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.

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.