How to Win in Business

5 tips for writing a great cold email from a guy who got Mark Cuban to reply in 20 minutes

Adam Lyons, CEO of The Zebra
Photo courtesy The Zebra

Sending a cold email to someone you don't know can feel like a long shot, and if the person you are reaching out to is famous, it can feel even almost like a waste of time. But for Adam Lyons, the founder of insurance rate comparison start-up The Zebra, a cold email to billionaire investor and owner of the Dallas Mavericks Mark Cuban was life changing.

Lyons dropped out of high-school and was fired from a bunch of low-skilled jobs before he got serious about building a start-up intent on disrupting the insurance industry. He went through a five-month accelerator program in Pittsburgh and then selected, as his dream investor, Mark Cuban.

He decided to make his dream a reality.

Photo by JEALEX Photo

Lyons guessed Cuban's email address, wrote an email to the "Shark Tank" star, and within 20 minutes, he had a response. The two corresponded over email for a few weeks. Despite having never met or talked to him in person, Cuban was impressed enough to invest in the Lyons' project, The Zebra.

Earlier this month, Cuban and Lyons appeared onstage together at the SXSW Conferences and Festival to discuss their relationship and the ways in which Cuban has become a kind of mentor to the younger entrepreneur.

While not every cold email is likely to get you a check from a billionaire, or an on-going relationship with them, here are five pieces of advice from Lyons on how to increase your chances of getting a favorable response.

Keep it short

Chances are a cold email won't get a long, careful read. "I was very short. I was to the point," Lyons tells CNBC. His first email wasn't longer than a paragraph.

A lot of folks want to talk about an idea that they have. Well, everybody has an idea.  You want to talk about what you have done, and the progress you have made.
Adam Lyons
CEO of The Zebra

Be yourself

The subject line of Lyons' email was, "Wanna disrupt the insurance industry?" While that's a casual way to approach a stranger, let alone a billionaire, Lyons says it was important to him to be himself from the very beginning.

"To some extent, particularly with an investor or somebody you are going to work with or you are going to spend a lot of time with, you want to get along with them," says Lyons, so he didn't try to hide his style, even in the first email.

Don't try to close the deal on first contact

When you are reaching out cold, don't front-load your first contact with too large a request.

"I wasn't trying to close him in the email," says Lyons. "Mark Cuban. I am sure he gets thousands of emails a day. If I try to just tell him my entire story and close it, that's just not going to work. The game was, 'Can I just flat out get a response, period?'"

Communicate your excitement

If you aren't passionate about what you are emailing about, then your new contact won't be either.

"If you are dedicating your life to a project, then you are obviously pretty excited about that project and you believe in it, so how would you articulate and share that with somebody? That's the goal," says Lyons. "That's step one."

Then you just have to do it. You can't be afraid. You don't want to overthink it.
Adam Lyons
CEO of The Zebra

Come to the table with work already done

Part of why Lyons got a response from Cuban was that he had perfect timing. Lyons was reaching out to Cuban in 2012 to add technology and transparency to the insurance industry at a time when Cuban thought the market needed just such an innovation. But Lyons had also already done a lot of work by the time he emailed the investor, and he had completed a five-month accelerator in Pittsburgh. That gave him credibility.

"A lot of folks want to talk about an idea that they have. Well, everybody has an idea," says Lyons. "You want to talk about what you have done, and the progress you have made, not what you are going to do as much."

Your goals are important, says Lyons, but in making the initial contact, you want to be able to point to progress already in evidence.

And, at a certain point, you have to hit "send."

"Then you just have to do it," says Lyons. "You can't be afraid. You don't want to overthink it."

See also:

How a 25-year-old high-school dropout cold-emailed Mark Cuban and got an investment

Mark Cuban says that his best life hack is saying yes to email and no to meetings

Mark Cuban: Why I regret not investing in Uber

Mark Cuban: The world's first trillionaire will be an artificial intelligence entrepreneur