The Hardest Startup Leaps

• Free into paid

• PLG into sales-led

• Small business into the enterprise

• International expansion into the U.S. market

These transitions are harder and take longer than expected as many founders think they are further along in the 'latter' as they've seen success/traction in the 'former.'

Success in a non-adjacent market seldom puts you ahead in a new act/territory; in fact, it usually requires unwinding/unlearning before moving forward.

In short, it takes longer to sort product/market fit in this new territory than if you were to tackle it from Day 1. So, don’t kick the can down the road thinking things will get easier.

Many presume these ‘shifts’ into new markets are adjacent in nature, but that’s simply an illusion— they often have competing product needs, market nuance, and go-to-market lift. They often are on opposite sides of the spectrum and require learning a new game.

Here's an example: Small businesses (user/buyer same) like an all-in-one solution and someone who can do a lot of things (breadth). This is directly at odds with what an enterprise buyer wants, which is subject matter expertise (depth, nuance).

Therefore, these leaps require the founder at the helm/driving. The common misstep is delegating ‘new acts’ and throwing bodies and more money at the problem when, in reality, it just needs more founder time and refinement to ensure the vision aligns with the reality of the new market.

In short, founder-led sales never really end as you move into new acts or expansion; it’s an indefinite timeline to continue satiating growth. Your vision must always be refined to the ‘new market’ reality, which should never be delegated.