Starting & Sustaining

Brennan Dunn, Co-founder of RightMessage

Brennan and I explore the trajectory of businesses and learning that led him to create RightMessage. Since founding his first SaaS application, Planscope, in 2011. Brennan began producing courses to help freelancers grow their business as a way to grow Planscope. However, as the content arm of Planscope grew, it became the primary breadwinner. Brennan eventually sold Planscope to focus on the content production with Double Your Freelancing. While optimizing the funnel and learning about the importance of personalization, he began to see the opportunity to create an application that could provide easy-to-use personalization for other businesses. After providing these personalization services in the form of consulting, Brennan recognized that the next step was to use his SaaS experience to create RightMessage. We also touch on the logistics of selling Planscope when it was financially intertwined with Double Your Freelancing. It required significant extra time to extricate the financials and clean up all of the books for the sale. Special Guest: Brennan Dunn.

Mathias Meyer, Co-founder and Former CEO of Travis CI

After helping found Travis CI and grow into the CEO role over six years, Mathias recently left Travis and starting helping other companies with their growth challenges. We talked about the difficulty of leaving and moving on after six years and the tactics that have helped him work through it. We also talk about the operational side of growth. While we all want revenue to grow, sometimes, we fail to think about how that growth affects operations and requires significant attention to the operational side of the business. We also touch on how bootstrapping lends itself to slower and steady growth with a little less stress. We discuss how Travis CI's support of open source projects started out simply as support for the open source community but had the wonderful side effect of great marketing. However, in the case of Travis, scaling to support so many free projects early on wasn't without its own challenges. And we cover some of the challenges of being a german business and doing business internationally while also having a remote team working asynchronously across time zones with nine hours of difference. Special Guest: Mathias Meyer.

Jaimee Newberry, Co-founder of Picture This Clothing

Picture This Clothing went viral immediately. From the outside, it looked like every entrepreneur's dream. But the reality of holding together a business that just went viral is completely different. Add in the logistics of printng custom shirts on demand and fulfilling the orders, and it's not all it's cracked up to be. Jaimee and I talk about the necessity of creating space in your life for opportunities to take hold. We explore what it's like running a fledgling business while experiencing viral growth as well as what happens after the viral growth subsides. We dive into what it's like getting viral traffic but not actually making any sales for the first week. We also talk about the importance of launching before you're ready, validating your idea, and making sure to see projects through and not leave them unfinished. Special Guest: Jaimee Newberry.

Steve McLeod, Founder of Feature Upvote

Ben Curtis, Co-founder of Honeybadger

Ben and I discuss the origins of Honeybadger, what it's like bootstrapping, and the sleepless nights brought on by running an infrastructure product. We also talk about Ben's experiences automating the company and growing it into a more mature and resilient business. Special Guest: Ben Curtis.