This 23-Year-Old Entrepreneur Emailed Mark Cuban, Sheryl Sandberg And Adam Grant, And They Responded. Here’s Her Simple Cold Emailing Advice.

Founder of GirlZ, a youth marketing consultancy focused on helping brands better connect and engage with today’s youth, Maddie Bregman has worked with some well known brands including Gatorade, NFL, Nickelodeon, PepsiCo, Burger King and Chipotle. Her professional journey began in 2017 with a connection she made with a single cold email. Since then, motivated by that initial success, she has consciously curated and refined techniques for crafting cold emails that cut through the noise and get noticed. Then, in 2020, Maddie gave a TEDx talk titled “The Power of the Cold Email,” highlighting how cold emailing had shaped her career.

The great news about Bregman’s success is that her approach can be duplicated using a few simple cold emailing tips.

Keep it short and don’t sell

It’s important to remember that executives and influencers with the most visibility and responsibility are already inundated with emails and have the least disposable time so if you want to boost the likelihood of your email actually being read, keep it short and focused. “Keep the sentences short and space them out,” Bregman explains. “This makes it easier to read.” She also reminds us that selling almost always repels the reader, and as such she warns against trying to sell anything in an initial email. “Don’t try to give your sales pitch in a cold email,” she insists. “The goal of the first email is to get someone’s attention and spark interest.” (More on how to do just that below.)

Don’t ask to “pick someone’s brain.” Instead, ask a very specific question.

While it may be tempting to think that busy executives are sitting around hoping random strangers will reach out to ask for free advice, that’s far from reality. Given the fact that—just like most of us—executives and influenceers struggle to get their daily to-do list done, a random invitation from a stranger interested in “picking their brain” is beyond a buzzkill. “Asking to ‘pick someone’s brain’ or to get coffee is something a lot of people do and often won’t elicit a response,” she explains. “These people get asked for things all the time and generally don’t have time to get coffee with someone they’ve never met.”

Instead, Bregman suggests asking them a very specific question. “For example, when preparing for my TEDx talk I asked people for advice on public speaking,” she explains. “Mark [Cuban] told me that he loved being the youngest person in the room, to own it and to use it to my advantage.” McArthur Fellow and author of the New York Times bestseller Grit: The Power of Passion and Perseverance, Angela Duckworth advised, “Tell a story that has a beginning (suspense), middle (vulnerability), and end (lessons learned).” In addition to suggesting that she tell stories during her talk, ThirdLove CEO Heidi Zak advised, “Be yourself (i.e. use your hands, have energy, etc.) Don’t try to be someone else.” By asking a very specific question, she not only got amazing advice from well-respected, busy business powerhouses, with each response she established an incredibly valuable connection.

Email the right person

If you have an amazing cold email message, don’t make the common mistake of sending it to the wrong person. Busy professionals are rarely going to take the time to forward a cold email up the food chain or over to a different department or key influencer to help you get the right exposure so do your research and make sure you’re reaching out to the person who is most relevant to your ask and best positioned to address your issue. It’s no secret that finding the right contact can be an uphill battle, but Bregman advises that it’s worth the effort. LinkedIn can certainly be a great resource for finding accurate contact information. Hunter.io, rocketreach.co and the Clearbit extension are also among the resources that Bregman uses.

Don’t underestimate your ability to make contact

Ultimately, one of the most common mistakes you can make related to cold emails is simply not hitting send—assuming cold emails are a complete waste of time. While response rates may indeed be low, done right they can spark real connection. “I’ve had people I never thought would respond to me respond, which has been awesome,” reflects Bregman. When she reached out to Lean In author and Meta (owner of Facebook) COO Sheryl Sandberg, the billionaire didn’t just respond. She also sent Bregman a personally inscribed copy of her New York Times best seller along with some cool Lean In swag. Bregman’s cold email to co-founder of Summit Group, Elliott Bisnow ultimately resulted in an informative hour-long FaceTime chat. “He gave me a lot of advice that I still use today,” Bregman reflects.

Without question, cold email response rates are notoriously low and cold emailing is certainly not the only, or even the best, method for establishing a professional relationship, but it can work. Without question, Maddie Bregman has received counsel from some of the most influential names in business, and it didn’t cost her a cent. It did however require intention, persistence and patience along with carefully refined skill in the fine art of cold emailing.

The best news is that anyone can use her tips. You never know. Personalized advice from Barack Obama, Oprah Winfrey or Jeff Bezos just might be a click away.