Greg Isenberg - 🧃You can meet anyone you want

Jonathan Courtney is back for another “Sippin' Time" episode, and this time, we’re talking about how to connect with anyone on the internet.

Jonathan used the exact strategy we discussed in this episode to make sippin’ time happen.

He slid into my DMs with a Loom video explaining his idea for a new SIP format.

We’d turn the tables, and he’d interview me about topics he thought would be valuable for you, the listeners.

I was intrigued. I figured, why not? And I gotta say, it crushed.

We had so much fun the first time, I invited him back for round 2. I think this one is even better.

If you’re wondering how to approach and build relationships with the people you look up to, this episode is for you.

​Watch on YouTube | Listen on Spotify | Tune in on Apple Podcasts​

If you’re short on time, here's a quick breakdown of my 4-step strategy for connecting with anyone online:

Step 1: Create content that resonates

Start by creating and sharing content that genuinely highlights your interests and expertise. Whether it's tweets, blog posts, or videos, make sure your content speaks to the values and interests of the people you want to connect with.

This shows you’re someone with insights to share. Someone worth knowing.

Step 2: Engage and shoot your shot

Be proactive. Set reminders to engage with content from those you admire. When they interact back with a like or comment, take it as your cue to reach out.

Don't overthink it. Go with something simple but thoughtful: compliment their work, share an insight, or ask a relevant question.

You’re starting a dialogue, not asking for anything.

Step 3: Make it easy for them to say yes

When reaching out, you want to make it as easy as possible for them to respond. Do your homework, find some common ground, and keep it genuine.

In the words of Jonathan Courtney, you gotta have that U2 "With or Without You" energy – frame your ask as a natural, no-pressure question.

Step 4: Meet them where they are

If they do respond, suggest connecting in a way that's convenient for them. Go to their city, attend events they're at, and go the extra mile to add real value to their life.

Remember, this isn't about you – it's about building a genuine, two-way relationship.

I've used this strategy to connect with everyone from startup founders to rock stars (seriously, just listen to the episode to hear how I ended up hanging out with Weezer and Green Day).

Follow these steps consistently, and I'm confident you'll be able to build relationships with the people you admire most.

​Check out the full episode on YouTube for more actionable insights, personal stories, and a few zingers.

Leave a comment telling us what you think. Do you like the format?

If you want to jump straight to the juicy bits:

​02:00 My Framework for Meeting Anyone
​07:17 How Jonathan Met NYT Bestselling Author, Jake Knapp
​08:13 Boring Marketing
​09:08 The Canvas Strategy
​12:01 How I Met Weezer Frontman, Rivers Cuomo
​15:16 The With or Without You Strategy
​19:35 Part 2 of the Weezer Story
​24:25 The Value-First Mindset
​29:29 Step 1 of the DM Strategy
​34:29 Step 2 of the DM Strategy
​36:56 Step 3 of the DM Strategy
​40:42 Remember to Follow Up
​
​About Jonathan Courtney
​Co-founder and CEO of AJ&Smart, a leading firm facilitation agency based in Berlin.
X: @Jicecream ​

I hope you find this conversation valuable. Forward them to a friend if you did or share on social to get others thinking.

I'll keep jamming if you keep watching. I read every reply if you care to reply :). You might get an answer back or get a shoutout on the pod.

​Youtube Spotify Apple Podcast​