Verticals: A Weekly Biz Show

Luke Sophinos
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A VC and a Founder intellectually spar on Vertical Tech & AI: covering the latest news, unpacking in-depth business strategies, and interviewing world-class leaders in the space, every Thursday.

  1. Oct 28

    Most AI Startups Won't Survive (Here's How to Build One That Does) | Keith Rabois

    What happens to your AI startup when OpenAI or Anthropic can suddenly do everything your product does? For Keith Rabois, that's one of the most important questions founders should be asking. Keith is a managing director at Khosla Ventures and one of Silicon Valley's best-known investors and operators. He's backed vertical AI companies including Spellbook, Rogo and Basis, but he believes there's a fundamental difference between building a fast-growing AI product and building a company that can survive for decades. In this episode of Verticals, Luke and Nic sit down with Keith to unpack which vertical AI companies will actually win, which ones are vulnerable to frontier labs, and how the rules of building an enduring software business are changing. They discuss: -Why autopilot AI companies may be more defensible than copilots -How to build an AI startup that benefits from improving foundation models -Why some application-layer companies risk being swallowed by frontier labs -The opportunity to automate entire departments, not just individual tasks -Why Keith believes founders should build for 2030 rather than optimise for today's growth -How AI-native services could reshape accounting, HR and other industries -Why Keith has changed his mind about enterprise investing -Why Keith is bearish on most AI roll-ups -Why legacy vertical SaaS companies could struggle to survive the AI transition 👉 FOLLOW KEITH RABOIS LINKEDIN ➡️ https://www.linkedin.com/in/keith 👉 FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ 👉 FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ 🎬 TIMESTAMPS: 00:00 Keith Rabois on the future of vertical AI 05:03 How AI saved $21M in legal fees 08:03 Why Rogo is winning in investment banking 09:53 Can vertical AI survive the frontier labs? 15:30 Why AI could automate entire departments 19:00 Why fast growth doesn't guarantee survival 25:10 Why Keith changed his mind on enterprise investing 28:06 The new AI go-to-market playbook 33:34 Are AI startup valuations becoming unsustainable? 36:44 How Keith thinks about market size and venture returns 38:50 Why ownership still matters in venture capital 40:50 Why Keith is bearish on AI roll-ups 42:00 Why legacy vertical SaaS is in trouble 45:10 Keith's prediction for the future of podcasts TOPICS 1. Vertical AI, AI Agents & Future of SaaS 2. Keith Rabois, Khosla Ventures & AI Investing 3. AI Defensibility, Frontier Models & Proprietary Data 4. Enterprise AI, Founder-Led Sales & Go-to-Market 5. AI-Native Services, AI Roll-Ups & SaaS Disruption

  2. Oct 21

    AI Is Making Small Markets Worth Billions (Here's How to Build One) | Joel Moreau

    What if the next billion-dollar AI company is hiding in a market most VCs think is too small? For decades, software investors have evaluated startups based on how much customers are willing to spend on technology. But AI is changing that equation. When software can actually perform work (and not just help people manage it), the opportunity extends far beyond traditional SaaS budgets. In this episode of Verticals, Luke Sophinos and Nic Poulos sit down with Joel Moreau, Co-Founder of Mallard Bay, a vertical SaaS and AI platform serving approximately 600 hunting outfitters, fishing charters, and outdoor experience operators across North America. It's an industry where some customers have never joined a Zoom call, where business owners spend their days in boats or trucks, and where traditional software has historically struggled to gain traction. But Joel sees an enormous opportunity. They discuss: - Why AI could make overlooked markets dramatically more valuable - How traditional SaaS budgets are giving way to labor and outcome-based pricing - Why low-tech industries may be ideal markets for vertical AI - How Mallard Bay reduced some customer onboarding times from weeks to 15 minutes - How founders can defend their businesses when competitors can build software faster than ever - How Facebook ads, connected TV, trade shows, and industry associations can unlock difficult-to-reach customers - How AI is changing travel discovery, search, and customer acquisition Joel also shares the unconventional go-to-market tactics that helped Mallard Bay break into an industry where traditional software sales methods often fail. If you're building or investing in vertical AI, SaaS, or technology for traditionally underserved industries, this episode challenges how you think about market opportunity, pricing, distribution, and defensibility. 🎟️ TICKETS DROPPED. Vertical Software Summit — 5-billion-dollar Vertical AI CEOs confirmed to speak. Snag a ticket before they're gone: https://verticalsaasgroup.com/conference 👉 FOLLOW JOEL MOREAU LINKEDIN ➡️ https://www.linkedin.com/in/joel-moreau-b69b791a6 👉 FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ 👉 FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ 🎬 TIMESTAMPS: 00:00 Why AI is making small markets much bigger 02:08 Building software for customers who barely use technology 10:01 How to build a moat beyond your product 18:40 Why AI is changing what customers will pay 21:27 How AI changes the way founders calculate TAM 23:20 Are VCs overlooking niche AI markets? 28:49 Why venture capital is splitting into two markets 36:29 How to sell software to low-tech industries 39:49 Why connected TV ads are working for Mallard Bay 43:20 The unconventional go-to-market playbook behind FareHarbor 47:48 How AI is changing travel discovery and advertising 51:06 Why human taste still matters in AI-generated marketing 52:47 Creative customer acquisition and retention tactics TOPICS 1. Vertical AI & Small Market Opportunities 2. AI Agents, Labor Automation & Outcome-Based Pricing 3. Vertical SaaS, TAM & Venture Capital 4. Go-to-Market Strategies for Low-Tech Industries 5. AI Business Models, Defensibility & Market Expansion

  3. Oct 15

    What Happens When AI Can Copy Your Software? | Coyne Lloyd

    What happens to your software company when a competitor can rebuild your entire product over a weekend? For vertical SaaS founders, that question is becoming increasingly difficult to ignore. In this episode of Verticals, Luke sits down with Coyne Lloyd, founding team member at SnapDocs, former partner at Fractal, and co-founder of multiple vertical software businesses, to explore what actually makes a software company defensible in the age of AI. At SnapDocs, Coyne helped build a business that could charge 5-10 times more than competing products, not because its code was impossible to replicate, but because competitors couldn't easily reproduce its marketplace, proprietary data, and network effects. Now, as AI makes software development dramatically cheaper, Coyne argues that founders need to rethink what they're actually building. They discuss: - Why AI is eroding software complexity as a competitive advantage - The thought experiment every vertical SaaS founder should run - How SnapDocs built defensibility through marketplace dynamics and proprietary data - Why hardware lock-in might be overrated - Why AI could make industry-specific operational knowledge more valuable - The flood of new competitors coming for vertical software markets - Coyne's bullish and bearish predictions for public vertical SaaS companies If you're building, operating, or investing in vertical SaaS or AI, this conversation offers a framework for figuring out which businesses will survive, and which could become more valuable than ever. 🎟️ TICKETS DROPPED. Vertical Software Summit — 5-billion-dollar Vertical AI CEOs confirmed to speak. Snag a ticket before they're gone: https://verticalsaasgroup.com/conference 👉 FOLLOW COYNE LLOYD LINKEDIN ➡️ https://www.linkedin.com/in/numismatist 👉 FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ 👉 FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ 🎬 TIMESTAMPS: 00:00 Intro 03:07 Why vertical SaaS founders are panicking about AI 05:12 How SnapDocs charged 5-10x more than competitors 08:43 The thought experiment every SaaS founder needs 09:29 Why hardware lock-in is an overrated moat 13:14 How SnapDocs built its marketplace and data moat 19:09 Can proprietary AI workflows create process power? 21:56 Why your biggest AI threat might not be OpenAI 29:32 Should SaaS founders sell their proprietary data? 32:33 Will AI destroy embedded software businesses? 38:58 Can startups beat incumbent vertical SaaS companies? 45:49 Why software graveyards are ideal rollup markets 49:24 What Coyne got wrong about AI rollups 52:14 Should vertical SaaS price on outcomes? 54:48 The private vertical software company Coyne is bullish on TOPICS 1. AI Moats, Proprietary Data & Network Effects 2. Vertical SaaS, AI Disruption & Future of Software 3. AI Startups, Vibe Coding & Software Competition 4. AI Rollups, Embedded Software & Vertical AI Business Models

  4. Oct 7

    Why Voice AI Is About to Change Every Vertical | Mike Sharp

    Voice AI is getting dramatically better. But simply adding an AI receptionist to your product isn't going to create a moat. In this episode of Verticals, Luke and Nic sit down with Mike Sharp, founder and CEO of DialStack, to unpack what the next wave of voice AI actually looks like, and why vertical software companies may have a unique opportunity to own it. Mike has spent roughly two decades at the intersection of telecom and SaaS. He previously co-founded Jive Communications, grew it to roughly $100 million in ARR, and later worked inside a healthcare software rollup with 17 brands. Those experiences led him to a simple conclusion: the phone is still one of the most important (and most underutilized) surfaces in vertical software. Mike explains how voice AI can evolve from answering missed calls to routing customers, completing transactional workflows, assisting employees in real time, automatically documenting conversations, and eventually becoming an entirely new interface for vertical software. In this episode, they discuss: -Why every vertical SaaS company should be thinking about voice AI -Where the real moat in voice actually lives -Why simply adding an AI receptionist isn't enough -The voice AI use cases that are actually working today -Why consumers hate some AI agents but love others -When AI should replace humans—and when it shouldn't 🎟️ TICKETS DROPPED. Vertical Software Summit — 5-billion-dollar Vertical AI CEOs confirmed to speak. Snag a ticket before they're gone: https://verticalsaasgroup.com/conference 👉 FOLLOW MICHAEL SHARP LINKEDIN ➡️ linkedin.com/in/mikesharp 👉 FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ 👉 FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ 🎬 TIMESTAMPS: 00:00 Intro 03:29 Why vertical SaaS should own the phone 11:32 The voice AI use cases actually working today 23:00 The overlooked opportunity in ambient voice AI 28:32 Why voice AI is harder than text AI 40:07 Why vertical SaaS hasn't fully embraced voice yet 47:00 Why vertical-specific voice AI could win 51:20 The most interesting voice AI use cases 54:36 Where the next voice AI boom could happen TOPICS 1. Voice AI & AI Agents 2. Vertical AI & Vertical SaaS 3. Embedded Voice & Telephony Infrastructure 4. AI Agents, Ambient AI & Business Automation 5. Proprietary Data, AI Moats & Systems of Record

  5. Sep 30

    How to Build a Vertical SaaS Sales Machine | Kevin Wilson

    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 the way, he's developed a very different playbook for selling vertical software. In this episode of Verticals, Luke sits down with Kevin for a tactical masterclass on vertical go-to-market – where the traditional SaaS sales playbook works, where it breaks, and what founders should do instead. Kevin explains why he almost never recommends hiring 10 sales reps immediately after raising a round. Instead, he hires in groups of two or three, watches the underlying economics, and scales only when the existing motion proves it can support more people. But hiring is only part of the equation. Kevin breaks down exactly what he looks for in sales leaders and AEs, why industry experience is dramatically overrated in sales, and the interview tests he uses to identify great candidates before they join. They cover: -When a startup is actually ready to scale sales -Why founders shouldn't outsource go-to-market fit -Why Kevin always hires sales reps in groups of two or three -The metrics he watches before adding more headcount -Why founders should never completely leave the sales process -How to hire your first great Head of Sales -The four traits Kevin looks for in every AE If you're a vertical SaaS or vertical AI founder trying to go from founder-led sales to a repeatable go-to-market machine, this episode is packed with tactics you can actually use. 🎟️ TICKETS DROPPED. Vertical Software Summit — 5-billion-dollar Vertical AI CEOs confirmed to speak. Snag a ticket before they're gone: https://verticalsaasgroup.com/conference 👉 FOLLOW KEVIN WILSON LINKEDIN ➡️ https://www.linkedin.com/in/kevinwilsonsales 👉 FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ 👉 FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ 🎬 TIMESTAMPS: 00:00 Intro 01:53 Kevin's path from banking to vertical SaaS 06:59 When are you actually ready to scale sales? 08:41 Why hiring 10 AEs at once almost never works 10:31 Why founders should never completely leave sales 16:07 How to hire a great Head of Sales 25:21 The 4 traits Kevin looks for in every sales rep 29:16 Why industry veterans often fail in sales 34:40 Can you spot a bad sales hire in one week? 37:27 How to sell into a small, finite vertical market 42:32 The biggest AI opportunity in sales right now 51:32 Kevin's AI go-to-market tech stack TOPICS 1. Vertical SaaS Go-To-Market & Sales Strategy 2. SaaS Sales Hiring, Scaling & Leadership 3. Founder-Led Sales & Go-To-Market Fit 4. Vertical SaaS Outbound, ICP & Demand Generation 5. AI Sales Automation, CRM & RevOps

  6. Sep 23

    Who Wins the Vertical AI Wars? | Luke Sophinos vs Nic Poulos

    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. Instead, Luke and Nic debate the emerging battle taking place inside every software vertical. On one side are the legacy systems of record that have spent years building distribution, customer relationships and enormous proprietary datasets. On the other are a new generation of vertical AI startups moving at incredible speed, alongside AI-native services companies that can quietly enter through the back door by doing the work incumbents traditionally left to their customers. Get ready for this debate: -Why the SaaSpocalypse may have been overblown -Which software companies are actually benefiting from AI -The 4 strategies startups can use to attack SaaS incumbents -Why AI-native services could become a Trojan horse into the system of record -Whether incumbents need to own the “ChatGPT for their industry” 🎟️ TICKETS DROPPED. Vertical Software Summit — 5-billion-dollar Vertical AI CEOs confirmed to speak. Snag a ticket before they're gone: https://verticalsaasgroup.com/conference 👉 FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ 👉 FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ 🎬 TIMESTAMPS: 00:00 The SaaSpocalypse is over... now what? 02:02 What the software market data actually says 05:05 How AI startups can attack legacy SaaS 10:20 Why AI-native services are such a powerful wedge 16:16 What should legacy SaaS CEOs do right now? 21:29 Can incumbents actually reinvent their products? 23:39 Is the vertical AI M&A wave finally coming? 25:14 Why AI acquisitions could accelerate 27:12 How startups can position themselves to be acquired TOPICS 1. Vertical AI vs. Vertical SaaS 2. AI Startups & Legacy Software Incumbents 3. AI-Native Services & Systems of Record 4. SaaS M&A & Vertical AI Acquisitions 5. AI Distribution, Data Moats & Specialized Models

  7. Sep 16

    Why Vertical AI Wins The Decade | Dom Dinardo

    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 incredibly powerful software business. Now, as founder and CEO of Aforza, he's betting on the next evolution: vertical AI. Dom sees the history of modern software in three waves: horizontal SaaS dominated the 2000s, vertical SaaS emerged in the 2010s, and he believes the 2020s will belong to AI products built around the workflows, data and expertise of individual industries. In this episode of Verticals, Luke and Nic explore what actually changes when you build AI for a specific industry. They discuss: -Why vertical AI could define the next decade of software -What Salesforce taught Dom about horizontal SaaS -The concept of “vertical intimacy” he learned at Veeva -How to identify industries ripe for vertical software disruption -Why generic AI copilots often struggle to demonstrate ROI -Why the best enterprise AI may use photos, voice and actions instead of chat -What founders can learn from Veeva's go-to-market model If you're building vertical AI, enterprise software or the next generation of SaaS, this is a look at how one founder who lived through the previous two software waves is approaching the third. 🎟️ TICKETS DROPPED. Vertical Software Summit — 5-billion-dollar Vertical AI CEOs confirmed to speak. Snag a ticket before they're gone: https://verticalsaasgroup.com/conference 👉 FOLLOW DOMINIC DINARDO LINKEDIN ➡️ https://www.linkedin.com/in/dominicdinardo/ 👉 FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ 👉 FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ 🎬 TIMESTAMPS: 00:00 Why this decade belongs to vertical AI 02:23 From horizontal SaaS to vertical SaaS 07:18 The power of “vertical intimacy” 09:43 Why Dom chose the $30B consumer goods market 13:19 Why horizontal software struggles with vertical problems 16:56 How Aforza evolved from SaaS to AI 18:27 How vertical AI transformed a real sales team 24:40 Why generic AI copilots struggle to create ROI 28:22 How to price vertical AI without selling tokens 32:36 Why the future of AI isn't just a chat interface 38:33 The enterprise workflow AI can completely change 46:04 Scaling enterprise AI across 40+ markets 48:27 How to make enterprise implementations actually work 51:10 Which SaaS companies are most threatened by AI 52:16 The biggest lesson Dom learned from Veeva TOPICS 1. Vertical AI & Vertical SaaS 2. Salesforce & Veeva 3. Evolution of SaaS 4. AI Agents 5. AI Monetization

  8. Sep 9

    How AI Is Rewriting the Marketplace Model | Mike Duboe

    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 with Mike to explore why AI could make entirely new markets addressable to the marketplace model. Transactions that once required brokers, sales reps, phone calls and complex negotiations could increasingly be handled autonomously by agents. They discuss: -Which transactions consumers will actually hand over to AI -Why B2B commerce could be transformed by autonomous agents -How AI unlocks markets that were previously too complex for marketplaces -What trust and reputation look like when the buyer is an AI agent -Whether vertical SaaS and marketplaces eventually converge If you're building in vertical AI, marketplaces, B2B commerce or agentic software, this episode is a look at what happens when AI doesn't just help us shop, it starts participating in the economy itself. 🎟️ TICKETS DROPPED. Vertical Software Summit — 5-billion-dollar Vertical AI CEOs confirmed to speak. Snag a ticket before they're gone: https://verticalsaasgroup.com/conference 👉 FOLLOW MIKE DUBOE LINKEDIN ➡️ https://www.linkedin.com/in/mikeduboe/ 👉 FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ 👉 FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ 🎬 TIMESTAMPS: 00:00 How AI could transform B2B commerce 02:02 Why Mike is still betting on network effects 03:43 AI is making new marketplaces possible 05:20 Which purchases should AI automate? 08:30 The opportunity for agent-to-agent marketplaces 10:02 What is a “dark marketplace”? 11:46 Why AI threatens traditional marketplace take rates 13:54 Proprietary catalogs as the new marketplace moat 16:33 Trust in a world of autonomous AI buyers 20:42 Why B2B marketplaces historically became vertical SaaS 22:55 Will vertical AI and marketplaces converge? 24:18 The massive embedded advertising opportunity 28:49 Why AI products could become ad-supported 34:26 Distribution becomes the moat when software gets easier 35:55 Mike’s framework for investing in AI marketplaces TOPICS 1. AI Marketplaces 2. Agentic Commerce 3. B2B Commerce 4. AI Agents 5. Vertical AI

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A VC and a Founder intellectually spar on Vertical Tech & AI: covering the latest news, unpacking in-depth business strategies, and interviewing world-class leaders in the space, every Thursday.

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