Verticals: A Weekly Biz Show

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 Intro01:03 Why founders are skipping venture capital05:44 Is the “SaaS-pocalypse” real?18:18 How AI is changing the startup landscape21:48 Will AI replace SaaS or just extend it?26:33 Can big companies adapt?31:36 Why commoditization is coming for software pricing37:39 What actually makes a company defensible now44:15 AI agents, distribution, and the next growth channel52:38 The real future of SaaS

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 winsThis 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 Intro01:05 From startup exit to laundromats12:00 Hardware vs software: the contrarian bet15:50 Why hardware became the moat19:00 The painful M&A that changed everything23:10 What almost killed the business...27:30 Building a company that doesn’t fit the VC playbook31:00 Why distributors beat sales teams36:00 The hidden power of customer expansion41:00 Why most SaaS metrics are misleading46:30 Designing your company for the exit52:00 The truth about IPOs and liquidity57:00 How AI actually fits into vertical SaaSIf you enjoyed this episode, drop a comment and hit subscribe so you don’t miss what’s next!

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.

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!

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!

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

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

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.

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.

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.

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.

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.

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 launch more than 150 vertical SaaS companies through Fractal. In this conversation, he challenges the way founders and VCs think about market size, moats, and defensibility in the age of AI. We dive into systems of record vs point solutions, why vertical SaaS can monopolize entire markets, and how LLMs are changing what’s possible in software - not just automating work, but replacing it. This episode is a deep, operator-level discussion on how vertical AI reshapes TAM, why speed now beats perfection, and what founders should prioritize if they’re building in regulated, complex industries. Whether you’re a founder, operator, or investor building or backing vertical SaaS or vertical AI, this episode will fundamentally change how you think about market size, product strategy, and long-term advantage. New episodes drop every Wednesday.

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 construction ecosystem post-Hurricane Katrina , all of which collided into the insight that became Levelset. He scaled the business from a side project doing ~$200k in revenue to tens of millions in ARR, then navigated a fast, high-stakes M&A process that closed at the height of the 2021 market.   This conversation cuts through M&A mythology and focuses on operator reality: how acquirers think, how founders should think about timing and leverage, why the best companies are bought not sold, and what founders get wrong when they fixate on the same buyer segment (general contractors) in construction tech.   Whether you’re pre-product, scaling a vertical SaaS business, or simply trying to understand how real outcomes happen in construction tech, this episode offers a practical, founder-first playbook grounded in lived experience, not theory.     We cover: The origin story: why liens and construction payment disputes created a massive software wedge How Levelset went from transactional to SaaS, and what changed the growth curve Why selling to suppliers and subs (not GCs) created differentiation and enterprise scale contracts Construction tech “dead ends” and where Scott sees opportunity beyond the GC workflow How Procore first approached the category (and why they couldn’t build it in-house) What it looks like when an acquirer is “in heat”, speed, leverage, and market-making The founder decision: duty to stakeholders, timing the cycle, and why exits happen when they do Scott’s advice to founders: excellence first, M&A second   If you’re a founder, operator, or investor building or backing vertical SaaS, especially in construction or the built world, this is a must-listen guide to how great companies get built, differentiated, and ultimately acquired.   New episodes drop every Wednesday.

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 payments and financial products at the right moment, and others burn months building the wrong thing, too early, or for the wrong reasons.   This conversation cuts through fintech hype and focuses on real operator frameworks: when to add payments, how to think about attach rate vs take rate, why Stripe benchmarks can be misleading, and how vertical SaaS companies should sequence fintech products without losing focus. Whether you’re pre-launch, scaling to $50M+ ARR, or debating Stripe vs Adyen vs building in-house, this episode offers a practical playbook grounded in real-world experience, not theory.   We cover: When it’s actually time to build payments The one metric that signals fintech readiness Realistic take rates for embedded payments (and why founders get this wrong) Attach rate vs usage: what really matters early Stripe vs Adyen vs embedded providers vs in-house builds How and when to expand beyond payments into lending, financing, and BNPL Why fintech should feel invisible — not bolted on Go-to-market and sales comp lessons for fintech products Where agentic payments and automation are headed next If you’re a founder, operator, or investor building or backing vertical SaaS, this episode is a must-listen guide to turning fintech into a durable growth engine — without falling into common traps. New episodes drop every Wednesday.   Episode Minutes 00:00 – Intro: Why every SaaS company becomes a fintech company 02:30 – Rahul’s background: Plaid, Yelp, and ServiceTitan 07:00 – Why vertical SaaS is uniquely positioned to win in fintech 11:30 – When founders should actually add payments 17:00 – The one metric that tells you you’re ready (attach rate vs usage) 23:00 – Real take rates vs Stripe benchmarks 29:30 – Stripe vs Adyen vs embedded providers vs in-house 36:00 – Payments as infrastructure, not a feature 41:30 – When to expand into lending, financing, and BNPL 48:00 – Go-to-market, sales comp, and fintech incentives 55:30 – Why fintech must feel invisible to customers 1:01:00 – Agentic payments, automation, and what’s coming next 1:07:00 – Final advice for vertical SaaS founders  

A group of veteran operators and investors come together on Verticals for a candid, end-of-year conversation on what actually happened in vertical AI in 2025, and what’s coming next in 2026. In this holiday special, Luke Sophinos and Nic Poulos are joined by Todd Saunders (Founder & CEO, Broadloom) and Omar (Partner, Euclid Ventures) to review last year’s predictions, debate the biggest winners and face-palms, and lay down bold calls for the year ahead across vertical AI, SaaS, and venture. This episode goes beyond surface-level hype. It’s an operator- and investor-level discussion grounded in real outcomes, lived experience, and healthy disagreement, not trend-chasing. We cover: - Which vertical AI companies actually won in 2025 — and why - The biggest face-palms and strategic missteps of the year - Where vertical AI is genuinely creating durable value - Why some fast-growing AI companies will struggle with churn - The future of AI roll-ups: hype vs reality - How system-of-record incumbents will respond to AI point solutions - Which verticals are primed for $100M+ ARR scale - Old-guard SaaS companies most at risk of disruption - Where AI is overhyped, and where it’s still underestimated - Bold predictions for 2026 across AI, SaaS, and venture If you’re a founder, operator, or investor building or backing vertical SaaS or vertical AI, this episode offers a sharp, honest perspective on where the market is headed, and where consensus thinking may be wrong. New episodes drop every Wednesday. Episode Minutes: 00:00 – Intro: Verticals holiday special & 2026 predictions 02:00 – Reviewing last year’s predictions 05:30 – Vertical AI winners of 2025 12:00 – Biggest face-palms and strategic mistakes 20:00 – AI roll-ups: opportunity or trap? 28:00 – Point solutions vs systems of record 35:00 – Where vertical AI actually scales 43:00 – Churn, retention, and fragile growth 50:00 – Old-guard SaaS at risk in 2026 57:00 – Dark-horse predictions for the year ahead 1:05:00 – Final calls: what really matters in 2026

A CRO who helped scale a company from its first dollar of revenue to a $500M+ acquisition joins Verticals for a practical conversation on sales, scale, and vertical AI. In this episode, Luke Sophinos and Nic Poulos sit down with Martin Roth, former CRO of Levelset, where he built and scaled the sales organisation from day one through their acquisition by Procore. We go deep on what actually changes as sales teams scale, the mistakes founders make as revenue grows, and how vertical AI is starting to reshape sales roles earlier than most teams expect. This is an operator-level conversation grounded in lived experience, not theory. We cover: What really changes when sales moves from early traction to scale Common mistakes founders make as revenue grows How sales roles and structure evolve over time Where vertical AI is genuinely changing sales workflows Where AI is overhyped, and what still requires humans Why incentives and structure matter more than tools What breaks first when growth accelerates How to think about scaling sales before problems appear If you’re building or leading sales in vertical SaaS or vertical AI, this episode offers practical insight from someone who’s seen the full journey, from zero to exit. New episodes drop every Wednesday. Episode Minutes 00:00 – Intro: Verticals, sales, and vertical AI 01:20 – Introducing Martin Roth (CRO, Levelset → Procore acquisition) 04:00 – Joining at $0 revenue: what the early days really look like 07:30 – Early sales hires: what matters and what doesn’t 11:00 – When sales starts to break — and why it’s normal 15:00 – Scaling structure vs scaling headcount 18:30 – Founder-led sales vs professional sales leadership 22:30 – Incentives, quotas, and misaligned behaviour 26:30 – What changes as revenue grows from millions to scale 30:30 – Vertical AI enters sales: what’s actually useful today 34:30 – Where AI is overhyped in sales organisations 38:30 – Humans vs automation: what doesn’t get replaced 42:00 – Retention, expansion, and durable revenue 46:30 – Common mistakes founders make too late 50:30 – How to think about sales design before scaling 54:30 – Lessons from seeing the full arc, end to end 58:30 – Closing thoughts: building sales systems that last

A founder who sold his first company for $100M+ and now builds businesses-in-a-box joins Verticals for a deep, operator-level conversation on vertical software, services, and scale.   In this episode, Luke Sophinos and Nic Poulos sit down with Dan Friedman — founder of Thinkful (acquired by Chegg) and now co-founder of Bolton & Watt, an incubator launching vertical companies like Moxie (MedSpas) and Meadow Memorials (funeral homes).   We unpack what actually makes business-in-a-box work, why most attempts fail, and how vertical SaaS founders should think about services, software, and defensibility in an AI-driven world.   We cover: Why “business-in-a-box” only works when three conditions are true How Moxie became the “Stripe Atlas for MedSpas” Why assembling off-the-shelf tools first beat building software too early The real reason vertical SaaS founders under-capture wallet share Services as a wedge vs a moat — and when they break Retention math, percentage-of-revenue pricing, and ROI defensibility Why vertical focus matters more as OpenAI expands horizontally How to spot vertical opportunities founders consistently misjudge   If you’re building in vertical SaaS, vertical AI, or compound startups, this episode offers practical frameworks — not theory — from someone who’s built, sold, and scaled repeatedly. New episodes drop every Wednesday.   Episode Chapters / Minutes 00:00 – Intro: Verticals, vertical tech & AI 01:30 – Introducing Dan Friedman (Thinkful → Chegg, Bolton & Watt) 04:30 – Why Dan loves years 1–3 of building more than scaling orgs 07:00 – What Bolton & Watt actually is (incubator vs venture studio) 10:30 – How Moxie started: spotting unmet demand in MedSpas 14:00 – “Business-in-a-box” explained — and why most versions fail 18:00 – The three conditions required for business-in-a-box to work 22:30 – Why Moxie started with off-the-shelf software (not custom) 26:00 – Launch → Run → Grow: the Moxie operating model 30:00 – Percentage-of-revenue pricing & retention realities 34:30 – Churn, early failures, and moving up-market 38:30 – Why ROI calculators matter more than features 42:00 – Services + software: wedge vs defensibility 47:00 – Why most vertical SaaS founders underuse services 51:30 – The role of scale economics and national purchasing power 55:00 – Vertical focus vs horizontal AI expansion 58:30 – What founders consistently get wrong when choosing markets 1:02:00 – Closing thoughts: building durable vertical businesses

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. New episodes drop every Wednesday. In this episode, Luke Sophinos and Nic Poulos sit down with Sam Youssef, Founder & CEO of Valsoft, one of the largest vertical SaaS aggregators in the world, with 130+ acquisitions, 3,000+ employees, and ~$750M in revenue. Sam breaks down how Valsoft built a Berkshire Hathaway, style software platform, what actually drives value creation post-acquisition, and how AI is reshaping vertical markets from the inside out. We cover: - How Valsoft scaled from a single hotel software acquisition to 130+ vertical SaaS companies - Why small, rational verticals outperform “big TAM” markets for aggregation - The real drivers of post-acquisition growth: payments, AI labs, global delivery centers, and product expansion - How to evaluate founders, integrity, and culture before buying a business - Why AI will accelerate value creation for systems of record, and destroy vendors with too much tech debt - What most people misunderstand about the threat of vertical AI upstarts - How Valsoft sources deals across 25+ countries with 100+ people in M&A - What founders should know before selling to an aggregator (and when to raise their hand) Whether you’re building in vertical SaaS, vertical AI, private equity, or exploring aggregation models, this episode gives you a masterclass in buying, scaling, and compounding durable software assets

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. New episodes drop every Wednesday. In this episode, Luke Sophinos and Nic Poulos sit down with Kyle Norton, CRO of Owner, to break down how one of the fastest-growing vertical SaaS companies went from ~$2M → $50M+ ARR in just over three years, and why most founders misunderstand what actually scales GTM in vertical markets.   We cover: - Why solving the highest-value job in a vertical (not the broadest feature set) creates breakout outcomes - Toast vs Owner, operations vs revenue, and how targeting a different job reshapes a category - How to build a GTM “revenue factory” instead of a traditional sales org - Why ** RevOps, data, and change management** matter more than “hero sellers” - What most founders get wrong about ACV, speed, and hiring at high-velocity SMB scale - How founder pattern recognition led Kyle to join Owner at ~$2M ARR, and what he looks for before backing or joining a company - Why AI is transforming sales leadership (not because of use cases, but because of culture and resourcing) Whether you’re building in vertical SaaS, vertical AI, B2B sales, or any market where GTM efficiency determines survival, this episode will give you frameworks you can apply immediately. 

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. New episodes drop every Wednesday. In this episode, Luke Sophinos and Nic Poulos sit down with Mike Kopko, CEO of Pearl Health, to break down how AI and value-based care are transforming one of the most complex industries on earth: healthcare. We cover: - Why healthcare is becoming the biggest vertical AI opportunity and where startups can actually win - AI for cost removal vs workflow enhancement — and why the former is where the real money is - How Pearl Health uses predictive analytics to prevent costly hospitalizations and align financial incentives across providers and payers - AI fatigue in the enterprise vs AI success in healthcare (42% of AI initiatives discontinued — why healthcare is different) - The rise of vertical AI funding in healthcare (Timecare’s $100M raise and the surge in oncology + senior care innovation) - Navigating government programs, value-based care, and risk-bearing models as a startup - The Pearl Health playbook: building for physicians first, landing wedge products through payments, and scaling upmarket to health systems If you’re building in healthcare, AI, SaaS, or any high-cost vertical where AI can directly impact financial outcomes, this one’s for you. Subscribe for more conversations with the founders and investors shaping the future of Vertical SaaS.

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. New episodes drop every Wednesday.   In this episode, Luke Sophinos and Nic Poulos sit down with Todd Saunders, Founder & CEO of Broadloom (acquired by Syncly), to dig into how he built and sold a $30M ARR vertical SaaS company in the flooring industry, and the unconventional playbooks that made it possible.   We cover: • Going from Google to niche SMB software, why “boring” is the new billion-dollar opportunity • The explosive pivot: ad-tech collapse → vertical SaaS focus → COVID demand boom • How community becomes a moat: conferences, Facebook groups, and content-led GTM • The Broadloom monopoly playbook: roll-ups, channel partners, and owning distribution • Transactional revenue vs SaaS revenue, and what PE is really willing to pay for • The truth about exits: cap tables, PE math, runway, and why most vertical outcomes look nothing like TechCrunch   If you’re building in SaaS, AI, or a service-based business in an “unsexy” industry, this one’s for you.   Subscribe for more conversations with the founders and investors shaping the future of Vertical SaaS.

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. New episodes drop every Wednesday. In this episode, Luke Sophinos and Nic Poulos sit down with Jack Greco, Co-Founder of ACV Auctions and founder of Greco VC, to dig into building marketplaces, the operator-to-investor shift, and how AI is reshaping product, margins, and retention. We cover: - The shift from systems of record to systems of action why AI-native UX lowers adoption friction - Verticalized spend management vs horizontal cards (when niches win; construction/healthcare examples) - The AI margin debate: inference costs, valuation sanity, and why true retention/cohorts matter - AR glasses and real vertical use cases once hardware reaches “consensus” (field service, supply chain, healthcare) - The ACV Auctions playbook: uniform info + guarantees, region-first scaling, and how to “hot-wire” marketplace liquidity - Operators → investors: how operator empathy changes selection, support, and outcomes If you’re building in SaaS, AI, or service-based marketplaces, this one’s for you. Subscribe for more conversations with the founders and investors shaping the future of Vertical SaaS.

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. New episodes drop every Wednesday. In this episode, Luke Sophinos and Nic Poulos sit down with Brian Litvack, Co-Founder and CEO of LeagueApps, to unpack how he’s built one of the most successful vertical SaaS companies in youth sports, turning a fragmented, hyper-SMB market into a high-retention, payments-powered platform. We cover: How Brian pivoted from a consumer startup to a dominant B2B SaaS platform Building go-to-market playbooks for hyper-fragmented SMB industries Scaling efficiently, surviving downturns, and raising growth capital from Accel-KKR If you’re building in SaaS, fintech, or vertical AI, this one’s for you. Subscribe for more conversations with the founders and investors shaping the future of Vertical SaaS.

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. New episodes drop every Wednesday. In this episode, Luke Sophinos and Nic Poulos sit down with Jeremy Yamaguchi, Founder and CEO of Cabana, to explore how he’s transforming the fragmented pool service industry through an AI-driven roll-up model, bringing technology, data, and scale to local operators. We cover: - How Jeremy built and exited multiple home-service companies before launching Cabana - Why AI roll-ups are reshaping traditional service industries - Lessons in leadership, M&A, and building tech-enabled operational excellence If you’re building in SaaS, AI, or service-based marketplaces, this one’s for you. Subscribe for more conversations with the founders and investors shaping the future of Vertical SaaS.

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. New episodes drop every Wednesday. In this episode, Luke Sophinos and Nic Poulos sit down with Ilir Sela, Founder and CEO of Slice, to explore how he’s unbundling the franchise model,  empowering 20,000+ independent pizzerias to compete with the giants. We cover: How Slice scaled a billion-dollar network of small businesses The power of Vertical SaaS and why it’s transforming local commerce Lessons in leadership, fundraising, and long-term vision If you’re building in SaaS, marketplaces, or local tech, this one’s for you. Subscribe for more conversations with the founders and investors shaping the future of Vertical SaaS.