How to Get What You Want... When Reaching Out to People Online

You reach out to someone you admire or someone you’d love to learn from. You send an email or message on social media. The message you send is somewhere along the lines of, “Would love to pick your brain”, “would love to connect” or “would love to grab coffee sometime”.

Although you’re excited about the possibility and took that first step - it lands on deaf ears.

You immediately think, “They think they’re too high and mighty to respond to a fan” or “They must be really busy and don’t have the time for me”. But, neither of those are true.

So how do you get what you want when reaching out to people online?

When reaching out to people at random, the receiver is instantly thinking, “Who are you?”, “Why would I give you my time?” and “What do you want?”.

Most of the time cold outreach gets interpreted as I want something from you and I’m making that as, “wanting to connect”.

It’s not them, it’s you.

The real reason you’re not getting any responses is that you’re doing it all wrong.

There is a way, a strategy, to not only get these high-level players to respond to you but to join in on their ‘inner circle’.

I’ve used this strategy to send a cold outreach message to industry leaders, whom I’m now good friends with, such as Joel Brown from Addicted2Success and Daniel DiPiazza from Rich20Something.

So how did I do it? How can you do it?


Let’s understand what’s not working before you can determine what is working.

Say you’re an accountant. You get paid $200 an hour to consult clients. Then someone comes up to you and asks, “Can I take you to coffee and pick your brain?” Which easily translates to “I don’t care about you, I just care about your knowledge on accounting and want to get as much information out of you to help myself, without paying your fee.”

How does the person you want to reach out to “win” in this scenario?

Not at all. In fact, he or she is losing.

He/she will waste at least an hour of time talking to you, which equates to a loss of $200 AND even if it wasn’t about the money, you have made it all about YOU getting access to their knowledge and information (that they’ve spent their career learning), instead of wanting to really get to know them. So there isn’t even any sort of emotional or non-tangible benefit here.

How do you “win” in this scenario?

You get access to a ton of knowledge and information that someone has spent a ton of time and money learning, and you get it all for free. Oh, wait. I mean for $4 because that’s how much a cup of coffee costs. $4 for an hour valued at $200 is an insult.

So you win. Account loses.

You may be thinking, “Maybe they should do it out of the kindness of their heart”.

Let’s walk through what that scenario looks like.

First of all, believe it or not, you’re not the first to reach out.

Depending on the caliber of the person you’re reaching out to, let’s say they get a modest 20 people reaching out a week. Out of the kindness of their heart, they say yes to all 20 and go for coffee the following week. That is 20 hours at a minimum, not even including commuting time, to be a kind person and allow others to “pick their brain”.

It then becomes a part-time job.

That’s 20 hours spent away from their business. That means their business grows at half the rate because they’re now only dedicating half the time to their job. If they maintained that, they’d essentially crumble their business, and no longer be in demand. Oh, and not to mention their time is valued at $200/hour x 20 hours (of coffee meetings) = $4,000/week of lost revenue.

We can logistically see that it’s near impossible for any sort of high-level player or even just person in demand to be so kind as to allow you “to pick their brain”.

It would be at a huge cost to them.

What makes you more special or stand out for the other 20 people PER WEEK that are reaching out? Usually, nothing.

Seems hopeless, right? Wrong.

There is a way to stand out and not only connect with these high-level players but to join their inner circle. Here’s how:


Familiarize yourself with them... really well.

Before starting a relationship with someone, you should know them really well. Especially if it’s a high-level player, you should know what they’re up to really well. This way, when you do eventually do connect it won’t be about surface level stuff that they likely repeat a million times. If you can find the answer on Google, you should never ask the person you’re looking to connect with that question. This will also show that you’ve been truly invested in them, following their journey and they’ll appreciate that (once you eventually connect).


Support them.

Determine how you can support this person, their mission, and their vision. This point is best demonstrated with an example. Suppose there are two different people reaching out to a high-level player. Which person do you think succeeds?

Person A.

Someone who has never invested in the high-level player’s programs, courses, products etc. So they’ve never really experienced what that high-level player is offering and it almost shows they don’t see the value in what that person is offering.

Person B.

Someone who has invested in the high-level player’s programs, courses, products etc. This shows that this person really believes and values what the high-level player is putting out there so much so that they’ve invested hard earned money in purchasing it.

OR perhaps they didn’t have the money but they spread the message of what that high-level player is offering. They constantly share the message on social media and tell family and friends about this what this high-level player is offering.

OR maybe this person is simply engaging with this high-level player. They open all their emails, they engage with all their social media posts and ultimately show they care.

So, before you ever even think of asking anything of a high-level player, you should be supporting their vision. Why on earth would they spend the time helping you if you can’t even support what they’re doing in even the smallest way? You need to earn the right.

I should also note here, although you may think that engaging constantly with their content is a lost cause - they will notice. I know this because the high-level players I’m connected with have told me they notice who their ‘super fans’ are - the people always engaging with their content.

Determine their needs and provide value (several times).

Next, you want to determine how you can provide value to whoever this person is that you want to connect with. Instead of you thinking that this high-level player should provide value for you as you “pick their brain”, first take some of your own time and provide them with value first.

It’s simple logic and math. If you provide value to someone first, they’ll be more likely to return the favor than if you provided no value.

Now, for the toughest question, “How do you provide value to someone who seemingly already has everything?”.

Let me give you some examples.

When I was connecting with Daniel DiPiazza, he was in the middle of a book launch and when someone is mid book launch let me tell you, they’re likely trying to make it a hit which means all their time and energy is consumed with making their book launch a success.

So, I reached out and said that I’d love to help him with the book launch by promoting it to an audience I’ve been building up. This allowed me to have a touch point with Daniel. A simple way to get my name in front of his face. He then put me in touch with his team to get the promo materials to support the book launch.

Then, I bought a bulk 20 copies. In the case of Daniel, if you bought bulk, instead of ordering on Amazon, you would contact their team to process the order. This allowed for another touch point with Daniel. I reached out and said that I wanted to purchase a bulk order of books.

Even if they were promoting how to buy bulk and there was a link I would have still reached out to him direct saying, “Hey, super pumped about the book launch, I’d love to buy some copies in bulk. What would the best way be to do that?” in which case he’d probably just send me to a link but again it was a touch point and this way I KNEW that he knew I just bought in bulk.

There is another way I could have taken this further… and this is something I did with Lewis Howes. I saw Lewis Howes’ book Mask of Masculinity was coming out and I was sharing it on my social media (tagging him of course) and had a few friends message me in response to my post that they just bought the book too. I screenshot the messages from my friends and, DM’d it to Lewis with a simple message somewhere along the lines of, “My friends saw my post about the book and got a copy as well! Awesome. Keep up the good work with the launch I know it’ll be a huge hit.” It’s subtle enough to make it known that my message was having an impact but bringing it back to him.

This leads to my next point of having as many relevant touch points as possible but before we dive into that let’s explore how you can determine a creative way to add value, especially if this person isn’t doing a book launch any time soon.

It’s really about getting creative.

Look at what that person is trying to achieve or what they’ve been up to lately. You should already be following this person closely, and know what their goals/focus are. And again, it’s about getting CREATIVE.

Maybe they recently started diving into a certain topic of interest. Is there a rare book you can send them on that topic?

Maybe they just moved into a new house. Is there some sort of housewarming gift you can send?

Still not sure? Simply send them a short email letting them know that you love what they’re doing and that you’ve found a ton of value in it. It’ll make them feel good if anything.

Get creative.

Have as many relevant touch points as possible.

As you noticed in my previous example, I had many touch points with Daniel but they were relevant. Not random ass messages that wasted his time. They were intentional and provided value.

The more you can get your name in front of their face the better.

You’re subconsciously priming that person with getting familiar with your name so that when you do eventually try to take the relationship to the next level, you’re not just some random person who came from out of the blue.

Again, get creative in how you can get in front of that person’s face as much as possible in a subtle way. Hint: The most basic, simple way, is constantly engaging and commenting on their social media posts or writing them and letting them know how valuable and helpful they have been.

Do Cool Shit

And finally, before we get to the finale of where you send the cold outreach message you need to keep something in mind. The best way to get cool, interesting people to want to connect with you is to do cool and interesting shit yourself.

Yes, my connection with Daniel DiPiazza worked but I was also able to show that I was featured in press, and was able to get 8 people to pay $5,000 to join my program. Now, I’ve stood out. That shows I’ve worked hard and those actions prove it to him. He knows I’m the real deal and not here to waste his time. I was walking the walk.

Then with Joel Brown from Addicted2Success, had I never run a retreat myself (or lived in Bali)  my reach out wouldn’t have been as strong. I was able to leverage that in my initial outreach.


What if you’re just starting out?

Ok, you may not have press coverage and all of that but think of the most interesting or impressive thing you’ve done that relates to them and leverage that.

Ultimately, if you want to attract high-level players into your life you need to be acting like a high-level player and taking the actions of a high-level player even if you’re not there yet.

This will distinguish you from the rest because instead of being all talk you are proving you’ve got what it takes and that you’re not just some leach looking for information, trying to get the most out of someone else as possible.

I have so many people with “ideas” that reach out to me but I don’t care about ideas, I care about people that are actually doing something. I know those people actually doing something aren’t going to waste my time.

So get some cool, interesting stuff under your belt that you can speak to, that relates to the person you’re reaching out to. Again, get creative.

Send the Cold Outreach Message

You’ve been following this person online, engaging with them, adding value to them, now it’s time to actually take it to the next level and get some 1:1 time with this person.


This loops back to where we started, sending a cold email or message. Simply by doing the steps above, you’re already putting yourself in a stronger position to get a response.

Funny how just now we’re at the end of the process - where most people try to begin.

You may be thinking, “Well that’s a lot of time and work just to maybe meet up with someone.” and you’re absolutely right. And that’s why the people who play the long-term game often end up on top.

I can almost guarantee you at least 95% of people won’t do the above before reaching out which means you’re already in the top 5%. You’ve already increased your odds of standing out.

The Structure of the Outreach Message

With the cold outreach message, you need to be strategic about how you position it.

  • You’ll want to give them some sort of genuine compliment. This is basic human psychology, people like to be complimented. Especially, entrepreneurs who never get a pat on the back for a job well done because they’re their own boss.

  • Next, establish a common ground. Do you both support the same sports team, do you have a common connection or interest? This bridges the gap between “them” and “you”.

  • Show you’ve done your research. Refer to specific elements of what their working on, their business etc. This shows that you’ve taken the time to draft a thoughtful message that isn’t just being sent to a million other people too.

  • Provide Value. Again, get creative and find a way that you can add value to them.

  • Make it about them. Not once should it be a sales pitch of what you do. Make it all about them and of being of service to them. Ultimately you should provide enough value that they ask YOU how they can work with you etc. This has happened for me and my coaching clients etc.

  • Have a specific call to action. Don’t just sent a message and leave it at that. Have a call to action. Ie. a 15 min call, a coffee etc. Be realistic with this request. Don’t say 2 min for a quick call because they know it’ll be more than that so it’s better you’re upfront. Also, create a call to action that is easy for them to respond without having to think too much.

    Ie. Do you have time for a quick chat this week vs do you have time for a quick 20 min video chat on Tuesday or Thursday at 7 pm? The first option means they have to browse their entire calendar and try to pick a time that they think is best or the second option that can quickly check Tuesday or Thursday and respond with a quick message.

    Even if you can position it as a quick ‘yes’ or ‘no’ even better.


In an upcoming blog, we’ll outline in more detail how to specifically structure a powerful outreach message that converts. Be sure to subscribe to our newsletter below so you can be notified when we release new valuable blog posts that can help you get started working remotely while traveling the world.

Building Relationships with Confidence

You now understand how to identify what’s not working. To recap, to build a relationship with a high-level player or future client you need to:

  • Familiarize yourself with them... really well.

  • Support them.

  • Determine their needs and provide value (several times).

  • Have as many relevant touch points as possible.

  • Do Cool Shit

  • Send the Cold Outreach Message

This strategy will put you in a place of confidence and empowerment.

It’s almost important to note that this won’t work on everyone. Some people it’ll resonate with and some it won't and that’s ok. The ones that do work though, it’ll be very powerful.

The whole premise of, ‘How to get what you want when reaching out to people online’ really comes down to coming from a place of service first and focusing on building the relationships. Remember, relationships take time. You need to constantly nurture them and be patient. You wouldn’t walk up to a man/woman and jump right to a proposal and the same goes with relationship building in business.

Networking is a critical component if you want to succeed at working remotely and it’s just one of the many topics we cover on WiFly Nomads. Download the full information package to learn more about how WiFly Nomads can help you start working remotely. We’ve already helped past alumni succeed and you could be next.

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