Will we become obsolete? The one question on everyone's mind in a room full of 200 advisors last Friday. I listened to Michael Kitces and Carl Richards talk about AI and the future of our industry. Their core message was simple: AI won't replace great advisors. It will force us to become better ones. Technology will handle more of the admin and technical work. It will allow us to go deeper with clients, not further away. Carl reminded us that not too long ago, you had to cal

$6M in investable assets But the portfolio hadn’t kept pace. Recently, we began working with a physician in his 40s, married with kids, serial real estate investor and developer. Strong income. Significant real estate equity. His portfolio was built almost entirely with broad-market ETFs, including his bond allocation. There's nothing inherently wrong with ETFs. But as wealth grows and complexity increases, structure and allocation should evolve. Over the past few months, we:

Not everyone needs a therapist. But almost everyone could benefit from having one. The same is true for a good financial advisor. Sometimes you just need someone to say, “That’s a bad idea.”

In a world obsessed with AI, I'm doubling down on handshakes. I use AI every day. It makes me faster, sharper, more efficient. But it doesn’t replace sitting across from someone and hearing or seeing what’s not being said. I’ll still be here. But I’m leaning even further into real conversations. Face-to-face when possible. Where trust is actually built. If you value real conversations, let’s connect.

I cringe every time I hear, “My friend told me I need a trust.” Like it’s some kind of silver bullet. Trust gets thrown around like it’s one thing. It’s not. A revocable trust is about control and simplicity. You still own the assets. You can change it anytime. It helps avoid probate, keep things organized, and plan for incapacity. It does not provide asset protection or reduce estate taxes. An irrevocable trust is about strategy and tradeoffs. You give up control. In return

Happy April 16th. If you know a good CPA, send them a thank you as they re-enter society today. And maybe give them a few days before asking “Quick question on my taxes...”

Delaware Statutory Trusts (DSTs) are coming up more and more in conversations with real estate investors and owners as a way to defer taxes. They’re not new. But the structure, fees, and accessibility have evolved over the past couple decades. For the right investor, a DST can be a very useful tool. Especially for those who are: • Tired of active management • Selling a business and own the underlying real estate • Looking to get off — or at least take a break from — the 1031

The most important lesson I learned during my time at Goldman Sachs: It had nothing to do with investing. I joined Goldman through the 2019 acquisition of United Capital and saw firsthand how powerful a name can be. Yes, the talent is exceptional. Yes, the platform is world-class. But that’s not what clients were buying. They were buying the brand. The institution. There is a different level of gravitas that comes with saying: “Goldman Sachs manages my wealth.” The minimums w

Tax-efficient investing has quietly evolved over the last few decades. Many investors are still using yesterday's tools. The common thread behind this evolution: a growing focus on after-tax outcomes, not just pre-tax performance. Here's how that progression looks: 𝗘𝗧𝗙𝘀: Low cost, broad exposure, tax efficient. A major upgrade from traditional mutual funds. But after long bull markets, they often leave investors with large embedded gains and very little options for tax

Income shows up on a paycheck. Ownership shows up on a balance sheet. It’s no secret ownership can be a powerful wealth building tool. I had my own lightbulb moment several months after starting PPW. I was updating my personal balance sheet and debating whether I should assign any value to the business. “It’s still early.” “I have no plans to sell.” “It’s probably not worth that much yet.” Then I paused and asked myself: If I were advising a client, would I include it on thei

A client came on board last year thinking he was well diversified. Turns out, nearly 30% of his portfolio was concentrated in NVDA and GOOGL. He had no idea. He owned layers of ETFs plus a handful of individual tech stocks that all overlapped. On paper it looked diversified. In reality, he was far more concentrated than he realized. He’s not alone. I see this time and time again with clients who were previously self-directed. Decision fatigue doesn’t just show up in your gr

Most business owners can't accurately answer this question: What is your business actually worth? Some wildly overestimate it. Others quietly undervalue it. For owners who overestimate, it’s because the business is so intertwined with their identity that it's hard to step back and look at it objectively. The number in their head is often based on: - What they've sacrificed and how hard they’ve worked - What their buddy down the street sold his business for - What they need it

“I can’t tell the difference between any of you.” That’s what a successful real estate entrepreneur said to me recently over coffee. Honestly, he has a point. There’s no legal requirement to hold yourself out as a “financial advisor.” Someone with that title may be a wealth manager, financial planner, investment adviser, or simply a broker. Distinguishing between business models is almost as confusing as understanding health insurance. The financial services industry has don

Sometimes the 'wrong' financial decision is the right one. The decision that looks suboptimal on a spreadsheet can be the one that lets you sleep at night. A large part of my job is getting to know people well enough to help them make the right decision for them. I'm reading Morgan Housel's The Art of Spending Money, and this line captures the concept well: "Good advice is never as simple as 'Live for today' or 'Save for the future.' The only good advice is: minimize future r

If you own investment real estate, you already know how valuable depreciation can be. It shelters rental income, boosts cash flow, and makes real estate one of the most tax-efficient wealth-building tools out there. But many investors don’t fully understand what happens when they exit. When you sell, the IRS wants some of those past deductions back in the form of depreciation recapture. It’s typically taxed at 25% of the depreciation allotted over the course of ownership (whe

I pay a small fortune every year on insurance across every category imaginable. Most of it stings. But there’s one premium I never mind paying: Umbrella insurance. It’s one of the most overlooked, economical, high-impact coverages you can buy. Yet it’s often the one people skip. Umbrella insurance is excess liability coverage that sits on top of your core policies (homeowners, auto, boat, renters, etc.). It protects your personal assets from life-altering claims. One bad acc

As of November 18th, 2025, there are over 1,000 individual U.S. stocks that have outperformed Bitcoin this year. Not 10. Not 100. Over 1,000. Bitcoin is often compared to U.S. large-cap stocks like the S&P 500, but from a risk and volatility standpoint, it behaves much more like a single stock than a diversified index. This isn't an indictment of Bitcoin or crypto enthusiasts. Six weeks can be an eternity in crypto—I wouldn't bet against Bitcoin ripping higher from here and s

This past weekend, my family and I continued a tradition that has lasted over five generations. My father was a young kid growing up in Sicily when he started helping crush grapes and make wine on his grandfather’s property. Ever since I can remember, I've been helping my dad make wine. Now, my nephew represents the fifth generation. Some of the equipment we use even dates back to the 1920s. A few years ago when my wife and I moved to a house with the space, we started making

When I was a kid visiting my grandparents during summers and holidays, every Friday morning was spent helping my grandfather deliver donuts to the five local banks he did business with. This was back when bank branches were bustling with people and full of energy—not the quiet, lifeless places many feel like today. He did it because he genuinely loved putting smiles on people’s faces and wanted to show his appreciation. I think, often times, it was his favorite part of the we

A few things I learned after the early stages of fatherhood: · This is way harder than starting a business. It’s also much more fulfilling. · Children are the best productivity and time management hack that exists. · I need 7 hours of sleep. “Powering through” like I used to in my 20s and early 30s doesn’t work so well anymore. A few things I’ve done financially since my daughter was born: · Laddered another life insurance policy · Updated estate & guardianship docs · Opened

There are four potential types of taxes due when selling highly appreciated real estate: depreciation recapture, capital gain, net investment income tax, and state income tax. This often results in approximately 25-40% of your gain going to taxes. Selling outright and paying the tax can often be the right strategy, particularly if you desire maximum liquidity and flexibility. However, if you wish to defer, mitigate, or eliminate some or all taxes at the time of sale, review

I had a prospect several years back who was in his early 40s, healthy and paying close to $2M a year in life insurance premiums. Married, three kids, successful business, but no significant estate tax issue. His “financial advisor” was a friend from high school and worked at an insurance company to remain unnamed. In addition to the life insurance, he had an annuity, a disability policy, and a long-term care policy in place. Outside of some reserve cash, he had nothing inve

Simply put: they help improve risk-adjusted returns. Historically, alternatives—private real estate, private equity, private infrastructure, private credit, venture capital— were reserved for endowments, pension funds, family offices and the ultra-high-net-worth. High minimums, high fees, cumbersome commit-and-call structures, and 7–10 year lockups. Over the past decade, alternatives have undergone a democratization. Today, high-quality institutional alternatives are increasi

We recently helped a client put $500k of idle cash to work without sacrificing flexibility. I hear these reasons all the time for keeping large cash reserves: “We may move in the next few years and I need the cash for a downpayment” “I’m waiting for the market to pullback or crash” “I’m getting burnt out at my job and want flexibility if I need to transition” “I want to invest in real estate” All valid reasons, but many times these scenarios never materialize and the cash sit