2030

How Two Sommeliers Are Disrupting a $90B Industry With Cans [Ft. Zeke Blattler, Los Cuernos Wine]

Zeke Blattler [https://www.linkedin.com/in/zeke-blattler-16384642/], Co-Founder & CEO of Los Cuernos Wine [https://loscuernos.com/], is running a two-person company gunning for a $100-300M exit — and his argument for why that's achievable without a large team is one of the more clear-eyed takes on company building you'll hear. With $90 billion in revenue locked inside glass bottles and an aging consumer base, he saw a structural window most incumbents are too slow to act on. The strategy he and co-founder Cory Assink built to get there is specific, counterintuitive, and worth studying regardless of what industry you're in. Zeke walks Keith through a full first-principles rebuild of the wine supply chain — every distribution, packaging, and placement decision made by working backward from the consumer, not forward from industry convention. He's not pitching wine. He's showing how a two-person operation with fractional resources and a borrowed distribution network is out-maneuvering legacy players sitting on billions in entrenched infrastructure. Topics Discussed: * Rebuilding an entire supply chain from scratch by starting at the shelf and working backward * Targeting beer distributors specifically because they're weakest in wine and strongest in the venues — restaurants, hotels, golf courses — where canned wine actually wins * How two real customer moments (a half-open cork, a forced full-bottle purchase) reveal why wine loses the sale before it's even poured * Surviving a 60% revenue collapse from peak summer to Q4 and what it actually takes to forecast a can-first business * Running 423 accounts with two full-time employees by structuring a 1-to-50 headcount ratio through distributor networks * How incumbent wine companies are using the same regulatory infrastructure built after Prohibition to slow down new entrants * The shift in company valuation signals from headcount growth to profitable, talent-dense efficiency — and why AI accelerates it * Targeting $24M run rate as the entry point to own the premium position in a $10-15B emerging category before competition catches up

How This $2B+ Technology Company is Preparing for the Future [Ft. Elia Wallen, Engine]

Most boards pressure founders to reduce direct reports as they scale. Elia Wallen took the opposite approach: he manages 15 direct reports while growing Engine past 1,000 employees to a $2.1B valuation, and he eliminated the Chief Product Officer role entirely. His logic: additional management layers slow decision-making when speed matters most. When you build talent density and restructure one-on-ones around problem-solving instead of status updates, you can operate with higher spans of control. That philosophy was nearly tested to breaking point. Engine came within weeks of running out of cash before their Series A with Telescope Partners closed. At the time, they had 150-180 employees across two entities. That near-death experience shaped Wallen's rejection of rigid planning. He refuses to create five-year plans, preferring to pivot quickly when new information emerges. Case in point: he publicly declared Engine would never do flights and cars, then reversed the decision weeks later. On AI, they've now automated over 50% of support cases while actually improving customer satisfaction scores—not by replacing people, but by redeploying them to higher-value work as the company doubles annually. Topics discussed: * Managing 15 direct reports by focusing one-on-ones on unblocking problems and identifying blind spots * Operating without a Chief Product Officer to eliminate layers between product teams and customers * Nearly running out of cash weeks before Series A closed despite previous successful exits * Understanding valuation multiples: 30x in 2021 versus 9-10x in 2024 makes growth more substantial than surface numbers suggest * Prioritizing will over experience when hiring to find people still hungry to prove themselves * Automating 50%+ of support cases with AI while improving satisfaction by overcoming legacy system skepticism * Deploying AI internally first for faster iteration with immediate feedback before customer-facing rollout * Building personalization and voice/chat interfaces for travel instead of traditional search experiences * Establishing talent density before removing rules to enable Netflix-style freedom and responsibility * Actively deleting processes and bureaucracy to keep the organization young despite reaching scale