Pretty Penny: Revolutionizing Online Couponing for Women

Pretty Penny is a fresh entrant in the competitive couponing space, specifically catering to young, fashion-forward women and professionals who prefer online shopping. Currently bootstrapped, the startup offers a streamlined browser extension that automatically detects retail websites, scans for relevant discounts, and presents them in a clean, user-friendly interface.

Challenging the Couponing Giants

Breaking into a market dominated by heavyweights like RetailMeNot—which boasts 450 million website visits and 500,000+ offers—is no small feat. However, Pretty Penny differentiates itself by prioritizing user experience and aesthetics. Unlike many coupon sites that appear cluttered or “spammy,” Pretty Penny aims to appeal to women with its polished design and intuitive functionality.

The Founders’ Vision

Founded by two MBA graduates juggling full-time careers (one of whom recently welcomed a baby), Pretty Penny reflects their commitment to creating a premium couponing tool. The CEO, who prefers anonymity for now, brings expertise in brand management and product development. Though self-funded, the startup has invested nine months in development, far surpassing a mere “side project.”

Accelerated Growth with Sierra Labs

Pretty Penny gained traction after joining Sierra Labs, the incubator arm of ISBX. Known for supporting strong teams with solid business plans, Sierra Labs provided access to dedicated developers and technical resources. This partnership has been instrumental in refining Pretty Penny’s offerings.

How It Works: Smarter Coupon Discovery

The platform aggregates over 200,000 active offers from 12,000+ merchants, including direct partnerships with major retailers like:

  • Bloomingdale’s
  • Saks
  • Macy’s

Deals are sourced from:

  • Third-party aggregators
  • Manual entries (e.g., email promotions)
  • A proprietary web crawler (in development)

Personalized Shopping Experience

While compe*****s like RetailMeNot focus on verifying coupon validity, Pretty Penny leverages an algorithm to tailor deals based on women’s shopping behaviors. This personalized approach aims to make discount hunting seamless and relevant.

Now in Open Beta

With its public beta launch, Pretty Penny invites users to test its Chrome extension (download here). The goal? Gather feedback to fine-tune personalization and expand its merchant network. For women who value both style and savings, this startup is one to watch.


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