Verticals: A Weekly Biz Show

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

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🎬 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

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

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🎬 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

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

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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

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

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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

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

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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

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

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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

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

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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

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/

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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

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 teams can become an excuse not to build scalable products. This episode will tell you how to avoid this trap. In this episode, they unpack:-Why forward-deployed teams are becoming critical to vertical AI-How to stop an AI startup from becoming a services company-Why the best forward-deployed hires look more like founders than engineers-Why customer success could become a revenue generator instead of a cost centerIf you're building vertical AI, rethinking your startup org chart, or trying to understand how forward-deployed teams actually work beyond the hype, this episode breaks down what the model looks like in practice... and where it can go badly wrong.🎟️ 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 QUINN LITHERLANDLINKEDIN ➡️ https://www.linkedin.com/in/quinnlitherland👉 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 Intro01:24 Building AI automation for the home services industry05:05 Why the old SaaS org chart no longer works10:10 What does a forward-deployed employee actually do?18:04 The two traps of the forward-deployed model29:40 What should the ideal forward-deployed team look like?35:41 Can forward-deployed teams work with low-ACV customers?42:13 Why owning the workflow matters more than owning the data44:25 Is the software UI becoming irrelevant?53:18 The future: $500M companies run by five people58:58 The only three hires an AI-native startup needsTOPICS1. Forward-Deployed Teams

2. Vertical AI & Vertical SaaS

3. AI Agents

4. AI Startup Org Charts

5. The Future of Software

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 software. The rest went toward people, agencies, contractors, and services actually doing the work. But AI changes that equation: software can now execute the workflow itself, allowing startups to go after the service budget instead of just the software budget.

Yoni lays out five emerging business models he believes could define the next generation of AI companies: using services to differentiate software, using software to differentiate services, AI-powered rollups, agent networks, and hardware that differentiates software.

In this episode, they discuss:

-Why customers want outcomes, not workflow software

-How AI could expand traditional software markets by 30–100x

-The difference between selling software and taking responsibility for the work

-Why many vertical AI agents could struggle to build lasting moats

If you're building in vertical AI, investing in software, or trying to understand what comes after SaaS, this episode is a framework for the business models that could define the next decade.

🎟️ 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 YONI RECHTMAN

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👉 FOLLOW LUKE SOPHINOS

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NEWSLETTER ➡️ https://insights.euclid.vc/

🎬 TIMESTAMPS:

00:00 Why customers never really wanted software

06:27 The 5 business models that could replace SaaS

12:03 Why forward-deployed engineers are suddenly everywhere

16:40 The massive opportunity hiding in SMB labor budgets

17:35 How AI agents could create entirely new network effects

21:08 Why AI could make software markets 30-100x bigger

24:46 The problem with AI companies that just resell tokens

28:45 Software vs. services: who actually owns the outcome?

33:37 Why “better prompts” won't become a lasting AI moat

38:05 Is proprietary data really defensible anymore?

42:39 Why the software vs. services distinction still matters

49:18 The agent network business model explained

53:47 What happens when AI agents start spending money?

TOPICS

1. Vertical SaaS

2. Vertical AI & Enterprise Software

3. AI Agents, OpenAI, Anthropic & the Future of SaaS

4. Small Business Finance