The Awkward Handshake

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 u...

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 happe...

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 structur...

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 w...

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...

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 intenti...

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...

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, netwo...

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 per...

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 ref...

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 tow...

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 perspectiv...

In this episode of The Awkward Handshake , Mary and Megan unpack what a “Yes Friend” really is — and why finding one might have less to do with being social… and more to do with nervous system awareness. What started as a conversation about building deeper friendships through networking turned into something bigger: fight, flight, freeze, and fawn responses … and how those stress patterns show up...

In this episode of The Awkward Handshake , we tackle one of the most common networking questions we hear: What if I’m an introvert? Mary and Megan are joined by business strategist and community facilitator Nedra Rezinas to unpack what networking looks like when you don’t thrive in loud rooms, surface-level small talk, or high-volume social energy. Because here’s the truth: Introverts don’t hate n...

In this special episode of The Awkward Handshake , Mary and Megan step outside the usual event debrief to talk about something bigger than networking logistics. This wasn’t originally on the calendar. But when the world shifted — and it felt disrespectful to launch premiere week into that noise — we paused. Then we gathered our community. And what came out of that room sparked this episode. This i...

In this episode of The Awkward Handshake , Mary and Megan dig into one of the most quietly toxic questions in business and creative circles: Are they actually lucky… or are we just not seeing the work behind their network? If you’ve ever left an event feeling like everyone else walked out with deals, connections, and momentum while you walked out with cold fingers and existential dread — this one’...

In this episode of The Awkward Handshake , we tackle the question almost everyone asks after their third lukewarm networking event: “Okay… but how do I actually get clients from this?” Short answer?  You don’t rush it. You don’t pressure people. And you definitely don’t treat humans like walking ATMs. Long answer?  That’s what this episode is for. We break down what really converts conversations i...

If you’ve ever walked into a networking event with the question “Who here can give me money?” quietly screaming in your head — this episode is for you. In Episode 3 of The Awkward Handshake , Megan Eckman and Mary Williams take on one of the most loaded questions in business: how long it really takes to get paid through networking — and why trying to shortcut that timeline usually backfires. This...

Not all networking events are created equal — and going to the wrong ones can cost you far more than the ticket price. In this episode of The Awkward Handshake , Megan Eckman and Mary Williams break down how they evaluate networking events after years of trial, error, and very honest post-event debriefs. From vibe checks and logistics to audience composition and follow-up potential, this conversat...

How many networking events does it really take before you get paid? In this premiere episode of The Awkward Handshake , Megan Eckman and Mary Williams start where most people are afraid to look: the math. After a year of consistent networking across the Portland–Vancouver metro, they finally sat down and tallied the numbers — events attended, coffee chats booked, rooms tested, and relationships bu...

Welcome to The Awkward Handshake — a podcast about networking, business, and what really happens in the room. Hosted by Megan Eckman and Mary Williams, this show pulls back the curtain on the good, the bad, and the deeply awkward realities of building a business through real human connection. Drawing from years of attending networking events across the Portland–Vancouver metro, Megan and Mary brea...