Real Estate: Entrepreneur vs Corporate Star

A dream of many w2 real estate professionals (myself included) is to one day start their own development/investment company. The surface level appeal is sexy: build your own brand, no more reporting to the corporate office or answering to your boss, and potentially make way more money then you ever would as an employee. But, there are serious risks, including, personal guarantees, risking your own capital, not hitting your underwritten returns, and now instead of answering to your boss, you’re courting investors. Overall, higher highs and lower lows.

Would anyone argue that climbing the corporate ladder to an MD level position is a better deal? Instead of putting your own personal capital and reputation at risk, collect a nice annual comp and play it safe? I worry about looking back at my career 30 years from now and regretting playing it safe.

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To me it's a silly question - somebody who is a true entrepreneur who is going to open their own shop wouldn't even consider the idea of staying in corporate long-term. It's a completely different lifestyle and if you're built to run your own company, you have no interest in playing it safe. Very different paths for different personalities.

What a lot of people underestimate about going out on your own is the amount of work that entails. You're not reporting to anyone, but you're going to put in longer, harder hours than you ever did on the corporate side because it is YOUR BUSINESS and you will care about it more, not to mention the harder work it will take to get it off the ground. I can count the number of successful entrepreneurs I know who aren't absolute workaholics on one hand.

The question here is do you want to put your life into your own business and possibly fail but also possibly create something meaningful, build a legacy, and get rich? Or are you happy working your way up the corporate ladder, risking little to none of your own money, and collecting a solid pay cheque but not building a legacy or ever realizing massive wealth. I know the latter sounds a lot less sexy, but for 99% of people its the right answer.

 

Personally I’m good with a stable upper middle class income. I don’t want to fly private or have additional houses. Also, if all goes well as an entrepreneur, you have to work really hard not to let it ruin you and your kids. No thanks. 

 

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