Hey Reader, I’m writing to you while on my flight back from New York and the OOO Summit. Sorry for the delay, but I was out late exploring the streets of Brooklyn and sampling pizza slices wherever the locals told me to go.

It was a great event to see a lot of creators and interesting people. Nathan Barry, Justin Welsh, Nicole Walters-Csillag, and Sahil Bloom were among the speakers. I hadn’t been to New York in years, and it was a lot of fun to find great food, drinks, and meet new people working on interesting things. I even got recognized for my YouTube channel!

Quick funny story about that. My name tag said YouTuber and the guy next to me in the coffee line said “Oh are you low-key famous?” and I said “My channel is a good size, but no, people don’t come up to me”… and literally 5 minutes later someone came up and said she loved my channel. The guy got a kick out of that 😆

For this week’s WRAP I’m going to share a few lessons from the event, people I talked to, and how to get the most out of these kind of things to raise your profile and build your network, even if you’re not super outgoing.

The WRAP is sponsored by:

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Get the heck out there

There’s something special about being in person. Don’t get me wrong, it’s cool to have online communities. I have one! But it’s even better to be with people in a space.

As I walked through Central Park, wrote my notes and doodled my sketches in a coffee shop, I realized the analog aspect of my channel is about more than pen and paper. Everything I love is rooted in being in a place.

I love to be at a meetup instead of on a call.

I love to write and draw instead of type.

I love to be outside instead of inside.

What dawned on me during the event is all these things take time and intention to make work. In many cases they take more effort. But to me that’s kinda the point. The effort makes the meaning.

That’s not to say online is less important, I don’t think I’d be doing what I do for “work” if it wasn’t for the internet. But to mindlessly default to digital convenience when physical presence has such outsized meaning—that’s the thing I have to keep in mind.

Look at it a different way, with food. I saw a report this morning that 75% of restaurant business comes from takeout and delivery. People aren’t just cooking less, they’re going out less! Look at my Brooklyn-Williamsburg self-guided tour last night.

I could have DoorDashed everything to my hotel and watched the Knicks pummel the Celtics. Instead I went out, had a drink, struck up a conversation, asked for pizza recommendations, went there, and repeated 2 more times.

I had incredible pizza and beers, told jokes, high-fived hipsters, told tattoo stories, argued about Jalen Brunson as a top 5 player, and found a little Thai restaurant with 6 tables where you have to ring the doorbell to be let in because you’ll bump into someone if you just barge in.

And here’s the unfair advantage you can use. People are so desperate for connection—especially in person—that if you make an earnest effort to connect with them they will readily accept.

Analog living takes effort, but (to me), it’s worth the effort every time.

Find Your Angle

I’ve written about Scott Adams’s concept of the Talent Stack before. Short version is that Adams doesn’t think he’s the funniest guy, the best cartoonist, or the smartest business person. But he is the best combination of those three elements, stacked together and expressed in the comic strip Dilbert.

One thing I’ve done for years is take my notes in a “sketchnote” style. It’s unique, looks great, and is an instant conversation starter. People sitting next to me can’t help but comment. When I post the notes on social media and tag the speaker, they will comment and share with their audience. If I get to talk with the speaker (in person), he or she will want to talk with me more.

Like Adams, I don’t consider myself a “big A” Artist. I just make little doodles to help me visually anchor an idea. Most times this is with stick figures, big words, and simple graphics. But it’s different. It implies that I think a little differently, am willing to do a little more than normal, and that I take time to make things look good. Those traits have always been a big differentiator and will always be that way.

3 Ways to Be More Outgoing

I was recently talking to my friend Sonja, who is a big deal happiness expert and professor at the University of California, Riverside. She has a great newsletter called The Happiness Files (sign up here) and she was telling me about a study that showed the benefits of pretending to be more outgoing.

Turns out that short bursts of pretending to be more outgoing and extroverted really does boost your happiness and enjoyment of the moment. This is particularly true when in social situations like a conference or meetup, or even hanging out with friends.

She’s writing about this study in the next issue of her newsletter—which you should sign up for here—but let me give you a little sneak peek on three things to try:

1. Experiment with Extraverted Behaviors: Pick just one or two actions—for example, start a conversation with a stranger or speak up more openly.
2. Focus on Behaviors, Not Labels: Think in terms of action: “I’ll say hi to the person in line” or “I’m going to share my opinion in this meeting,” not “I need to be an extravert.”
3. Curate the Environment: Try these behaviors in safe places—coffee shops, small gatherings, or with upbeat music playing. Make it something you look forward to, not a chore.

Just remember to pay attention to your energy and find your balance. If you need a boost, then act more extroverted, but when you find yourself running low on that same energy, dial it back and take some time to recharge.

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Bring It Together

1. Show Up In Person
Being physically present creates unique opportunities for connection. Instead of defaulting to digital convenience, make the effort to attend events and meet people face-to-face.

2. Develop a Unique Angle
Find your differentiator - like taking sketchnotes during talks. This can become an instant conversation starter and help you stand out. When shared on social media, it can attract attention from speakers and their audiences.

3. Practice Strategic Extroversion
You don’t have to be naturally outgoing. Instead:

• Choose specific actions like starting conversations with strangers
• Focus on behaviors rather than trying to change your personality
• Start in comfortable environments like coffee shops or small gatherings

Remember: people are eager for genuine connection. If you make a sincere effort to engage, they’ll likely respond positively. Just be mindful of your energy levels and take time to recharge when needed.

Thanks for reading, and if anything in this email resonated with you—send me a quick email back and share! I ready every reply 👀

Matt

Fun note: I wrote this newsletter listening to the Teenage Mutant Ninja Turtles: Mutant Mayhem soundtrack by Trent Reznor and Atticus Ross. My favorite tracks are Grand Theft Ice Cream Truck and Enter the 37th Chamber.

p.s. if you have a (literal) minute to share feedback, click here.