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Listen Show PodCast
Inside the Secret World of Ultra-Wealthy Vacations
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283. “We have 3 kids and live paycheck to paycheck. Are we screwed?”
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282. "We spend 154% of what we make. Will we ever stop drowning?"
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281. "We have 4 kids and nearly $1M in debt. Are we screwed?”
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280. "We have $11M in assets. Why are we still living month to month?"
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279. “He lost his $150k job, but I make every decision - can we fix this?”
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278. "We spend 108% of what we make. Are we screwed?"
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277. "He has $100K of debt. Should I still marry him?"
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276. "I resent carrying our finances. Can we fix this?"
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275. "We escaped debt so why are we still spending like this?"
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274. "We have a newborn and 89% of our income is already spent...Now what?"
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273. "We Spend 139% of our Income and still fund our adult kids"
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272. "We own two houses, but can’t afford dinner out"
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271. "He hid $30K of debt a month before our wedding"
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270. “We’re sacrificing our retirement to pay for our kids’ college”
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269. "I want to retire, but my wife is too scared"
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268. "We Make $150K… So why are we broke?"
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267. "She makes 2x more than me. I feel ashamed."
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266. "We’re in our 30s fighting over $1000. Can we fix this?"
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265. "We spend 179% of what we make. Are we screwed?"
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264. "We’re worth $4M. Why is she so terrified to spend?"
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263. "We spend 102% of what we make. Will we ever stop drowning?"
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262. "We make $167k. Why do we feel poor?"
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261. "We’re in our 40s with nothing saved. Will we be ok?"
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260. "We’re in our 40s and forgot to invest. Are we screwed?"
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259. "We’re worth $1.5M but I refuse to buy new pants"
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258. "We had $900K. Now we’re $100K in debt"
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257. "We really want a house - but have $0 in savings"
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256. "We moved abroad for fun. Now we can’t afford to leave"
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255. "I’m 40 and work 2 jobs. How are we still broke?"
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254. My $0 to $100k Playbook (full beginners guide)
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253. "I’m 53, exhausted, and still living paycheck to paycheck"
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252. "I’m 35, in debt, and spend everything I make"
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251. "We own a $1M house but can’t pay for groceries"
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250. "We spend 97% of what we make—and can’t stop"
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249. "We have $2M. Why can’t we enjoy life now?"
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248. "Her spending scares me. Should we get married?"
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247. "We’re in our 40s — with nothing saved"
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246. "We’re drowning in debt, but bought another house"
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245. "We make 6 figures. Why am I hiding fast food purchases?"
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244. "I'm in $244k debt but give $500/mo to my church"
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243. "She inherited $171K…but it’s already gone."
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"Our couples therapist couldn’t fix this. Please help."
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“We invested our wedding money…in psychedelics”
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“We book $10K vacations, then panic about money”
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Listener Favorite: "I'm almost 40 and still living paycheck to paycheck”
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"He quit his high paying job and didn’t tell me"
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"We’re in credit card debt again. Will this ever stop?"
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“We bought our dream house. Then he lost his job.”
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“She spent $5K behind my back. How can I trust her?”
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"Can we pay off this debt faster?" (Part 2)
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"We have $100k+ in debt. Will we ever enjoy life?" (Part 1)
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“I save while she spends on vacations. Is this fair?”
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“My husband gives me an allowance. I feel like a child.”
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“Our $200k in crypto is gone. Now we live with his mom.”
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“We spend 168% of what we make. What are we missing?”
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“I’m almost 50 and have nothing to show for my life”
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“I’m 30, broke, and tired of budgeting”
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“We bought our dream house. Now we’re drowning”
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“She’s chasing FIRE. I want to enjoy life now.”
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“We’re losing $5k/mo. Where is it all going?”
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“I took on debt to help my family. Now she won’t marry me.”
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“We make $81k/yr in our 30s. Is that enough?”
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“My husband is my 4th child. Will he ever help?”
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“I’m almost 40 and still living paycheck to paycheck”
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“I carry the baby, the bills, and the stress”
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“He’s so cheap it’s killing our joy”
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“Our childcare costs are about to quadruple. Are we screwed?” (Part 2)
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“Are we broke…or just bad with money? (Part 1)
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I track every penny. He gambles. Should I marry him?
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“He wants a house, I don’t want to go bankrupt.”
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“I’m 45 but my parents still control my money”
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“We have a $1M trust - but a $30k budget” (Part 1)
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"He's terrified of losing it all—so she's losing him"
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Ramit and Cassandra open up: “Our real money fights (and what we learned)”
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“We make $170k—but spend like we make $450k”
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“We bought a house we can’t afford, now what?”
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“We make $157K at 22, but we’re afraid to spend money”
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“I’m 40, burned out, and don’t know what’s next in my life”
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“I quit my job to care for our son, but can we afford it?”
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“I've been homeless before…I'm terrified to spend money”
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“We make $226K—but our kids think we’re broke”
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“He makes 3x more, but wants to split everything 50/50”
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“She racked up $50K in debt — why should I trust her with money?”
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“I make $40k… but I own 100+ suits”
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“Should we pay off our massive debt? Or invest more?”
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“I struggle w/ cc debt but insisted on a Cartier wedding ring”
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“I work 7 jobs but can’t get ahead. Are we doomed?”
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“I thought he was the problem… but it’s me?!”
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“He used to help me with debt…Now he’s making it worse”
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“Her socks have holes but she's too cheap to buy new ones”
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“$0 savings, $0 investments. Is it too late for us?” (Part 2)
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“I’ve filed for bankruptcy twice. Will I ever stop spending?” (Part 1)
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“We spend 98% of what we make—Where is it all going?”
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“My wife doesn't respect me because she earns 5x more”
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“Is our relationship going to end on air?”
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“People definitely called me out”: Nate & Serena return 2 years later
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“She makes 2x but wants me to treat her” Nate and Serena return
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“We’re worth $87M, Why are we arguing over credit card bills?”
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“Was it a huge mistake to sell our house?”
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