How Justin Duke is building Buttondown into the perfect bootstrapped business

How Justin Duke is building Buttondown into the perfect bootstrapped business

Author: James McKinven February 8, 2025 Duration: 17:17

Justin Duke is the founder of Buttondown, a simple email tool he launched in 2017. Justin was last on the podcast 2 years ago when he’d hit $15k MRR and just left his role at Stripe to focus on Buttondown. I was struck by Justin’s well thought through approach to building. He makes calculated risks and shares a lot of his learnings on his blog, Applied Cartography (which is an essential read for any indie hackers).

This episode I catch up with Justin to hear how he’s grown the team to 8 people and his approach to building a company he loves. This is a cut down version of an hour long catch up I had with Justin available on the Indie Bites membership which is available at indiebites.com/membership, where we discuss his personal blog, how he structures his time as a new parent and we go deeper into hiring high agency unicorns.

Timestamps

  • 00:00 - Intro
  • 01:58 - Buttondown growth
  • 03:40 - How to build a company you don't hate
  • 07:16 - Marketing and positioning Buttondown
  • 11:17 - Buttondown's unique home page approach
  • 13:45 - Building a business you enjoy
  • 15:32 - Recommendations

My links

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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: 50

Indie Bites
Podcast Episodes
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