From Losing Dream Jobs to Booking First-Class Flights: Reinventing Success with Daryn Kagan and The Miles Husband

Summary

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

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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.

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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.

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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)

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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)

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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.”

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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

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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.

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Additional Resources

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

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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.

Transcript

[Nicole Lapin]

Here's one piece of advice that I've given for years. Build an emergency fund. Aim to stash away enough to cover at least three months of expenses in case your income suddenly drops. Sounds simple, right? But let's be honest, it's not. Saving even one month's worth of living costs can feel impossible. Just when you're making progress, that check engine light blinks on and derails your plans. Life already throws enough curveballs you don't need your bank adding to the chaos. That's why it's so important to choose one that makes savings easy and doesn't nibble away at your hard earned money with ridiculous fees. Chime understands that every dollar counts. That's why when you set up direct deposit through Chime, you get access to fee free features like free overdraft coverage, getting paid up to two days early with direct deposit, and more with qualifying direct deposits. You're eligible for free overdraft up to $200 on debit card purchases and cash withdrawals. To date, Chime has spotted members over $30 billion. Work on your financial goals through Chime today. Open an account in just two [e-mail] MNN that's chime.com MNN Chime feels like progress.

[Chime Representative]

Chime is a financial technology company, not a bank. Banking services and debit card provided by the Bancor Bank NA or Stride Bank NA members FDIC Spot me Eligibility requirements and overdraft limits apply. Timing depends on submission of payment file Fees apply at out of network ATMs, bank ranking and number of ATMs according to U.S. news and World Report 2023 Chime checking account required I live in.

[Nicole Lapin]

LA now, but lately I have been craving the seasons, snow, hot cocoa, the whole thing. I don't even ski, but I have been daydreaming about working remotely from somewhere really cozy on the east coast like a cute little ski town for a little bit and whenever I know I'm going to be gone for a while myself, that my home can actually be working for me while I'm away. Because I host my space on Airbnb, it is one of the easiest ways to earn passive income from something you already have. And that extra income feels particularly helpful this time of year as we approach the holidays. A lot of my friends say that sounds amazing, but where do you find the time to manage guests and bookings? And that's when I tell them about Airbnb's co host network. Through Airbnb you can find a local co host who can help you set up your listing, handle reservations, communicate with guests, provide on site support, even help with design and styling. I like to give a personal touch when I'm hosting on Airbnb, so I make a list of my favorite restaurants in the area and I hand write a note welcoming my guests to the property. My guests love it, but I also know that some of those little personal touches can take a lot of extra time.

[Morgan Lavoy]

So this is the exact kind of.

[Nicole Lapin]

Thing that you would want your co host to help you with. Whether you're traveling for work or chasing the snow or escaping it, or you've got a second place that just sits there empty more often than you'd like, your home doesn't have to just sit there. You can make extra money from it without taking on extra work. Find a co [e-mail] host here's one piece of advice that I've given for years. Build an emergency fund. Aim to stash away enough to cover at least three months of expenses in case your income suddenly drops. Sounds simple, right? But let's be honest, it's not. Saving even one month's worth of living costs can feel impossible. Just when you're making progress, that check engine light blinks on and derails your pipe plans. Life already throws enough curveballs you don't need your bank adding to the chaos. That's why it's so important to choose one that makes savings easy and doesn't nibble away at your hard earned money with ridiculous fees. Chime understands that every dollar counts. That's why when you set up direct deposit through Chime, you get access to fee free features like free overdraft coverage, getting paid up to two days early with direct deposit and more with qualifying direct deposits. You're eligible for free overdraft up to $200 on debit card purchases and cash withdra. To date, Chime has spotted members over $30 billion. Work on your financial goals through Chime today. Open an account in just two [e-mail] MNN that's chime.com MNN Chime feels like progress.

[Chime Representative]

Chime is a financial technology company, not a bank. Banking services and debit card provided by the Bancorp Bank NA or Stride Bank NA members. FDIC Spot me Eligibility requirements and overdraft limits apply. Timing depends on submission of payment file. Fees apply at out of network ATMs. Bank ranking and number of ATMs according to US News and World Report 2023 time checking account required I'm Nicole Lapin.

[Nicole Lapin]

The only financial expert you don't need a D stand.

[Chime Representative]

It's time for some money.

[Darren Kagan]

Rehab.

[Morgan Lavoy]

Today's episode is a double header with a power couple I know you're gonna love.

[Nicole Lapin]

In the first part of the conversation.

[Morgan Lavoy]

I'm talking to the one, the only, Darren Kagan. And let me tell you, if teenage.

[Nicole Lapin]

Nicole had a vision board, this woman's.

[Morgan Lavoy]

Face would have been front and center.

[Nicole Lapin]

Before the world of social media and.

[Morgan Lavoy]

Influencers, Darren was a trailblazing journalist covering.

[Nicole Lapin]

Some of the biggest stories of our time. From the Gulf War to 9 11. As a lead anchor at CNN, I.

[Morgan Lavoy]

Never, ever even dreamed that our worlds would intersect.

[Nicole Lapin]

But they did, and we tell that story today. Darren was not only working my dream.

[Morgan Lavoy]

Job at cnn, it was her dream job, too.

[Nicole Lapin]

But as you'll hear in this episode, even dream jobs can come to an end.

[Morgan Lavoy]

Darren opens up about how she found out her contract at CNN wasn't renewing and the questions that she will never.

[Nicole Lapin]

Have the answers to. She told me what came next and how she redefined success on her own terms. If you have ever felt like your career took a left turn that you.

[Morgan Lavoy]

Did not see coming, this conversation is.

[Nicole Lapin]

One you need to hear.

[Morgan Lavoy]

After the break, you'll hear from Darren's husband, Trent Swanson, AKA Miles. Husband.

[Nicole Lapin]

What started out as a small experiment.

[Morgan Lavoy]

To earn two free flights to Miami turned into jet setting across the globe.

[Nicole Lapin]

First class.

[Morgan Lavoy]

Yes, I have seen the receipts. Emirates, Japan, champagne in the sky.

[Nicole Lapin]

All for literally $5.

[Morgan Lavoy]

Trent breaks down exactly how they hacked the travel points game.

[Nicole Lapin]

And they even helped my executive producer.

[Morgan Lavoy]

Morgan plan her honeymoon to Japan. So from losing your dream job to.

[Nicole Lapin]

Living your dream life, this episode is.

[Morgan Lavoy]

Full of hard earned wisdom, inspiration, and.

[Nicole Lapin]

Some seriously game changing money tips.

[Morgan Lavoy]

Darren Kagan, welcome to money rehab.

[Darren Kagan]

I cannot believe we're here. I'm so happy we're here.

[Morgan Lavoy]

If I had a poster of you growing up, it would have been next to Christy Yamaguchi as like, my idols. Truly.

[Darren Kagan]

I mean, that's beyond, beyond, beyond, beyond.

[Morgan Lavoy]

And some say, don't meet your idols. Chris Yamaguchi taught me how to ice skate, actually. And you taught me how to be a good person.

[Darren Kagan]

And in the live order, ice skating, far more important, truly.

[Morgan Lavoy]

You know, growing up, all I heard was like, Darren Kagan, Darren Kagan, Darren Kagan. Like, one day maybe you could meet her or smell her hair or like, be in her presence because she's the one that made it out of the journalism class that both of us were in same high school.

[Darren Kagan]

For the record, I believe I graduated before you were born. However, we did not only share the high school. There's one legendary journalism teacher who taught there forever. Mr. Chesterton, may he rest in peace. Yes. Mr. C. Who launched some significant careers and just significant people. It was a great place to put your time.

[Morgan Lavoy]

It was so interesting because in high school, like, you don't know what you're good at. There's so much teenage angst. And I stumbled into something that I knew nothing about and never thought, like, I would want to be a journalist growing up. And it truly changed my life.

[Nicole Lapin]

And.

[Morgan Lavoy]

And that man, I mean, imparted, like, so much Darren Kagan fandom, like, I can't tell you, is indoctrinated into me just being, like, one day you could make it big and you could do this, too. And so I never thought that I would actually meet you, much less know you.

[Darren Kagan]

But we should also say the reason we did meet was because at an incredibly young age, for this kind of career you land at cnn, which took me quite a few more stops to get to.

[Morgan Lavoy]

Yes. Back in the day in journalism, you were supposed to go through these small markets, and I thought, like, I would live and die in Poughkeepsie, and maybe one day I would get to Los Angeles and local news, and then I would die a happy woman.

[Darren Kagan]

Knbc, Los Angeles was my ultimate dream.

[Morgan Lavoy]

But then you were out crushing it, covering 9 11, covering the Gulf War, like, all the things at CNN, like the queen that you are. And, yeah, I thought that, you know, maybe one day, like, I would meet you somewhere. And I did not expect at 20 to get called for this thing, this Internet thing at cnn. And I truly, truly. We were talking about it this morning as we were thinking about you guys coming in. I thought I would audition there, and it would be such a great experience.

[Darren Kagan]

As it would have been, and I.

[Morgan Lavoy]

Would leave and I would never, ever forget. And on the off chance, I emailed you and I thought maybe. I don't know, like, maybe she would write me back. But you did. And it. And it was. It's something that I'll never forget. And you invited me to sit with you on the anchor desk, and here we are.

[Darren Kagan]

And I'm so proud of everything that you've done. And, yeah, I mean, that's just what you do. You be good and you be nice. That's what I always tell people. Be really good at your job and be nice to other people because. Well, just because. But also, 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.

[Morgan Lavoy]

But, you know, in that space, too oftentimes, like, women are pitted against each other that there's some competition. And you bucked that trend for me.

[Darren Kagan]

Thank you for that credit. I would also say I felt like at cnn, that really was not my experience. It was women for women. People like Judy Woodruff, Greta Van Susteren, people. Women supported each other. I mean, I can think of a couple that maybe passed a rumor or two, but in general, it really was about women supporting other women.

[Morgan Lavoy]

So when you see my email, I'm sure you don't remember this at all, but just based on that culture, you thought, okay, I'll help this young whippersnapper out.

[Darren Kagan]

Well, not to make you not feel special, but I'm sure you're not the only one that I invited to come sit on the anchor set. Like, that's. That was not a lot out of my day. I'm sure it's not that hard to be nice, and it's not that hard to share.

[Morgan Lavoy]

Well, it was so gracious of you. And then three months later, I got a call. They're like, come to Atlanta. I was like, am I getting punked? Is this a joke?

[Darren Kagan]

I think what's interesting about your CNN experience, it was probably five to 10 years ahead of its time. For the project that they brought you in to do, it was a streaming service. Like, here was a crazy idea. We're going to have people that are just going to be streaming the news on the Internet. Like, what is that? And it ultimately didn't make it, not because of you or because of the people who are involved. But I really do think it was too early.

[Morgan Lavoy]

Yes, the entire department got let go, which was a fascinating experience for me. But when I started. So I got there, 2006, and you were leaving.

[Darren Kagan]

Yes, that's exactly when I was leaving.

[Morgan Lavoy]

At the time, I had no experience with announcements. I just thought, when people say, I'm moving on to due other things, those are true. And so I had no idea why you left or what the story was.

[Darren Kagan]

So. Well, I still don't know the whole story, but I'll tell you the part of the story that I do know. It was January of that year, and I was on the set and was breaking news, and there was an email from the big boss, I think it was John Klein at that time, and said, hey, when you get off the air, why don't you come see me? I thought he was calling me up to tell me what a great job my team And I did on breaking news that day, which I assure you we did, because we were very good at that. And instead, he called me up and 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, but I'm not going to let you go. I'd like for you to stay. Well, I think I would. I'll let you know. So every day I came to work after that for like nine months. I didn't know if that was going to be the last day that I spent. I mean, I'd spent 12 years there, which was a little stressful, but it also was a gift because I didn't know the thing. I hadn't figured out the thing I was going to go do next. So it was kind of quiet. And then about Labor Day, they called me and they said, okay, now we're serving. Now we know we're gonna let you go. And then that was it. But what's so unusual about that? Usually with on air people, you know when. When you're done, you're done that day because they don't want to kind of put you on the air and let.

[Morgan Lavoy]

You say whatever you want. Like I, this guy, John Klein.

[Darren Kagan]

Boo. And I never asked why people go, well, why they let you go. I was really clear. I was never going to ask why, why, why? Because why doesn't matter. I mean, you know how subjective that business is. It's kind of like toothpaste. If they decide they don't like you anymore, they don't. You work by contract. Two, three year contracts. It's not France where you're guaranteed employment for life. And I also probably figured I wouldn't hear the truth. Is it because you make too much? Is it because we didn't like who you were dating? Is it because any particular thing? It was enough to know they didn't want me anymore. So it's like, all right, peace out.

[Morgan Lavoy]

Wow. I mean, that was so grown up of you. Because when I got the call from hr, all I said was like, why?

[Nicole Lapin]

Why?

[Morgan Lavoy]

What did I do? I didn't know, but I. Yeah, it was the first time I had ever experienced like a layoff or a firing or anything like that. And probably with breakups at the time, later on you learn it doesn't really matter why.

[Darren Kagan]

Although I would say there are plenty of guys that did ask why, but I wasn't going to ask you. But did they tell you why?

[Morgan Lavoy]

No, it was HR mumbo jumbo. But I didn't Know that you're never going to get like satisfying answer. You're never going to get that closure.

[Darren Kagan]

So now you're the big boss woman. But if this situation happened to you again where somebody was going to discontinue you or you did get fired or not continued, would you ask why?

[Morgan Lavoy]

No, I don't think so.

[Darren Kagan]

Everything ends. That's where I've kind of come to my life. Every job, every life, every relationship, everything will end. And the kind of the why it ends eventually doesn't matter. It just ends. And that's not. People are like, oh, that's so dark. But I actually think it's light because then you appreciate what you have while you have it, knowing that it's not going to be forever.

[Morgan Lavoy]

Well, the good and the bad.

[Darren Kagan]

Yes, exactly, exactly.

[Morgan Lavoy]

And did you think when you heard around Labor Day that there was going to be no other role, like maybe originally you thought you would be reassigned to another hour?

[Darren Kagan]

Well, no, I knew that wasn't going to happen. So the gift of not being let go that day, it did give me time. First I had my sad where, you know, I crawled under my covers and had my cry. And then I kind of started looking around, well, what am I going to do? So the options then were try to get on with another network like get up to MSNBC or Fox or one of, you know, ABC or cbs. That would have meant moving. And I really didn't want to do that. Going back to local. I really didn't want to do that. I also had kind of a realistic look of, well, I could go to the next thing, but I knew I was going to age out. It's not like all women can't. There are some women who go forward, but eventually some 20 something comes up and at that pay rate, that pay rate, they will kind of scoot you out. And I came up with my idea. I decided I wanted to do uplifting and positive news. And it was just the beginning of journalists being entrepreneurs. I mean, by the beginning, I mean the very, very beginning. So I went and had my own website built. I came up with what I thought was a good business model, which actually wasn't, but it was a thing to go do. And so when they said, now it's time, I was like, okay, I did go. I did say to the big boss at the time, I said, hey, I actually have this idea and it might be good for here. And they never asked. They never asked me what. They didn't say what it was. They say, well, good luck to you. And they let, and they let me go. And then meanwhile after I left, then they started like CNN heroes and they did start a lot of kind of good news, positive things. But that's okay. That was their thing and I went off to do mine.

[Morgan Lavoy]

I want to double click on the age out situation. So did you feel like there was an expiration date?

[Darren Kagan]

I think there was. And I will be so bold as to say there is an expiration date. Not for like if you're a really big star, not for the Barbara Walters or for heaven's sakes, Gayle King is 70 years old leading that. But if you're in that weekend midday, those, those slots that can be really used to develop an up and coming talent. I think as a woman, at a certain point, yeah, I think there is.

[Morgan Lavoy]

What point?

[Darren Kagan]

Somewhere in your 40s, I would say great.

[Nicole Lapin]

No, no.

[Darren Kagan]

But no, that's why you are where you are, because now you're your own boss. No, I'm not saying not today. I'm saying in that news world, I don't think you'll see, see a lot of weekend midday, that second tier slot, women over 50, let's say. And now you're gonna go click and say up there, you're right.

[Morgan Lavoy]

Has it changed?

[Darren Kagan]

I don't know how much that it has, but I think I'm also just kind of a realist. Like when I went from news into sports, it is a man's world. Like, I knew when I was doing sports, if a male sports anchor mispronounced someone's name, it would be, oh, well, he just messed up the name. If a woman mispronounces that name, oh, look, clearly she doesn't know sports. And that's the rules of that game. And it's not fair, but it kind of is what it is. And you go and you partake and then when it's not for you anymore, you go on and go do something else.

[Morgan Lavoy]

Did you have that feeling?

[Darren Kagan]

No. And I, I certainly did not expect. I, I mean, I was blindsided. I did not expect that that was going to happen. I had already survived like six or seven bosses. I was always the put me in coach, like, go do. And I was really good at my job. I did, I was not expecting it. But now that I look back, I can go, oh, yeah, okay, that's, that's part of what that was.

[Morgan Lavoy]

And when you left, did you try to go to Fox or.

[Darren Kagan]

I was working with an agent. I had him send some tapes out. But at that point I was really excited about Going out on my own and kind of doing this thing and picking myself, like hiring myself, because I really wanted to do uplifting and positive news. And I think I was branded in the industry as, oh, she's a really strong breaking news anchor who we've watched On CNN from 9 to noon for the last, I don't know, 10 years, whatever. So that would be. If I was going to try to get to CBS or abc, I think that's what they would see me as. I couldn't really show up there and go, hey, I think you should do uplifting and positive news. And I want to be the one to do it. That was going to be a hard sell. 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.

[Morgan Lavoy]

You absolutely chose yourself, it seems like.

[Nicole Lapin]

For the first time, you know, I.

[Darren Kagan]

Think to get to cnn. So I was working in Phoenix. They had made me sign a five year contract for $19,000 a year. Since we like to talk money here. No outs. When you talk, I mean. No outs. Yeah.

[Morgan Lavoy]

Mine was 18,000 in Palm Springs.

[Darren Kagan]

Yes. Yeah. I mean, Diane Sawyer could have keeled over and ABC could have called and said, we want Darren. And that news director would have said, hell no, she's under contract for $19,000 a year for the next 10 years. No, it was a five year contract, no outs. I counted down to the end of that. Like my whole life was going to change at the end of that five years. And it got to like year four and it was like nothing was kind of really happening. So that's when I got the idea to do sports. And so I went into that news director. Oh, that news director. By the way, I was the only brunette on that station. Everybody else was blonde. And when I would go in. Yeah. So I was a reporter and I would go in, kind of a chance to anchor. And he would say, darren and tv, there's just this, it. And some people have it and some people don't. And clearly you don't. So if you work really hard one day you'll be a really good reporter in Phoenix, Arizona. But why would you dream of being anything else? Chip on the shoulder.

[Morgan Lavoy]

Yeah.

[Darren Kagan]

Anyhow, so I got the idea to do sports. The sports guy pulled me over and said. The weekday guy pulled me over and said, women don't do sports. I know this sounds like 1892, but it wasn't. But still, it was still kind of new for women doing sports. And they started a Weekend morning newscast. And I went into that same news director and I said, hey, you're starting this morning weekend thing. I want to be the sportscaster for that. And he said, that show does not have a sportscasting position. And I said, I know I made it up and I gave it to myself. And at this point, I was his top reporter. I'd worked really hard, so I was the night side reporter. And you know how it works in news. If you work weekends, you get two days off during the week. And it's like, I'm not giving you Thursday, Friday off so you can come do sports. I said, what if I do it on my own time? He's like, you're going to work seven days a week for $19,000? I said, oh, we'll do it for a month. Let me try it for a month. And you know, what was he going to say? I was offering to do something for free. I knew he was never going to watch this thing. So I could do it for as long as I needed or wanted to. I could just let me try. If I'm bad, you pull me off the air, and if I hate it, I'll stop doing it. So he let me. And I did it for a year and a half. I worked seven days a week, night side during the week, mornings on weekend mornings. And still it got to the end of contract, and still I had nothing. I had an agent who was sending tapes out. Nothing, nothing, nothing. So this little TV station came to me and said, okay, your contract's up. You're going to sign this extension. You're going to stop doing sports. No anchoring and no outs in two years. I mean, it was ridiculous. And I said, I can't, I can't do that. I said, okay, you're going to sign this instead. You're going to look for a new job and we're going to look for your replacement. And whoever wins gets to give the other person seven days notice. What the heck? So I signed that. I'll fast forward the story. But I got the CNN offer and I was able to go in and give him my seven days notice.

[Morgan Lavoy]

Wow, those are wild times.

[Darren Kagan]

Yeah, but. So there's all things. Yeah, I bet on myself.

[Morgan Lavoy]

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[Nicole Lapin]

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[Morgan Lavoy]

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[Nicole Lapin]

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[Morgan Lavoy]

You were, you were an intrapreneur before you were an entrepreneur. Like I think too at cnn I was able to create series and things within the organization. But it's a totally different animal to be an entrepreneur versus intrapreneur.

[Darren Kagan]

It is, but you're kind of doing on someone else's dime with someone else's toys. There's always opportunity even in a dead end job.

[Nicole Lapin]

I agree.

[Morgan Lavoy]

But what's really cool when we were last catching up is that even though you were blindsided, you had an amazing financial advisor.

[Darren Kagan]

We can talk about that.

[Morgan Lavoy]

So you had no severance?

[Darren Kagan]

No, no severance. I mean your contract's up. Your contract's up. Nothing.

[Morgan Lavoy]

But you had like a few months of heads up.

[Darren Kagan]

Well, right. And so let's go back. So I was very well paid. So in Phoenix, I was making 19,000. My first job at CNN doing sports was $50,000, which I mean you could have just shot me right then, you know, to more than double. I paid off with a little credit card debt I had left from Phoenix. And I mean I bought my first townhouse and I was, I was happy. And then did sports for three years. It kind of went up a little bit and then a new boss came in and offered to make me a news anchor. So then I was making low six figures and that kind of just doubled. Doubled that. By the time I left cnn I was making a half million dollars a year and single, no kids. Yeah. And so when I really started making the like six figures, I was connected. Actually the same friends that eventually introduced me to my husband introduced me to their financial advisor. A woman that completely rewired how my brain thought about money because I did not come from a healthy money environment. My dad was a compulsive gambler. We kind of just made it up. As we went along. Those parents started to kind of lean on me. Yeah, it wasn't good. But so through her, I sat down with her and she said, this is what we're going to do. We're basically going to save 2/3 of what you make as a CNN anchor. And she's like, I don't want to be punitive if we're saving too much and you're not doing the things you want to do, then you know, we'll ease up on that, but let's try. And so that's what we did. So she was the first person I called and went to see when CNN let me go. And I was sitting in her office across just like I'm sitting from you. And I'm like. And I'm like. And she has got the biggest smile on her face. I'm like, margaret, what is wrong? Did you not hear? I said they're letting me go. And she pulls out my statements on paper then. And she's like, look, look what you've done. You've done this and you're fine and you have this cushion and you can go do all these things. She goes, plus, you were making this. And she puts her head up, her hand up high. She's like, but you've been living on this. And this is true. She's like, darren, your. Your idea of fun is you go buy an extra chicken for your backyard coop. You know, like you're not out there buying fancy shoes and purses. And so to match. That really wasn't as hard. I didn't have to go meet. I was living so far behind my means, let's just put it that so far below my means.

[Morgan Lavoy]

I mean, you're the opposite of lifestyle creep.

[Darren Kagan]

Yes, the opposite. So I had money to bankroll what I wanted to go do. I had an idea of what I wanted to go do. And so off I went. Did I do it like the most smart? Did my original idea make great money? No. I mean, there's been a ton of things to figure out since then, but the opportunity to go do what I want to do, not only did I have that, but I created that. And that was very empowering.

[Morgan Lavoy]

Beyond empowering. And how much Runway did she show you? You had like, in your mind, did you think, I have a year, I have two years, I have five years.

[Darren Kagan]

I mean, it was such a different time. So I wanted a website. Well, at that time, I think I spent like $25,000 to have a website design today. I could whip you up one on WordPress myself.

[Morgan Lavoy]

Yeah, I could do it well, shoot.

[Darren Kagan]

ChatGPT. Yeah. Would just create it for me. But that you had to pay like a thousand dollars a month for the software to run it. I mean, there were definitely expenses. I needed some help editing it. Things definitely weren't as self serve and cheap as they are now. I did not know. See, that would be a Perfect example. How much Runway. I'm like, I don't know.

[Trent Swanson (Miles Husband)]

Let's just.

[Darren Kagan]

I still had a little bit of the Kagan in me.

[Nicole Lapin]

I don't know.

[Darren Kagan]

Let's just start and we'll figure it out. With Big Dreams.

[Morgan Lavoy]

I mean, I remember when I got let go, I had like $4 at a. @ a Pikachu doll. I didn't have very much, but it.

[Darren Kagan]

Was a different time, so. But when you were the first let go of cnn. Well, that was like the equivalent of where I was. Certainly you're making more at CNN than I was making at. In Phoenix. You're making more than 19,000 a year. Yeah.

[Morgan Lavoy]

At CNN, I made 80,000.

[Darren Kagan]

Right. So. But still.

[Morgan Lavoy]

Which was so much money for me.

[Darren Kagan]

It was great. But you hadn't had a chance to build.

[Morgan Lavoy]

No, I was in credit card debt. It was. Well, yeah, I thought this was many X what I was making in Palm Springs.

[Darren Kagan]

Yes. And it was.

[Morgan Lavoy]

It totally was, but I was. When I was blindsided and got a call from HR and. And asked why, and I still had time on my contract, which was bizarre at the time because I could have gotten paid out, but there was part of the stipulation that if you got another job, you don't get severance. So I got another job pretty quickly.

[Darren Kagan]

You almost can't afford to go to work.

[Morgan Lavoy]

I know.

[Darren Kagan]

Yeah. Unless it's for more.

[Morgan Lavoy]

But I was so scared. I was so scared. I had no safety net at the time.

[Darren Kagan]

I get it. Well, that's where I was in Phoenix when they said, sign this thing for seven days. I mean, I. I had no savings. And of course there's always involved, like, the guy had dumped me and like, there was. The decks had been cleared. There was nothing. There was no fallback. So I understand. I definitely understand.

[Morgan Lavoy]

But.

[Nicole Lapin]

Margaret.

[Darren Kagan]

Shout out to Margaret Graf.

[Nicole Lapin]

But it's just.

[Morgan Lavoy]

It's so scary when. When a huge thing like that happens, if the financial component is just as shaky or worse, it makes everything, everything harder because you're already going through such a whirlwind.

[Darren Kagan]

I remember I was walking down my street. So, okay. When CNN let me go, another relationship had ended. So I was walking down my street, walking my dog, and I ran into a woman who lived, like, halfway down the block. She was pregnant with her fourth, trying to get a real estate license, totally overwhelmed living in this house they had bought that they thought they were going to renovate, and they didn't. And I'm just walking down in a daze, and she's like, what's wrong. And I said, I just lost my job. My relationship ended. I don't have a tie to a single thing in the world. And she looked at me, she. That sounds like heaven. So my, like, nightmare was like, her fantasy at that point because she was overly tied down. But it was. But it was too much not tied down. Like, where do you live? Do you live in Atlanta? Why? I was living in Atlanta originally because I moved there for CNN and I owned a home, and it felt like home, but I didn't want to come back to la. Like, there was nowhere I could go anywhere and didn't want to go anywhere.

[Nicole Lapin]

Yeah, and the world was changing, too. The paradigm.

[Morgan Lavoy]

I mean, we saw then, you know, Paris Hilton leaving jail was breaking news on cnn. And I was like, wait a minute. I went to journalism school. What are we doing? Things are changing. The Kardashians are hosting the Today show. Mario Lopez is hosting a big entertainment show. These were the pinnacle of where you were told you were supposed to climb to in this space. And it was changing so quickly.

[Darren Kagan]

It was changing. And it was just, like I said, the beginning of, I mean, the idea when we. And I know we started our careers very far apart, but even when you started the idea that a journalist could be an entrepreneur, you might as well own a noodle shop, I mean, there's just no. You went to work for big corporations and they empowered you and you played by their rules and you made them money and they paid you money. The idea that you have your own thing like this, like what I have, it just unheard of, unheard of. And, you know, when you came on my podcast and we were talking about this, you talked about how when you were one of the early people to go out and start in creating your thing, and people told you, are you nuts? Look, look, you're going to give up all this? And you said, actually, yes, I am, because this is not what you promised it was going to be to me when I started, for sure.

[Morgan Lavoy]

I was, yeah, 21 when I got my dream job, 25 when I lost my dream job, I tried to reframe it. At the time, it was really, really hard for me. Was there a year that you felt like it sunk in that you weren't under the covers anymore? Like, how long did that process take?

[Darren Kagan]

So if they told me in January and I finally left in September and I launched in November, probably it was spring or summer. And where the idea came from was so Yahoo at the time, which was big, had hired. Gosh, now I'm forgetting His name. CNN had a war correspondent and they hired him to go to, like, every bad place in the world for a year. It was like the war. The war room or something. I can't believe. I can't remember his name. Anyhow, so I'm like, well, wait, you can do that? Like, you can have a website where you just go do the kind of news you want to go do. And then just like, as an intellectual exercise, I asked myself, well, if I did that, like, what would be mine? And it was clear. It was like, I always loved uplifting and positive news. I said, I would love to just to do uplifting of positive news. So I went through somebody. Through somebody. I actually had a meeting with Yahoo. Can I tell you my pitch? Because to this day, I think it is a very.

[Morgan Lavoy]

Let's go.

[Darren Kagan]

Okay, so you go on Yahoo.com you can get your stocks, your sports, your news, your war. Where's the Yahoo. And Yahoo. Click on Yahoo. And get uplifting and positive news. Like, give me that.

[Morgan Lavoy]

That pitch didn't land.

[Darren Kagan]

Never heard from them again. But then it was my little sister who kind of said, what are you doing? Like, why are you giving this idea away? Go create a website and hire yourself.

[Morgan Lavoy]

Go to good news. Well, because for so many years, you were covering the worst news.

[Darren Kagan]

I was. But when I had my own. For that. For that big stretch, I had my own show on cnn, I could realize I was getting ready. I was creating segments like, oh, let's do our uplifting story of the day. I was booking these kind of guests that were doing people who were changing the world. And so there were little spaces. Yeah.

[Morgan Lavoy]

But overall, it was doom and gloom and death and destruction and I don't know if you had nightmares. I would. After Virginia Tech, I was on the air for a lot of hours and I would have lots of nightmares.

[Darren Kagan]

Did.

[Morgan Lavoy]

Did it affect you in that way?

[Darren Kagan]

I mean, sadly, I. With news, I could talk about the worst things in the world and get off that set and be a goldfish, and I couldn't. We could go to lunch that day and you go, what happened? Now I can't see any horror movies like Fiction and Bad Dream to this day. I can't. I don't know why fiction affects me that way. News.

[Morgan Lavoy]

So the good news wasn't a response to all of the bad news?

[Darren Kagan]

No, Just kind of more what I'm drawn to anyway. Sunshine and puppies and babies.

[Morgan Lavoy]

Thinking back, I was also single when I was let go. And it was this weird time where I was like, do I stay in Atlanta, do I not? I don't know. And I thought I was just going to be broke, alone and homeless and die in the gutter, which is still my fear.

[Darren Kagan]

And how'd that work out? Yeah, I think it's working out a little bit different for you, Nicole.

[Morgan Lavoy]

Although it's very funny that this woman that was pregnant on your street told you how freeing it is. Because just yesterday we had an interview of a woman who came in and I was like, oh yeah, I haven't seen you. Lots of stuff happened. I got married, had a baby, house burned down in that order. She's like, like, is that freeing? I was like, well, nobody's ever asked me that. But interesting question, just losing everything that you've ever owned.

[Darren Kagan]

Which could be a little insensitive, I think, for someone. And maybe that was insensitive for her to say that. I just felt like the three things I always wanted to be a wife, a mother and have a career. Here I was, I was 40, I'm in the early 40s of like, and I've done none of it. I have no claim on any of it. I don't have the guy who wants me, I don't have the baby. I had a great dog and a three legged cat and some chickens, but the career didn't want me, the guy didn't want me and I. Yeah. So what was this all for? And it wasn't for lack of trying in all those departments, but fast forward.

[Morgan Lavoy]

I wish that current Darren could talk.

[Darren Kagan]

Oh, it just should have had so.

[Morgan Lavoy]

Many conversations when she was leaving cnn. What would present Darren say to her?

[Darren Kagan]

It's all going to be fine. He's on the way. He's taken a long time to get here, but he's on the way.

[Morgan Lavoy]

And he's worth the wait.

[Darren Kagan]

Yeah. Oh, not only was he worth the wait, but the person I am today to be with him was worth the wait. That honestly. And you're going to get to meet him and talk with him. But I wouldn't have dated him when I was at cnn.

[Morgan Lavoy]

So how did you meet?

[Darren Kagan]

We met through the same gay boyfriends who introduced me to Margaret, Craig and Michael. I owe them everything. My money and my husband, we, I was a third wheel. They had a son, you know, in Atlanta, there's these springtime festivals and I'd gone with them and their son to Summerfest in Virginia Highlands. And I was with one of the dads, Michael and Craig went to the funnel cake line and in the funnel cake line he found himself standing Behind a fellow dad who had a little girl at the school where his son went and just kind of casually invited them over, like, oh, a bunch of us are sitting and they come walking across the field and Michael starts punching me in the arm going, single. Single. Incoming single. I'm like, I'm hot and I'm sweaty and I'm like, yeah, Michael, today's not the day. And he sat down and we met and it was loud. I mean, it's not like the mo. It was like that man moment was magic. But we met and then they left. And then Michael looked at me and said, well, what'd you think? And I went. He's like, well, that's more than I've heard out of you. I had like dated in four years. So if Michael went on the PTA contact list and reached out to the man we know as the husband today and to say, you know, just wondering, are you in a relationship and are you, you know, available? And he wrote back that it's complicated. And I heard that and I'm like, okay, I don't do complicated and forgot about it. But like a month later, he emailed me and asked me out to coffee. And here we are.

[Morgan Lavoy]

What happened next?

[Darren Kagan]

So we went out for long coffee, then he ghosted me for a few weeks and then he popped back again. And so his story was he was a single dad, married, had a child, and they got divorced and then his ex wife died. So he, when we met, he was raising. He was single dad raising his daughter alone. I had never actually dated anybody with kids, which I can't believe I went that far. But let alone, I mean, it's one thing to relate to date a divorced dad, but he was like a full time single dad. It was just him and his daughter. And so we went to dinner and I said, well, how does a single dad date? And he said, well, how does therapist Joe say I should date or how do I date? Like, let's start with therapist Joe. He said, therapist Joe said that he certainly allowed to date, but he should keep it separate from his daughter because she has already experienced loss. She's already lost her mother. And he's like, yeah, that's not how I date.

[Morgan Lavoy]

But having a therapist is a green flag.

[Darren Kagan]

Yes. Oh, there are a lot of green flags about him, actually. If you want the ultimate green flag, date a man who's a father. Because you see, it's, it's fast forward. I kept investing in these single guys, thinking, oh, they'll turn into this. But this was kind of like, rooms to go. Like, you could see, you know how, like, on social media. Now let's get to the good part. Like, you see him in the good part. Like, you could see, oh, wait, he is. He is on this earth to be like a husband and a father. Like, this is how he does it. There's no question. Anyhow, we dated a couple years, we got married. I legally adopted her. So that was my sideways into motherhood. And then the year before I met them, I'd signed up to be a big sister in the big Brother big sister program. And because of what was happening in that little girl's life, she came to live with us full time. So I went from single, no kids, to married with two little girls. With exactly the girls, the kids I was meant to have the whole time. No angst of, oh, I need a biological child. And that's how we became this family. Wow. So I would have told her to go back to your question. I would have told Darren, sad Darren, what you want is not coming. What's coming is better than you could ever dream for yourself because it's bigger and better and exactly what was supposed to happen. That's what I would tell her.

[Morgan Lavoy]

I'm so, so in the deepest part of my soul happy to hear you say that. And he. I would love. He's here. I see him from my eyeline. I'd love to invite him on.

[Nicole Lapin]

On.

[Morgan Lavoy]

Because you guys have also, in addition to being in love and parents get free flights in the most fascinating ways.

[Darren Kagan]

Before we do, I just want to say, because I know your demographic is that 30 something, 30 to 40 woman. Like, it. The demographic is who I was. And it's not just women who are worried about money, but it's women worried about, like, where are all the good guys? Um, and I would just say, just know he's on the way. And that that family can look very different than what you think it. It's supposed to be. Um, and when you open your mind to that, like, the magic can really happen.

[Morgan Lavoy]

You never gave up on that dream.

[Nicole Lapin]

It just.

[Darren Kagan]

Oh, no, I gave up.

[Morgan Lavoy]

Oh, you did?

[Darren Kagan]

Yeah.

[Morgan Lavoy]

When did you give up? Right before.

[Darren Kagan]

Right before? Yeah.

[Morgan Lavoy]

It's so funny. I gave up on the dream, Right. But before I met my husband and.

[Darren Kagan]

That they go, once you give up.

[Nicole Lapin]

I know.

[Morgan Lavoy]

I hate cliches, but it's true. Like, I really, really. I gave it lip service for a long time. I was like, no, it's fine. But then I really believed. I was like, I am. I'm fine. I Wrote through what life would be like as a mother for, you know, women that I was talking to as, like a different kind. I really rethought it and like, I imagined what that was and I was actually cool with it.

[Darren Kagan]

And then I had so let go of it that when I met Trent, who you're about to meet, one of the things I thought was so hot about him is that he was a single dad. So I thought, oh, he's busy Monday through Friday. I'll always see him on the weekends. That's perfect. I have my weeks to myself. And he was the one who said, no, hold on, like, if we're not really going for this, like, I became the non committal one and he became the one who's like, look, are you in this or you're not? I said, what?

[Morgan Lavoy]

That's sexy.

[Darren Kagan]

Yeah. Well, he like kind of got whipped me in shape. I'm like, oh, okay.

[Morgan Lavoy]

He knew what he wanted. He knew. He knew the value that was in front of him. Like a smart, smart man.

[Darren Kagan]

Well, no, he was clear about what he wanted and he wasn't sure that I was that, like, if I didn't, if I wasn't going to be all in. He was not interested in somebody who just wanted to see him on the weekends. He wanted a full time relationship. First time I ever found one of those people. And so I married him.

[Morgan Lavoy]

So you gave up and then you un. Gave up.

[Darren Kagan]

Yes, exactly. But I truly, truly gave up. Gave up.

[Morgan Lavoy]

Yeah, I know. Why is it like that all the time?

[Darren Kagan]

That's one of the physics of love.

[Morgan Lavoy]

In addition to all of his amazing attributes, you call him.

[Darren Kagan]

So my term of endearment is husband, not sweetheart or sweetie or whatever. Because I can't think of a more a bigger term of endearment since I never thought I would get one of those. So I just call him Husband. That's like my sweetheart name. And so then he'll call me wife and yeah, I love it. And then branded him Miles Husband, which we will.

[Morgan Lavoy]

Why do we call him Miles Husband?

[Darren Kagan]

Because about the time we started dating, he came up with a points and miles system to completely organize our finances so every dollar we spend brings a point or a mile or multiples of that back so that we're able to travel the world in luxury while spending pennies.

[Morgan Lavoy]

Hell yes.

[Darren Kagan]

And my friends were like, how do I do that? Like, this is what we do. Let's. Let's brand you. So I said, you're Miles husband. I grabbed mileshusband.com, built him his Social media. We did some media training. We'll see how I did. And set him on his way.

[Morgan Lavoy]

Let's meet up. I'm so excited. So, so honored to say Trent Swanson, AKA Miles husband.

[Nicole Lapin]

Welcome to money rehab.

[Trent Swanson (Miles Husband)]

So glad to be here.

[Morgan Lavoy]

So you just heard Darren recount your romance. Anything surprise you?

[Trent Swanson (Miles Husband)]

I was a bit disentangled at the time. She in fact wasn't having a great day because she was still mourning the loss of her prior relation, yet somewhat dated historical relationship. It had been a while, but that particular person. Yeah, yeah. I hadn't explained the tears coming out of your.

[Darren Kagan]

The reason I was spending so much time with Craig and Michael on that particular weekend was the person I had dated four years previous was getting married that weekend and I was as brokenhearted as if we had broken up the weekend before. And so the weekend that Craig and Michael were keeping me busy, busy, busy is the weekend I met my future husband. So when did the tears mean?

[Trent Swanson (Miles Husband)]

Is it the bad band music and back? Is it, it's too hot out? Is it, you know, why are there tears coming down?

[Darren Kagan]

Oh, that's when he met. Yeah.

[Trent Swanson (Miles Husband)]

So our first meeting, she was crying. Yeah.

[Morgan Lavoy]

So when you guys got together, you started an experiment, right, where you're just trying to get free tickets to Miami.

[Trent Swanson (Miles Husband)]

So I read a column written around, right around 2012 where a person said, take advantage of this promotion, you know, which is buy a pair of shoes at a specific merchant through a specific technique and you get enough points and miles for two free first class tickets to Miami. It's like, oh, what is this nonsense? That's impossible. Right? If everyone could do this, there would be no more flights. And so I said, well, let me just try it. So I read the very short, succinct article, read it, followed the steps two weeks later, had enough points for these free tickets in hand. And I thought it was the greatest thing in the world because I thought the nirvana, the best place to be was flying in a recliner seat on American Airlines for a two hour flight. I thought that was the pinnacle because I didn't know total newbie. So we did it, loved it. Then I started thinking, wait, are these techniques scalable such that I can outsize, upsize, upscale up, elegant for similar amount of work? Can I do that and really make this thing phenomenal? And so that's, that's how Miles Husband, the hobby was born. I think the branding came from Darren a couple, couple years later. Yeah, yeah.

[Darren Kagan]

So that was the beginning. That was the gateway drug. Those pair of shoes and then I was like, oh, if I order this this way. And then. Oh. He started with credit cards. And I mean, there's been some pretty crazy things the day we got married. So we got married next to a waterfall, which is us and our two girls. And we drove from Atlanta to North Carolina. And we're up in the highway, we're all in our wedding gear. And he gets off the highway and pulls into the CD motel. I'm like, what are you doing? And what were you called? A mattress run.

[Morgan Lavoy]

Oh.

[Nicole Lapin]

What?

[Trent Swanson (Miles Husband)]

So yeah, back in the day, I guess it's going back 12 years now. Almost no more.

[Darren Kagan]

2012.

[Trent Swanson (Miles Husband)]

Yeah. So you could achieve loyalty status by the number of stays at a given hotel. In a hotel chain, the amount of dollars per night didn't matter. It's just. Did you get a stay credit? You compile enough of these day credits, you get to be elite status, which gives you upgrades. Big sweet rooms, nice big breakfasts, especially internationally. So there's a technique that used to work still somewhat does work is where you can check into a hotel and not stay. So you get a great rate. You check in, you leave, and you check out by phone or not check out at all. And you just go to your account and you see your elite status credits post. And pretty soon enough mattress runs, we'll get you fantastic benefits because you had a job.

[Darren Kagan]

That's a job, right?

[Trent Swanson (Miles Husband)]

Right. Yeah. This is a side hustle job. Passion joby.

[Darren Kagan]

Yeah, but it's.

[Morgan Lavoy]

It's grown since then. So you got these free tickets to Miami. You got the coveted leaflet seat.

[Trent Swanson (Miles Husband)]

Not on that one. That was a recliner.

[Morgan Lavoy]

A recliner seat.

[Nicole Lapin]

You got the coveted recliner.

[Trent Swanson (Miles Husband)]

That's where we started. And I realized the same techniques, adding a few other techniques can get you butlers and showers in the sky and Krug champagne. And not only a life flat beds, but the entire suite, which has walls and a ceiling with your butler window. You can do these same things on those luxury airlines. Emirates at odd jl. So that. That's where the scale makes the time investment really, really pay off.

[Morgan Lavoy]

Because you guys have pictures, Gloria's pictures, and Emirates with the butler. You went to Japan for $5 and 60 cents. Sorry, you went to Japan for $5.60. So how do you strategize?

[Trent Swanson (Miles Husband)]

This is really a growing business. The credit cards are. The credit card points purchases are the largest profitable segment of the airline business. And so it's a really big space out there. There's a lot of noise. There's clear. But the Real strong signal is, you know, as a normie who wants to travel luxuriously, the best thing to do is build out a plan on where you want to go, how many people are going, what's the minimum class of service, and how flexible is your calendar. So answering those four questions will drive you to earn the exact types of airline points, the exact type of bank points where you can most efficiently redeem those for that travel, and also with the least amount of out of pocket spend.

[Morgan Lavoy]

Because when I first heard about this, you do to my friend where you say, I'm not going to tell you when we're coming home or where we're going or how we're getting home, but we're going in business class. I do like that part. Or first class.

[Darren Kagan]

What?

[Nicole Lapin]

Why?

[Darren Kagan]

So there's two parts of it. There's the earning side. How do you earn the most and best points? And that's kind of what Trent was talking about. And then there's the burn side. How do you actually find the tickets? Because I'm sure anybody who's listening, who's interested about miles and points has tried to go and book a ticket and can't find either. Can't find it. Like, what do you mean? I need a million points points. So there's the earn side to get good on and the burn side.

[Morgan Lavoy]

So let's go to the earn side. How do you. What's the best way?

[Trent Swanson (Miles Husband)]

So what's more important though is you really work on your, your vision. You, you define that vision, answer those four questions.

[Darren Kagan]

Where do you want to go?

[Trent Swanson (Miles Husband)]

Is where do you want to go? What class of service, how many travelers, how wide or narrow is your window date? Window. Right? And so answer those questions. That's the burn side, right? That will tell you exactly the template it for the EARN site. And so you have to kind of work backward, reverse engineer this. Because what really happens here at lax, right? People show up with a pile of American points and a pile of sky miles, right? I want to go with fly the Etihad Butler with my sky miles. Well, guess what? You, you didn't tell us that in the beginning. You didn't lay out your vision. And there, so what did you do instead? You collected blindly these series of loyalty points without knowing how they're even redeemable. If you only drink the Peet's Cafe Mocha, why you earning Starbucks star points? Like you're never going to be able to use those at Pete's. Go to a car dealership, you say you want a car, the dealer Instead of asking you the qualifying questions, family van, sports car, snow tires and city takes you to the car that has the highest dealer holdback percentage. Right. So that's what you really want to avoid is you want to earn points and spend your money with a purpose. You purposefully earn the points exactly. Targeted to the luxury tour, the luxury destination and location that you want. And that's, that's the big. One of the big secrets of loyalty points is if you lay out that model, it becomes more simple, less out of pocket spend. And you don't earn points that you'll never have a strategy to redeem because every dollar you spend earning an airline mile costs you 2 percentage points in discount. Because most people who want to travel coach to see grandmother in Tulsa should probably just get a 2% cash back card and then write a check to themselves every month, put it in a dowry, travel grandma, travel dowry and go in there and buy your ticket with cash. That's the simplest way for folks who want to really travel in economy class domestically.

[Darren Kagan]

But like producer Morgan was saying, she and her husband still want to take a honeymoon.

[Morgan Lavoy]

So let's reverse engineer that. So what would be the best way to get her to. I don't know. Where do you want to go? Fiji.

[Trent Swanson (Miles Husband)]

Find a partner who wants to go on a honeymoon with you.

[Morgan Lavoy]

Check. We got that. So let's say Hawaii. We want to go to Hawaii.

[Darren Kagan]

Oh no, we have to dream bigger than Hawaii.

[Morgan Lavoy]

Okay, okay. Where do we want to go?

[Darren Kagan]

You know, it's funny because you guys brought it up. Japan is like so perfect.

[Trent Swanson (Miles Husband)]

Great, perfect.

[Nicole Lapin]

Know nothing about it, don't know where to go.

[Darren Kagan]

Perfect. Let's use Japan.

[Trent Swanson (Miles Husband)]

So great. And you're going to be traveling from west coast or east. Okay, so Japan from the east coast. And it's interesting because in the past two weeks, literally the entire mechanism, so the destination and vision didn't change, but the mechanism to earn the best points changed because a credit card card comp issuer created a new partnership with Japan Airlines. So Capital One introduced a brand new partnership and introduced a 30% bonus where you transfer a point and get 30% extra. So they created this big spin up. And so the best way to do this now is if you have capital one miles, you get 30% more. More than you would other otherwise. But now. But the other challenge is this is as you're looking at this redemption side, the biggest mystery that most folks misunderstand or miss or dismiss is inventory is tightly controlled. So if you go up delta.com or any airline.com, buy the ticket, either credit card. The inventory is pretty much infinite. There's 200 seats on the plane. You can buy any of those 200 seats. Award inventory is tightly controlled. Between 101 and 9 seats are made available. So the trick is what's the propensity and tendency, how many tickets are made available? What's the cadence of release when those are taken, are they replenished? When are they replenished? So we get back to your question. Why? What does this wait to the last minute? Because the last minute is a huge award inventory replenishments scheme. So 72 hours out or less, the seats that are not going to be sold with cash are flipped over to this rewards bucket of inventory. And that's what you can really redeem points at the very last minute. So one of the tricks is a wait till last minute to get the best inventory, which is contra the most of our thinking, right?

[Darren Kagan]

But for example, last summer, the summer of 24, we went to Japan. We were like Morgan, her husband, but he, we do, we like to do what's called a spin the wheel vacation where we say okay, we know we're going to go at this time and he'll figure out where we can go. And so we knew we were going to travel. It was like the first week of June.

[Trent Swanson (Miles Husband)]

We had our like 12 day window. So we locked that window. It's one of the four questions, right? What's, what's your window? So we locked in that window and really limited our universe of what we could do based upon that. So while the window was locked in, I went to research which lloyds of programs released which award inventory for which airlines.

[Morgan Lavoy]

How do you know that the inventory is there? A site?

[Trent Swanson (Miles Husband)]

Every airline, every loyalty program publishes their award inventory. And if you track it frequently enough, you can track the trends, the ups and downs, when it stays flat, what triggers replenishment, whether it's first class. But it all really starts with creating that vision. You know, I'm going to Japan, what should I do? And the, the big part of this capital one JL relationship is every loyalty program by rule gen generates its list of available inventory on a calendar. Some of those go as far out as 360 days into the future, whereas others go only go 300 days, 30 days in the future. So that difference between 3330 and 360, if you have access to the inventory at day 360, you will steal it when the programmer only gets access at day 3:30. So how do I, if I'm Going to Japan. I know I have two first class seats on every flight out of Dallas, one out of la, one out of, one out of jfk, three out of o'. Hare. How do I gonna get myself to o' Hare for the greatest chance of that award inventory opening up. And the first thing you have to do is say I've got to get access to the program or 360 days in advance, I can buy it and lock it in as opposed to waiting for 3:30 days when everyone's already picked over the inventory and that seat that you want is not going to be there.

[Darren Kagan]

But even if Morgan just starts with this is where we're going and starts collecting the right kind of points, she and her husband are going to be light years ahead of most people who come to you and say, oh, we help me book my dream vacation and I have the wrong points.

[Trent Swanson (Miles Husband)]

Sure it's right. And so the Capital One Venture card is great for that. Any of the Amex cards are great for that because they have access to that loyalty program who has inventory earlier than its competitors have it for the very same seat on the very same.

[Morgan Lavoy]

Airplane not sponsored by capital1, just FYI.

[Trent Swanson (Miles Husband)]

But it's a little bit of a Rubik's cube. But if you start with that focus and realize I need to have enough miles end points earned 360 or 330 days in advance, then that's how you lay out your scheme. So you're looking 12, 18 months in the future and realizing I need to have a certain accumulation of the right currency. So when the inventory comes available, I immediately know where to go and I lock it in.

[Morgan Lavoy]

Okay, so how did you guys get there for $5? How can Morgan get to Japan for $5?

[Darren Kagan]

Okay, well, yeah, our Japan story. So you found. We knew we were going to spin the wheel, we were gonna go somewhere. I think it was a Thursday. And he said we can do Japan JAL first class, but we have to get to Chicago by Tuesday.

[Trent Swanson (Miles Husband)]

So we had a 96 hour notice and we already had our date windows. We knew our minimum class of service.

[Darren Kagan]

We had our dog sitter, we knew.

[Trent Swanson (Miles Husband)]

Where we wanted to go. And so the only challenge is that we had is to get from Savannah to o'. Hare. And there was a non stop in American and we used some points for that too. So. So that's how we did it. Now it's difficult to to lay out the recipe without naming credit card issuers who are not sponsors. What the best technique is going to do to be is you want to earn points in a, in a loyalty program that has access to long, you know, 360 day inventory. So JAL and Cathay Pacific are two that have access to that. So their program is called Asia Miles. So you open up an Asia Miles.

[Darren Kagan]

Account, which is free.

[Trent Swanson (Miles Husband)]

Which is, which is free. And you would pursue those banks who have relationships with Asia Miles. I believe it's Amex, Cap 1 and C all have relations, meaning you can transfer points into there. And you want to pursue the single bank that has a relationship with JAL, which is capital one. We currently have a bonus of 30%. So understanding those relationships, you can earn points from many, many banks and many, many programs. But what program do these points need to be sitting in? What bucket so I can book the ticket? What's the bucket they need to be in by when to book that ticket? And that's really the mechanism to make this happen.

[Morgan Lavoy]

So explain the window thing to me. So around that time, 330 days before you're going to call the airlines, some airlines.

[Trent Swanson (Miles Husband)]

So really it's, it's the loyalty program. So the place that you deposit, earn points into and the place you pull the points from is the loyalty program. They own the ORD inventory. So if you look at Delta, Skyteam is their alliance. Delta owns its own inventory for its own flights. They also share some inventory on their partners here, France, Virginia, Atlantic. But the loyalty program determines on whose planes, whether it's their own planes or a partner planes. One inventory, you know, gets made available. So you've got to get your points in that loyalty program. You have to know when is the highest propensity for award seats to be released on that program for the destination that you want to go to. Of course you have to know how much it costs. Generally these award charts are static in terms of price, don't change very much. From time to time there's an overnight inflation or a price increase you have to watch out for. But if you, if you're loyal to the right programs that have a low propensity to do that, you're somewhat, I guess, immune from inflation.

[Darren Kagan]

Airline loyalty is an interesting thing in chasing status because that runs a lot of people. You talk with them about that a lot. Like a lot of people, oh, I've got to make gold, I got to make diamond, I've got to whatever make. And you're not a big fan of chasing status?

[Trent Swanson (Miles Husband)]

Well, I, you know, we, we as a test method last year we earned Advantage Executive Platinum, like the highest status except for concierge. Key which is invite only. And so we did it with fly by flying zero miles. So we un American.

[Darren Kagan]

American.

[Trent Swanson (Miles Husband)]

Right.

[Darren Kagan]

Tell them how you did that. So with meal kits.

[Trent Swanson (Miles Husband)]

Yeah. Well so they're Americans program rewards and Delta's getting more this way. It's they have partnerships anywhere from meal kits to hoteliers to different tangential travel companies to you know, muffin manufactured. So if you're a partner ecosystem and you spend your money using a city car city AA card you will earn this concept of loyalty points. And if you reach 150,000 is it you become city executive Platinum. So I found a way by looking at all their partners and all their price lists of their stuff. And I did. Okay. Combination of what's the cheapest, what's the most utility to the family. So don't buy junk just to get stat to buy something that has high utility to the family and which gives you the biggest multiple of those points. So I built like a little three way algorithm them and I found out a technique where I could buy over and over and over again and we made executive Platinum and so eating dinner so so but that's great news. But then you know what's the benefit of that? It's am I going to get upgraded with my super diamond elite status or am I going to sit there like number three or four on the upgrade list and be sitting in the same darn seat everyone else is. And so the challenge is and you even see it in Delta they by strategy no longer upgrade these diamonds because why I can come as a non status member the day of or the day before. I can check in and I can get a cash promo pushed to my mobile phone. Oh upgrade your coach ticket for 299 and I cut the knees out of the hard loyalty earner who's working so hard to earn double triple diamond. And I come in as a no 1 and I spend very little amount of money and I get the seat that they should be giving to you. Yeah.

[Nicole Lapin]

Nice. I think a lot of people also hoard their points.

[Darren Kagan]

They do.

[Trent Swanson (Miles Husband)]

They, they hoard. Well they hoard them because of what of a perceived value. And they, they will have value. But if you're ordering points without the plan to redeem them because they could.

[Morgan Lavoy]

Lose value at any minute.

[Trent Swanson (Miles Husband)]

Well I mean they you know I think the big, the big debate in the points and miles space and part of it is the incentive to keep, keep buying my credit card, keep clicking my Link. I get $200 in my pocket every time you apply and get approved. That's part of the driver. So what they'll say is use your points because they keep devaluing over time steadily. And while that might be true on its face, the point, the value of a point is always a function of the value of the retail price of the ticket. And so as ticket prices have gone up 10, 20, 30% over the past three years and the award pricing remains constant, the value of your point, of your unspent point is even higher now than it was.

[Morgan Lavoy]

We end our episodes, you guys know, with a tip that listeners can take straight to the bank. Is there another one we haven't extracted yet?

[Trent Swanson (Miles Husband)]

I think earning points in miles, there are several techniques to do it. The largest and quickest, most efficient way is through credit card signups. There are other ways we didn't get into very much other than the capital one. I think signing up for credit cards is a serious business. So self examine will you pay your statement in time, you know, or will you borrow against it? Right. And so look at your own self finance. Do you have enough cash to spend $5,000 in a 90 day period to get 80,000, a hundred thousand bonus points? So self discipline is super important because it's 25% interest rates, you know, compounding monthly. It's too exp, it's too expensive to screw up. So credit is really important, you know, be careful. I think the number one tip is go to one of the publicly traded, go to Equifax, Experian, Transunion. Do a self self assessment check. Don't click on their credit card links because they offer inferior credit cards and they haven't asked you the top four questions. So don't buy from someone who hasn't qualified yet. You so do a self check, look at number of accounts you have open, look at your credit score, any delinquencies you get healthy first because you'll need that to buy a house, you'll need that to buy a car. To get the best rates, you need that stat of bankruptcy. So yeah, look at that. Treat credit as a asset, but treat it seriously and don't get overextended.

[Morgan Lavoy]

Don't go into debt for points.

[Nicole Lapin]

Money Rehab is a production of Money News Network. I'm your host, Nicole Lapin. Money Rehab's executive producer is Morgan Lavoy. Our researcher is Emily Holmes. Do you need some money rehab? And let's be honest, we all do. So email us your money questions moneyrehaboneynewsnetwork.com to potentially have your questions answered on the show or even have a one on one intervention with me. And follow us on Instagram @moneynews and.

[Morgan Lavoy]

TikTok, MoneyNewsNetwork Network for exclusive video content. And lastly, thank you. No, seriously, thank you.

[Nicole Lapin]

Thank you for listening and for investing in yourself, which is the most important.

[Morgan Lavoy]

Investment you can make.