Zack Dugow

Founder & CEO The COOL Company

Last Reviewed: September 19, 2026

Executive Summary

Zack Dugow is the founder and chief executive of the COOL company, an advertising technology group he built out of Insticator, the business he started in 2012 after a conversation with friends while watching Mad Men. Insticator began as something quite different from what the group is now: a consumer-facing product that let fans of television shows and sports predict outcomes, and which turned into an engagement layer publishers embedded on their own pages — polls, quizzes and games that kept readers on site and generated first-party data in the process. From 2020 onward Dugow bought his way outward from that position, acquiring an audience engagement business, a UK supply-side platform, a multi-location marketing firm and a dynamic creative optimisation specialist, and consolidated the lot under a single brand. The result serves close to two thousand clients with a team of more than a hundred, and sells AI-driven creative generation, media activation and measurement as one system.

Career Highlights

• Founded Insticator in 2012 and has led the business, through its rebrand as the COOL company, ever since.
• Acquired Squawk-It in 2020, the UK supply-side platform OKO Digital in 2021, the franchise and multi-location marketing firm Balihoo in 2023, and the dynamic creative optimisation company ADventori in 2024.
• Consolidated those businesses into one ecosystem built around the COOL AI platform, spanning creative generation, media activation and attribution across CTV and digital.
• Named to the DMN Top 40 Under 40 and to Crain’s New York Business 40 Under Forty.
• Led a company named repeatedly to the Inc. 5000, twice to the Deloitte Technology Fast 500, and to Crain’s New York Business Fast 50 and AdWeek’s fastest-growing solution providers for publishers.
• Founder and chief executive of RedRush Communications from 2008 to 2012, before Insticator.
• Mentor and adviser to the incubator and entrepreneurial initiatives programme at NYU Stern School of Business, and an active angel investor in growth-stage technology companies.

Professional Journey

Dugow’s first company was RedRush Communications, which he founded and ran as chief executive from 2008 until 2012. Insticator followed, and its origin story is one he tells often: the idea came from a conversation with friends while watching Mad Men, and the first version was a consumer site where fans of a television show or a sporting event could predict what would happen next, competing with each other through games, polls and quizzes.

The pivot that made it a business was recognising that the engagement mechanic was worth more to publishers than to consumers. Publishers were losing readers to social platforms and had almost no first-party data about the ones they kept; an embeddable unit that made people stay, click and answer questions solved both problems at once, and the resulting data made the publisher’s inventory more valuable to advertisers. Insticator built out from there into publisher monetisation more broadly.

From 2020 the strategy changed shape again, from building to buying. Squawk-It, an audience engagement technology, came in 2020. OKO Digital, a UK-based supply-side platform, followed in 2021, adding programmatic infrastructure and a European footprint. Balihoo, acquired in 2023, brought franchise and multi-location marketing — a different customer entirely, national brands with local outlets. ADventori in 2024 added dynamic creative optimisation, the piece that lets a single campaign assemble different creative for different audiences in real time. Each acquisition filled in a stage of the advertising pipeline the company did not previously own, and the rebrand to the COOL company marked the point at which the parts were presented as one thing rather than a collection.

What the group now sells is that pipeline as a single AI-driven platform: creative generated and varied automatically, media bought across connected television and digital channels, and attribution measured end to end. The leadership team around Dugow includes a chief technology officer, a general manager, a head of global advertiser sales and — telling of where the company thinks its leverage is — a chief of staff for internal AI optimisation.

Outside the company, Dugow mentors and advises through the incubator and entrepreneurial initiatives programme at NYU Stern School of Business, invests in and advises growth-stage technology companies, and belongs to YPO and the IAB. He contributes thought leadership through the Forbes Technology Council, a paid membership programme, writing on dynamic creative optimisation, mobile advertising, privacy and AI in advertising. He has been named to the DMN Top 40 Under 40 and to Crain’s New York Business 40 Under Forty, and speaks publicly about setbacks and rebuilding as much as about growth.

Education

No educational qualification for Zack Dugow could be confirmed during this review. The prior version of this profile listed NYU Stern School of Business under Education; that was an error — his relationship with NYU Stern is as a mentor and adviser to its incubator and entrepreneurial initiatives programme, not as a graduate, and neither his own site nor his professional profiles claim a degree from it. Two unconfirmed leads exist for his actual schooling — Hofstra University, studying psychology in roughly 2005 to 2008, and Baruch College in roughly 2008 to 2009 — but neither could be verified against a readable source and no degree award is attached to either, so neither is asserted here.