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 productionneeds, and how planners can get to a faster yes or no before they sign.

Shanondoah also drops a career resiliency mindset that every event pro needs: keep your bag packed, keep your network active, and make it easy for people to help you when the wind shifts.

You will also hear her lightning round picks, including two must read books for event professionals: The Art of Gathering and Unreasonable Hospitality.

Links and references
Shanondoah’s podcast: https://open.spotify.com/show/0l3OjPoH7xMGc3GRiPfoav?si=43785f9408f444ad
Shanondoah on LinkedIn: https://www.linkedin.com/in/shanondoahnicholson/
Book mentioned: The Art of Gathering by Priya Parker: https://www.amazon.com/Art-Gathering-How-Meet-Matters/dp/1594634939/
Book mentioned: Unreasonable Hospitality: https://www.amazon.com/Unreasonable-Hospitality-Remarkable-Giving-People/dp/0593418573/

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 is trying to mess it up, but the math is wrong, the data gets repeated like truth, and planners get stuck holding the bag.

We get opinionated about why most event tech fails. Suite bloat turns tools into admin jobs. Training becomes a tax on bad design. Workflows still depend on waiting days for PDFs and humans to confirm what should be obvious. Then we talk about why Cvent has such a massive foothold and why dominance does not equal good enough when the real job is confidence, not complexity.

Finally, we lay out the clear skies. WIFT is not a platform to manage. It is a Yes or No engine. A production aware fit check that gives you an answer in about five seconds, with a layout you can share immediately, with zero training. If you are a corporate planner, hotel CSM, or sourcing manager, this one is for you.

Subscribe for updates at wift.ai and get the behind the scenes series on how to stop guessing and start making space decisions with certainty.

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 identity, your confidence, and your definition of success—and how he reframed the whole thing from “a title” to “a purpose.” We get into why hustle culture keeps people stuck, why real progress usually requires support, and why AI can be an accelerator… but it can’t replace judgment.

We also break down Michael’s practical framework Attract–Connect–Close for leaders trying to move from “good to know” to “good to do”—whether you’re pitching, fundraising, selling, or just trying to walk into bigger rooms with more confidence.

In this episode:

• The sideways-rain moment: when the dream doesn’t go how you planned

• How to separate purpose from packaging

• Why “doing it alone” is the silent growth killer

• AI as a tool, not a substitute for perspective and accountability

• A simple framework to communicate clearly and close with confidence

If you want a description that’s shorter (2–3 sentences) or more punchy for LinkedIn, tell me which title you choose and I’ll match the tone.

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 of quitting, Anthony and his partner learned fast and kept saying yes. Today Motion Flix runs 20 to 40 events a month and has expanded from Florida into major markets like LA, Miami, Vegas and beyond. We talk about what really separates them from “screen pop up” vendors: experience design, deep customization, sponsor strategy, licensing done the right way, and even silent disco headphones for residential spaces.

Anthony also shares the real scaling challenge: how to systemize custom experiences without losing the magic. Plus a few founder truths he lives by: be your own biggest fan, take the opportunity, and keep building when the weather turns.

Motion Flix on Instagram: https://www.instagram.com/motion.flix/

Anthony Cortes on Instagram: https://www.instagram.com/anthonycortes8/

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 umbrellas that work when the rain comes sideways — and how to stack the deck for more clear days in 2026.

JR and Kris break down the real storms that derail New Year momentum: false optimism, too many priorities (which turns into none done), and the constant noise of scrolling and reacting. Then they get practical: pick one thing for Q1, build a “Not List” to protect it, run a weekly Friday “weather report,” and adopt a calmer, more powerful version of “Be the Duck” — fewer words, fewer decisions, slower pace, stronger strokes.

And to make it stupid simple, we end with a step-by-step 7-Day Clear Skies Challenge you can complete in 7 minutes a day — including a scorecard on Day 7 to lock it in and repeat weekly.

7-Day Clear Skies Challenge (fillable PDF)

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 thousand dollars, and eventually building Plugg — a nearshore staffingfirm connecting U.S. companies with top talent across Latin America while he raises his family in Hawaii.

Brian breaks downthe real differences between offshore and nearshore, why “talent pockets”across LATAM matter, and how culture, time zones, and trust can make or breakyour global hiring strategy. He’s candid about the rookie mistakes he made withpartners, the ego boost of landing big-name clients during the VC boom, andwhat happens when the market tightens and your model suddenly stops working.

If you’re a founder,agency owner, or hiring manager who’s nearshore-curious — or you’re in themiddle of your own investor or co-founder storm — this one will hit home.You’ll walk away with a clearer understanding of how to think about LATAM talent, what alignment with investors and partners actually looks like, and why nobody is coming to save you… but that’s not a bad thing.

You can find Brian on LinkedIn, Plugg's website, and his "TheNearshore Café" podcast.

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 tech business right as Covid hit. He gets into where event tech has fallen behind, how customization and AI are finally catching up to how audiences actually consume content, and why he builds his company as a contractor first community where people see the true fruits of their labor. They dig into trust, emotional management, and leading with transparency so your team actually feels invested, not just employed. Plus, a lightning round on watch collections, dream cars, and bold Super Bowl predictions.

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 see and believe. They question whether posting has become a necessary chore for legitimacy, dig into the blurred line between connection and manipulation, and share candid reflections on what it means to “own your data” in a world that profits from your attention.

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: losing security, rebuilding confidence, and learning how to manage emotions instead of being ruled by them. From anxiety-driven hustle culture to the myth of “always on,” they explore what it really means to lead with EQ, and why kindness, awareness, and self-reflection might just be the ultimate competitive edge.

Key topics:

• How emotional intelligence transforms setbacks into growth

• Why rejection is often redirection

• Managing self-doubt in high-performance environments

• The danger of hustle culture and the myth of constant motion

• The role of empathy in leadership and life

Learn more about Rich:🌐 Website: www.richbracken.com💼 LinkedIn: linkedin.com/in/rich-bracken

Listen if you’ve ever felt the storm, and needed to remember that sometimes the rain is what makes you grow.

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 to tight internal alignment on what/how/why, and the hard-won lesson to hire his weaknesses. We dig into practical behaviors leaders can apply tomorrow—own it don’t wear it, after-action honesty, and designing moments that show the doing, not just the telling. Steve also shares his “Rest, Fuel, Move” foundation and a simple micro-drill you can test in your next meeting. Clear skies come from reps, not rhetoric.