by Niall Doherty

It’s pretty much a no-brainer among successful people that to become successful, you must surround yourself with the right kind of people. As Jim Rohn once said, “you are the average of the five people you spend the most time with.”

That means that you’re about as fit, as rich, and as happy as the five people closest to you.

I want to be a successful entrepreneur, someone who can be dropped pretty much anywhere on Earth with little money in his pocket but has the skills, knowledge and confidence to build a solid business that improves the lives of many.

To become a successful entrepreneur, I have to surround myself with successful entrepreneurs. As such, in recent weeks I’ve been reaching out to several people who fit that description, arranging meetups, and sitting down with them to soak up their wisdom. I’ve also been doing similar with fitness professionals to help reach my fitness goals.

This “reach out and meet up” approach has been going so well that I’m kicking myself for not having started earlier. And just in case you’re not already doing this kind of thing yourself, I hoping this post is the nudge you need to get started.

The Reach-Out Challenge

Here’s what I want you to commit to:

By Friday next week, I will have…

a) identified at least three people who I believe can help me towards a goal,
b) reached out to each of them, whatever way I can,
c) asked if they’d like to meet sometime for a chat,
d) followed up within 2-3 days if I haven’t heard back from them.

Who to reach out to

You’re looking for people who have already accomplished what you want to accomplish or are at least well on their way and a few steps ahead of you. For example, if you want to become a happily married person, find someone who has been happily married for years, someone whose relationship you’d like to emulate. Ideally they should have similar values and ethics to you, someone you can easily respect. You also want them to be open and articulate, happy to answer questions and explain how they view the world.

You don’t have to know them personally. A weak tie1 is more than enough, or you can just make-do with a cold approach. The worst they can say is no to your request, or just ignore it. No big deal.

Your goal is to actually meet with these people in person, to sit down with them and pick their brains. As such, you want to make sure you’re reaching out to people in your locality, or at least somewhere you’re willing to travel to.

How to reach out

Regardless of how you’re contacting them (phone/email/in person), there are a few key things that you should try to do:

  1. Keep your message short and to the point.
  2. Flatter them (but not too much).
  3. Mention a mutual friend or acquaintance if you have one (even better if you can get that person to make the introduction).
  4. Offer to buy them lunch or coffee.
  5. Don’t be needy.

If you’re sending an email, for example, try something like this…

Subject: You’re an expert on business [or relationships/fitness/travel/whatever]

Hi John,

My name is Niall Doherty I’m very eager to learn about business and entrepreneurship. I understand it’s important to learn from people who are already successful, and our mutual friend Ali Baba tells me that you are certainly such a person. I was wondering if you’d be free some time next week to chat over lunch or coffee (my treat)? I’d love to pick your brain for a half hour or so, as I’m sure I’d learn a ton.

I understand you’re busy so no worries if you can’t meet up. I promise not to take it personally 🙂

Thanks for your kind attention.

– Niall

If you don’t have that mutual friend to mention, say you were impressed by something you read on their blog or an article about them in the newspaper. No need to make something up. Just be honest about why you’re reaching out to them specifically.


Two great articles on email pitching from Derek Halpern (thanks to Bob in the comments for the head up):

And another great article emailed to me by Bruce:

Follow up

If you don’t hear back from them within 2-3 working days, be sure to follow up. It’s very easy for someone to ignore one email or voice message, but they start feeling rude if they ignore two, especially if you repeat the request politely.

My favorite approach is to send an email first and then follow up with a phone call. Keep calling until you get through to them. If they have a gatekeeper, ask what time you can call back to speak to your target. Once I get through, I say something like…

Hi John, this is Niall Doherty. I sent you an email last week. I’m the guy interested in learning about business.

After that I’ll shut up and wait for them to speak. Whether they remember me or not, I go on to tell them that I was just following up to make sure they received my initial message. At that point they typically promise to find it and get back to me later in the day, or ask me to resend the email. Which is perfect. I’ll then thank them and hang up. You don’t want to make them feel cornered, so avoid coming across pushy or needy.

Alternatively, you can just follow up with a simple email like this:

Hi John,

Just following up quickly to see if you’ve had a chance to read my previous message. Let me know if you’d be free to meet up sometime.

Thanks again.

– Niall

If they don’t get back to you after the follow-up, just move on to someone else. You want someone who’s happy to meet up and chat with you, not someone who needs their arm twisted and considers it a chore.

That said, sometimes a person will need a little convincing to meet up with you. They might respond with something like, “What is it exactly that you want to talk about?” What I try do in that situation is impress upon them that I’m not looking for a magic bullet, but rather that I’m interested in learning about what it takes to get to where they are, how they look at the world, what their journey has been like, etc. I’m basically letting them know that I’m in this game for the long run and willing to work hard, not looking for some quick fix or hoping to piggyback off their success.


If you’re like me then it’s easy to talk yourself out of writing that email or picking up the phone. It’s not urgent and nobody will know if you chicken out.

So here’s where I’ll ask you to set a penalty for yourself should you fail to reach out to three people by Friday next week. The penalty needs to be severe, something that you really don’t want to have to do. I’m pretty strict with my diet six days a week and then allow myself to eat whatever I want on my “cheat day.” I absolutely love cheat day, and I’ve found that a motivating penalty for me is to promise to give up two weeks of cheat day should I fail to reach a goal.

You’ll know best what penalty will work for you. A friend of mine once agreed to shave just the back half of his head if he didn’t reach a goal. He was terrified of the embarrassment that look would cause him, so he made damn sure he put in the work and reached his goal.

You might also consider a monetary penalty. Give a painful amount of money to a friend and instruct them to either keep it or donate it to a charity you hate should you fail to reach your goal.

If you’re serious about this challenge, go ahead and post the penalty you decide on in the comments below.

Tips for the meeting

Assuming you actually do reach out to three people by next Friday, there’s a good chance that one or more of them will respond positively and agree to meet up with you. So a few quick tips about the meeting:

  1. Do your research in advance so you already know quite a bit about them and their business.
  2. Have smart questions ready to ask them (more on this below).
  3. Once you ask a question, shut up and let them speak. They should be speaking at least 80% of the time.
  4. That said, don’t be afraid to share some quick stories of your own. You don’t want it to feel like an interview, more like a casual chat, so be willing to share your own successes and struggles.
  5. Listen carefully to what they say. Ask for clarification when needed. Summarize and paraphrase the points they make (“Let me make sure I understand what you’re saying…”)
  6. You pick up the check. Don’t ask or offer. Just take care of it quietly.
  7. Offer to help them (see below).

How to ask smart questions

Check out these two videos by Derek Halpern and Ramit Sethi:

It’s good to ask specific questions, but general, open-ended questions can also be valuable. Here are some I like to ask:

  • How did you get started in business? Was it something that came naturally to you?
  • If you could go back in time and give 20/30 year-old you one piece of business advice, what would it be? (Alternatively: What do you wish you’d learned earlier?)
  • What do you think is the most misunderstood part of what you do?

What’s in it for them?

I’ve had to overcome the limiting belief that I wasn’t worthy of successful people’s time. You might have to do the same. So here are two ways you can do that.

The first is to realize that you often help the other person just by having them share their knowledge with you. I’ve had this experience myself when a reader will email me asking for advice on some topic, and it’s only upon hearing the question that I realize I have something of value to share. As they say, the best way to learn is to teach, and when you reach out to someone, get them to sit down with you and answer your questions, you’re helping them reflect on and reinforce lessons they’ve learned in the past.

Second, you’d be surprised just how much you have to offer a successful person. In The Education of Millionaires, author Michael Ellsberg advocates asking successful people these two questions:

  1. What’s most exciting for you right now in your life/business?
  2. What’s challenging for you in your life/business right now?

What you’re essentially doing by asking these questions is inviting people to tell you how you might be of service to them. And you can be of service either via your existing connections, or via your ability to give advice.

For example, you might learn that the business savvy person has a teenage son who loves adventure sports, in which case you recommend he check out the excellent Parkour classes you’ve been taking. Or perhaps the guy himself is overweight and expresses an interest in cleaning up his diet, opening the door for you to talk about your experience eating Paleo.

Those are just two examples of my own, but you get the picture. As Ellsberg writes…

the three areas of life the majority of people spend most of their time worrying about are money, relationships, and health. In my experience, very few people have all three of these areas buttoned up in their life, at least not as much as they like. If they’re more successful than you, it’s probably the case that they are more successful in only one area (business, marketing, sales, fame, etc.).

Point being: You have a lot more to offer people than you think you do. Just ask the right questions and you’ll eventually come across something you can help them with.

Alright, I’ve said enough

Are you up for this challenge? I hope so. Surrounding myself with successful people and getting to pick their brains regularly has already helped me so much, and I’m sure you’ll get a lot out of doing similar.

So here’s what I want you to do in the comments. Tell me…

  1. what kind of people you’re going to try connect with before Friday of next week.
  2. what penalty you’ll have to perform should you fail to reach out to and follow up with at least three of them.

Let’s get to it!

Show 1 footnote

  1. A “weak tie” is when you and the other person have a mutual friend or acquaintance. You can use that commonality to break the ice and establish trust by association.

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