Ajay Gupta learned to find an audience. Then he built Stirista.

Before Ajay Gupta had a marketing company, he had wrestling fans. As a teenager newly exposed to the possibilities of the internet, he built a professional wrestling website and an email newsletter. There were people out there who cared about the same subject, and a few lines of HTML could bring them within reach. For a boy who had grown up without a telephone line at home in a small Indian town, that was quite a change in the size of the neighbourhood.

The attraction was partly the wrestling. It was also the reply, the return visit, the discovery that somebody was paying attention. In his own account of those years, the audience made the lasting impression. Long before connected television entered his working vocabulary, Gupta had experienced the pleasure of publishing something people wanted to receive. A wrestling newsletter is an eccentric business school. Its entrance requirements, at least, are refreshingly clear.

He would eventually co-found Stirista with his wife, Candice, building a business around audience data and the means to act on it. The products became more complicated. The underlying question remained recognisable: who wants to hear this, and how do you reach them?

An English degree walks into a data business

Gupta studied financial economics and English at St. Lawrence University, then pursued creative writing at Texas State University. The combination gives his career a pleasing symmetry. One discipline asks whether the numbers work; another asks whether the sentence does. Advertising tends to need both, although its practitioners sometimes behave as if a spreadsheet can be moved to tears.

Early work on political campaigns brought the disciplines together in a practical setting. He saw how information about voters could shape the delivery of a message. A campaign has an urgent need to distinguish between people, rather than addressing the entire country as one mildly distracted constituent. That experience helped turn a youthful interest in online publishing into an idea for a company.

The writing background also survives in his view of creative work. When judging video, he values whether an idea makes an emotional connection and leaves an impression. Expensive production alone does not settle the question. For somebody who earns his living through data, he remains attentive to the experience of the person watching.

Two founders, one apartment, very orange shirts

Stirista began in 2009 as a two-person operation in an apartment. Ajay and Candice were the team. An early focus was multicultural audience data, an area where Gupta saw a mismatch between the changing country and the information available to marketers. The business grew from finding a specific gap rather than announcing that every problem in advertising was about to be solved.

There was little money for the usual theatre of business development. The Guptas drove from San Antonio to trade shows as far away as Boston and New York. Air travel and elaborate displays were beyond the budget. Bright orange polo shirts gave them something more affordable: a chance of being remembered. Their company colour did some of the work a bigger booth might have done.

It is a useful early portrait of the partnership. The founders were carrying their own pitch to prospective customers, literally over long distances. Marketing themselves demanded the same resourcefulness they were proposing to sell. Orange, in this instance, was a financial decision with sleeves.

The fuel gauge gets a vote

The travelling sales operation supplied a less flattering lesson, too. On Interstate 10 between San Antonio and El Paso, Gupta ran out of petrol. The conference booth and the couple’s little dog were along for the trip. Ambition had made it into the car; sufficient fuel had somehow failed to join it.

He has recalled the hours spent assembling awkward booths on conference floors, with hardware skills that did not quite match the requirements. His verdict on his own construction abilities was admirably brief: “I’m definitely not good at building things.” A software and data company permits a founder to delegate certain varieties of hammer.

His lesson from the roadside was that small practical details deserved attention alongside the grand business plan. A promising enterprise can be inconvenienced by an ordinary oversight. The anecdote gives the apartment origin a texture that a growth chart cannot: two people trying to get somewhere, with equipment, a dog and one very persuasive reason to stop.

A business that had to pay its way

Gupta’s approach to growth was shaped by having to fund the operation itself. He has urged founders to establish positive cash flow early, hire when the need exists and get one product right before adding another. There is a certain restraint in that advice. It leaves less room for the ceremonial hiring spree, a pastime with excellent photographs and occasionally awkward arithmetic.

He also favoured developing people early in their careers instead of assuming that every young business required expensive names on the organisation chart. Intellectual curiosity mattered to him: employees should understand the company’s work, keep an eye on competitors and continue learning. This was a business that expected people to grow along with its products.

In June 2020, Stirista raised $13 million in growth equity led by Wavecrest Growth Partners. Outside capital arrived after years of building. By then, Gupta had already spent a substantial part of his working life testing whether customers would pay for what the company could do.

Identity, without the fog machine

The language of advertising technology can make a fairly direct ambition sound like an entrance examination. Stirista helps brands understand their customers, find audiences and run campaigns. Its work connects data with email, digital media and connected television, or CTV: television delivered through internet-connected viewing.

Its identity graph, called OMNA, is intended to connect the information needed to recognise and reach audiences across channels. AdStir provides media buying. The attraction of keeping these capabilities together is practical: fewer handoffs between the people supplying audience information and those responsible for putting a campaign into the world.

Gupta has described the starting goal as fuller profiles, refreshed quickly enough to be useful wherever a campaign runs. A beautifully organised record has limited charm if it is out of date by the time somebody uses it. His interest is in the movement from information to action, with an eventual result a customer can inspect. The company’s machinery exists to make that journey shorter.

The people on the other side of the spreadsheet

For Gupta, running a company includes arranging reasons for people to enjoy being there. Stirista has described staff outings ranging from Spurs games to a My Chemical Romance concert, and a full-time events coordinator devoted to the employee experience. An office culture that makes room for both basketball and that particular soundtrack has at least considered the possibility of different tastes.

The same account connects his ambitions for Stirista to a belief in employees who share an interest in the product and the work. He has spoken of wanting the company closely associated with identity and CTV. Reaching that point requires people who can translate an expanding set of capabilities into something customers understand.

There is an outward-facing version of that habit, too. Gupta co-hosts The Marketing Stir podcast with Vincent Pietrafesa, talking with people across marketing. In a bonus episode, Ajay and Candice look back at the company’s first decade together. A business built around audiences also gives its founders regular occasions to listen.

Buying a company means meeting its founder

As Stirista expanded, acquisitions became part of Gupta’s work. His preferred candidates have a recognisable human shape: founder-run data businesses whose owners are approaching retirement. Many already have a working relationship with Stirista. The discussion begins with familiarity, rather than a cold introduction followed by a densely populated financial model.

In describing the approach in August 2026, he emphasised keeping employees and giving founders room to concentrate on selling again. Payroll, leases and the administration of a small business can consume the time that once went into winning customers. Joining a larger operation can change that allocation. His account of acquisitions dwells on what happens to the people after the transaction.

On July 15, 2026, Stirista announced its acquisition of Alesco Data, adding customer data and analytics capabilities. Alesco’s leadership would continue within the combined business. For Gupta, the expanding company is another way to bring more of a marketer’s work into one place.

“The founder wants to retire, and they’re looking for a nice home for their employees.”

Ajay Gupta · August 2026

The writer is still in the room

The industry has recognised the results. In 2024, the Marketing Club of New York selected Gupta for its innovation Apple of Excellence. Stirista appeared on the Inc. 5000 again in 2025, ranked 2,971. In 2026, Gupta was named an EY Entrepreneur Of The Year Gulf South finalist. These are dated markers in a career that began with very little institutional ceremony.

His Telly Awards judging offers another view of the work. He is interested in the balance between creativity and purpose, and in using data to inform a creative decision. He describes reading, watching and listening outside his industry as ways to prompt ideas, then talking those ideas through with colleagues.

That is a familiar practice for a writer: gather something from elsewhere, test the connection and see whether another person finds it convincing. The creative writing education sits comfortably beside the marketing business when you look at the daily task. Both require an idea to survive contact with an audience.

Still building, still impatient for an answer

By the summer of 2026, Gupta was discussing a more unified platform for marketing data, campaign execution and reporting. His ambition includes making complex analysis accessible to smaller businesses. A company should be able to understand its customers without assembling an expensive department merely to interpret them.

He also described a change in the tempo customers expect. Stirista had once distinguished itself with a 48-hour turnaround where a request could otherwise take seven to ten days. Now people want information immediately, including the freedom to check campaign performance whenever the question occurs to them. The founder who first marvelled at an online audience is still preoccupied with reducing the distance between a question and an answer.

Asked about building a company to sell it, Gupta offered a compact description of his attachment: “This is my baby. This is my sole passion.” The teenager found people who wanted to read about wrestling. The adult is still building ways for a message to find somebody interested. The audience has changed. His curiosity has kept its seat.