Founders Gone AI

Bootstraps and Snowcaps: SaaS in Winter


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In episode 6 of "Midlife CriSaaS," Kevin, Steve, and Jeff come together after the Christmas holidays to reflect on their experiences and discuss the thrills and challenges of running bootstrapped SaaS businesses.
The conversation kicks off with a lighthearted discussion about the holiday season and the weather, with each sharing how they spent Christmas. They touch on the feeling of a non-white Christmas, the unusually warm temperatures, and the different local slopes near them for winter sports like skiing and snowboarding.
As they transition into more business-centered topics, the trio reveals their recent work habits. Kevin talks about taking a break and enjoying the holidays, while Steve admits to working a bit, highlighting a night where he made six commits to his project. Jeff, on the other hand, talks about the importance of taking time off and how past workloads have affected his holiday periods.
The conversation delves into what it means to be present with family and the value of memories over constant work, with Jeff sharing insights on the importance of not missing out on family events and experiences.
Kevin considers the stagnant activity in his business and the merits of continuing to work or taking a proper break. He recounts his father's work habits and reflects on how he wants to connect with his children in a meaningful way.
They hit upon the notion of hustle culture versus measured, enjoyable growth. Kevin poses a thoughtful question about what they are building their businesses for, which leads to a discussion about alignment and focus.
Steve talks about journaling and the lessons he's learned from reflecting on past entries, particularly about spending time with family. He reveals his theme for the year is alignment—aligning his actions with what he loves and what helps him grow, both personally and in business.
Jeff mentions the excitement of learning new things in the upcoming year and hints at possible changes in his day job and his commitment to progress with his SaaS venture. He also touches on marketing and the challenges it presents, expressing confidence in his ability to create interesting content but recognizing there's a learning curve to mastering the tools and strategies within the SaaS ecosystem.
As the conversation winds down, the group discusses the impact of AI on SaaS businesses, the emergence of tools like ChatGPT, and how integrating AI may become necessary for staying competitive. Kevin shares his experience with an AI bot for customer support, noting both the benefits and the need for fine-tuning.
The episode concludes with an idea for the next discussion—making predictions for the upcoming year, setting the stage for a future episode where they will revisit their forecasts to see how accurate they were.
Overall, the episode captures the reflective mood of the holidays and sets a tone of mindful progress as the hosts ready themselves for the New Year and emerging technological advancements.
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Founders Gone AIBy Kevin & Steve