In this episode of Verticals, Luke and Nic sit down with Nick Tippmann (Founder & Managing Partner, TipTop VC) to break down what’s really happening as AI agents and workflow tools trigger panic across the markets, and where the real value (and money) will accrue over the next 12–24 months.

Nick shares the operator playbook he learned as founding CMO of Greenlight Guru (a bootstrapped vertical SaaS success story) and how it now shapes his investing thesis in vertical AI. They debate AI-native upstarts vs legacy incumbents, why the system of record is still the “oxygen for AI”, and why the most dangerous place to be might be point solutions and broad horizontal tools.

They also go tactical on what’s working right now:

• How the best teams win with distribution + disciplined execution
• Why outcomes-based pricing needs to start with micro outcomes (not giant promises)
• The real moats in an agent-first world: trust, audit logs, permissions, deterministic workflows, and brand

If you’re building, investing, or selling in vertical AI, this is a full-on strategy session.

Today on Verticals, we sit down with Darren Feike, Founder & CEO of Sante, building a complete operating system for wine & liquor stores.

What looks like a niche is actually massive: the US liquor store market is ~$80B, and the average store does ~$2.5M in annual sales, with ~90% of locations independently owned. Darren breaks down why this market has been overlooked, how regulation creates a moat, and the exact playbook Sante used to move customers off legacy systems using AI agents.

We also go deep on:

• Why liquor stores are way more complex than most Main Street verticals
• The “rip and replace” problem — and how Sante makes switching seamless
• Founder-led sales → repeatable outbound at scale
• Building a platform after starting with a wedge product
• What it takes to hit real feature parity and unlock referrals

If you’re building vertical software, embedded fintech, or selling into a regulated market, this one’s a must-watch.

In this episode of Verticals, Luke Sophinos and Nic Poulos sit down with Mike Powers, CEO and Co-founder of BuildVision, to unpack one of the hardest problems in vertical software: how to build and monetise products inside complex, multi-stakeholder ecosystems. Commercial construction isn’t a single-buyer market. Value is split across owners, general contractors, OEMs, reps, and financiers, and traditional SaaS pricing models break quickly in that reality.

BuildVision is taking a different approach: giving away table-stakes software, then monetising on outcomes, where real work is replaced, risk is reduced, and transactions actually flow. Mike brings rare, operator-level perspective. Before founding BuildVision, he worked inside Turner Construction’s strategic procurement arm (scaling over $1B in annual equipment spend), helped build BuildingConnected (acquired by Autodesk), and now serves many of the top general contractors in the US.

We dive deep into what actually works when you’re building vertical AI and software in enterprise environments: why “multiplayer” products matter, how outcome-based monetisation avoids the agency trap, and why the real moat is often data orchestration, not UI.

This episode is a deep, operator-level discussion on the next evolution of vertical SaaS and AI: how decision layers replace traditional systems of record, why free tooling can be a strategic advantage, and how founders can align pricing directly to customer value at scale.

Whether you’re a founder, operator, or investor building or backing vertical SaaS or AI in complex, regulated industries, this episode will fundamentally change how you think about monetisation, product strategy, and go-to-market.

New episodes drop every Wednesday.