The Freedom of Unstructured Entrepreneurship

Jason Jacobs wants it all. 

As a father to young children, he wants to be active in their lives, but as an ambitious founder, he’s compelled to build and chase down opportunities that often require sacrificing the time with his family that he longs for. This is not a new tension for a repeat founder, but the current moment has presented Jason with an opportunity to reflect and explore whether the new tools and timing available today may make this next time... different. 

I first met Jason when we funded his startup, Runkeeper, the first fitness tracking app for the iPhone. It was a fascinating ride for the both of us as Jason piloted a rocket ship whose engine stalled as he pushed to tell a story that made investors swoon and customers scratch their heads. Runkeeper ended as a success via its acquisition by ASICS in 2016 and started a new chapter for Jason as a successfully exited founder. 

After a false start raising money for his first idea post-Runkeeper, Jason began to develop a process for discovering what comes next for him in his pursuit of entrepreneurial purpose and impact. He applied this process first in climate, ultimately founding the venture capital firm, MCJ. Recently, he’s begun the process again with The Next Next which he describes as:

My hope with this expedition is I can unpack what we as humans need out of work in this next era, what is possible with emerging tools, and how they can be applied most effectively to building startups. I am hoping it will lead to my next venture (iteratively, using this newsletter as an important feedback tool), and that if I find success with this new playbook, it can be a template for a new way of company building that many others will follow.

Some takeaways from this conversation:

- Chasing trends or investor expectations at the expense of your core mission can derail even a promising startup. Jason candidly admits that Runkeeper lost its way when it tried to expand beyond its core running focus into the broader “Health Graph” vision. This pivot, driven by the allure of venture capital and external validation, created internal friction and diluted the company’s identity.
- Realigning your business with its foundational strengths when navigating challenges. Jacobs’ decision to refocus Runkeeper on its original running mission marked a turning point for the company. By cutting unnecessary initiatives, streamlining operations, and regaining profitability, the team was able to position itself for acquisition by ASICS.
- The importance of “staying true to your weirdness” and building in a way that aligns with your values and strengths. Whether it’s rejecting the grind culture of traditional startups or refusing to compromise on family priorities, his journey highlights that success doesn’t have to come at the cost of personal fulfillment. For Jacobs, autonomy is not just a preference—it’s essential for achieving greatness.
- Learning in public as a superpower. After Runkeeper, Jacobs embraced the power of learning in public by sharing his explorations into climate tech and, later, AI through newsletters, podcasts, and social media. This approach not only helped him build credibility in new fields, but also attracted like-minded collaborators who became part of his growing tribe.
- Jason is now on a mission to prove that it’s possible to build impactful companies without sacrificing family, health, or balance. Leveraging AI tools to reduce operational overhead, he aims to build differently while maintaining control over his time and energy.

I have an expansive relationship with Jason, and I think that comes through in the video. We cover much of the struggles he had with investors, managing his psychology as a founder, and his process of discovery that he has unquestionable conviction in. 

My hope is that people will see some of themselves at various stages in Jason’s journey and find inspiration in both his mission and his process. 

I hope you enjoy watching as much as we enjoyed recording it.