I’m also on Medium - check that out if you prefer 🙂 also free for you!

This one is about knowing when to pivot vs stick it out. If that doesn't interest you, I'll see you next week - there, just saved you 5 minutes.

In entrepreneurship, the line between stubbornness and pivoting can be dangerously thin.

As ambitious founders chase their dreams, a part of the game is not just in forging ahead but in knowing when to pause, reflect, and realign—skills that are often overlooked yet crucial for long-term success.

I learned this lesson the hard way with my first startup. Like many founders, I had internalized the "never quit" mantra to an almost religious degree. For eighteen months, I pushed forward with an ed-tech platform that I was convinced would revolutionize online learning. The vision was crystal clear in my mind: democratizing education through peer-to-peer knowledge sharing. The only problem? My customers were telling me something else. The only people that worked with me were 1-1 customers who wanted a personal experience.

70% of successful startups make at least one significant pivot during their journey (Source: fundz.net). Even more compelling, startups that pivot once or twice show 3.6 times more user growth and generate 2.5 times better returns compared to those that either never pivot or pivot too frequently (Source: davempayne.silvrback.com).

So let me ask - what do we mean by "never quit"?

The Paradox of Persistence

There's a strange mental conflict in startup culture. We celebrate the stories of founders who persevered against all odds—the Airbnbs and Ubers of the world—while simultaneously knowing that about 90% of startups fail (Source: explodingtopics.com). This creates a dangerous narrative that equates any form of strategic retreat with failure.

What I've come to understand is that "never quit" doesn't mean never changing direction. It means never giving up on solving the problem you've identified, even if your initial solution isn't the right one.

Take the story of Instagram, which began as Burbn, a check-in app similar to Foursquare. The founders noticed that while most of Burbn's features were being ignored, users loved the photo-sharing element. Instead of stubbornly sticking to their original vision, they pivoted to focus solely on photo sharing. The result? One of the most successful social media platforms in history.

The Courage to Change

The hardest part wasn't identifying the need to pivot—it was overcoming my own ego. I had told everyone about my vision, and prospect of admitting I might have been wrong was terrifying.

But here's what I learned: The truly successful founders aren't the ones who never fail; they're the ones who fail fast, learn faster, and aren't afraid to change direction when the evidence demands it.

The New Definition of "Never Quit"

Today, I see "never quit" in a different light. It's not about blindly pursuing a single path; it's about maintaining an unwavering commitment to solving a problem, even if the solution looks different than what you initially imagined.

For entrepreneurs facing this dilemma, here's my advice:

1. Set clear metrics for success and failure beforehand.

2. Listen to your users more than your ego.

3. Remember that pivoting isn't failing—it's evolving.

The most valuable thing you can do is maintain the humility to recognize when your initial approach isn't working, coupled with the courage to change direction while keeping your core mission intact.

After all, true persistence isn't about walking into walls repeatedly—it's about finding the door.

WordRobin Update

We are live - Talking to a founder this weekend showed me Linkedin would be a better fit for Wordrobin.

I am working on integrating triggers - things like breaking news reports, popular tweets, events, and ideas - that can be used to write a Linkedin post about.

We are so close to being good.

What’s next?

It’s all about the (user) journey, baby. Time to build out what the Linkedin integration looks like, and build it. 🙂 

with love, Ben

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