Verticals: A Weekly Biz Show

How Levelset Built and Sold a Vertical SaaS Company for $500M | Ep 13

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.

Unlocking Billions in Embedded Fintech with Rahul Hampole (GM of Fintech @ ServiceTitan) | Episode 12

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 company02:30 – Rahul’s background: Plaid, Yelp, and ServiceTitan07:00 – Why vertical SaaS is uniquely positioned to win in fintech11:30 – When founders should actually add payments17:00 – The one metric that tells you you’re ready (attach rate vs usage)23:00 – Real take rates vs Stripe benchmarks29:30 – Stripe vs Adyen vs embedded providers vs in-house36:00 – Payments as infrastructure, not a feature41:30 – When to expand into lending, financing, and BNPL48:00 – Go-to-market, sales comp, and fintech incentives55:30 – Why fintech must feel invisible to customers1:01:00 – Agentic payments, automation, and what’s coming next1:07:00 – Final advice for vertical SaaS founders
 

2026 AI Winners & Losers: Vertical AI Predictions ft. Todd Saunders & Omar | Episode 11

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

How Martin Roth Scaled Sales From $1 to a $500M+ Exit | Verticals Ep 10

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 AI01:20 – Introducing Martin Roth (CRO, Levelset → Procore acquisition)04:00 – Joining at $0 revenue: what the early days really look like07:30 – Early sales hires: what matters and what doesn’t11:00 – When sales starts to break — and why it’s normal15:00 – Scaling structure vs scaling headcount18:30 – Founder-led sales vs professional sales leadership22:30 – Incentives, quotas, and misaligned behaviour26:30 – What changes as revenue grows from millions to scale30:30 – Vertical AI enters sales: what’s actually useful today34:30 – Where AI is overhyped in sales organisations38:30 – Humans vs automation: what doesn’t get replaced42:00 – Retention, expansion, and durable revenue46:30 – Common mistakes founders make too late50:30 – How to think about sales design before scaling54:30 – Lessons from seeing the full arc, end to end58:30 – Closing thoughts: building sales systems that last

How Dan Friedman Has Founded Multiple $100M+ Businesses | Verticals Ep 9

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 & AI01:30 – Introducing Dan Friedman (Thinkful → Chegg, Bolton & Watt)04:30 – Why Dan loves years 1–3 of building more than scaling orgs07:00 – What Bolton & Watt actually is (incubator vs venture studio)10:30 – How Moxie started: spotting unmet demand in MedSpas14:00 – “Business-in-a-box” explained — and why most versions fail18:00 – The three conditions required for business-in-a-box to work22:30 – Why Moxie started with off-the-shelf software (not custom)26:00 – Launch → Run → Grow: the Moxie operating model30:00 – Percentage-of-revenue pricing & retention realities34:30 – Churn, early failures, and moving up-market38:30 – Why ROI calculators matter more than features42:00 – Services + software: wedge vs defensibility47:00 – Why most vertical SaaS founders underuse services51:30 – The role of scale economics and national purchasing power55:00 – Vertical focus vs horizontal AI expansion58:30 – What founders consistently get wrong when choosing markets1:02:00 – Closing thoughts: building durable vertical businesses

How to Build a Vertical SaaS Empire with Sam Youssef, CEO of Valsoft | Verticals Ep 8

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

How to build a Revenue Machine with Kyle Norton, CRO | Verticals Ep 7

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. 

AI in Healthcare with Mike Kopko (CEO, Pearl Health) | Verticals Ep 6

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.

How Todd Saunders Built a $30M Vertical SaaS in Flooring (and Sold It) | Verticals Ep 5

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.

AI Marketplaces with Jack Greco (Co-Founder, ACV Auctions) | Verticals Ep 4

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.