One Broker Shows What It Takes to Insure Hard-to-Place Risks

Jimmishea O’Lee likes to solve problems, so when a client needed help with its cryptocurrency business, she relished the challenge.
By: | April 15, 2026

The world of cryptocurrency is changing every single day, booming beyond the headlines as regulatory clarity emerges, institutions invest more in digital assets and scalability is integrated from the start.

But cryptocurrency as an asset can present a different face depending on the day. One day it may generate outsized returns; the next it may deliver the kind of volatility that unsettles even experienced investors.

Insuring crypto and other digital assets remains a challenge. Some point to the minimal historical data available as a detriment, while others highlight the fluctuating value of digital assets.

Still, it attracts billions from investors, and with that kind of popularity, businesses want a team to help get the coverage they need to operate in these markets. So, what does that look like in today’s insurance landscape?

“I was brought in to support several Pacific Northwest accounts facing nonrenewal in the broader market,” said Jimmishea O’Lee, a West Middle Market broking leader for Aon. “There was a perception that these risks would be difficult to place, but I saw an opportunity to take a fresh approach and deliver a solution.”

The accounts were heavily involved in Bitcoin. At the time its portfolio landed in O’Lee’s lap, the company was shifting from being a hosted service to one that mined Bitcoin completely internally. With a full switch of operations, underwriters balked.

“I started to geek out and read all the information I could online. I started to join podcasts, read Crypto for Dummies. I was interviewing my friends, the clients. And I got fully immersed in it,” O’Lee said.

This willingness to learn and advocate for the new-to-her client turned into a big win for O’Lee; and not just in terms of finding coverage, but also in reshaping how the insurance market is even approaching digital assets.

Starting Strong, Growing Stronger

As an international business and finance major looking to round out her resume, O’Lee joined the industry as an intern in risk management at Los Angeles International Airport (LAX).

However, it turned out to be trial by fire: Not long after she started, 9/11 completely disrupted the airline industry.

The introduction of a catastrophic risk manager at LAX — combined with her college’s recent introduction of a risk management and insurance major — convinced O’Lee she needed to shift her focus of study.

From there, O’Lee spent her time in roles across insurance, from being an underwriting assistant to global corporate property underwriter, and now, the broker she is today. O’Lee eventually carved out the place she wanted to be in her career.

“I do a little bit of everything, and I have a vast span of accounts. Crypto being one, but also lithium and others. I enjoy the stuff that’s hard to place,” she said.

A desire for challenge keeps O’Lee focused. When the crypto client landed on her desk, she rolled up her sleeves and dove in.

How to Insure Crypto

Of course, it wasn’t easy. At first glance, O’Lee also admitted she had her hesitations, but with a few helpful voices in her ear, she felt like she could really make a difference for the client.

“It just so happened I had a personal friend who was deeply into Bitcoin mining … the account executive practice leader at the time also said, ‘if I were you, I would lean into this,’ so I thought, well, there’s got to be something going on with this,” she said.

The main concern was the client’s data centers. Those in cryptocurrency understand that these facilities are massive in scale, housing high-performance computers dedicated to mining digital currency like Bitcoin. They run 24/7/365 using vast amounts of electricity and adequate fire protection isn’t guaranteed.

“[Crypto data centers] are not your traditional type of tech risk, even though it’s very similar to a tech risk,” O’Lee explained. “But they don’t have sprinklers, because [water] would destroy the miners. And so, right off the bat, when you talk about as much power and energy going through a location and add on that doesn’t have sprinklers, underwriters don’t even want to hear anymore.”

Combine that with a data center in a prime CAT zone, and it becomes extremely arduous to find an insurer willing to take on this high risk. But that kind of thinking didn’t stop O’Lee.

She buckled down, did her research, and provided a bespoke insurance solution to her client, enabling higher limits and competitive pricing. She adapted the property coverage to work for her clients, all while utilizing her connections in the U.S. and London markets.

“I spent a lot of time with these clients, understanding them as people and understanding their business and goals. Because of that, we became … a force [in this space],” she said. At one point, O’Lee was even working with the top crypto accounts in the world, further demonstrating just how impressive and exacting her efforts have been.

Today, her clients are covered, and the industry is approaching crypto with the influence of O’Lee’s finesse in mind. Her efforts have even earned her a 2026 Power Broker win in the At Large category.

A Bright Path Ahead

O’Lee is engaged in continuous learning, something that has opened the door to success in this business.

Learning is such a big part of the job, too, she noted, because “in order for the client to trust you, they want to make sure you understand their business, and so if you don’t take an active interest into what they’re doing, then how can they trust you to place their business? How do they know that you’re going to provide them with the best deal if you don’t even understand what they’re doing?” O’Lee said.

The best part of the job, she said, is getting to know the different people who make up this industry.

“There’s a lot of smart people … within the industry as a whole. I love the fact that no matter what technology is doing, we’re still a very people-oriented business. We all still know each other,” she said. “One of the most exciting things that I get to do is learn from others and understand their journey.”

As a people business, she said it’s important for young brokers to jump at opportunities when they arise. You’ll never know if it’s the one that will change your life.

“Don’t shy away from things that you don’t know or understand. I could have shied away from crypto, and I would have never had this opportunity,” she said.

“Usually, the things that you kind of smirk at, ‘oh, I don’t want to do that,’ probably are going to be the things that change your career. Just like my practice leader told me to lean in on something that I would probably normally not think to do, that’s what helped me get to where I’m at in my career today.” &

Autumn Demberger is a freelance writer and can be reached at [email protected].

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