Much advice is given hopeful entrepreneurs about how to pitch angel investors, but the truth is that what not to do can be as important as what you should do. I interviewed Sandy Wollman, Co-Founder and Managing Director of Westchester Angels. He is also the star of “Break Through the Crowd,” a new ZEE TV reality pitch competition show about how entrepreneurs inadvertently trigger the quickest “no.” Here are his top three lessons about what to avoid — with memorable examples from his own experience.

1) Attitude Will Get You Nowhere

A charismatic founder is helpful, but a founder with attitude can kill a deal before it evolves. Wollman recalls a recent incident: “We pre-screened a young entrepreneur who was going to provide a service for the Hospitality Industry,” he said. “The pitch outlined the business model, her experience in the industry, and provided a list of her clients to date — all in good form. The glaring omission was any sort of investment numbers that are crucial to the conversation: type of investment being offered (equity or convertible note), current valuation, and exit strategy to start. We started to ask some basic questions and found the entrepreneur’s answers came with a bit of ‘attitude.’ It was as if our questions were not particularly important, and all the info we needed was covered in her pitch! We patiently explained that investors needed more information. My partner then said, ‘We simply want to know how we can make money,’ to which she replied sharply, ‘I suggest that each of you talk with your accountants.’”

That was the end for her. Wollman sums up the encounter with a cardinal rule for founders seeking investors: “Thou shall not insult.”

2) You Need Me More Than I Need You!

Investing is a two-way deal, that some in the investment game equate to getting married. Wollman recalls a time when the wedding was called off because of a lack of mutual appreciation. “I was speaking to a young entrepreneur about his startup. He’d applied to us for funding on for his company that was manufacturing an accessory widget for the tech industry. The application spoke of a patent, so I called him to learn more prior to inviting him to be pre-screened. The entrepreneur started the conversation well, but as I began to ask some basic questions, he became more and more defensive,” Wollman remembers. “He literally out of nowhere screamed, ‘You Angels keep asking the same damn questions over and over! Let me tell you something: you need me much more than I need you! This idea is going to be a big hit and you should be thrilled that I’m even talking to you!’”  Wollman was understandably underwhelmed and not inclined to pursue the deal.

3) The Rocket Man

When a startup founder pitched Wollman his idea of getting satellites into orbit cheaper and more efficiently than those mechanisms that are currently available, Wollman remembers thinking, “Ok, I’m listening!”

“His pitch reviewed his extensive background in space science and technology, while showing detailed plans of his novel idea,” Wollman says. “His secret sauce was that he was going to reuse the rocket! He had gathered some back-of-the-envelope figures on the cost to develop a prototype — and that was about it on the numbers. While he had logos of many S & P 500 Companies as potential clients, the reality was there wasn’t much else for investors to learn. He simply talked about the product rather than the business of the product!”

When asked, “Well, doesn’t Elon Musk reuse his rockets?” this entrepreneur answered, “We will do it better and cheaper!’” So Wollman pressed on, asking how he was going to be cheaper. “The guy then gave a rather technical answer on materials used, cheaper fuel sources, and the like,” Wollman recalls. “Last question: ‘What happens if the rocket sinks to the bottom of the Atlantic Ocean?’ Last reply, ‘We are working on that also.’ That stopped our conversation and we wished him well!”

Having a big dream is essential but you must have the details to back it up. At the end of the day, you are pitching a business, not just a product, service or plan. Investors want to know that you’re thinking about making money for them, and that you are hyper focused on outcomes.

Wollman gets over a thousand “pitches” a year. Take his advice and hopefully you will fare better than the entrepreneurs he recalls here.

@kate_l_harrison is a branding and marketing consultant specializing in nonprofits and sustainable businesses (

-Kate Harrison – Contributor