Nick Hershey and the promise behind the counter

The awkward question came from a retailer. Where was this company going? What were the founders’ plans? Did they want to sell? Nick Hershey, co-founder and CEO of Rundoo, was initially taken aback. He had come to talk about software. The person across from him was asking about the future.

He came to see the sense in it. An independent store can have a family name above the door, decades of customer relationships and a working day that leaves little room for technological drama. Choosing a new point-of-sale system means entrusting another company with the business’s memory. A founder’s enthusiasm is pleasant. An answer about staying power is rather more useful.

Hershey’s answer is that he and co-founder Andrew Beckman intend to keep building. He says they have turned away acquisition approaches and kept veto rights over a sale. Those are statements of intent, with years of execution still ahead. They also reveal the question around which his working life now turns: how does a young technology company earn the confidence of people whose businesses might outlive it?

An apprenticeship at the paint counter

Tom King remembers Hershey arriving at his paint store with a request for help. Hershey wanted to develop a point-of-sale system for paint retailers. King knew the work. The two discussed what a store actually needed, and Hershey returned months later with changes. Their conversations became part of the product.

King’s family business had begun in 1976, when his father and uncle bought a store in Santa Cruz. It had its own habits, employees and customers long before Rundoo existed. King describes helping shape features, including the ability to transfer inventory between locations. That is the sort of improvement unlikely to receive applause at a technology conference. For someone trying to move stock between shops, it has a certain charm.

King’s Paint & Paper became Rundoo’s first live client in December 2022. The relationship gives Hershey’s story a useful starting point: a technically trained founder learning the particulars of a business from someone who had spent years running it.

His route to that counter had been circuitous. Originally from Cincinnati, Hershey went to Stanford, where he studied mathematics and computer science. His professional experience included Bridgewater, Citadel, Google and Enigma, spanning investment work, trading and product management. By July 2020, his byline appeared on an Enigma analysis of shipping imports, using container data to examine changes in trade.

That earlier work offers a glimpse of an enduring interest: finding something useful in the records that commerce leaves behind. At Enigma, the records described goods crossing borders. At Rundoo, they might describe a contractor’s purchases or an item sitting on a shelf. The scale changes; the need to turn information into a decision remains.

Beckman was his college roommate. In 2021, the pair started Rundoo and spent its first year working from Hershey’s apartment. They even invented the name, searching among nonsense words for something easy to pronounce and spell. A company intended to simplify work had at least spared its customers a pronunciation guide.

The error that survived a good sales day

In November 2024, Hershey announced Rundoo’s hundredth live client with a joke about the significance of the number to people using a base-ten system. The team had grown to just over thirty. He emphasized meeting clients face-to-face and keeping them informed about a product that could change every day.

The stores’ work gives those changes their shape. A supply retailer may sell to a homeowner one minute and a professional customer the next. Contractor accounts, purchasing histories and inventory all have to make sense together. A system that handles a simple sale can still leave the owner doing considerable detective work after closing.

Hershey has written about one California retailer, Jason, whose four paint stores carried a quiet pricing mistake. A price set to win an initial transaction had persisted as a customer-specific price. For ten weeks, repeat sales of the affected product went through close to cost. The overall results looked healthy enough for the problem to hide.

In Hershey’s account, Rundoo’s daily AI summary surfaced the suspicious sales. Jason investigated the transactions and discovered more than $4,200 in lost margin. He contacted the customer and negotiated a correction. The story is a company case study, rather than a promise that every store will find the same saving. Its interest lies in the thoroughly ordinary mistake it describes.

A clerk had made a decision for one sale. The system had remembered it for the next one, and the next. That is a recognizably human business problem, made expensive by repetition. Hershey’s argument for AI becomes easier to understand when it is attached to a paint price rather than a prediction about the future of everything.

His practical guide for store owners starts with experimentation: try a tool, learn to give it context, revise the result, then become proficient at one useful task. He asks readers to scrutinize vendors, including whether an AI tool can actually access their business data. The questions belong to the buyer, even when the buyer might eventually choose someone else’s software.

A shirt for every beginning

There is another side to Hershey’s enthusiasm for technology: getting people through the change. His explanation of switching to Rundoo spends time on data, hardware and training. A dedicated implementation manager coordinates the process. Stores receive a test environment before the real changeover, so employees can practice without damaging the live records.

He describes a typical preparation period of about a month, while allowing for much shorter projects and longer rollouts across many locations. The specificity matters. A retailer deciding whether to switch needs to imagine the intervening Tuesdays, including who will teach the staff and what will happen to the old customer balances.

Then comes the shirt. On go-live day, the team asks the customer to sign a Rundoo T-shirt and takes a photograph. The shirts hang in the office, keeping those stores visible to the people writing the software. It is an economical form of corporate decoration: each exhibit comes with a customer who expects the product to work.

Hershey is also willing to explain a choice that can make a prospective buyer pause. Rundoo has no offline mode. He describes experiments with local operation and the complications of synchronizing records and maintaining different versions. His proposed backup is cellular connectivity. Whether that suits a particular store is a practical question, and his willingness to spell out the tradeoff gives the owner something concrete to evaluate.

Growth gets a waiting room

Keeping customers close becomes harder as their numbers rise. In a May 2026 essay about growth, Hershey acknowledged that Rundoo’s support queues and implementation backlog had lengthened. The organization had allowed demand to run ahead of its capacity to help.

“We didn’t hire enough.”

Nick Hershey, on Rundoo’s support capacity

His response included a commitment to hire for the sales the company was closing and avoid selling beyond what it could support. It is a useful constraint for a founder to describe publicly. The contract that brings in revenue also creates work for someone who must answer a call when a checkout will not behave.

In August 2026, Rundoo announced a $30 million Series B led by Battery Ventures, bringing its disclosed financing to $48 million. The company reported serving more than 500 stores in the United States, Canada and the Caribbean. It planned to expand engineering in Redwood City and its commercial team in Chicago.

The money gives Hershey more room to hire and build. It also expands the number of relationships his company has to maintain. For the individual store, the useful measure will remain wonderfully stubborn: whether someone helps when help is needed. A financing announcement cannot take the next support call.

When he explains Rundoo’s mission, Hershey gives empowerment a practical meaning: an owner understanding something previously hidden, or a contractor paying a bill late at night because the process is convenient. Those examples make the ambition small enough to inspect. Did the owner learn something useful? Could the customer finish the task? For all the language surrounding new technology, these are questions a shopkeeper can answer without needing a presentation.

The long game has opening hours

Outside the company, Hershey’s interests include tennis, basketball, hiking and jazz piano. He has named Oscar Peterson and Bill Evans among his favorite musicians. It is tempting to turn the piano into a grand metaphor for entrepreneurship. Better to leave him a hobby without making it attend a strategy meeting.

His latest public conversations keep returning to store owners. He hosts Supply Stories, a Rundoo podcast whose opening episode features Tom King. The founder and the first customer are back in conversation, this time with a microphone between them. The subject has expanded from building a system to the experience of keeping a family business going.

In an October 2026 interview, Hershey described service as the part of retail he expects to remain valuable as technology advances. He was cautious about predicting what the next five years would bring. That caution fits the task he has chosen: tools can change quickly, while trust accumulates at the pace of repeated experience.

The question that once surprised him still hangs over the enterprise. Will the company stay? Hershey has offered his intention. Every new store, every implementation and every answered call will add to the answer. For a business built around the counter, the long term arrives one opening time at a time.