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My First Million

My First Million

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Find and manage a proactive tax professional who provides strategic value year-round

High-income individuals paying $100K+ annually in taxes who want optimization beyond basic compliance

3-6 months for selection, ongoing relationship

What Success Looks Like

Quarterly strategic tax planning sessions, proactive recommendations, and significant annual tax savings that exceed professional fees

Steps to Execute

1

Create comprehensive data room with current tax situation

2

Define specific requirements (strategy + compliance + bill pay)

3

Interview 5+ tax professionals with identical brief

4

Evaluate responses for proactive recommendations vs reactive compliance

5

Negotiate scope of services and communication expectations

6

Establish quarterly review schedule with specific deliverables

Checklist

Prior 3 years tax returns compiled
Current year estimated income/deductions documented
Entity structure flowchart created
Specific pain points and goals defined
Interview questions standardized across candidates
Fee structure and scope clearly negotiated

Inputs Needed

  • Historical tax returns and financial statements
  • Business entity documentation
  • Investment account statements
  • Clear definition of desired service level

Outputs

  • Year-round tax strategic guidance
  • Proactive planning recommendations
  • Reduced year-end tax stress
  • Potentially significant tax savings

Example

“Business owner paying $300K annually in taxes creates data room, interviews 6 firms, selects one offering quarterly strategy sessions and proactive planning, resulting in $50K annual savings and eliminated year-end stress.”