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.

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.