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I Failed My First Startup — Here's How I Pivoted Without Losing Momentum

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Key Takeaways Build multiple options, so pivots create momentum instead of panic.

Pivot gradually by refining systems and generating revenue at every stage.

I was watching a show about eBay one evening in 1999, and something bothered me. Who does business like this? In real business, you negotiate. You have a price, someone counters, and you find a middle ground where both parties are happy.

The next day, I started Marketcircle.

Originally, Marketcircle wasn’t the CRM it is today. It was a dot-com with a simple premise: put up a product with an asking price, and buyers could counteroffer. We built it, got it working and had actual transactions happening. I even made it to the top VCs in Silicon Valley to raise funding.

The day I arrived, the dot-com bubble burst.

Related: How to Master the Art of Pivoting and Turn Setbacks Into Strategic Advantages

When options create momentum

That failure could have been the end. Instead, it became a pivot point. We went back to consulting. We did this not because we wanted to, but because we needed to keep four people employed and bills paid.

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