Money Rehab with Nicole Lapin

Episode: From Losing Dream Jobs to Booking First-Class Flights: Reinventing Success with Daryn Kagan and The Miles Husband
Date: November 24, 2025
Host: Nicole Lapin, Money News Network
Guests: Daryn Kagan (former CNN anchor, journalist, and entrepreneur), Trent Swanson a.k.a. "Miles Husband" (travel-hacking expert)
Producer/Co-Host: Morgan Lavoy

Episode Overview

This episode is a two-part deep dive into personal and financial reinvention. Host Nicole Lapin and producer Morgan Lavoy first welcome groundbreaking journalist Daryn Kagan, who shares her journey from leading anchor at CNN to redefining success on her own terms after an unexpected layoff. In the second half, Daryn’s husband, Trent (“Miles Husband”), details how the couple maximized their money and unlocked luxury global travel by mastering the credit card points game. The team shares candid wisdom on careers, resilience, relationships, and tactical money moves.

Key Discussion Points & Insights

1. Shattering the Taboo Around Money and Personal Reinvention

• Nicole Lapin opens the episode by reframing money talk as essential:
  “Ever notice that we will talk about everything before we talk about money? ... But not for long!”
• The team positions financial resilience and openness as transformative.

2. Daryn Kagan: From Dream Job to Uncharted Paths

The Journalism Ladder & Dream-Chasing

• Daryn’s rise:
  • Started in local news (Phoenix, making $19,000/year).
  • Gradually moved to CNN, eventually making over $500,000/year.

“KNBC, Los Angeles was my ultimate dream.”
— Daryn Kagan (08:13)

Sudden Loss and Reality of Layoffs

• Unexpected non-renewal:
  • Daryn’s contract at CNN wasn't renewed after 12 years.

“He said, ‘Your contract is up the end of this year, and I want to let you know we’re not going to renew you...’ Instead, he called me up and he said, ‘I want to let you know we're not going to renew you.’”
— Daryn Kagan (11:20)

• Maturity in the face of loss:
  • Daryn did not ask "why," accepting that in media, reasons are often irrelevant or never revealed.

“Everything ends. ... The why it ends eventually doesn’t matter. ... That’s not dark ... it’s light.”
— Daryn Kagan (14:06)

Age, Gender, and Career “Expiration”

• Discusses the implicit shelf-life for women in TV news—especially non-star anchors in their forties.
• Recognizes industry progress but maintains realism (“it kind of is what it is”).

Reinventing on Her Own Terms—Entrepreneurial Leap

• Launched own positive-news website: Spent months building and self-funding the venture after CNN.
• “Choosing herself”: Declined moves to different cities and lower-pay local jobs, instead building a platform for uplifting news, ahead of CNN’s “Heroes”-era.

“So instead I made up the job and I gave it to myself, which is really how I’ve had the most success over my entire career, anyway.”
— Daryn Kagan (18:26)

The Role of Financial Preparation

• Financial advisor’s impact:
  • Daryn credits her advisor, Margaret, with empowering her to save 2/3 of her CNN salary.
  • Having strong savings made the forced transition empowering, not panic-inducing.

“I created that [cushion]. That was very empowering.”
— Daryn Kagan (26:33)

On Singlehood, Relationships, and Life's Surprises

• Reflects on her earlier fears of being “broke, alone, and homeless” after a job and relationship both ended, yet found fulfillment in unexpected ways.
• Later found love, family, and a blended life.

“What you want is not coming. What’s coming is better than you could ever dream for yourself.”
— Daryn Kagan (40:00)

3. Trent "Miles Husband" Swanson: Travel, Points, and Financial Hacking

The Miles Game—Origin Story (46:54)

• Trent read an article about earning flights via specific purchase methods (“buy a pair of shoes...get two free first-class tickets.”)
  • Tried it, succeeded, and scaled up the system.

“Are these techniques scalable ... where I can ... make this thing phenomenal?”
— Trent Swanson (45:54)

Strategic Earning and Burning of Points

• Key principle: Begin with the end in mind
  • Define: Where, Class, How Many, Flexible Dates
  • Reverse-engineer the points strategy to fit the travel dream.

“What’s more important ... is you really work on your vision … Answer those four questions.”
— Trent Swanson (50:03)

• Loyalty program mechanics: Knowledge of each airline’s inventory-release cycles is essential for successful redemptions.
• Dynamic techniques: E.g., Capital One’s 30% transfer bonus to JAL—a real-time, high-value hack.

Notable Anecdotes

• Wild dedication:
  • Did “mattress runs” (checking into hotels for elite status, not to sleep—on their wedding day!).
• Scorecard:
  • Japan first class for $5.60 each via strategic points, transferred at the right time.

Debunking “Points Hoarding” & Loyalty Chasing

• Warns against amassing points without a plan (“Don’t collect blindly!”).
• Advises against chasing airline status for most travelers and urges using points efficiently before devaluations.

“Most people who want to travel coach ... should probably just get a 2% cash back card.”
— Trent Swanson (51:24)

• Corporate incentives and pitfalls: Some credit card/points advice in the ecosystem is influenced by referral bonuses.

Strategic Tips for Listeners

• Start with a specific travel goal, not with generic points strategy.
• Credit cards:
  • Biggest accelerators, but only if you pay off in full. Self-discipline is mandatory.
  • Check your credit health via Equifax, Experian, TransUnion before applying for new cards.

“Self discipline is super important ... it’s too expensive to screw up. So credit is really important...treat it as an asset.”
— Trent Swanson (65:57)

Notable Quotes & Memorable Moments

[07:09] Daryn on supporting women in journalism:

“Be really good at your job and be nice to other people because ... that person you’re being good to might one day just be a badass boss woman who you’re thrilled to be on her podcast.”

[14:06] On endings:

“Everything ends ... And the kind of the why it ends eventually doesn’t matter. ... I actually think it’s light because then you appreciate what you have while you have it.”

[26:09] On lifestyle creep:

“I mean, you’re the opposite of lifestyle creep.”
— Morgan Lavoy
“Yes, the opposite.”
— Daryn Kagan

[40:00] Daryn on the journey to love and family:

“What you want is not coming. What’s coming is better than you could ever dream for yourself.”

[48:22] Trent on travel hacking success:

“...The same techniques ... can get you butlers and showers in the sky and Krug champagne ... That’s where the scale makes the time investment really, really pay off.”

Timestamps for Key Segments

• (04:20 - 05:58): Episode & guest overview; themes of loss and reinvention
• (06:04 - 19:10): Daryn Kagan’s journalism career, loss of “dream job,” and the reality behind the news business
• (19:10 - 26:33): Contract stories, age/gender in media, and career pivots
• (26:33 - 33:13): Financial advisor Margaret; saving big, being ready for change
• (33:13 - 41:10): Singlehood, heartbreak, letting go of expectations, family-building
• (41:10 - 46:10): Daryn and Trent’s relationship dynamics and meeting story
• (46:10 - 57:54): “Miles Husband” segment—origin, strategies for travel hacking
• (57:54 - 61:00): Loyalty program mechanics, award inventory timing, best practices
• (61:00 - 66:00): Points hoarding, status chasing, and wrap-up travel/money advice

Straight-to-the-Bank Takeaways

• Invest in financial literacy and mentorship early.
• Live below your means, leverage windfalls for future freedom.
• Career setbacks are often set-ups for reinvention—don’t cling to the “why.”
• When using miles/points:
  • Start with your travel vision, not with “points for the sake of points.”
  • Use credit cards only if you’re disciplined; always check your credit first!
  • Learn airline award inventory release rules—timing is everything.
  • Don’t hoard points or chase status you’ll never use.
• Big life dreams (career or family) can arrive on their own timeline—letting go may be the real unlock.

Additional Resources

• darynkagan.com: Daryn’s positive news site
• mileshusband.com: Trent’s travel hacking resources

For anyone negotiating life’s left turns, transitions, or plotting next-level travel, this episode brings encouragement, practical strategy, and real talk about thriving through reinvention.