Business – Nathaniel Stevens

The Operating Layer of Local Business: A Vertical-SaaS Thesis

Nathaniel Stevens — Sun, 14 Jun 2026 04:42:53 +0000

The biggest software opportunity of the next decade is not another tool for enterprises. It is the operating system for the local business on your corner — and there is room for a category leader in every trade.

I have spent twenty years on one idea, approached from three directions. I founded Yodle to help local businesses get found. I founded Punchey to help them get paid and stay organized. And through Stevens Ventures I now invest in founders chasing the same prize. The idea is simple to state and hard to execute: own the operating layer of local business.

Why “horizontal” software keeps failing Main Street

For years the conventional wisdom was that small businesses would adopt the same general-purpose software as everyone else — a generic CRM, a generic scheduler, a generic payments tool. They mostly did not. Not because they are behind the times, but because a tattoo studio, a pet grooming shop, and an auto-detailing business do not run the same way, and a tool built for “everyone” is built for no one in particular.

The person behind the counter does not want a platform. They want their day to work. They want the booking, the deposit, the reminder, the payment, the review request, and the rebooking to happen without them thinking about it — in the specific language and rhythm of their specific trade. General software cannot do that. Vertical software can.

A salon is not a “small business.” It is a salon. The software that wins will know the difference.

The pattern I keep investing in

Look at the companies clustered around my work and the strategy is not subtle:

TattooPro — the operating system for tattoo studios.
GroomPro POS — point of sale built for pet groomers.
DetailPro — software for auto-detailing businesses.
Punchey — payments and operations for service businesses broadly.

Each one takes a single trade seriously enough to build the whole system it runs on, not a feature it tolerates. That is the bet, placed many times: in every meaningful category of local service business, there is a vertical operating system waiting to be built, and the company that builds it well becomes the default — sticky, beloved, and very hard to displace.

What I look for as an investor

Because I have actually been the customer — I have taken payments at a dealership and sold software to small businesses — I tend to weigh things differently than a purely financial investor. A few of the questions I care most about:

Does the founder know the trade in their bones? The best vertical-SaaS founders often come from the industry they are now arming.
Does the product make the day work, or just add a dashboard? Software that creates work loses. Software that removes work wins.
Is payments in the model? The operating layer and the money layer belong together; that is the lesson of Punchey.
Can it become the system of record, not a side tool? Tools get switched. Operating systems get kept.

The opportunity, in one line. There are thousands of local-business categories and very few of them have their category-defining software yet. The founders building those companies are, to me, the most interesting and under-covered entrepreneurs in technology — and backing them is the most natural extension of everything I have built.

I learned this thesis the hard way, in a Ford dealership and at a company that scaled to fourteen hundred people. I am betting the next decade on it. The corner store is not too small to deserve great software. It is exactly the right size.

Related:
Stevens Ventures ·
Punchey ·
Yodle ·
About Nathaniel Stevens

Why I Came Back to Run Stevens Ford

Nathaniel Stevens — Sun, 14 Jun 2026 04:42:51 +0000

I sold the company I built for $342 million. Then I went back to sell Fords in the town where I grew up. People ask me why. Here is the honest answer.

There is a version of my story that ends in 2016. That is the year Web.com acquired Yodle, the local-marketing company I started as a Wharton student with a $30,000 loan. It is the clean ending — founder builds company, founder sells company, founder rides off. It is also not what happened.

What actually happened is that a few years later I came home to Milford, Connecticut, to run my family’s Ford dealership. Stevens Ford was established in 1955. My father ran it. His father was part of the story before him. And when my father passed, the question in front of me was not a business question. It was a family question with a business attached.

The dealership was never a backup plan

I want to be precise about something, because it is easy to misread. Coming back to run Stevens Ford was not a step down from technology, and it was not a retirement. The dealership is where I learned everything that made the technology work in the first place.

When I was a teenager, I ran internet sales for the dealership — this was the early 2000s, when most local businesses still treated the web as a phone book with pictures. I watched customers research cars online for weeks and then show up to a sales process that had not changed in decades. The gap between how people shopped and how local businesses sold was enormous. That gap became Yodle. It became Punchey. It became the entire thesis of my investing. Every one of those companies is, at bottom, an attempt to give local businesses the tools I wished we had on our own showroom floor.

I did not leave the dealership to escape it. I left to build the software it deserved — and then I came back to run the original.

What a $342M exit does not buy

An exit is a wonderful thing. It validates a decade of work, it takes care of the people who took the risk with you, and it gives you options. What it does not do is replace the thing a seventy-year-old family business has, which is continuity. Stevens Ford has sold cars to three generations of some Milford families. You cannot raise that. You cannot acquire it. You can only inherit it and try to be worthy of it.

When my father passed, walking away would have meant letting that continuity end on my watch. I was not willing to do that. So I stepped in as CEO and Dealer Principal — and I brought with me everything I had learned building software for businesses exactly like ours.

The full-circle part. The dealership funded the company. The company funded the thesis. The thesis funded a fund. And the fund — Stevens Ventures — now backs the next generation of founders trying to do for tattoo studios, pet groomers, and auto detailers what I once tried to do for car dealers. It all traces back to a showroom in Milford.

What I am building now

Today I run three things at once, and to me they are one thing. Stevens Auto Group is the operating business — real cars, real customers, real Main Street. Punchey is the software for businesses like it. Stevens Ventures is the capital behind the next wave of that software. Founder, operator, investor: three seats at the same table, all pointed at the same belief — that local service businesses are the most under-served important market in the economy, and the people who give them great tools will build great companies.

So when someone asks why a guy who sold his company for nine figures went back to sell Fords, the honest answer is that I never really saw them as different jobs. They are the same job, viewed from different chairs. And the dealership is the chair I started in.

Related:
Yodle: the inside story ·
Stevens Auto Group ·
Stevens Ventures ·
About Nathaniel Stevens

My Second Ring: The People Behind the Work

Nathaniel Stevens — Mon, 13 Apr 2026 07:31:46 +0000

People · Conversations · Shared work

Six documented connections across Yodle, Punchey, public radio, and the work of explaining local-business technology: Kartik Hosanagar, Ben Rubenstein, John Berkowitz, David Olk, David Martin Davies, and Dennis Yu.

Nathaniel Stevens and Dennis Yu, from Dennis’s April 2026 article about Nathaniel’s personal website. Photo context.

The people behind a company tell a richer story than its milestones alone. Here are six people whose work connects with mine through Yodle, Punchey, public radio, and the challenge of explaining local-business technology.

Kartik Hosanagar, Ben Rubenstein, and John Berkowitz helped build Yodle. David Olk brought point-of-sale experience to Punchey’s board. David Martin Davies brought the customer’s questions to public radio. Dennis Yu helped bring years of stories and photographs into a personal website.

Kartik Hosanagar

Yodle co-founder

Turning an intensive service into a repeatable product.

Ben Rubenstein

Yodle co-founder and childhood friend

Taking the idea into real customer conversations.

John Berkowitz

Yodle co-founder

Testing assumptions and learning from the customer.

David Olk

Punchey board appointment, 2024

Bringing point-of-sale operating experience to the team.

David Martin Davies

Texas Public Radio host

A conversation about tipping and the checkout experience.

Dennis Yu teaching on stage. Photograph from his About page. Photo context.

Dennis Yu

Longtime collaborator

Connecting the early Yodle stories with the website today.

Kartik Hosanagar: turning a service into a repeatable product

Kartik Hosanagar and I co-authored a Knowledge at Wharton retrospective published on April 6, 2016. It describes a pivotal part of Yodle’s development: Kartik joined the founding team in fall 2005 to help move the business from labor-intensive services toward a repeatable marketing platform.

The account connects his work on keyword selection and bidding algorithms to a concrete product problem: serving local businesses without rebuilding every account by hand. That shift from individual service to a repeatable system is the central teaching thread in our retrospective.

For someone building a service business, the useful question is where expert judgment belongs and where a repeatable process can do the work. A strong collaborator connects expert judgment and a repeatable process to the company’s real problem. The original article is the place to explore that transition and the tradeoffs involved.

Source 1 · Source 2

Ben Rubenstein: taking an idea into customer conversations

Ben Rubenstein and I were childhood friends before Yodle. Allison Fass’s May 2013 Inc. profile follows Ben from graduating at Penn in May 2005 into the early work in Philadelphia: getting the idea in front of local customers and listening to what they needed.

The profile follows the effort to turn an online-marketing idea into a business that local customers would actually pay to use. Its example of a local dentist makes the early challenge understandable: the service had to connect a business’s online presence with an interested prospective customer. Ben’s story makes the customer-facing work visible.

A useful reading exercise is to separate an idea’s appeal from the evidence of demand. What problem did a customer recognize? What did the team have to explain? Why would that customer keep using the service? Those questions make this an operating story. Ben’s experience puts a person and a customer conversation behind the much shorter phrase founding a company.

Source 1 · Source 2

John Berkowitz: learning from customers instead of protecting an assumption

John Berkowitz’s IdeaMensch interview identifies him as a Yodle co-founder alongside Ben Rubenstein and me. In that interview, he explains the original local-business problem through my work at my father’s dealership: people were searching online, while many smaller businesses were difficult to find there.

John’s answers are especially useful because they connect method with milestones. He describes talking with customers, working through problems, and learning to test assumptions more carefully. His reflection on early go-to-market decisions shows how customer evidence can improve an initial approach.

For a founder reading the interview, turn that into a review question: what evidence would change the plan? The value of a working relationship grows through thoughtful disagreement and the ability to put a better explanation or test in front of the team. John’s answers give this part of the Yodle story a practical voice: keep learning, ask questions, and examine the approach.

Source 1

David Olk: matching operating experience to a specific problem

Punchey announced David Olk’s appointment to its board on April 29, 2024. The announcement identifies him as a ShopKeep co-founder and former chief operating officer, and quotes me as Punchey’s founder and chairman. It also quotes Sylvain Mansier as CEO at the time of that release.

The connection was point-of-sale software for local service businesses. Punchey’s announcement emphasized David’s operating experience at ShopKeep and the perspective he could bring to product and customer decisions.

The linked company announcement explains the appointment in its original terms. For someone assembling an advisory group, the transferable question is which specific operating experience the business needs and how that person is expected to contribute. A useful introduction connects that experience to a real question about the product, customers, or organization; it does more than add a recognizable name.

Source 1

David Martin Davies: asking what a checkout screen means to people

David Martin Davies hosted To Tip or Not to Tip? on Texas Public Radio’s The Source in November 2023. We discussed the questions that surface when a checkout screen asks someone to leave a tip: the social pressure, the expectations, and where the money goes.

The program description raises questions about tipping prompts, customer pressure, and transparency about who receives a tip. Those are human questions around a technology interface. A payment screen may be easy to implement while remaining difficult for a customer or worker to interpret.

That is why this interview belongs beside the product-building stories. A useful discussion of software includes both the people affected by its design and the business installing it. The original audio is on the linked broadcaster page. Listen with the customer’s question in mind: what does this screen ask me to do, and what does it tell me about what happens next?

Source 1

Dennis Yu: keeping a long-running story connected to its sources

Dennis Yu’s archive contains both early Yodle-era mentions and a later article about building my personal website. His older writing discusses knowing me during the Penn and Yodle period. His April 2026 website article brings that connection forward and includes a photograph of us together.

A founder can accumulate interviews, company histories, photographs, and explanations across many places. Dennis’s website work brings those materials together so a visitor can move from a photograph to an interview, or from a company chapter to the person who helped build it.

For a reader, the practical habit is to follow a story beyond its headline. The photograph gives the website account a human setting, and the earlier articles add a sense of continuity. This is the value of keeping an archive: a new piece can connect to work already explained, instead of making every visitor start from the beginning.

Source 1 · Source 2 · Source 3

Read the people stories alongside the company stories

Explore these conversations alongside the company chapters: Yodle for the founding story, Punchey for local-business software, and Stevens Auto Group for the dealership work. Each gives the people stories a different setting.

An outdoor portrait from my existing photo library. Photo context.

Choose the story that matches the question in front of you: product repeatability, customer demand, testing an assumption, relevant operating experience, or a more understandable checkout screen. Start with a person, follow the conversation, and bring a useful question back to your own work.

Source 1 · Source 2 · Source 3 · Source 4

More moments from the work

Nathaniel Stevens, from the portrait collection on this site. Photo context.

Explore the people and the ideas

Where should I begin with the Yodle story?

Start with the retrospective Kartik Hosanagar and I wrote for Knowledge at Wharton. Then read Ben’s Inc. profile and John’s IdeaMensch interview for the customer and operating perspectives.

What did David Olk bring to Punchey’s board?

Punchey’s April 2024 announcement highlighted David’s experience as a ShopKeep co-founder and former chief operating officer, connecting that work with point-of-sale software for local service businesses.

Where can I hear the tipping discussion?

The original November 2023 episode, To Tip or Not to Tip?, is on Texas Public Radio’s The Source. The Davies section links directly to the broadcaster’s audio page.

Which story is most useful for a new founder?

Choose the question you are working on: Kartik for repeatable products, Ben for customer demand, John for testing assumptions, David Olk for relevant operating experience, or Davies for the human side of a software interface.

Keep exploring

Sources & further reading

Tipping Has Gotten Out of Control

Nathaniel Stevens — Thu, 19 Mar 2026 19:12:55 +0000

I recently had the honor of joining David Martin Davies on “The Source” at Texas Public Radio to talk about something that affects all of us: tipping. The episode, titled “To Tip or Not to Tip?” aired on November 16, 2023, and it sparked one of the most honest conversations I have ever had about the state of tipping culture in America.

David opened the show with a question that really set the tone: “Has tipping gotten out of control?” And honestly, I think the answer for most Americans right now is yes.

The Pressure to Tip Is Everywhere Now

If you have bought a coffee, picked up takeout, or even grabbed a bottle of water at a counter recently, you have probably been hit with a screen asking you to tip 15%, 20%, or even 25%. It is everywhere. And it is not just me noticing this. A majority of Americans now say they feel increased pressure to tip in more places than they did just five years ago.

David put it really well during the show when he described how “it just became too easy to add another page on the checkout touch screen and swing it around.” That is exactly what happened. The technology made it frictionless for businesses to ask for tips, and now consumers are stuck in this awkward loop of guilt and social pressure every time they make a purchase.

Here is what has changed about tipping in just the last few years:

Tipping used to be reserved for sit-down restaurants and a handful of service jobs. Now it shows up at fast-casual counters, drive-throughs, self-checkout kiosks, and even online retail.
Consumers feel confused and frustrated about when and how much to tip. The rules keep shifting and nobody is explaining why.
There is zero transparency about where your tipped dollars actually end up. Does the barista get it? Is it pooled? Does management take a cut? Most of us have no idea.
The whole system has shifted from genuine gratitude to what feels like middle-class guilt and social obligation.

Where Does Your Tip Actually Go?

This was one of the biggest things David and I dug into during the interview. He raised a point that really stuck with me: “Is this tip going to end up in the pockets of the person we interacted with? Or will it go into a pool to be split evenly among the staff?”

And that is the thing. Most of us just tap a number on a screen and move on with our day. We assume the person who made our drink or served our food is going to see that money. But the truth is, we rarely know. Is it split at the end of the day? At the end of the pay period? Does the house take a percentage? There has been no real communication, negotiation, or dialogue about any of this.

As someone who runs a technology investment company, I see this from a business perspective too. The technology behind these point-of-sale tipping screens made it incredibly easy for businesses to offload part of their labor costs onto the customer. That is a real problem when there is no transparency about where those dollars land.

Is Tipping Actually Fair?

David asked a question during the show that I think gets to the heart of the issue: “Shouldn’t a worker be compensated with an agreed upon wage that doesn’t fluctuate depending on who happens to use their service that day?”

That question really resonated with me. Think about it. A server working a Tuesday lunch shift might make significantly less in tips than someone working a Friday dinner, even though they are doing the same job with the same effort. That is not fair to the worker. And on the flip side, a customer should never feel like they are being held hostage for better service. Tipping was supposed to be about gratitude, not leverage.

I believe workers deserve predictable, livable wages. Tips should be a bonus for genuinely great service, not a substitute for what employers should already be paying.

How Technology Changed the Tipping Game

One thing I brought up on the show is how platforms like Square, Toast, and Clover completely transformed tipping culture almost overnight. Before these systems, you tipped at a sit-down restaurant because there was a line on the receipt. Now every point-of-sale system has a tipping screen baked in, and businesses turn it on by default because why wouldn’t they? It is free money from their perspective.

But here is the catch. The customer is now doing the math in their head every single time they buy something. “Do I tip at this place? How much? Will the person behind me see what I chose? Will the cashier judge me if I hit ‘No Tip’?” That mental load adds up, and it is turning a simple transaction into an emotionally charged decision.

What We Can Do About It

I do not think tipping is inherently bad. I still tip generously when I get great service at a restaurant, and I think most people feel the same way. What I do think is that we need to start having honest conversations about how tipping fits into the bigger picture of fair wages and worker compensation.

Here are a few things I think would help:

Businesses should be transparent about where tips go. If you are asking customers for a tip, tell them exactly how it is distributed among your staff.
Employers need to pay fair wages first and treat tips as a bonus, not a subsidy for low pay. Workers should not have to rely on the generosity of strangers to make ends meet.
Consumers should feel empowered to tip when they genuinely want to, not because a screen is guilting them into it. It is okay to say no when you are picking up a to-go order you placed yourself.
We need a bigger conversation around tipping policy at the local and national level. This is not just a consumer issue. It is a labor issue, a technology issue, and an economic issue all wrapped into one.

Listen to the Full Interview

I am grateful to David Martin Davies and the team at Texas Public Radio for having me on “The Source” to dig into this topic. It is a conversation that more people need to be having, whether you are a business owner, a service worker, or just someone who is tired of feeling awkward every time you check out at a coffee shop.

You can listen to the full 24-minute episode here: To Tip or Not to Tip? on TPR.

I would love to hear what you think. Has tipping gotten out of hand in your experience? Drop me a message or connect with me on social media. Let us keep this conversation going.

Questions to Ask Yourself Before Starting a Business

Nathaniel Stevens — Mon, 22 Dec 2025 02:53:01 +0000

Despite high property costs and borrowing rates, today is still a promising time to start your own business. A recent survey showed millennials and “side hustlers” saw business ownership as the best way to build personal wealth. Younger generations, such as Gen Z, are reportedly the most likely to become small business owners, proving there will be a big wave in the coming years of promising new entrepreneurs. Yet, while younger, ambitious go-getters may have passion and drive, it’s essential to ask yourself a few crucial questions to ensure you’re financially, emotionally, and mentally prepared to take the leap — some I asked myself before starting my own business years ago.

What is my demand and Competition?

Aside from identifying your target audience, it is of utmost importance to understand and evaluate market demand and the competitive landscape so you can answer the question, “Where do I fit in?” This involves conducting market research to assess sufficient demand and understanding how your business can be differentiated. Research methods may include conducting surveys to potential clients, hiring a consulting firm to do A/B testing, or simply going out and asking people via a “door to door” approach. Simultaneously, identify who else is in your space. Who will you compete with, and what part of the market do they touch that you don’t? Do you tangentially overlap with them, or are there aspects of your business that they don’t touch upon? What is your “Unique Selling Point?”

Am I mentally prepared?

Before leaping into a new venture, consider if you’re ready to take on the stress and mental stamina launching a business requires. As a business owner, you are responsible for anything that could go wrong. It’s imperative to gauge if you’re prepared to make the potentially appropriate lifestyle changes and face the uncertainty of entrepreneurship. Common sacrifices may include long hours, financial insecurity, emotional stress, and time away from home or loved ones. Once you understand the hard work that goes into executing the long-term plans of your business and have a sound support system behind you, you are a step closer to being ready to embark on your business idea.

What is my business/revenue model?

While money isn’t always the only outcome, you must ensure the business has financial viability, especially if you’re employing other people. If you intend to receive funding, you must strongly respond to how you will generate revenue.

Do I have enough initial capital and funding?

You must ensure you have enough initial capital when kicking off your business. To understand what you’ll need, research the costs of the necessary infrastructure, technology or personnel, including the fees for registration/licensing, raw materials, and inventory acquisition, packaging, real estate/rent, and advertising and marketing.

Do I have the correct registration and taxes in place?

Upon building a business, you need to register it and obtain the correct licenses both at the federal and local levels. Federally, you must obtain your taxpayer identification number (TIN) and employer identification number (EIN). Your EIN is an important step to start and grow your business and is needed for tasks such as opening a bank account and paying taxes.

Potential Plan B

90% of new businesses fail. If that happens to you, what is your next step? Do you plan to scale into a more significant business or franchise, sell it, or pass it on to someone else? If things go wrong, do you have a personal financial buffer? Lastly, will the closing of your business emotionally crush you, or do you have things outside of work that keep you centered, motivated, and hopeful? In volatile markets and competitive businesses, you must approach each new venture with a “plan B” if it doesn’t work out.

By thinking through your answers to these questions, you can better assess the feasibility of your business idea and develop a comprehensive plan for what’s next. Aside from these practical questions, the cornerstone trait of a new business owner will be enthusiasm and passion for whatever it is they plan to build. Find inspiration in the big picture but excitement for the more minor details.