The Stacking Benjamins Show

How to Make Your Money Support the Life You Want (SB1793)

10 snips
Jan 21, 2026
Join Dana Anspach, a certified financial planner and retirement expert, alongside Andy Hill, author and creator of the 'Marriage, Kids & Money' podcast. They explore how to prioritize family and flexibility through financial planning. Andy shares his journey from corporate life to a three-day workweek, emphasizing time freedom. Dana dives into life insurance myths following the Kyle Busch lawsuit, clarifying Indexed Universal Life policies and the importance of choosing insurance based on personal goals rather than sales pitches.
Ask episode
AI Snips
Chapters
Books
Transcript
Episode notes
ANECDOTE

Leaving Corporate For Family Time

  • Andy Hill felt trapped by a corporate career and missed important family moments before quitting in January 2020.
  • He built a side hustle for four years, had a year's runway saved, and then fully transitioned to solopreneurship.
ADVICE

Playtest And Build Runway First

  • Playtest side hustles before quitting your job to validate demand and fit.
  • Save a runway (Andy recommends about 12 months of expenses) to reduce risk during transition.
ANECDOTE

Pandemic Shock Tested The Plan

  • Andy's first months after quitting in Jan 2020 were great until the pandemic wiped out contracts in March.
  • His 12-month runway covered three to four months and allowed pivoting rather than failure.
Get the Snipd Podcast app to discover more snips from this episode
Get the app