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Episode
375
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Should You Go Solo? Transitioning from Developer to Entrepreneur

Recorded:
May 20, 2025
Released:
June 3, 2025
Episode Number:
375

In this episode, Matt and Mike explore what it takes to transition from being a developer employee to becoming a tech founder or business owner. They break down how your personal situation—time, money, dependents, and hobbies—can impact your readiness to make the leap. This isn't just about technical skill. You’ll need to think strategically, handle business admin, understand local laws, and price your services or products properly. Plus, they ask a critical question: do you actually want to own a business, or would a different job be a better fit?

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Show Notes

1. Boiling It Down: Time and Money

  • Your ability to transition depends largely on how much time and money you have.
  • Evaluate responsibilities: kids, debt, partner’s income, lifestyle costs.
  • Examples:
    • Someone with savings, low expenses, and no dependents might take the leap now.
    • Someone with kids, a mortgage, and tight finances might need to transition more slowly.

2. Why Do You Want This?

  • Is your desire rooted in freedom, frustration, ambition, or something else?
  • Are you running from a bad job, or running toward a bigger purpose?
  • Would a different tech job (remote, higher pay, more autonomy) actually solve your problem?

3. It's Not Just About Tech Skills

  • Business ownership requires:
    • Strategic thinking
    • Business admin (invoicing, taxes, contracts, etc.)
    • Marketing and branding
    • Navigating legal structures (sole prop vs. incorporation)
    • Pricing and positioning
  • Learning to sell yourself or your product is often the biggest mindset shift.

4. Ways to Transition (Path Options)

  • Side Hustle Route: Keep your job and build something on the side.
  • Freelancing Bridge: Use freelancing as a stepping stone to full business ownership.
  • Burn the Ships: Quit cold turkey (high risk, needs high savings/prep).
  • Part-Time Employment: Go part-time to free up days for building your thing.

5. Common Pitfalls

  • Not budgeting for taxes or slow months.
  • Underestimating how long it takes to get clients or users.
  • Burning out by doing everything yourself without automation or outsourcing.

6. Mindset & Support Systems

  • You’ll need resilience—clients ghost, plans fail, platforms change.
  • Build a support system: other founders, mentors, a good accountant, maybe a therapist.
  • Impostor syndrome doesn’t stop when you become your own boss.



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