Financial planner and former college admissions consultant Tyler West joins The College Investor Audio Show at MilMoneyCon to talk about how families should actually approach paying for college — from 529 plans to commuter schools to the conversations parents aren't having with their kids.
Recorded live at MilMoneyCon, Robert Farrington sits down with Tyler West, an associate financial planner at CL Sheldon & Company who works with military and veteran families. Before financial planning, Tyler served in the Army, worked in higher ed at the University of Colorado, and ran his own college planning business advising high-net-worth families on admissions and financial aid.
His central message: families spend too much energy optimizing the savings vehicle and not enough on the conversation that actually determines whether the money is well spent.
Episode Summary
- Why the 529 plan isn't the automatic right answer for every family
- The "donut hole" problem facing middle-class families who don't qualify for need-based aid
- Why completion rate matters more than prestige (only 49% of students who start a four-year degree ever finish one)
- How to use the reach/match/safety framework on both admissions and affordability
- Why Parent PLUS loans can quietly destroy families
- The graduate school loan caps taking effect July 1 — and why grad school is where the real debt damage happens
Start With The Conversation, Not The Account
Tyler's pushback on the standard financial planner playbook: most families default to opening a 529 plan and contributing "an appropriate amount" without ever discussing what the kid actually wants to do. His advice is to start career conversations early (at the dinner table, with family and friends in different professions) because most high schoolers can only name between six and 12 careers, and they tend to pick what their parents do.
The 529 Plan Trade-Off
The 529 plan is a fine tool, but Tyler warns families to weigh the state tax deduction against the flexibility cost. Investment options are limited, and not every state's rules align with federal rules — California, for example, doesn't recognize the 529-to-Roth IRA rollover, so a rollover triggers state tax plus a penalty.
For high-income families, the financial aid math also matters less than they think: once you cross a certain income and asset threshold, you're paying sticker price regardless of what account you used.
Reach, Match, Safety (On The Price Too)
Tyler recommends families build an admissions safety and a financial safety. Commuting, in-state public schools, and dual enrollment to graduate early (or with two degrees) are underrated cost-cutters. Sticker price isn't real for most families, but it is real for the upper-middle "donut hole" that misses both Pell Grants and need-based aid.
Student Loan Rule
Tyler's hard rule: never borrow more than the student's expected first-year salary. The bigger danger is Parent PLUS — there's no legal obligation for the child to pay it back, and it can pull from parents' prime compounding years to subsidize a degree the family couldn't otherwise afford.
Bottom Line
The savings vehicle matters less than the conversation. Sit down with your kid, figure out what they actually want to do, and let the financial plan follow from there.
Don't Miss These Other Stories:
Colin Graves is a financial writer and editor with more than 20 years of experience in banking and wealth management. Before joining The College Investor, he managed retail and commercial portfolios exceeding $1 billion, earning multiple awards for leadership and customer service. Colin holds several credentials from the Canadian Securities Institute, including the Canadian Securities Course, Professional Financial Planning Course, and the Certificate of Financial Services Advice.
Today, he applies that expertise to editing and writing about investing, credit, and money management for readers seeking practical, trustworthy financial information. Colin also writes at ColinGraves.com, where he helps people transition from traditional employment to self-employment through financial literacy and business coaching.