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The letter of intent lands in your inbox. Fifteen million dollars. You read the number three times. Then you start doing the math you've been doing in your head for a decade. The house paid off. The kids' college. Maybe a boat, maybe not. Maybe you finally stop answering the phone at 9pm. Here's the problem. The number in the LOI is the price of the business. It is not the amount that reaches your bank account. And the gap between those two numbers is determined far more by how the deal is structured than by what the buyer agrees to pay. Most owners spend two years negotiating the price and two weeks thinking about the structure. It should be the other way around. Here's what a $15 million offer actually turns into. Understanding a $15M Deal: Immediate Cash, Escrow, Earnouts, and Seller Notes Explained. 1. The Headline Number Is Not the Wire Number Start with the simplest version of the math: a stock sale, very low cost basis, and no complications. Real deals are never this clean, but it shows the shape of the problem. Headline sale price $15,000,000 Less transaction costs (banker, legal, accounting, ~3%) ($450,000) Less federal capital gains tax (20%) ($2,910,000) Less state tax (~5%) ($727,500) Approximate net to you ~$10,900,000 That's illustrative, not a projection. Your state, your basis, and your structure will move it. Two other things can move it too. A 3.8% net investment income tax can apply on top for some sellers, though owners who actively run the business often avoid it. And if the deal is an asset sale, part of your proceeds may be taxed as ordinary income at rates well above 20%. A $15 million sale becomes roughly a $10.9 million outcome before you've spent a dollar. That's still a life-changing result. It's just a different number than the one you've been picturing. 2. Stock Sale vs. Asset Sale Is the Biggest Lever Nobody Explains When someone buys your company, they either buy your stock (the ownership of the entity) or your assets (the equipment, contracts, customer lists, and goodwill inside it). Sellers generally prefer a stock sale because most of the proceeds are taxed as long-term capital gains. Buyers generally prefer an asset sale because they get a stepped-up basis and can depreciate what they bought. That tension is where the negotiation lives. If the buyer pushes for an asset deal, some of your proceeds can be reclassified as ordinary income, such as depreciation recapture and certain inventory or receivables. The difference can be hundreds of thousands of dollars. The point isn't that one structure is always right. It's that the structure is a price term, and you should negotiate it like one. A buyer asking for an asset deal is asking you for something. Ask for something in return. 3. QSBS Could Be Worth Millions, If You Qualify If your company is a C corporation and you received your stock at original issuance, you may be sitting on one of the most valuable tax provisions in the code: Qualified Small Business Stock under Section 1202. For stock that qualifies, a large portion of the gain, up to a cap, can be excluded from federal tax entirely. The rules changed in 2025 for newer stock, including a tiered holding period and a higher cap, and they differ for stock issued before and after the change. The catch is that qualification depends on details: the type of business, the size of the company's assets when the stock was issued, how long you held the shares, and how the stock was acquired. Many owners find out they qualified only after the deal closes, which is too late to do anything about it. If you're a C corp founder, have someone check this before you sign the LOI. 4. You Rarely Get Paid Everything on Day One The headline price usually isn't the closing-day wire. Expect some combination of: Escrow or holdback. Often 5% to 15% of the price is held back for 12 to 24 months to cover indemnification claims. Earnouts. A portion of the price is contingent on the business hitting future targets, under someone else's ownership. Seller notes. The buyer pays part of the price over time, with interest. Rollover equity. You reinvest part of your proceeds into the buyer's new entity, often tax-deferred. Each of these changes your tax picture, your timeline, and your risk. A $15 million deal with $3 million tied up in an earnout is not the same as a $15 million deal paid in cash at closing, even if the LOI says the same number. When you plan your life around this money, plan around the cash you can count on, not the total on the page. We have talked about this topic before on why selling at $10mil might be better than $40mil. 5. Your State Matters More Than You Think Two sellers with identical deals can end up hundreds of thousands of dollars apart because of where they live. Some states tax capital gains at zero. Others take 10% or more. That's a seven-figure swing on a deal this size. It's tempting to think about moving before you sell. It can work, but states look hard at moves made right before a big liquidity event, and a real change of residency means a real change of life: where you live, where you vote, where your family is, how you spend your days. A move on paper that doesn't match reality tends to get challenged. If it's something you're considering, it's a conversation to have with a tax professional well before the deal, not after. 6. The Best Planning Happens Before the LOI Here's the uncomfortable truth about selling a business: most of your best tax planning options expire the moment the deal becomes a binding agreement. Strategies like gifting shares to trusts, setting up a donor-advised fund, or restructuring ownership generally need to happen while the business is still just a business, not a pending sale. Once a buyer is under contract, the IRS can look through transfers made right before closing and tax them back to you. That means the window for the planning that matters most is often 18 to 36 months before you sell. For more on how trusts fit into this, see What Actually Decides If You Need A Trust? 7. Plan for What Comes After The other side of a sale is the question we covered in our last post: what does the money actually need to do for the rest of your life? A sale is a one-time event that has to fund decades of living. How much you keep matters, but so does what happens next: the withdrawal rate, health insurance, access to your retirement accounts, and the order of returns in the early years. You can read the full breakdown in You Sold Your Business at 40. Here's What It Actually Costs to Never Work Again. And if you want to see what a portfolio built from a clean slate looks like: $10mil Portfolio from Scratch Final Thought The price is what the buyer pays. The structure is what you keep. Most owners put all their energy into the first and almost none into the second. The ones who come out ahead treat the structure, the timing, and the tax plan as part of the negotiation, not an afterthought for the accountant to clean up once the papers are signed. They start early. They ask what's negotiable besides the price. And they decide what the money is for before the money arrives. If the deal closed next quarter, do you know how much of the headline number would actually reach your account, and when? If you're a business owner thinking about a sale, please schedule a call, and talk with a Moment founder. Get in Touch With An Advisor SCHEDULE A CALL WITH MOMENT Frequently Asked Questions Here are some answers to questions I received frequently about this topic. How much tax will I pay when I sell my business? It depends on the structure of the deal, your cost basis, your state, and whether any of the gain is taxed as ordinary income. For a straightforward stock sale, federal long-term capital gains tax is 20%, plus state tax and possibly a 3.8% net investment income tax. Asset sales can result in higher blended rates. Is a stock sale or an asset sale better for the seller? Generally, sellers prefer stock sales because more of the proceeds are taxed at capital gains rates. Buyers often prefer asset sales for the tax benefits they receive. The right answer depends on the specifics of the deal and what you can negotiate in exchange. What is QSBS and could it apply to me? Qualified Small Business Stock (Section 1202) allows eligible shareholders of certain C corporations to exclude a portion of their gain from federal tax, up to a limit. Eligibility depends on the business type, company size at issuance, holding period, and how the stock was acquired. What is an earnout? An earnout is a portion of the purchase price that's paid only if the business hits certain targets after the sale. It can bridge a valuation gap but shifts risk to you, since you're relying on performance you may no longer control. When should I start planning to sell my business? Ideally two to three years before the sale. Many tax and estate planning strategies need to be in place before a buyer is under contract, and cleaning up financials, ownership, and structure takes time. Can I reduce taxes by moving to another state before I sell? Possibly, but states scrutinize residency changes made right before a large sale. A move needs to be real and well documented, and it should be reviewed with a tax professional well in advance. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

Jen and Maria sit two desks apart at the same Missouri brokerage. This year, each of them netted $500,000. Jen paid $188,071 in taxes. Maria paid $124,955. That's a $63,116 difference, in one year, between two agents who sold about the same and live in the same state. The only real difference is that Maria planned and Jen didn't. As financial advisors for business owners, we help real estate agents set up their business so they keep more of what they earn. Meet Jen and Maria Both agents are single and live in Missouri. Each has $500,000 of net profit. Jen does no planning. Her brokerage sends a 1099 in her name. She files a Schedule C, pays what the return says, and gets back to work. No retirement plan. No elections. No strategy. Maria planned all of it. She set up an LLC taxed as an S corporation, pays herself a reasonable salary, maxes out what her plan allows in a Solo 401(k), elects Missouri's PTET, funds an HSA, and runs an accountable plan for her home office and phone. Here's how each move adds up. Move 1: The S Corp Worth to Maria: about $36,200 this year This one move does two big jobs at once. It cuts Maria's payroll tax, and it unlocks her QBI deduction. Payroll tax When you're self-employed, you pay self-employment tax. That's Social Security and Medicare, and you pay both the "employee" half and the "employer" half yourself. For 2026, Social Security tax is 12.4% on your first $184,500 of self-employment earnings. Medicare is 2.9% on everything, with no cap. Once a single filer passes $200,000, there's an extra 0.9% Medicare tax on top. Here's Jen's bill on $500,000: Self-employment tax: $36,269 Additional Medicare tax: $2,356 Total: $38,625 Maria's S corp works differently. She pays herself a $125,000 salary. Payroll tax only hits the salary. The rest of the profit comes to her as a distribution, and distributions don't carry Social Security or Medicare tax. Payroll tax on Maria's salary, counting both halves, is $19,125. That's about $19,500 less than Jen. Want to go deeper on picking the right business structure? Watch our video on business structure here. The QBI deduction The Qualified Business Income (QBI) deduction lets business owners deduct up to 20% of their business profit. The One Big Beautiful Bill Act, signed July 4, 2025, made it permanent. Some professions lose QBI at high incomes. Doctors, lawyers, accountants, and financial advisors are on that list. Real estate agents and brokers are not. The IRS regulations carve you out by name. But there's a trap door. Once your taxable income passes a certain point, your QBI deduction is capped at 50% of the W-2 wages your business pays. For single filers in 2026, that cap phases in between $201,750 and $276,750 of taxable income. Jen's taxable income is about $454,000. She's way past the line. And as a sole proprietor with no payroll, she pays zero W-2 wages. Half of zero is zero. Jen's QBI deduction: $0. She didn't forget to claim it. At her income, with no payroll, the rules give her nothing. Maria's company pays her a $125,000 W-2 salary. Half of that is $62,500, which sits right around 20% of her business profit. So the cap barely touches her. Maria's QBI deduction: $62,201. In the 35% bracket, that's worth more than $21,000 in federal tax. The same salary that cuts Maria's payroll tax is what unlocks her QBI. That's why the S corp is worth so much more to a single agent at this income than people expect. The catch: the salary has to be real You can't pay yourself $30,000 and take $470,000 as distributions. Your salary has to be reasonable, meaning close to what you'd have to pay someone else to do your job. There's a well-known case on this from the 8th Circuit, which covers Missouri. An Iowa CPA named David Watson ran his practice as an S corp and paid himself a $24,000 salary while taking far more out as distributions. The IRS said about $91,000 was reasonable. The court sided with the IRS. Maria's $125,000 is an example. Your number should be backed by real data on what agents and sales managers earn in your market. Write down how you picked it. If the IRS ever asks, you want a file ready. Move 2: The Solo 401(k) Worth to Maria: about $21,200 this year. If you're self-employed with no full-time employees, a Solo 401(k) is usually the strongest retirement plan you can have. It has two parts: Employee deferral: up to $24,500 in 2026. Age 50 or older, add $8,000. Age 60 to 63, add $11,250 instead. Employer contribution: up to 25% of your W-2 salary in an S corp. The total can't go over $72,000 in 2026, plus any catch-up. Maria puts in $24,500 plus 25% of her $125,000 salary. That's $55,750, all deductible because she uses the traditional side. Jen put in $0. Three things to know: In an S corp, your deferral has to come out of a paycheck. December 31 is the real deadline for that piece. You can't decide in April. Age 50+ with a big salary? Starting in 2026, if your prior-year FICA wages were over $150,000, your catch-up contributions have to go in as Roth. Hiring changes things. Add an employee who qualifies for the plan, and a Solo 401(k) may no longer fit. Move 3: PTET Worth to Maria: about $2,200 this year Missouri's SALT Parity Act, better known as PTET (pass-through entity tax), lets an S corp elect to pay Missouri income tax at the company level. The rate is the top individual rate, which is 4.7% for 2026. Tax the company pays is deducted before the profit reaches your personal return. You get a Missouri credit for your share, so you don't pay the state twice. Maria's company pays about $15,300 through PTET. At $500,000, Maria isn't hitting the federal SALT cap, which is $40,400 in 2026 and only starts shrinking once income passes $505,000. So PTET helps her in a quieter way. Without it, her state and property taxes add up to about $25,000 of itemized deductions. With PTET, most of her state tax is deducted at the company level. What's left is small enough that she takes the $16,100 standard deduction on top. PTET gets much more powerful once income passes about $606,000, when the SALT cap drops back to $10,000. You have to elect it every year on Form MO-PTE. Once you elect for a year, you can't undo it. Move 4: The HSA Worth to Maria: about $1,750 this year. Maria carries a high-deductible health plan, which lets her fund a Health Savings Account. For 2026, the limit is $4,400 for self-only coverage. The money goes in tax-deductible, grows tax-free, and comes out tax-free for medical costs. That triple benefit is rare in the tax code. Most agents treat the HSA like a checking account for doctor bills. Maria invests hers and pays small medical bills out of pocket, so the account keeps growing. Move 5: The Accountable Plan Worth to Maria: about $1,700 this year. Maria works from a home office and runs her business off her cell phone. Her S corp has a written accountable plan, so the company reimburses her for the business share of those costs. In our example that's $4,800 a year: $3,600 for the home office and $1,200 for her phone. The company deducts it. Maria doesn't pay tax on the reimbursement. She just needs receipts and a written plan. The Scoreboard Jen (No Planning) Maria (Full Planning) Federal income tax $127,717 $83,851 Payroll / self-employment tax $38,625 $19,125 Missouri income tax $21,729 $18,937 Extra S corp costs (payroll, tax prep) $0 $3,000 Total tax and costs $188,071 $124,955 QBI deduction $0 $62,201 Saved in a 401(k) $0 $55,750 Saved in an HSA $0 $4,400 Maria keeps about $63,000 more this year. She also ends the year with $60,150 set aside in tax-advantaged accounts. Jen has nothing set aside. If those numbers repeat for ten years, Maria's tax savings pass $630,000. That's before counting what her 401(k) and HSA grow into. The dollar value of each move depends on the order you stack them in. We added them in the order shown above. Even More Maria Could Do These weren't in our math, but they belong on your list. Your car. For 2026, the IRS mileage rate is 72.5 cents a mile for January through June and 76 cents a mile from July 1 on. The IRS raised it mid-year because of gas prices, so split your log at July 1. An SUV or truck rated over 6,000 pounds gross vehicle weight can qualify for 100% bonus depreciation in the first year if you bought it after January 19, 2025 and use it for business more than half the time. Drop below 50% business use later and some of that deduction comes back. Keep a mileage log either way. Health insurance through the S corp. If you own more than 2% of an S corp, the company can pay your health premiums. They show up on your W-2 but aren't hit with Social Security or Medicare tax, and you deduct them on your personal return. Hiring your kids. If you have children who do real work, you can pay them a fair wage. A child can earn up to $16,100 in 2026 with no federal income tax, and that income lets them fund a Roth IRA. In an S corp, their wages do owe Social Security and Medicare tax. Estimated taxes. If your income last year was over $150,000, pay at least 110% of last year's total tax during this year to avoid penalties. S corp owners have an extra tool: federal tax withheld from a paycheck counts as if it were paid evenly all year, even if most of it comes out in December. A cash balance plan. For agents in their 50s and 60s with steady income, a cash balance plan can sit next to a 401(k) and allow six-figure deductions each year. It comes with a real funding commitment. Your Next Step If you are a real estate agent or in a similar sales role and this sounds like you. Schedule a call with our team, and we'll show you which of these moves fit your family. Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I receive frequently about this topic. Are real estate agents a "specified service" business for QBI? No. The IRS regulations specifically say brokerage services do not include real estate agents and brokers. Agents can keep the QBI deduction at high incomes as long as the W-2 wage limit is met. What salary should I pay myself? It should match what you'd pay someone else to do your work, and you should document how you got there. Going too low is the fastest way to invite an IRS problem. Isn't an LLC enough on its own? No. Without the S corp election, you're taxed like Jen. How do you work with other members of my team? We believe in the power of the team. For most of our clients, their team consists of Moment Private Wealth, an accountant, an attorney, a banker, and an insurance specialist. We help our clients build out their team of individuals or work with existing partners that clients have. Our goal is to ensure every family has a team of experts to protect their interests. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

I have spent years sitting across the table from entrepreneurs and business owners. Having served one of the largest tech entrepreneurs in the world, to business owners just starting out, it's evident that the size of the business changes, but the blind spots don't. Here's what I've noticed working with owners at your stage. You'll fire your CPA if the numbers keep coming back wrong. You'll switch attorneys, switch vendors, rebuild your whole leadership team if it isn't working. But the person managing your money? For most owners, that's the one relationship nobody ever circles back to, no matter how much the business has changed since it started. In today's blog, I want to walk through why that happens, and the signs that tell you it's time for a real conversation with your wealth advisor as a business owner. The Silent Signs You've Outgrown Your Wealth Advisor as a Business Owner Why This Relationship Never Gets a Second Look Everything else in your business comes with a built-in reason to reassess it. Think about it. If you have a bad quarter, a vendor drops the ball or a hire isn't working out, you look to make a change...and quickly. Your wealth advisor relationship doesn't work like that. Typically there is no red flags or missed deadlines to point to. Just a statement in the mail, a call once or twice a year, and the quiet assumption that no news is good news. Let me tell you, that is not true. Because "nothing feels wrong" and "this is actually as good as it could be" are two very different things, and most owners have never had a reason to find out which one is true for them. The Advisor Who Got You Here Was Solving a Different Problem Do me a favor. Think back to who you hired, and when. Maybe your CPA made the introduction. Maybe it was someone from your local business network. Maybe it was whoever was in front of you the first time your business actually made real money and you needed help figuring out what to do with it. That person was solving a young business owner's problem: First meaningful profit A basic retirement account Simple, foundational questions Get the fundamentals in place You're not running that business anymore. Your revenue's grown. Your balance sheet has layers it didn't used to have. And here's the reality: This is the point in your business where the plan matters more than it ever has. You need to start thinking seriously about what this business, and your life, looks like once you're no longer the one running it day to day. That's not always an easy thing to sit with. So the real question isn't whether your advisor did a good job in year one. It's whether that relationship has kept pace with everything else in your business. The Signs Worth Paying Attention To Here are the ones I see most often go unnoticed by business owners: You can't explain your own plan if someone asked you to. It may sound silly, but when I sit down with business owners, I usually start the conversation with, "Tell me a little bit about your personal finances outside of the business." Typically I will get answer like, "Hmm that's a really good question" and then a pause... You need to understand the following: What happens to this business if I decide to walk away? Where does my income come from once I'm not running it? What happens to my family if I'm not here? If I want to start another company, does my plan account for that? These are different questions than the ones you started with. And they're questions that should have been answered a long time ago. Every meeting sounds identical, no matter what's changed in your business. If your advisor is handing you the same performance summary year after year, that's a problem. At your stage, they should be reviewing everything with a dollar sign attached to it: Cash Flow Tax Exposure Estate Plan Entity Structure Risk Management Documents That review should happen at least once a year, without you having to ask for it. Nobody has asked you a real question about your business, only about your money. You'll be living off this company, or what it becomes, far longer than you'll be actively running it. Has your advisor ever asked: How much longer do you actually plan to run this thing? What happens if you have to step back sooner than planned? Could your lifestyle survive without the business cutting you a check every month? None of these are investment questions. But these questions matter far more when it comes to your personal financial life. You find out about big moves after they've already happened. I hear this constantly from new clients describing their old advisor. "He came in, used a bunch of terms I didn’t recognize, and told me it was all handled.” That's a problem. You don't need to be the expert. But you should understand your plan and why it's built the way it is. If you can't, it's worth getting a second set of eyes on it. You've never once heard “that's not the right move for you.” I believe in real relationships, and real relationships include someone willing to push back. Think about the people you trust most in your life. I'd bet every one of them will tell you something you don't want to hear when it matters. If your advisor never does that, they're managing your comfort, not your outcome. Nobody has ever brought up your exit before you did. When we start working with an owner, this is one of the first things we talk about. Every business eventually gets sold, handed off, or shut down. If you've been running yours for years and no one has asked what you want that moment to look like, they're thinking in the short-term, not the long-term. Loytalty Isn't the Same as Fit I am as loyal as it comes. But as a business owner, sometimes you have to make the decisions that feel uncomfortable. You obviously know that, otherwise you wouldn't be in the position you are in. Leaving a financial advisor, no matter how long they have been with you, is not disloyal if they are not meeting you where they need to. Yes, this person may have been with you from the beginning. And brining in a second opinion may feel like you are turning your back on them. But being loyal to a person and being well-served at your current stage are two separate things. Mixing them up is exactly what keeps owners stuck with something that stopped fitting years ago. Nobody blinks at getting a second opinion on a big lease, a key hire, or a major acquisition. Your financial future deserves at least that much scrutiny, especially now. What a Real Second Opinion Actually Looks Like A good advisor isn't trying to poach you from a relationship that's working. At least they shouldn't be. But a good advisor will ask a few honest questions and see how the answers land. Can your current advisor clearly explain what your plan is actually built around? Do they understand your industry, your business structure, and your realistic exit timeline? Have they ever told you no? Do they actually know what you want your life to look like once you've stepped away from the business? If those answers come easily, that's reassuring. If they don't, or if you realize you've never actually asked, that's a problem. Final Thought The owners who come out the other side of their businesses in the best position are one's willing to ask their financial advisor the hard questions. They're the ones who never let an important relationship coast just because it was familiar, especially the one holding their financial life together. You wouldn't run your business today the way you ran it in year one. You wouldn't keep taking advice from a mentor who never adjusted to who you've become. Your financial plan deserves that same standard. If it's been a while since you've actually put that relationship to the test, now's the time. If you're at this stage in your business and want a second opinion, schedule a call with a Moment Founder. Not sure what questions to ask, check out this video on 10 questions you should ask when interviewing a financial advisor. Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I receive frequently from business owners. How do I know if it's time to get a second opinion on my financial advisor? If you can't clearly explain your own plan, if every conversation feels the same regardless of what's changed in your career, or if post-career planning has never come up, those are all signs worth paying attention to. Isn't switching financial advisors disruptive? Not when it's done right. A good second opinion starts with a conversation. You are simply gathering information, not blowing anything up. How is Moment Private Wealth different from a typical financial advisor? We work specifically with athletes and business owners, which means we understand entity structures, exit timing, and succession planning in a way a generalist advisor typically doesn't. We also have the firepower to deliver for you as a business owner. What does your average client look like? Our clients are nearly all athletes and business owners. Our average client has a net worth greater than $5M. The strategies, solutions, and planning that we implement have a high-net-worth and ultra-high-net-worth client in mind. Why should I consider hiring Moment Private Wealth? Great question! But first, let us explain why you shouldn’t hire us. If you’re looking for an advisor who will pitch shiny object investments or be a “yes man” you are in the wrong place. Why? Because we believe in being truth tellers and only giving advice that we take ourselves. The investments, strategies, and planning we do are all things our advisors do with their own money. If you are an athlete or business owner interested in things like lowering your tax bill, investing smarter, and finding a trusted partner we might be a good fit. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

The wire hit. Ten million dollars, net of taxes and fees, sitting in an account with your name on it. Everyone tells you the same thing. You're set. You never have to work again. And they're probably right. But not for the reason they think, and not by nearly the margin they imagine. Here's the problem. Every rule of thumb you've ever absorbed about retirement, the 4% rule, the 25x number, the glide path into bonds, was built for a person who stops working at 65 and needs the money to last 30 years. You're 40. You need it to last 50. That's not the same math with a bigger number in front of it. It's a different problem entirely. Three things break at once when you retire at 40: the withdrawal math, the health insurance, and the access to your own money. Here's what $10 million actually looks like when you have to live on it for half a century. Stop Working at 40, now what? 1. Your Withdrawal Rate Isn't 4% The 4% rule came out of research on 30-year retirements. Stretch that to 50 years and the math stops cooperating. Most work on longer horizons lands somewhere between 3% and 3.5% as a starting withdrawal rate. On $10 million, that's $325,000 a year. Not $400,000. And that $325,000 is the gross number — before taxes, before health insurance, before anything. The difference between 4% and 3.25% doesn't feel like much on paper. Over 50 years it's the difference between a plan that works and a plan that runs out when you're 78 and unemployable. 2. Where the Money Lives Decides What You Keep Fresh sale proceeds have a quirk that works in your favor early and against you later. The $10 million you just invested has a cost basis of roughly $10 million. Sell some in year two to fund your life and most of what you're pulling out is your own principal coming back. Very little tax. Fast forward fifteen years. That same account has doubled. Now every dollar you sell is heavily embedded gain, and the tax bill on the same lifestyle is multiples of what it was. There's a second piece people miss entirely. A $10 million portfolio throws off dividends and interest whether you want it to or not — call it $150,000 to $200,000 a year of taxable income you didn't choose to create and can't turn off. You pay tax on that even in a year you spend nothing. Between investment income and realized gains, a household in this position is often looking at $40,000 to $50,000 a year in tax on a $325,000 withdrawal. Your mileage varies with your state, your basis, and how the portfolio is built. 3. You Have 25 Years Before Medicare This is the line item that wrecks more early retirement plans than bad investing. You're 40. Medicare starts at 65. That's 25 years of buying your own health coverage for a family — and at this income level you're paying full freight on the open market, not a subsidized rate. Budget roughly $36,000 a year for a family plan, all in with deductibles and out-of-pocket. Then assume it grows faster than everything else in your plan, because it historically has. Over 25 years, that's a seven-figure line item. Most people planning an early exit treat health insurance as a footnote. It is not a footnote. It's one of the three largest expenses of your entire retirement. 4. So What Does $10 Million Actually Buy? Let's put the three together. Initial withdrawal (3.25%) $325,000 Less estimated tax ($45,000) Less health coverage ($36,000) Available for actual life ~$245,000 That's illustrative, not a projection. Your numbers will move. But sit with it for a second. Ten million dollars, and you're living on about $245,000 a year. That is a genuinely good life. It is not an unlimited one. And the gap between those two things is where people get into trouble, because they budgeted for the first number and started spending like the second. We have talked about this topic before on why selling at $10mil might be better than $40mil. 5. Half Your Money May Be Locked Until You're 59½ Here's the one nobody warns you about. If a meaningful chunk of your wealth sits in a 401(k), SEP, or profit-sharing plan from the business, that money is behind a wall until age 59½. At 40, that's nearly two decades of waiting, during exactly the stretch when you have zero earned income and need the cash. The Rule of 55 doesn't help you. It requires separating from service in or after the year you turn 55. You left at 40. There are three real bridges: The taxable account. The simplest answer. Sale proceeds in a brokerage account have no age restriction. This is why how you allocate between account types after a sale matters more than most people realize. A 72(t) / SEPP schedule. Substantially equal periodic payments let you tap a retirement account early without penalty. The catch is rigidity, once you start, you're locked into the schedule for five years or until 59½, whichever is longer. Break it and the penalties come back retroactively. A Roth conversion ladder. This is the underrated one. The years right after a sale are often the lowest-income years of your adult life. Low income means cheap conversions. Convert a slice of the pre-tax account to Roth each year at a low rate, and each converted amount becomes accessible five years later. Done deliberately, you build a staircase out of the locked account and lower your lifetime tax bill at the same time. Done accidentally, you waste the lowest-tax decade you'll ever have. 6. The First Five Years Decide Everything Two people retire with identical portfolios and earn the identical average return over 30 years. One runs out of money. One dies with more than they started with. The only difference is the order the returns arrived in. That's sequence-of-returns risk, and it's brutal for early retirees because you're selling shares to live on. A 30% drawdown in year three, funded by selling into the decline, permanently removes shares that would have recovered. You don't get them back. The structural answer is to never be a forced seller: Two to three years of spending held in cash and Treasuries The next five to seven years held in high-quality bonds Everything beyond that in equities When the market drops 25%, you spend from the first two buckets and let the third recover. That's it. That's the whole defense, and it only works if you build it before you need it. 7. The Thing You Won't Budget For Post-sale spending goes up. Every time. The house. The second house. The travel that used to be two weeks and is now two months. The family members who now know what you're worth. And the big one: the deals. You're 40, you're good at business, you're bored by March, and everyone in your network suddenly has a company they'd love to have you in on. The angel checks start at $50,000 and they do not stay at $50,000. There's nothing wrong with any of that. But it belongs in the plan, not next to it. Wall off a defined sleeve, say $500,000, for deals and ventures, and build the rest of the plan on the assumption that sleeve goes to zero. If it does, you're fine. If it doesn't, you're better than fine. What you cannot do is fund it out of the money that's supposed to feed you for fifty years. See what a $10million dollar portfolio looks like: $10mil Portfolio from Scratch Final Thought The number that made you feel done is not the number that keeps you done. Ten million dollars at 40 is a remarkable outcome and a real constraint at the same time. It buys a life most people don't get. It does not buy an unlimited one, and the plans that fail are almost always the ones that confused the two. The people who get this right treat the sale as the beginning of the hardest financial decade of their life, not the end of it. They build the withdrawal structure before they build the wine cellar. They use the low-income years right after the sale instead of coasting through them. If you had to live on this money for the next fifty years and never earned another dollar, would your current plan survive the first bad five? If you are a Business owner or someone who wants to retire early please schedule a call, and talk with a Moment founder. Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I received frequently about this topic. How much do I need to retire at 40? It depends far more on your annual spending than on a target net worth. Working backward is more useful: take your real after-tax spending, add health coverage, and divide by roughly 3% to 3.5%. A household spending $250,000 a year needs meaningfully more than one spending $150,000, regardless of what the business sold for. Is the 4% rule safe for early retirement? Generally, no. The 4% guideline was derived from 30-year retirement horizons. A 40-year-old is planning for 50 years or more, which is why most analysis of longer horizons points toward a starting rate closer to 3% to 3.5%.. How do I get health insurance before Medicare? The main options are COBRA from the business for a limited period, an ACA marketplace plan, a spouse's employer plan, or coverage through a new venture. At high income levels you should plan on paying unsubsidized rates. Eligibility for any premium assistance depends on your income and the rules in effect that year.. Can I access my 401(k) before 59½ without a penalty? Yes, through a few specific paths, most commonly a 72(t) substantially equal periodic payment schedule, or a Roth conversion ladder where converted amounts become accessible after a five-year holding period. Both have strict rules and real consequences if broken. What is a Roth conversion ladder? Converting portions of a pre-tax retirement account to a Roth IRA over several years, ideally during low-income years. Each conversion becomes accessible penalty-free after five years, creating a rolling bridge to age 59½ while locking in lower tax rates on the conversion itself. What is sequence-of-returns risk? The risk that poor investment returns early in retirement, combined with ongoing withdrawals, permanently damage a portfolio even if long-term average returns are fine. It is the single largest threat to an early retirement plan. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

If you've built something worth passing on, you've already answered the question of whether you need a trust. Do you want your family to skip a courtroom when you're gone? Do you want what you own to stay private, instead of sitting in a public record? Do you want a say in how your kids inherit, instead of handing an eighteen-year-old everything at once? Do you want less of what you built going to the IRS? Answer those, and you've answered the real question. Net worth was never it. If you're a business owner, this question gets more complicated, not less. We built a deeper walkthrough for exactly that: The Moment Guide To Estate Planning For Business Owners. So before we talk about trusts, let's talk about what they're actually solving. What Happens To Your Stuff Right Now If you passed away tonight, what happens to everything you own? Not what you hope happens. What actually happens, based on the paperwork sitting in your file cabinet right now. Does your house go to who you want? Do your kids get looked after the way you'd choose? Most people can't answer that with confidence. If you don't have a trust, here's what fills that gap: probate. Probate is the court process that settles your estate after you die. A judge oversees it. Debts get paid. Assets get sorted and distributed. Eventually, your family gets what's left. In Missouri, that process takes 9 to 15 months. Sometimes longer if anything gets complicated. It's also public. Court records are open. A nosy neighbor could look up exactly what you owned and who inherited it. And it isn't cheap. Missouri requires an attorney to represent the executor through the entire process. Those fees, plus court costs, come out of what your family actually receives. I Have A Will. Doesn't That Cover Me This is the mix-up I run into more than any other. A will does not avoid probate. A will goes through probate in most cases. A will is really a letter to the judge. It tells the court who should get what. The court still has to open the case, verify the will, notify creditors, and approve everything before your family sees a dollar. Same timeline. Same public record. Same attorney requirement. A will decides who gets your stuff. It does nothing to change how they get it. That's the piece a trust actually fixes. The Cleanest Transfer Of All Before we get to trusts, credit where it's due. For certain assets, you don't need a trust or a will to skip probate. You need a form. Retirement accounts, life insurance policies, and most bank accounts let you name a beneficiary directly. Missouri even allows this for real estate, through what's called a beneficiary deed. Sign it, record it with the county before you die, and that property transfers straight to the person you named the moment you're gone. No probate. No court. That's about as clean as a transfer gets. For a lot of families, beneficiary designations already handle more of the estate than they realize. What A Revocable Living Trust Actually Does This is the trust most people should think about next. Not the fancy ones built for estate tax. This one. A revocable living trust is a legal container you create during your life to hold your assets. Your house, your accounts, your other property- you move it into the trust. You still control every bit of it. Buy, sell, change the terms, whatever you want, whenever you want. "Revocable" just means you're free to undo it. Here's the entire point: assets held in the trust skip probate completely when you die. They pass directly to the people you named, privately, in weeks instead of over a year. It does something else a will can't. If you ever become unable to manage your own affairs an accident, an illness, anything- the person you named as successor trustee steps in immediately. Nobody has to petition a judge for permission to pay your mortgage while you recover. You do not need to be wealthy to have one of these. That's the biggest misconception out there, and it's worth repeating. A revocable living trust isn't about how much you have. It's about what you own and whether you want your family stuck in a courtroom for over a year to sort it out. Own a house? Have kids? Own a small business? Want your affairs to stay private? That's the bar. Not a dollar amount. Flowchart on a Revocable Trust Where Net Worth Actually Starts To Matter Here's where the conversation genuinely shifts. There is a point where net worth matters. It's just much higher than most people think, and it has nothing to do with probate anymore. It's about gift and estate tax. Every person gets a federal gift and estate tax exemption, a lifetime allowance for what you can give away, during life or at death, before the federal government taxes it. In 2026, that number is $15 million per person, or $30 million for a married couple. That's a high bar, but it's not an abstract one if you own a business, hold investment real estate, or have equity that's compounding. A company worth a few million today can be worth a great deal more in a decade. If you're building toward that number, or past it, a revocable living trust is no longer the whole plan. It's step one. The real question becomes how much of what you've built stays with your family instead of the IRS. That's where irrevocable trusts come in. An irrevocable trust works differently. Once you fund it, you give up control for good. You can't change your mind and pull the assets back. In exchange, those assets and everything they grow into can come out of your taxable estate entirely. Two tools built on that idea come up most often. A SLAT — a spousal lifetime access trust- lets one spouse gift assets into an irrevocable trust for the other spouse's benefit. The assets leave the donor's taxable estate. The family keeps indirect access through distributions to the beneficiary spouse. It's a way to use exemption now while keeping a safety net at home. Flowchart of a SLAT A GRAT — a grantor retained annuity trust- is built for assets you expect to grow fast. You place the asset in the trust and take fixed payments back over a set number of years. Whatever growth beats the IRS's assumed rate passes to your beneficiaries, often using little to none of your lifetime exemption. Neither of these is a DIY project. They require an estate planning attorney and close coordination. But if your estate is approaching $15 million, or heading there because of how a business or portfolio is compounding, this is the stage where the question stops being "should I have a trust" and becomes "which kind, and how many." Flowchart of a GRAT The Trust Guide – So, What's The Real Answer? Almost every estate needs a revocable living trust. That one has nothing to do with net worth. It's about keeping your family out of probate court and having someone ready to step in the moment you can't. Where it goes from there depends on where you sit. If you're a few million into building something- a business, a portfolio, a real estate footprint- the trust conversation isn't finished. It's just getting started. The tools change as the number grows, but the goal never does: keep control while you're building, and keep as much of it as possible with the people you're building it for. Figure out which tier you're actually in. The rest gets easy from there. If you want to see this in action, we put together a short video on why an estate plan matters, no matter what you're worth: Watch it here. Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I received frequently about this topic. Can you change your trust after it is created? Yes, if it's revocable. You can update beneficiaries, change trustees, or dissolve it entirely, anytime, for any reason. That flexibility disappears with an irrevocable trust, which is why the decision to use one is bigger. Does a trust protect my assets from lawsuits or creditors? A revocable living trust does not, since you still control the assets, courts treat them as yours. Certain irrevocable trusts can offer creditor protection, but that's a different tool built for a different purpose. How much does a trust cost, and how long does it take to set up? It varies with complexity, but a revocable living trust is typically a much smaller upfront cost than what your family would pay in probate fees later. Setup usually takes a few weeks, not months. Do assets in my trust still get a step-up in basis when I die? Yes. Because you retain full control of a revocable trust while you're alive, the IRS treats those assets as still part of your estate. Your beneficiaries get the same stepped-up basis they'd get if you'd owned everything outright. Who should I name as trustee? Most people name themselves while they're alive and able, then a spouse, adult child, or trusted advisor as successor. For larger or more complicated estates, some families add a corporate trustee, like a bank or trust company, for continuity and neutrality. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

Six months ago, you were sleeping in a dorm room or off-campus housing. Now your name is getting called on national television. A four-year deal. Tens of millions of dollars. All fully guaranteed. For you and most rookies, this is the first time in your life you are earning significant income. And without the right guidance, that could all go away as quickly as it came in. In today's blog, I am going to walk you through what really happens to your signing bonus once you put pen to paper. Top 5 Pick Breakdown Here's what a top-5 pick contract actually looks like. You sign a four-year rookie deal worth $50 million, fully guaranteed. Of that, $33 million is paid as a signing bonus. The rest is base salary, paid out year by year as you play. Contract Length 4 years Total Contract Value $50,000,000 Signing Bonus $33,000,000 Fully Guaranteed Yes On paper, you just became a multi-millionaire. But in reality, this is where things get complicated fast. And one of the things every player needs to understand when it comes to athlete wealth management. When Does the Money Actually Show Up? Here's the first thing most families don't realize. Your signing bonus and your base salary are not the same thing, and they don't show up on the same timeline. Your signing bonus arrives almost immediately. Once you sign, the team typically pays the full signing bonus within days. It does not matter if you have practiced, played a preseason snap, or stepped on an NFL field. It's guaranteed money, and it shows up fast. Your base salary works completely differently. You get paid through game checks, and game checks only start once the regular season begins. That means no meaningful base salary income shows up until September, broken into roughly 17 to 18 weekly payments across the season. There's also a small per diem during offseason workouts and training camp, usually a few hundred dollars a week. It covers meals and incidentals. It is not real income, and you should never confuse it with your salary. So picture your actual cash flow: May: Your $33 million signing bonus hits your account within days of signing June through August: Small weekly per diem during offseason programs and camp September through January: Weekly base salary game checks during the regular season That's your entire first-year cash flow. One enormous payment up front, then silence for months, then a steady trickle of game checks. If nobody explains this timeline to you in advance, it creates real problems. I have watched families assume a big number means big checks every month. It doesn't work that way, and the gap between signing and your first game check has caught more than one family off guard. The First 30 Days Matter More Than You Think The 30 day window right after you sign to the day you get paid is arguably one of the most important of your professional career. The same week that $33 million hits your account is the same week everything else in your life speeds up. New agent relationships turn into new "business opportunities." Family members start mentioning things they've always wanted. People you haven't talked to since middle school find your number. And somewhere in the middle of all of it, you're also trying to learn a new playbook and make a 53-man roster or at least make a good first impression. This is exactly the window where good decisions and bad decisions get made, often before you've had a chance to think clearly about either one. Here's what actually matters in those first 30 days: Don't touch it yet. The money doesn't need to do anything immediately. It needs to sit, untouched, while you build the right team around it. Set aside what you'll owe before you do anything else. Even with withholding already taken out, you want a clear, conservative picture of what's actually yours to work with. Have one person you trust managing the full picture. Not your agent, not a family member, not a friend who's "good with money." One advisor whose only job is to look out for your long-term financial life, separate from anyone negotiating your deal or asking you for anything. Slow down every big decision for at least a few weeks. Cars, houses, "investments" from people you just met, all of it can wait. Nothing about a smart financial decision requires urgency. If someone is pushing you to move fast, that's a signal you need to pay attention to. The players who handle this window well aren't the ones who are smarter than everyone else. They're the ones who knew building the right time was the first important step to financial freedom. Who Decides the Payment Schedule? Short answer: not you, at least not until everything is signed. The payment structure, lump sum versus spread out, timing of base salary, any roster bonuses tied to specific dates, gets negotiated into your contract before you sign. Once it's signed, the schedule is locked. You can't call the team in October and ask for an early payment because the timeline is fixed by contract language. Take a top overall pick, for example. His side wants the full bonus in one lump sum, which has become the norm for No. 1 picks in recent years. But his team's standard practice might be installments instead, a large percentage shortly after signing, the rest split across later payments. Neither approach is wrong. It's simply team custom, and it can hold up a nine-figure deal for weeks over when the money arrives, not how much. This is exactly why the people negotiating your contract matter so much. The headline number gets all the attention. The structure underneath it, when your money actually arrives, how guaranteed it really is, what happens if you're released, deserves just as much. Don't assume a lump sum is guaranteed just because it's trended that way. Some teams have their own house rules, and those rules become your reality the moment you sign. Tax Withholding: What Comes Out Automatically Unlike NIL income, which is typically reported as 1099 income with nothing withheld, your NFL paycheck is treated as W-2 income. That means taxes are automatically withheld before you ever see the money. Here's roughly how it works on a bonus this size. Federal withholding. The IRS treats bonuses as supplemental wages. The standard supplemental withholding rate is 22%, but once your supplemental wages cross $1 million in a calendar year, withholding jumps to 37%. On a $33 million bonus, your team is required to withhold at the higher rate almost immediately. Important distinction: that withholding is not necessarily your final tax bill. It's just what gets held back during the year. Your actual liability gets reconciled when you file, based on your real tax bracket, and for income at this level, that bracket is going to be 37% federal regardless. State withholding. This is where things get more complicated, and more interesting. States generally tax this kind of income based on a combination of where you're domiciled and where your "duty days" actually take place, meaning practices, games, and team activities physically performed in that state. Multiple states can end up with a claim on a single paycheck. This is sometimes called the "jock tax," and it's a real factor for any professional athlete who travels for work, which is all of them. Can You Pick Your Tax State? This question comes up constantly, and I understand why. A handful of states, Florida, Texas, Tennessee, Washington, have no state income tax. On a $33 million bonus, the difference between paying state tax and not paying state tax is enormous. So can you just move to a no-tax state before signing and avoid it? Sort of. And this is exactly the kind of question that needs a real answer, not a guess. Here's what actually matters: Residency isn't just an address. States look at where you genuinely live, your driver's license, voter registration, where your primary home is, where your family lives, how many days you actually spend there. A short-term rental in a no-tax state while your life continues somewhere else generally won't hold up if it's ever challenged. Duty days still apply. Even with legitimate residency in a no-tax state, road games and practices in other states can still create tax obligations in those states. Full avoidance is rarely realistic, even for players who have done this the right way. Timing is everything. Residency planning has to happen before your bonus is paid, not after. Once that money hits your account, the planning window has closed. This is not a do-it-yourself project, and it's not something a generic advisor should be guessing at for you. This is exactly the kind of strategy that requires a tax professional who specializes in athlete tax planning, working alongside your agent, before your contract is even finalized. The Smart Play: Live on Less, Let the Rest Grow Here's something I've seen separate the players who are financially secure 20 years from now from the ones who aren't. Your signing bonus is not spending money. It should be your foundation. The smartest approach I've seen is simple: live on a portion of your game checks and any endorsement income, and let your guaranteed contract money sit, invest, and grow largely untouched. Remember, your playing career is a window and a short one at that. Your game checks stop the moment your career ends. But money that's invested early, during your 20s, has decades to compound before retirement. This ties directly into the benefits you're also building during your career, like the league's Player Annuity Program, the 401(k) with a 2-for-1 team match, and the pension. These benefits matter. But they were never designed to be your entire plan. Your signing bonus, handled correctly from day one, is what actually builds generational security. I put together the entire guide to the NFL Retirement Plan if you want to take a deeper dive. Final Thought Your signing bonus is the biggest financial moment you may ever experience, and it happens before you've thrown a single professional pass, made a single tackle, or caught a single ball. That's exactly why it deserves more attention than a headline number on draft night. The players who come out of their careers in a strong financial position aren't always the ones who got drafted the highest or signed the biggest deal. They're the ones who understood, from day one, what they were actually keeping, what they actually owed, and what that money needed to do for the next 50 years of their life. If you are in the National Football League and want to better understand the NFL signing bonus, schedule a call with a Moment Founder. Not sure what questions to ask, check out this video on 10 questions you should ask when interviewing a financial advisor. Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I receive frequently from entrepreneurs. How do you help rookies plan around the gap between their signing bonus and their first game check? We build out a full cash flow picture, so there are no surprises when the money slows down after the signing bonus deposit. How does Moment private wealth help athletes navigate withholding and their real tax liability? Moment Private Wealth serves clients by running quarterly tax projections ahead of time so you know your actual liability, not just what's withheld. How are you different from my agent? Your agent negotiates your signing bonus and playing contract. We manage what happens to the money after and make sure those two roles stay separate. What does your average client look like? Our clients are nearly all athletes and business owners. Our average client has a net worth greater than $5M. The strategies, solutions, and planning that we implement have a high-net-worth and ultra-high-net-worth client in mind. How does Moment Private Wealth think about the league's 401(k) and other benefits? We treat those benefits as one piece of a larger plan and build the rest of your strategy with them in mind. Why should I consider hiring Moment Private Wealth? Great question! But first, let us explain why you shouldn’t hire us. If you’re looking for an advisor who will pitch shiny object investments or be a “yes man” you are in the wrong place. Why? Because we believe in being truth tellers and only giving advice that we take ourselves. The investments, strategies, and planning we do are all things our advisors do with their own money. If you are an athlete or business owner interested in things like lowering your tax bill, investing smarter, and finding a trusted partner we might be a good fit. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

Joe owns a mechanical contracting company outside Kansas City. A competitor made him an offer last spring, a good one, on paper. Joe called me, excited. Then, the buyer asked for his last three years of financial statements. That's when things fell apart. Joe had been running his truck payment, his son's phone bill, and a chunk of his health insurance through the business. His salary jumped around every year depending on his mood and his cash flow. His retirement plan got funded once, two years ago, when he had a good quarter. None of it was wrong. But none of it told a buyer a clean story. The deal didn't die. It just got smaller. A lot smaller. Here's the part almost nobody tells business owners: a buyer isn't looking at your business today. They're looking at your business for the last three years. If those three years are messy, no amount of last-minute cleanup fixes it in three months. For more on what to do when selling your business, here is our guide on selling your business. Why Buyers Look in the Rearview Mirror When a buyer or a bank lending to that buyer evaluates your company, they don't just want this year's numbers. They want a pattern. Most acquisition loans, including SBA loans, require the seller's tax returns and financial statements for the past three years before the bank will even consider funding the deal. That's not a suggestion. It's the standard. Think of it like selling a used truck. Nobody buys a truck off a single glowing test drive. They want the maintenance records. They want to see it was cared for consistently, not just detailed the morning of the sale. Your business is the same. One good year doesn't prove anything. Three consistent years do. Clean Up Your Numbers Before Someone Else Reads Them You want to make sure you don't have any personal expenses running through your business because, when it's time to sell, every one of those expenses has to be explained, documented, and "added back" to show your true profit. If you do that cleanup the year of the sale, a buyer's advisor will see exactly what happened: a business dressed up right before showing. That destroys trust, and trust is worth real money in a negotiation. If you do that cleanup three years out, it just looks like how you run your business. Buyers pay more for numbers they don't have to question. Same goes for your own salary. Buyers and appraisers normalize what an owner actually gets paid to figure out the business's true earning power. A salary that jumps from $60,000 to $180,000 to $40,000 over three years doesn't read as flexibility. It reads as risk. The Entity Clock Nobody Tells You About If your business is structured as a C-corporation and you're thinking about converting to an S-corp before you sell, pay close attention here; this is where three years isn't even enough. Under IRC Section 1374, when a C-corp converts to an S-corp, the IRS still wants its cut of the value the company built up while it was a C-corp. That's called the built-in gains tax, and it can apply for a full five years after the conversion date if you sell appreciated assets during that window. That means if you're planning to sell in three years and you convert today, you could still owe that tax. The clock has to start even earlier than the rest of this article suggests. QSBS: The New Rule Almost Nobody Knows About If your business is a C-corporation, there's a benefit that changed dramatically in 2025 that most owners have never heard of. Under the new law passed as part of the One Big Beautiful Bill Act, stock issued after July 4, 2025 now qualifies for a tiered tax exclusion under Section 1202, often called QSBS, or Qualified Small Business Stock: Hold the stock 3 years; exclude 50% of the gain Hold it 4 years; exclude 75% Hold it 5 years; exclude 100% The cap on how much gain you can exclude also went up, from $10 million to $15 million per owner, and the company has to stay under $75 million in gross assets to qualify. This is not automatic. It only applies to original stock issued directly by a C-corporation running an active qualifying business; not every industry qualifies, and not every structure qualifies. But for the right business, this is one of the most powerful tools in the tax code, and it only works if the clock has already been running for years before you sell. You can't retroactively "add" holding time after a deal is signed. Your Retirement Plan Needs a Track Record Too If you're running a cash balance or defined benefit plan to shelter income and build retirement savings, the IRS expects that plan to look permanent, not like something you set up the year before selling just to shovel money in and shut it down. A plan funded consistently for three-plus years tells a very different story than a plan funded once, right before a sale. One looks like retirement planning. The other looks like it was designed around the deal, and that invites scrutiny. The Math Behind Waiting Too Long Here's the number that should stop every owner reading this: according to the Exit Planning Institute, only 20% to 30% of businesses that go to market actually sell. The rest sit there, get pulled, or sell for far less than the owner hoped. A big reason is timing. Most owners start thinking seriously about selling only after they've already decided they're done, three, six, twelve months out. By then, the financial story is already written. There's no time left to rewrite it. Think about training for a marathon. You can't cram three years of conditioning into the final three months. You can run harder those last months. You can't undo three years of not running. Your business's financial story works the same way. The moves that actually move the needle clean books, consistent comp, the right entity structure, a real retirement plan, and, in the right case, QSBS- all take years to build, not months. What Joe Would Tell You Now Joe still sold his business. Just not for what it was worth, and not on his timeline. He told me afterward: "I wish somebody had told me this three years earlier." Now you know. The best time to start planning your exit wasn't three months ago. It's today, even if you're not selling for years. Want to see this broken down step by step? Watch our YouTube video on what to do before you sell your business here. Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I received frequently about this topic. Why do buyers care about three years of financials instead of just the most recent year? Because one good year could be luck, a one-time contract, or a market swing. Three years shows a pattern. That's why most acquisition loans, including SBA loans, require three years of tax returns and financial statements before a bank will fund the deal. What is an "add-back," and why does it matter? An add-back is a personal or one-time expense that gets added back into your profit to show the business's true earning power. Buyers accept add-backs when they're well-documented and consistent. They get suspicious when add-backs show up for the first time the year you decide to sell. What if I'm planning to sell in less than three years is it too late for any of this? No. Even one extra year of clean, consistent numbers is better than none. The earlier you start, the more options you have, but starting late is still better than not starting. How do you work with other members of my team? We believe in the power of the team. For most of our clients, their team consists of Moment Private Wealth, an accountant, an attorney, a banker, and an insurance specialist. We help our clients build out their team of individuals or work with existing partners that clients have. Our goal is to ensure every family has a team of experts to protect their interests. Why should I consider hiring Moment Private Wealth? Great question! But first, let us explain why you shouldn’t hire us. If you’re looking for an advisor who will pitch shiny object investments or be a “yes man” you are in the wrong place. Why? Because we believe in being truth tellers and only giving advice that we take ourselves. The investments, strategies, and planning we do are all things our advisors do with their own money. If you are an athlete or entrepreneur interested in things like lowering your tax bill, investing smarter, and finding a trusted partner, we might be a good fit. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

I have spent years sitting across the table from athletes and their families. From 1st round draft picks, to league all-stars, to guys who've earned $100M+ in their careers. Here's the thing I have noticed working with players at your stage of your career. Nobody ever benches their wealth advisor. You'll change agents. You'll change trainers. You'll change your diet, your workout program, anything that stops working the way it used to. But the guy managing your money? For most players, that's the one relationship that never gets a second look, no matter how much has changed since it started. In today's blog, I want to walk through why that happens, and the silent signs that tell you it might be time for a real conversation with your wealth advisor as a professional athlete. The Silent Sign You've Outgrown Your Wealth Advisor as a Professional Athlete Why This Relationship Never Gets Re-Evaluated Every other relationship in your career has a built-in trigger to reassess it. A bad season. A poorly negotiated contract. A trainer who can't get you healthy. Something breaks, and you notice. The relationship with your wealth advisor doesn't work that way. There's no bad game to point to. No box score. Just statements that show up, a call once or twice a year, and the assumption that if nothing feels obviously wrong, everything must be fine. That's the trap. Because "nothing feels obviously wrong" and "this is actually working as well as it could be" are two completely different things, and most players have never had a reason to find out which one is true. The Advisor Who Got You Here Was Solving a Different Problem Think about who you hired, and when. For most players, that relationship started early. Maybe it was someone your agent recommended. Maybe it was someone your family knew. Maybe it was whoever showed up at the right moment when you were 21 and needed someone, anyone, to help you figure out what to do with your first real contract. That person was solving a 21-year-old's problem. First contract First real money Basic questions Get the fundamentals in place But you're not that guy anymore. Your contracts have gotten bigger. Your questions have gotten more complicated. Here's the reality: You are closer to retirement than you are to your first year in The Bigs. You're at the point now where you need to start thinking seriously about what life looks like after the game ends. That can be a daunting reality to face. So the question worth asking isn't whether your advisor was good at the job in year one. It's whether the relationship has actually grown alongside everything else in your career, or whether you're still getting the same conversation you were getting back then, just with bigger numbers attached to it. The Silent Signs It's at this point where I want to share with you some of the silent signs I have seen as a wealth advisor for professional athletes that oftentimes go missed. Here's what I'd actually pay attention to: You couldn't explain your own plan if someone asked you to. I am not talking about the balance in your investment account. I am talking about the plan. What happens after I hang it up? Where will my money come from? What happens if I am not here in 5 years? What if I want to start a second career? Does my plan include that option? These are all questions that are different from when you first started. And questions that, quite frankly, should have been answered years ago. Every conversation feels the same, no matter how much has changed. This one doesn't get talked about enough. Guys, if your advisor is showing you the same "summary" of your investment performance, something is not right. Your advisor needs to be reviewing everything with a dollar sign in front of it. Your cash flow. Your tax plan, Your estate plan. Your insurance coverages. These things need to be reviewed yearly (at the very least). It is the little things that set your advisor apart, especially as you near this new stage of life. You've never been asked a real question about your career, only talked about money. You are going to be a retiree a lot longer than you will be a professional athlete. And with that comes new realities. Have you talked to your advisor about: How much longer you realistically plan to play What happens if it your career ends earlier than expected Can I sustain my lifestyle without a constant paycheck All of these questions are honest and realistic, but have very little to do with "investments." You find out about big financial moves after they've already happened. I hear it over and over again from guys we have brought on after they have been with an advisor. "Well, he came in with a fancy suit, threw a bunch of terms at me I've never heard of, but said I was all good." Let me tell you something, this is not healthy. You don't need to be the financial expert. But you should be able to understand your financial plan and why it is being recommended. If that's not the case, it may be time to get another opinion. You've never once heard "I don't think that's the right move for you." I am all about building true, authentic relationships. But with that, comes someone who is not afraid to tell you no. If you think about all the important people in your life. The people who you trust with every ounce of strength you have. I'd bet they would be someone who isn't afraid to tell you the truth. When it comes to managing your money, if your advisor is a "yes man" then they are more interested in keeping you comfortable than looking out for your best interest. Nobody has ever proactively brought up post-career planning. When we first start working with guys, this is a topic of conversation. It's almost like we are working backwards. Father time is undefeated. Professional sports will end. And when it does, what do you want it to look like? If you've been in the league for years and nobody's asked what you actually want your life to look like when this ends, they aren't looking at protecting your financial future. Loyalty Isn't the Same as Fit Here's what stops most players from ever looking into this. It feels disloyal. This is the guy who was there from the beginning. Bringing in a second opinion feels like a betrayal of that, so guys just don't do it, even when something feels a little off. I understand that instinct. But loyalty to a person and fit for where you are in your career are two different things, and confusing them is exactly what keeps players stuck with a setup that stopped serving them years ago. A second opinion isn't a betrayal. It's due diligence, the same kind you'd expect from any other part of your professional life. Nobody thinks twice about getting a second opinion on a medical decision, a contract negotiation, or a major business move. Your entire financial future deserves at least that same level of scrutiny, especially at this stage of your career. What a Real Second Opinion Actually Looks Like No good advisor is in the business of taking you away from good relationships. Well, at least they shouldn't be. However, a great advisor asks a few honest questions to see how the answers land. Can your current advisor clearly explain what your plan is actually built around? Do they understand your specific career, your specific league's structure, and what your timeline realistically looks like? Have they ever told you no? Do they know what you actually want your life to look like after this career ends? If those answers come easily and confidently, that's a good sign. If they don't, or if you realize you've never actually asked, that's worth sitting with. Final Thought The players who come out of professional sports in the strongest position aren't always the ones who made the most money. They're the ones who never let a relationship coast just because it was comfortable, especially the one responsible for their financial life. You wouldn't run the same training program you had at 21. You wouldn't take advice from a coach who stopped adjusting to who you've become. Your financial plan deserves the same standard. If it's been awhile since you've actually stress-tested that relationship, I would start now. If you are at this point in your career and want a second opinion, schedule a call with a Moment Founder. Not sure what questions to ask, check out this video on 10 questions you should ask when interviewing a financial advisor. Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I receive frequently from professional athletes. How do I know if it's time to get a second opinion on my financial advisor? If you can't clearly explain your own plan, if every conversation feels the same regardless of what's changed in your career, or if post-career planning has never come up, those are all signs worth paying attention to. Isn't switching financial advisors disruptive? Not when it's done right. A good second opinion starts with a conversation. You are simply gathering information, not blowing anything up. How is Moment Private Wealth different from a typical financial advisor? We work specifically with athletes and business owners, which means we understand career structures, contract timing, and post-career planning in a way a generalist advisor typically doesn't. We also have the fire power to deliver for you as a professional athlete. What does your average client look like? Our clients are nearly all athletes and business owners. Our average client has a net worth greater than $5M. The strategies, solutions, and planning that we implement have a high-net-worth and ultra-high-net-worth client in mind. Why should I consider hiring Moment Private Wealth? Great question! But first, let us explain why you shouldn’t hire us. If you’re looking for an advisor who will pitch shiny object investments or be a “yes man” you are in the wrong place. Why? Because we believe in being truth tellers and only giving advice that we take ourselves. The investments, strategies, and planning we do are all things our advisors do with their own money. If you are an athlete or business owner interested in things like lowering your tax bill, investing smarter, and finding a trusted partner we might be a good fit. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

What happens the moment you get the call that a team is selecting you in the draft? For most athletes, the honest answer is nothing planned at all. Here is what usually happens. The player signs the contract; 30-45 days later, they see a number larger than anything they have ever seen direct deposited into their account, and then it sets in as they ask themselves, "what now?" Players spend years perfecting their swing and zero hours thinking about taxes, insurance, or what happens to that money once the season ends. This is the reason the financial checklist for athletes exists. Whether you just got drafted, called up, or signed your first extension deal, the choices you make in the next few months set the tone for the rest of your career, and often for the rest of your life. In this blog, I am going to walk through exactly what to do first, from building the right team around you to protecting the paycheck you worked your whole life to earn. Build the Team Before You Need It You would never take the field without a coaching staff. Don't manage a seven- or eight-figure contract without the financial equivalent. At this stage of your career, you most likely already have your agent in place. So what else should you be thinking about as you build your team? At minimum, that means a fee-only financial advisor acting as a fiduciary, meaning they are legally obligated to work in your interest rather than sell you products. It means a CPA who has actually handled multi-state athlete returns before, because the jock tax rules that apply to you don't show up in most general tax practices. Something to keep in mind as you go through this vetting process is transparency on fees. Ask directly how someone is compensated before you ask what they recommend. Know What You Actually Take Home The contract number that ran in the headlines is not the number that hits your account, and the gap between the two catches almost every rookie off guard. Between federal and state income tax, agent fees, and union dues, our real take-home pay is often well under half of the reported figure. Before you make a single spending decision, build out the full picture: 1) Gross Contract Value: the number that ran in the press release 2) Projected Tax Liability: federal, state, and city obligations based on where you play and live 3) Fees and Withholdings: agent commissions and union dues 4) True Net Income: the number you can actually plan a life around Signing bonuses are frequently taxed on a different schedule than salary, so get the timing mapped out early rather than discovering it at filing season. Set Up the Right Accounts Before the Money Moves Where your money physically sits matters as much as how much of it there is. Before a signing bonus or first paycheck arrives, get the structure in place so every dollar has somewhere to go. A high-yield savings account or money market fund for your emergency reserve, separate from your everyday checking account A dedicated tax reserve account, funded either upfront from a signing bonus payment or with a percentage of every check; we want to make sure we have money proactively allocated so a tax bill never catches you short come April 15. An LLC or loan-out entity, if you earn meaningful endorsement, appearance, or licensing income outside your playing contract, since business income and player-contract income are often best kept structurally separate Put Basic Estate Planning in Place Early Most 18-24-year-olds don't think about estate planning. Most 18-24-year-olds also aren't sitting on a seven-figure asset base with a public profile attached to it. You are, which changes the math. A will, so your assets go where you intend rather than through your state's default rules A revocable living trust, which can help move assets to your beneficiaries without going through probate and keeps the details of what you own out of the public record A power of attorney and healthcare directive, so someone you trust can act on your behalf if you are ever unable to Updated beneficiary designations on any league pension, group life insurance, and investment accounts, since these override what your will says A guardianship designation, if you have children Put Time to Work The single biggest advantage an 18-24-year-old athlete has over almost every other high earner is time. Money invested now has three or four decades longer to compound than money invested at the tail end of a career, which is exactly the opposite of how most professionals experience their earning years. Once your accounts and reserves are structured, this is where your advisor should start building a diversified portfolio around your actual timeline rather than whatever is trending that quarter. It's also worth knowing exactly what your service time earns you. In MLB, a single day on an active roster locks in lifetime health coverage, and 43 days of service vests you into the pension plan at roughly 2.5% of the maximum benefit, with every additional 43 days adding another slice toward a full payout at 10 years of service. The 2026 league minimum salary is $780,000, and figures like these are set by the current collective bargaining agreement, which is scheduled to expire on December 1, 2026, so treat any specific number as subject to change once a new deal is in place. If you want the fuller framework, our Guide To Retirement Planning for Professional Athletes covers the details league by league. Build a Budget That Survives a Short Career A budget is not a constraint on a professional athlete's life. It is what keeps a five- or ten year earning window from becoming the only good financial years you ever have. Automate savings and investing before the money reaches your checking account, set a fixed share of net income for discretionary spending, and revisit the whole thing at least once a season, because your income and obligations will not stay static. If you want the fuller framework, our Guide to Financial Planning for Professional Athletes walks through how we build these plans with clients from year one. Expect the Pitches, and Say No More Than You Say Yes Once your name is public, you become a target for people who are far more interested in your money than your career. Family members will ask. Old friends will show up with a business plan. Strangers will find a way into your inbox. Run everything of consequence through your advisor and your attorney before you commit to it, and treat any pitch you don't fully understand as a pitch to decline. Saying no early protects the relationships that matter more than it damages them. What Next? Are you working from an actual plan, or figuring this out contract by contract as it comes? Most athletes never had anyone sit down and walk them through this. That's the entire reason Moment exists. If you want a second opinion on where things stand, or you're starting from nothing, schedule a call with a Moment Founder and let's put a real structure around what you've earned. Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I received frequently about this topic. Are you a fiduciary? Moment Private Wealth serves clients as a fiduciary 100% of the time. Do I need to set up an LLC for my baseball income? Not for your player contract itself, since that is W-2 income paid directly by your team. An LLC is worth a conversation if you earn meaningful income outside your contract, such as endorsements, appearances, or licensing. How much of my contract is really going to taxes? It varies by sport, by your state of residency, and by the states and cities where you compete, but the combined federal and state tax bill often surprises rookies who were only thinking about the headline number. Regular estimates should be run by your financial and tax team. I already have an agent. Do I really need a separate financial advisor? Yes, and the two roles aren't interchangeable. Your agent negotiates contracts and endorsements. A fiduciary advisor manages the money once it arrives, including taxes, investments, insurance, and the long game. Neither one replaces the other. How large should my emergency fund be compared to a typical recommendation? Larger than what a standard financial plan would suggest, usually six to twelve months of expenses, because injuries, trades, and short career arcs make an athlete's income far less predictable than most professionals'. Do I really need a trust, will, and an estate plan this early in my career? Yes. Estate planning is not just for later in life. It matters most when you have a meaningful asset base and, often, a family depending on you, which describes most professional athletes the moment they sign a first contract. A revocable living trust, will, updated beneficiary designations, and a power of attorney are worth putting in place early, not after your career winds down. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

I spent nearly a decade in the high-net-worth divisions of two of the largest financial institutions in the country before joining Moment. I sat in the meetings where the advice gets built. And I want to tell you something that took me years to fully understand: the wealth management playbook almost every advisor in America runs was designed for one specific person. That person is a corporate executive in his early sixties. He has W-2 income that climbed steadily for forty years. He has a 401(k) he's been feeding since he was 26. His earnings peak in the last decade of his career, then stop on a planned date. His wealth is liquid, diversified, and sitting in accounts someone else custodies. He is a wonderful client. He is also the most common client in America, which is exactly why the entire industry is built around him. Here's the problem. If you're a professional athlete or a business owner, you are not him. You are close to his mathematical opposite. And you are almost certainly being handed his plan. In today's blog, I want to walk through the three assumptions buried inside standard high-net-worth advice, why each one breaks for athletes and founders, and what should be happening instead Inverted Earnings Curve Assumption #1: Your Biggest Earning Years Are Your Last Ones The entire tax framework of conventional planning rests on one idea. Defer income now, pay tax on it later, because later you'll be in a lower bracket. That works beautifully for the executive. He earns his largest paychecks between 55 and 65, defers aggressively into pre-tax accounts, retires, and pulls that money out in his seventies at a fraction of the rate. Now run the same logic on an athlete. You earn your peak income between 22 and 32. Your career ends. And then you have a period — sometimes years, sometimes decades, where your income is a fraction of what it was. Your lowest-tax years are not at the end of your life. They're in the middle of it. Let me show you what that's worth. Imagine you're 29 and earning $2,000,000 this year. Your playing career ends at 33. Between 33 and 40, your income drops substantially while you figure out your second act. The standard playbook has no name for those years. It doesn't know they exist, because the executive it was built for doesn't have them. But those seven years are the cheapest tax window of your entire life. That's when Roth conversions become extraordinarily powerful. You move money from pre-tax accounts into Roth accounts at a bracket you will never see again, and everything that grows afterward is tax free, for the next fifty years. Miss that window and you don't get it back. You'll be pulling from pre-tax accounts in your sixties at rates set by a Congress none of us can predict. Same math applies to a founder, just on a different clock. The years after you sell and before your next venture ramps up are frequently the lowest-income years you'll have as an adult. The advisor running the standard playbook sees a gap in your income. The right advisor sees the most valuable planning window you will ever have. As financial advisors for professional athletes, we work with people with volatile income throughout their life. Assumption #2: Your Wealth Is Liquid and Diversifiable Ask a conventional advisor about risk and you'll get a conversation about portfolio allocation. Large cap versus small cap. Domestic versus international. Stocks versus bonds. That conversation assumes your wealth lives in a portfolio. For a business owner, it usually doesn't. If you've built a company worth $20 million and you have $1.5 million in investment accounts, then roughly 93% of your net worth is sitting in one illiquid, concentrated, uninsurable asset that depends on your continued involvement. Rebalancing the 7% is not risk management. It's rearranging the furniture. The risks that can actually take you down look nothing like market volatility: Key person risk. The business is worth what it's worth because of you. Customer concentration. Three clients are 60% of revenue. Liquidity risk. You cannot sell 10% of your company to cover a tax bill. Valuation risk. Your number is an estimate until someone wires funds. Athletes have their own version. Your primary asset is your physical ability to perform, it is not diversifiable, and it can be eliminated in a single play. Then come the layered risks the executive never faces — multi-state tax filings, public exposure, and a circle of people who all have opinions about your money. For more check out our Guide to Financial Planning for Professional Athletes. The 93% Problem Assumption #3: You Have Time to Fix a Mistake This is the one that actually keeps me up. If our executive makes a serious financial mistake at 45, he has twenty more years of high income to recover. He can save more. He can work longer. Time is on his side, and the plan is built assuming it always will be. You don't have that. An athlete's earning window can be four years. A founder gets one exit, you don't sell the company you spent fifteen years building a second time. The decisions made in a compressed window don't average out over a long career, because there isn't a long career to average them across. This changes what "good advice" even means. In the conventional model, planning is largely reactive. Something happens, you respond, you adjust, you have decades to smooth it out. In your world, the work has to happen before: Before the contract is signed, not after Before you establish residency in a state that will tax you for years Before the letter of intent, when entity structure can still be changed Before the liquidity event, when trust and gifting strategies still have runway There is a version of nearly every strategy that saves you a fortune if executed in advance and does almost nothing if executed after the fact. The executive's plan can afford to be reactive. Yours cannot. Check out our Guide to Financial Planning for Business Owners for the roadmap that we follow when working for you. Why This Happens Large institutions serve enormous numbers of clients, and to do that at scale you need a repeatable process. A repeatable process, by definition, is built for the most common situation. The executive is the most common situation. So the model optimizes for him. It has to. The result is that people whose financial lives are shaped differently get handed advice engineered for someone else, delivered by people who are often genuinely talented and are running the playbook they were trained on. If you've ever sat across from an advisor and felt like your actual questions weren't landing, that's why. You were the wrong input for the model. Final Thought Every professional athlete and every business owner I've worked with has an inverted financial life. Peak earnings early instead of late. Concentrated wealth instead of diversified. A compressed window instead of a long ramp. Almost everything the standard playbook assumes about you is backwards. That doesn't mean the playbook is wrong. It means it was written about someone else. So here's the question worth asking: is your current plan built around your actual financial life, or is it the standard plan with your name at the top? If you're not sure, these are worth taking to whoever advises you today: What are my lowest-tax years likely to be, and what's the plan for them? What percentage of my net worth is in my portfolio, and what's the plan for the rest? Which of my strategies stop working if we wait another year? The answers will tell you a lot. If you are a Business Owner or Professional Athlete, schedule a call, and talk with a Moment founder. For more on info on how we work with high earning individuals check out this video breaking down exactly what you need to do. Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I received frequently about this topic. I already have an advisor. What should I be asking them? Ask what your lowest-tax years are projected to be and how the plan uses them. Ask what percentage of your net worth their planning actually covers. Ask which strategies expire if you wait. The answers will show you quickly whether the plan was built around you. Why does timing matter so much for Athletes and Business Owners? Because most meaningful strategies, entity structure, residency planning, trust and gifting work, Roth conversions, are dramatically more valuable when implemented before a triggering event. After the contract, after the sale, or after the move, the same strategy is often worth a fraction of what it would have been. Should I be using Roth or pre-tax retirement accounts if my career is short? It depends on which year you're in, and that's the point. In your peak earning years, pre-tax contributions may make sense because you're offsetting income at your highest rate. In the lower-income years that follow, the logic flips — that's often when Roth contributions and Roth conversions do the most work, because you're paying tax at a rate you may never see again. The mistake isn't picking one. It's picking one and never revisiting it. Most of my net worth is in my business. What does risk management actually look like for me? It starts outside the portfolio. That usually means addressing customer concentration, documenting what happens to the business if you're unable to run it, structuring buy-sell agreements if there are partners, building liquidity that doesn't require selling equity, and carrying insurance sized to the actual exposure. Portfolio allocation still matters, but it's addressing the smaller number. My contract isn't signed yet and my business isn't for sale. Is it too early to plan? That's the window where planning is worth the most. Entity structure, residency decisions, trust and gifting strategies, and timing of income all have significantly more value before a triggering event than after one. Waiting until the money arrives usually means the most effective options have already closed. We are only paid in one transparent way, by our clients. We receive no kickbacks or participate in any profit-sharing arrangements. Our fees are simple, transparent, and clear for our clients. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

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 guys don't, and that's not a knock on him. Nobody teaches you to ask that question. The league doesn't. Your agent's job ends at the signature. Your circle wants to celebrate, not plan. Here's the part I've come to believe after years of doing this: your first contract proves you can play. Your second contract is the one that actually decides what your life looks like at 45. It's bigger. It's usually the first deal with real guaranteed money attached to it. And for a lot of players, it's the last contract they'll ever sign with true leverage behind it. Treat it like a supersized version of contract one, and odds are you spend most of it. Recognize it for what it actually is, a 30-to-50-year funding decision wearing a three-to-five-year jersey, and the whole calculation changes. This one's about that shift. Why your second contract needs a different playbook than your first, where I watch that playbook break down most often, and how to actually structure the money so it's still working for you decades after your last snap, at bat, or shot clock. Your Second Contract Isn't a Bigger First Contract Nobody really negotiates a rookie deal. You take what the slot, the scale, or the draft position hands you, because you've got no tape and no leverage, and frankly you're 21 and just trying to make a roster. The second contract flips that on its head, and it does it in three specific ways. Leverage finally exists. You have a body of work now. Teams aren't paying for projection anymore, they're paying for production they've already seen, and that's the only time in most careers where the negotiating power tilts meaningfully toward the player. The guarantee gets real. This is usually the first contract where the number that matters isn't the headline figure, it's how much of it is actually guaranteed at signing versus tied to injury clauses, roster cuts, or per-game escalators. That distinction is where I see the most confusion, and it's worth a direct conversation with your agent about exactly what's protected. The runway shortens, whether it feels that way or not. By your second deal you have real information about how this sport treats bodies. A contract signed at 26 or 27 might be the last big one. I've had clients bank on a third deal that never came, not because they weren't good enough, but because a knee gave out in year two of a three-year contract. Plan for that possibility even if you never need to use the plan. That third point is the one I wish more players internalized earlier. A second contract feels like you made it. I'd rather you treat it like the starting gun on the rest of your financial life. Where This Actually Falls Apart Financial trouble for athletes almost never comes from one catastrophic decision. It comes from carrying rookie-contract instincts into second-contract money without ever recalibrating. A $40,000 mistake on a rookie deal stings, but it doesn't sink you. That same instinct, scaled to second-contract dollars, turns into a $400,000 mistake, and you've got fewer playing years left to earn your way out of it. Three patterns show up again and again with new clients coming off a second deal: 1) Lifestyle scaling to the contract instead of the plan. The house, the cars, the size of the circle around you all grow to match the new number on the page, rather than what's sustainable across the next 40 years of your life. 2) Betting on a third deal that isn't guaranteed to exist. Build the plan as if this could be your last significant payday. If a third contract comes, that's upside. If it doesn't, you're not exposed. 3) Delegating money decisions without keeping a seat at the table. Trusting your team isn't the problem. Trusting them with zero reporting, no second signature, and no visibility into where money actually moves is. Contract two is not the moment to relax. It's the moment to finally build the discipline you wish someone had forced on you during contract one. The Money Has Two Jobs, Not One I say this to nearly every second-contract client I sit down with: this money has two separate jobs, and most players only ever assign it the first one. Job One: Fund the Years You're Still Playing This is the money running your life today, while checks are still coming in. It needs to cover a few things specifically: A genuine cash reserve, roughly 12 to 24 months of expenses, because income isn't smoothed out the way a normal salary is and off-seasons don't come with a paycheck attached Liquid, boring, lo w-drama investments earmarked for anything you already know is coming in the next year or two A lifestyle budget that's allowed to grow, just slower than your income does, not in lockstep with it Job Two: Fund the Fifty Years After This One This is the job most second contracts never get assigned, and it's the reason this article exists. It should include: Retirement contributions maxed wherever eligibility allows, whether that's a league pension, a 401(k), or a non-qualified deferred compensation arrangement for income above standard contribution limits (leagues structure these differently, our breakdown of the NBA Retirement Plan is a good reference point even if you play elsewhere) Long-term, diversified investing, equities, real estate, private opportunities, whatever mix suits your risk tolerance, structured to compound over decades rather than chase this season's return A real plan for the second career, business ownership, broadcasting, coaching, or simply living off the portfolio you built while you still had a jersey number Own-occupation disability coverage, specifically, because a policy that only pays out if you can't work any job leaves you exposed in exactly the scenario you're trying to protect against A Quick Example Say a player signs a second contract with $18 million guaranteed over three years. Run that through the instinct most guys default to, and a good chunk of it ends up funding a bigger house, a bigger circle, and a lifestyle that quietly absorbs most of the guarantee by the time the deal is up. Nothing reckless happened. It just wasn't directed anywhere on purpose. Run the same $18 million through this framework instead. War chest funded. Retirement and deferred comp maxed out. A diversified portfolio built to compound for 30 years. Own-occupation disability coverage in place in case a third contract never materializes. And still, real room to enjoy money that was earned the hard way, because that matters too and I'd never tell a client otherwise. Same contract. Same number on the page. A completely different life at 45. For the fuller framework on structuring income and spending across an entire career, not just a single deal, our guide to financial planning for professional athletes is worth reading next. If estate mistakes are more your concern at this stage, the most common estate planning mistake we see athletes make is a quick, direct read on that specifically. Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I received frequently about this topic. Is my second contract really that different from my first, financially speaking? It is, and I'd argue it's the most consequential contract you'll ever sign. Your rookie deal proves you belong. Your second one typically carries real guaranteed money, genuine negotiating leverage, and less runway left than it feels like in the moment. That combination is exactly why it needs its own plan, not a scaled-up version of whatever you did the first time. How much of my second contract should go toward retirement versus lifestyle? There's no fixed percentage, and I'd be skeptical of anyone who hands you one without knowing your situation. It depends on your league, position, years of service, and what your family actually needs. What stays consistent across clients is the order of operations: cash reserve first, retirement and long-term investing next, lifestyle spending built from what's left over. What happens if I get hurt before my third contract? This is the scenario I plan around most carefully, because it's the one with the least room for a do-over. Own-occupation disability coverage exists precisely for this. Structure your second contract correctly and a career-ending injury doesn't have to double as a financial one. Should I put a large share of my second contract into real estate? Real estate can be a smart piece of the puzzle, and plenty of players like it because it's tangible in a way a brokerage statement isn't. Where I get concerned is when it becomes the entire strategy, one property or one deal carrying too much concentration risk. Treat it as one allocation among several, not the whole plan. My agent already negotiates my contracts. Why do I need a financial advisor too? Because those are two different jobs requiring two different skill sets. Your agent's job ends when the ink dries and the number is as high as it can go. Mine starts there, making sure that number actually compounds into something that outlasts your career. I've yet to meet an agent who does both well, and you shouldn't want one trying to. If you're still sorting out who deserves a seat at your table, what questions to ask a financial advisor is a good place to start. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.

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 keeps growing, and something shifts. A referral comes in for a project that would've been a dream client a year ago, and the founder has to say no. Not because the work isn't good. Because there's no room left in the week. It happens again a few months later. Then it becomes a pattern, good opportunities quietly turned away, because the person who built the business is now the ceiling on how big it can get. That's usually the moment a founder finally asks: do I need to hire someone? It's a fair question, and a loaded one, with a lot more to it than yes or no. Let's get into it. Here's Hiring Your First Employees as a Solo Entrepreneur. Step 1: Figuring out if you're actually ready Why "I'm Overwhelmed" Isn't the Right Reason A lot of founders treat their first hire like a finish line. Get through the hard part solo, then reward yourself with help. It's backwards. The hire is what unlocks the next stage of growth, not a prize for surviving the last one. I've watched founders put off hiring for a year, run themselves into the ground, and then bring someone on out of desperation instead of strategy. That's a rushed decision dressed up as a smart one, and it usually shows. The good news is there's a way to catch this before it happens, if you know what to actually watch for. The Signals Worth Paying Attention To The clearest one is money you're leaving on the table. You're saying no to clients or projects simply because there's no time left in the week. You're spending hours on work that pays far less than your time is actually worth. Deadlines are slipping, and the honest answer is that you're the reason why. Any one of those is a sign you need more hands. All three together means you needed them a while ago. That said, wanting help and being able to afford it aren't the same thing. If your revenue can't comfortably carry a salary for a full year, it's not time yet, even if the exhaustion says otherwise. The founders who get this right are honest with themselves about which one they're actually feeling. As Financial Advisors for Business Owners, we have experience navigating these type of questions. What To Hire For First Most founders default to hiring someone who reminds them of themselves. Someone who "gets it" the way they do. I understand the instinct. It's still usually the wrong call. Try splitting your business into three categories instead. The stuff only you can do: the vision, the key relationships, the calls that carry real risk. The stuff you're good at but shouldn't be doing anymore: delivery, execution, the daily grind of the work itself. The stuff you're bad at and have been avoiding: admin, invoicing, scheduling, the follow-up that never happens. Founders tend to hire into the first bucket when they should be hiring into the second and third. Your first employee should be filling in your gaps, not mirroring your strengths. That's how you end up with a business that gets stronger with each hire, instead of just louder. Step 2: Actually Making the Hire What An Employee Really Costs You Founders almost always budget for the salary line and stop there. That's not the real number. Payroll taxes, workers' comp, unemployment insurance, benefits, tools, and the time you'll spend training someone all stack on top of it. A fair estimate is 1.25 to 1.4 times the salary once everything is accounted for. If your business can't comfortably absorb that fully loaded number, the answer isn't to skip the math. It's to either adjust the offer or wait a little longer. This is one of the first things we sit down and run through with founders before they ever extend an offer. Contractor, Part-Time, or Full-Time How you structure the hire matters just as much as who you pick. Going straight to a full-time employee is the biggest commitment and the biggest risk you can take on. For most first-timers, it's smarter to test the role before you commit to it permanently. Contract or fractional help lets you prove the role needs to exist before you build a full-time position around it. Part-time makes sense when the need is real, but not yet a 40-hour-a-week need. Full-time is the right call once the workload and the budget have both proven themselves out. There's no bonus points for jumping straight to the biggest commitment. Getting the structure right matters more than getting there fast. Write the Job Down Before You Post It Without a documented process, your new hire spends their first months just asking you questions instead of doing the work. This is the step I see skipped most, and it's the one that costs founders the most later. Write out what the role owns. Write out what a strong week looks like in that seat. Write out the tools and systems they'll actually use day to day. Do that work up front, and you're handing someone a real job. Skip it, and you're handing them a puzzle to solve on your dime. Step 3: Keeping Them Around The First 90 Days Decide More than the Hire Does This is the part founders think about the least, and it might matter more than anything above it. Picture this. You make a great hire. They show up ready to go. And three weeks in, they still can't tell you what success in the role even looks like. Without a clear target, even a genuinely talented hire starts to drift. Founders who keep their first employees are the ones who treat the first three months as a real plan, not just a formality before the "real" job starts. That means a written 30-60-90 day roadmap, consistent check-ins, and a concrete outcome they're working toward, not a job description they got handed once and never revisited. The Boring Legal Stuff You Can't Skip None of this is exciting, but skipping it doesn't make it go away. An EIN and the right state payroll registration. Workers' compensation coverage in place. A real, signed employment agreement. A written job description that actually reflects the role. Skipping these steps doesn't save you time now. It just pushes the cost down the road, where it's more expensive and harder to untangle. Final Thought If you're a solo entrepreneur weighing your first hire, here's the question I'd actually ask you. Are you hiring because you're the bottleneck, or because you're just tired? If you can't answer that cleanly, it's worth talking through before you make the leap. Get the structure right early, and you save yourself from a lot of expensive corrections down the line. That's the kind of planning we do alongside founders every day at Moment Private Wealth, building the business and the personal financial picture together, so decisions like this one move you forward instead of creating something to clean up later. If you are a business owner who is looking at hiring your first employee or wondering the best way to structure your business, schedule a call, and talk with a Moment founder. For more on how we are working with Entrpreneurs check out "Entrepreneurship Explained: Quick Wins or Long-Term Wealth?" Get in Touch With An Advisor Frequently Asked Questions Here are some answers to questions I received frequently about this topic. How do I know if I'm actually ready to hire my first employee? Look at what you're turning down, not just how tired you feel. If you're declining work, delaying projects, or spending your time on tasks well below your value, that's your answer. Exhaustion isn't the same signal as readiness. Your revenue also needs to be able to carry the cost for a full year, not just the first few months. Should my first hire be full-time or a contractor? For most first-time founders, starting with a contractor or fractional hire is the safer move. It gives you a chance to confirm the role is actually necessary before you commit to the ongoing costs of a full-time employee. What does an employee actually cost beyond their salary? Budget for roughly 1.25 to 1.4 times the salary once you factor in payroll taxes, workers' comp, unemployment insurance, benefits, and the tools they'll need. Founders who only plan for the salary number are almost always caught off guard later. What's the biggest mistake founders make with their first hire? Hiring someone who works just like them, instead of someone who covers what they're weak at. Your first hire should expand what the business can do, not repeat what you already do well. Can Moment Private Wealth help me think through the financial side of hiring? Yes. Understanding the true cost of a hire, how it impacts your income, and how it fits into your broader financial plan is exactly the kind of work we do alongside founders. *Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.