On Wednesday, April 14th, 2021, Jason Jacobs joined High Alpha Partner Mike Fitzgerald for a virtual fireside chat about founding Runkeeper and his quest to address Climate Change with his unique skill set as a long-time software entrepreneur.
When Jason started Runkeeper in 2008, it was one of the first 200 apps listed in Apple’s App Store. The running app quickly became one of the world’s largest fitness communities and was later acquired by ASICS in 2016.
Post-acquisition, Jason turned his attention to climate change and understanding how he could address the problem. Today, he’s a venture investor and the host of the My Climate Journey podcast dedicated to those seeking to understand climate change better and how to help.
While we could unpack a lot from Jason and Mike’s insightful conversation, these are the three key pieces of advice I think every software entrepreneur can learn from.
1. Don’t Be Afraid to Focus and Work on What Energizes You
Post-acquisition, Jason felt pressure to start another software company, but he was more interested in unpacking climate change. Even though he wasn’t sure how he could help, Jason shifted his career around following his new passion and did everything he could to learn about the issue. Ultimately, his conversations led to the My Climate Journey Podcast and investments in technology addressing the challenges of Climate Change.
The lesson? Find what energizes you and pursue it. If you’re successful as an entrepreneur in one space, it’s only natural that you might feel pressured to continue working in that industry. But Jason’s story tells us that expertise or knowledge is only one part of the equation — and that passion, many times, is just as important.
2. Don’t Overlook the Importance of Trusted Advisors and True Partners in Your Business
Throughout his journey with Runkeeper, Jason had to make several difficult decisions. One example he shared included shifting his revenue model. After initially selling Runkeeper in the App Store as a paid app, they chose to shed 90% of the revenue by making the app free to download and created a subscription model. Thanks to the support and mentorship of trusted advisors and his initial investors, he was able to take this calculated risk.
For entrepreneurs, making hard business decisions is part of the job. By surrounding yourself with advisors you can trust, you can gather insight into what they’ve seen work — or not work — in the past. Find advisors, investors, and partners that can grant you access to alternative perspectives and ideas.
3. Building a Successful Startup is Unpredictable — It’s Normal to Question Yourself
The stories of entrepreneurs with successful exits often only cover the best moments. Never the pivots, imposter syndrome, or uncertainty that make us all human.
In his conversation with Mike, Jason was incredibly candid about the actual journey of entrepreneurship and how the path is never clearly defined. For example, when Runkeeper was acquired by ASICS, instead of feeling happy or proud, Jason shared that he felt somewhat unworthy. There was very little liquidity before the acquisition, and in his mind, the success felt somewhat lucky.
As someone new in my career, Jason’s candid reflection was refreshing. It showed me that even those who achieve an outcome deemed a “success” can feel self-doubt.
For the entrepreneurs reading this, you will also feel self-doubt or imposter syndrome along your journey. It’s essential to remind yourself that this is normal, something all entrepreneurs experience, and a part of being human.
If you missed the event, you can watch the entire conversation with Jason here. Every month, we sit down with leaders and entrepreneurs like Jason and dig into learnings from their backgrounds and careers. Make sure to subscribe to Speaker Series to attend upcoming events.