Should You Start A Startup?

Key Takeaways

Resilience is the most important quality for startup founders, more than intelligence, charisma, or past professional success
Initial motivations for starting a startup are less important than developing enduring motivations over time
Before starting a startup, honestly assess what you stand to lose and if you can handle the worst-case scenario
Starting a startup provides valuable learning experiences that can enhance career opportunities even if the venture fails
Finding a co-founder you enjoy working with and can develop ideas with is critical to startup success

There is no simple test to determine who will become a successful startup founder
Stereotypical founder traits (brilliant programmer, charismatic product genius) can help but aren't prerequisites
Many different types of people succeed as startup founders with varying strengths
Experienced investors still get surprised by who turns out to be a great founder
Academic or corporate success doesn't reliably predict startup success
Startups require pushing through personal rejection and struggle unlike corporate work

Resilience is the most crucial quality for startup founders to persevere through challenges
Confidence doesn't equal resilience - some confident-seeming founders lack staying power
Quiet, less confident-seeming founders often demonstrate surprising resilience
Example: Benchling founders appeared unconfident but showed remarkable resilience
- Took two years after YC to develop revenue streams
- Transformed from soft-spoken engineers to leaders of a $6+ billion company
- Overcame skepticism about their ability to handle enterprise sales

Initial motivations for starting a startup matter less than expected
Many legitimate reasons to start a company exist, including:
- Desire to become wealthy (startups can generate life-changing money quickly)
- Simple curiosity about the experience
Founder motivations often evolve over time
- Some founders plan to sell quickly but end up running companies for decades
Enduring motivations develop with time:
- Genuine interest in the problem being solved
- Love for the people you're working with

Honestly assess what you have to lose by starting a startup
Calculate your personal worst-case scenario and determine if it's acceptable
- Consider that startups typically need at least a year of commitment
- Factor in opportunity costs based on your career stage
Recognize the educational value of startup experience regardless of outcome
- Startup founders gain experience across multiple domains (sales, product, support)
- This helps clarify what type of work you enjoy
- Companies value former founders as employees (examples: Rippling, Airbnb)

Failed startup experience is valued by many employers
Companies specifically seek candidates with startup experience
- Perceived as self-starters who take initiative
Example: Rippling (valued at $10B) actively recruits former founders
- Places them in charge of product divisions as general managers
- Has approximately 50 former founders working there
Example: Nick Grandy's career path
- First startup (Wonderbar) shut down
- Became Airbnb's first employee
- Eventually founded Outschool (valued at $3B+)

Two essential elements needed: an idea and a co-founder
Finding ideas and co-founders should be approached as interconnected tasks
Best ideas often emerge from conversations with smart people
Identify friends/colleagues who stimulate your thinking
- People you enjoy discussing ideas with
- Colleagues who make you more productive
Have regular conversations about ideas, technologies, and products
Research and learn between conversations to develop your thinking

Change your environment if you lack idea-oriented peers
Working at a startup provides:
- Insider knowledge of startup operations
- Access to less risk-averse potential co-founders
College graduates should consider startup jobs
Current Fang employees might transition to startups

Turn interesting ideas into weekend projects
Build simple prototypes to experience turning ideas into reality
Develop necessary skills, especially programming
- Non-programmers should learn basic coding
- Only need enough skills to build a version 1
Monitor user reactions to your side projects
- Look for passionate users rather than large numbers
- "Better to make a product that a few people really love than one a lot of people are indifferent towards"

Pay attention to your energy and enjoyment levels
- If your job drains you but side projects energize you, it may be time to quit
Focus on how much you enjoy the process of creating
Consider the quality of collaboration with side project partners
- Finding a great potential co-founder is rare and valuable
The decision to start a company should consider:
- Your comfort with worst-case scenarios
- Whether you have compelling ideas to explore
- If you've found someone you work well with who shares your ambitions

Don't overthink initial motivations - they evolve over time
Curiosity about startups is sufficient motivation to begin
Assess and accept your personal worst-case scenario
Seek out smart collaborators for idea discussions
Launch small side projects to gain experience
If you find someone you enjoy working with and both want to start a company, take the leap