By name: entrepreneurship description: | Startup and business building principles. Use when: - Deciding between bootstrapping vs VC funding - Building a small, profitable business - Thinking about team size and growth path - Evaluating if an idea is "venture-scale"
Entrepreneurship Principles
Bootstrapping vs Venture Capital
Both paths are valid — choose what fits your situation.
| Factor | Bootstrapping | Venture Capital |
|---|---|---|
| Control | Full | Shared with investors |
| Speed | Slower, organic | Faster, fueled by capital |
| Risk | Personal only | Shared |
| Exit | Profit, lifestyle | Scale or bust |
| Example | 37signals | Uber, Airbnb |
Small Team Advantage
Small is not a stepping stone — small is a destination.
- 37signals: 75 employees, profitable for 24 years
- Asana: 1,600+ employees, still pursuing growth
- Key insight: Profit > revenue metrics
Constraints as Advantage
- Limits bring clarity and focus
- Two-person teams for features
- Max 6-week delivery cycles
- No salespeople, no complex pricing
Success Metrics
The ultimate question: "Would you want to do this again?"
- If "Yes, that was fun, let's do it again" = Success
- Profit is fuel for the next thing
- Not everything needs to be measured
When to Raise Capital
You probably don't need VC if:
- Software business with healthy margins
- No hardware/factory requirements
- Can acquire customers organically
You might need capital if:
- Hardware products
- Heavy infrastructure needs
- Regulatory hurdles requiring war chest
Venture-Scale Check
Ask yourself:
- Can this be a $1B+ company?
- Is there a path to dominate a market?
- Are you willing to sacrifice control for speed?
If no to most, bootstrapping may be your path.
Sources
- Jason Fried (37signals)
- Lenny's Podcast interviews