This episode of Wealthyist, hosted by Brandon Lehman of Annex Wealth Management,is based on his recent observations from eight weeks of work-related travel.

Central Question: "What’s Next After Retirement?"

1. • Lehman notes a recurring question from successful executives nearing retirement: “What do I do next?” Many have thrived in corporate life, amassed wealth, and are ready to leave the 9-to-5, but they still want to work in some capacity.
   • A common follow-up is whether to follow a friend’s lead into consulting. Lehman suggests “yes” if they want to keep working, as consulting offers flexibility (e.g., walking away when desired) and tax advantages (e.g., 1099 income, solo 401(k)s, write-offs for business expenses like cars or travel). He finds these planning discussions “a blast” as they open up creative tax strategies unavailable with W-2 income.
2. Observation 1: Trend of Registering Vehicles in Montana
   • Lehman observes wealthy individuals increasingly registering high-end cars (e.g., Porsches, Bugattis) and private planes in Montana, despite living far from the state. Reasons include:
     • Privacy: Montana LLCs hide ownership details.
     • Tax Benefits: No sales tax, lower registration fees, no use or property tax for planes, and no emissions testing (e.g., for diesel trucks).
   • He doesn’t condone this but reports it as a trend, noting some states are cracking down on it as a form of tax evasion.
3. Observation 2: Spring Cleaning and Document Retention
   • With tax season wrapping up, Lehman discusses document management:
     • IRS recommends keeping tax returns for 3 years (6 years if income is underreported by 25%, 7 years for bad debt/losses, indefinitely for fraud or non-filing).
     • He scans and encrypts his records digitally, suggesting listeners do the same to go paperless.
     • Post-2011 brokerage statements can be shredded since firms like Schwab retain digital copies.
   • For shredding, he advises using secure services with locked bins, chain-of-custody tracking, and cross-cut/micro-cut shredders (not strip-cut).