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Deep Dive: RAGBRAI with Ride Director Matt Phippen

Iowa's biggest summer tradition is 13 days out, and we sat down with the man steering it all. Matt Phippen has served as RAGBRAI Ride Director since January 2022, guiding what's known as the oldest, longest, and largest recreational bicycle touring event in the world across the state each July. This will be his fifth ride at the helm. Phippen grew up in Oelwein, where his parents once hosted a ride team that pitched 50 tents in their front yard during a 1990 overnight stop. That childhood memory hooked him for life, even though his own first RAGBRAI ride in 1998 was, in his words, "the worst experience of my life."

Before taking the reins, Phippen managed the cycling division at Scheels sporting goods, joining the annual June route-inspection rides that precede every RAGBRAI. Now he's the guy who took riders off-route into Minnesota for the first time in event history, opened up Iowa's gravel roads to the pack, and launched new weekend rides that spread the RAGBRAI spirit statewide well beyond its official week.

In this wide-ranging conversation, Matt breaks down:

• What RAGBRAI really is — Iowa's rolling family reunion, connecting small towns of 70 people to riders from 50 states and 20 countries, plus the unscripted magic of it (like the year he ended up selling ice cream out of the back of a Peppy's van in Waterloo)
• The safety machinery behind the fun — how RAGBRAI's relationship with Iowa State Patrol, DOT, and county law enforcement starts every September, why 20,000 registered riders really means planning for 40,000 people on the road, and the "super sag" protocol (semis, school buses, and staged pickup points) built after the grueling 50th-anniversary ride
• A day in the life of the director — up at 3–4 a.m., waking Dream Team kids with a cowbell before sunrise, then riding the route town to town in a state trooper's cruiser until the last riders roll in at night
• Dream Team — the youth cycling program that pairs kids from all backgrounds with mentors, gifts them a bike if they complete training rides and RAGBRAI itself, and gives Matt one of his favorite parts of the day
• His fingerprint on the ride — expanding gravel routes across the whole week, and the story behind taking RAGBRAI across the border into Minnesota for the first time, including the logistics nightmare (and reward) of coordinating two states' worth of troopers, ambulances, and vendors
• Celebrities, politicians, and the "20,000 celebrities" line — how RAGBRAI handles VIP requests without turning into a political event, and why guests from David Robinson to Patrick Dempsey have quietly blended in with the pack
• The evolution of RAGBRAI's culture — from the harder-partying "Animal House" years of the '80s and '90s to today's more family-friendly ride, and how Matt's approach has changed the relationship between riders, law enforcement, and host towns
• Rig-of-the-week stories — from decrepit yellow school buses to six-figure RVs towing Jeeps towing side-by-sides, and the time a support-crew wife got an RV "high-sided" on the bike route and raced the tow truck to fix it before her husband rolled through

Grab your helmet, fill your water bottles, and — if you're in spandex — know that this is a judgment-free zone. It's RAGBRAI, straight from the ringmaster himself.

#Ragbrai #Ragbrai2026 #Bicycle #BikeTour

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Gen X dads are the generation that found themselves standing right in the middle of two very different worlds. They were raised by Boomer dads who could fix almost anything, who kept a coffee can full of random screws and bolts in the garage, read paper maps, and wrote down their own directions before a family vacation. These were the dads who believed a little trial and error, a toolbox, and a stubborn refusal to ask for help could solve most problems. Gen X absorbed those lessons — learning how to change a tire, build things, troubleshoot problems, and figure things out because there wasn’t always a YouTube video or an app to do it for them.

But when Gen X became dads, they were handed a very different parenting playbook. They grew up with independence and “go outside until the streetlights come on,” yet they were expected to raise kids in a world of constant connection, safety concerns, and technology. Their Gen Z kids might use turn-by-turn GPS instead of reading a map, search a tutorial instead of digging through a toolbox, and replace something rather than repair it. Gen X dads became the bridge between generations — teaching their kids how to navigate a world that they themselves were still learning to navigate, while quietly wondering how they went from being the latchkey kids of the 80s to the parents trying to set screen-time limits in the digital age.

#fathersday #dads #genx #boomer #genz

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For most fans, Jan Jensen is known as one of the most accomplished figures in women's basketball history—a six-on-six scoring sensation from Kimballton, Iowa, an NCAA scoring champion at Drake, a professional player in Europe, and now the head coach of the Iowa Hawkeyes. But in our latest podcast episode, we go beyond the résumé and the record books to explore the person behind the success. Jan shares stories from her remarkable journey, reflects on the mentors and relationships that shaped her career, and offers insight into the partnership with Lisa Bluder that helped elevate Iowa women's basketball into a national powerhouse.

What makes this conversation special is that it reveals the authentic, down-to-earth personality that has made Jan so beloved throughout Iowa. She talks about leadership, gratitude, family, and what it means to represent the Tigerhawk every day. Whether she's posing for a selfie at Target or connecting with fans across the state, Jan never loses sight of the privilege that comes with wearing Iowa across her chest. It's a candid, heartfelt conversation filled with humor, perspective, and the kind of wisdom that extends far beyond basketball. Hawkeye fans, sports fans, and anyone who appreciates great people with great stories won't want to miss this episode.

#Hawkeyes #Jan #Jensen #JanJensen #CollegeWomensBasketball #DiveBar #Iowa #Hawkeye

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This week Brad shares a compelling story about a project he took on a bit outside his comfort zone: building a vintage bicycle from the frame up despite openly admitting he is “the farthest thing from mechanical.”

We talk about concession stand food programs, and we enjoy Irish Whiskey poured out of a golden ostrich head.

#Shankyswhip #cutwater

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Hey all you Deep Divers, we are trying a different format this week to see how it sounds. We’re thinking about calling these Playlist Shows, where we take a topic, pair it with some music that’s important to us, and then discuss why the two are connected in our memory.

But here’s the cool part. If you are a member of our Facebook Group “ Deep Dive Podcast “ you can contribute your song in the comment section, and we’ll add it to our Shared Spotify Playlist.

So this week’s Playlist theme is “Summer Songs “ now you’re going to hear a bunch of Gen X summer songs in today’s show, but YOUR contributed song doesn’t have to be from the 70’s, 80’s, or 90’s, we just want to hear what song reminds YOU of summer.

So without further adue, here is this week’s Playlist show “Summer Songs”………….

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A fan requested we pick Gen X related topics out of a bowl and discuss off the top of our heads to see just how smart we are........ the answer turned out to be what you would expect....... not very.

The guys kick things off with sardines straight from a Lisbon tin fish restaurant before diving headfirst into the nostalgia that defined growing up Gen X in the Midwest. From a rave review of a recent guest episode that had listeners buzzing, to a spirited Kentucky Derby detour, the conversation never stays still for long.

The heart of the episode is a "mystery basket" of topics written by John's wife. Newspapers, fast food, drive-in theaters, school lunches, and school buses all get their moment, with the kind of specific, laugh-out-loud detail that only people who actually lived it can deliver. Did you know cinnamon rolls with chili is an Iowa thing? Or that Hardee's beat McDonald's to the promotional glassware game?

In the final stretch, we turn the conversation to summer pool days and the music that soundtracked them. Bob Seger, ZZ Top, Fleetwood Mac, the Beach Boys — the songs start flowing and suddenly you're 16 again, windows down, heading to the reservoir without a care in the world. This episode is part history lesson, part therapy session, and entirely the kind of conversation you didn't know you needed. Hit play — you won't regret it.

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In this episode, we sit down with acclaimed blues musician Kevin Burt, a performer whose powerful voice and authentic storytelling have earned him recognition across the United States and beyond. A true road warrior, Kevin performs hundreds of shows each year, captivating audiences with a soulful sound that has drawn comparisons to legendary artists such as Bill Withers and Aaron Neville. Throughout his career, he has accumulated numerous awards, festival honors, and a devoted following while performing both as a solo artist and with his band, The Instigators.

We explore Kevin's remarkable journey from Iowa stages to international acclaim, including his induction into the Iowa Blues Hall of Fame and his unforgettable success at the International Blues Challenge in Memphis, where he captured the competition's highest honor as Best Solo Blues Artist. Along the way, Kevin shares stories from life on the road, the passion that fuels his music, and the experiences that have shaped one of the most respected voices in modern blues. Whether you're a longtime blues fan or discovering his music for the first time, this conversation offers an inspiring look at the artistry, perseverance, and heart behind Kevin Burt's extraordinary career.

#InternationalBluesChallenge #Blues #KevinBurt #IowaBluesHallofFame #Iowa #Blues #HallofFame

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