Verticals: A Weekly Biz Show

Luke Sophinos
  • 0.0 (0)
  • BUSINESS
  • UPDATED WEEKLY

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. 4D AGO

    If AI Does ALL The Work… What Are You Even Selling? | David Haber

    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 why this shift could be bigger than SaaS itself.David explains why AI-native companies aren’t just selling software — they’re replacing labor. And how that single shift unlocks markets that were previously too small to matter.They unpack the new playbook for vertical AI:-Why TAM is no longer software spend, it’s labor-How messy inputs like email, fax, and voice are becoming billion-dollar wedges-Why AI-native companies are turning services businesses into high-margin softwareThey also explore what actually creates defensibility in this new world:-Why owning workflows and outcomes matters more than ever-How proprietary data compounds into a real moat-Why market structure is more important than market sizeAnd they go deep on the biggest strategic question:If AI owns the workflow, the data, and the outcome… Do you even need to charge for the system of record?If you are building, investing, or trying to understand where AI is actually creating value, this is one of the clearest breakdowns of what comes next.👉 FOLLOW DAVID HABERX ➡️ https://x.com/dhaberLINKEDIN ➡️ https://www.linkedin.com/in/haber/👉 FOLLOW LUKE SOPHINOSX ➡️ https://x.com/lukesophinosLINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/👉 FOLLOW NIC POULOSX ➡️ https://x.com/picnoulosLINKEDIN ➡️ https://www.linkedin.com/in/npoulos/NEWSLETTER ➡️ https://insights.euclid.vc/🎬 TIMESTAMPS:00:00 Intro01:28 Why the SaaS-AI shift is bigger than it looks07:09 Why “small markets” suddenly become massive10:06 The 3 ways to attack legacy software15:10 Why incumbents still have an advantage18:02 The real risk (and opportunity) in the AI era27:31 The messy inbox wedge (email, fax, voice)34:31 Why unstructured data is the biggest opportunity40:43 Voice, context, and the future of enterprise data44:15 The biggest mistakes vertical AI founders make45:28 The next wave: financial services, healthcare, industrial AI📃 Topics:1. Vertical AI vs SaaS2. AI replacing labor vs software tools3. System of record vs AI workflows4. AI services vs software margins5. Defensibility in AI startups6. TAM expansion through automation

    48 min

  2. APR 29

    SaaS-Pocalypse? Here’s What’s Actually Happening

    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 below the S&P 500 for the first time in modern history, why the market may be overreacting, and why software isn’t dying... it’s evolving. If you are building, investing, or trying to understand what AI actually means for software, this is a clear, grounded breakdown of where things are headed. TIMESTAMPS: 00:00 Intro 01:03 Why founders are skipping venture capital 05:44 Is the “SaaS-pocalypse” real? 18:18 How AI is changing the startup landscape 21:48 Will AI replace SaaS or just extend it? 26:33 Can big companies adapt? 31:36 Why commoditization is coming for software pricing 37:39 What actually makes a company defensible now 44:15 AI agents, distribution, and the next growth channel 52:38 The real future of SaaS

    1h 12m

  3. APR 22

    Nobody Took Laundromats Seriously… He Built a $1B Company (Here’s How)

    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 vertical SaaS opportunities in the world. Instead of buying laundromats, he decided to build for them. Today, his company Cents powers over 4,500 locations, processes more than $1B in payments annually, and just raised $140M to scale even further. But the real story isn’t laundromats. It’s the playbook. In this episode, we break down: -How hardware became a massive defensibility moat -The hidden power of retention + expansion over pure acquisition -How to build a business that doesn’t fit the VC “box”… and still wins This is one of the clearest breakdowns of how to dominate a niche industry, and why the biggest opportunities still live in places most founders ignore. TIMESTAMPS: 00:00 Intro 01:05 From startup exit to laundromats 12:00 Hardware vs software: the contrarian bet 15:50 Why hardware became the moat 19:00 The painful M&A that changed everything 23:10 What almost killed the business... 27:30 Building a company that doesn’t fit the VC playbook 31:00 Why distributors beat sales teams 36:00 The hidden power of customer expansion 41:00 Why most SaaS metrics are misleading 46:30 Designing your company for the exit 52:00 The truth about IPOs and liquidity 57:00 How AI actually fits into vertical SaaS If you enjoyed this episode, drop a comment and hit subscribe so you don’t miss what’s next!

    1h 2m
  4. How AI Startups Are BEATING Billion Dollar Companies (Vertical AI Playbook)

    APR 15

    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.

    1h 3m
  5. The Playbook for Building Vertical SaaS (10 Years of Hard Lessons) | Andres Robelo

    APR 8

    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 Intro 01:00 From booking courts to building a full OS 03:09 9 months to land the first customer (and why it mattered) 05:00 Scaling to 1,000 clubs across 37 countries 12:38 Why small product details make or break vertical SaaS 16:33 Why trust is the real moat in AI 23:11 The 10-Year Playbook (No shortcuts) 37:58 What Most Founders Get Wrong About Monetization 52:31 Andres’ Advice to founders If you enjoyed this episode, drop a comment and hit subscribe so you don’t miss what’s next!

    56 min
  6. Insurance Companies Don't Want This AI To Exist... | Episode 22

    APR 1

    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 Intro 00:40 From crypto to fixing a broken healthcare system 03:07 Why clinics don’t collect all the money they’re owed 06:24 The “long tail” problem costing providers MILLIONS 09:13 Staying in stealth while building a real AI system 12:02 Why you can’t build this on top of legacy software 14:23 How AI went from impossible to obvious  22:03 From 85% to 95%: how AI increases collections 24:41 Building SaaS-level margins without offshoring 30:04 Selling outcomes, not software 34:08 What keeps Chris up at night in an AI-first world 40:18 The real AI moat 49:41 The BIG vision for Camber If you enjoyed this episode, drop a comment and hit subscribe so you don’t miss what’s next!

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

    MAR 25

    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 Intro 01:18 From Wall Street to building an $85M logistics company 11:13 Finding the wedge: from simple freight to full supply chain control 13:56 The truth about AI agents: why most are failing 16:14 Selling outcomes vs selling software 19:42 Where real defensibility is built 29:57 The biggest mistake founders make 35:45 From AI skeptics to AI obsession 42:18 The AI agent landscape: what’s working, what’s not, and what’s hype 45:40 What actually matters for AI companies

    49 min
  8. This Startup Is Killing Spreadsheets with AI | Episode 20

    MAR 18

    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 Intro 00:56 From Goldman banker to building a $15B AI platform 02:10 The Hidden Chaos of Fund Admin 06:38 Why Trust is The Hardest Problem in AI 11:47 “B2B SaaS Is Dead”... And What Replaces It Next 14:43 Why Bundling WINS in AI 18:36 How Hanover Park Scaled From $1B to $15B  30:53 The AI Playbook That Actually Works 39:26 The Future of Software 46:54 The Biggest Lessons for Founders

    52 min
See All (27)

About

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.

Information

You Might Also Like