Email Octopus

Jonathan Boll had an early taste of the internet business world as a teenager, creating a website that let people send SMS and emails from anyone they wanted—a prank service he monetized at 17, making about $50/week before eventually shutting it down. His brother Gareth took a different path, starting a digital agency where he helped businesses drive traffic and revenue. Around 2013-2014, Gareth kept seeing the same problem: his clients' email marketing costs with MailChimp were exploding as their lists grew larger. He approached Jonathan with a simple question: "Is there a better way?" Jonathan had the technical chops, Gareth had the business intuition and marketing knowledge, and together they saw an opportunity to build something that didn't exist—a genuinely affordable email marketing platform using Amazon SES infrastructure, which already powered Netflix and Uber.

What followed was a grueling year of development. Jonathan coded email octopus in his spare time alongside a demanding full time job, working nights and weekends. He even rewrote the entire application midway through because he decided his initial programming language wasn't right. Jonathan came close to giving up multiple times, but Gareth kept pushing him: "We just say, and we'll write things. We need to get this out. We need to try it. Don't give up until we've at least got it in front of people." Meanwhile, Gareth was building audience. He followed MailChimp followers on Twitter, mentioned the upcoming product with the pitch "Email Octopus for a fraction of the price of MailChimp," and got their email addresses. By the time Jonathan finished the beta in late 2014, Gareth had accumulated 2,000 pre-signups.

When they launched, Email Octopus was barely functional—users couldn't even import subscriber lists; they had to add subscribers manually. But Gareth's pre-launch audience flooded in. He saw 200-300 people hit the site on day one. The real breakout moment came from a Reddit post where Jonathan simply said: "I've made this as a side project. It's completely free. Send all your emails. No cost whatsoever. Check us out." That post blew up. They ran completely free for almost a year, using Google AdWords to target keywords like "MailChimp alternative" and "Amazon SES providers." This strategy validated the product and infrastructure, but when they finally flipped the switch to paid plans, 99% of free users disappeared overnight—a sobering lesson that free users and paying customers want fundamentally different things.

After the free-to-paid conversion disaster, Email Octopus had to start over, but this time with paying customers. Jonathan went full time once they hit $3,000/month with about 200 users—enough to cover his London mortgage. Gareth split time between Email Octopus and his other business. They hired Tom, a former Secret Escapes executive, as COO—a move Jonathan initially resisted but later called "the best decision we ever made." Tom brought operational discipline: they started using proper email support tickets instead of missing messages, and brought marketing rigor to the business.

But growth brought chaos. Their volume quadrupled almost overnight in mid-2015, and they didn't notice for one to two months because they weren't monitoring metrics. Spammers had infiltrated the platform, exploiting the low price. They got mentioned on Black Hat forums. Jonathan had to spend that entire summer fighting spam. When they finally implemented filters and AI-based detection, they lost about a third of their revenue overnight—but it was necessary. They recovered by raising prices (counterintuitively, they doubled prices and revenue didn't decline because they were still 1/5 the price of MailChimp), improving infrastructure, and targeting higher-quality customers.

By the time of this interview, Email Octopus had evolved beyond simple pricing competition. They discovered "side project marketing"—like the email template pack they dropped on Product Hunt in November (downloaded by 2,000 people including Uber), which consistently generated 10 leads per day afterward. They focused relentlessly on simplicity and supporting the SME market, which valued ease of use over complicated features. Jonathan moved beyond just coding to learning business fundamentals—he said he learned more in 3-6 months of running the company than in 5 years as a developer. Gareth's experience in other markets informed strategy, pushing them to evolve tactics since "what worked during early days won't work today." They remained bootstrapped and profitable, never taking outside investment, and maintained a lean cost structure because their business model demanded it—they had to be able to undercut MailChimp and still make money.