The Awkward Handshake
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.
Episodes
20 episodes
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 ind...
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 Portla...
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...
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) shari...
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 Un...
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 ...
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 on...
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, crea...
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 l...
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 e...
You’re More Than Your Elevator Pitch
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 peop...
Finding Your Yes Friend
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 conversa...
Networking for Introverts
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<...
Values Matching: What Silence Costs in Business
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 shif...
Were they lucky?
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?<...
How Do I Get Clients Through Networking?
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...
Who Can Give Me Money? (And How Long Until I Get Paid?)
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 William...
Which Events Are Worth It?
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 networki...