Speaker
Dr. John Delony
Appearances over time
1 episodes
Episodes
1
Podcasts
Quotes & moments
When you inherit a capital asset — stock, farm, real estate — your tax basis steps up to the market value at the time of death. Sell it shortly after inheriting and you could owe zero capital gains. The IRS resets the clock when you receive the inheritance.
A widow secretly spent $1.1 million on cruise ship auction art across six to seven voyages after her husband died. Her sons are getting back just 10–20 cents on the dollar — and Dave's advice is to go straight to the cruise line's PR department and ask for a buyback.
Dave's strategy for the cruise ship art situation is PR leverage, not litigation. Tell the cruise line: a widow spent $1 million on your ships and we're not saying you meant harm — but this happened on your watch. Buy it back, resell it, make your money. Or we go to social media.
A family earning $100,000 a year with no debt can't save a dollar for retirement — because $25,000 goes to private school tuition. The spending isn't wrong, but it's a choice. And choosing private school means simultaneously choosing to have no retirement savings. Own that.
An unmarried woman paid off $15,000 of her boyfriend's debt while living in his mother's beach house and paying the mortgage. If he walks, she gets nothing. Dave's warning is stark: you are legally and relationally exposed in a way most cohabiting couples refuse to see.
Dave's college roommate Jeff is still a friend 40 years later. But Dave never paid a dollar of Jeff's debt. That's the rule. Unmarried people sharing finances are roommates — not spouses — and treating each other like spouses financially creates devastating exposure.
Dave watched a 70-year-old retiree lose $700,000 in three months because she had 100% of her 401(k) in company stock. Dr. Delony knew Enron employees who woke up with nothing. A semiconductor stock tripling in three months is thrilling — and irrelevant. Sell it.
Dave doesn't hate all annuities. Variable annuities in isolation are decent — mutual funds in a tax-deferred wrapper. But the moment they're bundled with long-term care or sold by a life insurance agent calling themselves a fiduciary, run. They're paying double fees for false guarantees.
Dave's startup rule for Derek's veterinary clinic: it will take twice as long and cost twice as much as planned. Buy slightly used equipment from the last vet who went broke. 'Minimal functional' is the mantra. You can launch for $150K if you resist the shiny new gear.
Maria has been fired from nine engineering jobs since 2017, not because she lacks the degree — she has a master's — but because she can't stay calm under pressure. Dave's prescription: make therapy tactical. Role-play the hard scenarios. Practice keeping your cool before you lose another job.
A Silicon Valley couple earning $750,000 was considering Airbnbs for tax advantages. Dave's verdict: the only short-term rentals that create tax benefits are losing ones. And if you want to lose money, just give it to charity — same write-off, none of the midnight sheet changes.
Hugh lost his wife Summer six months ago after 20 years of marriage and called to ask if he'd lost the 'marriage advantage.' Dave's answer: the advantage is a long-run statistical average, not a switch that flips off. And you've already built 20 years of it. Keep living that way.
Medicaid nursing homes are welfare — and like all welfare-funded services, the experience differs meaningfully from private pay. Dave's advice: use the house proceeds to buy private care for your mother rather than qualifying for Medicaid. She has $250,000. Use it.
Matthew's wife bought their home with $500,000 of her inheritance and now wants a divorce. Legally, she may be owed more. Morally, Dave says: return her $500K, split the appreciation equally, leave each other's retirement accounts alone, and call it done.
A couple earning $140,000 a year is still carrying a $3,500 debt to her parents for going over the wedding budget — a deal the wife made without telling her husband. Dave's answer: write the check today. And make a new rule — no money deals with your parents, ever.
Analysis
What they talk about
- Society & Culture 67%
- Business 33%
Connections
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