After 20 episodes, dozens of conversations, and more networking events than we can count… what actually works?

In this Season 1 finale of The Awkward Handshake, it’s just Mary and Megan—taking a step back to reflect on everything we’ve learned about networking, community, and how people really connect.

This isn’t a highlight reel. It’s a reality check.

We talk about what surprised us, what held up across different environments, and what consistently didn’t work—no matter the city, the event, or the industry.

If you’ve been listening all season, this is where it all comes together.
And if you’re new here… this is the fastest way to understand what actually matters.

In this episode, we talk about:

• What patterns showed up across all 20 episodes
• The difference between good rooms and bad ones
• Why networking isn’t about volume—it’s about intentionality
• What actually leads to real relationships and opportunities
• The role of consistency, curiosity, and follow-through
• What we got right—and what we’ve changed our minds about
• Why most networking advice falls flat in real life

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What if one of the best “networking spaces” in your city… is a romance bookstore?

In this episode of The Awkward Handshake, we sit down with Katherine D. Morgan, the owner of Grand Gesture Books, a romance-focused indie bookstore in Portland, Oregon that has quietly built one of the most engaged communities in the city.

This conversation isn’t about traditional networking. It’s about what happens when people gather around shared interests, feel safe being themselves, and keep coming back—not because they have to, but because they want to.

Katherine shares how she built Grand Gesture Books into more than just a retail space, how her events bring people together in a way that feels natural and fun, and why romance readers might be some of the best community builders out there.

If you’ve ever thought, “There has to be a better way to meet people…”
This episode might expand your definition of where connection actually happens.

• How Grand Gesture Books became a community hub, not just a bookstore
• Why romance readers show up differently (and why it works)
• The power of interest-based communities
• What makes events feel welcoming, fun, and low-pressure
• How Katherine curates experiences that keep people coming back
• Why not all “networking” has to feel like networking
• The role of storytelling and shared identity in building connection

Meet the Guest

Katherine D. Morgan

Writer and owner of Grand Gesture Books, a romance bookstore in Portland, Oregon.

Katherine is the author of the chapbook No Self-Respecting Woman, with work featured in outlets including Huffington Post, Bitch Media, LitHub, The Rumpus, and HelloGiggles. Her work has been nominated for Best of the Net, and she’s built a thriving in-person community through her bookstore and events.

Connect with Katherine:

• Website: https://katherinedmorgan.com
• Instagram: https://www.instagram.com/blcktinabelcher/?hl=en

About Grand Gesture Books

Grand Gesture Books is a romance-focused indie bookstore in Portland, Oregon that hosts events, readings, and gatherings for readers who want connection as much as they want a good book.

Learn more + check out upcoming events ➡️ https://www.instagram.com/grandgesturebooks/

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What does it take to build a creative community that people actually want to keep coming back to?

In this episode of The Awkward Handshake, we sit down with Kaitlin Carpenter, the organizer behind Creative Mornings Portland, to talk about what it really looks like to sustain a creative community over time.

Kaitlin isn’t just hosting events—she’s curating an experience. From speakers to structure to the feeling in the room, Creative Mornings has become one of Portland’s most consistent and well-loved creative gatherings.

We talk about how she brought the chapter back to life, what it takes to keep momentum going, and why the best communities aren’t built on hype—they’re built on care.

If you’ve ever wondered how some events feel effortless while others fall flat… this episode pulls back the curtain.

In this episode, we talk about:

• How Kaitlin relaunched Creative Mornings Portland
• What makes a creative community feel consistent and trustworthy
• The role of curation in building strong events
• How to choose speakers that resonate with a wide audience
• Why structure matters more than people think
• The balance between creativity and sustainability
• What keeps people coming back month after month

Meet the Guest

Kaitlin Carpenter

Writer and creative strategist, founder of BattleCat Strategy, and organizer of Creative Mornings Portland.

Kaitlin has worked with organizations like NASA Earth Science, the U.S. Department of Justice, and Trust for the National Mall to help them connect with the right people through storytelling and strategic communication. In 2019, she relaunched the Portland chapter of Creative Mornings and has been bringing creative speakers (and donuts) to the stage ever since.

Connect with Kaitlin:

• Website
• Instagram
• LinkedIn

🎨 Want to attend a future Creative Mornings chapter? Find Portland's events and other events worldwide here: https://creativemornings.com/

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What if the thing blocking your business… isn’t actually your business?

In this episode of The Awkward Handshake, we sit down with Micah Freeman, a licensed therapist, to talk about the overlap between mental health, nervous system regulation, and the way we show up in networking and business.

This conversation goes deeper than tactics. We explore the moments where strategy isn’t the issue—and where avoidance, fear, or dysregulation might be quietly running the show.

Micah breaks down how to tell the difference between a real business problem and an internal one, why so many people stay stuck trying to “fix” the wrong thing, and how understanding your own patterns can completely change how you connect, communicate, and grow.

If you’ve ever thought, “I know what to do… so why am I not doing it?”
This episode might answer that.

In this episode, we talk about:

• The difference between a business problem vs. a therapy problem
• How avoidance shows up in networking and visibility
• Why your nervous system impacts how you connect with people
• The role of emotional regulation in business growth
• Why “fixing your strategy” doesn’t always fix the issue
• How to recognize when you’re stuck in a loop
• What it looks like to build awareness instead of just pushing harder

Meet the Guest

Micah Freeman

Micah Freeman is a licensed professional counselor, educator, and coach who helps people stop overthinking their way through relationships and start understanding the patterns actually driving their behavior. With 10 years of clinical experience and 18 years of teaching, he also serves as adjunct faculty in the counseling department at Portland State University.

He is the founder of Ego Strength Coaching and host of The Self-Study Lab podcast, where he teaches a nervous-system-informed approach to understanding behavior, including how often we confuse stress responses for personality traits.

➡️ Get your free PDF from Micah here!

Connect with Micah:
🔗 Website
🤝 LinkedIn
🎧 Micah's Podcast

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What happens when you take your networking skills out of your home city… and drop them into a massive conference?

In this episode of The Awkward Handshake, it’s just Mary and Megan (recording after returning from BookCon NYC) sharing their immediate reactions to what networking feels like in a high-energy, location-based event.

This is a real-time download of what’s different, what’s surprisingly the same, and what actually matters when you’re meeting people outside your usual ecosystem.

We talk about the energy of large conferences, how people show up differently, and why the same core networking skills still apply—even when everything else changes.

If you’ve ever wondered whether networking at a big event “counts”… or how to make the most of it when you’re there, this episode is your field report.

In this episode, we talk about:

• What networking feels like at a conference vs. local events
• The energy shift of being in a new city with new people
• Why the same core skills still apply (even in chaotic environments)
• How people show up differently at large-scale events
• What makes conference networking feel easier—or harder
• The role of proximity, timing, and spontaneity in connection
• Why sometimes you just have to go to the thing and see what happens

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What does it actually take to build a community where people feel safe enough to show up as themselves?

In this episode of The Awkward Handshake, we sit down with Polly Bilchuk and Oliver Dinero, the founders of Unlock Collective, to talk about how they’ve built one of Portland’s most trusted queer networking spaces.

This isn’t just about hosting events. It’s about designing a room with intention—who it’s for, how it feels, and what people are allowed to bring with them when they walk through the door.

We talk about how Unlock Collective came to life, why their quarterly format works, and what it really takes to create a space where connection isn’t forced… but it does happen.

If you’ve ever walked into a networking event and thought, “this isn’t for me…”
This episode shows what it looks like when it finally is.

In this episode, we talk about:

• How Unlock Collective got started and why it fills a real gap in Portland
• What makes a queer-centered networking space feel different
• Why intentional design matters more than just “getting people in a room”
• The power of hosting quarterly events instead of constant meetups
• How to create a space that feels safe, welcoming, and real
• Why community-building requires boundaries—not just openness
• What it means to build trust over time (and why that’s the real goal)

Meet the Guests

Polly Bilchuk + Oliver Dinero

Co-founders of Unlock Collective, bringing vision, structure, and thoughtful design to community experiences.

About Unlock Collective

Unlock Collective is a Portland-based queer networking community focused on creating intentional, welcoming spaces for connection.

Their events are designed to feel different (less transactional, more human) with a focus on trust, safety, and real conversation.

• Website
• Instagram

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What if networking isn’t something you turn on when you need a job…
but something you build for the rest of your life?

In this episode of The Awkward Handshake, we sit down with Dinesh Mathew, a business operations executive turned consultant, to talk about what actually makes someone a great networker and why it matters more now than ever.

This conversation goes beyond surface-level advice. We get into the realities of today’s job market, how networking has changed, and why the people who succeed aren’t always the loudest in the room… they’re the ones paying attention.

Dinesh shares how his background in market research shaped his approach to networking, why listening is an underrated superpower, and how thinking about your relationships like a portfolio can completely change how you show up.

If you’ve ever thought, “I’ll network when I need to…”
This episode might change your mind.

In this episode, we talk about:

• Why networking is a forever skill, not a short-term tactic
• What’s really happening in today’s job market (and why it feels harder)
• The concept of a “warm network” — and why you can’t let it go cold
• How listening (not talking) makes you a better networker
• Why asking better questions changes everything
• What a “portfolio approach” to networking actually looks like
• The difference between online, local, and travel-based networking
• Why relationships (not resumes) are driving opportunities right now

Meet the Guest

Dinesh Mathew

Business operations executive, consultant, and expert facilitator with a background in market research, focus groups, and organizational strategy.

Dinesh specializes in helping companies improve operations, align leadership, and build systems that actually support growth—while bringing a deeply human approach to networking and relationship-building.

Connect with Dinesh:

• Website
• LinkedIn

Favorite Takeaway

You don’t build a network when you need it.
You build it so it’s there when life inevitably shifts.

Because in today’s world…
your network isn’t optional.

It’s infrastructure.

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What does it take to build a thriving community people actually want to show up for?

In this episode, we sit down with the co-founders of AI Portland, a fast-growing community that has brought together thousands of people around one of the biggest shifts in modern work and business: artificial intelligence.

But this conversation isn’t just about AI.

It’s about curiosity, community-building, networking, and what happens when two thoughtful people decide to start the thing instead of waiting until they feel “expert enough.”

We talk about how AI Portland got off the ground, what they’ve learned from organizing events at scale, how they source speakers, why diverse rooms matter, and what they’ve discovered about what people are really hungry for right now.

If you’ve ever thought, “Could I build something like that?” … this episode is for you.

In this episode, we talk about:

• How AI Portland got started from a simple conversation over wine
• Why you do not need to be an expert to start a community
• What makes an event feel welcoming, thoughtful, and worth coming back to
• How AI Portland grew into a 2,800+ person community
• Why people are craving in-person connection again
• How they choose event topics and source standout speakers
• What they’ve learned about building rooms with more diversity and intention
• Why having a “yes friend” can completely change your trajectory
• The importance of trying things before you overthink them into the grave

Meet the Guests

Megan Notarte

Technology team leader and co-founder of AI Portland, a community focused on demystifying generative AI and its real-world business applications.

Connect with Megan on LinkedIn

Nicole Mors

Product design leader, co-founder of AI Portland, and co-host of the podcast Supercharged by AI.

Connect with Nicole on LinkedIn

About AI Portland

AI Portland is a growing Portland-based community focused on helping people understand and explore artificial intelligence in practical, human, and accessible ways.

They host events, conversations, and gatherings for people across industries — whether you’re deep in tech, AI-curious, or just trying to figure out what the hell any of this means.

Check out upcoming AI Portland events:
https://www.aipdx.info/

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