The people behind hundreds of captives.
Two founders with law degrees, one with a master's in accounting, both business owners, both still teaching this in the room. And the operator who keeps every one of those captives running on time.
A chance seat in the back row.
July 2012. A breakout session on captive insurance at an estate‑planning symposium in Denver. Two attorneys, both in estate planning, sat down next to each other in the last row.
One practice leaned toward tax and accounting. The other toward financial planning and investments. Estate planning was the shared foundation; the lean was the difference, and it turned out to be the whole idea. Captives sit exactly where those two disciplines meet, and almost nobody serving the middle market spoke both languages.
By March of the next year, Fortress Risk Management was branded and launched. The job has not changed since: make a heavy financial tool feel simple for the owners of small and midsize businesses, and do it properly, every time.
The three of them, teaching captives to a room of advisors. Still the way most clients first meet Fortress.
The principals of the firm.
Todd Bailey, J.D., MAcc
Two accounting degrees and a law degree, two decades of practice, and then a single focus: captive insurance for successful businesses. A frequent speaker to owners and professionals on managing risk, controlling costs, and improving cash flow. Married, five children, a growing number of grandchildren. Travel, fishing, and golf when the season allows.
Paul Mason, J.D.
Founded several companies after his law degree and a decade in the investment and financial‑planning world. An estate‑planning and risk‑management attorney who enjoys teaming up with other professionals to solve a client's problem together. Married, four children. Has finished more Half Ironmans than he will admit to and a full one in 2010.
Josh Lunn
The first half of his career in enterprise software, building customer solutions and running technical teams. Then his own property and casualty agency, from 2011. Joined Fortress in 2017 to build the processes and procedures that let the firm grow without losing the thing clients notice first: things happen when they are supposed to.
Independent by design.
Fortress consults. The captive is run by professionals whose independence is what makes the structure sound.
- Credentialed actuaries identify the risks, set every premium from industry data, and update the study each year.
- A licensed insurance manager forms and licenses the company, keeps the reserves, administers claims through a committee, files the return and the elections, and answers to the regulator.
- A law firm handles the corporate work, year after year.
- Your own advisors, your CPA and your financial advisor, are in the process from the first call and manage the reserves under written guidelines.
- 1953
Fred Reiss founds Steel Insurance Company of America for Youngstown Sheet & Tube in Ohio, borrowing the word “captive” from the company’s captive mines.
- 1986
Congress adds a provision to the tax code for small insurers, opening captives to the middle market.
- 2010
The founder's first captive client, a benefits consulting and billing company in the Northwest.
- 2012
The back row in Denver.
- 2013
Fortress Risk Management is launched.
- 2015
Captive insurance for dental warranties, a new tool for practices to fund the warranties they give and keep the patients they have.
- 2017
Fortress reaches 125 captive clients, one of the largest captive consulting practices in the country, and hires its chief operating officer.
- 2018
Fortress moves into its own building in Colorado Springs.
Talk to a principal, not a sales team.
One hour. Your business, your risks, a straight answer.