If, when, and how to Pivot: Lessons from 8 Pivots in 14 Months

Few decisions are more difficult than deciding when to keep going vs when to pivot. There are many success stories on either side.

I discussed this with Han Wang, Co-Founder and CEO of Mintlify who pivoted 8 times during their first 14 months before finding product-market-fit with a developer documentation platform.

Here's how he thinks about it:

Every startup starts with an initial idea and product. If things don’t blow up, they start to iterate.

Too often, "iterations don't fundamentally change the product by an order of magnitude."

For Mintlify, it looked as following

Their initial AI tool for explaining code went viral on Product Hunt with 5,000 signups on day 1.

Soon after, they learned that virality doesn't equal retention. Usage steadily declined.

They spent 2 months trying to improve without success. Adding features doesn’t fix lousy retention. Tweaking onboarding won't make non-buyers buy.

Dead products need new ideas, not bandaids. Thus, they decided to pivot for the 1st time.

7 pivots later, Han now has a strong point of view re when to to pivot.

Keep going when you have:

• Specific ideas to improve metrics

• Retention that's climbing (even slowly)

• Users pulling the product forward

• Genuine belief in the direction

Pivot when:

• You're out of meaningful ideas

• Retention is flat after multiple tries

• You're adding features randomly

• You dread working on it

Pivots aren’t easy. For Han it

"literally felt like chewing glass for about 14 months."

The emotional cost is real. But manageable with the right approach:

1. Time box experiments: Give ideas weeks, not months, to show promising signs of life. Speed is everything.

2. Set exit criteria upfront: "If we don't hit 40% retention, we pivot." No negotiation.

3. Define each hypothesis in one sentence: Complexity is procrastination.

4. Track patterns across failures: What worked? What didn't? Why? Always collect the next idea while building the current one.

5. When you feel it’s time to pivot, do it immediately: Don't drag out the death.

Now, if you’re on the right path, you’ll know. The contrast is unmistakable when you find it:

Instead of

• "I'll think about it," you hear "Take my money."

• Lukewarm interest, you get urgent implementation requests.

• Scheduled follow-ups, you get angry emails about downtime.

• Feature requests, you get complaints if your infrastructure can’t keep up.

As Han puts it:

"When you've tried many products and did many iterations that didn't work, when something does, it's night and day."

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Enjoyed reading this?

Then check out my conversation on the focal podcast with Han Wang, the Co-founder & CEO of Mintlify, who truly knows IF, WHEN, and HOW to pivot with speed and conviction. A lesson he learned the hard way: Mintlify pivoted 8 pivots in 14 months before finding Product-Market-Fit.

Youtube | Apple Podcast | Spotify

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