When I was 19, I wanted to spend a summer on the East Coast. I had never been. So I took the only job I could find that would actually get me there: selling educational books for kids door to door in small-town New Jersey.

It was one of the hardest things I have ever done.

The first few days I walked around in the heat, sweating through my shirt, hoping to survive. Hoping the next person wouldn't slam the door. Hoping someone — anyone — would offer a glass of lemonade. I thought seriously about quitting and flying back to California.

Then something shifted.

By the second week I knew people. I could open with: "Hi, I'm Ben — I'm the guy talking to families on this street this summer. I was just down the road with Stephanie, and her kids Jimmy and Jody…"

That shifted everything. Not a script. Not a discount. Just the fact that I had already been welcomed by Stephanie three doors down. People who would have politely declined my pitch the day before suddenly wanted to know what Stephanie had bought.

Vertical SaaS works the same way.

Operators look around before they look up

The default mental model for SaaS — "the best product wins" — does not survive contact with a vertical market. In horizontal SaaS, a buyer might compare four tools on a review site and pick the one with the cleanest interface. In a vertical, the buyer is an operator, and operators talk to other operators. The first question they ask is rarely "What's the best tool?" It's "What is so-and-so down the street using?"

That is why most great vertical SaaS businesses don't try to start everywhere. They start somewhere.

Toast started at one bar in Cambridge

Toast was founded in 2012 by three engineers — Aman Narang, Steve Fredette, and Jon Grimm — who came up with the idea over too many drawn-out checks at restaurants in Kendall Square. Their very first product launched at a single bar in Cambridge called Firebrand Saints, which gave customers a way to start a tab and pay through their phones.

For years, Toast was a Boston restaurant story. The reason matters. Restaurants are clannish. Owners eat at each other's places. Chefs trade staff. A POS that works wonderfully at the bar one block over has more credibility than any sales pitch, anywhere. By the time Toast turned outward, it had already won the city it lived in — and "the system the Boston restaurants use" is a sticky thing to be.

ServiceTitan started in their dads' neighborhood

ServiceTitan tells a similar story in a different vertical. Co-founders Ara Mahdessian and Vahe Kuzoyan grew up as sons of HVAC and plumbing contractors in the Armenian-American community in Glendale, California. They started building software in 2007, initially to help their own fathers' businesses run their books. The earliest customers were people who already trusted Ara's and Vahe's families.

Geographic density and community density layered on top of each other. The customers knew each other, worked the same trade, and had Sunday dinners together. ServiceTitan didn't have to overcome the "who else is in?" reflex. They were already who else was in.

Gladwell got there first

In The Tipping Point, Malcolm Gladwell argued that the spread of any idea — a fashion trend, a public-health message, a piece of software — runs through what he called the Law of the Few: a tiny number of people are connected to everyone else in a few steps, and most of us are linked to the world through those special few.

In a vertical SaaS market, "the few" are the visible operators. The clubs other operators tour. The names that get dropped in group chats. Win one of those, and you do not have to win the next ten — they win themselves.

CityPickle was our Stephanie

For PodPlay, CityPickle was Stephanie three doors down.

Back in 2023, when we were just turning our racquet-sports tech into a real SaaS product, Mary Cannon and Erica Desai — who co-founded CityPickle in the summer of 2021 — were the first pickleball operators to take a serious bet on us. CityPickle is the most visible pickleball brand in New York City. They run the year-round courts at Wollman Rink in Central Park under a 20-year operating agreement, the new 37,000-square-foot Times Square flagship at the Paramount Building, the Long Island City club, and seasonal activations from Hudson Yards to Dilworth Park in Philadelphia.

When CityPickle said yes to PodPlay, every other pickleball operator in New York took notice. Roll forward three years and the vast majority of pickleball played in the five boroughs runs on PodPlay. We did not have to chase it down operator by operator. The market did the work.

We are seeing the same pattern start to repeat in other geographies. Wherever a visible, well-run, hospitality-led operator picks us first, the operators around them tend to follow. The pattern is geographic, then it ripples.

That is what makes Mary and Erica special. They didn't just take a chance on a young product. They made it possible for every operator within driving distance of New York to take us seriously.

"Who else is in?"

When I worked in the investment business, the single question that unlocked every conversation was "Who else is in?" Allocators don't read a deck and decide. They read a deck and then they want to know which respected names already wrote the check. The deck describes the opportunity. The cap table validates it.

Vertical SaaS is the same thing but more local. The product page describes the platform. The customer logo wall validates it. And the customer logo wall gets read locally — operators want to see operators near them, not operators on the other side of the country.

If you are building in a vertical, that is the lesson. Pick a market. Find a Stephanie. Deliver something so good she tells the neighborhood. The product does the heavy lifting after that. Your job before that is to make the experience available — and to find the one customer whose name turns into the next ten conversations.

We get to celebrate exactly that this week. Episode 7 of The Joy of Pickleball drops next Tuesday featuring CityPickle's new Times Square flagship. 

Mary and Erica built something that genuinely needs to be seen to be understood. We are grateful for the trust, the friendship, and the introduction.

Catch it Tuesday.