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Sherman: Angel investors refused a refund 30 days into Spotfronts

Alex Sherman · He tried to return $200K to investors 30 days in—then exited to Microsoft 5 years later. | Alex S... · PMF Show · Oct 6, 2025 · at 4:44

Alex Sherman, co-founder of PromoteIQ (later acquired by Microsoft), recounts trying to return angel funding 30 days into his first startup, Spotfronts.

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“And basically within 30 days, we were like, oh, this is completely wrong. This is the wrong idea, the wrong execution. Like this will never work. And I will never forget this. I called all of our angel investors who had like sort of soft circled money for this angel race. And I was like, I'm giving it all back. Like, don't send us the money because we're wrong. And these were all professional angels that had written, you know, hundreds of checks like this. And they were like, no, no, no, no, that's not how this works. Like you're taking the money, go figure out what to do with it. We're betting on you guys. We're not betting on this sort of the one idea, go figure it out.”

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