The Awkward Handshake

Mary Williams & Megan Eckman

The Awkward Handshake is a podcast about networking, business, and what really happens in the room. Hosted by two friends in business who’ve doubled down on the local scene, this show pulls back the curtain on the good, the bad, and the deeply awkward realities of networking. From event logistics and social dynamics to follow-ups, coffee chats, and conversions, we’re talking about how relationships turn into revenue in the real world — not the internet fantasy version. We record from Sasquatch Media Grounds in Vancouver, Washington, and most episodes draw directly from our experiences attending multiple networking events a week across the Portland–Vancouver metro. Sometimes we’re joined by guests who host or design their own events. Sometimes it’s just us, downloading what worked, what didn’t, and what we wish someone had told us sooner. Your hosts are Megan Eckman, co-founder of Fat Cap Design and author of PDX Spellbound, and Mary Williams, founder of Sasquatch Media Grounds and Sensible Woo. This show is for people who take their business seriously, care about doing work that sustains them, and want to stop guessing where clients come from. Expect candid stories, sharp insights, and practical perspective on building a business through real human connection. Business is people. Don’t be passive.

  1. May 15

    Come for the Romance, Stay for the Community with Grand Gesture Books

    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.comInstagram: https://www.instagram.com/blcktinabelcher/?hl=enAbout 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/ Keep in touch!  Follow Megan Eckman Fat Cap DesignPDX SpellboundFollow Mary Williams Sasquatch Media GroundsSensible Woo

    56 min
  2. May 8

    How Kaitlin Carpenter Built Creative Mornings Portland

    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 monthMeet 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: WebsiteInstagramLinkedIn🎨 Want to attend a future Creative Mornings chapter? Find Portland's events and other events worldwide here: https://creativemornings.com/ Keep in touch!  Follow Megan Eckman Fat Cap DesignPDX SpellboundFollow Mary Williams Sasquatch Media GroundsSensible Woo

    53 min
  3. May 1

    Is This a Business Problem… or a Therapy Problem?

    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 Keep in touch!  Follow Megan Eckman Fat Cap DesignPDX SpellboundFollow Mary Williams Sasquatch Media GroundsSensible Woo

    48 min
  4. Apr 17

    Unlock Collective Built Portland’s Most Trusted Queer Network

    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. WebsiteInstagramKeep in touch!  Follow Megan Eckman Fat Cap DesignPDX SpellboundFollow Mary Williams Sasquatch Media GroundsSensible Woo

    48 min
  5. Apr 10

    Your Network Is Forever

    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: WebsiteLinkedInFavorite 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. Keep in touch!  Follow Megan Eckman Fat Cap DesignPDX SpellboundFollow Mary Williams Sasquatch Media GroundsSensible Woo

    49 min
  6. Apr 3

    How AI Portland Built a 2,800-Person Community

    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/ Keep in touch!  Follow Megan Eckman Fat Cap DesignPDX SpellboundFollow Mary Williams Sasquatch Media GroundsSensible Woo

    58 min

Ratings & Reviews

About

The Awkward Handshake is a podcast about networking, business, and what really happens in the room. Hosted by two friends in business who’ve doubled down on the local scene, this show pulls back the curtain on the good, the bad, and the deeply awkward realities of networking. From event logistics and social dynamics to follow-ups, coffee chats, and conversions, we’re talking about how relationships turn into revenue in the real world — not the internet fantasy version. We record from Sasquatch Media Grounds in Vancouver, Washington, and most episodes draw directly from our experiences attending multiple networking events a week across the Portland–Vancouver metro. Sometimes we’re joined by guests who host or design their own events. Sometimes it’s just us, downloading what worked, what didn’t, and what we wish someone had told us sooner. Your hosts are Megan Eckman, co-founder of Fat Cap Design and author of PDX Spellbound, and Mary Williams, founder of Sasquatch Media Grounds and Sensible Woo. This show is for people who take their business seriously, care about doing work that sustains them, and want to stop guessing where clients come from. Expect candid stories, sharp insights, and practical perspective on building a business through real human connection. Business is people. Don’t be passive.

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