Verticals: A Weekly Biz Show

How AI Startups Are BEATING Billion Dollar Companies (Vertical AI Playbook)

What does it actually take to beat a billion-dollar incumbent? Not just compete with them, but WIN.
Most industries today are still dominated by legacy software: Expensive. Slow to innovate. And often deeply hated by their customers.
But that’s starting to change.
In this episode of Verticals, Luke and Nic sit down with Alex Niehenke, Partner at Scale Venture Partners, to break down how vertical AI startups are going head-to-head with the incumbents (and where they actually have an advantage).
Alex shares why “boring” industries are suddenly the most exciting opportunities in tech, how founders can compete with companies worth billions, and how pricing, defensibility, and distribution are all being rewritten in real time.
If you are building, investing, or thinking about vertical AI, this is a clear look at how the game is actually being played today.

The Playbook for Building Vertical SaaS (10 Years of Hard Lessons) | Andres Robelo

This business started with a simple frustration.
Waiting an hour… just to play tennis.
No booking system. No software. Just pen and paper in 2016.
Most people would complain and move on, but Andres Robelo decided to build something.
In this episode of Verticals, Luke and Nic sit down with Andres Robelo, Founder and CEO of Play By Point, to break down how a simple idea turned into a global vertical SaaS company powering over 1,000 racket sports clubs across 37 countries.
Andres shares how he made every mistake early, from choosing the hardest possible first customer (government contracts) to picking the wrong initial wedge, and how those lessons shaped the product into a true end-to-end operating system for clubs.
They also explore the deeper shift happening in vertical SaaS today:
-Why your product can be rebuilt overnight in the AI era-Why trust and customer relationships are the real moat-How small, overlooked industries can become massive opportunities
If you are building, investing, or thinking about vertical SaaS, this is a real look at what it actually takes (over years, not months).
 
TIMESTAMPS
00:00 Intro01:00 From booking courts to building a full OS03:09 9 months to land the first customer (and why it mattered)05:00 Scaling to 1,000 clubs across 37 countries12:38 Why small product details make or break vertical SaaS16:33 Why trust is the real moat in AI23:11 The 10-Year Playbook (No shortcuts)37:58 What Most Founders Get Wrong About Monetization52:31 Andres’ Advice to founders
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Insurance Companies Don't Want This AI To Exist... | Episode 22

Everyone says AI will replace doctors, automate care, and transform healthcare.
But what if the biggest opportunity isn’t in care at all... but in fixing how healthcare actually gets paid?
The claims. The denials. The endless back-and-forth between providers and insurance companies.
In this episode of Verticals, Luke sits down with Christophe Rimann, Founder and CEO of Camber, to break down how AI is quietly fixing one of the most broken systems in healthcare, and unlocking millions in lost revenue for clinics across the country.
Chris shares how his journey from early crypto to McKinsey led him into healthcare’s revenue cycle problem, and why the real opportunity wasn’t building another SaaS tool, but building a system that actually gets providers paid.
They discuss how Camber rebuilt the claims process from the ground up, why most providers only collect 90% of what they’re owed, and how AI can push that closer to 95%+ without adding more humans.
They also explore the deeper shift happening in AI and vertical software:
-Why outcomes matter more than software in complex industries-Why the future looks more like Stripe than traditional SaaS-Why change management is the real bottleneck in AI adoption-How to win deals by proving ROI in 60-90 days
If you are building, investing, or operating in AI, this is a real look at where AI actually works, and what it takes to turn it into a durable business.
 
TIMESTAMPS:
00:00 Intro00:40 From crypto to fixing a broken healthcare system03:07 Why clinics don’t collect all the money they’re owed06:24 The “long tail” problem costing providers MILLIONS09:13 Staying in stealth while building a real AI system12:02 Why you can’t build this on top of legacy software14:23 How AI went from impossible to obvious 22:03 From 85% to 95%: how AI increases collections24:41 Building SaaS-level margins without offshoring30:04 Selling outcomes, not software34:08 What keeps Chris up at night in an AI-first world40:18 The real AI moat49:41 The BIG vision for Camber
If you enjoyed this episode, drop a comment and hit subscribe so you don’t miss what’s next!

AI Agents Are Failing... Here's What Actually Works | Episode 21

Everyone says AI agents are the future.
But what if most of them… don’t actually work?
Not because the tech is bad, but because the way they’re being sold is completely wrong.
In this episode of Verticals, Nic sits down with Deepak Chhugani, Founder and CEO of Nuvocargo, to break down why the real opportunity in AI isn’t selling tools or agents, it’s selling outcomes.
Deepak shares how he built an $85M logistics company by focusing on results over software, and why most AI startups are struggling with retention, change management, and real-world complexity. They unpack what actually happens when you try to deploy AI inside messy, legacy systems, and why most approaches fall apart at scale.
 
They also explore the deeper shift happening in AI and services:
-Why selling AI agents alone isn’t a defensible strategy-How outcomes-based models outperform traditional SaaS-Why embedding into workflows matters more than building tools
 
They also go tactical on what is working right now:
-How to win customers by proving value (not pitching AI)-Why change management is the biggest hidden bottleneck-How to structure pricing to capture value over time
 
If you are building, investing, or operating in AI, this is a real look at what works beyond the hype, and what it actually takes to build a lasting company.
 
TIMESTAMPS:
00:00 Intro01:18 From Wall Street to building an $85M logistics company11:13 Finding the wedge: from simple freight to full supply chain control13:56 The truth about AI agents: why most are failing16:14 Selling outcomes vs selling software19:42 Where real defensibility is built29:57 The biggest mistake founders make35:45 From AI skeptics to AI obsession42:18 The AI agent landscape: what’s working, what’s not, and what’s hype45:40 What actually matters for AI companies

This Startup Is Killing Spreadsheets with AI | Episode 20

Everyone says AI will replace humans.
But what if the biggest unlock isn’t replacing people at all… it’s removing the invisible work they’re buried under?
The spreadsheets. The back-and-forth emails. The manual processes no one sees, but everything depends on.
In this episode of Verticals, Luke and Nic sit down with Chris Hladczuk, Founder of Hanover Park, to break down how AI is quietly eliminating the most boring, painful layer of work in finance, and what that unlocks on the other side.
Chris shares how his experience across Goldman Sachs, fintech, and scaling a company from 10 to 1,000 customers led him to build Hanover Park, an AI-native fund administration platform combining ERP, agents, and human expertise. They dive into why fund data is stale by design, why accuracy is non-negotiable, and why the winning model isn’t pure AI, but AI prepare + human review.
If you are building, investing, or operating in AI, this is a glimpse into what the next generation of companies will actually look like.
 
TIMESTAMPS
00:00 Intro00:56 From Goldman banker to building a $15B AI platform02:10 The Hidden Chaos of Fund Admin06:38 Why Trust is The Hardest Problem in AI11:47 “B2B SaaS Is Dead”... And What Replaces It Next14:43 Why Bundling WINS in AI18:36 How Hanover Park Scaled From $1B to $15B 30:53 The AI Playbook That Actually Works39:26 The Future of Software46:54 The Biggest Lessons for Founders

The New Moat That’s Driving Returns in Vertical SaaS

In this episode of Verticals, Luke and Nic sit down with Dave Pandullo and Scott Hoch, General Partners at Frontier Growth and founders of AQL Growth, to unpack where defensibility, and returns, are really coming from in vertical SaaS.
 
The conversation centres on why being a system of record is no longer enough, and how the next wave of value is being created by systems of action, platforms that don’t just store data, but drive decisions, workflows, and execution.
 
Dave and Scott share how they think about:
Where the real moats are emerging in vertical SaaS and vertical AI
Why some systems of record are now at risk
How execution, workflow ownership, and context create defensibility
What “right to win” actually looks like in niche verticals
How capital-efficient, growth-stage companies generate strong returns
They also go inside how they’re using AI internally to rethink sourcing, diligence, and decision-making, including building an internal system that encodes investment judgment at scale.
If you’re a founder, operator, or investor building in vertical SaaS or vertical AI, this episode breaks down what’s changing, what still matters, and where the next layer of value is being created.

Is Vertical SaaS Breaking? Where AI Actually Creates Massive Value | Episode 18

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.

The Sneaky $80B Market: Why Liquor Stores Are the Ultimate Vertical SaaS Play

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.

The $1.5B Vertical SaaS Opportunity Most Founders Miss with Mike Powers | EP 16

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.

How Michael Saltzman Built EvolutionIQ to Win in Enterprise AI | Ep 15

In this episode of Verticals, Luke Sophinos and Nic Poulos sit down with Michael Saltzman, co-founder and co-CEO of EvolutionIQ, to unpack one of the biggest misconceptions in enterprise AI: Is adoption slow because the technology isn’t ready,or because the enterprise vertical AI playbook hasn’t been written yet?
 
EvolutionIQ is one of the first vertical AI companies to truly break through in insurance, augmenting claims decision-making inside large carriers where even small accuracy gains compound into huge financial impact at scale, culminating in a $750M exit and one of the earliest breakout outcomes in vertical AI.
 
We dive deep into what actually works when you’re selling and deploying AI into 10,000-person organisations: why augmentation beats automation in high-stakes workflows, how EvolutionIQ avoided getting trapped by legacy core systems, and what it takes to prove ROI fast enough to expand across an enterprise.
 
This episode is a deep, operator-level discussion on enterprise vertical AI: how to win adoption from frontline teams, why founder-led sales matters for longer than most people think, and why first-year revenue is often a terrible barometer for building a durable business.
 
Whether you’re a founder, operator, or investor building or backing vertical AI in regulated, complex industries, this episode will fundamentally change how you think about enterprise adoption, product strategy, and go-to-market.
New episodes drop every Wednesday.