Do the job before you lead it

Hey, Nikki here.

This week we went back in the archives to release another Giggs Rewind episode with Ryan Whelpley, and it’s too good not to remind you of the insights he shared.

Ryan is Touring Director at Red Light Management with over 20 years of live production experience. He started mixing front of house at Nashville’s Wildhorse Saloon, then covered every job on the road for The Lost Trailers. He ran pre-show carpentry and automation for Tim McGraw, then spent nearly seven years as Kip Moore’s tour manager. Now he handles budgets, staffing, and routing for a Red Light roster.

Why this one matters:

Ryan didn’t start in a management seat. He started driving the van and learning gear he’d never touched. By the time he was setting budgets for a full roster, he’d already done nearly every job those numbers touch.

#1 Know how long the job actually takes

Ryan learned automation from scratch on a Tim McGraw run, spending two weeks programming video walls and motors he’d never touched. That instinct carried him from mixing front of house to running budgets today.

Takeaway: Leading well starts with knowing what the work around you actually costs.

Try this: Pick one job on your team you’ve never done. Ask someone to walk you through their day this week.

#2 Build the role, don’t wait for it

Ryan watched opening acts get thrown onto the road with managers who weren’t built for touring logistics. So he pitched something new at Red Light: bring him in-house to handle the details. Nobody asked him to build it. He saw the gap and made the case.

Takeaway: The best roles don’t always exist yet. Somebody has to notice the gap first.

Try this: Name one recurring problem in your camp that nobody officially owns. Pitch the fix to whoever can greenlight it.

#3 A near miss should change the next plan

Years ago, on a tight connection into Winnipeg, Ryan’s team flew commercial instead of private to save money. The flight got delayed, and they split the crew across the last open seats and needed a police escort just to get the artist changed and onstage in time.

After that, Ryan stopped taking that kind of routing risk. When a similar gap showed up on another artist’s schedule, he went private without hesitating.

Takeaway: A near miss is information. Use it before you need the lesson twice.

Try this: Look at your riskiest routing call coming up. If a past close call already taught you the answer, use it.

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If you want the full conversation, watch the Giggs Rewind episode with Ryan Whelpley.
SPOTIFY | APPLE | YOUTUBE

— Nikki

P.S. One line I loved: “It should be fun. It’s a privilege to do this. Work hard, show up, have a good attitude, even on minimal sleep.” It’s a privilege, and it can be exhausting, both at once.