I Cold Emailed CEOs and Billionaires — Here’s How I Turned Them Into Investors and Mentors

A year ago, I was a new college grad who couldn’t find a job. Now I run Othello.ai, a VC-backed sales-tech startup with customers across the globe and the Fortune 500.

Here’s how I did it: I cold emailed some of the smartest people on the planet, got them to give me career advice, and turned those conversations into real relationships. They’re now my friends, mentors, and in many cases, very happy clients too.

I was not a well-connected person. Now I am. I swear, this is a lot easier than it sounds — and I’ll teach you how you can do it too.

It all started when I was in college, studying business. One afternoon, I was drudging through a particularly boring textbook and I thought to myself: Does the author of this textbook even have business experience? Why am I learning from them, and not a true business expert? And that led to my next thought: Well, how could I get legendary CEOs and thinkers to even notice me, let alone sit with me long enough to have a conversation?

I began with a list of people I admired. It included KKR founder Henry Kravis, Harvard professor Steven Pinker, Nobel Prize winner Paul Milgrom, and Home Depot CEO Ted Decker. I had zero connections to them. So I guessed their email addresses, wrote each of them a personal note, and hit send. The next morning, I had a reply from Henry Kravis in my inbox. I was shocked; he’s the most iconic private equity investor alive! Even more shocking: He offered to talk with me. Two weeks later we met over Zoom. He gave me some incredible advice, but here’s the most impactful thing he said to me: “I would give up everything to be in your shoes with your opportunities.” Why? Because I’m at the dawn of my adult life. This window of opportunity won’t last forever. I can’t waste it.

From then on, I made a list of the most interesting folks alive — across business, science, comedy, the military, the arts, and more. And it worked: I connected with a wide range of accomplished people, including the founder of Starbucks, Howard Schultz, and politicians like Nigel Farage. I can now call these people mentors and, in many cases, friends. Some, such as CEO of Lenovo, Bill Amelio, and CEO of Costco, Craig Jelinek, have since backed my company Othello.ai. Some are customers, and some I interact with weekly.

Here’s the process I followed.

Step 1: Research.

Before reaching out, I needed to make sure I could craft an email that made an impact. My goal was for them to know that my intentions were pure, and that they could actually make a clear impact on me in 30 minutes.

I researched everything I could about each of them — from their tweets and interviews to their books and published work — trying to understand what shaped them and what they cared about. Then I wrote an email from the heart, what I expected to learn, and I directly tied it to their interests and work.

My cold emails follow a simple structure. I start by explaining why I looked them up and detailed how their work has impacted me. Next, I briefly shared who I am and why I am worth their time, proving that I’m curious, ambitious, and won’t waste their efforts. Then, with extreme gratitude, I asked for 30 minutes for a conversation. This email must all be under 150 words; busy people don’t have time for anything longer.

Here’s an example. It’s the actual email I sent to Steven Pinker:

Steven —

I’m Jared Zelman, a senior at USC. I built a SaaS company to 30 employees in high school, sold it in college, and spent last summer flipping burgers at my local diner in NY.

I recently watched your discussion with Joe Rogan and it really stuck with me. Specifically, the way you explained progress from who you are to who you want to be changed how I see the world as a senior in college. I’ve been diving into your work since and learning a ton.

I’d love your advice on a few personal and career questions about building something meaningful in an environment (college) that often rewards task-completion over creativity. I know it’s a long shot, but if you have a few minutes to chat, I’d be really grateful and will make the most of it.

Jared

Step 2: Follow up

I had to often send persistent follow-ups, each tightly tailored but emphasizing the same key points as the original email.

A polite follow-up goes a long way in the lives of busy people. To avoid being annoying, limit this to three follow-ups and be hyper-thankful for their time. Truthfully, you might still come off as annoying, but this is the sweet spot. Space these emails out over three weeks.

Here’s an example. It’s the follow-up I sent to Pinker:

Steven — while I might be a new fan, I’ve spent probably 15 hours this week (time which should have perhaps been spent studying for midterms) reading Better Angels and Blank Slate. It’s made me think differently about how I assess my early career after graduation this year.

I’m in a big transition between college and adulthood and it would mean the world to learn how you made the most of this when you were my age. If you have a few minutes to chat, I’d really appreciate it.

Looking forward to hearing from you,
Jared

Step 3: Come with great questions.

When I first met my role models, I thought they’d have all the answers — but no one does. These people might talk with you, but it’s up to you to draw the best information out of them.

You must prepare specific questions, and have a clear agenda for the call — otherwise their time (and your time) will be wasted. Learning is as much about asking the right questions as it is getting the right answers, so do not show up without questions and a goal.

Step 4: Never be greedy.

When connecting with high-profile people, you must have a genuine and authentic interest in learning. You cannot be “learning”… but secretly looking for a job, for an investment, for a customer. The world’s greatest minds are clever enough to sniff that out.

There’s that old saying, “Don’t meet your heroes.” I’ve found that to be (mostly) wrong. Through my cold emailing, I’ve learned more from direct conversations than in all my years of college combined.

Now that I’ve met so many of my role models, and I’ve started to build my own company, you might think my cold emailing days are behind me, but I still reach out directly to folks I want to meet. No one is above a cold email, and no one is too busy to be curious.

A year ago, I was a new college grad who couldn’t find a job. Now I run Othello.ai, a VC-backed sales-tech startup with customers across the globe and the Fortune 500.

Here’s how I did it: I cold emailed some of the smartest people on the planet, got them to give me career advice, and turned those conversations into real relationships. They’re now my friends, mentors, and in many cases, very happy clients too.

I was not a well-connected person. Now I am. I swear, this is a lot easier than it sounds — and I’ll teach you how you can do it too.