Jason Shen: The Path to Pivot

“A pivot really is a second chance,” says Jason Shen, author of “Path to Pivot.” In this episode, Alex Raymond talks with Jason about the critical decision-making process of whether to continue, pivot, or close a business. Shen emphasizes leveraging assets and insights to create a market advantage, highlighting the rarity and value of a well-executed pivot.

Jason recounts his shift from writing about resilience to focusing on pivots, inspired by his experiences with his Y Combinator-backed companies, Ridejoy and Headlight. While Ridejoy’s pivot failed, Headlight’s pivot led to a successful exit to Facebook, forming the foundation of his book.

The episode delves into the mental and emotional facets of pivoting, introducing Jason’s “Align, Explore, Commit” framework for systematic pivoting. Jason and Alex also discuss “shooting the zombie,” the tough call to pivot or close a business that can’t meet venture capital expectations. 

Insightful anecdotes and practical advice make this episode a valuable guide for entrepreneurs facing pivotal decisions with resilience and strategic thinking.

Jason is offering listeners of The Conscious Entrepreneur Podcast a discount code for 50% off any version of The Path to Pivot ebook. Just head over to https://jasonshen.gumroad.com/l/path-to-pivot and use code CONSCIOUS to get 50% off.


  • “If you’re at your wit’s end, if you really have no idea where to go, if the walls start to close in, then maybe a dramatic shift may be more important. And that’s where a pivot comes into play. A pivot is to say ‘What if we change the fundamentals of this business?’ Keeping some parts the same, maybe the team is the same, maybe the product is the same, maybe the market is the same, but you make some other dramatic shift. You go from selling it one time to a lower monthly fee. A business model change is still a pretty meaningful change.” (14:43 | Jason Shen) 
  • “A good pivot is always based on some kind of new insight. It involves learning something from the world that you’ve already been operating in that certainly gives you a leg up, an advantage, and that’s what you have. You’re able to shift your product, but position it for a new problem, position it for a new market, but sort of retain a lot of the experiences that you’d built, which is super important.” (22:12 | Jason Shen) 
  • “You have to have insights based on what you’ve developed as a business and assets that you’ve developed that can create some kind of advantage for you so that you can actually win in this market and sort of earn the right to keep playing this game. And the reality is, it takes time to build anything. It takes time to even make an attempt at anything. And so, a pivot really is a second chance.” (32:55 | Jason Shen)


Connect with Jason Shen:

LinkedIn: https://www.linkedin.com/in/jasonshen/

Website: https://www.jasonshen.com/

The Path to Pivot: https://jasonshen.gumroad.com/l/path-to-pivot

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://consciousentrepreneur.us/

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