Most retirees leave hundreds of thousands—or more—on the table. Not just from bad investing. From bad tax planning, wrong Social Security timing, zero distribution strategy, and no protection against sequence of returns risk. If you're 50+ with $500K+ in retirement assets and

Why can't my kids afford a house like I could?" Hear this question weekly from successful Baby Boomer and Gen X clients. Was just quoted in The Guardian on the answer: 1985: First home cost 2x annual income 2025: First home costs 6-7x annual income Both generations

A 65-year-old client called me yesterday, completely out of breath. "Kurt, I just finished my first 5K. I never thought I'd do that." Three years ago, he was working 70-hour weeks, stressed, convinced he couldn't retire because "the business needs me." We ran the numbers. He

Link to JPM study.

61 years old snd married. $1.3M saved. Partially retired. Just fired his advisor. "Six months ago I felt like I could finally spend a little." "Now I have $30K in credit card debt I didn't have before." "How did this happen? I've been careful my whole life." JP Morgan

Peter Thiel turned $2,000 into $5 billion tax-free using a Roth IRA. Here's the strategy—and why it matters for you: What Thiel did: 1999: Put $2,000 in a Roth IRA, bought PayPal founder shares at $0.001 2002: PayPal sold, rolled millions tax-free into early Facebook

My client has $520,000 in unrealized capital gains. He's 74. If he sells now: 15% capital gains tax = $78,000 If he holds until death: His heirs get step-up in basis = $0 tax The answer? Hold it. Let them inherit it tax-free.

I ask every new client: "What does a successful retirement look like?" Most can't answer. They saved for 40 years without defining success. One said: "I just want enough." Enough for what? Travel? Hobbies? Helping kids? Healthcare? Retirement planning isn't just hitting a

The difference between good and great retirements? Flexibility. Retiree A: $2.7M (all in IRA) Can't access without taxes RMDs are mandatory No flexibility Retiree B: $2.7M (split between Roth, taxable brokerage, IRA) Tax-free options Control over income Flexibility Same

A client asked: "Should I convert my entire IRA to Roth?" No. "Why not?" Because you'd pay 32-37% to convert. Then have zero traditional IRA money. Which means you can't use your 10-12% tax brackets in retirement. Goal isn't always zero taxes. It's OPTIMAL taxes.

In the last 25 years working with 1000s of people on their retirement. I see the same regret every day: "I wish I'd started earlier." So here's how I'm personally using Christmas to build generational wealth instead of buying gifts that will be worthless in a few years. And

The most overlooked retirement risk? Cognitive decline. A client asked: "What happens if I can't manage my finances anymore?" Do you have: Durable power of attorney? Revocable living trust? Successor trustee named? Simplified accounts? Most don't. Your plan must work even

A client said: "I don't want to think about dying." I get it. But I asked: "Do you want your spouse scrambling to figure out your finances after you're gone?" That changed his tone. Planning for death isn't morbid. It's the final act of love. We updated everything:

"I just lit $47,000 on fire because nobody would give me a straight f***ing answer." That's how a guy opened our first meeting. He had $2.1M sitting in a pretax 401(k). For 3 YEARS he'd been asking what to do about it. His big money management firm advisor: "That's a tax

A couple said: "We're living on Social Security and RMDs." "Are you happy?" "No. We feel broke." They have $2.9M in IRAs. But poor planning made them cash-flow poor: RMDs: $109,000 → After tax: $82,000 Social Security: $52,000 → Taxable: $44,000 Spendable: $126,000/year

The most common regret I hear? "I wish I'd retired sooner." Not "I wish I'd saved more." Not "I wish I'd worked longer." But: "I waited too long." A client worked until 68. His wife got sick at 70. They never took the trip to Italy. Time is the only asset you can't replace.

A couple said: "We don't want to burden our kids." Noble goal. Then I asked: "Do you have a plan for your long term medical care?" No. "Updated estate documents?" From 2003. "Powers of attorney?" Somewhere. Not being a burden requires planning. Good intentions + no plan =

A 59-year-old asked: "Why does everyone keep pushing Roth conversions?" Because: Tax rates are at historic lows Your RMDs will spike your income Your heirs inherit tax-free money It reduces lifetime IRMAA penalties The conversion window closes at 73. After RMDs start, it's

A 67-year-old said: "I'm not worried about inflation. I live simply." Then I showed him healthcare inflation: Today's costs: $6,200/year In 15 years at 6% inflation: $14,850/year His income is fixed. His costs are not. Inflation doesn't care how simply you live.

Client's 58. Planning to retire at 60 with $2.2M saved. Has a $215K mortgage at 3.1%. Payment is $1,390/month. Wants to pay it off before he retires. "I don't want any debt in retirement." Twenty years ago, I would have fought him on this. Pulled up spreadsheets. Run Monte

A client asked: "When should I start withdrawing from my Roth?" I said: "Never, if possible." He was stunned. "But I saved it for retirement!" Yes. But your Roth is your: Tax-free emergency fund Inheritance for heirs (tax-free) IRMAA management tool RMD shield Hedge if tax