Verticals: A Weekly Biz Show

Every AI startup wants to disrupt the incumbents. But what if the companies with the biggest advantage are the ones that already own the data? In this episode of Verticals, Luke and Nic sit down with Adam Harris, Co-Founder and CEO of Cloudbeds, a hospitality platform operating in 157 countries that processes more than $20 billion in transactions. After nearly 14 years building one of the industry...

For years, software companies followed the same blueprint: Raise venture capital. Hire aggressively. Sell SaaS subscriptions. Scale headcount alongside revenue. But AI is rewriting those rules. In this episode of Verticals, Luke and Nic sit down with Zain Jaffer, who previously built Vungle into a business that was acquired for $780M before later reaching a $4B public valuation. After investing in...

When ChatGPT launched, investors had a simple answer for most AI startups: "It's just a GPT wrapper." But what if the biggest winners weren't the model companies? What if the real opportunity was building products that deeply understood a specific customer, workflow, and industry? In this episode of Verticals, Luke and Nic sit down with Adeel Khan, Founder and CEO of MagicSchool,...

Most founders think investors are looking for the perfect idea. They're not. At the earliest stages, investors are really trying to answer a much harder question: Is this founder capable of building something extraordinary? In this episode of Verticals, Luke and Nic sit down with Dan Teran and James Gettinger of Gutter Capital to unpack exactly how they evaluate founders before there's mea...

For years, venture capital forced founders into boxes. You were either a consumer company or an enterprise company. But some of the biggest companies in the world never followed those rules. Today, the line between consumer and enterprise is becoming harder to see… and AI may be accelerating that shift. OpenAI, Anthropic, and Google are moving faster than anyone expected. And for many startups, th...

The biggest problem in AI isn't building the product. It's staying relevant six months later. Models improve every month. New competitors appear every week. And switching costs are lower than most founders want to admit. So what actually creates a moat? In this episode of Verticals, Luke and Nic sit down with Kyle Lui from Bling Capital to break down the new rules for product-market fit, m...

Everyone thinks AI will change software through chat. But the biggest shift might actually happen through voice. Because when humans stop typing and start talking to AI naturally, the amount of context, emotion, and real-world data flowing into software explodes. And that changes everything. In this episode of Verticals, Mike Droesch from Bessemer Venture Partners breaks down why voice AI is becom...

Everyone wants to build an AI company right now. But most founders are asking the wrong question. The real challenge isn’t building AI.It’s building something defensible once everyone else has access to the same models. In this episode of Verticals, the tables turn. Nic joins Vignesh Ravikumar and Brendon Schmidt from Sierra Ventures for a deep dive into what it actually takes to build and invest...

In high-stakes industries, 99% accurate is the same as wrong. That last 1% is the entire business. In renewable energy, a single mistake can delay projects by months… or kill them entirely. That’s exactly what Jacob Sandry saw while deploying over $3B into renewable energy projects at Goldman Sachs. 60% of projects were delayed. 30% were canceled altogether. Not because the technology didn’t work…...

If AI can do the work… why are we still valuing software like it only sells tools? And if the real opportunity isn’t software (but labor) are we about to underestimate the biggest companies of this cycle? In this episode of Verticals, Luke and Nic sit down with David Haber, General Partner at Andreessen Horowitz, to break down why vertical AI is fundamentally changing how businesses are built, and...

Everyone says SaaS is dead. Public software stocks are down. Multiples are collapsing. And AI is coming for everything. But what if that’s not the full story? In this episode of Verticals, Nic sits down with Morgan Livermore, Founder of Supercruise Capital, to break down what’s actually happening in the software market, and where AI fits into it. Morgan explains why SaaS multiples have dropped bel...

When’s the last time you thought about laundromats? Probably never. But behind the scenes, this “boring” industry is quietly making BILLIONS of dollars every year... still running on coins, legacy systems, and almost no modern software. That’s exactly what Alex Jekowsky saw. After selling his first company, he went looking for a simple SMB investment… and instead found one of the biggest untapped...

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 A...

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...

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...

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...

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 eliminati...

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...

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 vertic...

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 crea...

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 tr...

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 ins...

In this episode of Verticals, Luke Sophinos and Nic Poulos sit down with Nate Baker, founder and CEO of Qualia and creator of Fractal, to unpack one of the most controversial questions in modern SaaS: Is TAM actually too small - or are we asking the wrong question entirely? Nate has built one of the most important systems of record in real estate, serving over 500,000 professionals, and has helped...

In this episode of Verticals, Luke Sophinos and Nic Poulos sit down with Scott Wolf, founder and former CEO of Levelset, to unpack what it really takes to build and exit a vertical SaaS company, including Levelset’s ~$500M acquisition by Procore.   Scott’s background is unusually eclectic: entrepreneurial roots, early software tinkering, a short stint as a lawyer, and a front-row seat to the const...

In this episode of Verticals, Luke Sophinos and Nic Poulos sit down with Rahul Hampel, GM & VP of FinTech at ServiceTitan, to break down what embedded finance actually looks like when it’s done right, and where most vertical SaaS founders go wrong.   Rahul has built and scaled fintech platforms at Plaid, Yelp, and now ServiceTitan. He’s seen companies 3–5x revenue per customer by layering in p...