Entrepreneur And Media Personality Michael Gruen On The Power In Cold Emailing, Connecting

Cold emails are underrated.

That’s according to Michael Gruen, an entrepreneur, angel investor, consultant and media personality.

Called “one of the most mysterious, obnoxious, interesting humans who ever walked the world,” by Barstool Sports founder Dave Portnoy, Gruen is heralded for his network of celebrities.

In a conversation with Benzinga, Gruen spoke about his origins, as well as tips for scaling networks to grow brands. The following is part 2 of an exclusive series on Gruen.

The Value In Email: Too often, the value of cold emailing is discounted because the solicitor has no relationship with the audience, and there's no real-time feedback. However, cold emails are powerful. They helped Gruen build his career and relationships, invest, as well as launch new companies.

“The value of the cold email is so underrated,” he said. “For example, I got a meeting with the chairman of NBC when I was like 15, just by cold email. From there, if they like you, and you do a good job, they’ll introduce you to others.”

Regardless of age and experience, when worded properly, cold emails are respected for being straightforward and unobtrusive.

“When you’re 13, and you’re writing emails and hustling, people pay respect to it. Also, I think people underestimate people’s desire to help.”

Cautionary Advice: Gruen stressed the importance of providing value to others.

“People don’t like emails that ask for things," he said. "I found that when I’m very open, even if I don’t know somebody -- I’ll send them an email saying we’re not looking for anything, we just want to chat, pick your brain, and learn from the best -- sometimes good things come out of it.”

When conversations don’t go as planned, Gruen takes it as a learning experience: “People underestimate the value of knowledge, and everything is about conversion. In reality, knowledge leads to conversion. The more I’ve learned, the more I’ve been able to convert.”

In an example on how to provide value, Gruen discussed prior connections he’s made.

“I got a call with the co-founder of Netflix, Marc Randolph,” he said. “I later looked at his socials and saw he wasn’t verified. Ten minutes later, he was verified on Instagram. A week later, he was verified on Twitter. He was like, ‘I’ve asked a hundred people, and you were the first one to do it.’”

In another example, Gruen connected ex-TikTok CEO Kevin A. Mayer with Taylor Fritz, a top tennis player that was interested in technology investing.

“I met Kevin, and I knew he was a tennis man because his house has a tennis court. I was sitting with my friend Taylor who's been trying to get into tech investing,” Gruen said. “So I was like, ‘I got it’ and Taylor sat with Kevin at his house. They played tennis together and talked tech, killing two birds with one stone.”

In the end, all parties are happy. Fritz and Mayer learned more about each other, while Gruen took satisfaction in that he was able to strengthen his relationship with two friends.

Gruen added, “The bigger thing is to do things on the spot -- don’t ever let it wait -- when I tell someone I’ll make an intro, I do it on the phone. Also, don’t be the middleman, because it looks power hungry and people take note.”

In simpler words, do things out of kindness, immediately, with no strings attached.

One Big Thing: Getting to yes is difficult, Gruen says.

“One of the tricks I learned early on was, I’d email someone, and they’d be like, ‘Oh, let me know when you’re in Miami, and I’d respond with, ‘Oh, coincidentally, I’m in Miami tomorrow,’ and I’d just book a flight.”

Gruen did the same trick when scheduling an interview with Ron Meyer, who was the Chairman of NBC at the time.

“I cold emailed him, and he was like ‘Yeah, let me know when you’re in L.A.’ I was like I’m there tomorrow, and I booked the ticket.”

The experience turned out to be one of the most impactful ones for Gruen.

“I sat down with him in his office, and that meeting really shaped my view on entertainment because he gave me some amazing perspectives,” he said. “It made me feel like I’m working toward something because I saw him in person, and saw what he built, and kind of where it led him.”

“I’m 15 years old, sitting with the chairman of NBC who’s greenlighting every movie in the world. It was pretty crazy.”

In part 3 of this series, Benzinga will unpack Gruen’s interesting networking stories and making an impact in business.