Go back to PE/VC or Stay in Family Biz + Real Estate?

Navigating this kind of career crossroads can be challenging, but based on the most helpful WSO content, here’s how you might approach your situation:

1. Entrepreneurship Not Meeting Expectations – How to Pivot?

• Many professionals in PE/VC have faced similar moments where entrepreneurship didn’t align with their expectations. For example, in the "THEN and NOW: CompBanker thread, a user shared how they weighed the cost/benefit of staying in PE versus pursuing a lifestyle business. They ultimately decided to stay in PE, noting that entrepreneurship would always remain an option later in life. This highlights the importance of assessing whether the timing and structure of your entrepreneurial ventures align with your long-term goals.
• If you’re finding the family business and side hustle misaligned with your aspirations, it’s okay to pivot. The key is to be honest with yourself about what you want out of life and whether these ventures are the best way to get there.

2. Would Leaving Both Roles Now Damage Credibility or Optionality?

• Leaving roles after a short stint can raise questions, but it’s not necessarily a dealbreaker. In the "Q&A: Returning to PE After a Year and a Half at a Series C Startup" thread, a user shared how they transitioned back to PE after a brief detour into a startup. They emphasized framing the experience as a learning opportunity and focusing on how it added to their skillset.
• If you decide to leave, position your narrative around the skills you’ve gained (e.g., operational experience, entrepreneurial insights) and how they make you a stronger candidate for institutional investing. Highlighting your ability to adapt and learn from diverse experiences can mitigate concerns about short tenures.

3. Evaluating Institutional Investing vs. Sticking It Out

• To decide whether to return to PE/VC or stick it out, consider the following:
  • Long-Term Goals: What do you ultimately want from your career? If institutional investing aligns more closely with your aspirations, it might be worth exploring a return sooner rather than later.
  • Opportunity Cost: As highlighted in the "Private Equity or Pizza Equity?" thread, the earlier in your career you take risks or make pivots, the less costly they tend to be. Waiting too long could limit your flexibility, especially as personal and financial commitments grow.
  • Current Situation: If the family business is burning cash and the side hustle isn’t aligned with your interests, it may not be worth sticking it out for another year unless you see a clear path to turning things around.

Final Thoughts:

• It’s okay to step back and reassess. Many professionals in PE/VC have taken detours and returned stronger. The key is to craft a compelling narrative about your journey, focusing on the skills and insights you’ve gained.
• If you’re leaning toward returning to institutional investing, start networking and exploring opportunities now. As noted in the "Private Equity vs. Venture Capital - Differences and Similarities" thread, networking and leveraging your past experience can open doors, even after a brief hiatus.

Ultimately, the decision should align with your long-term goals and personal values. Good luck!

Sources: Private Equity vs. Venture Capital in 2018, Family Office Private Equity, Q&A: Returning to PE After a Year and a Half at a Series C Startup, Family office Private Equity - help, Starting a Private Equity Fund/Firm