A client of mine signed his second contract a few years back. Walked into my office looser than I'd ever seen him, cracking jokes, already talking about the watch he wanted. His rookie deal had been the kind of money you're almost afraid to touch. This one felt different. This one felt like arrival. I asked him a simple question before we celebrated anything: what does year four look like, when this contract is over, and the phone isn't ringing? He didn't have an answer. Most

Picture a founder two years into building something real. It started at a kitchen table. Now there are actual clients, actual revenue, and a calendar booked out further than they ever imagined. For a long time, that founder was the whole operation. Every email, every deal, every problem, they handled it themselves, because nobody else existed yet to hand it to. For a while, that's not a warning sign. That's just what building something looks like early on. Then the business k

Imagine the day the wire finally hits your account. You have spent a decade or more building your company, grinding through late nights, navigating making payroll, and eventually executing a successful exit. You are likely prepared for the immediate capital gains tax hit. But while you are celebrating the liquidity event, the IRS is waiting for a second cut. Without smart planning, capital gains, estate taxes, and income taxes can swallow 30–50% of your business sale. Most fo

There's a new account with the President's name on it, and every parent asks the same question: is it worth it, or just noise? Part of it is free money. Part of it is a trap if you don't understand the rules. We break down what a Trump Account actually is, how it stacks up against a 529 or UTMA, the Roth conversion opportunity waiting at 18, and the kiddie tax rule that catches almost everyone off guard.

Most founders are great at building. What often gets left behind is the personal financial side. In this guide, Brendan Fraleigh, CFP, breaks down what to do at every stage.

Up to 35% of elite athletes experience a mental health crisis at some point in their career. The pressure, the scrutiny, the identity tied to performance — it adds up. Here is what professional athletes need to know about protecting their mental health, accessing their league benefits, and building a foundation that lasts beyond the game.

Did you know the PGA Tour has a retirement plan for its players? Not only does it have one, it's widely considered the best retirement plan in professional sports. A real example: In the 2024 season, Erik van Rooyen made just 9 cuts on the PGA Tour. Nothing flashy, no wins, no headlines. But because he'd played a full schedule, every one of those made cuts dropped $4,800 into his retirement account. Nine cuts × $4,800 = $43,200, set aside for retirement. Then his season fini

You've maxed out your 401(k). You're still writing a big check to the IRS every April. And nobody has told you there's another option. There's a retirement plan the IRS has allowed for decades that lets you shelter far more than a 401(k) ever could — and deduct every dollar. Most business owners have never heard of it. It's called a Cash Balance Plan.

Brendan Fraleigh, CFP, has spent years inside the world of wealth management for entrepreneurs, close enough to see what works, what doesn't, and what nobody talks about. These are his confessions.

Professional athletes face a financial reality most people never encounter. You earn life-changing money in a compressed window, you carry real risk of injury or sudden incapacity, and you operate in the public eye where privacy is constantly at stake. Those three factors together make estate planning one of the most important financial conversations you can have early in your career, not decades down the road. The right estate planning moves can help protect your family, you

You crossed $2M in revenue. That's not small. That's not starting out. That's a real business. But here's the part no one tells you: the team that got you to $2M can't get you to $10M. Most owners try to scale with the same CPA they hired in year one. The same attorney who set up their LLC. And no real financial advisor at all. Then a tax bill hits. Or an opportunity comes. And they realize, they're underbuilt. In this blog, we'll walk through the 3 core roles every $2M busin

The moment the wire hits your account is rarely the "finish line" founders imagine. Instead, it is the start of a high-stakes transition from an operator to a capital allocator. If you sold your business for $10,000,000 today, the number on the screen would look significantly different than the number on the Letter of Intent (LOI). A $10M business sale typically results in a net liquidity event of $6.8M to $7.2M after taxes and fees. Success depends on aligning your post-exit

Most business owners write a check to charity after they sell. That is the most expensive way to give. A Donor Advised Fund lets you eliminate capital gains, take a large deduction in your highest-income year, and keep giving to the causes you care about for years. This guide breaks down exactly how it works — and the two strategies that make it most powerful.

Brendan Fraleigh, CFP, has spent years inside the world of wealth management for athletes, close enough to see what works, what doesn't, and what nobody talks about. These are his confessions.

Every athlete knows what it feels like to play without a full team behind them. No film session. No position coach. No coordinator calling plays. Just individual talent trying to figure it out alone. That is exactly what most professional athletes are doing with their money. They have people around them. An agent. A CPA. A financial advisor sending quarterly reports. But nobody is in the same room, working off the same game plan, making decisions together. In this blog, I am

A $50M exit doesn't mean a $50M payday. Without planning, a Missouri-based C-corp owner walks away with $35.7M after taxes. With the right strategy in place before the sale? $44.5M. That's $8.8M that didn't go to the IRS, it stayed with the founder. Here's how the math works.

You want to pay for your kid's college. That's clear. What's not always clear is how, or which account you should be putting the money into in the first place. Most parents default to whatever they've heard of first. Sometimes that's a 529. Sometimes it's a custodial account. Sometimes it's just a savings account sitting somewhere earning almost nothing. The problem is the wrong account can cost you tens of thousands of dollars in taxes, financial aid, or both.

Brendan Fraleigh, a Certified Financial Planner, breaks down everything you need to know about the 2026 NBA Pension.

Brendan Fraleigh, a Certified Financial Planner, has the latest on the 2026 NBA Retirement Plan.

Brendan Fraleigh, a Certified Financial Planner, breaks down everything you need to know about the 2026 NFL 401(k).