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

Real Estate vs. Stock Market There’s always been a healthy rivalry between real estate enthusiasts and stock market enthusiasts. Real estate investors point to tangible assets, tax advantages, leverage, and control. Stock market investors highlight liquidity, diversification, and ease of management. Each group sees the other as “riskier.” The reality? They’re both right. Both are powerful engines for building wealth, they just follow different paths with different trade-offs.

With the Fed concluding its two day meeting today, I’m reminded of a personal lesson and a broader truth: no one really knows where interest rates will be in six months, a year, or six years from now (despite what the dot plot shows).  My wife and I own a small apartment building in downtown Annapolis, MD. We closed in early July of 2022 right as inflation was surging and the Fed started hiking rates. Remember the word “transitory”?  The Fed attributed the inflation to supply

It’s one of PPW’s five guiding investment principles, yet to many inside and outside the industry, it can feel like a dirty word. “Just buy the index.” “Passive always wins.” “Warren Buffet says most people should just buy the S&P500.” Those approaches can be appropriate if you're self-directed, have limited complexity or don't have access to top quartile managers. But for investors with meaningful assets, tax exposure, and complexity…active management (alongside passive) can

The hardest part of advanced estate planning typically isn’t technical, it’s psychological. Gifting assets to an irrevocable trust means giving up access and control, which is extremely difficult to do even when it’s the right move. That’s why Spousal Lifetime Access Trusts (SLATs) have gained so much traction.  That psychological barrier is easier to cross when your spouse (and indirectly, you) still have access to the assets during their lifetime. Here’s the gist: A SLAT al

"Should I rent it out or sell?" That's the first question I hear when clients upgrade to a new home or move. If they don't already own investment real estate, many are eager to get their first rental property under their belt. Before you jump in, ask yourself: Are you being honest about wanting to be a landlord? Have you truly run the numbers to see if it makes financial sense? And have you factored in the $500k capital gains exclusion? When you move out of your primary resid

Do you ever write a personal check or use a credit card to make a charitable donation? We’re entering the heart of charitable giving season, so make sure your generosity is working as efficiently as possible. When you donate cash, you get a deduction. That’s it. When you donate appreciated securities like stocks, mutual funds, or crypto, you get the same deduction and avoid capital gains tax on the appreciation. One of the most powerful and efficient tools in charitable givin