Rebecca Shostak

The Designer Who Outgrew the Industry

At ten years old, Rebecca Shostak was teaching herself Photoshop. At thirteen, she appeared on the cover of Silicon Valley magazine talking about the internet. By twenty, she was designing tour merchandise for Rihanna and seeing her Linkin Park t-shirts on the racks at Hot Topic. None of that is the most interesting part. The most interesting part is what she noticed: small businesses everywhere had beautiful websites, polished Instagram feeds, and absolutely terrible email.

That friction - the specific, tolerable kind that people stop noticing - became Flodesk. Rebecca co-founded the company in 2018 with Martha Bitar and Trong Dong, bootstrapped it on their own savings, and watched it hit profitability fourteen days after the 2019 launch. The catalyst was a single email from the Rising Tide Society to its members. Within an hour, fifty people signed up. The company has not taken outside funding since, and it has not needed to.

The Rejection That Proved Nothing

Y Combinator passed on Flodesk. The investors who reviewed their pitch were convinced email marketing was a dying category - that nobody was building a future there. Rebecca took note and kept moving. By 2026, Flodesk had cleared $36 million in annual recurring revenue, with over 100,000 paid customers across small businesses, creators, and solopreneurs. The platform sent 13 billion emails in 2025 alone. Email was not dead. The design had just been terrible.

The backstory matters here. Rebecca had run an earlier company, Galleree, that gave wedding photographers branding and design tools. It reached $500,000 in annual revenue with 2,000 customers before she spotted the pattern that would become Flodesk: her customers kept asking for better email templates, and when they tried to use them in MailChimp, they hit a wall. The tool was built for enterprise marketing teams, not a florist in Nashville trying to look professional in an inbox.

Design as Infrastructure

Rebecca's creative lineage is specific. Her father, Robert Shostak, co-authored the Byzantine Generals Problem - a foundational paper in distributed computing that every computer science student eventually encounters. Growing up with a computer science pioneer in Silicon Valley meant entrepreneurship was ambient, not aspirational. But Rebecca's instinct ran toward the visual. She studied design and English at UCLA and won the Adobe Design Achievement Award, becoming the youngest person to receive it.

The music industry years shaped her understanding of brand at scale. Designing merchandise for Rihanna's Umbrella Tour and extensive work for Linkin Park - her favorite band - meant learning how visual identity translates across thousands of physical objects and millions of fan impressions. It also meant she understood the difference between design as decoration and design as communication. Flodesk was built on that distinction. The platform's drag-and-drop builder is not just easier than competitors - it's architecturally different. Users can embed polls, add countdown timers, apply custom fonts, and build sales pages that look like they came from a premium agency, not a mid-2000s newsletter tool.

Vietnam, AI, and the 'Do-It-For-Me' Revolution

In 2024, Rebecca did something unusual for a CEO: she moved to Vietnam for five months and embedded directly with Flodesk's engineering team. The goal was to build proprietary AI technology from the inside out, not to buy an API wrapper and call it innovation. By October 2025, Flodesk was filing seven patents on the resulting features.

The vision she is building toward is what she calls the "DIFM" marketing tool - do it for me. Not AI that requires a user to write a good prompt. AI that understands a small business owner's brand, audience, and goals well enough to run their email marketing with minimal input. That's a significantly harder problem than content generation, and it's the bet Flodesk is making as it moves beyond email into a full marketing ecosystem.

"For every dollar spent on email marketing," Rebecca notes, "on average, you get $30 to $40 back in return." That number is not hypothetical for Flodesk's customers. The platform's emails consistently achieve 17% higher open rates than the industry average. The 100,000+ customers on the platform collectively generated over $33 million in revenue through Flodesk in 2025, and added 314 million subscribers to their audiences.

From Brand Officer to CEO

For most of Flodesk's life, Martha Bitar held the CEO title while Rebecca served as Chief Brand Officer. The transition to CEO in 2025 reflects a natural evolution: as Flodesk doubles down on AI and engineering, having the person who spent five months in Vietnam building it lead the company makes operational sense. Her philosophy has not changed. "Get out of the way, but stay in the work." She still believes the biggest differentiator any company can have is great design, and she still looks for friction - especially the kind people have learned to tolerate.

She draws inspiration from museums, her architect husband's deep knowledge of design history, and the creative expressions of Flodesk's own customers. The brand is built on paper-textured warmth, not the cold minimalism that dominates SaaS. That is not an accident. It is a positioning argument made in pixels.