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My First Million

My First Million

The best business ideas come from noticing what's working and doing it better, faster, or for a different audience.

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Scale across multiple companies by being an effective chairman rather than trying to be CEO of everything

Serial entrepreneurs, studio operators, or investors who want to be actively involved across multiple ventures

Ongoing relationship management across company lifecycles

What Success Looks Like

CEOs who proactively reach out for guidance, successful financing rounds, strategic decisions made efficiently, and companies that can operate independently while benefiting from your oversight

Steps to Execute

1

Recruit specialist CEOs who know the industry better than you do

2

Establish weekly or bi-weekly check-in calls

3

Focus on high-level strategy, not day-to-day operations

4

Handle difficult situations (financing, pivots, personnel changes)

5

Provide network introductions and deal-making support

6

Stay available for urgent issues while avoiding micromanagement

Checklist

CEO recruitment process with industry-specific criteria
Regular communication cadence established
Clear division of responsibilities defined
Emergency escalation procedures in place
Board meeting schedule and materials process
Success metrics and reporting agreed upon

Inputs Needed

  • Strong network for CEO recruitment
  • Time for regular check-ins and urgent issues
  • Industry knowledge to provide valuable guidance
  • Patience to let CEOs learn and make mistakes

Outputs

  • Successfully operating companies with minimal day-to-day involvement
  • CEOs who develop independence while utilizing your strengths
  • Efficient problem-solving for complex issues
  • Sustainable scaling across multiple ventures

Example

Business Insider chairman relationship where Henry Blodgett handles all editorial and operational decisions, while Kevin Ryan handles financing, acquisitions, and strategic pivots.