When pivoting from a product with existing revenue, avoid the binary choice of killing it or splitting focus. Blue Jay successfully transitioned by putting their V1 product into "maintenance mode"—servicing existing customers but halting all new feature development—and committing the entire team to building the V2 for a defined six-month period.

Before a major initiative, run a simple thought experiment: what are the best and worst possible news headlines? If the worst-case headline is indefensible from a process, intent, or PR perspective, the risk may be too high. This forces teams to confront potential negative outcomes early.

StackBlitz launched its pivotal product, Bolt.new, under a new brand because it was a final experiment before potentially shutting down. This strategy protects the core company's brand equity in case the experiment fails and gives the new product a distinct identity to attract a different user base.

Instead of a full rewrite, identify the specific pain points of a legacy system (e.g., a command-line UX) and solve them with minimal development. This delivers immediate value, reduces risk, and validates the market need for a larger investment later, preventing a costly failure.

Adding new offerings is a smart growth strategy, but only if your primary business is stable and systemized. Launching a new service to escape existing chaos will only amplify it. Instead, treat the new offering as a separate, dedicated division to maintain focus and quality.

Instead of "burning the ships," treat potential career changes as experiments. By starting a new venture as a side hustle without financial pressure, you can explore your curiosity, confirm it's a good fit, and build a "safety net" of confidence and proof before making a full leap.

To innovate quickly without being bogged down by technical debt, portfolio companies should ring-fence new AI development. By outsourcing it and treating it as a separate "skunk works" project, the core tech team can focus on existing systems while the new initiative succeeds or fails on its own merits.

Leaders often get paralyzed by GTM decisions, fearing system-wide consequences and accountability. The solution is to reframe decisions as temporary pilots. Instead of a full overhaul, test a new motion with a single Ideal Customer Profile (ICP), learn from it, and then iterate. This lowers the stakes and encourages action.

When testing a new target audience or content style, introduce it as an additional video rather than replacing your core programming. This allows you to experiment with new approaches without threatening the lead flow and revenue generated by your established, successful content.