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How to Actually Connect with Influencers

Pictured: Kimberly Rich with Legal Expert Sarah Kornblet from SarahKornblet.com

Pictured: Kimberly Rich with Legal Expert Sarah Kornblet from SarahKornblet.com

I really wanted to name this post “How to get Chris Guillebeau to ask for your number” But it felt too clickbait-ey...

It’s also somewhat misleading. Not that that didn’t happen (because it did) but that’s not the point. 

I’m here to share how I’ve been able to successfully connect with people who inspire me, over and over, and hopefully encourage you to buck up and go out and do the same. 

Disclaimer: this is not for the lazy. Or the the faint of heart. This is not for people who are mildly interested in chatting with someone successful in their industry, or who just want something out of it, and aren’t willing to give. This is also not a magic formula that works for every person, all the time. 

But here’s how it’s worked for me...

It felt sort of serendipitous. I had been delaying for months to write the email, and hit send. I knew I wanted to tell Chris Guillebeau how much his conference WDS had impacted my life, but an email just felt so impersonal. And so not me. 

Fortunately, Chris is a busy guy, constantly putting out books. And Austin is a great destination for a book tour! So as luck would have it, he scheduled a book signing here in town to promote his new book Born For This, and I made plans to show up. 

While I could have waited in line to gush all over him, while he half listens, and half writes some inspiring but likely generic message in my new book, that just wasn’t going to cut it. I had to leave an impression. I had to really communicate the change that had come from something he created and shared with the world. 

So I created something and shared it with him...

I painted him a watercolor painting. Yep! Sound the crazy bells! (Because I don’t care). 


I created something that hopefully illustrated how genuinely grateful I was, but also a little bit about who I was. 

It helped that I was the first in line to give him this gift. I’d made the mistake at the Lewis Howes book signing of NOT being first (or last) and I wasn’t going to do that again. Protip: Chat ‘em up while they’re still fresh and energized, or linger 'til you’re the last person if you’re looking for better odds at securing a post-signing hangout. 

The exchange actually went far better than I thought. It’s super scary and vulnerable to do something different! Or to make someone something! You never know how people are going to react.

But that’s the trick. You never know how people are going to react unless you do it. 

Chris was so surprised, and impressed, and truly grateful, that he asked for my contact info on the spot. He said, he can’t keep every gift people give him, but that he’d be keeping this one. He pushed the painting to the front of the signing table and said “Let’s make sure people can see it!” (Cue cry-face emoji).

And within hours of the book signing he had texted me to say thank you. 

That’s right, someone I look up to. Someone who’s work has radically changed the trajectory of my life, was texting me to thank me! He told me to keep in touch and to let him know if he can ever support me in any way. 

It took a few minutes for me to pick my jaw up off the floor.

I can appreciate that Chris is just a person. He and I have dozens of mutual friends and he’s an incredibly down to earth human being, but this was special. It was another reminder that by being not just genuine, but authentic, you can really leave a lasting impression. 

Pictured: Chris Guillebeau & Kimberly Rich

Pictured: Chris Guillebeau & Kimberly Rich


So how did this experience compare to the other times in my life that I’ve been able to connect with people who are where I want to be? Who have large followings? Who I legit just want to be friends with? 

There’s three central themes, and 3 things you can do to move towards similar connections and relationships: 

1) Be Genuine

Above all else, you have to truly want the best for this other person. It’s from this desire that you’ll be able to deliver the most value, and that you’ll actually be able to connect with them. If you’re pretending to be something that you’re not, or they can smell your ulterior motive from a mile away, it won’t work. 

When I was interested in quitting my corporate job to move abroad, I reached out to anyone and everyone who was living that lifestyle. I genuinely wanted to be their friends. That came through in my messaging, and by finding common ground we connected. 

Some of those people introduced me to other entrepreneurs who would go on to hire me, host me, and even become like family over the next few years. We often joke about the early days, “Remember when I was that rando on twitter who would send you messages?? And now look at us!” And then we clink glasses and laugh like we've known each other for decades.

2) Be Creative

You don’t have to paint someone a picture to show your creative side. There are countless ways you can be different and stand out. 

Youtuber, Sara Dietschy recently made an epic ode to famous Vlogger and videographer, Casey Neistat. Her video taught “How to Casey Neistat a Vlog” done in pure Casey Neistat vlogging fashion, and it was SO good, that it somehow made it into Casey’s inbox. 

He was so impressed with her work, that he dedicated his Vlog that day to giving her credit and in turn growing her followers from 4,000 to 40,000 OVER NIGHT. 

Talk about ROI. 

Another great example, Podcaster Cristina Canters was able to get Pat Flynn on her show by writing a rap, and tweeting him the video as an invite.

She did her research and understood that he not only likes beatboxing, but likely gets 300-400 emails per day, and therefore a tweet had a better chance of standing out and getting added attention.

If you’re serious about leaving an impression, do your due diligence and get to know the person you’re looking to connect with. Often, if you’re already an avid follower you know more than you think. 


3) Be Persistent

If early efforts fall flat, don’t give up. Now of course, don’t go into full fledge stalker-mode--and if you do DEFINITELY don’t refer to this blog as a source of your inspiration--but instead keep yourself based in reality. Chances are, the person you’re reaching out to gets hundreds of emails, tweets, snaps, etc. per day. So if they miss yours, or don’t respond, don’t give up on life and go straight for the ben and jerry’s.

Continue to add value, continue to reach out, but look for new and different ways to do so. Maybe the mode of communication you chose doesn’t work for them. Maybe you’d be better served to meet them at an in-person event? Maybe you’re better off getting close to them, by getting close to people who are already close to them. 

Since meeting Lewis Howes at his book signing here in Austin, I’ve consistently sent him Snapchats for the past 4-5 months. I do this, because I know that someday it will pay off. I chose Snapchat, because I know he’s an avid user and he actually invites people to message him, so I don’t feel out of line.

The trick is to send things that are relevant, that are valuable, and that give him a sense of who I am and what we might have in common. And you know what? 98% of the time he responds! In fact, this weekend he even upgraded from text to video!


One final piece of advice I have, is to be patient.

If you’re lucky enough to garner the attention of the person you admire, don’t bulldoze them with requests and ways that they can help you. How would you feel if every time you connected with someone they immediately shoved their book, or podcast, or resume in your face? You’d likely fake a phone call and high tale it out of there.

Same goes for busy, successful people. Respect their time, and respect that they don’t want to be used either. If a genuine connection forms, then they’ll be more than happy to help you out and support you in any way that they can. Work on making that genuine connection first.  

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