Sideways Rain

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.

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. In this one-on-one conversation with JR, Chris walks through the storm of losing identity to roles, the quiet doubt of the first month, and the moment he chose alignment over optics.

He breaks down the umbrella that carried him forward. Perspective came first. Success meant creating value while being present for his family. Then he added structure. Clear service models, simple pricing, and an operating rhythm that made the business look and feel real. He resisted the urge to buy heavy tools and proved that disciplined spreadsheets and consistent follow up can beat a shiny platform. Finally he invested in Centers of Influence, one coffee at a time, asking questions like “What keeps you up at night” and “What would make your business one percent better.”

Chris shares fast lessons leaders can use today. Process beats heroics. Hiring is a business strategy, especially when you scale across borders. Change management works when you lead with clarity and empathy and invite ownership. He talks about finding traction in financial services, why a solid batting average is a more honest goal than perfection, and how the first retainer and a sustainable weekly cadence signaled clear skies. The best review came at home when his wife said “You are back.”

We close with what is next for the industry. AI is a tool, not a replacement. Relationships and soft skills are rising. Chris leaves practical advice for early career pros. Do the blocking and tackling. Build structure before you think you need it. Invest in people who think differently than you do. Keep walking through the sideways rain.

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 invites to choose (one!), plus the top mistakes to avoid and three things to do today before wheels-up.

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” lesson, and the slow but real shift from sales-led to marketing-led data. Howard also riffs on why face-to-face remains a high-trust channel in an AI world, how festivalization is changing event DNA, and what distributed workforces really need from meetings. He closes with three personal tenets that carried him through cancer—control what you can, practice gratitude, and ask for help—bringing the episode back to measurable impact and perseverance.

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, and discovered the “secret science” behind live events. From building resilience to empowering people to see capabilities they didn’t know they had, Jack offers a grounded perspective on what it takes to lead when the playbook disappears.

Listeners will walk away with insights on moving faster with confidence, finding strength in community, and why sometimes the best career advice is the simplest: just go do it.