What is the most frustrating part of the startup journey if you’re unprepared?

In one word: Iterations.

There is relentless iterating and testing of new ideas in a startup. Be it product, or a distribution channel or market positioning, you have to be willing constantly keep experimenting with new unproven ideas.

This might sound extremely disappointing if you approach it with a stability-seeking mindset. There’s no certainty and stability in startups.

Huge companies mitigate this flux/change by over-indexing on the methods and ideas that worked in the past for them. Therefore, they manage to keep everything under control “for a while” and reduce change. But the downside is they are not innovating as much either. So you won’t feel the pressure until you are almost on the verge of extinction. This turns once great companies into outdated relics. (Kodak, Nokia, Blockbuster, MySpace etc)

Startups, however, are like pedaling boats in the sea (as opposed to the massive cruise ship corporations like The Titanic).

I’ve been re-reading the all-time classic startup book “The Lean Startup” by Eric Ries where he presses on the topic of pivots many times. He shared a story about one company called “kaChing” that pivoted 4 times before they found their product-market fit.

You should check out this excerpt from his blog that details the story full of twists and turns. What’s funny is that it doesn’t end there. After the blog post was written, they eventually pivoted and re-branded themselves to Wealthfront.