Love, Marriage & Bootstrapping: Kim & Jason Coleman on Building a Software Company With Your Spouse

03/12/24 • 46 min

Kim Coleman and Jason Coleman are two entrepreneurs who have shared the journey of building a software company. However, their mission has been much more than a professional partnership. They’re a married couple with two kids who’ve built a successful company and several software products together: it’s safe to say they bring a unique perspective to the world of bootstrapping.

In 2006, they launched Stranger Studios, a web design and software development studio. In 2011 they launched their now flagship product Paid Memberships Pro. The big success followed in 2015 when they started building the team.

For most folks, logging off or commuting home at the end of the day is enough to separate your work life and your personal life. But for Kim and Jason, the lines are not as clear cut. In this episode, they discuss navigating personal and professional challenges, that range from compromising (or not) on hard decisions to facilitating a healthy work environment that encourages team morale, all while maintaining a harmonious marriage.

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Thanks to Kim and Jason for joining us and providing such valuable advice about building successful distributed companies. Join us next week with co-founder, bootstrapper, writer, and podcaster Arvid Kahl to learn about the positive impact that building in public can have on software product makers' lives and careers.

plugin.fm is brought to you by Freemius, your all-in-one payments, subscriptions, and taxes platform for selling software, plugins, themes, and SaaS. If you enjoyed this episode, head over to plugin.fm to check out previous episodes.

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Previous Episode

Matt Mullenweg on the Challenges and Successes of Building a Remote-First Company

Matt Mullenweg is best known as the visionary co-founder of WordPress and Automattic. He’s rightfully secured his place as one of the most prominent figures in the tech world and — more specifically — a pioneer of remote working,

Despite having no physical headquarters, Automattic currently has around 2000 employees working from 90+ countries and was recently valued at US$7.5 billion, making it one of the largest globally distributed companies in the world. WordPress is the biggest CMS in the world (and a movement of sorts), powering over 43% of the internet. Matt’s influence on tech has been far-reaching and revolutionary, and it’s not an exaggeration to say that his initiatives have changed the game.

While Automattic is Matt’s main focus, he also advises and invests in startups through his company Audrey Capital, and hosts Distributed, a podcast about the future of work and the foremost companies and leaders driving it.

In the first episode of plugin.fm season 2, we pick Matt’s brain about the challenges of building a remote-first company and the wins that arise from succeeding. Matt shares his insights and advice on navigating the pitfalls of a flexible workplace and building a successful remote-first company — ranging from accountability and compensation to hiring and productivity.

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Thanks to Matt for joining us and providing such valuable advice about building successful distributed companies. Join us next week with Stranger Studios owners Kim and Justin Coleman as they discuss the challenges of bootstrapping a software company with your spouse.

Next Episode

Promotion Through Education: How Courses Can Help You Grow Your Software Business

Chris Badgett is the co-founder and CEO of LifterLMS, a popular LMS (learning management system) plugin for creating, launching, and scaling courses. So far, LifterLMS has helped achieve 8 million+ enrollments and 12 million+ completed courses and lessons. It stands to reason that Chris is rightfully regarded as one of the leading voices in open-source eLearning and educational technology.

Chris is a passionate advocate for democratizing online education, and as a non-technical founder, he offers a unique business perspective on eLearning. He frequently shares this knowledge and expertise on LMScast, his podcast for innovators in the eLearning community.

Before developing LifterLMS, Chris’s company built custom course and membership platforms for clients. Even to this day, some of those platforms gross over 1 million dollars per year, year on year.

In this episode, we pick his brain and explore the transformative potential of educational marketing through course creation, focusing specifically on the possibilities for software product makers.

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Thanks to Chris for joining us and providing such valuable advice about building successful distributed companies. Join us next week with co-founder, bootstrapper, writer, and podcaster Arvid Kahl to learn about the positive impact that building in public can have on software product makers’ lives and careers.