"The best way to verify if you can trust somebody is to trust them."
Ernest Hemingway
In 1995, Pierre Omidyar listed a broken laser pointer for sale online. That modest $14.83 transaction became the first of billions on what we now know as eBay. This seemingly insignificant act exemplifies a powerful principle: transformative success often begins with small, calculated risks.
The Philosophy of Small Bets
Nature itself innovates through small iterations. Evolution proceeds through tiny mutations rather than giant leaps, and similarly, personal and professional growth happens through small experiments rather than massive gambles. This approach creates what Nassim Taleb calls an "antifragile" system—one that doesn't just survive uncertainty but grows stronger from it.
The power of small bets lies in their unique combination of limited downside and unlimited upside potential. When you make small bets, you're not just taking less risk—you're creating more opportunities for positive Black Swan events while protecting yourself from catastrophic losses.
The Zomato Story: Small Bets in Action
Consider the story of Deepinder Goyal, who in 2008 noticed his colleagues in Delhi wasting time standing in lines to look at restaurant menus. His solution wasn't grandiose—he simply started scanning menu cards and posting them on his office intranet. This tiny initial investment of time and effort eventually grew into Zomato, a global food delivery giant.
Zomato's growth illustrates the power of sequential small bets:
Menu Scanning (2008)
Investment: Minutes of time and access to a scanner
Learning: People valued easy access to menu information
Foodiebay Website Launch
Investment: Basic website hosting
Learning: The problem existed beyond his office
City Expansion
Investment: Travel and relationship building
Learning: The model could scale to different markets
Adding Reviews and Features
Investment: Incremental development
Learning: Users wanted a comprehensive food platform
The beauty of this approach becomes clear when you look at the risks:
If the menu scanning failed? Just stop scanning.
If the website failed? Shut it down and move on.
If a new city failed? Retreat to successful markets.
This is how antifragile systems work. Each small bet either:
Succeeds and opens new opportunities
Fails and provides valuable information
Breaks even but teaches important lessons
Building an Antifragile System
The true power of small bets lies not in their individual size but in their systematic application. Here's how to build this approach into your life:
1. Create a Portfolio of Experiments
Instead of making one big bet, distribute your risks:
Test multiple career paths through side projects
Try different learning methods before committing to expensive education
Launch several small product features rather than one big release
2. Implement the Feedback Loop
Make a small bet
Collect data quickly
Learn from results
Adjust your approach
Repeat with improvements
This creates a self-reinforcing system that becomes stronger with each iteration.
3. Follow the 1% Rule
Never risk more than 1% of your available resources (time, money, energy) on a single experiment. This ensures:
No single failure can be catastrophic
You have enough attempts to find what works
You benefit from compound learning
Your system remains antifragile throughout
Practical Applications
In Career Development:
Volunteer for small projects outside your current role
Start a minimal consulting practice with one client
Write weekly about your industry insights
In Business:
Test new products with a small customer segment
Experiment with pricing in limited markets
Try new marketing channels with minimal budgets
In Personal Growth:
Learn new skills through 30-minute daily practices
Test different routines for one week each
Build habits using the "2-minute rule"
The Small Bets Checklist
Before making any bet, ask:
Is the downside truly limited?
Will I learn something valuable regardless of outcome?
Can this be scaled if successful?
Is there potential for unexpected upside?
Making It Systematic and Make it Obvious
Keep a "Small Bets Journal"
Schedule regular review and launch times
Place visual reminders of current experiments
Make it Attractive
Focus on areas of natural interest
Share experiments with accountability partners
Celebrate learning, not just winning
Make it Easy
Break down larger goals into micro-experiments
Use templates for tracking and evaluation
Start smaller than you think necessary
Make it Satisfying
Document lessons learned
Build a "Wins Wall" of successful experiments
Share insights with others
Success rarely comes from one big decision but rather from the compound effect of many tiny, well-structured experiments. Like Omidyar's broken laser pointer or Goyal's scanned menus, the smallest bet could lead to the biggest breakthrough.
The real magic of small bets isn't in their size—it's in their sequence. Each bet should:
Answer a specific question
Risk little if it fails
Teach something valuable
Position you for the next opportunity
The goal isn't to avoid failure—it's to make failure cheap and learning valuable. Start with something so small it seems insignificant. Test quickly. Learn continuously. Adjust based on feedback. This is how you build not just success, but an antifragile life that grows stronger with every challenge.
Remember: You don't need to see the entire staircase. You just need to see the next step. What's your next small bet?
Till next week...
Nic