Inside the Family Office: The Chief of Staff Role with Donald J Cunningham

Guest: Donald J Cunningham, Head of Family Office for a senior member of the Qatari royal family

Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview

When your principal has virtually unlimited resources, the answer to almost every request is yes. That makes the job less about getting things done and more about knowing when, and how, to push back. Donald J Cunningham explains how the Chief of Staff role works inside a single family office, where there's no institution to hide behind and no clean line between the portfolio and the principal's personal life.

About Donald J Cunningham

Donald spent the first half of his career in capital markets and lower mid-market M&A, then hit a crisis of confidence about where it was headed. Friends kept telling him he'd make a great "person behind the person," so one restless night at 2am he applied to an obscure Indeed listing, calling himself a "recovering investment banker" in the cover letter. That led to seven years at a well-known hedge fund founder's family office in New York. He now leads the family office for his fourth principal, splitting his time between London and New York.

Key Takeaways

- Privacy isn't secrecy. The best principals are discreet and humble, and the high hedges around family offices are intentional. Don't expect them to come down, even as the industry adds more governance.

- There's no room for ego. Family offices run lean, often inside or next to the principal's home. If a toilet overflows, it doesn't matter whether you're the CIO or the housekeeper. Good family offices test for this in the interview.

- Three tools for advising a principal who can say yes to anything: name the trade-off (yes, but at the expense of what?), use the rule of three (say "I think this is a bad idea" three times with reasons, then execute), and anchor to the long term with a family charter or investment policy.

- Interview the principal as much as they interview you. Ask about their values, what keeps them up at night, and what happens when things go wrong. Prestige means nothing if the fit doesn't work, and red flags in the interview rarely go away.

- Corporate Chiefs of Staff being pulled into an executive's personal affairs should read it as trust, not a demotion. After a liquidity event, it can be an opening to help stand up a private office.

- The career path is horizontal. There's no associate-to-VP ladder in a family office. The reward is exposure, variety, and more delegation as trust grows.

Join the Chief of Staff Network

The Chief of Staff Network is where this conversation continues, through events, connections, and conversations with Chiefs of Staff in corporate, public sector, and family office roles. Find it at chiefofstaff.network.