Verticals: A Weekly Biz Show

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

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:

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

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.