What Are The Four Warning Signs You Have A Bad Investor?

brett fox
The Startup
Published in
5 min readSep 13, 2019

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“You truly have the Yin and Yang of investors,” Regis McKenna said to me. Regis was introduced to me by Gill, the “Yang” (bright side) of our investors.

Picture: Depositphotos

But Regis also had worked with “Raul”, the “Yin” (dark side) of our investors. In fact Regis shared story after story, many of them truly hilarious, about Raul.

Regis’ message was clear: Watch yourself with Raul.

At this point in our relationship, Raul hadn’t been very disruptive. That would come later.

However, I’d already seen Raul’s dark side when we were negotiating our term sheet. The terms, to put it mildly, were pretty tough.

Warning sign number one of a bad investor: Bad terms.

Raul was fully aware that we had been raising money for two years, so he knew he had the leverage to force us into a really tough deal. And he did.

He sent the term sheet on Friday, and we had until Saturday at 5PM to agree. Raul and I were scheduled to talk about the terms at 3PM Saturday afternoon.

I called Raul at his home on Maui, and we started negotiating. Or at least I thought we were negotiating.

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brett fox
The Startup

I work with startup CEOs to help them grow their businesses . I built several businesses from $0 to >$100M. Learn more at https://www.brettjfox.com