What if everything you know about pivoting your business is wrong?
In this eye-opening episode, we dive deep with serial entrepreneur Jason Sherman to unravel the true nature of strategic pivots. Discover why most founders pivot too soon, how to properly evaluate your assets before making a change, and the surprising truth about when to hold steady versus when to evolve. Sherman shares battle-tested insights from multiple successful pivots, including how he transformed a video friendship app into a thriving AI business.
The pivot paradox isn't really a paradox at all – it's a natural part of business evolution. Success lies not in avoiding pivots but in executing them strategically. Before making any dramatic changes, founders need to understand the three key indicators that signal potential pivot time: personal frustration level, investment climate, and customer traction. When these three pillars start wobbling simultaneously, it's time to take a hard look at your direction.
But here's where most founders stumble: they pivot based on internal frustrations rather than external opportunities. Instead of just reacting to what's not working, scan the horizon for what's emerging. Look for unsexy markets that bigger players ignore. Seek out antiquated systems begging for disruption. The best pivots aren't just escapes from failure – they're calculated jumps toward opportunity.
Before you blow everything up, consider the power of incremental shifts. Sometimes what looks like a business model problem is actually a messaging issue, or what feels like a product failure is really just a misaligned sales strategy. Test small changes first – tweak your target market, adjust your pricing, or modify your feature set. These micro-pivots can often reveal the path forward without requiring a complete reinvention.
Watch the Full Episode on The Pivot Paradox with expert Jason Sherman below: