Growing a fully bootstrapped email-marketing platform to $37M ARR

While Rebecca Shostak was running a profitable template subscription shop for photographers, she saw a gap. Two years later, the gap wasn't filled yet, so she built Flodesk.

Within four months, she hit 1M ARR. Now, she's at $36M ARR.

Here's Rebecca on how she did it. 👇

From designing for rock stars to founding SaaS

I'm the cofounder and CEO of Flodesk, an email marketing platform that I bootstrapped into a profitable company generating over $36 million in annual recurring revenue.

I was born and raised in Silicon Valley, so I grew up steeped in the tech world. My father, Rob Shostak, authored the Byzantine Generals' Problem, a foundational paper in computer science, and my uncle, Seth Shostak, is a renowned science celebrity and head astronomer at the SETI Institute.

But I carved my own path in design, not science. I studied Design and Media Arts at UCLA. In my first job out of college, I designed for major rock bands like Linkin Park, Rihanna, Sheryl Crow, Alanis Morissette, Collective Soul, and The Killers.

From there, I founded Galleree, a successful template subscription shop for professional photographers. That's where I learned the small business aesthetic and first spotted the gap Flodesk would fill: creative small businesses needed beautiful email designs, and the market offered no solution.

Flodesk launched in 2019 and became profitable within two weeks, thanks to a viral branded footer in every email, word-of-mouth growth, a performance model, and an unlimited pricing model that bucked the industry's per-subscriber tiering.

We hit a million in ARR within four months and five million within a year, funding it all with about $90K pooled from our own savings.

Today, we serve over 100,000 paying customers and have grown to roughly 90 employees, all while remaining entirely self-funded. And in January, Inc. named me in its Female Founders 500 list.

Flopping the prototype

Flodesk stemmed from a frustration I experienced firsthand. When I ran Galleree, my template subscription shop for photographers, Mailchimp email templates were by far the most-requested product. But customers bought a beautiful template and replied the next day in angry all-caps, demanding a refund because implementation was so hard. Demand was clearly there, but the tools were broken.

I waited years for someone to solve the problem. Eventually, I realized no one else would. So I teamed up with my cofounders, Martha Bitar and Trong Dong, to build something better.

When Y Combinator rejected us in 2018 (at a time when many in tech dismissed email as a dying channel), we pooled our own money and built the product anyway.

Our first prototype flopped. We watched an early tester sit down with it and just sink into her chair, completely lost. It was a huge blow to my ego, but it forced us to rethink our approach to everything and strip the product down to its most essential flows, presenting one step at a time. We iterated dozens of times a day until we got it right. I'll never forget the moment a tester cried happy tears because she could finally create a beautiful email and make sales on her own.

It was still barebones. It was just the ability to send an email manually. No editable templates, no intuitive UI. I was hand-designing emails in Photoshop for our early beta users and walking them through how to send them on the platform one by one.

Right before we launched, we had about 30 beta users, and when we switched to paid, not one of them wanted to stop. That was a big signal for us.

The technical side

On the technical side, we built on Amazon SES from day one and got AWS startup credits to keep costs down.

Infrastructure turned out to be our biggest challenge. We had no experience running an email platform, and we were learning deliverability, anti-spam compliance, and AWS infrastructure on the fly. At times, AWS nearly shut us down because scammers had gotten onto the platform and we hadn't built the right safeguards yet. We experienced many late nights and close calls.

Other than AWS infrastructure, we use Amazon SES, Sendgrid, and more recently, OpenAI and Claude.

Expansion revenue

Flodesk is a SaaS platform. We launched with a flat rate of $38 a month, offering unlimited subscribers and sends, and a 50% off coupon for our early beta users.

We deliberately chose unlimited subscribers. At the time, every other email platform charged more as lists grew, creating anxiety around growth that we considered fundamentally backwards. We wanted our customers to feel excited about growing their audience, not penalized for it. Because we offered no free tier, every customer contributed revenue from day one, a key factor in how we stayed bootstrapped.

Expanding beyond email helped us grow our revenue, too. We built Flodesk Checkout for selling products and services directly, a link-in-bio tool, and advanced workflow automation. Adding e-commerce to the platform opened up new revenue and deepened the value we provide.

Organic growth

Our growth has largely been organic.

Early on, we added a "Made with love by Flodesk" footer to every email sent through the platform. This introduced our brand to customers' entire lists each time they sent an email. That viral loop was huge. It makes the product itself our biggest growth driver.

We also built an affiliate program that anyone could join. We baked this into the product's original launch, so the engine ran from day one. We were surprised that 76% of referral revenue came not from big influencers, but from thousands of small voices — everyday users referring a few people each. That long tail became incredibly powerful.

Layer on community word of mouth, an explosion of affiliate-generated content, organic traffic, performance marketing, and AOE, and that's been the formula.

Watch users and follow your gut

I'm obsessed with data and experimentation, but ultimately I follow my intuition. That might sound contradictory, but they work together.

The data tells you what's happening, but your gut tells you what to do about it. Staying close to our customers is a big part of that. I still hop on user interviews every week, even as CEO. That direct line to the people we're building for keeps my instincts sharp and ensures we never lose touch with what actually matters.

In fact, if I had to start over, I'd push ideas into customers' hands even faster. We spent months going around in circles in internal product and design debates when we should have been sketching, prototyping, and getting reactions.

As soon as we figured out that the best insights came from watching someone actually use the product, we started accelerating fast.

Learn how to communicate with your cofounders

Learning how to work together as founders was tough in the beginning. The three of us were conflict-avoidant by nature, and in the early days, we'd perform competence instead of admitting when something wasn't working.

Learning to communicate openly about real problems turned out to be just as important as building the product.

Regulate your nervous system

One of the biggest game changers for me was when I started working with a somatic coach who helped me regulate my nervous system and become much more aware of how I show up around the team.

When you're a founder, your energy sets the tone for the whole company, and understanding that on a body level — not just intellectually — has changed how I lead.

Learn how to delegate

Learning to delegate was another significant step. For a long time, I held onto everything because I thought no one could do it the way I would. Letting go of that opened up space for me to focus on what only I could do, and it made the team stronger.

Start now with an embarrassing wireframe

Here's my advice: Put what you're building in front of customers much sooner than you think.

I'm talking the most bare-minimum, embarrassing wireframe of your idea. Don't wait until it's polished. The feedback you get at that stage is the most valuable feedback you'll ever get, because it tells you whether the problem you're solving matters to someone before you've spent months building the wrong thing.

The good news: There's never been a better time to do this. With vibe coding tools, you can go from idea to clickable prototype in a weekend. The barrier between "What if" and "Here, try this" has disappeared. Use that. Get something ugly into someone's hands, watch their reaction, and let that guide everything you build next.

And don't confuse funding with validation. VC money isn't real traction. Delighted customers are. If people love what you've built enough to pay for it and tell their friends, you have a business. Everything else is noise.

What's next?

Our goal is to build the next generation of design-forward, AI-powered marketing tools and create the best marketing asset design in the world.

But the north star is simpler than that: We want to be the one service small businesses can't cancel. The biggest problem most small business owners face is marketing themselves, and if we can solve that so well that Flodesk becomes indispensable, we've done our job.

You can follow my work on my personal Instagram or Flodesk's Instagram. And check out Flodesk!