Follow for daily Insights to live a longer, healthier life

Over the past decade, I’ve scaled revenue and client success at three SaaS companies from $3M to $50M+ ARR, delivering 110%+ net revenue retention and top 10% NPS scores (65+).

Today, we help recruiting agency owners & Principals ($5M–$20M billings, 5–20 recruiters) land new clients from LinkedIn by becoming a trusted authority in their market. 

Our clients are busy business owners. They don’t want to be “content creators.” 

They want done-for-you exec content that lands new clients. That’s what we do.

In the past 12 months, we’ve generated $5M+ in client billings from LinkedIn by positioning recruiting agency owners as the go-to authorities in their markets.

Our methodology:
→ Revenue Growth Engine - a 3-step system perfected with 40+ founders & recruiting agencies
→ Content strategy that generates demand for contingent and retained searches (not just likes)
→ Strategic outreach to initiate conversations with your ideal clients
→ All requiring just 1.5 hours per week from busy Principals and owners

Our results:
→ 40+ owners and Principals served
→ $5M+ in client billings generated from inbound leads via LinkedIn
→ 8+ qualified inquiries per month within 90 days (average client result)
→ Doubling client pipelines in under 6 months
→ Clients include 7 and 8-figure recruiting agencies commanding $75K+ fees and securing multi-search mandates

And we're just getting started!

We help recruiting business owners who are:
→ Tired of building trust from scratch and ready for clients who arrive pre-sold
→ Reliant on a referral pipeline that has plateaued and feels unpredictable
→ Ready to turn decades of expertise into an inbound client pipeline

Ready to turn LinkedIn into your #1 growth channel?
→ Book a 25-minute strategy call: 

https://calendly.com/rohan-karunakaran-mbww/1-1-strategy-call

Rohan Karunakaran

I sat down with LinkedIn’s first Chief HR Officer, Steve Cadigan, to share a few early lessons from his time at LinkedIn - well before it became the iconic company we know today.

Two moments from the early days stuck with me:

1// The “Obama validation” moment

When President Obama visited LinkedIn’s campus in 2011, signups jumped from 1 new member/second → 2 new members/second the very next day.

2// The “IPO perception shift” moment

On the day LinkedIn went public, membership doubled again - not because of a new product feature… but because of market validation. 

Big takeaway for founders/operators: 

Trust compounds. And visibility and perception can accelerate adoption as much as  product. In both earlier and mature stages of growth. 

Follow for the full episode dropping Friday !

CEO at Frontier | Podcast host at Founder-Led 🎙️

LinkedIn's first Chief HR Officer, Steve Cadigan, dropped this insight during our conversation and I keep coming back to it:

The companies winning right now aren’t the ones with the most resources or experience. 

They’re the ones who’ve learned to get out of their own way.

Two shifts he’s seeing:

1// Command-and-control is breaking

The most valuable companies are being built by smaller, faster, less hierarchical teams, where decisions happen close to the work, not at the top of the org chart.

2// Tenure is being replaced by 'rate of learning'

The strongest organizations are optimizing for rate of learning -  bringing in people who challenge legacy thinking and make better decisions faster.

AI is the obvious catalyst here. When the cost of intelligence and experimenting drops and the pace of change spikes, the advantage shifts to orgs that can adapt fastest.

Tesla is a clear example. Worth more than Toyota, Ford, GM, and Hyundai combined.

Not because they have more experience. Because investors believe they can out-innovate the incumbents.

Full episode in the comments below 👇

Just reviewed a recruiter's LinkedIn profile.

$150M org. 7,000+ employees. EY Entrepreneur of the Year.

Her content? Mostly podcast promos and company updates.

Great for brand awareness. But ineffective at building deeper trust, familiarity, and consideration with potential clients. 

This is the gap I keep seeing with search firm owners. 

Incredible operators. Hundreds of placements. Decades of pattern recognition.

But their content stays surface-level and could be written by anyone else. 

The stuff that would make a CEO or hiring manager stop scrolling:

- How you assess leadership talent differently  
- Why most retained searches stall at the same point 
- What separates firms that fill in 45 days vs. 120+

That’s the stuff that builds authority between conversations.

Educational content does something brand content can't - it makes a prospect feel understood before you've ever spoken. 

You want to 'get in their head' with how specifically you speak to the issues they're facing and how you'd solve them. 

Especially in exec search, where your average retainer is $100K+, arriving pre-trusted changes the sales cycle.

It's the difference between a 5-call trust tour and a 1-call close.

Most firms are sitting on decades of placement insight that never leaves the founder's brain. 

HUGE miss IMO. 

If you run a search firm and want to turn what you already know into inbound demand — DM me. Happy to share what we’re seeing work.

We're taught to chase achievement.

No one teaches us how to expand consciousness.

I came across this 2x2 and it stuck with me because it maps the relationship between the two - and how they reinforce each other.

And by consciousness, I mean self-awareness - the degree to which we’re awake to our patterns, motivations, and deeper purpose.

→ Playing the game - low agency, low consciousness. Running default scripts.

→ Winning the game - high agency, low consciousness Achievement driven by ego or fear.

→ Escaping the game - high consciousness, low agency. Insightful… but not impactful.

→ Evolving the game - high agency, high consciousness. Aligned and effective.

In my own life, breaking points - a stressful work environment and a relationship ending - forced an upgrade in consciousness

For some it's burnout, financial pressure, or a health scare - the universe giving us a shake toward a more joyful and aligned path. If we choose to listen. 

A disruption that asks: Is this actually aligned?

“Evolving the game” became a useful decision filter for me:

• Work with people I genuinely respect and enjoy
• Choose a lane that feels energizing, not draining
• Work in my 'zone of genius', delegate the rest where possible

Also, the path isn’t linear. For me, business stability came first. Consciousness expanded later.

Only then did I have the courage to step into the unknown and choose more aligned work.

Others may begin highly self-aware - and later build agency through action.

It's also easy to drift between quadrants. Staying in the “Evolving the Game” mindset isn’t automatic - it requires regular practice and commitment. 

Curious - does this framework resonate with you? Where do you see yourself on the map?

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

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The most powerful lesson I got as a baby broker. I had just spent three weeks building a 50-page PowerPoint deck.

It was a freaking work of art.

Before this lesson, I thought volume proved our value.

The senior broker on the deal stopped by my cube the day before the proposal meeting.

He took one look at the deck.

Dude! What is this?

He was a no-nonsense guy.
Knew his stuff cold.
Could carry any room with anybody and properly advise on corporate risk.

If you can't explain the deal on one sheet of paper, you don't understand the deal.

I tried to argue.
I remember saying something you say when you’re young and don’t know much…

But the risk is complex.

I’ll never forget this part…

The client simply needs a recommendation. They need us to explain it clearly and justify it.

He made me grab a single sheet of paper. Explain and justify. You got five minutes. What we told them we’d do. What we did. Make a recommendation and justify it.

Five minutes later, we had the agenda.

That’s all we did the next day.
The meeting took about ten minutes.

The CFO loved it.

Simplicity is mastery.

P.S. We still brought the full deck! Haha. But it went from 50 slides to 15 after that little exercise.

Anybody got a good lesson that’s burned in your brain from early days?

Drop it in one sentence in the comments!

P.S.S. Found an old pic of the Willis NY days, the building at Hanover Sq above Harry’s

Exactly one year ago, I took a Greece trip my old ego would’ve said NO to, and it was prob the most impactful thing I could’ve done for our business…

Chaperoning 23 teenagers. 
Going town to town in a tour bus. 
Bunking up in modest lodges. 

Walking the footsteps of the Apostle Paul.

I had become more of a Santorini guy – infinity pools, not ancient ruins.

Faith during the week? Hardly. 

The occasional Sunday, maybe. 

This one hit different though.

Over the past few years I’ve worked to crush parts of me that fueled my life for more than 40 years. 

Ambition. 
Greed. 
Excess. 
At all costs. 

Walking Paul's missionary route was the perfect marker, for this point in my life. 

In Philippi's prison, history became tangible, not just pages in an old book. 

In Thessaloniki's ancient churches, the simple message met elaborate tradition. 

The two can be balanced. 

At Meteora's impossible monasteries, I witnessed determination that defied logic.

If monks can build elaborate churches and houses on top of mountains that seem unclimbable, we can surely build a decent insurance agency! 

Ancient Corinth, was like their Vegas thousands of years ago. 

Excess now reduced to rubble. 

The transformation wasn't just mine. 

Students who normally buried faces in phones - spontaneously sang Amazing Grace in an ancient church. 

The class clown read from Corinthians with unexpected reverence. 

Seeing my daughter connect scripture to reality for the first time.

Standing at Mars Hill where Paul addressed skeptical Athenians, our school Chaplain’s words struck me deeply: 

"Some messages are worth crossing oceans for, some truths change everything they touch, and standing here makes me wonder what I'm willing to journey toward."

I wonder too…what else am I journeying toward in the second half of life?

Sometimes the most transformative experiences are the ones we almost talk ourselves out of. 

The old me prioritized the opposite of this trip. 

This one allowed me to see the value of transformations. 

Experiences. 

I've never been more thankful I said yes.

Happy Sunday, y’all

Burnout isn't a personal failure. It's a system failure. The byproduct of a culture that rewards overextension.
That's been a big part of our industry for far too long.

Our friend Brenden Corr wrote a piece recently that I think the whole industry needs to read.

78% of insurance industry employers have taken no steps to address secondary trauma in insurance professionals! And Brenden offers five practical ways to rethink burnout at the organizational level, starting with normalizing acknowledgment and recharging without guilt.

Pause and let that soak in for a second, please. 

We unpack Brenden’s phenomenal piece a bit, along with his Project 55 in this week's Mental Health edition of Friday Five.

And my conversation with Mindi Zissman for the BIG I and the massive exodus of 400,000 insurance professionals that's happening right now. We all need to be doing our part to make our industry more attractive to Gen Z.

Mental health is one of their main concerns. 

Along with a special message from TASH on how 250 Pilates classes parallels to starting and running one of the industry's fastest-growing startup boutique brokers!

And if you're new here and not on the weekly distribution…our team rips through over 200 insurance, legal and risk articles, and we write about the three events that caught our attention every week. 

It’s a five minute scannable read that hits your inbox every Friday morning at 7ET. 

Just comment “LION” below and we'll get you subscribed.

Please take a moment to at least read Brenden's piece. 

And stay covered everybody! 

Much love, yall

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

Real success isn’t building a company. It’s building a life that survives it. To the one (and all the ones out there!) building the life while I build the business.

Happy Valentine’s Day, Julie.

And Happy Valentine’s Day Y’all!

We spent 20+ years at the world's largest brokers handling the most complex financial institution placements on the planet. Then we left and built something for the clients those firms treat as "small accounts."

Regional insurers, mutuals, MGAs, ILS Funds, and Insurtech companies. 

Because of your premium spend, you get assigned to the B-team at the big global firms. Junior brokers learning exposures on your time. Or the generalists who cover financial institutions on Tuesday and manufacturing on Thursday.

We took the parts of the best global platforms that actually work. 

The carrier relationships across the US, Bermuda, and London. 
The structured approach to complex placements. 
The discipline around claims preparation...and built our entire operation around serving the institutions those firms overlook.

$250M+ in claims recovered. Hundreds of placements across every FI type. Carrier relationships measured in decades, not quarters.

You work with people who understand CFOs, General Counsels, and risk leaders at financial institutions specifically. We're specialists. There’s no B-team here.

One client told us something we've never forgotten: "You make us feel like we're your only client."

That's the standard. 
Every placement. 
All our client renewals. 
Every claim.

If you want to follow along, we break down what's moving in the FI insurance market every Friday. 

Join here:
https://lnkd.in/gP22wvyF

Check it out: 

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

One deepfake video call. 
$25.6 million gone.
Six questions that will tell you if your insurance program is built for this.

A finance director joined a video call with his CFO, his CEO, and two colleagues. 

None of them were real! 

He wired $25.6 million across 15 transactions before anyone caught it. 

That was Arup, early 2024. 

It’s the deepfake playbook the bad guys are now using at industrial scale. Your insurance program probably doesn’t cover this the way you think it does.

Social engineering endorsements that require written or email instructions. “Voluntary parting” defenses that void coverage the moment your employee clicks send. 

AI exclusions spreading through D&O, E&O, and even cyber forms that can swallow a deepfake claim whole.

No single policy owns the full loss. 

It fragments across cyber, crime, D&O, and now media liability, and the gaps live in the seams between them.

We broke all of this down in this week’s Wednesday Intelligence Boardromm Briefing. The specific coverage traps, the carrier moves worth watching, and six questions every FI executive should bring to their next leadership team meeting.

And your insurance renewal strategy. 

We also put together a one-page Deepfake Coverage Gap Checklist that goes deeper than those six questions…

The endorsements worth asking about, the exclusion language that should raise a flag, and what your renewal conversation should actually sound like in 2026.

Our Boardroom Brief subscribers got the offer. If you’re interested in taking a deeper dive here, DM me an we can get you the same offer… 

P.S. we need to be connected and must be a buyer of insurance at a financial services company

Deepfake Fraud 

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

The bank teller was kidnapped at gunpoint with her son.
This one didn’t happen overseas. It happened here…

Northeast U.S. End of her shift at a regional bank we handled.

Two masked kidnappers grabbed her and her 8-year-old son in the parking lot.

They wanted her to open the vault and hand over the cash.

She was a teller. She didn’t have vault access.

When the kidnappers realized their mistake, they released her. But not before they dropped her young son off in the mall parking lot mid-kidnapping. And subjected her to serious trauma.

The aftermath hit hard.

Severe PTSD for both mother and son. She couldn’t return to work. Her son needed ongoing counseling. 

The family had to relocate for safety.
This is where their K&R coverage stepped in. Not with a ransom payment. There wasn’t one.

With comprehensive trauma support.

Medical and mental-health treatment for both victims. Full salary continuation. Security consulting to assess ongoing risk. Relocation assistance. Counseling support for her son.

Total cost of care was well into seven figures.

This was my first kidnap-and-ransom claim. One of the hardest we’ve ever handled.

And it changed how I talk to every financial institution about K&R coverage. Because the families who need it most are rarely the ones companies think first to protect.

The bank tellers. Branch managers. the clams adjusters. The underwriter and his daughter. Warehouse supervisors. Anyone criminals think can get them money.

We break down coverage gaps like this every week in the Friday Five. And we go deeper most every other Wednesday in our Boardroom Briefings.  

Comment “BRIEF” for the link.

K&R case study: managing the details 

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!

Soulset is better than mindset.
"It will always work out," I like to say. "Never a doubt," one of our mentors always says.

But will it really? All work out. 

Last week I stood at each end of that spectrum.

My youngest daughter showed me a cool insta clip from a young woman named Izi Murray. She’s a former D-1 college soccer player who helps young athletes.

Izi was talking about how most winners have a "winning story" that is on repeat in their heads at all times, regardless of what is happening. 

I was nodding as we watched it.
Because something similar is always running through mine.

That same day...

One of my teammates confessed to me that she worries a lot.
She feels the weight of learning the business. She feels the uncertainty.

She looked at me and asked if I truly believe that. That it will actually work out?

"100% without a doubt"

Then I told her why.
It’s not because we have a perfect business plan. Or that doin what we’re trying to do is easy. To the contrary, actually. 

It’s because my belief is anchored in something that doesn't fluctuate with the rollercoaster ride of hard we’re on.

It is based on my faith in Jesus Christ.

I didn't preach. Didn’t push.
I just told her the truth about where my peace comes from.

When we left corporate in late 2022, I thought the freedom we wanted was about marketing. Bold posts without approval processes.

I was thinking too small.

The real freedom wasn't about building a brand.

It was about being able to look a worried teammate in the eye and tell her exactly who is in control.

I didn't leave the corporate world just to build a business. I left so I could stop filtering my soul.

If you are a leader, your team is looking at you. They are looking for panic.

If you can show them Peace,
and tell them the Source of that peace, you might give them something a paycheck can't buy.

"Never a doubt."

What’s your version of “Soulset?”

Does the industry have enough capacity for all of this? 

80% of PE firms experienced cyber disruption during the hold period last year…

Average financial hit: $2.1 million per deal.

CFOs, and board members…

That’s not a headline from a vendor selling cyber tools. That’s Kroll surveying 325 PE executives and laying out real world scenarios happening now.

In my 20+ years placing coverage for financial institutions and private equity firms, this kind of breach activity on transactions is unprecedented. 

→ Cyber risk migrates from IT line item to material deal risk

→ Smaller PE firms absorb outsized losses because they lack the governance infrastructure larger firms have built

→ The gap between who has a formal cyber mandate and who handles it case-by-case predicts the financial outcome

Meanwhile, $77.7 billion in US data center construction starts hit in 2025 alone. Another $88 billion is slated for the first half of this year. 

It’s a massive boom for property markets. But again, I wonder if there’s enough capacity! 

Weigh in in the comments, if you have an opinion…

And the plaintiffs’ bar just expanded its litigation analytics to 1,200 additional state courts. They’re mapping your judge’s preferred language before they file.

Yikes! 

If you want the framework sophisticated boards use to stay ahead of these three converging forces…

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 yall!

P.S. Our Wednesday Intelligence drops every other week with war stories from our claim files. Friday is your market intel, Wednesday is your coverage stress test. Ask us about it.

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 

If you’re building the future of insurance, don’t let a broker from the past slow you down like this…

A new Insurtech client and I recently had a funny chat after he hired us.

(a case study on why all Insurtechs should be working w us!) 

Let’s call new client, Dan.

Dan is building a spaceship.

He employs a full team of engineers. Their platform is ecosystem-based. Claude Code, n8n automations, AI agents and swarms, and custom built proprietary models running on their private server. 

All of it built so his underwriters can underwrite faster with more sophistication, source better submissions from their broker partners, and generate quotes and bind policies in minutes, not days.

The future that’s already here. 

He’s moving at Mach 10.

But when he showed me his E&O insurance program, we both kind of laughed. He knew it too. 

It was a bicycle helmet.
For a team flying a spaceship! 

His previous broker had given him an off-the-shelf policy full of exclusions for “tech issues,” which is his entire business. 

They’d split his Tech E&O and MGA E&O across two different carriers, creating the classic finger-pointing problem when a claim hits both. 

The whole thing was designed for a slow, manual MGA like we had in the  1900s! 

Every time Dan tried to launch a new product, his broker would say, “Hold on, let me go ask the carrier.” Then two or three weeks of silence. Three weeks is a lifetime in Insurtech.

Dan told us: “My technology is my edge. I need a policy and a broker that moves as fast as my team and our code.”

So we didn’t go to the standard market. We went global. Built a program on our manuscript policy from scratch. All his gaps taken care of.

Now when Dan wants to launch, he launches. His insurance moved from drag chute to launchpad.

Dan stopped settling for a broker who couldn’t keep up. Maybe you should too.

Why LION for Insurtechs? 

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!

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 

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!

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