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.

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 taking risks, and the importance of support systems when the storm hits. He shares candid insights on what founders get wrong about legal work, why the billable hour is broken, and how tech is reshaping the future of law.

We also get into family life, real talk on networking, and yes — the eternal debate: corn dog vs. Pronto Pup.

Whether you’re a founder, a lawyer, or just someone navigating your own sideways rain, this episode is a reminder that the umbrella is often closer than you think.

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 pharma space—to the wild, unpredictable world of blockchain and Web3. What he found was a different pace, a different kind of audience, and a whole new way of measuring success.

This episode is a deep dive into:

• The volatility of tech budgets—and how to stay grounded when everything changes overnight

• What it means to produce with purpose and how to create real impact for the communities you serve

• The surprising differences between traditional corporate events and blockchain activations

• Why soft skills, flexibility, and empathy are the real power tools in today’s events landscape

• How Ben has kept evolving his mindset while staying true to what he learned in his early days at 180

Whether you're navigating a career pivot, trying to find stability in chaos, or just wondering what blockchain events actually look like—this one’s packed with perspective, humility, and a few laughs along the way.

#SidewaysRain #EventProduction #Web3Events #PolygonLabs #CareerPivots #StartupLife #PharmaVsBlockchain #EventProfs

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, the lessons they’ve learned from over-sharing, and why marketing early (with care) is essential. Whether you’re building tech or launching anything new, this one’s for the builders navigating the unknown.

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 twists, pivots, and risks that shaped his journey. They dive deep into the importance of listening, honest feedback, scope creep, and how customer success skills can become the backbone of a great product career.

Whether you’re in tech, building a startup, or just figuring out your next move, this one’s for you.

Topics include:

• Why Kenny quit without another job—and what happened next
• Product management vs. customer success
• The power of listening and honest user feedback
• Dealing with ambiguity, scope creep, and tough pivots
• What makes a great PM (and why it’s not what you think)
• Lessons from building WIFT, Oura Ring, and beyond

Links:

• Email: [email protected]
• LinkedIn: https://www.linkedin.com/in/kenny-corum
• Product Podcast: https://podcasts.apple.com/us/podcast/the-product-podcast/id1219400787
• Oura: https://ouraring.com/
• Lucky Buns: https://www.luckybuns.com/location/union-market-location-lucky-buns/

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 going.

They talk about what sparked the idea, the decision to go with a barber-recommended developer (yes, really), the highs of IMEX 2024, the sting of rejection from a major player, and why humility, patience, and persistence matter more than any pitch deck.

This one’s for anyone who's ever tried to build something from scratch—and kept going even when the shine wore off.

Topics covered:

• How WIFT started (and why it wasn’t supposed to be a tech company)

• Choosing the right partners (and what makes someone trustworthy)

• MVP missteps and how much it really costs

• The power of listening to your market

• Learning to celebrate wins—without getting too comfortable

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 means to create an event that hits close to home.

Sydney shares their family’s Make-A-Wish story, the full-circle journey of giving back, and how personal connection can elevate not just the work, but the entire purpose behind it. Together, they explore the balance between professional execution and emotional investment, and why finding meaning in your work matters more than ever.

This one’s about hope, purpose, and producing with heart. No rain today. The sun is out.

Connect with Sydney on LinkedIn: https://www.linkedin.com/in/sslyy/

Donate to Make-A-Wish MN: https://wish.org/minnesota