Recognizing the Right Moment to Change Course in a Startup
I recently had the pleasure of joining David Lovejoy and Becky Hayman of Horizon Search for a podcast conversation about my career, investing, and the founder journey. Near the end, Becky asked a question that stuck with me:
“When should a founder admit their concept isn’t working—and try something else?”
It’s one of the most important (and most misjudged) decisions a founder can make.
The Optimism That Fuels—and Sometimes Fools—Us
Founding a startup requires a special kind of optimism. You need vision, grit, and unwavering belief—especially in the early days when few others see what you see. That conviction is often what gets a company off the ground.
But the same belief that powers a startup can also become its blind spot.
Knowing when to pivot—when to step back and admit that the current approach isn’t working—is difficult. It can feel like betraying your original vision, your team, your investors. And in a startup culture that lionizes perseverance, it’s easy to confuse persistence with inflexibility.
The Myth of the Relentless Founder
Startup folklore loves stories about founders who pushed through 100 rejections before finding product-market fit or raising a first round. They’re inspiring—but they also paint an incomplete picture.
What gets lost is the nuance: grit is essential, but so is adaptability.
The founders behind companies like Twitter, Slack, Pinterest, and Instagram didn’t “stick it out” on their original ideas. They listened to the market and changed course—sometimes more than once. Their success came not from stubbornness, but from timing a pivot with clarity and conviction.
How to Know When It’s Time
So how do you recognize when a pivot—or a full reset—is the right move? Here are some key indicators:
1. Consistently Poor Traction
If engagement is low, sales aren’t growing, and metrics are flat despite genuine iteration and effort, the issue may not be execution. It may be the underlying idea.
You may be solving a problem that’s not urgent—or not painful enough—for customers to pay for. That’s not a tweakable issue. It might not be a pivot opportunity. It might be time to rethink the entire premise.
2. The Product Doesn’t Actually Solve the Problem
You may have nailed the right problem, but missed on the solution. That can happen when the product doesn’t match how customers experience the pain point—or when price, UX, or positioning are off.
In this case, a pivot could mean reworking the product, reframing the value proposition, or changing how you deliver the solution.
3. Aligned Feedback from Trusted Voices
When multiple advisors, investors, or team members raise the same concerns—especially around missed milestones—it’s worth listening. Not all feedback is equal, but when signals align from people who care about your success, pay attention.
Don’t brush off hard truths as “negativity.” Often, they’re early warning signs.
4. You’re Losing Conviction
Many founders avoid this one, but it’s critical. If you find yourself dreading product meetings, struggling to pitch, or quietly hoping you won’t land a new customer, that’s not just burnout—it may be your instincts telling you the idea no longer holds up.
Listen to that voice. It’s often more honest than your roadmap.
Pivoting Is Not Quitting
Let’s be clear: pivoting is not failure.
It’s often the most strategic decision a founder can make. It shows you’re paying attention—to data, to customers, to what the market is really telling you. And it signals to investors and your team that you’re in this to win, not just to be “right.” For instance, Pinterest was on their third or fourth pivot when they achieved the product-market fit that made them a unicorn.
The key is to act with intention and urgency.
A note about the image. I created this image using DALL-E 3. This is apparently the newest and most powerful iteration of DALL-E and is integrated into Chat GPT. My prompt was to show a frustrated business person banging their head against the wall. I didn’t specify man or women. The first iteration showed a man in a suit. I didn’t think that was right for an article about startups. My second prompt asked for someone in business casual–which worked better. I tried a third time for a more photorealistic image but got nothing interesting.