Just Ask.

I had a conversation today that caught me by surprise. I was discussing a number of opportunities that had come my way and I was confronted with this:

“How do you know so many cool people? It seems like you know everybody.”

That question took me aback. I guess I had never really paused to consider the fact that many of my friends don’t do the same things that are second nature to me. I shrugged off the question but I kept thinking about it throughout the day. What do I do differently to contact people? Is it better or worse? What are the different ways that I grapple with the stress of talking to someone new?

In the top 10 things that people fear, public speaking is number one. It ranks higher than death. Contacting someone through a cold call or email is a carbon-copy of the same fear but electronic. In the information age, it is too easy to find out anything and everything about a given person. We are inherently bashful and contacting someone out-of-the-blue is a surefire way to feel the cold sting of ignorance or rejection.

Although the internet reeks of anonymous interaction, it is amazingly connective. Marc Andreessen regularly responds to tweets from people he doesn’t know. Even Noam Chomsky will respond to emails if you send them to him. Part of the joy of the world is that it has grown smaller and you can talk to your heroes if you only reach out.

So here are a few ways I get out of my own head and send those damn emails, cold calls, and tweets without worrying too much:


If you think writing personal emails to dozens of people in a given day is easy, you’re damn wrong. The easiest way to send the same kind of emails quickly is to build a contact template. I normally format mine along the same lines:

  1. Introduction. This is to talk about who you are. If you’re a student, make sure that you introduce yourself as one. It’s extraordinary how willing people are to help out students. You are seen as someone to be mentored, especially if you’re asking for their help with something. I still refer to myself as a student from time-to-time because I am based around a university, trying to get into grad school eventually, and constantly learning. If you’re not a student, no big deal, just make sure that your profession relates in some way to what they’re doing or can potentially help them as well. The name of the game is motivated self-interest. There is definitely a bit of reciprocity to cold calling and emailing.
  2. Ask. This is what you’re emailing them for. Make sure that it relates to what they’re doing currently. Do some background research on the person and the company in order to tailor your ask in a specific way. Ask a few questions to start a conversation. This section is always different depending on the given person and industry.
  3. Offer to help. If you’re interested in what they’re doing, offer to do something for them. By reaching out, you are making yourself available to have a conversation with. You can definitely offer a unique perspective. You have inherent value just as someone else for them to talk to. If you have any current pertinent work to what they are doing, this is the place to put it. Do NOT attach documents to the first email you send. Many people receive phishing emails that way and have spam filters set up to catch emails like that.
  4. Wrap up. Let them know that you’d like to continue the conversation. Offer a number of times that you’re free and see when they are available. Put your contact information in the email.

Templates are extraordinarily helpful in sending emails quickly and efficiently to a bunch of people in order to get a nibble on an opportunity. Just be sure you proofread before sending so that you don’t make the mistake of sending the email to the wrong person.

It’s a habit. Get it?


I try emailing someone new every single day. That way I’m able to build my network. Wherever I go there is always somebody that is interesting that I can connect with. If you decide you want to be in the restaurant business, reach out to a different restaurateur every day. The same is true for any industry.

If someone responds to you, make sure you answer back ASAP. This person is giving you the time of day to hear your ideas and showing that you’re engaged and interested is hard to do online. The only true way to do this is a fast response time. This is doubly true when you are trying to coordinate a time to talk “in-person.” The sooner you respond, the sooner you can coordinate a time to connect deeper.

Phone Calls/Skype

Sometimes I’m lucky enough to transcend the email communication to have a verbal conversation. These are nerve-wracking. I normally block out a 3 hour block for a 1 hour conversation if it’s in the middle of the day because I’m terrible on the phone. The first hour is for preparation. I try to get to someplace quiet, someplace where I can write. I always write an outline of what the conversation will be about, a few questions, and an ask, something that both of us would be motivated to do after the conversation.

During the conversation, I have a cup of water nearby. It’s important to speak clearly, not take too long of pauses, and show you’re engaged by using verbal indications like: “uh huh” “yep” “definitely” etc. I’ve had conversations go terribly because they didn’t think I was engaged due to the fact that I wasn’t giving them verbal clues. Without body language, conversations are more difficult to convey your interest. Don’t worry if the conversation strays from a given topic, let it happen. If you’re forcing a conversation, it’s difficult for all of those involved. It’s important to really listen to what the other person is saying and to care about what they’re talking about. A conversation is a two-way street so asking personal questions is a good way to get started. I like asking: “I read (such-and-such) about you, but (thoughtful question)?” or introducing myself a little further. It is important to edit your personal story to include the details that they’re interested in. It’s okay, you’re interesting otherwise they wouldn’t be talking to you. Be excited. You’re talking to one of your heroes.

Skype sidebar: generally for the first conversation on Skype I don’t use video. This is generally because I can’t control the environment around me. Staging is incredibly important on Skype. The background in a given video, and what you’re wearing shows preparation. Think of Skype video conversations as interviews. They should always be in a location that is comfortable and engaging to you, without being distracting to the person you’re talking to.

After the conversation I leave the following hour to follow through quickly on whatever the conversational topic was about. I do this in order to impress upon the other person that I am incredibly serious about what we talked about. Normally this consists of a follow-up email based on the outline that I initially wrote before the interview (if we followed that outline).

They’re People

In the past year I’ve spoken to TED Fellows, Venture Capitalists, professors at the top of their field, CEOs of companies and more. One thing that they all have in common is that they’re human (I think). That means that they’re susceptible to the same kind of mistakes that we each make. That means that they were in the same position that you are at one point. They were all struggling to try to make it in the world. They were cold-calling and emailing people for opportunities all over the place. That means quantity > quality. You’re gonna suck at first. Be cool with it. They are. They were in the same boat. They have the same basic human quality of empathy as each and every one of us. That empathy will push them to respond. They want to help you because you’re an unknown. They may be able to change your life, and you may be able to reciprocate.

Want something? Just ask. The world is your burrito if you’d only take a bite. As long as you know what you want, you might as well reach out to that person that can help you. If they don’t respond, so what? Most of the emails I send go ignored. If they reject you, so what? The internet is still anonymous and you have never interacted with them in person. They don’t know you. If they say yes, then you’re set. You are one step closer to achieving your dream. All just because you asked.

Connect Deeper

Thanks for reading! If you liked that article and want to read more, be sure to click that tiny green heart and follow me on Medium at Elliot Roth to get updates on new articles as they come out. If you’d like to connect deeper, you can always reach me on Twitter.

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