PODCAST · business
Sideways Rain
by J.R. Spiess and Kris McNeil
Storms don't only come straight at you. Sometimes they blow in from the side. Season two of Sideways Rain is a full slate of those stories, told by the people who build meetings, events, and experiences for a living. Hosts J.R. Spiess and Kris McNeil sit down with founders, planners, and production pros and walk through the same three beats: the storm, when things went sideways; the umbrella, how they adapted in the moment; and clear skies, what they changed and where they landed.
Episodes
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21. Turn Left at the Wall
Some guests survive a storm. Liz Lathan walked straight into one with her eyes wide open. Years into building her career in the association world, Liz had earned her director title and hit the ceiling of a four-person shop. Then another executive director dangled the thing every ambitious person...
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20. Strength by a Thousand Paper Cuts with Alyssa Frank
Most guests bring us one storm. Alyssa Frank brought a thousand paper cuts. Alyssa is a CMP with 15 years in meetings, events, and incentive travel, and the founder of Covalent Events and Travel. She slid into the industry from a front desk in college, got handed events, and learned the job on…
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19. Four Times the Floor Dropped with Kevin White
Most people in events have one storm they'd like to forget. Kevin White has four. Across 30 years in experiential design, Kevin watched his whole industry go under four separate times: the dot-com bust, 9/11, the 2008 crash, and the Covid shutdown. Not rough patches. The floor gone, no lifeboat…
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18. Stay Curious, Stay Bold: Andrew Roby on Building the Business Behind the Events
Most people get into events because they love the energy. The problem is loving events and knowing how to run an event business are two completely different things. Andrew Roby, founder of Andrew Roby Events, learned that the hard way. Coming out of the Army in 2005 after serving at the Old Guard...
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17. Six Storms Nobody Wants to Say Out Loud
The industry treats the last 48 hours before an event like a war story. The 3 a.m. rebuild. The no-sleep show day. The save. We've all got those stories, and we need to stop telling them like they're flexes. If you're in survival mode the week of show, something already broke six months ago. This...
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16. When the Vendor Vanished with Evan Babins
What happens when an AV vendor cancels 72 hours before a half-million-dollar international event and the audience never knows? In this episode of Sideways Rain, JR sits down with Toronto-based event leader Evan Babins to unpack one of the wildest behind-the-scenes storms you’ll hear in the…
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15. Keep Your Bag Packed with Shanondoah Nicholson
In this episode of Sideways Rain, JR and Kris sit down with Shanondoah Nicholson, a corporate event planner turned full time freelancer and the host of Beyond the BEO. Together, they tackle the “capacity lie,” why hotel capacity numbers often collapse the moment you add real world…
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14. The Capacity Lie: Why Event Tech Fails
In this JR and Kris episode of Sideways Rain, we open with a scar we have seen for 20 years. Teams contract space based on a capacity number, then production shows up and the room is suddenly too small once you account for stage, screens, FOH, camera lanes, backstage, ADA, and real egress. No one...
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13. The Detour That Made the Mission
Michael C. Clark thought the path was clear: leave investment banking in NYC, stop his life, and chase a lifelong goal—law school—while married with two little kids. Then the plan didn’t end the way he expected. In this episode, Michael walks us through what that kind of pivot does to your...
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12. Never Say No: The Operating Playbook Behind Motion Flix
Anthony Cortes started Motion Flix in the middle of the pandemic with a simple idea: outdoor movie nights that let people gather safely. Then the first “neighborhood promo” turned into a perfect storm: a popcorn machine fire, power loss, and an inflatable screen collapsing mid Toy Story. Instead…
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11. Stop Waiting for Perfect Conditions
Everybody loves January because it feels like a clean slate — like clear skies are guaranteed. But if you’ve lived any amount of life (or built anything), you already know the wind shifts whenever it wants. So this is not a “resolutions” episode. It’s a weather strategy episode: how to build...
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10. From Founder Fallout to Nearshore Flow with Brian Samson
What happens when you walk away from a company you co-founded, right after your first child is born… and then a global pandemic wipes out your pipeline? In this episode of Sideways Rain, Brian Samson talks about leaving a misaligned investor-backed startup, betting on himself with just a couple...
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9. Betting on Yourself in Event Tech with Chris Donaldson
Event tech leader Chris Donaldson joins JR and Kris to talk about what happens when you stop being a cog in someone else’s wheel and bet on yourself instead. Chris shares how sobriety, burnout, and a lack of real impact pushed him out of a “safe” full time role and into launching his own event…
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8. Touch Grass: The Social Media Storm
In this unplanned but powerfully real episode, J.R. and Kris tackle a modern sideways rain — our collective addiction to social media. What started as a simple mic check turned into a raw conversation about authenticity online, the illusion of influence, and how algorithms quietly shape what we…
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7. Feel the Rain: Emotional Intelligence with Rich Bracken
When keynote speaker and emotional intelligence expert Rich Bracken was let go from a job he loved, while doing great work, it could’ve been the end of his story. Instead, it became the beginning of something bigger. In this episode, J.R. talks with Rich about the moment that changed everything:...
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6. Good to Know Isn’t Good to Do: Steve Shenbaum on Making Communication Stick
Founder of Game On Nation, Steve Shenbaum, joins Sideways Rain to unpack why great intentions and catchy ideas aren’t enough—and how turning “good to know” into “good to do” changes rooms, teams, and results. Steve walks through his storm of authentically marketing a communication firm, the pivot...
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5. From Titles to Alignment with Chris Hall
Chris Hall spent more than 15 years inside global organizations leading a team that produced thousands of events and grew to about 60 people. Earlier this year he was let go. Instead of chasing another title he launched Middlehall Collective with a laptop, a plan, and a new definition of success....
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4. IMEX America: Your Field Guide (Shoes, Smart Monday, and the 30/5/5)
JR and Kris compress the IMEX learning curve into one fast listen: why the show matters, a plain-English breakdown of registration types, first-timer tips (buffers, water, sneakers), floor-flow at Mandalay Bay, Smart Monday picks, how to pace Tues–Thurs, the 30/5/5 meeting cadence, which evening...
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3. ROI Without the Fluff: Howard Givner on Measurement, Festivalization, and Resilience
Howard Givner cuts through the buzzwords to explain ROI as an actual calculation—“was the juice worth the squeeze?”—and how to frame results with stakeholders before the show even starts. We get into relative ROI (why a good event can still lose to a better alternative), the “Camp Groupon”…
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2. Just Go Do It: Leadership, Resilience, and the Secret Science of Live Events
When the pandemic shut down the meetings and events industry overnight, Jack DeVries, President of Showcore, had a choice: freeze or adapt. In this episode, Jack shares how he pushed himself to learn as much as possible about every corner of his business, led his team through massive uncertainty,...
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1. Betting on Yourself: Pranav Gangele and the Storms of Startup Law
Season 2 kicks off with big energy as JR and Kris bring on startup and corporate attorney Pranav Gangele to talk about his sideways rain moment — leaving the comfort of Big Law to bet on himself at a smaller shop. Pranav opens up about the golden handcuffs of guaranteed salary, the anxiety of...
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16. Producing in the Wild: Ben Illies on Budget Swings, Blockchain, and Finding Meaning
In Episode 16 of Sideways Rain, JR and Kris sit down with Ben Illies, Senior Manager of Events at Polygon Labs, to talk about what it really means to build events inside an industry that’s constantly shifting. Ben reflects on his move from leading shows at The 180 Group—including time in the…
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15. Selling Before It’s Built: Marketing in the Messy Middle
How do you market a product that isn’t done yet—without misleading your audience or giving your competitors a head start? In this episode, JR and Kris get honest about what it means to market WIFT while still deep in development. They talk through the tension between transparency and strategy…
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14. Breaking Into Product: Risk, Resilience, and the Power of Listening
In Episode 14 of Sideways Rain, JR and Kris sit down with product manager Kenny Corum (formerly of Axios, now at Oura) to unpack the reality of working in product—and what it really takes to break in. From walking away from a steady job to building trust with skeptical customers, Kenny shares the...
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13. Two Years In: The Real Startup Story Behind WIFT
On Episode 13 of Sideways Rain, JR and Kris sit down for a raw, reflective, and at times surprising look back at the two-year journey of building WIFT—from a casual birthday-day LinkedIn message to beta pilots, tough pivots, missed timelines, surprise wins, and the resilience it takes to keep...
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12. Producing with Purpose: The Impact of Make-A-Wish with Sydney Long
In this special episode of Sideways Rain, we step away from entrepreneurship and tech to focus on producing with heart. Recorded onsite at the Make-A-Wish Minnesota Wish Ball, JR sits down with Sydney Long, graphics producer at The 180 Group and sibling of a former Wish Kid, to talk about what it...
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11. Funding Without the Marble Floors: Lending for Real Life Entrepreneurs
This week on Sideways Rain, we sit down with Darryl Appiah, a small business loan officer with CDC Small Business Finance and Momentus Capital, to break down one of the most stressful (and misunderstood) parts of building a business: getting funding. But this isn’t just a conversation about...
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10. Mid-Career, Full Heart: Writing the Life You Want
This week on Sideways Rain, we welcome Mary Bellettieri—events industry veteran turned self-published author. Mary opens up about her bold mid-career pivot into writing, what it really takes to bring a book to life without a publishing deal, and why chasing your dreams isn’t just for…
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9. Past the MVP: Navigating the Funding Desert and Winning Investor Confidence
In this episode, Kris and J.R. break down the often-overlooked phase of startup life: what happens after you launch your MVP (Minimum Viable Product). They dive into the real challenges of raising capital without revenue, building traction, and proving market fit—not just product viability. From...
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8. Strategic by Design: Global Planning, Leadership, and the Realities of Event Execution with McKenna Dressel
This week, we sit down with McKenna Dressel, Associate Director of Global Meetings & Conventions – Ophthalmology at Regeneron, to talk about her journey from chemistry and manufacturing to high-stakes global event planning. She shares how managing teams on the production floor shaped her approach...
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7. From Stress to Strategy – Finding Balance in Event Planning with Naomi Tucker
In this episode of Sideways Rain, we sit down with Naomi Tucker, strategic events consultant, high-performance coach, and founder of Planners on Purpose. Naomi shares her expertise on managing stress, avoiding burnout, and finding joy in the demanding world of event planning. We discuss the...
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6. Dodging the Downpour: How the Meetings Industry Can Thrive Despite Tariffs
Big news is shaking up the meetings and events industry—overnight tariffs on Canada, Mexico, and China are about to drive costs through the roof. In this episode, we break down the real impact: skyrocketing AV costs, hotel rate hikes, and catering price spikes that will hit corporate events hard....
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5. The Truth About Work-Life Balance: Can Entrepreneurs Really Have It?
Work-life balance. Everyone talks about it, but is it actually real when you're running a business? In this episode, J.R. and Kris break down the myth of balance, sharing their personal experiences juggling business, family, and life’s unexpected challenges. They dive into: The chaos of balancing...
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4. From Rolling Cables to CEO – J.R.'s Journey with The 180 Group
In this episode of Sideways Rain, J.R. is flying solo to share his journey from rolling cables on show sites to becoming the CEO of The 180 Group. It wasn’t a straight path—there were pivots, challenges, and a whole lot of sideways rain along the way. He’ll take you behind the scenes of: How J.R....
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3. Navigating the Chaos of Tech & Innovation
In this episode ofSideways Rain, we sit down withSean Sanusi, a software engineer and tech consultant who has worked across startups, corporate innovation, and even government projects. We dive into the unpredictable world oftechnology development, from building software under tight deadlines to...
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2. The Power of PR in Business
In this episode of Sideways Rain, we dive into the wild and unpredictable world of public relations with Joe Krasean, a PR pro with a global perspective, based in Germany and freelancing with companies like Black Unicorn PR. Whether you're a startup navigating fierce competition or a growing...
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1. Pilot: What is Sideways Rain?
In this debut episode of Sideways Rain, hosts JR Spiess, CEO of The 180 Group, and Kris McNeil, Co-Founder and CTO of WIFT, dive into the unpredictable journey of innovation, entrepreneurship, and building impactful businesses. Together, they share their expertise in event production and tech...
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ABOUT THIS SHOW
Storms don't only come straight at you. Sometimes they blow in from the side. Season two of Sideways Rain is a full slate of those stories, told by the people who build meetings, events, and experiences for a living. Hosts J.R. Spiess and Kris McNeil sit down with founders, planners, and production pros and walk through the same three beats: the storm, when things went sideways; the umbrella, how they adapted in the moment; and clear skies, what they changed and where they landed.
HOSTED BY
J.R. Spiess and Kris McNeil
CATEGORIES
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Frequently Asked Questions
How many episodes does Sideways Rain have?
Sideways Rain currently has 37 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Sideways Rain about?
Storms don't only come straight at you. Sometimes they blow in from the side. Season two of Sideways Rain is a full slate of those stories, told by the people who build meetings, events, and experiences for a living. Hosts J.R. Spiess and Kris McNeil sit down with founders, planners, and production...
How often does Sideways Rain release new episodes?
Sideways Rain has 37 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Sideways Rain?
You can listen to Sideways Rain on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Sideways Rain?
Sideways Rain is created and hosted by J.R. Spiess and Kris McNeil.
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