Sideways Rain

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 week, no guest. Just JR and Kris, no filter, putting six things the events industry doesn't talk about straight on the table: The last-minute chaos myth, and why "two weeks out" should be the line every team holds. What clients are actually paying for (hint: it's not the gear, it's the person picking up the phone). The planner with no power. Positional authority, show-week changes, and the cost when nobody backs them up. Vendor red flags, the "hard no" that kills relationships, and the trick of pricing yourself out instead of saying it. AI in events. Where it's actually useful, where it's just an LLM in a dress, and why we're in a "lazy AI era" right now. The room that looked right on paper, and why JR says 75% of events get sourced wrong before the contract is even signed. Plus a lightning round on what the production industry needs to stop doing, the most underrated event city in America, and one piece of advice each for anyone early in their career. If you're a first-year planner who made it to the end of this episode, JR's giving you a year of WIFT for free. Send him a DM. New episodes weekly. Hit follow, share with somebody who needs to hear it, and we'll see you next week.

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 meetings and events world. Evan shares how a last-minute vendor collapse over the Atlantic forced him into instant problem-solving, why relationships saved the show, and what that experience taught him about due diligence, calm under pressure, and the long game in business. The conversation also goes beyond the story itself into what it really means to elevate the craft in this industry. JR and Evan get into personal brand, collaboration versus gatekeeping, talent versus technology, and where AI is actually useful for event professionals right now. It’s a conversation about the hidden work below the surface, the value of real networks, and why the best operators make chaos look seamless. Evan on LinkedIn: https://www.linkedin.com/in/evanbabins/

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 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 [https://open.spotify.com/show/0l3OjPoH7xMGc3GRiPfoav?si=43785f9408f444ad] Shanondoah on LinkedIn: https://www.linkedin.com/in/shanondoahnicholson/ [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/ [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/ [https://www.amazon.com/Unreasonable-Hospitality-Remarkable-Giving-People/dp/0593418573/]

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 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.

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 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.