Joining a risky firm as a stepping stone in order to break into VC?

I have three years of experience working at a boutique real estate development firm backed by institutional capital. I aspire to transition into the field of VC in an investment-focused capacity. Over the past six months, I have diligently dedicated my efforts to networking within the industry and establishing valuable connections.

While my current company has enjoyed considerable success and a reputation and has equipped me with valuable investment experience, I find myself unsatisfied with the monotonous tasks inherent in real estate development, such as obtaining permits from the city and analyzing building plans. My ultimate aspiration is not to develop industrial warehouses and buildings but rather to secure capital for my own tech venture.

It's worth noting that I acknowledge a certain level of privilege in my situation due to a family member who serves as the founder of a Startup Studio, managing a portfolio of tech startups developed in-house. However, I have been deliberate in refraining from relying on this family connection as the sole catalyst for my career advancement. I must also admit that I am skeptical about the stability of companies and the firm's longevity within my family member's portfolio, given the inherent risks he has undertaken. There has also been lots of employee turnover in recent years, and the situation is not perfect.

Given my current progress in transitioning from real estate development into venture capital, I believe my chances of securing a role directly within a VC firm are relatively low, unless I first take a position that serves as a stepping stone into the VC industry. My preference is to explore opportunities where I can envision a long-term future, rather than potentially leaving after a few years. I would feel build guilt for leveraging my family connection as a means to an end.

On one hand, I am contemplating leaving my handsomely compensated position in RE development, and am considering leaving for a risky venture run by my family member in the means to break into the world of VC investing. I kindly seek advice from this forum on whether I should continue my search for opportunities at other startups if I don't see a permanent future at the role, or consider joining my family member's firm with a higher risk of failure as a potential stepping stone to my desired career in venture capital. I would appreciate any insights and perspectives. Thanks!


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