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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

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Depends on how you define freedom. Is the goal to grind now and accumulate enough wealth quickly to "FIRE"? If that's the case, then go with the HF, ratchet up your savings rate, and hope you can not only survive, but also get lucky with a few big bonuses. If freedom is being able to roll into work late, set your own schedule, travel when you want, not have a PM breathing over your shoulder, but also having an incredible amount of responsibility with little reprieve then buying a business could be the path. Context is important too-- how much $$$ do you have saved, do you have family financial support, do you have kids etc. Happy to discuss privately as someone who wanted to go the HF route but ended up on the business path (albeit as part of a family business, so I had a lot of support / didn't need to take on much risk).

 
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Happy to answer more specifically in private with the major caveat there will be much greater variability in outcomes going the business route than simply going to work at a fund, where the jobs are basically the same firm to firm and the people all graduated from same three business schools. My time has been interesting, both good and bad; I love the freedom per the above but there is a lot of crap that you have to deal with every day. When you have a job, you have a reasonably set list of responsibilities and someone telling you what to do; there's not much else to worry about if you do your job. Tech problem? Email the helpdesk. Company gets sued? Let the legal department handle it. When you own a [smaller] business, everything falls on your plate at the end of the day. Some people will relish in tackling these new challenges every day, others would better enjoy staying within the confines of a pre-set job. Also, our businesses are industrial/manufacturing/factory type stuff. Managing a team of factory workers could not be more different than working on a team of white collar, highly educated MBAs.  

 

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