You are one of the most successful business leaders in the world. The owner and CEO of your own fortune 500 company, you have risen from humble beginnings to be a leader with businesses that span the globe and a financial position worth billions.

You appear on the major business lists, give a limited number of keynotes, and sit on two non-profit boards focused on energy access and small-business scaling in emerging markets. You have never been the subject of a serious governance scandal. Competitors respect the discipline of the balance sheet; employees talk about the fact that you still remember names from the early warehouses.

You keep a primary residence in a city with a major airport and a second, quieter place near water. Weekends, involve cooking (you still bake), long walks, and a modest art collection focused on contemporary Latin American and Asian work. You do not perform luxury; you use it when it buys time or access.

You rose from a bakery schedule and a folding table of used electronics to a company that moves energy, goods, and capital across continents. The story is not that you “made it.” It is that you still run the place as if the next payroll and the next grid contract both matter equally—because, to you, they always have.

Now, a list of your private holdings includes but is not limited to:

Operating & investment holdings

• Controlling (or majority) stake in Riverside Group and its four operating pillars

• Direct and carried interest in Riverside Ventures fund vehicles

• Minority stakes in a small number of late-stage climate, logistics, and industrial-tech companies

• Diversified public-market portfolio (index funds, selected large-cap energy/industrials, Treasuries and short-duration credit)

• Private credit and co-investment allocations through two or three long-standing family-office relationships

Real estate

• Primary residence in a major-hub city (discreet, high-security building or compound; not a landmark address)

• Second home near water, used for weekends and recovery. You have been looking at purchasing a small island somewhere tropical.

• One modest international pied-à-terre in a city where the company has heavy operations (e.g., London, Singapore, or Santiago)

• Small commercial or industrial properties held personally or through a holding company (legacy warehouses, a small office building)

Personal-use assets

• Fractional or whole ownership of a midsize business jet (or a long-term charter relationship that functions like ownership)

• Small, well-chosen vehicle collection: two or three daily drivers plus one weekend car; nothing theatrical

• A capable but not palatial boat kept at the second home

• Serious but focused art collection (contemporary Latin American and Asian work, a few mid-century pieces) with proper insurance and storage

• Watches and jewelry kept to a short, high-quality list rather than a display collection

Liquidity & structures

• Substantial cash and Treasury position sized for several years of personal and opportunistic capital needs

• Revocable living trust, irrevocable trusts for family, and a donor-advised fund or private foundation for philanthropy

• Captive or closely held insurance structures for certain operating and personal risks

• Personal line of credit and securities-backed facilities that are almost never drawn

Access & soft assets

• Long-standing relationships with two or three private banks and one independent multi-family office

• Memberships that actually get used: one city club, one industry-heavy policy forum, one discreet sports or sailing club

• A small, trusted personal staff (chief of staff / family office lead, security coordinator, household manager) rather than a large household

People you may run into (scenarios 1-9 in order) :

Cara and Eloise, having some car trouble in the morning!

Nancy is hoping your company will provide a scholarship.

Ian's sister is in hospital and her insurance company just excluded live saving surgery

Bianca has been caught stealing from your company, and would do it again.

Tessa has an offer you might want to accept

Sleeping under her desk, Angel is hoping for mercy

Mercy doesn't care who you are when she leaps in to help

Skye has a heart of gold and an eviction notice

The company Christmas Party just got interrupted and there is no hero in a white tank top available. Or are you wearing one under your corporate attire?

Another in my series about Stars Stepping In. You could save or condemn any of these people. You could lead a corporate retreat, or you could take down the terrorists attacking your building. Whatever you do, you can afford to replace anything you break!