The Awkward Handshake

Mary Williams & Megan Eckman
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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

  1. 2D AGO

    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? 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’s for you. This conversation pulls apart the myth of “overnight success” and reframes luck as something far less mystical and far more actionable. Spoiler: it’s not about being charming, flashy, or everywhere at once. It’s about showing up consistently, caring genuinely, and building relationships that compound over time. In this episode, we talk about: Why envy and jealousy aren’t character flaws, but data pointsThe difference between posturing and real momentumHow “luck” is usually preparation plus proximityWhy showing up in the right rooms matters more than going to every roomThe hidden labor behind “borrowed audiences” and big collaborationsWhat real reciprocity looks like (and how to spot one-sided networking fast)Why social skills, curiosity, and generosity still outperform hacks and funnelsHow to stop waiting for a fairy godmother and start building your own leverageThis episode is especially for listeners who are tired of transactional networking, allergic to fake hype, and ready to build connections that actually lead somewhere — even if that path is slower, quieter, and far more sustainable. You don’t need more luck.  You need better rooms, better reps, and better relationships. And yes… the numbers never lie — but neither does the room. Keep in touch! Follow Megan Eckman Fat Cap Design PDX Spellbound Follow Mary Williams Sasquatch Media Grounds Sensible Woo

    45 min

  2. 3D AGO

    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 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 into clients, why networking is a long game (even when you’re doing everything “right”), and how patience, volume, and emotional intelligence matter more than the perfect pitch. This is the episode where we get honest about pipelines, timing, consent-based follow-up, and the quiet cost of pushing people before they’re ready. In this episode, we unpack: Why networking is about stacking your pipeline, not instant conversionsThe reality of modern B2B buying decisions (hint: it takes more people and more time than it used to)How many follow-ups is too many—and how to know when to stopWhy “getting a yes” doesn’t mean you have a client (yet)The difference between curiosity and pressure (and why pressure always backfires)How reputation travels faster than you think in local business ecosystemsWhy “good people know other good people” is the most underrated growth strategyWhat readiness really looks like—from both sides of the tableHow networking exposes whether your offer, language, or positioning needs to evolveWe also talk candidly about: Avoidance, money discomfort, and why people say yes when they’re not readyWhy likability and trust matter more than clever sales tacticsHow networking helps you test your message in real timeWhen it’s time to admit you’re in the wrong room—and what to do nextIf you’ve ever left an event thinking “Was that a win… or just a nice conversation?”, this episode will help you recalibrate your expectations without killing your momentum. Keep in touch! Follow Megan Eckman Fat Cap Design PDX Spellbound Follow Mary Williams Sasquatch Media Grounds Sensible Woo

    45 min

  3. 4D AGO

    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 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 conversation dismantles the fantasy that deals are made in the room and reframes networking as what it actually is: the front end of a much longer relationship and decision-making process. This episode covers: Why networking rooms are not sales floors — and never wereThe difference between leads, discovery calls, and actual salesWhy most people are trying to solve a business development problem in the wrong spaceHow many conversations it realistically takes before money changes handsWhy “hot,” “warm,” and “cold” leads still matter more than everHow economic conditions quietly shape decision timelinesWhy desperation is felt immediately — even when it’s unspokenHow treating people like walking ATMs destroys trustYou’ll also hear: Why saying “yes” at an event often turns into a “no” laterHow networking helps you read the economy in real timeWhy follow-up is leadership, not pesteringHow boundaries show up in emails, timing, and toneWhy some rooms feel exhausting — and others feel expansiveThe difference between peacocking and actual tractionAt its core, this episode makes one thing clear: networking isn’t about extracting value. It’s about building context, trust, and enough shared understanding for a real decision to happen later. Keep in touch! Follow Megan Eckman Fat Cap Design PDX Spellbound Follow Mary Williams Sasquatch Media Grounds Sensible Woo

    54 min

  4. 5D AGO

    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 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 conversation is about learning how to choose rooms intentionally instead of saying yes out of obligation or fear of missing out. This episode covers: How to tell the difference between social events and business-driving roomsWhy “good energy” alone doesn’t make an event worth your timeThe role of proximity, consistency, and repetition in choosing eventsWhen ticket price matters — and when it really doesn’tHow audience makeup impacts whether conversations go anywhereWhy some beautifully produced events still fail at connectionRed flags that signal an event isn’t designed for real relationship-buildingHow to decide when to try an event once, twice, or never againYou’ll also hear: How Megan and Mary decide which events get repeat attendanceThe difference between being welcomed and being tolerated in a roomWhy some events feel exhausting instead of expansiveHow to trust your instincts without letting avoidance run the showThis episode helps you stop guessing, stop people-pleasing, and start choosing rooms that support your goals — financially, socially, and emotionally. Keep in touch! Follow Megan Eckman Fat Cap Design PDX Spellbound Follow Mary Williams Sasquatch Media Grounds Sensible Woo

    56 min

  5. 6D AGO

    The Numbers Never Lie

    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 built. The result? A clear picture of what actually works, what takes time, and why one event will never change your business. This episode unpacks: How many networking events Megan and Mary attended together and soloThe surprising volume of coffee chats required to build real momentumWhy consistency, not charisma, drives trust and referralsHow “How badly do you want it?” became the core question behind every resultWhy traffic, logistics, and time complaints miss the real pointThe myth of instant conversions — and what actually leads to paid workHow repeated exposure shortens trust-building timelinesWhy networking improves your messaging, offers, and confidence over timeYou’ll also hear: The origin of the now-famous “What’s your favorite dinosaur?” questionHow neurodivergence shows up in networking roomsWhy kissing a lot of frogs is not a failure — it’s dataWhat it really means to treat business relationships like human relationshipsThis episode sets the foundation for the entire season: networking is iterative, uncomfortable, and deeply human — and it works when you stop pretending otherwise. Keep in touch! Follow Megan Eckman Fat Cap Design PDX Spellbound Follow Mary Williams Sasquatch Media Grounds Sensible Woo

    51 min

  6. SEASON 1 TRAILER

    Welcome to The Awkward Handshake

    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 break down what works, what doesn’t, and how relationships turn into revenue over time. Some episodes feature guests who host or design networking spaces of their own. Others are candid conversations unpacking event culture, follow-ups, coffee chats, and the math behind getting paid. This show is for people who take their business seriously, want better rooms and better connections, and are done pretending the internet is the whole economy. Business is people. Don’t be passive. Keep in touch! Follow Megan Eckman Fat Cap Design PDX Spellbound Follow Mary Williams Sasquatch Media Grounds Sensible Woo

    3 min

Trailer

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.

Information

  • Creator
    Mary Williams & Megan Eckman
  • Years Active
    2K
  • Episodes
    6
  • Rating
    Explicit
  • Copyright
    © 2026 The Awkward Handshake
  • Show Website
    The Awkward Handshake