There are two ways for Insurance Companies, Banks, Private Equity firms, MGAs, and insurtechs to approach complex risk in 2025:

1. Rely on generic solutions, potentially overlooking critical gaps.
2. Partner with specialized expertise that delivers clarity and tailored protection.

Many sit in the first category, often underserved by mega-brokers.

Your institution has unique strengths and ambitions. 

But is your risk management truly aligned? 

Or are you unknowingly exposed due to:

–  Coverage gaps hidden in the fine print?

–  Lack of access to sophisticated global markets?

–  Decisions made without credible peer data or advanced analytics?

–  Impersonal service that doesn’t grasp your specific operational realities?

The bigger problem?

You're leaving strategic advantage on the table and potentially facing significant financial or reputational risk down the line.

The solution?

Transform your risk management from a necessary cost center into a strategic asset through a bespoke, expert-driven partnership.

That’s my focus at LION Specialty.

My approach combines:

– Penetrating technical analysis honed by deep experience (including handling complex Fortune 100 accounts) to uncover what others miss.

– Global market access (London, Bermuda) and perspective, crafting solutions beyond standard domestic offerings.

– Process mastery & advanced analytics delivering clarity and confidence, not complexity.

– Authentic human connection, building partnerships that thrive.

(informed partly by my wellness background as a Pilates instructor… sustainable success requires balance)

–  Are you serious about closing critical coverage gaps?

–  Are you ready for risk management bespoke to your institution's needs?

–  Is it time for a partner who brings both sophisticated expertise and a refreshingly collaborative approach?

Let's connect and explore how we can elevate your strategy together.

Natasha Kiemnec

Today, I turn 38. 

I tell you this not because I want wishes of happy birthday but because each year on my birthday I go through successes,  “experiences”, and reflections of my prior year, so I thought I’d share a few here.

1. My parents being a plane ride away is too far. The older they get the more I realize how precious time is with them. Try to always be as kind and gentle with them as you can. 

2. Often in life we are blinded by our own bias. The thing you want most - fitness, that relationship, that money whatever it is, with some simple observation really isn’t that hard to achieve. Don’t over complicate. 

3. Relationships (with most people) are a balance of understanding. General frustration comes from a lack of feeling seen or understood. Patience, grace and understanding go along way. 

4. Be kind - I often watch people be unkind for no reason. 

5. Tale as old as time but work hard. A lot of struggle can be removed from simply putting your head down, keeping your mouth shut, and getting the work done. 

6. My mom used to always tell me to just start. Whenever I was stressed out and overwhelmed - just start. It’s still applicable now. 

7. To those who help - a partner, a coworker, an employee, a family member - you can’t be appreciative and grateful enough. There truly isn’t an end to being thankful. 

8. Have a passion that isn’t work. 

9. Get outside - take breaks. A 20 minute walk always helps. 

10. Always be learning. 

What reflections have you had on birthdays or during moments of pause?

Natasha I.  Kiemnec, ARM

Managing Partner & Co-founder of LION Specialty | Global Financial Institutions & Private Equity Broker | Classical Certified Pilates Instructor

No alternative text description for this image

If your CEO lies on an insurance application, does your D&O policy still protect you?

If you don't know the answer, you are personally exposed.

Insurance applications require a signature. Usually, the CEO or CFO signs it on behalf of the entire executive team.

But what if they hide a material fact?
What if they know about a pending SEC investigation and don't disclose it?

Under a standard D&O policy, the carrier can rescind (cancel) the entire contract if the application contains a material misrepresentation.

The carrier says: "The CEO lied. The policy is void."

You, the innocent board member or VP, are suddenly facing a lawsuit with zero insurance protection. Your personal assets are on the line because of someone else's fraud.

We manuscript "Full Severability" language into every D&O program.

This clause legally separates every insured person.
It dictates that the knowledge or fraud of one executive cannot be imputed (assigned) to any other executive.

If the CEO lies, the CEO loses their coverage.
But your coverage remains fully intact.

You cannot control the actions of every person in the C-Suite.
You can control the contract that protects you from them.

Check your D&O policy today. Look for the "Severability of the Application" clause.

If it says "Imputed to the CEO and CFO," you have a massive gap.

DM me "SEVERABILITY" and I'll review your language.

The most expensive gap in your insurance program isn't an exclusion.

It is a missing file.

Carriers deny more claims for "lack of substantiation" than for actual coverage disputes.
If you can't prove the loss, you don't get paid.

Most companies scramble to build the file after the crisis hits.
That is too late.
You are trying to find invoices and emails while your building is burning or your network is down.

The LION Process:
We build the documentation protocol before the policy binds.

1. The "Day One" Folder
We establish exactly what the adjuster will ask for.
Payroll records. Vendor contracts. Asset lists.
We keep them staged and ready.

2. The Communication Log
During a claim, every phone call needs a follow-up email.
"As we discussed..."
If it isn't written down, it didn't happen.

3. The Timeline
We map the event minute-by-minute.
"Breach detected at 4:02 PM. Counsel notified at 4:15 PM."
Precision kills ambiguity.

An adjuster's job is to ask questions.
Our job is to have the answers ready before they ask.

Is your claim file ready for an audit today?

DM me "DOCUMENT" and I'll send you our claim substantiation checklist.

The insurance industry was built for buildings that burn.

The economy runs on digital infrastructure that just stops working.

There is a trillion-dollar gap in the global insurance market.
It is called Non-Physical Damage Business Interruption (NDBI).

Most property policies require "direct physical loss or damage" to trigger coverage.
A fire. A flood. A hurricane.

But what happens when a cloud provider goes down?

What happens when a payment gateway fails?
What happens when a DNS attack takes your platform offline?

There is no "physical damage."
The servers are fine. The building is standing.
But your revenue has stopped.

Traditional policies say: "No physical damage? No claim."

You are left absorbing millions in lost revenue while paying premiums for a risk that doesn't match your reality.

We don't rely on "Property" forms for digital risks.
We build Parametric triggers and System Failure coverage that responds to the outage, not the damage.

If the network is down, the policy pays.
It doesn't matter if the server room burned down or if a software update just failed.

The loss is the same. The coverage should be too.

Does your Business Interruption policy require "physical damage" to pay?

If you are a digital business, that clause is a trap.
DM me "NDBI" and I'll review your trigger language.

Your insurance policy doesn't protect you the day it binds.

It protects you the day your team knows how to use it.

Most brokers view the "Bind Date" as the finish line.

The invoice is sent. The commission is earned. The file is closed until next year.

That is exactly when the real risk begins.

A $10M D&O policy is useless if your General Counsel doesn't know the exact trigger for notifying a claim.

A Cyber policy is worthless if your Incident Response team calls the wrong vendor during a ransomware attack.

While we bind, we make sure that the team knows how the policy works. 

We don't hand you a 200-page PDF and say "good luck."

We sit down with your CFO, your GC, and your Risk Manager.

1. The Trigger Map
We map out exactly what constitutes a "Claim" under each policy. (Is a subpoena a claim? Is a regulatory inquiry a claim?)

2. The Call Tree
We build a one-page protocol. If X happens, call Y. We establish the pre-approved vendors and legal counsel so you aren't negotiating rates while your servers are locked.

3. The Exclusions Briefing
We highlight exactly what is not covered, so your team can build operational controls around those specific risks.

Insurance is not a document you file away.
It is an asset you have to know how to deploy.

When was the last time your broker trained your team on how to actually use your coverage?

DM me "PROTOCOL" and I'll send you our activation checklist.

A green light in the server room does not mean your business is recovered.

But your insurance carrier might think it does.

We are seeing a dangerous trend in Cyber claims.
Carriers are cutting off Business Interruption payments the moment the "computer network" is technically restored.

They argue: "Your servers are up. The claim is over."

Your servers are up, but your business is still bleeding.
You are reconciling lost data. You are re-indexing files. You are working through a massive backlog of manual entries. You are waiting for vendors to re-certify your connections.

The "outage" is over, but the financial loss is just beginning.

We audit the definition of "Period of Restoration."

If your policy says the period ends when the "Network is Restored"... you are exposed to the post-breach drag.

We clarify the language to reference "Restoration of Business Operations to the condition that existed immediately before the breach”

This ensures the policy pays until your revenue and throughput return to pre-incident levels—not just when the IT ticket is closed.

Do not let a forensic accountant tell you when your business is back to normal.
Let the contract dictate it.

Check your Cyber policy today. Search for "Period of Restoration."

Does it say "Network" or "Operations"?

The difference is your entire Q3 profit margin.
DM me "RESTORE" and I'll review the definition.

You wouldn't hire a CFO based on who has the cheapest laptop.

So why do you hire a broker based on who has the cheapest quote?

Most companies run their insurance RFP like a commodity purchase.

"Here is our data. Go get quotes. We will pick the lowest premium."

This is a trap.
You are incentivizing your broker to strip coverage to hit a price target.

The LION Process:
When you hire a broker, you are hiring a defense team.

You don't ask a heart surgeon for a discount. You ask for their success rate.

The 3 Questions You Should Ask:

1. "Who is on my team?"
Not the sales guy. The technical broker. The claims advocate. I want to see the resumes of the people protecting my balance sheet.

2. "Show me a manuscript."
Don't tell me you can improve coverage. Send me a redacted policy you wrote. Let me see the actual words you changed.

3. "Walk me through a denial."
Tell me about a claim you fought and won. If you haven't had to fight, you haven't been doing this long enough.

Stop buying insurance.
Start hiring expertise.

Are you running an RFP this year?

DM me "RFP" and I'll send you the Broker Evaluation Scorecard we wish every client used.

Bankruptcy doesn't just freeze your assets.
It can freeze your insurance defense.


A portfolio company filed Chapter 11.

The directors were sued immediately for "breach of fiduciary duty."

They called the insurer to pay for their defense.

The Bankruptcy Trustee stepped in.

"That policy is an asset of the estate. You cannot deplete it to pay for legal fees."

The directors were left paying $800/hour lawyers out of their own pockets while a $5M policy sat frozen in court.

We structure "Priority of Payments" clauses into every D&O program.

This language dictates that in the event of bankruptcy, the insurer must pay the individual directors first.

The estate only gets what is left over.

We also add "Side A" DIC (Difference in Conditions) coverage that sits completely separate from the corporate balance sheet.

You don't need insurance when things are going well.

You need it when the walls are closing in.

If your policy isn't bankruptcy-proof, it’s not finished.

Does your policy have a "Priority of Payments" clause?

DM me "PRIORITY" and I'll show you where to look.

The thing about being a woman 


Is that for every moment someone called you

Emotional 
Indecisive 
Quiet 
Irrational 
Bitchy 

May have actually been moments where you were reacting to something not quite right. 

As times have shifted in the past ~10 years, since reading Lean In by Sheryl Sandberg, and hearing Codie A. Sanchez  talk about your haters actually being your fans, I’ve realized it’s less about us reacting in any of those emotions, it’s being told that we’re wrong to have them. 

When actually those emotions might actually be our super powers. 

When used to accurately judge a situation, treat people with kindness, grace, more humanness - that isn’t emotional - it’s power. 

So to all the women out there
leaning in
guiding with grace
remember those names are actually your power. 

Happy International Women’s Day 💕

PS. Two of my absolute favorite women (my aunt and mom)

Five events since 2017. Combined losses from billions to trillions. Physical damage across all five: zero.

NotPetya. 
The 737 MAX grounding. 
COVID-19 shutdowns. 
The Ever Given. 
CrowdStrike.

We went line by line through the coverage implications this week. The exposure class is Non-Damage Business Interruption, and for financial institutions running digital-first operations on legacy programs, the gap between what can shut you down and what your policy actually covers is measured in trillions.

But the article that stopped me was a Law360 piece on cyber policy restoration periods.
The distinction between “operations-focused” and “network-focused” language in your period of restoration definition is outcome-determinative. 

One version covers you through the full resumption of normal business activity. The other stops the clock the moment someone reboots a server — even partially.

That’s the kind of clause that determines whether your next cyber claim pays for twelve weeks of operational drag or cuts off at week two. 

Silence in insurance is dangerous. Especially in the definitions section.

We covered all of it in this week’s Friday Five, plus a forward look at parametric capacity that could compress payout timelines from months to days.

P.S. link in comments. 

P.S.S. Part 1 of our Wednesday Intelligence miniseries on deepfakes is live. What happens when bad guys deepfake your CEO — and six questions for your next renewal. Link in comments.

Your employee didn't get hacked.
They got tricked.

And your insurance policy treats those two things very differently.

A controller gets an email from the "CEO."
"Please wire $500,000 to this vendor immediately for the acquisition."
The email looks real. The tone is urgent.
The controller wires the money.

You file it under your Crime policy.
The carrier points to the "Voluntary Parting" exclusion.

"Your employee voluntarily sent the money. This wasn't theft. It was a mistake."

Or they point to the "Social Engineering" sub-limit.

"We cover this, but only up to $100,000."
You just lost $400,000.

We don't accept $100k sub-limits for the biggest risk you face.
We manuscript the definition of "Computer Fraud" to include "Social Engineering" and "Impersonation Fraud."

We stack the Crime policy limits with the Cyber policy limits to ensure you have full tower protection, not just a sliver.

If your policy penalizes you for being human, it’s the wrong policy.

Check your Crime policy today. Look for the 

"Social Engineering" endorsement.
Is it $5M or $100k?

DM me "FRAUD" and I'll review your limits.

There is a question plaintiff attorneys will ask after every data breach in 2027.
Most boards haven't even heard the premise yet.

"Did you use AI-powered security scanning tools to check your code?"

If the answer is "No," you might be negligent.

Last week, Anthropic released an AI tool that scanned production codebases and found 500+ vulnerabilities that human experts missed for 20 years.

These weren't minor glitches. They were exploitable flaws hiding in plain sight.

Traditional scanners check for "locked doors" (passwords, encryption).
AI checks for "structural weakness" (broken business logic).

We saw this with MFA.

Three years ago, Multi-Factor Authentication was "nice to have."

Today, if you don't have it, you are uninsurable.

AI code scanning is next.

When a defensive tool becomes widely available and highly effective, failing to use it stops being a "resource decision."

It becomes a "breach of fiduciary duty."

The window between discovery and exploitation is compressing from weeks to hours.
Your defense needs to move at the same speed.

Is your board asking about AI security, or are they waiting for the lawsuit?

We put together a one-page AI Security Standard-of-Care Checklist — 10 questions your board should be asking before your next renewal. 

The carrier application changes already in motion. The specific coverage intersections across cyber, tech E&O, and D&O. 

What the standard of care looks like now, not 12 months from now.

Comment CHECKLIST and I'll send it over.

Two federal courts ruled on AI and privilege the same week.

One said consumer AI destroys confidentiality. The other said AI is a tool, not a person, and work product survives.

Both issued February 10, 2026.

Here's why this matters for carriers and the institutions we serve:

In Heppner (SDNY), a defendant used the free version of Claude to draft 31 defense strategy documents without his lawyer's involvement. Judge Rakoff held that Anthropic's privacy policy, which permits data training and disclosure to regulators, destroyed any expectation of confidentiality. No privilege. No work product protection.

In Warner (E.D. Michigan), a pro se plaintiff used ChatGPT to prepare litigation materials. The court denied the defendant's request to compel those materials, holding that compelling production "would nullify work-product protection in nearly every modern drafting environment."

Same technology. Opposite conclusions. The difference came down to two things: attorney direction and platform terms.

We also dug into a 108-page bad faith report from Freeman Mathis & Gary covering 26 states. We stripped the auto cases and pulled the P&C patterns:

Safe harbors are crystallizing in Indiana and Florida 

Communication failures carry compounding penalties in Pennsylvania 

Coverage drafting precision is being rewarded across multiple jurisdictions

And a federal court allowed bad faith claims to proceed against an insurer using undisclosed AI in claims handling. If your adjusters are confirming algorithmic output rather than conducting independent investigations, the file tells that story.

Silence in insurance is dangerous. 

That applies to AI governance too.

This week's Friday Five Boardroom Brief breaks down all three developments with Monday morning action items.

Comment BRIEF if you're not on our list.

P.S. The Heppner opinion is 12 pages. The Warner order is 14. Both are worth the read if you're advising clients on AI use policies.

The Mega-Broker staffing gap is structural, not accidental.


If your premium falls below their threshold, the specialist team doesn't show up.

We recently took over a D&O account for a mid-market financial institution.

They had been operating under an extended reporting period. The directors didn't even have current limits.

When a claim hit, every weakness in their broker's process was exposed: no communication runway, and no renewal strategy worth the name.

We didn't do anything complicated.
We just ran the process that should be standard.

We put a senior specialist team on the account.
We started the renewal 150 days early.

We got the client directly in front of the carriers.

We ran a disciplined marketing process with enough time to maneuver.

Reduced premium. Refreshed limits. Current coverage for the board of directors.

The mega-broker they fired had the capability to do everything we did.

They have specialist teams. They have carrier relationships.

They just didn't deploy any of it on this account because the economics didn't justify it.

Below a certain revenue threshold, you get the regional office. You get the generalist. You get the 60-day compressed timeline.

When everything runs smoothly, you might never notice the difference.

But claims don't ask if the A-team is assigned to your account.

Regulatory inquiries don't care if your renewal started 150 days out or 60.

How do we know?
We lived it for two decades. We worked inside those machines.

The moment complexity arrives, the gap between "process" and "improvisation" becomes very expensive.

Who is actually doing the work on your account?
Not the name on the proposal. The team doing the daily work.

If the answer gives you pause, that's the conversation worth having before the next claim forces it.

If you’re interested in the story, check out our Wednesday intelligence which went out today. Comment “WEDNESDAY” and I’ll add you to our distribution.

Check our the podcast version of our Wednesday intelligence!

There are 48 approved Lloyd's war exclusion wordings for cyber.

Forty-eight.

And attribution of a state-sponsored cyber attack takes years. Sometimes longer than the policy period.

I spent the week going line by line through the Trellix threat intelligence assessment that dropped March 5. 

Ten active Iranian cyber groups. 

MuddyWater targeting a financial institution in Egypt. 

CyberAv3ngers building custom malware for operational technology in the US. Rust-based payloads. AI-assisted development. 

The technical evolution is real.

But what matters to our clients isn't the malware taxonomy. It's the coverage question.

If a regional bank or community hospital on your book gets hit with ransomware traced to an IRGC-linked group, you're looking at a war exclusion dispute before the forensic report is final. 

The wording matters. 

The classification matters. 

The difference between "hostile cyber activity" and "cyber war" in your manuscript language could determine whether a claim pays or fights.

That's before you connect it to the reinsurance repricing. Seven of twelve P&I clubs cancelled war-risk cover. 

Maritime premiums surged over 1,000%. 

And Morningstar DBRS warned they'll raise attachment points on treaties that have nothing to do with the Gulf.

Your producers should be walking into client meetings this week with three questions:

What does your cyber war exclusion actually say? 

When was the last time anyone reviewed it against the LMA classifications? 

Does your incident response plan contemplate a state-sponsored attack during active military conflict?

We break down all three channels in this week's Friday Five Boardroom Briefing. 

Comment NEWSLETTER for the link.

The worst time to discover your insurance carrier's claims philosophy is during a claim.


A $10M limit from Carrier A looks exactly the same as a $10M limit from Carrier B on a spreadsheet.

The premium might even be 5% cheaper.

But that spreadsheet hides the reality of the transaction.

It doesn't show you their litigation history. It doesn't show you their default response to a complex loss.

We vet the claims department before we look at the premium.

1. The Philosophy Audit
We track how carriers behave under pressure. We know which markets actively look for ways to pay, and which ones immediately draft "Reservation of Rights" letters to protect themselves.

2. The Authority Check
We identify who actually holds the pen. If your underwriter has to ask a committee in another time zone for permission to settle, your recovery will stall. We place business with direct decision-makers.

3. The Syndicate Alignment
When we build a tower in London, we don't stack random capacity. We align markets that have a proven history of following the lead carrier without friction.

Cheap capacity is easy to find.
Reliable capital requires a rigorous selection process.

Do you know the claims’ reputation of the carriers on your current tower?

DM me "CAPITAL" and I'll tell you how they actually perform under pressure.

Executives, there are two ways to protect your personal assets and your financial institution’s balance sheet in 2025…

1. Buy insurance. Hope it works.

2. Engineer a risk management program so resilient, it becomes a strategic asset.

Many still do the first. 

Even the sophisticated ones.

That’s why I’ve spent 25 years - and over 85,000 hours - mastering the second.

From building multimillion-dollar divisions at Marsh, JLT, and NFP…to recovering over $250 million in claims for clients…to founding LION Specialty, a boutique insurance firm built for the institutions who can’t afford to settle for off-the-shelf solutions.

Today, I help financial institutions, private equity firms, and insurance carriers, MGAs and ILS funds:

→ Navigate the global insurance markets.
→ Gain direct access to the best underwriters in the U.S., Bermuda, and Lloyd’s.
→ Structure D&O, E&O, Cyber, and complex P&C programs that hold up under real-world stress.
→ Align coverage with board priorities and capital strategy, not just next year’s premium.

We stress test programs annually like regulators would. 

We optimize every renewal. 

We've honed our claims playbook over three decades. 

Because in our world, you don’t get rewarded for being insured. You get rewarded for being prepared.

Building the New Standard:

At our insurance brokerage firm, LION Specialty, we’re building more than a brokerage. 

We’re building the broker of the future...

→ Delivering boardroom-grade insights to thousands of institutions through our weekly "Boardroom Briefings," and daily insights via our social platforms.
→ Attracting elite talent through a high-performance compensation model and culture.

Our mission: 

Obsess over every detail, so you don’t have to. 

Obsess over our execution. 

So you feel like you’re our only client! 

If your institution is ready to rethink insurance as more than a commodity - and turn it into an edge - I’d welcome an opportunity to connect! 

- Mark “FLIP” Flippen 

Mark Flippen

Arguably no better way to decompress from a long week than watching one of your kids in a play about nature’s rejuvenating power…

The play was based on the “Secret Garden,” a classic children's novel by Frances Hodgson Burnett first published in 1911.

It’s the story of Mary Lennox, a neglected girl sent to live in her uncle's gloomy manor in Yorkshire after her parents die in India. 

There, she discovers a hidden, locked garden and, with the help of a local boy named Dickon and her sickly cousin Colin, brings the garden back to life, which in turn heals and transforms all three children and the household. 

The book is celebrated for its themes of nature's healing power, friendship, and personal rejuvenation. 

Layla and her group from Denver Christian did a spectacular job bringing the story to life in our wonderful performing arts theater. 

How are you rejuvenating this weekend?

CEO & Co-Founder, LION Specialty | Insurance Broker | 25+ Years Helping Insurance Companies, MGAs & Insurtechs Protect Their Executives & Balance Sheets | $250 Million Claims Recoveries | Corporate Liability Specialist

I’ve been doing this new thing lately that catches many people totally off guard. 

When I meet other insurance industry professionals here on LinkedIn, I offer up a quick ten to fifteen minute coffee chat. I’ve met so many cool people lately doing this. Just another simple way to himanize all this networking stuff. 

It’s still a people business last time I checked! 

Please let me know if you’d like to connect and grab some time. 

No offense to the vets, but my favorite recent chats are with the younger pros that are either just starting out, the ones still in their first few years, or the one I did just yesterday with a sharp mid-career pro. We talked about his young family. He has number two on the way, and it was fun for me to reminisce a bit in my mind about that stage in my own journey.

Oh and if you happen to be reading this, and have gotten to this point and you have no idea who I am!

Hello. I’m Mark Flippen, most call me FLIP. 

I’ve spent over 25 years in the insurance business with about 20 of those specializing in the FI brokerage space… working w financial institutions, private equity firms and high-performance financial services businesses. 

I’m one of the managing partners and co-founders of LION Specialty. We’re a boutique insurance broker with a platform and high performance team that brings Fortune 500-level service to firms just below the radar of the mega-brokers. 

Because they deserve it too! 

If any of this sounds interesting or you just want to talk shop, my contact deets are in my profile. Feel free to DM too. Our team also writes a weekly Boardroom Brief that now goes out to over 2500 industry executives and financial professionals - with the three events and articles we think our clients won’t want to miss. It’s a quick scannable five/six min read w our thoughts and opinions on how that week’s events might move the market. 

Check it out and subscribe here: 

https://lnkd.in/gP22wvyF

P.S. I post here most days about insurance: our client service process, case studies and client success stories from my all my years in the business. And the occasional personal post about living with teenage daughters, my wife of 22 years and my faith journey. Follow along if you’d like! 
Mark Flippen

I was recently watching Jesse Itzler talk about running 100-mile ultramarathons. He said the graveyard of the race is Mile 40.

That is when the unadulterated pain sets in.

Your body screams at you to stop.
Most people listen, and they fold.

Before we launched LION Specialty, an industry legend gave us one piece of advice worth remembering…the people who win don’t have a better playbook…they just don’t quit when the plays don’t go their way.

He also warned us that most people can’t do this. 

The difficulty breaks them, and they tap out.

Two years into building LION, I understand exactly what he meant.

A few weeks ago, we had a seven-figure placement with a new client die one week before the set close date. Gone. The kind of moment where every voice in your head says this isn’t going to work.

That was a Mile 40 moment.

And we’re still running. The team didn’t flinch. We reset and got back to work.

It’s that kind of experience we’ve endured over the years. And exactly why we built LION and the LION Operating System. When your broker has been through Mile 40, they don’t wait until week-of to find out your program has a problem.

Doing anything meaningful in life is often hard.

But also deeply worth it when you have the right mindset and the resolve to keep moving after the hit lands.

Here is what struck me most about the Itzler video: he always finishes. 

When the agony hits, he doesn’t panic. He confronts it.

He says out loud: “Where the hell have you been? What took you so long?”

He expects the suffering. He knows it is the price of admission.

That is the exact mindset required to build a company.

The pain isn’t a signal that you are failing. It’s a signal that you are finally in the race.

You can’t avoid the difficulty of building something great.
You just have to change how you greet it.

If you’re building something that matters and you’re past your Mile 40…I’d like to hear about it.


P.S. That deal that died? It will come back. Or we’ll win the next one. Either way, we’re still building something great.

Engineered Insurance Outcomes for Financial Institutions | CEO & Co-Founder, LION Specialty | D&O · E&O · Cyber · Crime · Fiduciary · EPL | $250M+ in Claims Recovered

Someone told me I couldn’t do my job until I was 35. What in the! 
I was in my late twenties, closing deals in the small-market space, having real success. 

Then a mentor said something that infuriated me…

“You can’t advise the bigger accounts until you’re at least in your mid-thirties.”

Here’s why he was right.

The people across the table on a sophisticated D&O placement, CEOs, CFOs, General Counsels, are typically in their forties and fifties. 

They’re trusting you with coverage that protects every personal asset they own. Nobody wants to tell their board a twenty-seven-year-old is the lead on that program.

It stung. 

Still does a bit writing about it all these years later. But the second part of his advice was the real gift.

He said spend the years between your late twenties and mid-thirties doing two things.

1. Get technical 

Find a team where you can learn how teams work. Where you can learn the products cold. Master the contract language so you can go line-by-line with a General Counsel. Then be able to explain it simply to a CEO who needs the answer in ninety seconds. Bonus points if that team specializes in an industry! 

(Be patient w it all, it’s hard work) 

2. Build the relationships that get deals done 

Know the markets. Know who picks up the phone when you need a binder at 4pm on a Friday in the summer. Or you’re dealing w claim on the weekend. 

A lot of young producers skip this second part.

Here’s what nobody tells you about the small-market hustle…

…it’s a hamster wheel. 

Many buyers care about price and who shows up most. You can win, but you’ll burn out chasing accounts that don’t reward the skills you need for the next level.

I had this conversation with a young professional this week. She reminded me of myself at that age. I told her the same thing.

I could see the gears grinding. 

The people who hear this and get frustrated, but realize it’s right and still do the work…those are the ones we want to find.

They’re the ones that will be the best. 

If you liked this post, you might be a LION! And you might also like our Wednesday Intelligence blog. I share war stories from 20+ years protecting executives in the Boardroom. 

Comment “WED.” and I’ll send you the link.

P.S. if this resonates and you’re in your late 20s looking for that team, my DMs are open always!

He ran operations for dozens of tech companies. Then he walked into a church where nobody knew his name.

If you’ve been scrolling the gram lately and you’re into faith-based stuff, you’ve probably seen the Duomo ads.

The one that got me was this cool looking dude in a cowboy hat talking about God.

I wanted to go hang out with that guy instantly.

So I went down the rabbit hole. Turns out the guy who built Duomo is Artem Kopaniev. For five years he was COO of one of the largest tech ecosystems in Eastern Europe. The kind of role most wouldn’t dare step away from to do what he’s doing now.

Building a Bible app!

The leaving part I get. Been there. Left a cushy job in big broker corporate America a couple of years ago.

What got me was how he started.

He didn’t go the typical tech founder route. Hire the big team. Raise a bunch of money. Build the prototype. Etc. 

He went and spent time in Christian communities as a total stranger. 

Sat with the people. Asked all the questions. Tried to understand — not just what they needed from technology, but whether he actually shared the values he wanted to build around.

Most founders start with a market. Artem seem to start with a mirror. 

And it reminded me of a lesson I’ve been deep in over the past few years.

You can’t take people somewhere you haven’t been yourself.

Artem spent a year doing that before he wrote a single line of code.

Interviewing people. Testing every faith app on the market. Sitting in rooms where nobody knew who he was or his track record.

He said something that stuck with me…strangers showed him interest, offered help, asked what brought him there. That experience of being held by a community before you’ve earned anything, became the foundation of the product.

Duomo has 100,000 downloads now. Team of 25, people who left these huge tech cos like Glovo, Bolt, and Genesis to work on this. Real traction.

But the part I keep coming back to isn’t the numbers.

It’s a senior executive sitting in a room full of people he didn’t know, asking himself whether he believed what they believed before he tried to build something for them.

That’s not something you put in a pitch deck.

graphical user interface, text, application

The Delaware Supreme Court just told AIG, Chubb, and Berkley their favored M&A fine print doesn’t work the way they thought it did.

For years, D&O insurers have used the “bump-up” exclusion to shut down payouts on merger price lawsuits. 

If a case looked like a fight over deal value, they’d often pay the lawyers but refuse to fund the settlement.

The Harman decision blows a hole in that.

In a 3–2 ruling, Delaware’s high court said it’s not enough for insurers to call it a price dispute. 

They have to show the settlement actually functions as a higher deal price. In Harman, they couldn’t. 

The settlement went to investors beyond just those who tendered into the deal, and insurers (DE said) never put in real evidence that the payout was topping up the per-share price.

The bottom line now for carriers…

…prove the dollars are a price increase before using the bump-up to walk away from a settlement.

That quietly shifts negotiating leverage for every financial institution board with M&A in the plan.

And bump-up is only one of three hidden trouble spots in a single deal.

There’s a straddle gap between your tail and your go-forward D&O. When a lawsuit reaches back before closing and forward after closing, each insurer can argue “not my problem,” unless you’ve fixed that language up front.

Then there’s a growing idea overseas called “stepping stone liability.” 

That’s where a company’s legal breach becomes the stepping stone to personal claims against individual directors. We speculate that Cyber incidents may be one of the pressure points people start  watching closely.

Three gaps. One transaction.

Boards that tighten all three before the next deal won’t just be following sound protocol — they’ll be negotiating from a stronger position than peers who don’t.

We broke down all three this week with specific fixes for each. 

Comment BRIEF and we’ll get you subscribed.

Stay covered out there everybody! 

LION Specialty 

P.S. if you like this post you’ll love our daily posts too! Follow along at Mark Flippen and Natasha I. Kiemnec, ARM

LinkedIn network: need your help on two fronts…data extraction and policy form / coverage analysis. If you are doing anything interesting around automation or AI on either of these fronts, let’s connect. 

If you know of anyone doing anything interesting, feel free to tag them in the comments. 

Happy to share what all I learn here too with anyone that’s interested. 

Let’s all win together! 

Please comment, like and repost for reach here, if you’re interested in this too

Thnx y’all ! 

P.S. Depending on response I’ll likely write more about this in an upcoming edition of the LION Specialty Boardroom Briefing. Subscribe, if you’re not already on the distribution!

Everyone is talking about AI in insurance.
Nobody is talking about what happens when it fails at scale.
The current conversation splits into two lanes... 

AI as an efficiency tool. 
Faster underwriting, better loss ratios, leaner claims ops. 

Or AI as a client-side risk. 
What agencies and brokers need to watch for their E&O exposure.

Both miss the third frame.

The systemic one.

Right now, competing carriers are embedding the same foundation models, the same vendor platforms, and the same training data into their core workflows... underwriting, claims, distribution, compliance.

Correlation? 

When one model misfires, one carrier has a problem. 

When the same model is running inside dozens of carriers simultaneously mis-pricing the same risks, misinterpreting the same policy language, misrouting the same claims — the insurance system has a problem.

We have stress-tested correlated catastrophe risk for decades. We have not stress-tested correlated AI failure.

That work needs to start.

P.S. If you liked this post, you'll love our Boardroom Briefings. We cover ongoing and emerging risk issues for financial institutions every week. Comment "BRIEF" for the link. Or see the link in my featured section. In the meantime, see a few blurbs on our latest editions, in case you missed them!

Boardroom Briefs 

This client transformation defines it.

When we set up LION it was to solve the exact problem we wrote about this morning.

A General Counsel we’d worked with years ago moved to a new institution.

Publicly traded southeastern regional insurer. Complex risk profile.

She knew the program deserved a harder look.

A D&O claim had hit.

The renewal that followed was difficult. The risk itself hadn’t become unmanageable. 

After working on hundreds of claims…

When you’re approaching a renewal with one, all aspects of the broker’s process are under the microscope.

This one seemed to become difficult because the broker process surrounding it broke down.

The timeline seemed to get compressed.

To the point where the C-suite was left binding coverage without the former team fully presenting all available options.

The account produced meaningful premium.

Just not enough commission revenue for the mega-broker to send its A-team.

When this insurer client needed it. 

So she brought us in. Her CFO had become President. He’d seen our work before too. Back in our JLT days. 

One meeting with them and leadership made the call.

They launched the next renewal 150 days out. Got in front of the carriers directly. Gave underwriters the full context on the claim…what it meant and what it didn’t.

The markets heard the overall great story of the business too. 

Carriers got comfortable.

Incumbents stayed on the program. 
Premiums even came down. The board got fresh limits for the first time in a couple of years — they’d been operating under an extended reporting period with a limited fresh aggregate.

The leadership team at that institution made one decision that changed everything.

They stopped accepting a process that didn’t match the complexity of their risk.

We wrote the full case study in this week’s Wednesday Intelligence Boardroom Brief. 

Tash and I also took a few minutes and broke it all down in the audio version, too. 

Comment BRIEF for the link.

MuddyWater Doesn't Check Your Zip Code: How the Iran War Impacts US Insurance Company Operations…

Regional and Mutual Insurers, MGAs, you don’t trade with Iran.

You have zero Gulf exposure. No marine book. No aviation program. No political violence coverage.

But your social inflation exposure just changed.

Your cyber risk just got elevated.

And reinsurance costs might get pressured now.

One conflict. Three risk channels being impacted. 7,000 miles away.

This week Iran’s MuddyWater group was confirmed active on a US bank’s network. 

Confirmed by Symantec, flagged by CISA. 

They infiltrated a financial institution in Egypt before the first bomb dropped. They’ve built custom malware targeting fuel systems inside the United States.

There are dozens of Lloyd’s-approved war exclusion wordings for cyber policies. They’re built on four model clauses that disagree on the attribution standard. Some require government attribution. 

Some give the insurer sole discretion. 

If a regional institution gets hit with ransomware traced to an Iranian state actor, which clause is in your policy determines whether you have coverage or a multi-year dispute? 

Meanwhile, diesel is up 20%. 

Gasoline went from $2.98 to $3.48 in two weeks. Every auto, property, and commercial lines claim just got more expensive, and most boards are now scrambling to make the  connections to impacts from the Iran war. 

Meanwhile, President Trump just signed a cybercrime executive order with a 120-day implementation timeline and no CISA director in the seat.

Three channels. 
One conflict. 
Zero time to wait.

We broke all of it down in this week’s Boardroom Brief…what your professional liability underwriters are going to ask about at your next renewal, and what you can do now to be ready.

Comment BRIEF or join directly 

here: https://lnkd.in/e8qkpZkY

Stay covered out there everybody!

I read a dozen insurance market reports.

The most important intel wasn’t in any of them.

Every report celebrates buyer-friendly conditions. Rate reductions. Carrier competition. Expanded capacity. The tone is reassuring across the board for buyers. 

But none of them address:

→ The coverage erosions hiding behind rate decreases

→ Why “average” rate reductions mean nothing at the account level

→ The reinsurance-to-primary disconnect in casualty that nobody’s mapping

→ Claims advocacy, completely absent from all of them

(Trends, sure. Yet no actionable recommended strategies, as a result) 

→ Silent AI exposure sitting in existing programs right now

→ The reserve development problem behind those clean combined ratios

→ What broker consolidation actually does to the client experience

→ The regulatory patchwork creating coverage gaps no standard form addresses

And the one thing the reports will never say…

…the soft market is when brokers get complacent. 

Renewals become transactional. Submission quality drops. 
Market relationships go unworked.

Good conditions are exactly when your broker should be working hardest.

Should I break these down?
Maybe a future Wednesday Intelligence blog? 


P.S. If you liked this post, you’ll love our free weekly Boardroom Brief. Every Friday we break down the three most important events in the global insurance market and how we’re advising our clients to respond.

And follow me Mark Flippen for nearly daily posts about the business!

Two federal judges ruled on AI and “privilege,” the same week.
They reached opposite conclusions.

One held that using a consumer AI chatbot defeated confidentiality. 

The other treated AI as a drafting tool, not a separate “person” for waiver purposes.

CEOs, CFOs, and board members at regional insurers, MGAs, and mutuals…

In Manhattan, Judge Rakoff stripped privilege from 31 documents a defendant created using a consumer AI chatbot.

In Michigan, Judge Patti held that AI-assisted litigation drafting is protected work product.

In my 20+ years placing coverage for financial institutions, I’ve seen the pattern…

→ Courts apply existing doctrine to new technology
→ The uncertainty itself creates exposure
→ Early movers on governance capture the advantage

Meanwhile, a federal court allowed statutory bad faith and unfair-trade-practices claims to proceed over undisclosed AI use in claims handling.

And we map five specific risk vectors for P&C carriers, from discoverability of model configuration to override rates that signal rubber-stamping.

For our friends on the claims and legal side…

…what’s your take on all of this? 

(please weigh in in the comments!) 

If you want the framework sophisticated institutions use to govern AI across legal, claims, and underwriting operations…

Read about it in this week’s LION Specialty ‘Friday Five’ Boardroom Briefing.

Comment “BRIEF” below if you’re not on our distribution…

Stay covered out there yall!

P.S. The FMG annual report alone is worth your weekend skim. 108 pages, 26 states, dozens of major bad faith and coverage cases from 2025. 

“The LION Specialty Claims & Legal Edition”

If you’ve ever wondered whether your insurance will work in a claim, here’s the breakdown of how we help our clients get comfortable with that every year.

Your broker renews your insurance every year.

Regional insurers, mutual carriers, and insurtech companies…

…when was the last time anyone stress-tested your own insurance? 

There’s a difference between renewing coverage and evaluating whether it still works.

Every LION client’s program goes through an 8-point stress test annually. 

Not at some renewals. 

Or just when something goes wrong. 

Every year…whether the market moves or not.

Here’s what gets tested:

𝟭. 𝗠𝗮𝗿𝗸𝗲𝘁 𝗽𝗼𝘀𝗶𝘁𝗶𝗼𝗻𝗶𝗻𝗴.

Is your program placed with the right carriers for where your risk profile sits today. 

Have you seen options in the US, London and in Bermuda?

𝟮. 𝗖𝗮𝗿𝗿𝗶𝗲𝗿 𝗰𝗼𝘂𝗻𝘁𝗲𝗿𝗽𝗮𝗿𝘁𝘆 𝘀𝗲𝗹𝗲𝗰𝘁𝗶𝗼𝗻.

Not just financial strength ratings. How does this carrier behave when you file a claim? How fast do they pay? How often do they deny? 

Two decades of tracked claims behavior answers that.

𝟯. 𝗖𝗼𝘃𝗲𝗿𝗮𝗴𝗲 𝗲𝗳𝗳𝗶𝗰𝗮𝗰𝘆.

Manuscript versus off-the-shelf. Exclusion creep. Endorsements that contradict the coverage grant on page four. 

The language that looks fine until it doesn’t.

𝟰. 𝗕𝗲𝗻𝗰𝗵𝗺𝗮𝗿𝗸𝗶𝗻𝗴 𝘄𝗶𝘁𝗵 𝗹𝗼𝘀𝘀 𝗺𝗼𝗱𝗲𝗹𝗶𝗻𝗴.

Where do your limits, retentions, and pricing sit against peers with similar asset profiles? 

The national averages + your actual peer set.

𝟱. 𝗟𝗶𝗺𝗶𝘁𝘀 𝗼𝗳 𝗹𝗶𝗮𝗯𝗶𝗹𝗶𝘁𝘆.

Adequacy tested against real exposure, not the number bought five years ago and kept rolling forward.

Are these appropriate now? 

𝟲. 𝗥𝗲𝘁𝗲𝗻𝘁𝗶𝗼𝗻𝘀.

Calibrated to your risk tolerance and claims history, not rounded to the nearest clean number.

Is this within your risk tolerance today. 

𝟳. 𝗣𝗿𝗶𝗰𝗶𝗻𝗴.

Validated against the current market, not last year’s indication with a percentage tacked on.

Is it competitive in this cycle? 

𝟴. 𝗙𝗶𝘁 𝗳𝗼𝗿 𝗽𝘂𝗿𝗽𝗼𝘀𝗲.

Will it work the way it’s supposed to during a claim? Does the whole structure still match how you actually operate? New business lines. New geographies. Board changes. M&A activity. 

The program has to move when you move.

Eight dimensions. Every year.

Many regional insurers, mutual insurers, and insurtech companies have never had their own insurance looked at this way.

Ready to see how your program holds up? 

DM me “STRESS TEST.”

Not ready yet? Follow along in the Boardroom Brief — the link is in the comments.

Insurance Stress Test Breakdown 

“They won’t roll over. But we always get to a reasonable place with these people.”

A claims attorney said that to me in 2006. It changed how I managed claims forever. 

We’d just filed the first major claim I ever worked on. 

It was for an investment management client. An SEC investigation that consumed the entire management team. The board wanted updates twice a month from the CFO and GC. 

It was a horrific experience, on one hand. And immensely educational on the other.

I was at Willis at the time and working with one of the best claims attorneys on our team. 

In a professorial way, he schooled me first on the people aspects. Who we would be working with at the carrier(s). How they would handle it all. Based on his experience handing hundreds of claims with them. 

Arguably the most important piece. 

Then he did the same breakdown on the proper systems and workflows that I / we would follow. 

It was systematic at every turn. That experience built the claims advocacy system we run at LION today. Now all these years later, after $250 million in our own recoveries, here’s the full system breakdown… 

Nine steps. Three phases.

𝗣𝗵𝗮𝘀𝗲 𝟭: 𝗖𝗮𝗿𝗿𝗶𝗲𝗿 𝗦𝗲𝗹𝗲𝗰𝘁𝗶𝗼𝗻

𝟭. 𝗖𝗮𝗿𝗿𝗶𝗲𝗿 𝗣𝗮𝗿𝘁𝗻𝗲𝗿 𝗦𝗲𝗹𝗲𝗰𝘁𝗶𝗼𝗻
Choose carriers based on claims behavior, not just financial ratings.

𝟮. 𝗖𝗹𝗮𝗶𝗺𝘀 𝗕𝗲𝗵𝗮𝘃𝗶𝗼𝗿 𝗦𝗰𝗼𝗿𝗶𝗻𝗴
Score pay speed, denial frequency, and gray coverage posture across decades of data.

𝟯. 𝗥𝗲𝗹𝗮𝘁𝗶𝗼𝗻𝘀𝗵𝗶𝗽 𝗕𝘂𝗶𝗹𝗱𝗶𝗻𝗴
Build relationships with claims decision-makers before you need them.

𝗣𝗵𝗮𝘀𝗲 𝟮: 𝗣𝗿𝗲-𝗟𝗼𝘀𝘀 𝗣𝗿𝗲𝗽𝗮𝗿𝗮𝘁𝗶𝗼𝗻

𝟰. 𝗣𝗹𝗮𝗰𝗲𝗺𝗲𝗻𝘁 𝗡𝗲𝗴𝗼𝘁𝗶𝗮𝘁𝗶𝗼𝗻𝘀
Align intent of cover through the actual contract language.

𝟱. 𝗘𝘅𝗰𝗹𝘂𝘀𝗶𝗼𝗻 𝗡𝗲𝗴𝗼𝘁𝗶𝗮𝘁𝗶𝗼𝗻
Remove or narrow exclusions that create problems in likely claim scenarios.

𝟲. 𝗥𝗲𝗽𝗼𝗿𝘁𝗶𝗻𝗴 𝗜𝗻𝗳𝗿𝗮𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲
Document protocols so your team knows exactly what to do in the first 24 hours.

𝗣𝗵𝗮𝘀𝗲 𝟯: 𝗣𝗼𝘀𝘁-𝗟𝗼𝘀𝘀 𝗘𝘅𝗲𝗰𝘂𝘁𝗶𝗼𝗻

𝟳. 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗖𝗹𝗮𝗶𝗺 𝗣𝗿𝗲𝘀𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻
Frame the loss in terms that align with coverage intent.

𝟴. 𝗘𝘀𝗰𝗮𝗹𝗮𝘁𝗶𝗼𝗻 𝗠𝗮𝗻𝗮𝗴𝗲𝗺𝗲𝗻𝘁
Know when to push, who to call, and how to frame it.

𝟵. 𝗣𝗼𝘀𝗶𝘁𝗶𝗼𝗻𝗶𝗻𝗴 𝗳𝗼𝗿 𝗥𝗲𝗰𝗼𝘃𝗲𝗿𝘆
Full-cycle advocacy from first notice through final recovery.

Nine steps. Three phases. 

Built from that 2006 education and 20 years of refining it.

The financial strength rating tells you they can pay.

This system is how we make sure they do.

DM me “CLAIMS” if you want to see how this maps to your program.

LION Claims OS 

It’s baked into everything we do. 

In 2005 I moved to New York City and was throw straight into the deep end. 

(the professional kind) 

I landed on a team handling some of the most complex financial institutions in the world. 

They didn’t just teach me insurance. They drilled a non-negotiable “process” into my head.

Every presentation had a strict structure. 

Every policy review had a checklist. 

Every client interaction was engineered to remove surprises.

At the time, I thought it was overkill.
I thought this business was about building relationships, taking people to lunch, and being the “fun broker.” 

I was so wrong. 

Because 20 years later, I know exactly who our process is built for.

It was built for you.

If you’re an executive buying D&O and E&O for your institution, you carry the weight of the company. 

When a $50 million claim hits, a “good relationship” with your broker won’t save your balance sheet. A golf outing won’t rewrite a bad policy exclusion.

Your risk profile is too complex for a broker who wings it.

You don’t need a friend in the insurance business. You need a bulletproof system.

A systematic process. 

That 2005 methodology I learned all the way back then is what runs LION Specialty today.

We run the playbook. We dissect the manuscript forms. We stress-test limits against actual market precedents.

We do the militant work upfront.

And we’re constantly fine tuning it. 

So when the worst-case scenario happens, you don’t have to hope you’re covered. 

The process best positions you. 

DM me if you want to see how our 150-day process maps to your next renewal.

In 2015, domestic E&O appetite tightened significantly for complex US insurance operations, especially outside the top 30 carriers.

Our friends and clients at regional and mutual carriers felt it first.

MGAs got hit hardest.

You were building something specialized…niche products, complex distribution, real underwriting expertise. 

The market was handing you forms written for a completely different business model. 

Miscellaneous professional services policies that had no idea what an MGA actually does.

Generic exclusions for the exact activities that define your model.

You were running an institutional-grade operation with retail-grade protection.

You deserved better. 

We saw it, and we went to work.

We went to London, worked with Lloyd’s syndicates who understood delegated authority, and built a Proprietary Manuscript Form around how MGAs actually operate. 

Starting with London’s best MGA wordings, re-engineered for U.S. independent operations.

- Professional services definitions broad enough to cover your full distribution and binding authority.

- Coverage that protects you when a capacity partner dispute turns adversarial.

- Terms that reflect your specific risk, not the general market’s fear of it.

That was 10 years ago.

Today, independent MGAs use this program because it’s one of the few forms they’ve found that actually fits their model.

You shouldn’t be carrying coverage that doesn’t understand your business.

DM me if you want to see how it compares to what you’re buying now…


P.S. want to go a bit deeper? Flip through this deck to see how we will differentiate your MGA in the market…

How We Go-To Market 

Your broker's renewal process started too late. Here's a 3-question test that proves it.

We've placed coverage for some of the largest financial institutions in the country. 

Banks, insurers, asset managers — complex programs where gaps cost millions and the wrong carrier decision shows up at the worst possible moment.

Every one of those engagements runs on the same framework. 

Three disciplines. We call them Orchestration, Rigor, and Execution.

You can use them to pressure-test your own broker in 60 seconds.

Ask your broker: When did our renewal strategy start?

Orchestration is timing. 

Our engagements begin 150 days before expiration — not 60 or 30. Every week your broker starts late is a market they didn't access and a term they couldn't negotiate. If your renewal feels rushed at the end, it was lost at the beginning.

Ask your broker: When was our last coverage stress test?

Rigor is testing. 

We stress-test every program annually across eight dimensions…carrier strength, limits adequacy, coverage structure, peer benchmarking and four more. A renewal without a stress test is just a transaction with a signature line. Most programs we inherit have 8-12 coverage gaps no one flagged.

Ask your broker: Can you show me the team’s credentials and the timeline?

Execution is delivery. 

Senior professionals on every account. Week-by-week delivery schedules in writing. 30% faster than industry standard. If your broker can't show you the people and the plan, your service model runs on good intentions.

Three questions. 

Specific answers or vague ones.

The vague ones are hiding gaps you haven't found yet.

If you like this post, you’ll love our weekly Boardroom Briefs. We break down the top three events impacting the global insurance markets. It’s a quick skimmable five min read that hits your inbox every Friday around 7am. Link in featured section. 

P.S. check out the additional details of our process…And follow along daily at Mark Flippen

our process framework: 

Most insurance company professional liability policies exclude the one thing insurance companies actually do for a living.

I had the same conversation twice last week with two different insurers. Both were in difficult claims. Both had E&O policies. Neither policy responded to what the claim was actually about.

Underwriting.

The very act an insurance company performs every day. And the act that generates the revenue that justifies having a professional liability policy in the first place, carved out of coverage.

A regional insurer gets sued over an underwriting decision. They turn to their E&O policy, the policy they bought to protect their professional operations. The carrier points to the "underwriting exclusion."

This isn't a one-off technicality buried in an endorsement nobody reads. It's standard language in many US insurance company professional liability forms. Narrow "insurance services" definitions paired with broad "arising out of" underwriting exclusions.

In too many programs, the operations that generate your exposure are the operations your policy may not respond to.

Both conversations ended the same way...with the recognition that the gap had been there from day one, long before anyone needed to know it existed.

Our Lloyd's-backed form is built specifically for US insurance operations. 

We start with the broadest professional services definition we can justify and carve back from there. It's all centered around your actual operations, not generic financial institution activity. Underwriting is expressly inside the four corners of coverage, not pushed out by default.

Underwriting is covered. Because it has to be.

If you're a regional or mutual insurer carrying a standard professional liability form, find out whether your underwriting operations are actually protected before you find out the hard way.

DM me. We'll read the policy together.

A Must Read for Insurance Company Executives 

Five catastrophe events. Zero physical damage. Billions to trillions uninsured.
That's the NDBI problem nobody's talking about. This week's Friday Five breaks down Non-Damage Business Interruption...ninety-two percent of S&P 500 value is now intangible, but most BI policies still require something to burn before they pay.

We also pulled apart the three-word clause in your cyber policy that stops paying a BI claim weeks before your business actually recovers. And I pinned a piece on why parametric insurance isn't coverage — it's a liquidity weapon.

In case you missed it: The Wednesday Intelligence Brief kicked off our deepfake miniseries. A finance director wired $25.6 million after a video call with his CFO, his CEO, and two colleagues. None of them were real. We broke down why FI executives are walking training data for synthetic clones and the six renewal questions every institution should bring to the table.

New this week: both editions are now available as audio. 
Read it or listen to it, your call.

Comment NEWSLETTER for the link.

View newsletter: LION Specialty Newsletter 

Welcome to the Pride's Friday Five Every Friday the team rips through 200+ insurance, legal, and market-risk articles into three signals your board ca

Open article: Five Catastrophe Events. Zero Damage. Billions Uninsured. The "NDBI" Issue No-one is Talking About, and The LION POV! by Mark Flippen • 2 min read

Five Catastrophe Events. Zero Damage. Billions Uninsured. The "NDBI" Issue No-one is Talking About, and The LION POV!

Until I walked away from the corporate broker machine, I never fully appreciated the pressure two types of clients were under…

(I thought I understood it)

But I was missing the most important ingredient.

Nassim Taleb wrote an awesome book about it called, “Skin in the Game.”

His core argument is simple.
You cannot truly understand a system unless you have something to lose in it.

“The bureaucrat takes risks but pays no penalty.”
“The advisor gives the recommendation but bears no consequence.”

For years, I was that advisor.
I was a corporate broker for the largest financial institutions in the world. Working at some of the largest brokerages in the world. 

I gave the advice. I structured the deal. I negotiated the terms.
But if the deal went south?

I still had a salary.
I still got a bonus.
I still had a brand name on the door.

The worst thing that could happen to me was a bad review.

The worst thing that could happen to my client was bankruptcy.

That gap between “bad review” and “bankruptcy” is wild when you actually wrap your head around it. 

When we walked away from it all to build LION Specialty… 

Somewhere during that first year I felt it.

I finally understood the two people I serve most…

1.	The MGA Founder

You aren’t just building a business; you are building a reputation on borrowed land.

Your capacity provider(s) is like a  landlord. If they pull the paper, you don’t just have a bad quarter.
You could have an empty office.

I used to look at capacity as a “market condition.” Now I see it as oxygen.

2.	The Insurtech Founder

You are running a race against a burning wick.

You have investors breathing down your neck and regulators watching your every move.
One compliance slip, one bad loss ratio, and the term sheet disappears.

I used to look at your burn rate as a “metric.” Now I feel it in my chest.

I was a good broker before.
But I was safe.

Now, I look at your P&L and I don’t just see risk.

I see the late nights. The missed dinners. The terror of the “what if.”

I don’t just place your insurance anymore.

I help defend your survival.

Because now, I’m in the arena with you.

undefined undefined

I Help Executives Turn Insurance Into A Competitive Asset & Protect Their Personal Net Worth | Managing Partner & Co-Founder of LION Specialty | Expert in Corporate Liability Insurance 

There are two ways to protect a financial institution in 2025:

1. Buy insurance. Hope it works.
2. Engineer a risk management program so resilient, it becomes a strategic asset.

Many still do the first. Even the sophisticated ones.

That’s why I’ve spent 25 years — and over 85,000 hours — mastering the second.

From building multimillion-dollar divisions at Marsh, JLT, and NFP…to recovering over $250 million in claims for clients…to founding LION Specialty, a boutique insurance firm built for the institutions who can’t afford to settle for off-the-shelf solutions.

Today, I help financial institutions, private equity firms, and insurance carriers:

→ Navigate the global insurance markets.
→ Gain direct access to the best underwriters in the U.S., Bermuda, and Lloyd’s.
→ Structure D&O, E&O, Cyber, and complex P&C programs that hold up under real-world stress.
→ Align coverage with board priorities and capital strategy, not just next year’s premium.

We stress test programs annually like regulators would. We optimize every renewal. We've honed our claims playbook over three decades. 

Because in our world, you don’t get rewarded for being insured. You get rewarded for being prepared.

Building the New Standard:

At my new insurance brokerage firm, LION Specialty, I'm building more than a brokerage. I’m building the broker of the future...

→ Delivering boardroom-grade insights to thousands of institutions through our weekly "Boardroom Briefings," and daily insights via our social platforms.
→ Attracting elite talent through a high-performance compensation model and culture.
→ Making every client feel like they’re our only client.

If your institution is ready to rethink insurance as more than a commodity — and turn it into an edge — let’s talk.

- FLIP

taplio

The Battle

Natasha Kiemnec

Mark Flippen

Followers

Posts

Engagements

Likes

Performance ScoreNatasha Kiemnec's LinkedIn Performance

Performance ScoreMark Flippen's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Natasha Kiemnec

Mark Flippen

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Natasha Kiemnec's LinkedIn Performance

Performance ScoreMark Flippen's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreNatasha Kiemnec's LinkedIn Performance