Spring Training Money Checklist - Are you Building Dynasty or Decline

Spring training is where rosters get decided—but it‘s also where dynasties get decided. At AWM, we‘re the only Athlete Family Office built to help you become a 1Hundred Year Family—a multi-generational, wealthy, flourishing family where the money serves the people, not the other way around. Your spring training money decisions either push you toward dynasty or toward decline.

This isn‘t about having “a guy” or feeling “pretty good” about your finances. This is about installing your family“s Operating System now—so every dollar you earn this season is aligned with your long-term vision, not just this year‘s stat line. Below are simple yes/no questions. If you hit “no” on any of them, it“s time to call us at AWM.

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1. In-Season Housing, Insurance, and Liability (Family Health OS)

Where you live during the season isn‘t just a lifestyle decision—it‘s part of your Family Health Operating System. Your housing, leases, and living arrangements create real liability and estate-planning implications.

Ask yourself:

• Do I have a clear plan for where I‘ll live at each level this year (MLB, Triple-A, likely call-ups), including who is on each lease and what my actual legal responsibilities are?

• Have I reviewed my renters/homeowners policy to confirm my belongings and liability are covered where I‘ll actually be living in-season?

• Have I confirmed I have enough umbrella/personal liability coverage if something goes wrong at my rental (injury, property damage, lawsuit)?

• If I‘m living with roommates or a significant other, do we clearly know who is on the hook legally if something happens?

• Do I know exactly who I would call tomorrow if there were a major property or liability claim?

If any answer is “no”, your Family Health OS has a gap—and you should call AWM to align your housing, liability, and estate planning before you report.

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2. Is Your Income About to Jump by $300k+? (Taxes: #1 Destroyer of Wealth)

Taxes are the #1 destroyer of wealth. A big jump—first full year in the big leagues, arbitration, a new deal, a big endorsement—can either accelerate your 1Hundred Year Family plan or become a tax and safe-harbor nightmare if you don‘t plan ahead.

Ask yourself:

• Is my projected total income this season (on-field + endorsements + NIL/off-field) expected to be at least $300k higher than last year?
• Have I already updated my tax projections for this season with someone who understands MLB contracts, service time, and multi-state tax rules?
• Am I planning to take advantage of safe harbor withholding or estimated payments so I don't get crushed by penalties and surprise tax bills next spring?
• Has someone actually run the numbers on what my safe harbor should be this year based on last year's return and this season's projected jump in income?
• Have I scheduled advanced tax moves before the money hits (entity structure, timing of income, charitable planning, pre-funding investments, etc.) instead of reacting later?
• Do I know what my net number actually looks like after federal, state, and local taxes—not just my headline salary?
• Do I have a written plan for what percentage of every additional dollar above last year I will save and invest?

If any answer is "no," you're letting taxes play offense against your net worth. That's the opposite of a 1Hundred Year Operating System. Call AWM before the first paycheck clears.

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3. Off-Field Income and Your Individual 401(k) (Wealth Creation OS)

Wealth creation is about turning your active baseball window into long-term passive income. Your off-field income—camps, lessons, NIL, content, endorsements, business ventures—is a key part of that. The question is whether it's being routed through a real Wealth Creation Operating System.

Ask yourself:

• As of right now, do I already have an individual (solo) 401(k) set up for my off-field/1099 income—and if not, why not?
• Do I earn (or expect to earn) any 1099 or business income from off-field work this year?
• If yes, have I already opened an individual (solo) 401(k) tied to that business income—not my team paycheck?
• Do I know how much I can put into that individual 401(k) this year without over-contributing or conflicting with other plans?
• Do I have a written contribution schedule (per event, per deal, or per month), instead of "seeing what's left" at year-end?
• Are my solo 401(k) contributions coordinated with my MLB/Vanguard 401(k) so everything works together as one plan?

If you hit "no" on any of these, your Wealth Creation OS is incomplete. Call AWM so we can set up and integrate your individual 401(k) before tax season ramps up.

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4. How Much MLB Time Are You Expecting—and What's Your Vanguard 401(k) Plan?

Time on the Major League roster drives more than service-time milestones; it determines how much you can and should route into the MLB/Vanguard 401(k) and other retirement buckets. A 1Hundred Year Family doesn't guess here—they decide in advance.

Ask yourself:

• Do I have a realistic range (not a fantasy) for how many days I expect to be on the MLB roster this year?
• Have I already completed my Vanguard 401(k) elections for the season, with a clear strategy for pre-tax vs. Roth/post-tax contributions?
• Do I understand how my contribution choices will impact this year's tax bill vs. my flexibility and tax rate in the future?
• Do I know the current 401(k) limits and how the team's contributions interact with my own, so I don't leave free money on the table or accidentally over-fund?
• Have I decided the exact percentage of every MLB paycheck that will automatically go into the plan from Day 1?

If any of these are "no," you're letting one of your most powerful Wealth Creation tools run on autopilot. That is not how dynasties are built. Call AWM so we can align your expected MLB time with a precise 401(k) strategy.

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5. One Year Out from a Potential Lockout: Are You Lockout-Ready?

The current CBA is set to expire next year. A lockout or work stoppage isn't guaranteed—but if it happens, it will expose who has a real Operating System and who is just winging it. Your goal: keep investing in yourself—training, nutrition, skill development—without touching long-term investments or panicking about bills.

Ask yourself:

• If baseball shut down for 6–12 months, could I pay my bills, support my family, and continue elite-level training without selling investments or taking on bad debt?
• Do I have a clear "lockout reserve number" (how many months of core living and training expenses I want in cash or ultra-safe assets)?
• Have I already set up automatic savings from each paycheck this season to build that reserve, or am I hoping to "catch up later"?
• Do I know exactly which accounts I'd tap first to fund training and living costs if income paused—and which long-term accounts are strictly off-limits?
• Have I stress-tested my plan with someone who understands how quickly things can change in a labor stoppage?

If the honest answer to any of these is "no," your Family Health and Wealth Creation OS are exposed. This is the time to fix that. Call AWM now, not when the headlines turn ugly.

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6. The Cash Flow Game: Save, Spend, Share—On Purpose

Every dollar that hits your account this season runs through the same simple flow:

Gross income → Taxes → Net income → Save / Share / Spend.

The question is whether that flow is intentional or accidental. In a 1Hundred Year Family, wealth is the tool and family flourishing is the purpose. You decide in advance what percentage of your net income will:

• Save: Funding your lockout reserve, 401(k)s, investment accounts, and long-term passive income.
• Share: Generosity, giving, and impact that align with your values.
• Spend: Lifestyle today that still fits inside your bigger vision.

Spring training is the perfect time to define your percentages and convert this year's cash flow into long-term outcomes.

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Call to Action: Dynasty or Decline—You Get to Choose

From the start, you get to choose: dynasty or decline. Your career window is short; your family's time horizon is 100+ years. A 1Hundred Year Family doesn't wait until they "feel rich" to put an Operating System in place—they use seasons like this one to decide how every new dollar will be created, captured, converted, and continued.

If you answered "no" to any question above—or you're not 100% confident your "yes" is actually correct—it's time to call us at AWM. We'll help you:

• Install your 1Hundred Year Family Operating System across Human Capital, Wealth Creation, and Family Health.
• Map housing, liability, and insurance so off-field risk doesn't derail on-field opportunity.
• Run advanced tax and safe harbor planning before your income jumps, not after.
• Coordinate your individual 401(k) and MLB/Vanguard 401(k) with a clear contribution strategy.
• Build a lockout-ready cash plan so you can keep investing in yourself without disrupting your long-term investments.

Spring training will decide more than your role on the team. It will help decide whether your story becomes another short-lived earning window—or the beginning of a 1Hundred Year Family.

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