My two cents from six pivots, and a framework for making the toughest decision.
Nine months ago, I had to make a hard decision: Pivot.
We killed Switchboard.app, a cloud collaboration platform that we'd poured our hearts into, and pivoted to Airtop, a new kind of web automation platform.
It wasn't the first time. As a six-time founder, I've actually had to pivot each one of my companies. I guess I'm just not the kind of entrepreneur who starts with the right idea... Some of these pivots were wildly successful. Others were catastrophic failures that cost us years and millions.
Today, I can confidently say the Switchboard-to-Airtop pivot was the right call. But at the time? It felt like we were abandoning everything we'd built.
If you're like me and like most founders, you will face this question: Should I pivot or should I persist? So I tried to summarize my learnings and provide a structured way to think about it. I hope you'll find it useful.
Why Timing Is Everything (And Why Most Founders Get It Wrong)
Here's the brutal truth from six pivots: I've never pivoted too early.
Most founders make the same mistake—they pivot too late, not too soon. We cling to our original vision long after the market has told us it's not working. We confuse persistence with stubbornness, and by the time we finally make the call, we've burned through resources, team morale, and precious runway.
The fastest pivot I ever made happened 3 months into a company. The slowest? 3 years in, when we'd already raised over $40M and had 40 employees. Guess which one was harder to recover from?
The pivot penalty compounds over time. Every month you delay makes the decision exponentially more expensive—financially, emotionally, and strategically. The later you pivot, the more you have to unwind, the more people you disappoint, and the less energy you have for the new direction.
But here's what makes timing so tricky: You need enough data to make an informed decision, but not so much time that you're trapped by sunk costs. The sweet spot? Earlier than feels comfortable.
The Dangerous Middle Ground
Here's what nobody tells you about building a startup: The danger zone isn't failure—it's the messy middle where success feels just out of reach.
You're not failing spectacularly (that would be easy to diagnose). You're not succeeding wildly (that would be obvious). You're stuck in entrepreneurial purgatory, wondering if you're one feature release away from success...
Most advice on this topic is useless. "Follow your passion!" "Listen to the data!" "Trust your gut!"
Founders don't need platitudes. They need a framework.
The COMPASS Framework: Your Decision Filter
After analyzing dozens of pivot decisions (both successful and not), I've identified six critical factors that separate smart pivots from stubborn persistence:
C - Customer Pull vs. Customer Push
Persist Signal: Customers are pulling your product from you, asking for more features, higher usage limits, expanded access
Pivot Signal: You're constantly pushing your product onto customers, justifying its value, explaining why they need it
O - Objective Market Feedback
Persist Signal: Market metrics show consistent growth, even if slower than hoped
Pivot Signal: Metrics have flatlined for 6+ months despite significant effort and iteration
M - Money Trail
Persist Signal: Someone (other than your mom, friends and accelerator buddies) is willing to pay, even if it's not enough people yet
Pivot Signal: You can't get anyone to pay anything, or payment comes only after heavy convincing
P - Personal Energy
Persist Signal: The problem energizes you; you wake up excited to solve it
Pivot Signal: You dread Monday mornings; the problem feels like a burden
A - Assumptions Validation
Persist Signal: Core assumptions are proving true; you're optimizing execution
Pivot Signal: Fundamental assumptions about market need or customer behavior are consistently wrong
S - Sunk Cost Honesty
Persist Signal: You'd start this exact business again knowing what you know now
Pivot Signal: You're only continuing because of time/money already invested
S - Story Integrity
Persist Signal: You still believe the story you're telling investors and employees; it energizes them and you can defend it with conviction
Pivot Signal: You've stopped believing your own narrative; you're going through the motions of a story that no longer feels true
The 3-3-3 Rule
Before making any pivot decision, apply the 3-3-3 Rule:
3 Weeks: Can you implement one major change that might move the needle?
3 Months: If you gave this your absolute best effort for 90 more days, what's the realistic best-case outcome?
3 Years: Where does this trajectory lead if everything goes moderately well?
If the 3-year answer doesn't excite you, pivot. If the 3-week answer gives you hope and the 3-month answer shows meaningful progress potential, persist.
The Billion-Dollar Pivots (And Persistent Wins)
Twitter started as a podcast platform. Instagram began as a location-based check-in app. Slack was originally a gaming company.
But Amazon took 7 years to become profitable. Tesla nearly died multiple times. Airbnb was rejected by every investor and sustained themselves selling cereal.
The difference? The successful pivots changed direction but stayed true to their core insight about human behavior. The successful persisters stayed true to their vision but adapted their execution.
Your Action Plan
This week, ask yourself:
When was the last time a customer surprised you with how much they loved your product?
What would you do if this exact problem disappeared tomorrow?
Are you solving a vitamin problem (nice to have) or a painkiller problem (must have)?
Then score yourself on the COMPASS framework (1-10 for each factor).
Score 50+: Persist with conviction
Score 25-49: You probably need to pivot your approach, not your vision
Score Below 25: Time for a real pivot
The Hard Truth
Most founders pivot too late or persist too long because they're afraid of admitting they were wrong. But here's the paradox: The faster you're willing to be wrong, the faster you'll be right.
The best founders I know treat pivoting and persisting not as permanent decisions, but as data-driven experiments with clear success metrics and timelines.
