What happened when the monarch of Kuwait, Fidel Castro, and the founder of IKEA sent me letters.

Tl;dr: I’ve sent thousands of cold calls/emails/letters over the years working in tech, publicity and startups, and have perfected a few ways you can get the attention of anyone. 


It was a normal day in high school, when FedEx came to the door with a package for me, from Bayan Palace in Kuwait. Yes, that Kuwait in the Middle East. I told my Mom, who had to sign for the package, not to worry, it was probably the Emir replying to my letter. I opened the package and sure enough, His Highness the Emir of Kuwait had sent me a signed photograph of himself, along with a letter from his secretary (with the official seal stamp!) thanking me, this kid right outside Los Angeles, for my letter and interest in his country. 

You see, I had a more unorthodox hobby growing up: I sent letters to hundreds of world leaders, CEOs, socialites, pontantes, anyone in the annals of fame. On a single sheet of paper, inside a five cent envelope bearing a 39 cent stamp, I asked three simple questions:

  1. Is it hard being (the CEO of a company, a founder, a leader, whatever they did), and…
  2. Do you have any advice on making it to the top, and…
  3. Can I have your autograph?

Believe it or not, I got a ton of replies, many of which I still have.

It started when I was 14 years old, and I had an idea. What if I reached out to George W. Bush, the then President of the United States. Would he respond? One stamp, one month, and one letter later, I find an envelope in my mailbox from 1600 Pennsylvania Avenue. My idea worked. While it was surely a form letter and fake autograph, my passion was ignited as quickly as I burned through my family’s stamp supply. 

I cracked open my family’s 2004 World Almanac, which had a directory of Fortune 500 companies, the CEO name, and their HQ address. I sent letters to those addresses with these simple questions and and got a ton of replies, including:

  • The billionaire founder of IKEA, sending me life advice airmailed from his Swiss Chateau
  • The CEO of Ferrari, fedexing me a letter, and a Ferrari hat saying that I will be a future customer (I have not fulfilled that statement – yet)
  • “Apprentice”-era Donald Trump sending me a signed photo (in a gold sharpie nonetheless)

After these successes, I decided to start reaching out to foreign leaders. That’s when it got….interesting. At first, I started reaching out to every country where I could find the address of their national capitol. I added three stamps this time to account for airmail costs, and deposited this next batch of letters in the mail.

Months later, the letters came back with exotic postmarks. London. (the Queen sent me a letter, well, her Lady in waiting) Paris. (President Hollande) Madrid. (The King of Spain!) Johannesburg. (Nelson Mandela). Havana. (Fidel Castro. Yes, I got a letter back from the Capitol of Cuba with a letter in Spanish, stating officially that the Leader of the Revolution was unable to personally respond to me).

Through these experiences, I learned a bunch of skills that I took with me as a startup founder, to being a first hire, to going into technology sales. All of these roles required the need to start new conversations with a stranger, an individual that you may have never met before. I learned a few key lessons, which you can use to get in touch with anyone you want:

  1. Do your research
    1. In writing to these leaders, I found their addresses through the Internet, almanacs, etc. There are multiple ways to do this digitally, such as through mailtester.org.
  2. Be brief in your ask
    1. Do not ask for the Moon. Write a brief email in the space of a smartphone screen. Don’t beat around the bush. Just say who you are and make the ask.
  3. Be persistent!
    1. As anyone in Sales knows, it takes time and many attempts to hear back from someone. If you want to make that key connection, that key sale, that call, be sure to do your followup and don’t overthink it!

Just as I picked up the metaphorical pen and paper to contact anyone, I am confident that any of you can do the same thing, with the right research, elbow grease, and yes, maybe some stamps.