Smart Money Happy Hour with Rachel Cruze and George Kamel

Episode: Questioning “Life” Choices With Ken Coleman (“Would You Rather” Edition)
Date: February 5, 2026
Network: Ramsey Network
Guests: Ken Coleman
Main Theme:
The episode blends playful “Would You Rather” games with deeper conversations around money, career, contentment, and life choices. Hosts Rachel Cruze and George Kamel, joined by Ken Coleman, share personal stories, debate hypothetical scenarios, and tackle the real “game of life” decisions listeners face.

Episode Overview

This episode brings in Ramsey personality Ken Coleman for a lively happy hour. The trio goes “unfiltered” with a round of “Would You Rather” questions, pop culture banter, and insights into making smart choices about career, money, and life purpose. They swap stories, challenge each other's “life” decisions, and probe what really matters when chasing success and fulfillment.

Key Discussion Points & Insights

Meet Ken Coleman and the “Work Space” (01:19-02:30)

• Ken describes his role at Ramsey: “I want to help people win at work, get better personally so they can move up professionally... helping people win at work as part of the Ramsey crew is the role.” (01:28)
• The group jokes about contact lenses, vision woes, and personal quirks, setting a laid-back, humorous tone.

Money and Identity: Eyewear, Glasses Trauma, and Self-Image (02:31-05:54)

• The hosts discuss their vision issues and the emotional impact of eyewear growing up.
• Rachel shares: “I was secretly bullied, yes. Behind her back and never again.” (04:59)
• Ken admits to basketball mishaps with glasses: “Finally I learned how to stick my finger in my eye, which is...” (05:11)
• They banter about coping with contacts—“saliva does work”—and why some avoid eye surgery.

“Would You Rather” Lightning Round (06:08-10:18)

• Croc Shoes vs. Destroyed Loafers: Ken, hating Crocs, would still wear them over losing prized shoes: “I would eliminate them from society if I had the power. However, I would rather be subjected to that humiliation than watch a dog eat a perfectly great pair.” (06:29)
• Costco Ban vs. Missed Hair Appointments: George would rather skip Costco for Sam’s Club: “I could go Sam's Club for a year and live to tell the tale.” (07:41) and laments the importance of hair care.
• Moon Landing vs. Amazon Prime: Rachel would (if forced) publicly state the moon landing happened to keep Amazon Prime, despite her conspiracy leanings. Ken admits he's “60/40 that we didn't.” (10:46) They riff on government distrust and pop culture.

The “Game of Life” Scenarios – Major Life Choices (12:50-18:12)

1. College vs. Career Early Start (12:50-16:39)

• Ken chooses the work path unless a degree is mandatory: “Experience long term is gonna make you more money... four-year head start... I mature a little bit faster and better.” (13:09)
• Rachel values the growth and structure college offers: “18 to 21... you grow up so much... you're getting educated.” (15:08)
• George suggests travel as a third option: “Go to Europe...you'll be way more cultured big time than going to college.” (16:07)

2. Taking A Promotion in a Disliked City (16:42-21:02)

• Ken prioritizes financial goals: “Do what you have to do so you can do what you want to do.” (16:56)
• Stage of life matters—single and young, more likely to move; with family, more complexity.
• They joke about least favorite cities: Milwaukee, Detroit, West Texas, and Des Moines, with playful ribbing about climate and lifestyle.

3. Dream Job with Pay Cut? (23:13-28:33)

• Ken's advice: Only take a lower-paying dream job if you can sustainably adjust your lifestyle: “If you can adjust your lifestyle, we've proven you can be an everyday millionaire making that.” (24:00)
• On meaning, trade-offs, and fulfillment: “I've sat across the table with New York executives who are...absolutely miserable.” (25:58)
• Rachel shares the “Spanish fisherman” parable: “There’s something about the meaning of life with relationships, your contribution to the world...big things that bring satisfaction.” (27:30)
• Ken’s reflective question: “What do you want your day to look like?” (28:00)

Money Scenarios & Practical Advice (32:27-41:12)

Fix Car or Foundation with Bonus? (32:27-33:43)

• “You gotta fix the foundation...I feel like a schmuck if I go get a better car.” –Ken (32:52)

Laid Off—Retail Side Hustle or Freelance? (34:40-37:19)

• Ken: Use skills for the best return, don’t shrink to convenience jobs by default. “The best bang for your buck with your time is where I've got a transferable skill.” (36:08)

Inheritance Decision (37:19-41:46)

• Ramsey Steps: Pay off debt, fully fund emergency fund, then celebrate/make memories with any excess.
• Ken: “We’re gonna take a trip...I’m gonna call all the kids...make a memory.” (38:32)
• George would save, give, and possibly buy a guitar and Disney trip; Rachel reveals her rare splurge on a Dyson hair dryer (42:02), which prompts comic relief.

Breadwinner or Stay-at-Home? (44:40-47:08)

• Ken and George prefer being breadwinners for the pressure and need “to get out of the house.”
• Rachel would, in her current season, stay home to enjoy school volunteering and family life.

Four-Day Workweek or Double Salary/Longer Hours? (48:21-49:54)

• Quality of life vs. fast-tracking financial goals is debated.
• Rachel envisions a “perfect Friday”: workout, sauna, documentary, bougie lunch with friends, then family time.
• George enjoys solo errands, especially at grocery stores: “Very peaceful, therapeutic.” (49:46)

Notable Quotes & Memorable Moments

• “I would eliminate [Crocs] from society if I had the power. However, I would rather be subjected to that humiliation than watch a dog eat a perfectly great pair.” –Ken (06:29)
• “Experience long term is gonna make you more money...I think that I move up the ladder faster. So I’m always going to be the efficiency guy.” –Ken (13:09)
• “If you can adjust your lifestyle, we’ve proven you can be an everyday millionaire making that.” –Ken (24:00)
• “There’s something about the meaning of life with relationships, your contribution to the world…those are the things that bring satisfaction.” –Rachel (27:30)
• “What do you want your day to look like?... I think by about day 10, 11, 12, you start to really drill down on what do I want a day to look like—and it’s a lot cheaper than you think.” –Ken (28:00)
• “I'm proud of the fact that I don't use a hairdryer. This is au natural.” –Ken (43:12)
• “I love a good handshake though. I'm a handshaker.” –Rachel (58:20)
• “They lead with emotion, not long term vision.” –Ken, on the #1 money mistake (52:56)
• “You aren't stuck. You're unclear. If you can get some clarity, you wouldn't believe how quickly you'll be able to make a decision.” –Ken, on feeling stuck in life (53:12)

Timestamps for Important Segments

• 01:19 – Ken Coleman’s introduction and role at Ramsey
• 04:59 – Rachel shares glasses/college bullying story
• 06:08 – "Would You Rather" round begins
• 10:46 – Moon landing conspiracy debate
• 12:50 – Game of Life: College vs. Career path
• 16:42 – Take the big-pay promotion in a city you dislike?
• 23:34 – Dream job with a pay cut scenario
• 27:30 – Fisherman parable and what matters in life
• 28:00 – “What do you want your day to look like?”
• 32:27 – Big expense: car or foundation?
• 34:40 – Laid-off: retail or freelance?
• 37:19 – Inheritance: spend, save, or invest?
• 44:40 – Breadwinner or stay-at-home partner?
• 48:21 – Four-day workweek vs. double pay with weekends
• 52:56 – Rapid Fire: Biggest Money Mistake
• 58:20 – Handshake judgments

Episode Tone & Style

The episode is energetic, unfiltered, and full of friendly ribbing. Ken’s earnest career advice blends seamlessly with the duo’s humor, pop culture references, and personal stories. The tone is conversational, candid, and often self-deprecating, striking a balance between wisdom and fun.

Final Takeaways

• Do what you have to do now so you can do what you want to do later (16:56)
• Trade-offs between money and meaning are personal—and it's okay to adjust your life down for the right reasons.
• Focus on relationships and experiences over material gain: “It's a lot cheaper than you think to have a full, rich life.” (28:00)
• Clarity, not just grinding harder, leads to better career and life decisions.
• Don’t be afraid to embrace hard things: “The hardship is the way...the magic.” (31:42)
• And finally—a good handshake still matters. (58:20)