HoldCo Builders How I Retired at 30 as a Family Office Investor (Here Are the Investments I've Made)
Nov 20, 2025
Akshay Ramachandran, a retired family office investor and advocate of buy-and-hold strategies, shares his journey from Wall Street to spirituality. He delves into the intricacies of his analysis framework, highlighting his success with Carvana and the importance of thinking long-term. Akshay discusses the balance between financial acumen and Buddhist practices, revealing how meditation transformed his investment perspective. With insights on defining retirement and when to sell, he blends the worlds of finance and spirituality, offering a unique outlook for aspiring investors.
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Retirement As A Return Rate
- Retirement equals your annual cost of living divided by your net worth, which defines the return rate your portfolio must generate.
- Akshay treats retirement as fluid and impermanent, not a fixed state tied to career status.
From Immigrant Frugality To Value Investing
- Akshay grew up with an immigrant thrift mentality that made value investing feel natural to him.
- He studied finance at NYU, worked in restructuring banking, then joined a family office as a generalist analyst.
Learn A Business By Doing Deep First-Day Work
- Spend concentrated time learning each company: read filings, transcripts, and annual reports and answer core questions about the business.
- Use those routines to understand why you would own or short a company before making decisions.