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Based on the most helpful WSO content, here are some insights on choosing between Hedge Funds (L/S) and Entrepreneurship, especially when optimizing for long-term freedom:

Long-Term Freedom: L/S vs. Entrepreneurship

1. Entrepreneurship:

   • Autonomy and Happiness: Entrepreneurs generally have significantly more autonomy. Science shows that most entrepreneurs are generally happier than employees, primarily due to this reason, even if they work similar or more hours.
   • Purpose and Upside Potential: The risk of foregoing short-term cash flows from a W2 paycheck is often offset by a greater feeling of purpose and potential for life-changing upside potential. There's a 35% chance that the money will follow.
   • Active Investment: Investing in your own business is considered the ultimate active investment. It allows for a greater sense of control and personal fulfillment.

2. Hedge Funds (L/S):

   • Risk and Reward: Investment Banks typically attract more risk-averse individuals, while entrepreneurship is the complete opposite. Hedge Funds, particularly Long/Short (L/S) strategies, can offer substantial financial rewards but come with their own set of risks and pressures.
   • Work-Life Balance: The buyside opportunities (PE, HF, VC) are appealing but often come with demanding work schedules and high stress, which might not align with the desire for long-term freedom.

Anecdotes and Considerations:

• Entrepreneurial Success: Many successful entrepreneurs have found that the skills and work ethic developed in finance can provide excellent chances to make things work when running a small business.
• Freedom and Flexibility: Entrepreneurship offers the potential for greater freedom and flexibility, allowing you to set your own schedule and work on projects that you are passionate about.

Conclusion:

• Entrepreneurship seems to provide more long-term freedom and personal fulfillment compared to L/S strategies in Hedge Funds. It allows for greater autonomy, a sense of purpose, and the potential for significant financial upside.

For more detailed discussions and personal anecdotes, you might want to explore the following threads on WSO: - https://www.wallstreetoasis.com/forum/investment-banking/overlooked-tru…</a">Why You Should Launch a Startup Instead of Going to the Buyside - https://www.wallstreetoasis.com/forum/real-estate/best-path-for-re-entr…</a">Breakdown of Post-IB Exit Opportunities

These resources can provide further insights and help you make an informed decision.

Sources: Best Path for RE Entrepreneur, Why You Should Launch a Startup Instead of Going to the Buyside, Entrepreneurship or IB... How do you choose?, Why You Should Launch a Startup Instead of Going to the Buyside, Breakdown of Post-IB Exit Opportunities