Everyone wants to build an AI company right now.But most founders are asking the wrong question.The real challenge isn’t building AI.It’s building something defensible once everyone else has access to the same models.In this episode of Verticals, the tables turn.Nic joins Vignesh Ravikumar and Brendon Schmidt from Sierra Ventures for a deep dive into what it actually takes to build and invest in vertical AI today.Nic shares lessons from nearly 15 years investing in vertical software and AI and explains why the biggest opportunities in AI aren’t just about models… they’re about workflows, distribution, and defensibility.They unpack the biggest shifts happening right now:-Why vertical AI is evolving faster than SaaS ever did-How AI-native startups are attacking incumbents-Why “speed” alone is not a moatAnd they tackle the biggest debate in tech right now:Is SaaS actually dying… or are we just watching a new generation of winners emerge?Watch until the end to find out!

#verticals #startup #ai #entrepreneurship #businessideas 👉 FOLLOW VIGNESH RAVIKUMARLINKEDIN ➡️https://www.linkedin.com/in/vravikumar1

👉 FOLLOW BRENDON SCHMIDTLINKEDIN ➡️https://www.linkedin.com/in/brendonschmidt/👉 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 Intro03:01 The shift from vertical SaaS to vertical AI08:18 How AI is changing the founder profile12:24 Why customer discovery matters more than ever18:55 How vertical AI startups beat incumbents28:14 Why “speed” is NOT a moat34:28 The rise of AI services businesses39:35 The vertical AI sectors investors want most42:39 How founders should position their company49:25 Is contrarian investing still alive in venture?58:59 The biggest mistakes founders make early on01:09:12 Is SaaS actually dying?If you enjoyed this episode, drop a comment and hit subscribe so you don’t miss what’s next!

In high-stakes industries, 99% accurate is the same as wrong.

That last 1% is the entire business.

In renewable energy, a single mistake can delay projects by months… or kill them entirely.

That’s exactly what Jacob Sandry saw while deploying over $3B into renewable energy projects at Goldman Sachs.

60% of projects were delayed. 30% were canceled altogether.

Not because the technology didn’t work… but because the process was chaos.

In this episode of Verticals, Jacob breaks down how Euclid Power is building the operating system for renewable energy — using AI, structured workflows, and human expertise to solve the “last messy mile” of energy development.

They unpack why vertical AI works differently in regulated, mission-critical industries:

-Why AI alone isn’t enough when mistakes have real consequences

-How humans-in-the-loop become a competitive advantage

-Why trust, compliance, and domain expertise matter more than model quality

They also go tactical on what is working right now:

-Why services + AI can outperform pure SaaS in vertical markets

-How to price against labor budgets instead of software budgets

-Why unstructured data is the biggest opportunity in enterprise AI

If you are building in AI, energy, healthcare, construction, or any industry where accuracy and trust matter more than speed, this episode is a masterclass in vertical AI.

👉 FOLLOW JACOB SANDRY

LINKEDIN ➡️ https://www.linkedin.com/in/jacobsandry/

👉 FOLLOW LUKE SOPHINOS

X ➡️ https://x.com/lukesophinos

LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/

NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/

👉 FOLLOW NIC POULOS

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

🎬 TIMESTAMPS:

00:00 Intro

01:55 The hidden bottleneck nobody talks about

05:01 From “alternative energy” to a $3B investment strategy

10:13 Why AI services work better than pure SaaS here

18:46 The multiplayer workflow behind billion-dollar projects

21:03 Why AI still struggles with the “last 1%”

31:37 Selling into industries where mistakes aren’t allowed

44:47 Is regulation actually a moat in AI?

47:20 Why energy could become the biggest AI opportunity of all

49:19 The long-term vision

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

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

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!

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

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

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

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

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

They also go tactical on what is working right now:

-How to win customers by proving value (not pitching AI)

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

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