How an 18-Year-Old Uncovered Tim Ferriss's Secret Cold Email Template to Reach CEOs and VIPs

Never email someone and ask to 'jump on the phone,' 'get coffee' or 'pick your brain.'
How an 18-Year-Old Uncovered Tim Ferriss's Secret Cold Email Template to Reach CEOs and VIPs
Image credit: Cindy Ord | Getty Images

Grow Your Business, Not Your Inbox

Stay informed and join our daily newsletter now!
Author and Keynote Speaker
7 min read
Opinions expressed by Entrepreneur contributors are their own.

My journey began when I was an 18-year-old college freshman. The day before my final exams, I hacked The Price Is Right, won a sailboat, sold it and used the prize money to fund my quest to learn from the world's most successful people. I secured this interview with bestselling author Tim Ferriss only after I crouched in a bathroom for 30 minutes, waiting for Ferriss to walk by. I then sent Ferriss's assistant 31 overly eager emails to confirm the interview and, well, you'll see how it played out ...

I was finally on the phone with Tim Ferriss, my notepad full of questions. Not surprisingly, the first one was about persistence.

Related: If You Want to Actually Get a Response to Your Email Pitch, Here's What You Need to Do

I'd read a brief mention in The 4-Hour Workweek that Ferriss got his first job out of college by emailing the CEO of a startup over and over until he got a position. I wanted to know the full story.

"It wasn't just one-two-three and then you're hired," Ferriss told me.

Toward the end of his senior year in college, Ferriss did his final project on that startup in an attempt to build a relationship with its CEO, who'd been a guest speaker in one of his classes. But, when he mustered the courage to ask for a job, he was turned down. Ferriss sent the CEO more emails.

After the CEO said no a dozen times, Ferriss decided it was time for a Hail Mary. He emailed the CEO saying that he'd "be in the neighborhood" next week -- even though he was in New York and the CEO lived in -- and said it'd be great to stop by. "All right," the CEO wrote back. "I can meet you on Tuesday."

Ferriss got a standby ticket, flew to California and arrived at the startup's office early for his meeting. One of the other executives asked him, "So, you're not going to stop bothering us until we give you a job, huh?"

"Sure," Ferriss told him, "if you want to put it that way."

He got the job -- and, naturally, in sales.

Related: How to Cold Email a Stranger for Advice

"It's important to note," Ferriss told me, "that I was never rude. I also didn't push the density. It's not like I emailed him six times a week."

Ferriss's tone shifted, as if he was hinting at something, though embarrassingly, I couldn't figure it out. But, I could sense something was off because his tone was making my head snap back as if I was getting punched.

"Where do you think that fine line is?" I asked.

"If you sense someone getting annoyed, you need to back off." Jab. "You need to be polite and deferential and recognize that, if you're emailing someone like that, you should have your hat in hand." Jab. "There's a fine line between being persistent and being a hassle." Uppercut.

If I had more experience interviewing, I would've dug deeper to uncover what Ferriss was trying to tell me. Instead I just fled to safer ground, looking down at my notepad in search of a different topic.

Related: This Is The Cold Email I Used to Connect With C-Level Execs at 22 of the World's Biggest Companies

"How did you gain before you were a well-known author?"

"Well, volunteering for the right organizations is an easy way to get some credible association," Ferriss said.

His tone lightened and I relaxed. Ferriss explained that when he was an entry-level employee, he volunteered at the Silicon Valley Association of Startup Entrepreneurs where he produced large events, giving him a credible reason to email successful people. Rather than saying, "Hi, I'm Tim Ferriss, recent college graduate," he could say, "I'm Tim Ferriss, an event producer with the Silicon Valley Association of Startup Entrepreneurs." That legitimacy made a big difference.

"A second step would be writing for or being featured in known publications," he continued. "And that could be as easy as doing a Q and A with someone -- interviewing them and publishing the answers online."

In other words, Ferriss didn't build credibility out of thin air, but borrowed it by associating himself with well-known organizations and publications. The phrase "Borrowed Credibility" stuck in my mind.

Related: How I Generated Over $20 Million in New Business Using Cold Email Outreach

When Ferriss began writing The 4-Hour Workweek, he said, he had no prior experience in publishing, so he cold-emailed authors asking for advice. He said it worked well, so I asked for cold email tactics.

"The general composition of my emails," Ferriss said, "when I'm emailing a busy person, is:

Dear So-and-So,

I know you're really busy and that you get a lot of emails, so this will only take sixty seconds to read.

[Here is where you say who you are: add one or two lines that establish your credibility.]

[Here is where you ask your very specific question.]

I totally understand if you're too busy to respond, but even a one- or two-line reply would really make my day.

All the best,

Ferriss was giving me exactly the kind of advice I craved. He told me to never email someone and ask to "jump on the phone," "get coffee" or "pick your brain."

Related: 5 Essentials to Writing Cold Emails That Convert Prospective Clients

"Put your question right in the email," he said. "It might be as simple as, 'I'd like to discuss a relationship of some type that could take this-and-this form. Would you be willing to discuss it? I think a phone call might be faster, but if you prefer, I could throw a couple of questions your way via email.'

"And never write lines like, 'This is perfect for you,' or 'You'll love this because I know this-and-this about you.' Don't use superlative or exaggerated words because" -- he let out an almost mocking laugh -- "they don't know you and they'll assume, quite fairly, it's hard for you to determine if something's perfect for them.

"I'd also not end with something like, 'Thanks in advance!' It's annoying and entitled. Do the opposite and say, 'I know you're super busy, so if you can't respond, I totally understand.'

"And certainly, watch your frequency of emailing. Don't email a lot. It really" -- he let out a heavy breath -- "does not make people happy."

I wasn't self-aware enough to see that Ferriss was trying to save me from myself. Over a year later, when I was rummaging through old emails, I came across the 31 messages I'd sent Ferriss's assistant. Only then did I realize how much of an idiot I'd been.

"All right, man," Ferriss said as our conversation wrapped up. "I've got to go." He said goodbye and hung up.

A part of me wishes I could go back in time and shake my teenage self and explain what just happened.

If I'd learned my lesson then, things would have gone a lot differently when I found myself in Omaha with Warren Buffett.

Adapted from The Third Door: The Wild Quest to Uncover How the World's Most Successful People Launched Their Careers. Copyright © 2018 by Alex Banayan. Published by Currency, an imprint of Penguin Random House LLC.

More from Entrepreneur

We created the SYOB course to help you get started on your entrepreneurial journey. You can now sign up for just $99, plus receive a 7-day free trial. Just use promo code SYOB99 to claim your offer.
Jumpstart Your Business. Entrepreneur Insider is your all-access pass to the skills, experts, and network you need to get your business off the ground—or take it to the next level.
Discover a better way to hire freelancers. From business to marketing, sales, finance, design, technology, and more, we have the freelancers you need to tackle your most important work and projects, on-demand.

Latest on Entrepreneur