Bootstrapping EmailOctopus to $3m+ ARR - Jonathan Bull & Tom Evans

Bootstrapping EmailOctopus to $3m+ ARR - Jonathan Bull & Tom Evans

Author: James McKinven November 8, 2023 Duration: 17:11

Today I’m joined by Tom Evans and Jonathan Bull from EmailOctopus, an email platform who have bootstrapped to over $3m ARR since they were founded in 2014. They’ve been battling in a crowded and competitive market, with some huge funded companies to contend with, but they’ve made it work in an indie way. In this episode we talk about how they lost 99% of their users overnight, why they’ve chosen to compete on price rather than in a niche and their reasoning behind staying bootstrapped for so long.

Get the extended episode here: https://indiebites.com/membership

  • 00:00 Intro
  • 01:24 EmailOctopus Background
  • 02:57 How long did EmailOctopus take to build?
  • 03:09 Launching for free
  • 05:45 Tom joining EmailOctopus
  • 07:11 Growth
  • 07:48 Building in a crowded market
  • 08:55 Differentiating on price
  • 11:30 Raising vs bootstrapping
  • 12:58 Changing goals as a bootstrapper
  • 15:07 Fulfilling the side project urge

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Sponsor - EmailOctopus 🐙

EmailOctopus is an independently owned email marketing platform, built to support other small growing businesses. With a focus on affordability and ease of use, EmailOctopus contains all of the features you need to reach and grow your audience. You can start today, with their industry leading free plan where you can contact up to 2,500 subscribers without paying a penny.


Every Tuesday, James McKinven sits down for a short chat with someone who’s quietly building a business on their own terms. Indie Bites focuses on the real, often messy, beginnings of profitable, bootstrapped ventures. Instead of abstract theory, you’ll hear founders explain the exact moment an idea clicked, the scrappy ways they tested it without spending a fortune, and how they landed those crucial first few customers. The conversations are deliberately kept concise, getting straight to the practical insights that make a difference when you’re starting with limited time and resources. This podcast digs into the specifics of creating a sustainable income independently, covering the intersection of entrepreneurship, marketing, and hands-on business tactics. It’s for anyone who prefers learning from direct experience rather than corporate playbooks, offering a regular dose of motivation and actionable advice from people who are actually doing the work.
Author: Language: English Episodes: 100

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