Captive Madness

NCAA Forms a Captive— in Vermont!

Many Vermonters in the captive industry might have had an NCAA bracket that had UVM going all the way. Locals supporting locals is what we do here. Sadly, Arkansas stood in their way, and UVM came up a little short in the first round. They didn’t bust the nation’s brackets, but there were other perpetrators—I’m looking at you, Saint Peters Peacocks. The absence of the Catamounts from the Final Four makes it no less intriguing, but you might wonder, where’s the link with VCIA and captive insurance?

The Vermont Captive Insurance Industry is a Powerhouse Program

The answer lies in the fact that the NCAA, perhaps mindful of the hit that their marquee event took in 2020 and 2021, recently formed a captive, and not only that, but they have made its domicile in the Green Mountain State. Vermont’s most popular (and free) newspaper, Seven Days reports that the captive activated at the start of March and could “potentially save the association millions of dollars.” Taking on both D & O and event cancellation coverage, the entity has been funded with $175M, and will be consolidated into the financial statements of the NCAA.

The pandemic has raised the profile of Vermont’s captive insurance industry as more businesses have sought to self-insure, according to state officials.

ANNE WALLACE ALLEN, Seven Days

While the University of Vermont will not be crowned winners after this upcoming Monday’s championship, the State of Vermont surely won an impactful and lasting relationship with the National Collegiate Athletic Association. VCIA is happy to announce that their captive formation has joined our association on a free, first year trial basis.

My prediction for the Final Four winner (which is the sporting equivalent of a kiss of death)? Kansas Jayhawks. Who do you have?

A Busy and Productive Week with VCIA

Captive Roadshow and Hot Topic Webinar Major Successes on Back-to-Back Days

2022 brings a wealth of enthusiasm and optimism not only for VCIA but for the entire captive industry. The major cause of this excitement derives from the simple fact that we are all getting together again. Catching up. Building out networks. Collaborating on new ideas. The possibilities are endless when we’re all in the same room. (Which is why we’re so thrilled to bring back our conference this August!)

It’s no small feat then, that this week VCIA’s returned with its first in-person Original Captive Roadshow since November 2019!  In Indianapolis on Tuesday an audience of over sixty professionals listened intently and asked great questions as a panel of Vermont industry experts (Sandy Bigglestone, Dave Provost, Brittany Nevins) enjoyed a captive conversation facilitated by Hylant’s Anne Marie Towle. The Vermont team outlined the process and structures of captives in Vermont and why captives can thrive in the Green Mountain State.

2022 brings a wealth of enthusiasm and optimism not only for VCIA but for the entire captive industry. The major cause of this excitement derives from the simple fact that we are all getting together again.

Following that, two captive owners Valynda Laird and Will Lehman explained their business case and development of their own entities that have done so well due to captive formation.  The feedback was very positive and we are already deep in planning for the next two. The Big Apple just might be seeing our Roadshow before the year lets out.

A great turnout it Indy

Not forgetting our Hot Topic Webinar series, the very next day our March webinar had a similar number of attendees for a great session on Strategic Planning for Captive Optimization and Future Success. Many thanks to the erudite panelists, and the State of Vermont’s own Christine Brown who moderated the talk.

These events and others, both online and in-person, have served us well as we identify in-demand topics and exceptional presenters for our August 2022 conference. We are about 6 weeks away from registration, but you can get a ‘sneak peak’ of the entire schedule and sign up for more info at VCIA.com.

Cheers to you, captive learning, and captive collaboration. Happy spring!

Captive Insurance and Rugby: Staff Spotlight on President Kevin Mead

Captive Insurance is a bit like rugby. Let me tell you why.

Just three weeks in, and I have quickly learned some truths about the captive insurance industry. Truth number one: how badly it is understood by those outside. Even those that have a knowledge of risk or insurance sometimes seem to shake their heads and mutter darkly when the subject is raised. Truth number two: that external lack of knowledge (or potentially confusion) means that the industry itself is tight knit, cooperative, and friendly.

Over 25 years ago, authors Adam Brandenburger and Barry Nalebuff co-authored a book called Co-Opetition in which they used game theory to suggest that businesses should cooperate to “grow the size of the pie,” and then compete for a larger slice of that enlarged pie.  Seeing the way in which board members and other VCIA volunteers are working together for the benefit of the association and for the industry is almost a case study in what the authors refer to.

“Real success comes from actively shaping the game you play—from making the game you want, not taking the game you find.”

― Barry J. Nalebuff, Co-Opetition

A second thing that has struck me is the number of rugby people there are in the captive industry. And there are similarities! To the uninitiated, rugby looks dangerous, risky, and somewhat unmanaged. To those that know the game, it is subtle, nuanced, athletic, and referred to as “the game they play in heaven.” On the field, rugby players are intensely competitive, but once the final whistle blows the bruises and battles are forgotten and a spirit of camaraderie and mutual support comes to the fore.

So, rugby as a metaphor for captive insurance? Perhaps that is too much of a reach! But my predecessor, Rich Smith, commented to me multiple times that the essence of the VCIA was built around mutual respect, understanding, and a sense of all being in the same league—if not all on the same team.

For me, rugby season is about to start up. This Saturday, the 19th, I will be refereeing at a tournament put on by the University of Vermont women in Burlington. Feel free to check this out or any rugby game in your location and see if my comments on the similarities hold any water! 

Announcing the 2nd Keynote Speaker for our August Conference

Enjoy political thrillers? Then you will need to hear from Michael Weidokal, founder of International Strategic Analysis, at the VCIA Conference!

These days, it’s an understatement to say global geopolitical stability is being challenged—look no further than Ukraine. I often find it difficult keeping up with intricate and sometime disparate elements that bear consequences not just worldwide, but at home. Which is why I’m proud to announce that VCIA has secured a second keynote speaker for our conference in August—Michael Weidokal, founder of International Strategic Analysis, and a shrewd economic and political forecaster. His lecture will be timelier and more relevant than ever.

Founder of International Strategic Analysis and VCIA Conference Keynote Speaker Michael Weidokal

I’ve used Michael as a speaker three times in my career, and I kept coming back to him because he consistently received top marks from audience feedback. I think what makes him so effective is his facility at explaining and distilling global structural challenges, their historical backgrounds, and their potential economic fallout. To put it in a nutshell: Michael combines economic theory and geopolitical situations, rendering them into a real-life political thriller, all the while predicting, with sufficient evidence, how they impact you and your business. You will be both intrigued and informed—hallmarks of a successful and worthwhile keynote address.

Michael combines economic theory and geopolitical situations, rendering them into a real-life political thriller… while predicting… how they impact you and your business.

His deeply researched and vetted lecture, “Global Economic and Risk Outlook,” draws interest from many different industries and conference circuits. According to Michael’s website, the general theme of his speech investigates “factors that are driving or hindering economic growth in the United States and in all of the world’s major economies.” Utilizing the latest data and current events, Michael will provide VCIA Conference attendees “an in-depth analysis of all of the important issues and trends that will impact their activities in domestic and international markets, both in the year ahead and over the long-term.”  

We can’t wait for you to meet Michael Weidokal, and he’s excited too. Learning that our conference is the premier event of the captive industry, he added to me in an email, “I very much look forward to speaking at this year’s VCIA conference!”

Don’t forget he’s the second of two outstanding keynote speakers we now have. The inimitable Admiral Michelle Howard, the first woman in the U.S. Navy’s 236-year history to be promoted to four-star admiral who achieved the second highest-ranking in the service, will share her experiences and insights on national security, leadership, risk, and much more.

VCIA’s 37th Annual Conference Distinguished Keynote, Admiral Michelle Howard

If these two won’t get you to come to our first, in-person conference in three years, what will? I guarantee you amazing and topical presentations, plus wonderful networking and business development opportunities.  I also guarantee you the pleasures of summer in Burlington, Vermont—stunning views of Lake Champlain, the festive atmosphere of Church Street, and quick access away to the lush Green Mountains and the great outdoors. A perfect destination for you and your family.

Registration opens May 16th.

Water, Sun, Mountains, and Captive Insurance…

See you at CICA

Today I will be hopping on a plane destined for the southwest; Tucson, Arizona, to be exact – where CICA’s 2022 International Conference will be taking place. In span of just a few weeks, I will have attended the World Captive Forum in Miami and now CICA. It’s hardly been a gradual easing into the position of President of VCIA; rather the opposite: I’ve jumped in and enjoyed every moment of it.

With our affable Director of Membership Janice Valgoi, I spent my days in Miami meeting many wonderful folks who make the captive industry what it is. Perhaps more importantly, I was able to carefully listen to their concerns and hopes for the state of captive insurance in 2022. I also participated in Captive 101, something VCIA will feature in its Conference this August. The course in Miami was engaging and informative. A “brains trust’’ (including Vermont’s own Dave Provost) did their utmost to make captives intelligible to those of us who are new arrivals. Any lack of understanding was my fault, not theirs!

Learning from the greats at the World Captive Forum: Dave Provost, and VCIA Board Chair Andrew Baillie

Now, having World Captive Forum in the rear view, I look forward to CICA with even more enthusiasm. In Miami, it was tremendously energizing and delightful to be with people in person again, and I was warmly welcomed by so many important makers and doers within the captive industry, some of whom have decades of institutional knowledge and experience! Many thanks to the State of Vermont’s Dave Provost and his team for hosting us at their World Captive booth.

it was tremendously energizing and delightful to be with people in person again, and I was warmly welcomed by so many important makers and doers within the captive industry

I’m Irish, and so I will cheerfully enjoy the Craft Brewery Tour during the CICA event. I hope we can raise a glass together and get to know each other. I look forward to making strong professional connections and learning more about the intricacies of captive insurance in the process. So, please, do reach out at the conference, and see you at CICA!

Finally, all connected with the VCIA are looking forward to welcoming you back to Burlington in August after a two-year virtual hiatus.  Bigger, better and stronger – please come and celebrate VCIA’s 37th Annual Conference! Registration opens May 16th.


Kevin Mead became the President of VCIA in February 2022. Send him a greetings or open up a conversation with him at kmead@vcia.com

Rich Smith’s Last Blog Post as VCIA President

Bon Voyage, Rich!

“Goodbye Always Makes My Throat Hurt” – Charlie Brown

This is my last blog as President of VCIA. I can’t tell you all what a delight and how meaningful the last 12 years has been for me. I have worked with such wonderful people and made truly great friends in the captive industry.

I remember in my first year as President the marvelous Tom Jones came up to me at an event. With his wry smile and baritone voice, he said to me, “Rich, the only thing you need to be aware of is that there is a ‘no a-hole’ rule in the captive industry.” I immediately laughed out loud but recognized over the years how true that is (OK, it’s not quite universal, but close enough!).

I have worked with such wonderful people and made truly great friends in the captive industry

Outgoing vcia President Rich Smith

With a deep sense of relief, I confidently know I am leaving VCIA in excellent hands. Kevin Mead brings a wealth of association experience along with great common sense and a wonderful sense of humor – all tools that will make VCIA continue to shine.

Rich and Vermont Governor Phil Scott

I want to thank all of you that have provided me with your wisdom, guidance, and friendship. It has meant the world to me. That is especially true of the 36 board members, past and present, that have given their time and energy to this great association – thank you so much. You are the superstars of the captive universe!

To have worked with the outstanding regulators at Vermont’s Department of Financial Regulation these past 12 years has been an honor and a pleasure. The team lead by Dave Provost, Sandy Bigglestone, Dan Petterson, and Christine Brown is the reason Vermont is THE top captive domicile in the world. This may sound like bluster, but I am quoting what my colleagues representing other domiciles told me on a regular basis. Not only that, but Vermont DFR is certainly the nicest and fun-loving group of regulators you have ever met.

Rich and colleagues at the US Capitol Building

Most of all, a warm thank you to all the wonderful VCIA staff over my tenure that have made the Association the stellar organization it is (and made me look good to boot): Diane Leach, Peggy Companion, Janice Valgoi, Megan Precourt, Dave Rapuano, Elizabeth Halpern, Julie Brown, Barbara Casanova, and newcomer Francis McGill – you all rock!

I look forward to watching the Association thrive over the next many years. Please feel free to reach out to me to say “hi’ once in a while and I will do the same. My new email address is mykasmithvt@gmail.com.

Thank you all and I look forward to hearing from you.

Roger Phelps

Roger Phelps passed away a few days ago. It is slightly overused, I suppose, but Roger was one of the founding fathers of Vermont’s captive insurance industry – including VCIA. We have lost a number of early captive innovators in the past few years.

Roger was a very creative person – you had to be to get both the industry and VCIA off the ground from the beginning. He even created VCIA’s first logo! Roger got ALCOA’s captive (Three Rivers Insurance Company) started in 1983 – license #8. Three Rivers is one of the few parent companies with a captive employee intentionally located in Vermont.

Our hearts go out to his family and friends, and the many people he touched in the captive community. He influenced many.

Thank you and I look forward to hearing from you.

Rich Smith
VCIA President

Cowbell Cyber

More Cowbell! The Rise of Cowbell Cyber, now with an Agency Captive Domiciled in Vermont

We all know that cyber has grown to be one of the top insurance issues facing organizations for the past five or so years. Captives have led the way in many cases providing personalized cyber risk policies for their owners that have been difficult or expensive to find in the traditional insurance market.

Now there is another arrow in the quiver in the captive cyber market. Cowbell Cyber, a cyber-insurance provider who has developed the first continuous underwriting platform, recently formed a Vermont-domiciled agency captive insurance company. An agency captive is a reinsurance company controlled by an insurance agency or brokerage. Through a reinsurance agreement with a traditional insurer, the agency captive receives a share of the premiums written and is obligated to pay its share of claims. Vermont legalized agency captive formations in 2017.

Cowbell Cyber, Closing the Cyber Insurability Gap

With an agency captive based in Vermont, Cowbell Cyber has the capacity to meet the exponential demands for cyber insurance. The company will surely stand out from its competition, based on cutting-edge A.I. software which comprehends actuarial models and inside-out data sources. You cannot get better than real time updates and customized assessments, which is what Cowbell Cyber provides. As it says on their About Us page, what makes them different is that “Cowbell factors benchmark enterprise risk exposure against a risk pool of millions of businesses.”

You cannot get better than real time updates and customized assessments, which is what Cowbell Cyber provides.

The InsurTech firm uses artificial intelligence to assist in risk selection and pricing as it underwrites cyber-insurance coverage for small-to-medium enterprises. Last September, it launched the industry’s first cyber risk marketplace, Cowbell Rx, giving the company more flexibility in addressing the expanding demand from its growing distribution network of 2,000 agencies and 12,000 producers nationwide.

Why the name Cowbell? No, it’s not in homage of the iconic SNL skit, but the company traces its name back to the livestock bell and its timeless practice of ringing out when the animal herd is in distress. The cowbell is a warning signal that alerts the farmer to any abrupt change, and Cowbell Cyber alerts enterprise risk managers to the fluctuating hazards and remediations to mitigate potential losses for its clients.

Providing just another way to meet the world’s risk mitigation needs, Vermont remains the domicile of choice for captive innovation.

Thank you and I look forward to hearing from you.

Welcome, Kevin!

Earlier this month you met our new Communications Director, Francis McGill. Now I would like to take the opportunity to introduce my replacement as President of VCIA, Kevin Mead!

Kevin Mead, new VCIA President

As you may have seen in our announcement earlier this week, Kevin brings a boatload of skills in association management and financial wherewithal based on his experience running a number of associations. (Click here for the official announcement.)

Kevin is a unique fellow: he lives in Vermont’s Northeast Kingdom (the most rural part of our rural state), has a British accent, and loves rugby. But more than that, I got to know Kevin over the past few months, and he is truly a nice, decent human being – someone who will fit right into the captive insurance family.

Holding two master’s degrees related to association management and finance, Kevin is the perfect candidate to lead VCIA, build out the captive industry’s flagship conference, increase VCIA membership and membership value, while evolving the organization amid the current pandemic and economic challenges. Above all, he is a true “people’s person.” Our staff is thrilled to have him on board and I know he will make many meaningful and productive relationships with our members.

Although his official start date is February 22nd, Kevin has been hard at work absorbing all things captive insurance and VCIA over the past few weeks. He will be traveling to Miami for the World Captive Forum with VCIA’s own Janice Valgoi and the incredible team from the State of Vermont, so, if you are going to be there, please take the time to reach out and introduce yourself.

Thank you and I look forward to hearing from you.

The Results Are In

You all saw it coming. The number of captives licensed in Vermont last year eclipsed 2020 – already a banner year. Sure, almost every captive domicile had a good year, but even with over 40 states establishing captive laws, Vermont stands head and shoulders above.

Here are the hard numbers: Forty-five new captive insurance companies were licensed this past year in Vermont, making 2021 Vermont’s 4th highest year of growth in its 40-year history. Vermont is now home to 620 licensed captives, consisting of 589 active and 31 dormant captives. Vermont’s 52 sponsored cell captives currently host nearly 500 cells and separate accounts, in addition to the licensed captive companies.

The new captives were licensed in 17 different industries, the main industries being healthcare, real estate, manufacturing, insurance, and transportation. At least 5 of Vermont’s new captives in 2021 were formed by companies with international roots, including Japan, Germany, Russia, the United Kingdom, and Australia. Vermont has been experiencing growth in the number of new cells within sponsored captives, at a similar pace as new company licenses, with nine of the 45 new companies formed this year being sponsored cell companies.

Vermont has licensed a total of 1,242 captive insurance companies since 1981 and remains, by far, the largest U.S. domicile for captive insurance and third largest in the world. With an active pipeline of prospective new captive insurance companies already underway for 2022, the state expects continued growth in the coming year.

Thank you and I look forward to hearing from you.

Rich Smith
VCIA President