Jason Van Skike- Financial Advisor with Raymond James

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Since kindergarten, Justin Masterson told anyone who would listen that he was going to play MLB ⚾ and tell people about ...
09/03/2026

Since kindergarten, Justin Masterson told anyone who would listen that he was going to play MLB ⚾ and tell people about Jesus.

Nobody in his family had played at a high level. He was a backup point guard as a freshman. He did not touch 90 until a pitching lesson fixed his front side and he jumped from 79 to 89 in one summer.

Then it all happened. Bethel College. A Cape Cod League summer as a temporary fill-in that turned into a closer’s job. San Diego State under Tony Gwynn. Second round to the Red Sox. A debut at Fenway Park with his whole family in the stands. Nine appearances in the 2008 playoffs. An All-Star Game with Cleveland.

How he got there, and why he walked away, is the next episode of Moneyball Wisdom.

Coming soon.

You will remember the day, not the number.Somebody tells you in the clubhouse. You call home. You do not sleep. And some...
08/11/2026

You will remember the day, not the number.

Somebody tells you in the clubhouse. You call home. You do not sleep. And somewhere in the middle of the best week of your life, a check shows up that does not look like what you were told it would be.

About $113,000 gross for the month. That is real. It is more than you made all season in Triple-A. But payroll withholds as though you earn $780,000 every year, because for those 27 days you technically do. Every state and city you play in takes a piece. Clubhouse dues come off daily, and the end of season tip is expected.

None of it is a mistake. It just lands harder when you find out in the moment instead of before.

Then the season ends, and the checks stop. That is the part that catches guys. Twenty seven days in the big leagues does not make you a big leaguer financially. If you are optioned in April, the pay reverts that same day. Plan like it might.

You cannot control when the call comes. You can control what you already know when it does.

MLB ⚾ has put a draft overhaul on the table in CBA negotiations. Nothing has been agreed to. But here is what was propos...
07/24/2026

MLB ⚾ has put a draft overhaul on the table in CBA negotiations. Nothing has been agreed to. But here is what was proposed:

• High school players would no longer be draft eligible
• Players would need to be 20 by September 1 of their draft year and two years removed from high school graduation, starting with the 2028 draft
• College players would become eligible a year earlier than today, so after the sophomore year for most
• The draft would shrink from 20 rounds to 12
• Bonuses would be hard slotted, with the pool starting at $200 million

The MLB ⚾ case is that college baseball has changed. Expanded scholarships, NIL, revenue sharing, better facilities. They point to how many big leaguers now come through the college path.

The players association pushed back hard, saying the proposals would cut more than a billion dollars in player compensation over five years and would bar high school and junior college players under 20 from the draft.

To be clear, this is a proposal. Not a rule. The current CBA expires December 1 and both sides are still at the table.

Worth watching closely.

New from the MLBPA (July 21): the players’ union made its first proposal on the amateur draft, and if you or your player...
07/22/2026

New from the MLBPA (July 21): the players’ union made its first proposal on the amateur draft, and if you or your player could be draft-eligible, this one is about you.

What the union is pushing for:

Keep high school and JUCO players draft-eligible. The current MLB ⚾ proposal would block anyone under 20.

Protect the right to negotiate a signing bonus instead of locked, fixed slots.

Bigger signing bonus pools.

Open the draft to college sophomores, a year earlier than now.

Move the draft back to June.

Here is the honest part: this is a proposal, not a done deal. The league and the union are still far apart, and the current agreement runs through December 2026. Nothing is final yet.

But the pieces on the table right now, eligibility, leverage, and bonus money, are the exact things that shape a player’s first big financial decision. Know how it works before draft day, not after.

That’s me on the mound in college. Nobody was handing out NIL money back then. You played, you took your scholarship, an...
07/21/2026

That’s me on the mound in college. Nobody was handing out NIL money back then. You played, you took your scholarship, and that was the whole conversation.

Now a guy transfers from a mid major with almost no NIL and lands at an Southeastern Conference school with a $250,000 package. The number changes everything, and most players get zero preparation for what comes next.

Four people to have in your corner before that first payment hits:

CPA who works with athletes. Self employment tax, jock tax, deductions. This gets complicated in a hurry and you want someone who has seen it before.

Sports attorney. Every single deal gets read before you sign it. There are too many stories out there. Know exactly what is on that paper.

NIL agent. There is real opportunity in your local market. Chase the deals that fit who you are and who you are trying to reach, not just the biggest check. Then send them to your attorney.

Financial advisor who works with athletes. Investing is only one piece. The point is having someone coordinate the whole picture so you can spend your energy competing.

Your earning window is short and the distractions have never been bigger. Build the team early.

If you are a player or a parent trying to sort out who belongs in your corner, send me a DM. Happy to walk through what these four roles actually do.

613 players drafted. 46 states. One clear shift.Map this year’s class by where each player actually grew up, and Califor...
07/17/2026

613 players drafted. 46 states. One clear shift.

Map this year’s class by where each player actually grew up, and California, Texas, and Florida alone produced more than a third of every pick.

But here’s the real story. The West Coast used to be THE base for baseball talent. California still leads as a single state, but stack it up region vs region and the center of gravity has moved to the Southeast. And early 2027 mock drafts say it’s not slowing down.

Like it or hate it, the academy world is a big reason why.

Think about it. If you’re a top player in a Midwest state, how often are you facing an Southeastern Conference caliber arm? Once a month, if you’re lucky. In these academy leagues down in Florida and Georgia, you’re seeing that kind of arm nearly every day. That kind of competition compounds fast.

Where does your state rank?

Source: mlb.com

It’s official: NCAA baseball rules subcommittee just approved the ABS challenge system for college baseball starting in ...
07/16/2026

It’s official: NCAA baseball rules subcommittee just approved the ABS challenge system for college baseball starting in 2027. Here’s what that actually means. ✅

Starting next season, teams can challenge ball-strike calls at parks that have the technology. It moves the automated strike zone from a limited Southeastern Conference tournament experiment into regular season play across the country.

The upside is real. The Southeastern Conference ran it this spring and it worked. 105 calls challenged, 59 overturned, catchers hit on 63% of theirs. The tech clearly works.

So why does it feel early to me? Two questions I keep coming back to:

If not every school can run it, why roll it out now? Whether a park gets ABS depends on if it has the equipment. That means some teams play with it and some don’t. Same sport, same season, different rules depending on where the game is played.

And who’s paying for it? These systems run $100K to $300K to install per stadium, plus $5K to $20K a year to license. For programs with resources, manageable. For everyone else, that’s exactly where the gap between the well-funded schools and the rest of college baseball can widen.

None of this makes it a bad idea. The tech works and the direction is probably right. I just want the access and cost questions answered before we call it a win for everybody.

If you follow college baseball, where do you land on this one?

Source: Baseball America

Every player in this photo has a different story. Different town, different road, different dream.For ninety seconds dow...
07/04/2026

Every player in this photo has a different story. Different town, different road, different dream.

For ninety seconds down that baseline, none of that matters. Same line. Same anthem. Same country that gave every one of us a shot to chase this game.

That is what today is about. I am proud to be an American, and proud of every family grinding toward their own version of it.

Happy Independence Day. 🇺🇸

Slumps are part of the game. Every hitter has them. The ones who last are not the ones who avoid the slump. They are the...
06/18/2026

Slumps are part of the game. Every hitter has them. The ones who last are not the ones who avoid the slump. They are the ones who do not rewrite their whole approach after one bad stretch.

Investing works the same way. Looking at the US market from 1926 through 2025, there were 75 positive years and 25 negative ones, averaging about 10.2% a year. Historically, most down years were followed by up years. The most recent example was a loss in 2022 followed by a strong 2023.

As the old saying goes, history does not always repeat, but it often rhymes. That is not a promise about any single year. But when I am helping a young player stay committed through the noise, it is a useful reminder of why we do not abandon a plan after one rough stretch.

That is the lesson from the field and from the market. Trust the process, and do not let one rough season pull you off your plan.

Source: Dimensional Fund Advisors. CRSP 1-10 Index Returns by Year, 1926 to 2025.

Past performance is no guarantee of future results. Investing risks include loss of principal and fluctuating value. There is no guarantee an investment strategy will be successful. Indices are not available for direct investment. Their performance does not reflect the expenses associated with the management of an actual portfolio.

In USD. Return in 1970 was 0.002%. CRSP data provided by the Center for Research in Security Prices, University of Chicago. The CRSP 1-10 Index measures the performance of the total US stock market, which it defines as the aggregate capitalization of all US securities listed on the NYSE, NYSE MKT (formerly AMEX), and Nasdaq Global Market.

Dimensional Fund Advisors LP is an investment advisor registered with the Securities and Exchange Commission.

Investment products: Not FDIC Insured, Not Bank Guaranteed, May Lose Value

A PhD scientist chose to be in a dugout instead of behind a computer screen.She could’ve kept working remotely with thou...
06/13/2026

A PhD scientist chose to be in a dugout instead of behind a computer screen.

She could’ve kept working remotely with thousands of athletes. She left that to grind with one team. Every day. In the weight room, on the mound, at practice.

WVU Baseball has force plates built into the pitching mound. Motion capture. Trackman in every cage. A full-time biomechanist who also teaches in the university’s sports science program.

That’s the college baseball landscape in 2026.

The choice between signing or going to school used to feel more straightforward. It’s more complicated now for a lot of reasons and player development infrastructure is one of them.

If you’ve spent your whole career developing at a top-tier facility, knowing what an organization’s process looks like on that side of the ball matters. It should be part of the conversation.

Most orgs have gotten better. But not all of them have, and you deserve to know the difference before you make one of the biggest decisions of your life.

Address

11611 N Meridian Street
Carmel, IN
46032

Telephone

+13175731754

Website

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