Verticals: A Weekly Biz Show

Most SaaS founders think scaling sales means hiring more salespeople. Kevin Wilson thinks that's exactly how you get into trouble. Kevin is the CRO of Skimmer, the software platform used by thousands of pool service companies across the US. Before Skimmer, he helped scale multiple vertical software businesses from founder-led sales and pre-revenue stages to tens of millions in ARR. And along t...

Everyone was predicting a SaaSpocalypse. Now the data is coming in... and SaaS isn't dead. Public software has rebounded, vertical software has held up relatively well, infrastructure is surging, and consumption-based businesses are benefiting directly from the explosion of AI usage. So Luke and Nic are asking a different question: What happens next? In this episode of Verticals, there’s no guest....

What if the next great software companies don't look like Salesforce… or even ChatGPT? Dominic Dinardo has spent more than 25 years watching the software industry reinvent itself. He joined Salesforce in 2002, before “cloud computing” was even the term everyone used. He later joined Veeva and learned firsthand why going deep into a single industry could create a completely different and incred...

What happens to marketplaces when buyers and sellers don't need to be human anymore? AI agents are getting increasingly capable of searching, negotiating, purchasing and eventually transacting with other agents. And according to Mike Duboe, General Partner at Greylock, that could completely reshape how marketplaces and commerce itself work. In this episode of Verticals, Luke and Nic sit down w...

Every AI startup wants to get closer to the customer. But what happens when getting closer turns your software company into a services business? In this episode of Verticals, Luke and Nic sit down with Quinn Litherland, founder and CEO of Revin, to explore one of the biggest shifts happening inside AI-native companies: the rise of forward-deployed teams. But there's a catch. Forward-deployed t...

For 50 years, software companies sold tools. But customers never really wanted the tool. They wanted the job done. In this episode of Verticals, Nic sits down with Yoni Rechtman, Partner at Slow Ventures, to unpack why AI is breaking the traditional SaaS model and creating an opportunity that could be orders of magnitude larger. Historically, businesses spent only a fraction of their budgets on so...

What separates the vertical software companies that compound for decades from the ones that eventually stall? Sahill Poddar has a unique dataset for answering that question... In this episode of Verticals, Luke and Nic sit down with Sahil, Co-Founder and CEO of Parafin, the embedded finance infrastructure powering capital products across platforms like DoorDash, Worldpay, and Mindbody. By underwri...

AI isn't just changing startups. It's exposing everything that's broken about venture capital. In this episode of Verticals, Nic sits down with Rick Zullo, Founder and Managing Partner of Equal Ventures, to discuss why today's venture market feels increasingly disconnected from the businesses it's funding, and why some of the biggest trends in AI investing may be driven as much...

AI is making it easier than ever to build software. So why are the best founders spending even more time thinking about what NOT to build? In this episode of Verticals, Nic sits down with Alex Oppenheimer, founder of Verissimo Ventures and former investor at NEA and Morgan Stanley, to discuss how AI is reshaping software, venture investing, and even decision-making for founders. From barbers rebui...

For the last two years, AI has been a race to build the best model. But what happens when the models become cheap, open source, and nearly interchangeable? That's the question reshaping the entire AI industry. In this episode of Verticals, Luke and Nic sit down with Jake Saper, General Partner at Emergence Capital and one of the earliest investors in companies like Zoom, Veeva, Ironclad, and T...

Compliance isn't usually where great software companies start. It's often dismissed as a feature. A checkbox. Something incumbents can easily add later. But in the AI era, that assumption is starting to break. In this episode of Verticals, Nic sits sdown with Zach Rosen, Co-Founder and CEO of Brellium, to explain why compliance can become one of the strongest wedges in vertical AI, if you&...

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...