In 2018, Y Combinator’s accelerator rejected Rebecca Shostak’s pitch. She and her co-founders pooled their money and got the company off the ground anyway. In January 2026 she became CEO of the company, Flodesk, which reports more than $36 million in annual recurring revenue and no outside capital.
| At a glance | |
|---|---|
| Co-founders | Rebecca Shostak (CEO), Martha Bitar (executive chair), Trong Dong (CTO) |
| Company | Flodesk, email marketing for small businesses |
| Public launch | August 2019 |
| Outside capital | None, per the company |
| Annual recurring revenue | More than $36 million, per the company |
| Customers | More than 100,000 small businesses, per the company |
| Shostak named CEO | January 2026 |
A designer’s problem
AWS’s startup blog says she started out designing merchandise for a company with a roster of artists, and Bitar said on the SaaS Club podcast that Shostak started out designing for rock stars like Rihanna and Linkin Park.
Her first company of her own was a template shop, selling Photoshop email templates for MailChimp to wedding photographers. Flodesk came out of what went wrong there. According to AWS, customers kept struggling to use the templates, which pointed to a bigger product: a platform for branded email. AWS says she and Bitar came together to create a prototype around January 2018 and that Flodesk had one by the summer of 2019.
The no, and what they did next
Inc. reported that investors turned Shostak down when she was fundraising in 2018, including the startup accelerator Y Combinator, which rejected her pitch. The founders pooled their money instead. Shostak also told Latka in 2024, “We went through Y Combinator startup school.” The rejection Inc. describes is of her pitch to the accelerator. Inc. also reports that the founding team worked on the product in the evenings and won a $10,000 grant through Startup School.
The product went out in August 2019. On SaaS Club, host Omer Khan put the climb to the first $1 million in annual recurring revenue at about four months, and the Practical Founders podcast says the company has been profitable since the second week after launch. These are founder-reported numbers from a private company.
Flodesk’s position recalls Heather Whaling, who built Geben Communication with no outside investors. The businesses are different, but by their own accounts neither company has taken outside investors.
The pitch changed
Flodesk used to charge new customers one flat rate however big their list grew.
That is no longer the deal for new customers. EmailOctopus reported in November 2025 that the unlimited plans were closing to new sign-ups, with existing customers keeping theirs. Flodesk’s pricing page now sets prices by subscriber count across its Lite, Pro and Everything plans. The change landed just before Shostak’s promotion, and anyone reading older coverage of Flodesk should not assume the flat rate still applies.
The handover
Shostak announced the milestones on the company blog on January 22, 2026: more than $36 million in annual recurring revenue, 13 billion-plus emails sent by members that year, and her move into the CEO role as Bitar became executive chair. As recently as March 2025, Practical Founders was still introducing Shostak as chief brand officer.
It is a handover inside the founding team, which makes it a different kind of change from the one Victoria Prew made at Hurr, where a founder gave the job to her operator and left to start again. At Flodesk the outgoing CEO stayed as chair, the CTO stayed, and the designer who started with templates took the top job. In April 2026, Flodesk announced that Inc. had named Shostak to its 2026 Female Founders 500 list.
What we could not confirm
We have not seen audited financials, and every revenue and customer figure here comes from the company or its founders. Sources also differ on the founding date: Flodesk says 2019, while AWS says early 2018. Inc. places her fundraising in 2018.
Sources: Flodesk’s company page, pricing page, January 2026 blog post and April 2026 press release, Inc. and its newsletter, AWS Startups Blog, Latka, SaaS Club, Practical Founders and EmailOctopus. Last checked November 4, 2026.
Frequently asked questions
Who is Rebecca Shostak?
She is the co-founder and, since January 2026, the CEO of Flodesk, an email marketing platform for small businesses. She began as a designer working on artist merchandise, then ran a shop selling email templates to wedding photographers before Flodesk.
Did Y Combinator reject Rebecca Shostak's pitch?
Inc. reported that the startup accelerator Y Combinator rejected Shostak's pitch when she was fundraising in 2018, and that the founders then pooled their money. Shostak separately told Latka in 2024 that the team went through Y Combinator's Startup School.
Has Flodesk raised outside funding?
Not according to the company. Flodesk's own company page, last reviewed in October 2026, describes it as bootstrapped with no outside capital. Inc. reports that the founding team won a $10,000 grant through Y Combinator's Startup School. Flodesk also reports more than $36 million in annual recurring revenue. Those figures are the company's own and are not audited.
When did Rebecca Shostak become CEO of Flodesk?
January 2026. Co-founder Martha Bitar, who had been CEO, moved to executive chair, and co-founder Trong Dong is CTO, according to the company.
Is Flodesk still flat-rate?
Not for new customers. Flat-rate plans closed to new sign-ups in late 2025, and pricing now rises with subscriber count. EmailOctopus reported that existing customers keep their unlimited plans.