You Betcha Radio #343: "If We Won The Lottery"
Date: September 10, 2025
Host: Myles "You Betcha Guy"
Guests: Ryan, Tyler, Jared
Episode Overview
This week, the You Betcha gang leans hard into comedy and classic Midwest camaraderie as they riff on vehicle mishaps, karma in the garage, secret marriage leverage, and—finally—the juicy topic: What would they do if they won the lottery? The guys keep the laughs rolling while sharing relatable stories about aging, financial fantasizing, and the importance of stretching after 30.
Key Discussion Points & Insights
1. Myles’ Big Confession: Truck vs. Warehouse Pole
[00:00 - 16:00]
- Myles opens up about a mishap: He rammed his truck into a warehouse pole, incurring $13,000 in damage.
- Ryan draws the connection to his own past light pole incident, teasing that karma got Myles for roasting him earlier.
- Tyler & Jared pile on with jokes about the “double whammy” of hitting your own pole in your own building.
- The details of the accident:
- Myles wasn't on his phone; he just spaced out, going 5 mph, and hit the pole “almost dead center.”
- The impact caused pop to spill all over the dash but no airbags deployed.
- Damage includes a bent hood, malfunctioning adaptive cruise, and a jammed panel.
- Insurance and aftermath:
- $13,000 damage; Myles starts the insurance process.
- “When I was talking to insurance, they're like, so you hit the pole inside. Okay. Do you—it's your building. Yes, Yes. I did this to my own building. Pretty dumb.” – Myles [15:24]
- Themes: Embarrassment, the comedy of karma, and the importance of not going in too hard on friends’ mistakes.
2. Midwest Marriage: Secrets, Leverage, and Payback
[6:00 - 15:00; 29:52 - 31:14]
- Myles describes “marriage leverage”:
- Just as he lost leverage after hitting the pole (and previously ribbing his wife Anne for backing into a garage door).
- Anne promptly tells their friends about Myles’ crash, instead of keeping it private.
- “Marriage is about two things: keeping score and having leverage over the other person. And I lost some leverage that day, big time.” – Myles [30:00]
- Anecdotes about payback and keeping secrets illustrate the fun but competitive dynamic among spouses and friends.
3. Accidental Injuries & Getting Old
[56:55 - 70:29]
- One-upping stories:
- Sneezing in the shower and hurting your back (Tyler).
- Clipping fingernails and getting neck pain (Ryan).
- Kitchen/fridge injuries and general “fringery.”
- “I just got a kitchen injury, I got a fridge injury, a fringery injury, and a fringery.” – Myles [59:00]
- On aging in your 30s:
- “Ever since I turned 30 years old, I just—I wake up with something that doesn’t feel good.” – Myles [57:13]
- They joke about requiring shower chairs, multivitamins, and even HGH to survive their 30s.
- Resigned self-deprecation:
- Swapping dad-shoe advice, talking about taking baby aspirin, and fear of losing mobility with age.
4. What Would You Do if You Won the Powerball?
[31:21 - 54:03]
- Lottery-pocalypse:
- Powerball hits $1.8 billion.
- Wild speculation about losing a winning ticket or “Charlie Berens accidentally throwing it away, thinking it was a receipt.” [31:46]
- Segues to a tangent about a guy who lost a hard drive full of Bitcoin.
- Bitcoin & Hard Drives:
- “That’s like my number one rule about life is just don’t throw a hard drive.” – Myles [35:39]
- Spending the Winnings: Personal Philosophies
- Tyler’s approach:
- Go stealth: Don’t tell anyone, not even the guys.
- Try to preserve normalcy and avoid the curse of lottery winners.
- “I'm trying to stay as anonymous as I possibly can be. I'm not telling you guys. I'm not telling...” [39:59]
- He’d pay for family’s education, buy land, and set up conditions so future generations have to work to get the money (“they have to earn it”).
- Myles would go public, dump it in the S&P 500, start a content series titled “Day in the Life of a $900 Million Guy,” and buy his own private golf course:
- “I think I immediately run to Oh, You Betcha Instagram, Facebook, YouTube, whatever. And I just announce that I have won the lottery.” [43:07]
- “If you invested $900 million and you had a 5% return year over year... you're making $45 million without doing anything.” [45:11]
- Ryan’s plan:
- Lawyers, wealth managers, and “as much cash as I can fit in my pocket.”
- Would buy or build a compound, hunting ranch, or golf course, and casually pay off all family debts.
- “First place, my pocket. How much do you think I can fit in my pocket? Like a hundred thousand?” [47:40]
- Might keep coming to work for a while, if only to keep a routine.
- Jared:
- Steak dinner at Longhorn, then call into Dave Ramsey to troll him, then (joking) donate the rest to PETA. [54:50]
- Tyler’s approach:
- Themes: The guys debate the importance of routine, whether it’s possible to “go broke,” and fear the lottery curse.
- Notable Quote:
- “More money, more problems.” – Tyler [52:45]
- “I would be the guy to help [my buddies] out of bad situations, like if they lose their house, bail them out of that.” – Tyler [51:42]
5. Would You Buy Into Your Sports Team?
[53:08 - 54:28]
- Why Tyler wouldn’t buy the Vikings:
- “Because then one of my favorite things in the world becomes my job.” [53:49]
- Smartest play:
- Minority stake in a team like the Packers, so you get perks but no responsibility.
6. Historic & Modern Lotteries
[74:06 - 75:15]
- Jared’s Fun Fact:
- First recorded lottery was in China, Han dynasty (205–187 BC), used to fund the Great Wall, played via “Keno slips.”
- Winners got prizes, goods, sometimes delivered by carrier pigeon (“the White Pigeon game”).
7. Fan Questions: Silly Scenarios
[76:06 - 80:39]
- “Would you rather walk into a spider web or get chased by a goose?”
- All pick spider web, since geese are “no joke.”
- “How do you eat spaghetti when no one’s watching?”
- Unanimous: Messily. “Eat spaghetti like no one’s watching.” – Jared [80:39]
- Banana-eating habits
- Turns into a round of goofy revelations (“I just shove the whole thing down”).
8. Classic Midwest, Light Roast & Business as Usual
- Throughout, the guys keep the signature You Betcha humor flowing—whether discussing duct-taped bumpers, foam rental cars, or “zip-tie repairs.”
- Regular “roasts” and callbacks to ongoing inside jokes (like Ryan’s wrist injury, or Anne’s driving).
- No topic is too trivial—kitchen injuries, blinker malfunctions, golf cart mishaps—all ground for laughs.
Memorable Quotes
- “Marriage is about two things: keeping score and having leverage over the other person. And I lost some leverage that day, big time.”—Myles [30:00]
- “That’s like my number one rule about life is just don’t throw a hard drive.”—Myles [35:39]
- “More money, more problems.”—Tyler [52:45]
- “Eat spaghetti like no one’s watching.”—Jared [80:39]
Notable & Humorous Moments (with Timestamps)
- Myles’ confession & $13,000 warehouse accident [00:48–04:44]
- Ryan’s foot nearly run over by Anne’s golf cart [07:31]
- Total car damage and insurance hassles [09:17–10:12]
- “Marriage leverage” and marital tell-alls [29:52–31:14]
- Powerball deliberations and secret plans [39:59–43:07]
- Golf course dreams & ROI breakdown [45:11]
- Aging body complaints: sneezing injuries and “fringeries” [56:55–60:00]
- Historic lottery fact: Keno slips and the Han dynasty [74:06]
- Fan Q&A: Goose chase vs spider web [76:21]
- Banana-eating shame stories [80:42]
Summary
Episode #343 trades small-town “guy talk” for big lotto dreams, all anchored by the hilarious honesty and banter fans love. Whether musing on midlife aches, marriage jokes, surprise calamities, or financial what-ifs, Myles, Ryan, Tyler, and Jared build a fun, relatable listen that’s as Midwest as a DQ drive-thru.
Bottom Line:
If you’ve ever daydreamed about hitting it big, endured a dumb mistake, or simply needed a laugh about getting old, this episode delivers—you betcha.