The Awkward Handshake

Mary Williams & Megan Eckman
  • 5.0 (1)
  • ENTREPRENEURSHIP

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. 5D AGO

    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

  2. APR 24

    Networking in the Wild: BookCon NYC

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

    32 min

  3. 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

  4. 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

  5. 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

  6. MAR 27

    Is There a List of Events? (Finally, Yes.)

    Looking for the best networking events in Portland? Wondering how to meet the right people without wasting time in awkward rooms that go nowhere? In this episode of The Awkward Handshake, we talk with Dominic Kuklawood, creator of PortlandStartupEvents.com, an aggregated event calendar for entrepreneurs, founders, and professionals across the Portland startup ecosystem. Dominic has a unique perspective on networking because he’s not just attending events… he’s tracking the entire landscape. From startup meetups to marketing events, he sees what’s working, what’s missing, and why there’s still more opportunity to build meaningful community. We break down how to find the right networking events, why Portland is not oversaturated with events, and what actually makes a room worth showing up for. If you’ve ever struggled with networking, felt like events were a waste of time, or didn’t know where to start, this episode will give you a clearer path forward. What You’ll Learn  How to find networking events in Portland (without relying on guesswork)  Why there’s still demand for more startup and business events  What makes a networking event successful vs. transactional  How to meet better business connections and collaborators  Why entrepreneurs often experience loneliness—and how events help solve it  The difference between public networking events and private invite-only spaces  A simple framework for hosting your own event (even if you’re not an expert) Resources & Links Portland Startup Events (Event Calendar): https://PortlandStartupEvents.com Connect with Dominic Kuklawood: https://dataspeaks.ai/ Mentioned in This Episode  Luma (event platform)  E-Commerce Northwest  NEXT NW  Portland startup community events Who This Episode Is For  Entrepreneurs and founders in Portland  Creators, freelancers, and consultants looking to grow their network  Professionals tired of awkward or ineffective networking events  Anyone looking to build real relationships in businessKeep in touch!  Follow Megan Eckman Fat Cap DesignPDX SpellboundFollow Mary Williams Sasquatch Media GroundsSensible Woo

    41 min

  7. MAR 20

    Build the Community You Want

    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 usefulHow Jessie’s writers’ group evolved from an in-person meetup into a larger Slack communityWhat it takes to maintain trust in both physical and online spacesWhy strong communities grow best through referrals and real relationshipsThe difference between shallow promotion and meaningful collaborationHow collaboration often takes longer than people expectWhy networking can lead to friendships first and opportunities laterThe hidden labor of being the “mother hen” of a communityWhat happens when you can’t find the room you needOur 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. Keep in touch!  Follow Megan Eckman Fat Cap DesignPDX SpellboundFollow Mary Williams Sasquatch Media GroundsSensible Woo

    53 min

  8. MAR 13

    Why We Love Small Talk

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

    45 min
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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.

Information

  • Creator
    Mary Williams & Megan Eckman
  • Years Active
    2K
  • Episodes
    18
  • Rating
    Explicit
  • Copyright
    © 2026 The Awkward Handshake
  • Show Website
    The Awkward Handshake

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