What do you do when the room you need doesn’t exist?

You build it.

In this episode of The Awkward Handshake, Mary and Megan sit down with author, storyteller, and ghostwriter Jessie Kwak to talk about what it looks like to create the kind of community you wish you could find.

Jessie shares how she built a thriving writers’ community in Portland — one that started small, grew through trust and referrals, and now includes both a real-life backyard gathering and an active online Slack space. Along the way, she offers a thoughtful look at what makes communities work, why curated spaces matter, and how good people really do know other good people.

This conversation goes far beyond “start a Facebook group and hope for the best.”

It’s about intention.
It’s about trust.
And it’s about realizing that if the space you need isn’t out there yet… you may be the one meant to build it.

In this episode, we talk about:

• Why curated communities often feel safer and more useful
• How Jessie’s writers’ group evolved from an in-person meetup into a larger Slack community
• What it takes to maintain trust in both physical and online spaces
• Why strong communities grow best through referrals and real relationships
• The difference between shallow promotion and meaningful collaboration
• How collaboration often takes longer than people expect
• Why networking can lead to friendships first and opportunities later
• The hidden labor of being the “mother hen” of a community
• What happens when you can’t find the room you need

Our Guest

Jessie Kwak is an author, storyteller, and business book ghostwriter based in Portland, Oregon. She writes thriller novels, science fiction, and nonfiction, and helps other writers bring their books to life through coaching and ghostwriting. She also hosts a vibrant writing community in Portland that has grown into a larger Pacific Northwest writers network.

https://www.jessiekwak.com/

Why this episode matters

If you’ve been waiting for the perfect room, the perfect group, or the perfect invitation… this episode is your reminder that sometimes the strongest move is to stop waiting.

Build the thing.
Invite the good people.
Let it grow from there.

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Small talk gets a bad reputation.

People love to say they hate it. They call it shallow, pointless, or awkward. But in reality, small talk is one of the most powerful social tools we have — especially in networking spaces.

In this episode of The Awkward Handshake, Mary and Megan unpack why small talk matters more than people think and how it acts as the social bridge that helps strangers move toward meaningful conversation.

Because before you get to the big ideas, the collaborations, and the business opportunities… you have to build comfort first.

And that’s where small talk shines.

Mary and Megan explore how small talk creates safety in a room, why it helps people regulate socially, and how it gives conversations somewhere to go. They also share why resisting small talk can actually make networking harder — not easier.

If you’ve ever felt awkward starting conversations at events or wondered how some people make networking look effortless, this episode will change how you think about the humble art of small talk.

In This Episode, We Talk About

• Why small talk is often misunderstood
• How small talk helps people feel safe in unfamiliar rooms
• The role small talk plays in building trust
• Why skipping small talk can make conversations feel abrupt
• How small talk opens the door to deeper connections
• The difference between transactional networking and relational networking
• Simple ways to get better at starting conversations

Keep in touch!

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Most networking advice tells you to perfect your elevator pitch.

But what if that’s the wrong place to start?

In this episode of The Awkward Handshake, Mary and Megan sit down with Kellen Moody to talk about why people are so much more than the one-line explanation of their business — and why the best networking conversations rarely start with a rehearsed pitch.

Kel brings a refreshing perspective on curiosity, connection, and the power of being a genuinely interesting human in professional spaces. Together, the three of them unpack how real relationships form, why curiosity is one of the most underrated networking skills, and how conversations become more meaningful when we let people show up as full humans instead of job titles.

If you’ve ever felt boxed in by the pressure to “deliver the perfect pitch,” this conversation might be the permission slip you didn’t know you needed.

Because the best rooms don’t reward the most polished pitch.

They reward the most human presence.

In This Episode, We Talk About:

• Why elevator pitches can sometimes shut down real conversation
• The role curiosity plays in building authentic connections
• How to ask better questions in networking settings
• Why being interesting matters more than sounding impressive
• The difference between transactional networking and relational networking
• How curiosity leads to stronger collaborations and referrals
• Why your personality and interests belong in the room too

Connect with our guest, Kellen Moody:

• Kel's Website
• Kel's LinkedIn

Keep in touch!

Follow Megan Eckman

• Fat Cap Design
• PDX Spellbound

Follow Mary Williams

• Sasquatch Media Grounds
• Sensible Woo