Military to Civilian Transitions with Jesse Cramer, Personal Finance for Long-Term Investors

Spencer Reese, founder of the Military Money Manual, joins Jesse Kramer to discuss the unique financial landscape of military service and the critical transition to post-service life. Spencer separated from the US Air Force in 2022 after 12 years as a pilot and now helps military families reach financial independence through his book, podcast, course, and website.


Host: Jesse Kramer - Financial adviser and host of "Personal Finance for Long-Term Investors"


Guest: Spencer Reese - Former Air Force pilot (12 years active duty), founder of Military Money Manual, author, podcaster
Key Topics Covered

Military-Specific Financial Challenges:


• Lower enlisted income but essential expenses covered (housing, food, healthcare)

• The "lieutenant mobile" trap - buying too much car relative to rank/income

• Transparent pay structure creates unique comparison pressures

• Status games vs. wealth building: Why the cheapest car often belongs to the colonel

• Split around captain rank - some choose optimization, others choose lifestyle inflation


Creating Financial Systems:


• Spencer's personal story: Living paycheck to paycheck early in marriage with $20 every two weeks for discretionary spending

• How his wife forced financial discipline and communication

• The 30-day test: Could your finances run on autopilot for a month?

• Critical for deployments when internet access may be limited

• Automate everything: bills, investments, transfers


Deployment as Financial Opportunity:


• Tax-free pay in combat zones

• Zero housing/food expenses while deployed

• Spouse can potentially reduce expenses (move home, downsize)

• Real example: Service member paid off all auto and student loans in 3 months of deployment

• Life-changing potential of a single 9-12 month deployment if leveraged strategically


Common Behavioral Traps:


• Most military families are "avoiders" - have the will but lack the skills

• Money wasn't discussed at home growing up, never learned the basics

• Two avoiders marry each other and perpetuate the cycle

• The mistake: Thinking low income is the problem when it's actually overspending on cars


Free Military Resources Available:


• Military OneSource - Free financial counseling specific to your situation

• Airman and Family Readiness Center (each branch has equivalent)

• Face-to-face budget help and financial planning on every base

• No excuse not to use these resources

• Success stories: Enlisted millionaires before 20 years, airmen with $100K after 4-year enlistment


Military vs. Civilian Pay Reality:


• Officers hit six figures around captain rank

• Buying too much car is easily a 5-6 figure mistake over time

• When you're making five figures, you can't afford five-figure mistakes

• One good decision (avoiding expensive car) creates massive wealth-building opportunity


The Post-Service Transition Crisis:


• Spencer's story: Left active duty before 20-year retirement, thought side business would be enough

• Financially prepared (large nest egg, near financial independence)

• Completely unprepared for loss of purpose and meaning

• Got depressed for months after separation

• Taking airline job helped initially, but quit after 6 months - still wasn't fulfilling

• The money isn't the hard part - finding purpose is


Purpose and Meaning in Retirement:


• Pre-retirees rank finances as top priority

• 2-10 years into retirement, lifestyle issues become the top concern

• The workplace provided: paycheck (replaceable), purpose (harder to replace), socialization (often overlooked)

• "What's your job when every dollar has a job?"

• Reference to "The Second Mountain" by David Brooks - four callings: vocation, religion/philosophy, community, marriage


Practical Transition Advice:


• TAP (Transition Assistance Program) - Available starting one year before separation

• Spencer's mistake: Only went once, should have gone twice (at one year out AND closer to separation)

• Too much information to absorb in one session

• Free LinkedIn Premium for a year (included)

• Go early to start the mental transition process

• Guard/Reserve option as a "slow transition" - maintain community while easing into civilian life


The "Not Work" Trap:


• Like high school freshman saying "I'll just do not school this summer"

• Many retirees approach retirement as "I'll just do not work"

• Leads to undefined path and potential struggle

• Better to ease into it with preparation and ex...