Welcome to Your Family CFO!

We’re Roman and Robert, partners at Upholdings, an emerging leader in modern wealth management. Every week, we’re in client meetings solving real problems: equity comp decisions, tax optimization, estate planning gaps, portfolio construction under real constraints. This Substack distills that work into insights for your own use.

What you’ll get:

  • Weekly, from Roman - planning strategies: cash flow, tax and compensation optimization, estate and legacy planning. Ways to keep more of what you earn.

  • Semi-quarterly, from Robert - investing notes: our insights into what’s driving the market, and which securities are best positioned to benefit.

This is the actual playbook we run and it is ever changing.

Who is Upholdings?

Upholdings is a private wealth firm built around clarity and intentional decision-making. The firm serves high-net-worth clients who are dedicated to continuous building.

Robert Cantwell III

Robert founded Upholdings after years in both the fund management and startup world. After witnessing smart, well-compensated people make costly mistakes with their equity, taxes, and estate, he set out to build a firm that could sit at the center and enable better decisions. He is a Harvard grad and lives in Nashville with his family.

Roman Puglise, CFP®

Roman leads financial planning at Upholdings, bringing an ultra-high-net-worth approach to clients who are still building their wealth. A former All-American and National Champion lacrosse player at Maryland, he brings that same team-first drive to every client relationship. He lives in Charleston with his wife and son.


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Disclosures: Upholdings Group LLC is a registered investment adviser located in Nashville, TN. This newsletter is for educational purposes only and is not personalized investment, tax, or legal advice or an offer to provide services. Investing involves risk, including loss of principal. Past performance does not guarantee future results. Registration does not imply a certain level of skill or training.

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Real tactics, insights, and strategies from the owners building a modern private wealth practice, simplified for the DIY investor.

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