The Awkward Handshake

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 GuestsMegan NotarteTechnology 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 LinkedInNicole MorsProduct design leader, co-founder of AI Portland, and co-host of the podcast Supercharged by AI.Connect with Nicole on LinkedInAbout AI PortlandAI 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 EckmanFat Cap DesignPDX SpellboundFollow Mary WilliamsSasquatch Media GroundsSensible Woo

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 & LinksPortland Startup Events (Event Calendar):https://PortlandStartupEvents.comConnect 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 EckmanFat Cap DesignPDX SpellboundFollow Mary WilliamsSasquatch Media GroundsSensible Woo

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 GuestJessie 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 mattersIf 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 EckmanFat Cap DesignPDX SpellboundFollow Mary WilliamsSasquatch Media GroundsSensible Woo

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 conversationsKeep in touch! Follow Megan EckmanFat Cap DesignPDX SpellboundFollow Mary WilliamsSasquatch Media GroundsSensible Woo

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 perspective on curiosity, connection, and the power of being a genuinely interesting human in professional spaces. Together, the three of them unpack how real relationships form, why curiosity is one of the most underrated networking skills, and how conversations become more meaningful when we let people show up as full humans instead of job titles.If you’ve ever felt boxed in by the pressure to “deliver the perfect pitch,” this conversation might be the permission slip you didn’t know you needed.Because the best rooms don’t reward the most polished pitch.They reward the most human presence.In This Episode, We Talk About:• Why elevator pitches can sometimes shut down real conversation• The role curiosity plays in building authentic connections• How to ask better questions in networking settings• Why being interesting matters more than sounding impressive• The difference between transactional networking and relational networking• How curiosity leads to stronger collaborations and referrals• Why your personality and interests belong in the room tooConnect with our guest, Kellen Moody:Kel's WebsiteKel's LinkedInKeep in touch! Follow Megan EckmanFat Cap DesignPDX SpellboundFollow Mary WilliamsSasquatch Media GroundsSensible Woo

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 business rooms when you’re trying to connect, stay grounded, and not accidentally agree to something you regret.A Yes Friend isn’t just someone you like. It’s someone who helps you get a better outcome in the room.And yes — it’s work. The good kind.In this episode, we talk about:Why “Yes Friends” don’t just appear out of nowhereHow fight/flight/freeze/fawn responses show up at networking eventsWhat it looks like to support a friend when they freeze or fawnThe “emotional readiness weight class” idea — and why it mattersWhy some people disappear at events (and how that impacts trust)How to be an “exit buddy” and rescue each other from conversations gracefullyThe underrated power of small talk as social lubrication while your brain catches upWhy networking can trigger intense emotions (even if you didn’t expect it)How being a connector creates compounding returns over timeWhy follow-up can save almost any awkward momentThe truth: you can’t solve this only in your home office — you have to do reps in the real worldIf you’ve ever wondered why networking feels harder than it “should,” this episode will give you a new lens — and a much kinder interpretation of your own behavior.Keep in touch! Follow Megan EckmanFat Cap DesignPDX SpellboundFollow Mary WilliamsSasquatch Media GroundsSensible Woo

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 networking... they hate bad networking.Together, we explore what it means to build connection in ways that feel grounded, sustainable, and aligned with your nervous system — without disappearing from rooms that matter.In this episode, we talk about:Why introversion is not a business liabilityThe difference between overstimulation and disinterestHow to design networking experiences that support depthWhat “Quiet Networking” looks like in practiceWhy smaller rooms often outperform bigger onesHow to protect your energy without isolating yourselfWhy authenticity beats performance — every timeThe power of 1:1 follow-up for introverted foundersIf you’ve ever left a networking event feeling drained, awkward, or like you “did it wrong,” this episode will feel like permission to do it differently.About Our GuestOur guest for this episode is Nedra Rezinas, a business strategist and coach for introverted and empathy-driven solopreneurs.Nedra helps founders build businesses that reflect their true values without forcing themselves into extroverted molds that don’t fit.She’s the founder of Quiet Networking, a Portland-based networking group designed specifically for people who prefer meaningful conversation over volume and velocity.You can connect with Nedra here:https://www.nedrarezinas.com/https://www.linkedin.com/in/nrezinas/Attend the next Quiet Networking event when you register hereKeep in touch! Follow Megan EckmanFat Cap DesignPDX SpellboundFollow Mary WilliamsSasquatch Media GroundsSensible Woo

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 is a conversation about values. About fear. About silence. About what it means to lead — especially when you don’t feel ready.Because “silence is complicity” sounds simple on social media. In real life, it’s more complicated.In this episode, we unpack:Why we postponed premiere week — and what that decision modeledWhat came out of our January coffee party with community organizersThe tension between being authentic and being performativeWhy social media isn’t the only (or best) place to take a standWhat “10 out of 10 people” means in a networking roomHow to make your values clear without becoming a political punditWhy some leaders are waking up late — and what that costsThe fear of “getting it wrong” publiclyThe difference between loud and effectiveWe also talk about:Economic power as a form of resistanceFollowing the money — both who pays you and who you payHow values misalignment quietly wrecks your health and your businessSmall ways hosts can make rooms saferWhen to call someone out — and when to simply walk awayHow reciprocity, visibility, and association shape safetyThis episode isn’t about perfection. It’s about participation.It’s about recognizing that business is people — and people are living through something real right now.And whether we like it or not, that shows up in our networking rooms.Keep in touch! Follow Megan EckmanFat Cap DesignPDX SpellboundFollow Mary WilliamsSasquatch Media GroundsSensible Woo

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 EckmanFat Cap DesignPDX SpellboundFollow Mary WilliamsSasquatch Media GroundsSensible Woo

They unpack why networking is a long game and how stacking your pipeline beats instant wins. Topics include modern B2B buying taking more time and people, and consent-based follow-up limits. They cover testing your message in real time, spotting genuine readiness versus polite yeses, and when to change rooms or offers. Expect practical takes on referrals, consistent presence, and approaching high-value prospects.