Lion Specialty

Podcast Co-Host - Conversations in the LIONS' DEN

Co-Founder & Managing Partner

NFP is a leading insurance broker and consultant that provides employee benefits, property & casualty, retirement, and individual insurance and wealth management solutions through our licensed subsidiaries and affiliates.Our expertise is matched only by our personal commitment to each client’s goals.

Senior Vice President

Marsh McLennan

Vice President

JLT Specialty USA

JLT Specialty USA is the U.S. platform of the leading specialty business advisory firm Jardine Lloyd Thompson Group. Our experts are specialty focused and have extensive experience in industries and products serving leading U.S. and global firms. We focus on complex areas of industry or product need, where innovation and optimization are critical. 

Our specialty team has clear alignment around our clients’ best interests and are judged and rewarded based on our clients performance. With decisive insights, our team is fact-based and analytics-driven to create the best insights and value for our clients. 

Our culture enables a rewarding and challenging environment to attract and develop the best talent in the industry. We encourage creativity and are free to challenge conventions. With teamwork and collaboration, we are working together to share knowledge, solve problems and deliver the best solutions for our clients. 

Jardine Lloyd Thompson is one of the world’s leading providers of insurance, reinsurance and employee benefits-related advice, brokerage and associated services. JLT’s client proposition is built upon its deep specialist knowledge, client advocacy, tailored advice and service excellence. JLT is quoted on the London Stock Exchange and owns offices in 40 territories with more than 10,600 employees. Our global foundation is unparalleled and provides experts worldwide in 135 countries. 

For further information about JLT, please visit our website www.jltus.com

Broker Director and Officer's liability insurance for clients around the globe.

Assistant Vice President

The Aspen Institute

Development Intern

American Property Solutions

Developed Business Plan

Bitzer Real Estate Partners

Intern

LION Specialty is one of the only independent broker that positions financial institutions clients to trade effectively in the global insurance markets.

As Co-Founder and Managing Partner at LION Specialty, I offer a distinct combination of skills and a personalized approach to navigate the dynamic landscape of the global insurance market.
Our focus lies in empowering middle-market financial institutions, which are frequently overlooked by larger brokerage firms, by providing them with innovative tools for risk management and decision-making.

With our long-standing global relationships and experience, we elevate these institutions with our innovative solutions and client service platform.
What sets us apart:

• Decades of experience in our niche, with accolades for our team's effectiveness.
• Exclusive access to a Lloyd's of London program, a rarity in our field.
• Recognition from our peers as one of the best teams to work with.
• The ability to keep our clients up to date with dynamic market conditions with the use of AI tools.

I have 50,490 hours of expertise within the insurance industry focusing specifically on banks, (Re)insurance companies, private equity firms, ILS funds, and investment managers.

My passion lies in developing distinctive solutions tailored to meet the specific needs of each client.
Since the start of my career, I’ve always been driven and results-oriented. Always willing to put in the extra hours and time to get the job done.

After starting in real estate, I jumped over to the insurance world where I teamed up with LION’S co-founder, Mark Flippen. 

Within months, the two of us were landing and converting meetings at a rapid clip. Our passion for insurance and our strong work ethic led us down the path of creating LION Specialty. 

Outside of the financial industry, I enjoy teaching Pilates, exploring the world, and spending time with family and friends.

Interested in discovering how our decades of experience contribute to enhancing the effectiveness of insurance companies in the commercial insurance market? Send me a message and let's connect.

Natasha I.  Kiemnec, ARM

This industry runs on relationships.
Today I'm grateful for every single one.

The clients who trusted us before we had a track record. 

The carriers who partnered with us when LION was just an idea and a business plan. 

The team members who bet their careers on what Flip and I were building.

We started LION with a simple belief: financial institutions deserved better.

Better coverage. 
Better advocacy. 
Better understanding of what they were actually buying.

What we didn't anticipate was how many people would show up to help us prove it.

Underwriters who spent extra hours getting manuscripts right. Clients who referred us before we asked. Industry friends who made introductions just because they believed in what we were doing.

Insurance is a relationship business. 
Everyone says it.

But you don't really understand it until you're building something from scratch and watching people choose to support you; not because they have to, but because they want to.

To our clients: Thank you for trusting us with what matters most.

To our carriers: Thank you for partnering with us to build something different.

To our team: Thank you for making LION what it is.

To Mark Flippen for making the leap with me, and trying something that virtually no one in our industry does. 
 
To this industry: Thank you for twenty years of relationships that turned into friendships.

To the new connections: We’re learning how to build in public and on socials because of you!

To my family and friends: I love you for all the support helping me get to this point!

To my love David Gutierrez, your unwavering love and support has made this possible for me. 
 
Happy Thanksgiving to everyone who's been part of this journey.

Today I'm not thinking about coverage gaps or policy language.

Just gratitude and love ❤️

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

If your insurance policy is 200 pages long, it's probably hiding something.
Ours is 35:

I've spent the last 10 years reading what most people avoid…
Hundreds of pages of insurance forms. 

I've tracked how they perform at claim time, mapped exclusions that didn't hold up, and watched policy language fail when it mattered most.

So believe me when I tell you this: complexity isn't protection.

LION’s solution is our Lloyd's Manuscript.

We're now on version four.

Not because we keep getting it wrong. 

Because we keep making it better.

Version one: At JLT, we picked the top 20 writers of insurance company professional liability - basically everyone who writes it - and reviewed their contracts section by section.

Insuring agreements. 
Notice provisions. 
Defense and settlement. 
Allocation. 
Exclusions with carve-backs.

We crafted language simple enough to understand but sophisticated enough for London to back it.

Version two: Public company variation. 

Realized the private company version needed tweaks we hadn't caught the first time.

Version three: Left for another firm. 

Couldn't take our IP. Had to write it again from scratch - which forced us to see what had become outdated, where definitions didn't match up.

Version four: Built LION. 

Rewrote it completely. More succinct. Reordered exclusion sections. Pulled general terms into one place. Made notice crystal clear.

Each iteration taught us something:

How "for" lead-in language on conduct exclusions creates full defense cost carve-backs. 

How "true best effort" allocation language performs under pressure. 

How integrated forms beat 50+ endorsements stitched together.

Here's what four versions got us:

Technical precision: Covers full scope of FI services. Flexible claims trigger. Exclusions with carve-backs for how insurers actually operate. 

Optional punitive damages through London, Bermuda, Ireland. Integration with reinsurance that fills gaps where you'd otherwise pay.

Structural elegance: D&O, E&O, EPLI, fiduciary in clear sections. 

Crime and cyber as modular add-ons. 35 pages of core coverage vs industry standard 150+.

Market validation: Primary capacity to $10M. Excess to $100M in UK. Nine Lloyd's syndicates pre-approved. Tested through countless real claim scenarios.

Most brokers place your business into existing structures.

We build structures designed specifically for your business.
Because we don't write to impress.
We write to respond.

If you want to chat about coverage, my DMs are always open.

Want boardroom intelligence with zero noise?

Every week we share curated insights that cut through the chaos and help you make the best policy decisions.

Join here: https://lnkd.in/garzxSxG

LION Specialty. The Leader in Institutional Insurance.

JSESSIONID

li_at

15 years in insurance taught me what no training manual covers.
Here are the unspoken rules that matter most:

1. Your relationships matter more than your resume

The best placements don't come from knowing products. 

They come from knowing the underwriter who can make exceptions, the claims executive who will fight for your client, the coverage counsel who understands nuance.

Build relationships before you need them.

2. Saying no is a skill

Early in my career, I said yes to everything. 

Every client call. 
Every project. 
Every "quick question."

I learned the hard way: overcommitment leads to mediocre work. Boundaries create space for excellence.

3. Ask questions that make you look junior

I was 24 manuscripting policies with general counsels from top 30 insurance companies. I asked questions that probably annoyed them.

But asking questions when you don't understand builds expertise faster than pretending you do.

4. Own your mistakes immediately

Coverage errors happen. 
Notification delays happen. 
Miscommunications happen.

The brokers who survive own them fast. The ones who spiral try to hide them.

5. Find people ahead of you who will teach

Senior brokers who invested time teaching me line-by-line coverage changed my career. 

Mentorship is earned through showing up prepared and being easy to work with.

6. Physical discipline supports mental performance

I was working until 10 PM and hitting the gym at 4:30 AM. Not despite the long hours - because of them.

You can't sustain high performance on declining physical capacity.
Insurance rewards endurance. 

Build for it.

Nobody told me these rules at 22. 

I learned them through trial, failure, and watching others succeed or burn out.

What unspoken rules have shaped your career?

Building insurance expertise through hard-earned lessons. Follow along.

the unspoken rules of insurance

Most insurance renewals are just photocopies of last year's decisions.
Here's why that's costing financial institutions millions:

An insurance company came to us last year after 12 years with the same broker.

Their coverage had been "renewed" annually.
Premiums negotiated down.
Limits maintained.

Everyone congratulated themselves on another successful cycle.
Then we actually looked at the program.

Their business had completely transformed over those 12 years. 

New product lines. 
Different distribution model. 
Expanded geography. 

Regulatory requirements that didn't exist when the program was designed.

But their coverage?

Still built for who they were in 2012.

We found exclusions that eliminated protection for 40% of their current revenue. Notice provisions that assumed a corporate structure they'd abandoned years ago. Limits that made sense for their old book but left them catastrophically underinsured for their actual exposure.

Twelve years of renewals.
Not one fundamental coverage review.
This wasn't a bad broker.

The standard renewal cycle rewards efficiency over effectiveness. Brokers have 90 days to get signatures. Carriers want minimal changes. Clients want lower premiums. Everyone's incentive is to keep things moving.

Nobody's incentive is to stop and ask: "Does this still fit?"

At LION, we built the opposite approach.

Every renewal starts with a simple question: If we were designing this program from scratch today, what would it look like?

We map current exposures against existing coverage.
We stress-test provisions against actual claim scenarios in your sector.
We compare your program to our manuscript standard built from hundreds of global form reviews.

Only then do we negotiate.

The regional insurer?

We restructured their entire program. 
Eliminated exclusions that would have gutted their next claim. 
Rewrote notice provisions for their actual corporate structure. 

Rebuilt limits around real exposure, not historical habit.

The insurance market rewards brokers who renew fast.

We built LION to reward clients who renew right.

Because coverage that doesn't fit isn't coverage at all.

It's expensive false confidence.

~

Want boardroom intelligence with zero noise?

Every week we share curated insights that cut through the chaos and help you make the best policy decisions.

Join here: https://lnkd.in/garzxSxG

LION Specialty. The Leader in Institutional Insurance. 🦁

We've reviewed every major D&O form in the global market.
Here's why that matters more than any carrier relationship:

Early in my career, I spent six months reading insurance policies line by line with the general counsels who write them.

Not summaries. 
Not broker guides. 
The actual manuscript language that determines whether claims get paid.

That education changed everything about how I evaluate coverage.

Most brokers review forms comparatively. "This carrier's form is better than that carrier's form." Relative judgments based on limited samples.

We review forms against an absolute standard.

Over the past decade, we've built a manuscript benchmark from hundreds of policy reviews across London, Bermuda, and domestic markets. 

Every provision. 
Every exclusion. 
Every definition that matters when claims hit.

When we tell a client "this language is non-standard," we're not guessing. We've seen what standard actually looks like across the entire market.

Last quarter, a specialty insurer brought us their renewal. Their current broker called it "market-leading coverage."

We found eleven provisions that deviated from our manuscript standard. Three of them would have materially impacted their next claim.

One exclusion effectively eliminated coverage for their fastest-growing business line. The broker who placed it had never seen a form without that exclusion, so they assumed it was standard.

It wasn't. We'd seen dozens of forms without it.

The difference between "standard" and "best available" often comes down to how many forms you've actually reviewed.

We've reviewed more than anyone.

That's not a boast. It's a methodology.

Because when you're negotiating coverage, the broker who's seen the most forms knows what's actually possible.

Everyone else is guessing.

Want boardroom intelligence with zero noise?

Every week we share curated insights that cut through the chaos and help you make the best policy decisions.

Join here: https://lnkd.in/garzxSxG
LION Specialty. The Leader in Institutional Insurance. 🦁

People ask how I catch details others miss in insurance policies.
The answer goes back to my mom's design firm:

My mom was the head designer at my parents' company for 35 years. Every project that left their office went through her review.

Line by line. 
Layout by layout. 
Color by color.

She'd check once. Then check again. Then check a third time.

Because if something went out wrong - wrong installation, wrong art, wrong color specification - they paid for it.

Out of pocket. 
Their own company. 
Their own money.

That kind of financial exposure creates a particular kind of obsession with getting it right.

I didn't realize I was learning anything. 

I just saw my mom reviewing projects at the kitchen table, marking up drawings, catching errors before they became expensive mistakes.

But that checking discipline sank in deeper than I knew.

In school, I'd review my work the same way. Once for completion. Again for accuracy. A third time before submission. I became valedictorian not because I was smarter - because I caught what I'd missed.

Now in insurance, that same pattern shows up everywhere.

I check quotes line by line.
Read binders multiple times. 
Review policies until I've seen every provision, every definition, every exclusion.

Not once. 
Multiple times.

Because the details that matter most hide in plain sight. 

You only find them through systematic repetition.

The best disciplines get formed before you know you'll need them.

I learned to check for costly errors in design projects. 

Now I check for coverage gaps in insurance programs.

Different industry. 
Same foundation. 
Same obsession.

Building insurance expertise through systematic discipline. Follow along

Natasha Kiemnec

Most brokers start your renewal 60 days before expiration.
We start 150 days out. Here's why that gap determines everything:

The standard renewal timeline is built for broker efficiency, not client outcomes.

60 days gives you enough time to get quotes, compare pricing, and secure signatures. It's enough time to transact.

It's not enough time to transform.

At 60 days, you're reacting. 

Carriers set the pace. 
Market conditions dictate terms. 
You negotiate around the edges of whatever they offer.

At 150 days, you're shaping the market.

Here's what those extra 90 days actually buy:

Days 150-120: We run a complete exposure audit. 

Not "what did you buy last year" but "what do you actually need today." 

Business changes. 
Risk profiles shift. 
Coverage should evolve with you.

Days 120-90: We stress-test your current program against real scenarios. Regulatory investigations. 
Cyber incidents. 
Coverage disputes we've seen in your sector. 
We identify gaps while there's time to fix them.

Days 90-60: We go to market with a clear mandate. 
Not "renew this program" but "here's exactly what we need and why." Carriers respond differently when brokers demonstrate systematic preparation.

Days 60-30: We negotiate from strength. 

Because we've done the work, we know exactly which provisions matter and which are noise. 

We don't waste leverage on immaterial changes.

Days 30-0: We execute cleanly. 

No surprises. 
No last-minute scrambles. 
Coverage bound with full documentation and implementation protocols.

A regional MGA came to us mid-cycle last year. Their expiration was 45 days out.

We told them the truth: we couldn't do our full process in that window. We could transact their renewal, but we couldn't transform their program.

They waited. Renewed with their current broker for one more year. Came back to us at 150 days.

The program we built was fundamentally different. 
Better limits. 
Fewer exclusions. 
Coverage that actually matched their current business model.

The 60-day timeline would have given them another year of the same.
The 150-day timeline gave them protection that actually works.
Time is the difference between transaction and transformation.

Want boardroom intelligence with zero noise?

Every week we share curated insights that cut through the chaos and help you make the best policy decisions.

Join here: https://lnkd.in/garzxSxG

LION Specialty. The Leader in Institutional Insurance. 🦁

At 22, I was learning from everyone around me.

At 35, I'm teaching what took me 15 years to learn:

At my first Insurance job, I was the youngest person on the team. Everyone else had law degrees or finance masters.

I showed up early. Stayed late. Asked questions that probably annoyed people.

But the senior brokers who took time to teach me? They changed everything.

They'd sit with me line by line through policies. Walk me through carrier 
negotiations. Explain why certain language mattered more than others.

They didn't have to. I wasn't generating revenue yet. I was slowing them down.

But they invested anyway.

By 27, I was building FI teams at JLT. Taking what I'd learned and applying it to bigger accounts, more complex coverage, higher stakes.

The pattern became clear: growth happens through community.

Not just taking knowledge in, but passing it forward.

Now, I'm co-founding LION and mentoring the next generation of insurance pros.

The junior broker who asks questions that slow me down? I remember being her.

The person who needs someone to sit with them through a complicated form? I remember needing that.

The best expertise doesn't stay locked in one person's experience.
It multiplies when you share it.

That's what mentorship actually is - not networking events and coffee chats, but sitting in the details with someone until they understand it the way you do.

Real impact multiplies through others.

Who are you helping grow?

P.S. Ready to accelerate your insurance expertise? DM me - I save spots for committed learners ready to grow.

Your policy has exclusions written in 1987 responding to risks that no longer exist. And new risks with no exclusions at all. Here's why that matters:

I was reviewing a D&O policy for a specialty insurer last month. 

Standard form. 
Top-rated carrier. 
Nothing unusual.

Then I found it.

An exclusion for "computer virus transmission" written in language that clearly predated modern cyber threats. It referenced "magnetic tape" and "diskette transfer."

Nobody uses diskettes anymore. But the exclusion was still there.

Meanwhile, the policy had no clear treatment of AI-related liability. 

Algorithmic decision-making. Automated underwriting errors. The risks keeping their GC up at night.

This is what I call Exclusion Archaeology.

Policy forms accumulate provisions over decades. Carriers add exclusions after bad claims. They rarely remove obsolete ones. The result is coverage shaped by 1990s losses responding to 2025 exposures.

When we review policies, we date every exclusion. Not literally - but we identify which risks each provision was designed to address and whether those risks still exist in that form.

Then we map current exposures against exclusionary language.

The gaps are always surprising.

That specialty insurer had robust protection against risks from the floppy disk era. They had almost nothing addressing how their AI pricing model might create liability.

Their broker had negotiated hard on premium. Nobody had questioned whether the exclusions matched modern reality.

We rewrote their program. Removed three obsolete exclusions. Added specific coverage grants for their actual technology stack. Negotiated AI liability treatment that their old form didn't contemplate.

The insurance market builds policies through accumulation, not design.
Elite coverage requires excavating what's actually in there - and rebuilding for current reality.

Want boardroom intelligence with zero noise?

Every week we share curated insights that cut through the chaos and help you make the best policy decisions.

Join here: https://lnkd.in/garzxSxG

LION Specialty. The Leader in Institutional Insurance. 🦁

In 2023 I got my Pilates instructor certification. 

Here are 3 lessons from 450 hours of training:

1. Physical practice improves mental performance

Morning movement clears decision fog. Body awareness enhances presence. 

Breath work calms market stress. Energy management beats time management.

2. Teaching others deepens personal mastery

Breaking down complex moves mirrors explaining coverage. Student progress reveals leadership insights. 

Different learning styles need different approaches. Small adjustments create major improvements.

3. Consistent practice compounds results

Daily habits matter more than occasional effort. Precision beats intensity. 

Balance prevents burnout. Sustainable progress outperforms sprints.

The insurance executive who became a Pilates instructor?

She didn't leave her career. 

Balance drives sustained growth. Discipline creates freedom. Movement enhances clarity. Integration beats separation.

At LION, we do more than talk about work-life balance.

We build it into our culture. Midday workouts. Diverse interests. Clear standards with room to grow past them.

Because people who only do insurance will eventually do insurance poorly.

Your competitive edge isn't sacrificing everything for one goal.

It's building a life where different pursuits strengthen each other.

How do you integrate your passions with your profession?

♻️ Repost to inspire holistic leadership.

Underwriters stopped asking if your vault is locked.
Now, they're asking if your robot employees have a human babysitter...

CFOs, CISOs, and risk managers at financial institutions:

Last Thursday's Anthropic disclosure fundamentally changed how we think about cyber risk.

And more importantly, what you need to do about it before renewal.

Chinese state actors convinced Claude it was a security professional conducting authorized testing.

Then gave it the capability to touch real systems autonomously.

The result: 30 simultaneous attacks across tech giants, banks, and federal agencies.

80-90% automated. 
Machine speed. 
Thousands of operations per second.

We've spent the week digesting Anthropic's forensic report, talking with our carrier counterparties, and fielding calls from clients who thought their AI governance covered this.

Most governance policies address employees using ChatGPT inappropriately.

They never contemplated ChatGPT becoming the criminal.

Most policies are silent on AI. And silence means potential denial when your AI hallucinates and destroys critical data.

The market split into three camps: broad AI exclusions, $1-5M sublimits, or premium surcharges.

Your renewal timeline just accelerated by six months.

If you want the breakdown of what sophisticated institutions are implementing right now (hardware keys, explicit AI coverage language, human-in-the-loop documentation)…

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

Comment "BRIEF" below if you're not on our distribution…

"You're not spending summers at home."
That one parenting decision shaped how I see risk:

Starting at age 5, my parents had a rule: summers were for experiencing the world.

Eight to ten weeks at camp. French language immersion. Study abroad programs before most kids left the state.

At 14, I was hiking Machu Picchu. At 15, I was living on a boat in the Caribbean.

By college, I'd done three study abroads. Not because I was running from home - because I was learning to see the world through different lenses.

My parents understood something most don't:
Your perspective determines how you assess risk.

If you only see the world from one vantage point, you miss threats others see clearly. You misread opportunities that are obvious to people with different experience.

A white American girl from the middle of the country has blind spots. The only way to address them is exposure.

That early travel completely changed how I approach insurance.

Risk isn't just domestic. Financial institutions operate globally. Markets shift based on international dynamics. Coverage needs change based on regulatory environments across jurisdictions.

If I'd only understood risk from a US perspective, I'd miss half of what matters.

Now at LION, we're building with that same philosophy - global perspective, international footprint, understanding risk across markets and jurisdictions.
The best risk assessment comes from people who've seen problems from multiple angles.

Early exposure shapes how you see everything that follows.

What experiences shaped how you assess risk?

Building insurance expertise through global perspective. Follow along.

Insurance language shouldn't require a law degree to understand.

So we broke down stuffy 50-page industry forms into a simple ~30 page manuscript:

"If you can't explain it simply, you don't understand it well enough."
Most FI policies run 50+ pages of dense technical jargon.

Contradictory endorsements. Nested definitions that reference other definitions. Exclusions buried in subsection C of clause 7.

We created a manuscript that's only 35 pages.

Clear language. 
Logical structure. 
Comprehensive coverage.

Here's why this matters for financial institutions:

Complex language creates coverage gaps in D&O and E&O policies.

Technical jargon breeds misunderstanding of critical exclusions. Confusion leads to claim disputes when you need coverage most.

The institutions that succeed? They demand clarity in their coverage documents.

What Actually Works:

Plain language explanations eliminate ambiguity. Logical coverage organization shows how provisions connect. Consistent terminology prevents contradictory interpretations.

Visual policy mapping reveals gaps before claims hit.

Common Mistakes:

Accepting industry standard forms without question. Ignoring contradictory endorsements layered over years. Missing coverage connections between related policies.

Skipping documentation review until claims arrive.

Your Coverage Blueprint:

Set the foundation by demanding clear policy language and requesting visual coverage maps. Eliminate redundant provisions that create confusion.
Consolidate related coverages into coherent structure.

Create the strategy by building comprehensive glossaries everyone can reference.

Document coverage intentions during placement, not after denials. 

Establish review protocols that catch gaps early. Test programs with claim scenarios before real losses hit.

Clarity creates confidence. 

Simplicity serves everyone. 

Understanding prevents disputes. 

Documentation determines outcomes.

What's your coverage clarity strategy?

~

P.S. Want to see what elite policy documentation looks like?

Book a live policy review: https://lnkd.in/g9rJT-ka

LION Specialty. The leader in institutional insurance.

We've recovered $250M+ in claims because our strategy starts before losses happen.
Here's the exact 10-step process:

1. Choose carriers who act like partners

The right carrier views claims as promises to keep. 

The wrong one views them as problems to minimize. That choice gets made at placement, not during crisis.

2. Get crystal-clear policy wording upfront

Ambiguous language doesn't protect you better - it creates disputes you'll fight later. 

We negotiate precise definitions and explicit coverage grants before you ever need them.

3. Run mock claim scenarios before you need them

If your coverage doesn't work in simulation, it won't work in crisis. 

We stress-test programs against real loss patterns. 
Ransomware during peak operations. 
SEC investigations. 
Nuclear verdicts.

4. Deploy specialist expertise, not generalists

Complex claims don't need good brokers. They need specialists who've seen your exact scenario before. 

Forensics experts. 
Coverage counsel. 
Crisis consultants who understand FI exposures.

5. Balance assertive advocacy with strategic compromise

Push too hard, damage carrier relationships. Accept too quickly, leave millions on the table. 

Elite advocacy requires knowing when to escalate and when to negotiate.

6. Prevent disputes before they start

Most denials trace back to notification errors, not coverage gaps. 

Establish protocols during placement that eliminate procedural mistakes before they cost you.

7. Use data to drive every decision

Claim outcomes follow patterns. 

We analyze settlement histories, trigger data, and industry benchmarks to build positions carriers can't dismiss.

8. Keep pace with regulatory evolution

Regulatory changes shift coverage implications constantly. 
Track developments that affect your exposures. 
Adjust programs before gaps emerge.

9. Document everything - gaps in paperwork create gaps in recovery

Carriers deny more claims for missing documentation than actual coverage disputes. 

Build documentation protocols that withstand scrutiny from day one.

10. Be the steady hand through the storm

Claims create chaos. Leadership needs structure, process, and calm execution - not brokers who panic alongside them.

Many financial institutions leave millions on the table when claims hit.

You don't have to be one of them.

Want boardroom intelligence with zero noise?

Every week we share curated insights that cut through the chaos and help you make the best policy decisions.

Join here: https://lnkd.in/garzxSxG

LION Specialty. 

The Leader in Institutional Insurance.

Legally, drones are aircraft.
That one fact nearly created millions in uninsured exposure:

I was reviewing a policy with an insurance company that uses drones for claims adjusting.

Standard manuscript session. Walking through exclusions. Making sure everything aligned with their operations.

We hit the aircraft and operational machinery exclusion.

The CFO stopped me.

"Wait. A drone is technically an aircraft. If this exclusion stays as written, we have a problem."

He was right.

They were using drones daily to assess property damage, inspect hard-to-reach areas, expedite claims settlements. Core business operations. Revenue-generating activity.

And their policy would have denied every claim related to it.

Most brokers would have kept moving. "It's a standard exclusion. Every policy has it. No one's going to challenge drone use."

But standard exclusions don't care about your intentions. They care about their language.

If the exclusion says "aircraft" and drones legally qualify as aircraft, you're denied. 

The carrier won't make exceptions during a claim just because you didn't think it applied.

We added a carve-back.

One sentence: "This exclusion does not apply to the use of unmanned aircraft for claims handling, adjusting, and loss assessment."

That carve-back protected millions in potential exposure.

The exclusion still served its purpose - no coverage for operating commercial airlines or traditional aircraft. But their actual business operations? Fully covered.

This is why custom manuscripts matter.

Standard forms get written for hypothetical companies. 

Broad language. 
One-size-fits-all exclusions. 
No consideration for how you actually operate.

Custom forms get written for your business. Your operations. Your risk profile.

One client conversation caught what could have been years of uninsured exposure.

How many gaps exist in your policy because no one asked the right questions?

~

Ready to stress-test your coverage?

Book a live policy review: https://lnkd.in/g9rJT-ka

We typically find gaps standard reviews miss.

LION Specialty. 

The Leader in Institutional Insurance.

Most brokers build carrier relationships through entertainment budgets. We built ours by making underwriters better at their jobs. Here's what that actually looks like:

Early in my career at JLT, we made a strategic decision. Instead of competing through access and happy hours, we'd compete through education.

We started writing technical papers. 50-100 pages on D&O coverage evolution. 

Policy language analysis. 
Case law trends. 
The history of financial institution professional liability.

Deep work. The kind that takes weeks to research and write.

Then we gave it away.

Carriers used our papers to train junior underwriters. They included our analysis in their own publications. They cited our work in coverage position papers.

We created "Day in the Life" sessions - immersive programs showing underwriters how elite brokers actually review policies. 

What we look for. 
Why we ask the coverage questions we ask. 
How we stress-test programs before placement.

Half-day versions with presentations. 
Full-day versions in New York with multiple speakers. 
Premium programs running multiple days with networking built in.

We co-authored quarterly publications with carrier partners. Not promotional material. Actual technical content that served the broader market.

The result was deeper than access.

Carriers preferred working with us because we understood their products at a technical level most brokers never reach.

When we negotiated coverage, both sides operated from shared expertise instead of adversarial positioning. Conversations became collaborative instead of confrontational.

That foundation transferred directly to LION.

We don't build relationships through golf outings. We build them through systematic expertise that elevates everyone we work with.

When you make your partners better at what they do, they choose to work with you. When you invest in shared understanding, negotiations shift from conflict to collaboration.

The insurance market rewards brokers who entertain.
But it remembers brokers who educate.

~

Want boardroom intelligence with zero noise?

Every week we share curated insights that cut through the chaos and help you make the best policy decisions.

Join here: https://lnkd.in/garzxSxG

LION Specialty. 

The Leader in Institutional Insurance. 🦁

"Should we notify our insurance carrier?"
Simple question. Complicated answer. Here's what I mean:

A specialty insurer called us for a second opinion during a regulatory examination. 

The State department of insurance was asking questions.

Nothing adversarial yet.

Their policy had a "claims-made" trigger. Coverage applied to claims first made during the policy period. But "claim" was defined to include "any written demand for monetary or non-monetary relief."

Was a regulatory information request a "demand"? 

Did examination questions constitute "relief" being sought?

Their previous broker said to wait. "It's not a claim yet. Don't notify until there's an actual allegation."

In this case, we disagreed.

We'd seen this exact scenario three times before. 

Twice, carriers argued late notice when examinations escalated to enforcement. 

The clients who notified early preserved coverage. The client who waited lost it.

"Claims-made" sounds simple. But "claim" definitions vary wildly. 

Some include investigations. Some don't. 

Some require formal allegations. Some trigger on informal inquiries.

At LION, we run trigger scenarios during placement.

We ask: "If this happens, does it trigger coverage?" 
Then we test the language against our answer.

Regulatory inquiry. 
Internal investigation. 
Informal complaint. 
Demand letter. 
Formal lawsuit.

Each scenario. Each policy. Every time.

The specialty insurer notified immediately. 
Six months later, the examination became an enforcement action. 
Coverage was preserved because they'd triggered it early.

Their former broker's advice would have cost them the claim.

~

Ready to stress-test your program?

Book a live policy review: https://lnkd.in/g9rJT-ka

27 new reciprocals launched to fill capacity gaps in catastrophe zones... 

NY DFS just collected $19M from 8 insurers for basic cyber failures... 

And Financial Lines underwriters evaluate reciprocals through a completely different lens than you'd expect.

In this week's Friday Five, we're tracking how reciprocals are solving the homeowners coverage crisis in hurricane-exposed markets.

We break down how 18 reciprocals launched in just the past year - bringing $51 billion in premium capacity to markets traditional carriers exited.

Plus, DFS collected penalties for hackers stealing driver's license numbers through online quote tools. 

Hartford paid $3M, Liberty Mutual $2.7M, Farmers $2.775M. 

The crazy part? DFS warned about these exact vulnerabilities back in February 2021.

And how Financial Lines underwriters actually evaluate reciprocals: they see two distinct entities with separate exposures. 

The Exchange holds risk. The Attorney-in-Fact manages operations. Each requires different coverage.

New here? 

Every Friday we distill 200+ insurance, legal, and market-risk articles into three signals your board may need for its Monday briefing...

Want the full analysis this week? 

Comment 'brief' below and we'll get you on the distribution. 

Stay covered everybody.

Financial institutions are the most complex risks in the insurance market.
So why do most brokers assign them to generalists?

I've spent my entire career in financial institution coverage. D&O. E&O. Cyber. Fiduciary. 

The specialized lines that protect organizations when sophisticated risks materialize.

Here's what I've learned: 

Generalist brokers can place these policies. They cannot optimize them.

The difference shows up in details that only matter during claims.

Last year, we reviewed a program placed by a top-10 global broker for a regional insurer. 

Solid carrier. 
Reasonable pricing. 
Professional execution.

But the broker who placed it had never handled a bank regulatory claim.

The notice provisions required immediate notification to the carrier upon "receipt of any regulatory inquiry."

Sounds reasonable. 

Except banks receive routine regulatory inquiries constantly. 

Compliance examinations. 
Information requests. 
Supervisory letters.

If they'd notified on every one, the carrier would have non-renewed them for claims frequency. If they'd filtered and missed one that escalated, the carrier could deny for late notice.

The provision created a trap with no good option.

A specialist would have caught it. We've negotiated that exact language hundreds of times. We know which formulations work and which create impossible compliance burdens.

A generalist saw "notification requirement" and moved on.
That's the specialist paradox.

Generalists can execute the transaction. But the details that determine claim outcomes require pattern recognition that only comes from deep specialization.

At LION, we only serve financial institutions. Not because we couldn't do other things. 

Because focus creates expertise that breadth never matches.

Every provision we negotiate reflects hundreds of similar negotiations. 

Every scenario we stress-test draws from claims we've actually handled. 

Every recommendation builds on patterns we've seen across the sector.

When you're buying complex coverage, the question isn't whether your broker can place it.

It's whether they've seen enough to know what actually matters.

Want boardroom intelligence with zero noise?

Every week we share curated insights that cut through the chaos and help you make the best policy decisions.

Join here: https://lnkd.in/garzxSxG

LION Specialty. The Leader in Institutional Insurance. 🦁

Pilates trains you to sense what's wrong before it becomes obvious.
I use that exact skill every time I review coverage:

Every Tuesday at 6 AM, I'm in Pilates learning to feel imbalances before they become injuries.

A hip that's slightly off becomes back pain six months later. 

A weak stabilizer muscle becomes a torn rotator cuff. 
Your body compensates until it can't.
Pilates teaches you to notice the compensation before the failure.

That awareness translates directly to insurance.

Most brokers review policies like checking boxes. 

Does it have D&O? Check. 
E&O? Check. 
Reasonable limits? Check.

But coverage gaps don't announce themselves.

They hide in the space between sections. 

In allocation language that looks standard but shifts millions during claims. 

In exclusions with carve-backs that don't quite cover what they should.

Pilates trained me to sense tension before I can articulate why it's there.

I'll read a definition that's almost right but subtly wrong. An exclusion that sits awkwardly next to a coverage grant. Provisions that technically work but create friction under stress.

Things I would have missed at normal speed become obvious when I've trained myself to feel imbalances.

It's not magic.

The same way I slow down in Pilates to notice which muscles are compensating, I slow down in policy review to notice which provisions are creating unintended gaps.

Most people think faster is better.

But the best work happens when you slow down enough to sense what's off.
Physical practice sharpens mental awareness. 

The focus required to hold proper form trains the focus required to catch subtle language.

Different disciplines cross-train your brain.

Building insurance expertise through deliberate practice. Follow along.

LION Specialty

As CEO, co-founder and managing partner at LION Specialty, I lead a high performance team that specializes in advisory and placement of risk & exposures for financial institutions and private equity firms. 

The global insurance marketplace is constantly evolving. In order to remain relevant, you must have your finger on the pulse.

With decades of experience working for major insurance brokers, and building businesses, we leverage AI, data & advanced analytic tools to provide accurate market information about pricing fluctuations, legal and regulatory impact, and carrier capacity / appetite. 

LION Specialty partners with insurance companies, banks, investment managers, and private equity firms. We provide access to the right resources and information in order to best position these clients in the global commercial insurance markets. 

Our team is comprised of high-performing credentialed professionals who are trained to elevate our clients. 

When clients work with LION Specialty, they can expect: 

• A seasoned team of specialists that understands their risks and exposures 
• Access to some of the best strategic relationships with carriers and underwriters in the global market
• Market leading tools such as credible data/benchmarking, advanced anlytics and loss modeling 
• Weekly newsletter with up to date market conditions (pricing, appetite and capacity) and legal regulatory, and claims trends impacting the markets
• Exceptional day-to-day service

Better access to important resources that will better position their business among other brokers.

Our mission is to trade with integrity in global markets, elevate community standards, and consistently refine our processes for peak performance.

With over 85,000 hours in the industry, I understand firsthand the importance of team collaboration.

I’m passionate about hitting the field daily, embracing the grind and process alongside a dedicated team.

To learn more about LION Specialty, please send me a message.

Chief Executive Officer | Managing Partner and Co-Founder 

Managing Director

Marsh

*Sales leader for the New York Metro FINPRO Operations of Marsh, specializing in the sales of management and professional liability lines for Global Risk Management (Fortune 1000 clients) and National Brokerage (Forbes 500 & Middle Market) clients. 10/10 - 8/13
*In charge of the sales force and the growth of the North and South Carolina operations of Marsh. Charlotte Executive Leadership team. 8/13 - 10/14
*Client Executive - Financial Institutions Practice 10/14 - 4/15

NY Metro Sales Leader

Wells Fargo Insurance Services

*Greater New York Area
*Northeast Professional Risk Group Production Team 
*Specialty broker of professional liability insurance for public and private companies, financial institutions and law firms

Willis

*Based in New York City
*National Executive Risks Practice Group 
*Specialty Broker of directors & officers liability, errors and omissions, employment practices liability, fiduciary, and fidelity insurance
*Clients included public and private companies and financial institutions

Sentry Insurance

*Based in Denver, Colorado 
*Sentry's Commercial Lines Direct Sales Program
*Producer responsible for sales of commercial general liability insurance

Associate

Midwest National Life Insurance Company (AFS)

*Based in Denver, Colorado
*Captive Agent responsible for sales of Midwest National's employee benefits programs (2001- 2003)
*Underwriter of Midwest National's preferred provider organization / health insurance program for individuals and small businesses (2000-2001)
*Started as Intern in 2000

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

I spent 20 years inside the machine.

And when I finally left, it took me six months just to learn how to breathe again.

I had been doing what the machine required: 

Grinding.

Wearing "exhaustion" like a badge of honor.

It was disgusting. 

And massively unhealthy.

So when we started LION, I went looking for a different map.

During my sabbatical I was devouring Ryan Holiday books.

I started reading my Bible again. 

Then a friend recommended this cookbook.

“The Blue Zone Kitchens” 

It changed my life.

I had seen the 60 Minutes.

But I went deep. 

I learned about places like Okinawa, Sardinia, and Loma Linda, California, where longevity comes from systems, not just genetics.

Then my ADD curiosity…

"What if we built a brokerage using Blue Zone rules?"

Woo, woo - maybe! 

But the results…

1. Connection: NO lone wolves. LIONS! We work as a Pride.

2. Purpose: “talent, compensation, and culture,” all aligned around the mission…

3. Wellness / Recovery: we go hard still, but in moderation…and we treat rest as a performance drug.

And more! 

We are building the industry's first "Corporate Blue Zone."

A place where high performance doesn't require normalizing anxiety.

A place where you can build a legacy without destroying your life.

Wellness is an expectation! 

I was lost in the grind for two decades.

Now we are charting a new path.
We are inviting you to join the Pride.

What’s your favorite Blue Zone? 

Japan, Greece, Italy, USA, Costa Rica, Singapore?

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

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A mentor asked me: "Do you want to be good at everything or elite at one thing?" 

Been chasing the latter since 2004. 

He’s walking me through what it takes to reach the top of the insurance world.

( He’d been there since the 80s ) 

He says: "You have to specialize…

You can specialize in a product - D&O, E&O, Cyber. 

Or you can specialize in an industry - financial institutions, healthcare, tech…

But you have to pick one."

I'd been a generalist up to that point. 

Covering small businesses, multiple industries, whatever we could get. 

That approach works. 

But it has a ceiling.

Generalists compete on service and  price.

Specialists compete on expertise.

When you're a generalist, clients evaluate you based on how responsive you are and how competitive your premium is. 

You're replaceable.

When you're a specialist, clients evaluate you based on what you know that others don't. 

You're essential.

You become part of their team. 

Joe told me if I wanted to specialize at the highest level, I needed to go where specialization was built. 

New York or London. 

Places where you could focus entirely on one industry and work with the best clients, the best underwriters, the best lawyers.

So I zeroed in on financial institutions.

It wasn't random. 

I liked the complexity. 

I liked that FI risk was different from every other industry.

And when I got to New York in 2005, I got thrown onto one of the industry’s leading FI teams.

That decision - to specialize - shaped everything after.

Twenty years later, I don't cover anything outside financial institutions. 

Not because I can't. 

Because depth beats breadth.

When a bank CFO… or an insurance company CEO…has a D&O question, they don't want a generalist who "also does financial institutions."

They want someone who knows every major FI form in the market. 

Who's seen every type of FI claim. 

Who understands regulatory trends before they hit.

At LION Specialty, we only cover financial institutions.

We're not trying to be good at everything. 

We're trying to be elite at one thing.

That focus lets us go deeper than generalists can afford to. 

It lets us build expertise that compounds year after year.

And it lets our clients work with a team that knows their world better than anyone else in the market.

The conversation that shaped my career happened in 2004.

The choice I made then still defines what we do today.

What conversations have helped define your career? 

Follow along at Mark Flippen for more daily insurance insights! 

P.S. two of my new favorite midtown “specialty coffee” shops in NYC - Devocion and Black Fox

I learned service on the 4/5 train.

Busy executives valued this even more than experience, I discovered back in 2006.

I was just a rookie broker working on the smallest financial services accounts, but I found a way to make the senior partners need me...

At the time, I was the most junior person on the team. 
Putting together presentations.
Just trying to add value.

Every morning on the subway, I would read the Wall Street Journal. 
Sometimes the Financial Times. And the Bloomberg magazines.

I just wanted to have something to talk to my underwriters about.

I started sending summaries around to the team. Then, I watched as some of the best producers in the firm took my notes and sent them directly to clients.

They would add a simple note:

"In case you missed this article in the Journal this morning, I thought you’d be interested. Here is a summary for your convenience."

Clients loved it.
Especially the big bank risk managers.
And the buy-side insurance company executives.

Because people are busy.
No one catches everything they should read.

Long before "content marketing" became a buzzword, the best strategy was just being useful.

That spirit is the DNA of the LION Specialty "Boardroom Briefings."

We still do the heavy lifting for you.

Every week, our team scans 200+ insurance, risk, and legal articles.

We pick the top three that actually matter. And on Fridays, I write an editorial telling you why they matter.

Join 2,000+ financial executives who start their weekend prepared.

Subscribe to the Briefing:
(Link in bio) 

P.S. does anyone still read the paper Journal? 

Might start getting it sent to the house again. I miss the feel of it w my morning coffee!

When you start the week driving across Alligator Alley on Monday redlining a VW Jetta…

Then you’re sitting in a Chicago steakhouse the next night…

NYC brunch the next.

Then the Dale a few days later.

You know stuff is happening.

The past couple of weeks, we’ve been in rooms with some of the coolest cats in the insurance industry.

Like a big shot in the arm reminder of how much of a PEOPLE business this still is!

Forget the tech convo.
Forget about all the automation.
The soulless zoom calls.

There’s nothing better than getting in front of clients…

Chopping it up across tables.

Then breaking some bread over lunch or dinner.

Soaking up all the unique perspectives…

And blessed to call a bunch of these teams new LION Specialty clients!

- A new Reciprocal client: 

Incredible energy. They're building from scratch but on a time-tested, member-aligned model. Their sense of mission is palpable!

- A 60+ yr old Midwest broker client: 

Salt of the earth leadership team. All on the same page. You sit with them for five minutes, and you just feel the culture they’ve built. The kind of team you'd buy from yourself.

- An insurtech client: 

Their GTM plan is one of the most well-thought-out plans I’ve seen, maybe ever. They are relentlessly questioning "the way it's always been done" and building new solutions from the ground up. The speed these guys are moving is crazy.

- A startup MGA prospect: 

The definition of diligence. Meticulously building a rock-solid case for their Lloyd's coverholder application. The kind of firm helping US risks find Lloyds capacity. Very bullish on Lloyd’s right now!

- A global MGA client: 

A masterclass in balancing priorities - navigating complex capacity, international scale, and underwriting discipline, all at once.

Sitting in these different rooms, you see the whole picture.

The shared challenges (talent, tech, new risks) and the unique pressures each one faces.

This is what "tee-ing up" our work is all about.

To truly advise these clients (whether it's on their D&O, E&O, or Cyber risks) you have to understand the parts of our world they operate in.

The strategies happening in these boardrooms?

Unlike anything I’ve seen in my 25 years in the business.

P.S. if you’re a similar type of insurance operation and you want to chat about our team’s capabilities, let's connect!

20 years ago in my first broker job, I got to see what the best clients have in common.

Their deal size didn’t matter.
It wasn’t necessarily their industry.

It was their standard.

Willis. Executive risk team. 

I’m 27 and surrounded by clients who’ve been building businesses for decades.

I was on a high performance team that serviced high performance teams. 

The way they prepared for meetings. 

The precision of their questions. 

The discipline in how they approached risk. 

They didn’t accept surface-level answers or generic solutions.

They knew something that was amazing to see so early in my career.

When everyone on their team - including their brokers - operates at an elite level, they get better outcomes.

Better insurance. 

Better risk strategies. 

Better protection for what they’d built.

These clients understood that your peer group determines your trajectory.

That includes the advisors you choose.

When you surround yourself with A-players - in your company, on your board, in your service providers - you don’t just get better service. 

You accelerate your own growth.

Excellence compounds when everyone at the table refuses to settle.

When we built LION, we built it for clients like this.

High-performers who see their insurance broker as an extension of their team. 

Who know that the right partners don’t just deliver - they elevate.

Your team sets the standard for your entire business.

Choose partners who make you better.

P.S. Julie snapped this photo on my first day at Willis in 2005, when we still wore suits and ties everyday!

My secret travel weapon.

This little work of art has traveled 1,000,000+ miles with me...

...and it is probably the best $30 investment I’ve ever made.

Low tech. 
You just need hot water. 
Isn't expensive.
The Aeropress!  

Shout out to my friends at AeroPress, Inc. 

I’m in London this next week, and while the coffee is good, if you stay in the espresso lanes - finding American “drip,” coffee is nearly impossible! 

Except for my favorite coffee shop in Mayfair:  “Kaffeine”

Best American drip coffee in the UK. 

For the coffee snobs out there, you know the pain of hotel coffee. 

Or if you get up ridiculously early like I do, the coffee shops aren’t even open yet! 

It is a gamble I stopped taking years ago.

This simple gadget is:
• Indestructible 
(it lives in my carry-on)
• Consistent 
(perfect coffee, every time)
• Cheap 
(the ROI is infinite)

I see people chasing Black Friday deals on $300 gadgets they will use twice.

Do yourself a favor. 

Spend $30 on this puppy.

Your mornings on the road will thank you.

What is the one thing you never travel without?

Mental toughness in insurance.
Sounds ridiculous. We’re not Navy SEALs or ultra-marathoners.

But the most successful entrepreneur in my orbit would disagree.

He sold his operation a few years ago. 

For ten figures.

We were fortunate to get to handle their corporate insurance for a few years. 

And get a peak on the inside.

These guys were the real deal. 

Immediately after the sale, one of the big (re)insurance media outlets interviewed them about the roots of their success.

First thing mentioned? 

It wasn’t about any one guy. 

The founder’s last name was absent from the company name. It wasn’t on the door. 

It was Team-based from day one.
Their best ten against yours. 
We’ll see y’all in the arena kinda culture. 

Second thing…

“From the start, the Team we assembled could compete with any of the big brokers.”

And they did. 

Right out of the gate, they went toe-to-toe with the giants.

They were obsessed with it. 
And won a ton. 

At LION, we’ve built the same way. 

Imitation? Nope. Emulation. 

Financial services companies choose us for a lot of reasons already. 

Yet here’s the real one IMO: 

We can compete with the biggest brokers in the business. 

And we have been since day one.

Most people call what we’re doing “delusional.”

They might be right.

Here’s what they miss…that delusional belief isn’t blind optimism.

It’s mental toughness. 

It’s part of the foundation and…how the team executes and wins when everyone - clients, competitors, trading partners, even people in our own orbit - think we’re a ‘bit crazy’ for even trying.

That’s why I obsess over it.

P.S. 

If you’re a broker in the business and you like this post, you might be a LION! 

If you buy insurance for your financial services company, and you like this kind of mentality in your broker team - you need a LION on your team!

The most dangerous insurtech mistake.

Checking the box works at Seed, but at Series A it becomes a multi million dollar land mine. 

When our team started working with the CFO of a transportation Insurtech…

They were raising their Series A. First serious round of capital. 

They had coverage they bought as a startup.

"check the box cover"

But they had way outgrown it. They were closing in on $100 million in premium and shoring a bunch of the "early days get it done" ops stuff up. 

Here's the land mine: 

They had one policy for their Tech E&O. And a second policy, from a second carrier, for their MGA E&O.

This is the classic "two-carrier trap."

What happens when they screw something up and get sued?  

The tech E&O insurer says it was an operational error. 
The MGA E&O insurer says it was the faulty code.

Both quasi deny the claim.

You, the client, are left in the middle, paying for a legal battle between your own insurance companies...while also fighting the customer who is suing you.

Specialized risk isn't a commodity.

For a modern MGA, your technology is your operation.

Your risk is singular.

Your coverage must be, too.

We fixed it by placing them on a single, unified form with one carrier. No gaps, no finger-pointing.

Your broker's job isn't to sell you two policies. 

It's to give you one solution.

after reading this morning’s devotional w Coach Dungy I realized: 

I’m in the process of unlearning a professional lifetime built on  "performance" 

to learn the simple act of submitting to God’s "grace"

in corporate America, we are defined by our position and measured on our successes

even if that’s not exactly correct, it felt that way to me

I left at the end of 2022

had achieved nearly as much of that success as one could

then I walked away from it all 

at the time for selfish reasons 

it wasn’t for some higher calling 

since then, I’ve spent the last three years trying to unlearn many of the bad habits built by an identity based on performance

I'm trying to replace it now with one based on grace

it seems so easy

it’s massively difficult

the difference between "you are what you do" and "you are loved, period” 

my humble dependence this Sunday is on that grace

it’s the whole story

“salvation is by grace alone, never earned by your works or success, but received by faith”
Ephesians 2:8–9

Much love and Happy Sunday, y’all !

graphical user interface, text, application, chat or text message

Last Sunday at my Church we honored our Veterans by asking them all to stand. The place broke out into a thunderous round of applause. Exactly how it should be. These women and men and their families have given everything so we can have the freedom to do what we do. They deserve WAY more than these simple acts of our courtesy, though. They deserve to be applauded everywhere they go, IMO. They also deserve these five words from all of us too: “thank you for your service!” Madam. Sir. I grew up in an era when we all pledged allegiance to the flag. It was an honor to back then and it is an absolute honor now. Our service members are real life heroes to me. To all who have served our country, and all who are serving now, I thank you and your families. Happy Veterans Day. 

God Bless America!

The challenge facing every insurance carrier that writes cyber isn't if this will happen—the near-misses are already happening. The question is whether their balance sheet, capital structure, and reinsurance treaties are built to survive an event that operates outside every historical precedent the industry has ever relied upon.

View newsletter: LION Specialty Newsletter 

In 2017, the NotPetya ransomware attack caused an estimated $10 billion in global damages. It was a digital shockwave. It hit shipping giant Maersk ($

Open article: How a "Cyber Hurricane" Breaks the Insurance Model in 24 Hours by Mark Flippen • 5 min read

How a "Cyber Hurricane" Breaks the Insurance Model in 24 Hours

Your marketing team's new AI press release could cost you $56 million.

Here’s how to make sure your corporate insurance is designed to respond.

"AI Washing" - exaggerating  AI capabilities - is no longer a marketing buzzword. 

It’s a peril. 

Regulators are treating this exposure like old-fashioned fraud.

And the litigation is exploding. 

Securities class action lawsuits tied to AI doubled last year and are on pace to break another record in 2025. 

This wave is moving faster than crypto or COVID-19 claims.

And the financial impact is clear. 

The average settlement for these claims in the first half of 2025 spiked to $56 million.

Making it now definitively a board-level disclosure risk, not an IT risk. 

D&O carriers are on high alert, too. 

They’re reacting with:

- Comprehensive underwriting of all public AI statements 
- Targeted premium hikes for any company marketing AI in a sensational manner. (E.g. press releases w “game changing,” or “revolutionizing,” even “reshaping the industry.”) 
- New exclusions for "misrepresentation" of AI capabilities

Don’t let the current soft market conditions fool you either. 

For company’s doing anything w AI, your D&O renewal is no longer a simple transaction; it's a reputational audit of your AI strategy.

Before your next earnings call, you should audit all public-facing AI statements. 

My team helps clients build a defensible narrative that proves to underwriters you’re a best-in-class risk.

Let’s us know if you need help thinking through this new exposure! 

We’ve recently helped several MGAs, and Insurtechs heavy into AI recently market their own insurance programs successfully!  

_______________________

Hello, I’m Mark Flippen. For 20+ years, I’ve structured insurance strategies for financial institutions and private equity firms.

Want boardroom-ready risk intelligence? Join 2,000+ executives subscribed to our Boardroom Briefings.

Weekly insights on claims trends, regulatory shifts, and global insurance markets - written specifically for financial services leaders.

Link in bio or DM me.

LION Specialty  
The Leader in Institutional Insurance.

This is not imposter syndrome:

You have negotiated billion-dollar treaties, but you can't tell if you are covered because the system is designed to confuse you.

You’re General Counsel of a fast-growing MGA.

Top law school. 

15 years in insurance.

It is 11 PM. You are on page 184 of your E&O policy. Trying to figure out if your binding authority activities are actually covered.

The exclusions are buried. 

The sublimits are unclear. 

It is a mess.

You start questioning your own competence.

I should know this.

No. You shouldn't.

Financial institution executives shouldn't need insurance coverage PhDs to know if they are protected.

By their own policies. 

We’ve worked with brilliant CFOs and GCs at MGAs and Mutuals who blame themselves for this.

Here is the reality though…

The system isn't broken.

It is designed this way.

Policy complexity doesn’t protect clients.

It sets up the argument, the posture, the reservation of rights letter when you get a claim. 

It’s avoidable, though. 

Swipe through to see how we translate complexity into clarity for our financial institution clients  →

Translating Insurance Complexity  

Here's what nobody in insurance is talking about...

your biggest cyber risk lives in your portfolio.

In this week's Wednesday Intelligence edition of the LION Specialty Boardroom Briefings, we're having an unfiltered conversation about systemic cyber risk. 

The correlated exposure you're getting paid to underwrite.

The one that dwarfs the operational risk inside your own network.

We break down the difference between the "Victim" mindset (spending millions to protect your own fortress).

And the "Aggregator" reality (you're underwriting one risk 10,000 times, all in the same location: the internet).

Think about it this way: 

When you write 10,000 homeowner policies, a fire in Ohio doesn't cause a fire in Texas. 

But when you write 10,000 cyber policies, they all may be exposed to the same single vulnerability in core software.

Every carrier is focused on preventing the $50M operational loss from their own breach while completely overlooking the potential $500M underwriting loss from their portfolio.

The most sophisticated carriers are now addressing a pattern the entire industry missed while everyone focused on the same playbook.

New here? 

Our Wednesday Intelligence editions provide the claims prep and strategic intelligence you need to protect your institution...

Want the full unfiltered conversation? 

Comment 'brief' below and we'll get you on the distribution. 

Stay covered out there everybody! 

—————

P.S. Next week's Part Two reveals "The Cyber Hurricane!"

How a systemic exploit breaks the insurance model in 24 hours, and the 10-point triage list a CFO must execute when the "un-priceable" event happens. 

Can't wait? Shoot me a DM and i’ll send you the preprint.

"No one will insure this."
That's what a new Insurtech client was told by their former broker.

They were trying to place a complex, new E&O program.

The insurtech needed it asap to secure multiple distribution agreements. 

They were given one quote.

It was from a non-admitted carrier, the form was terrible, and the price was astronomical.

Here’s what was really happening…

When you're not in a major financial hub, your broker's access can be limited.

Their "no" isn't the market's "no."

It’s just the limit of their relationships.

They don't have the access or the technical skill to build a global solution.

We knew this risk wasn't "uninsurable." 

It was just a specialist placement.

We took it to a specific syndicate at Lloyd's of London.

(A 20 yr relationship)

We worked with them to manuscript a custom policy form that actually covered their unique exposure.

We built the program from scratch.
We won the business.

The lesson: your broker's "no" is a symptom.

It's a sign you've outgrown their capabilities.

We bring the global market solutions and mega-broker sophistication to the insurwnce operations everyone else has left behind.

We're in this market daily.

Want to follow along?

Join 2000+ FIs getting our weekly/ exclusive market analysis and Boardroom Briefings.

DM me or see link in bio.

Mark Flippen 
LION Specialty

Problems We’re Solving 

Eight insurers just paid $19 million for a mistake that takes half a day to fix.

At first, it seemed like another sophisticated cyber event.

But it was much simpler.

Hackers infiltrated the insurers through the "Get a Quote" tools right on their websites.

Many of you have these same tools on your website right now! 

The bad guys used these public tools to steal driver’s license numbers and other personal information because the websites lacked basic locks.

The crazy part?

The NYDFS warned these companies to fix this exact problem four years ago.

And now it is costing them millions.

We broke down the full story in our last Friday’s Boardroom Briefings —including the mistake that doubled the fines for some insurers.

Insurers, MGAs, and Insurtechs…

Is your digital "front door" locked?

Let’s chat before the regulators take a look. 

Send me a message if you’d like an audit and consultation about your cybersecurity underwriting risk profile.

P.S. Not ready to chat? 

Join 2,000+ financial services executives reading our weekly Boardroom Briefings to stay ahead of market risks. 

Link in the comments below. 

+ follow along at: Mark Flippen for more daily insurance and risk management insights!

graphical user interface, text, application

Are directors, officers & their boards in a ‘pincer’ moment right now being trapped from these two sides?

Burglars with robot hands? 

Hackers don't type code now, they just point an AI agent at the target and let it hammer the door 10,000 times a second.

That’s effectively what happened with the recent Anthropic / Salt Typhoon event.

A hacking team dressed an AI in a "Security Guard" uniform.  (Persona Engineering)

Then gave it "robot hands" (Model Context Protocol)

And then told it to rob 30 banks simultaneously.

It moved at machine speed.

And it only had to get lucky once.

The insurance problem(s)…

Your current Cyber policy was likely written for humans hacking computers.

Not autonomous AI agents.

If your policy is "Silent" on AI…

Could a claims adjuster argue that a rogue agent is a "misconfiguration" rather than a hack - leaving you with zero coverage? 

Worse, could crafty lawyers argue it was never the intent to cover these kinds of situations! 

(more likely) 

In last week’s Boardroom Briefing…

I broke down why SMS MFA may be dying and the 3 clauses you need to fix during you next cyber renewal…

All in the wake of the Anthropic / Salt Typhoon event. 

What are your thoughts on other coverage implications or underwriter questions coming from this event? 

P.S. I’m Mark “FLIP” Flippen from  LION Specialty.

We are a boutique brokerage protecting financial institutions through specialized D&O, E&O, and Cyber programs.

Every Friday, I send the Boardroom Briefing to 2,000+ FI leaders. I distill 200+ legal, insurance, and market-risk articles into the 5 minutes of intelligence your board actually needs to know.

Not on our distribution? Comment “ brief,” and we’ll sign you up!

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The Battle

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