middleton, venture investor who critiques product-market fit and growth, and Elizabeth Yin, venture investor known for rapid-fire market and speed-to-market questions. They dig into PeachWeb’s AI 3D website builder, the shift from HTML to WebGL, traction metrics and pricing choices, go-to-market spend, and whether immersive, design-forward sites can scale in a crowded website-builder market.

Sarah Lucena, founder and CEO of MAPA, shares her journey in boosting her startup’s valuation from $15M to $48M through savvy negotiation and strategic timing. She discusses her successful fundraising experience with angel investors and VCs. Matt Truby, founder of Above Health, takes on the role of a mad scientist, explaining his innovative approach to acquiring clinics to fuel AI diagnostics and commercialization. Together, they reveal their tactics for creating impactful startups in the competitive health tech landscape.

Curious about starting a venture fund? VCs discuss the journey from small syndicates to building a full-fledged fund. They highlight what makes a pitch irresistible, like unique insights and storytelling. Founders should focus on mission and execution speed to catch investor attention. Also, hear about the biggest companies they regret passing on, including Udemy and Square, sharing valuable lessons. This lively Q&A is packed with insider tips straight from the experts!

Matt Truby, Founder and CEO of Above Health, shares his inspiring journey into the world of allergy and asthma care, motivated by a personal crisis with his daughter. He presents innovative diagnostic devices, a family app for monitoring allergies, and a smart inhaler prototype with GPS tracking. Cyan Banister, the savvy angel investor, probes the business model's complexity and product viability. Together, they explore the challenges of integrating telehealth with hardware, while also discussing strategies for scaling and securing essential partnerships.