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

One of my highlights of 2025 was spending a week in Sedona in early December.

I'd just wrapped a retreat with the Becoming the Bridge community (great humans!) and made a last min decision to extend my stay.

There’s something about the high desert, red rocks, and mountains that have been around for thousands of years that naturally invite moments of silence and stillness.

And yes — the energy vortex is real !

What was one of your highlights from 2025?

CEO at Frontier Growth Engine | Podcast host at Founder-Led 🎙️

One of my highlights from 2025 was attending a Dr. Joe Dispenza advanced retreat in Nashville. 

It was a fully immersive 7 day experience. 1,500 people. 14-hour days from 6am-8pm. Some days started at 4am. 

A few key takeaways that stayed with me:

1. Most people are living in the past:

Most people are living in a loop where today looks like yesterday. 

If we keep making a copy of a copy of a copy - like an old cassette tape - we’re becoming a cheaper, more diluted version of our true selves. 

To break the loop, we must become greater than the body, the mind, and the environment — all of which are largely conditioned by the past.

“Overcoming is the becoming process.”

The resistance we feel — to get out of bed, go to the gym, or have the hard conversations — is often the past being projected into the future.

The mind predicts an unpleasant experience so the body responds with resistance or avoidance. 

If we can overcome ourselves in those small moments, we step into possibility to a life that feels both more exciting and more peaceful. 

As I wrote in my journal: “If I can overcome myself in the morning, everyone else will be easy” HA!

2. Opening the heart:

The universe only gives us what we feel worthy of receiving. And worthiness comes from an open heart. 

Fear and frustration don’t open the heart. A constantly analytical mind doesn’t open the heart (learned that one the hard way 😄).

There’s nuance here — including practical ways I’ve found to cultivate an open heart — which probably deserves its own post.

The true masters (Jesus, Krishna, Buddha) knew the path: remove anything that stood in the way between them and an unconditionally open heart. 

3. Meditation as remembering:

The world is designed to help us forget our true selves:

• Societal conditioning
• The educational system
• The food we eat

The invisible scripts — when to buy a house, have children, what “success” is supposed to look like, etc, etc. the list is long !

The idea is not to fight against it. But to notice this old software program running and make intentional choices to update it. 

It starts with awareness. 

Meditation is the act of remembering. Of tuning out the noise so we can tune into the intelligence whispering within us.

From a neuroscience perspective, this often corresponds with shifting from high-beta analytical brainwave patterns into slower, more coherent alpha and theta states — states associated with calm focus, creativity, emotional regulation, and heart-brain coherence.

The result - the mind becomes an instrument of the heart:

• Decisions feel clean
• Work feels more easeful
• We feel more regulated, present and grounded

The ultimate goal: 

“Get so good doing it with your eyes closed, you can do it with your eyes open.” 

There were many more takeaways, including a breakthrough experience I had. 

It might be a little “woo” for LinkedIn, so let me know in the comments if you want a Part 2 👇

B2B lags B2C by ~10 years.

Had a great conversation with Will Leatherman and he said it perfectly:

"If B2C’s creator era kicked off in 2014… B2B is right on schedule"

And the playbook is already written:

2016 → B2C social goes mainstream
2019 → Personal brands disproportionately outperform corporate brands
2020s → Distribution > product

Now the same shift is hitting B2B.

Founders & CEOs are becoming the face of their products & services.

Those who start now will be 2–3 years ahead by the time everyone else catches on.

I thought I was decent at discovery calls.

Then I role-played with the author of Gap Selling.

He dismantled my process in 10 minutes.

3 takeaways that completely changed how I run discovery:

1. Product-centric vs. help-centric selling:

Most founders (myself included) jump to the pitch too quickly. 

“Aha — they mentioned a problem. Let me tell them about our solution.”

Keenan . calls this product-centric selling.

Help-centric selling is different.

It goes deep on:
→ What are you trying to do?
→ What’s preventing you from doing it today?
→ What is that costing you?
→ How long has this been going on?
→ Is it actually worth changing?

If you’re not uncovering those, and gettting them to emotionally feel and articulate the pain of their current state, the pitch — and the decision — won’t have real stakes. And will likely fall flat.

2. Get them to quantify the gap

Keenan’s rule: define everything.

“Onboarding takes too long.” How long?

“We’re losing revenue.” How much?

Most founders hear a problem and move on.

But vague problems don’t create urgency. Numbers do.

When they say “$700K is at risk”  it becomes real.

3. Not going deep on consequences

This one got me.

Keenan didn’t stop at the surface issue.

He kept asking: 
→ What happens if referrals dry up next quarter? 
→ What's it costing you to spend 20 hours a week on outbound that goes nowhere? 
→ If you're spending 5 calls just to build trust — is that the best use of your time?

By the end, "I should probably invest more in thought leadership" became a $500K pipeline gap.

He wasn't manufacturing fear. He was helping me connect what I already knew.

Selling isn't about pitching features — it's about the cost of inaction.

Founder-led sellers - Which is harder for you: finding the pain or getting the prospect to quantify it?

Agency > Intelligence.

Garry Tan (Y Combinator CEO) and Andrej Karpathy (former Tesla AI Director) are both saying it:

When AI puts world-class intelligence on tap for $20/month, the bottleneck is no longer knowing.

It's acting.

For founders building movements, this means:

Good product + great distribution > Excellent product + weak distribution.

Product still matters. But distribution is the multiplier. And there's a crowded graveyard of "technically superior" products that never found their market. 

George Mack has a framework for this - the "Jail Cell Test":

"You wake up in a 3rd world jail cell. You’re only allowed to call one person you know to get you out. Who do you call?"

You don't call the person with the the most intelligence or credentials. You call the person with agency.

The one who improvises. Who finds the gap in the fence. Who happens to life instead of waiting for life to happen to them.

I see brilliant founders failing this test every day.

They have the expertise. The track record. The intelligence.

But they're Person A in the image - stuck on the island, spelling "HELP" in the sand with sticks:

• Waiting for referrals
• Waiting to be "discovered"
• Waiting for some future moment before they share what they know

Person B used the same sticks to build a raft.

• Narrating the struggle while they build
• Recruiting before they have a finished product
• Treating distribution as a force multiplier, not a marketing chore

Same resources. Different agency. Different outcomes.

The gap in 2026 isn't knowledge. It's nerve.

High agency for your movement means turning your expertise into trusted distribution - not waiting for permission that isn't coming.

Start building the raft.

What's one move you've been over-analyzing that you could execute today?

Image credit: George Mack

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

JLT Specialty USA

Senior Vice President

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

Vice President

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

Assistant Vice President

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

A Lloyd's underwriter once told me:
"I am not betting on the spreadsheet. I am betting on the people."

That advice saved my clients millions over the last 20 years.

I was 28 years old. I was sitting across from him at my first PLUS event. He was a veteran underwriter from a well known Lloyd’s syndicate. 

He had been u/writing D&O since before I was born.

I had my stack of papers. My charts. 5 years of loss data. I was all ready to go thru the math.

He didn't look at the papers. He looked at me and asked one question…”If the building burns down, will they try to save the furniture, or will they let it burn?"

This was an inv mgmt account. Why was he asking about the building burning down!

Still makes me chuckle. 

That moment though. It changed how I viewed the trade.

The "spreadsheet" broker thinks risk is a math problem. They think if they tweak the deductibles enough, if they best position the financials the risk diminishes.

The "Trading" Broker knows risk is a human problem. We don't just sell your data to the market. We sell your character to the market.

What’s your move when it hits the fan. 

When we bring a deal to market, we don't just send the PDF. The submission. We tell the story of the management team. We explain why you are a safe bet.

20 years on, that underwriter is still right. The spreadsheet tells you the price. The story tells you the risk.

And the best terms always go to the “people,” w the best stories.

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

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

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

Many still do the first. Even the sophisticated ones.

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

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

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

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

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

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

Building the New Standard:

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

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

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

- FLIP

Weekly Boardroom Risk Intelligence

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

A smooth renewal usually means nobody looked.

A mutual insurance company brought us in to review their own program. Their biggest agent, the one who sells for them, had been handling their corporate D&O and E&O for years. Long-standing relationship. Comfortable renewal. Felt efficient.

The problem is incentives.

That agent's job is to maintain a smooth, profitable relationship. Not to run a technical review that exposes gaps and creates friction. The renewal feels easy because it's just a rollover of last year's terms.

We ran their program through our 8-point stress test. Market positioning. Carrier selection. Coverage structure. Benchmarking against peers. Limits. Retentions. All of it.

We found over a dozen significant coverage gaps.

Problematic fraud exclusions buried in the policy. Vague allocation language that lets carriers decide how much of a claim is their problem versus yours. Notice provisions that were a trap.

A relationship renewal will miss these 100% of the time.

We put our manuscript form next to the vanilla form they'd been sold. The difference was undeniable.

The technical review was the foothold. That's what proved acumen over convenience.

They now trust us with their entire P&C and financial lines placement.

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In 2017, NotPetya caused $10 billion in global damages. Maersk lost $300M. FedEx lost $300M. All at once.

For carriers writing cyber insurance, it exposed something terrifying:
traditional underwriting models were completely broken.

Insurance pricing relies on the law of large numbers and diversification. Actuaries can model 10,000 fires because a fire in one house doesn't cause a fire in another. They can model a real hurricane because its path is geographically limited.

A "Cyber Hurricane" invalidates both assumptions.

Geographic diversification is an illusion. Carriers assumed writing policies in 50 states provided diversification. But every policyholder, whether in Ohio or Texas, is in the same location: the internet. A single vulnerability in a core operating system or cloud provider connects them all.

Correlation is near-total. The "event" is the exploit itself, which hits 1,000 or 10,000 or 100,000 clients simultaneously. The loss ratio isn't 70% or 90%. It's 1,000% or more, in an instant.

And reinsurance treaties are dangerously ambiguous. Is a systemic ransomware attack "one event" (one retention) or "10,000 events" (10,000 retentions)? While lawyers fight that out for years, no reinsurance money is coming today.

In less than 24 hours, a healthy A-rated carrier could be rendered technically insolvent.

The near-misses are already happening. The question is whether balance sheets, capital structures, and reinsurance treaties are built to survive an event that operates outside every historical precedent the industry has ever relied upon.

We help carriers see the steamroller before it hits. DM me if you want to benchmark your cyber exposure against your peers.

I had two uncomfortable conversations last week. And sadly, I plan to have a dozen more before the quarter ends.

First with a CFO, next was General Counsel. 

Back-to-back insurance policy reviews. Many executives would rather have oral surgery than do an insurance review. Believe me, I get it.

But both execs looked at the coverage concerns we found and asked the exact same question. 

"Why didn't my broker catch these?"

After two decades, I still hate answering that question. Because the answer gets uncomfortable. The gaps we find are rarely complex. 

They’re systematic service failures. Your broker just wasn’t looking, sir. Or worse, they don’t have the skill set to see these, madam. 

• Fraud exclusions that trigger too early.
• Allocation language that is vague on purpose.
• Notice provisions that fail during a crisis.
• D&O and E&O programs that don't talk to each other.

Last week weren’t "typos." They were foundational risks that are leaving these executives’ personal assets exposed. And the balance sheet with a false hedge.

Why this is happening now…

For years, the mega brokers have moved business that doesn’t generate $1M in commission into Small Business Units. The aspiring big brokers have copied this model like lemmings. That means one broker handling 200+ accounts at a time. Even a super broker can’t manage that kind of load.

And we all know the super brokers aren’t in the small biz units. 

So your program — which is meant to protect the board, the balance sheet, and your personal assets 
— gets transactional service. 

Add to that the recent agitation. 

All that broker consolidation you’re reading about in the industry rags. 
Your "trusted advisor" is distracted by their own merger. Their new company bogged down w internal crap. Your team is in flux. And litigation might be blocking you from the talent you actually hired.

All the while...

We are in a market with the most favorable terms we've seen in years.
But you can't access them if your broker is distracted, or just hitting renew.

If you are a CFO or GC at a financial institution and you haven't stress-tested your program in the last 12 months, let us help you. 

Grab a time on my calendar. Link👇🏻

Your coverage either works when you need it, or you find out it doesn't.

We saved the best meeting of 2025 for one of the last days…

This year Julie and I are finally getting around to doing a couples’ year-end review.

Here are the 25 questions we’re using to reflect on the past year and plan together for 2026…

RELATIONSHIP

1. When did you feel the most loved by me this year?
2. What’s one thing we’ve learned to appreciate more about each other this year?
3. How have we supported each other’s goals this year and where can we offer more encouragement?
4. What’s one thing you’d like to see more of in our relationship next year?

FAMILY LIFE

5. Is there something you feel we handled really well as parents this year?
6. What was the most challenging part of parenting for you in 2025?
7. Are there any new skills or values you want to focus on as a family in 2026?
8. How can I better support you in your parenting role?

CAREER & VOCATION

9. What was the most rewarding part of your work this year?
10. How did work challenge you and what did you learn from it?
11. What boundaries do you want to set around work in 2026?
12. Is there something new you’d like to pursue or focus on in your career next year?
13. How can I better support you in your professional goals in 2026?

HEALTH

14. How did you feel about your overall energy and mental health this year?
15. Are there any positive health habits you’re proud of implementing this year?
16. What’s one thing we could do together to stay healthier in the new year?
17. What health habit are you most excited to work on individually in 2026?

SPIRITUAL LIFE

18. How have our faith and spiritual practices evolved this year?
19. What moments this year felt the most meaningful or grounding for you?
20. Is there an area of our faith we would like to expand upon?
21. How can we nurture our spiritual lives together in 2026?

RANDOM

22. What’s a favorite memory we created together this year?
23. If you could relive one day from 2025, what would it be and why?
24. What’s something surprising you learned about yourself this year?
25. What’s one adventure or goal we should tackle as a couple in 2026?​​​​​​​​​​​​​​​​

What did we miss? 

Happy New Year, everybody!

Median jury awards climbed from $21 million to over $51 million in five years.

Yet, risk costs? Still trending down. 

Thermonuclear verdicts exceeding $100 million appeared 27 times in 2023. In the previous decade, there were roughly three.

Traditional exposure models are becoming dangerously outdated.

Plaintiff attorneys use what's called the "Reptile Theory" to bypass logic entirely. They trigger primal survival instincts in jurors. The goal is to make the jury feel like the defendant's conduct threatens the community's safety. Once that switch flips, rational damages calculation goes out the window.

The nationals are responding with million-dollar defense strategies.

But regional and mutual insurers have an overlooked advantage: community presence.

Your adjusters living in town and coaching Little League is better verdict prevention than anything the nationals can buy. Jurors are less likely to deliver nuclear verdicts against companies they see as neighbors.

The era of predictable verdicts is over. Your D&O limits need to reflect that.

P.S. We built a 5-day email course on the D&O mistakes we see most often. Get started here: https://lnkd.in/gVzZgGPW

OpenAI just terminated their analytics vendor after a breach exposed customer data.

Mixpanel disclosed the breach on November 26. The Wednesday before Thanksgiving. Quietest possible moment for news.

Their disclosure said almost nothing. They acknowledged "unauthorized access" on November 8. Didn't say what was taken, how many customers were affected, or how hackers got in.

Two days later OpenAI published their own disclosure confirming what Mixpanel hadn't: customer data was actually stolen. Names, email addresses, approximate locations, device information.

Mixpanel has 8,000 corporate customers. Each of those customers may have millions of end users.

The breach scope remains unknown because Mixpanel isn't talking. Their CEO hasn't responded to press inquiries about whether hackers made ransom demands or whether employee accounts had multi-factor authentication.

Analytics vendors collect more behavioral data than most organizations track in their vendor inventories. Every tap, click, swipe, page view. Attached to device identifiers, timestamps, network information, user IDs. Mixpanel even offers "session replays" that can inadvertently capture sensitive information.

For financial institutions: which of your vendors collect behavioral data on your customers? 

What would you have to disclose if they got breached?

A breach at your analytics provider creates the same notification obligations as a breach of your own systems.

Immediate Action: ask your technology team which vendors have tracking code embedded in your customer-facing applications. 

Map what data flows to each.

If you don't know, that's your answer.

P.S. We created a 5-day email course on avoiding D&O policy mistakes and protecting your personal assets. 

These kinds of events can not only cause a cyber liability loss, they can result in your board being sued, too. 

Comment BLUEPRINT and I'll send it over.

[LINK: https://lnkd.in/gVzZgGPW]

President Trump just signed an Executive Order to preempt state AI regulations. Now what?

Insurers have spent the last six months building compliance programs around state requirements and the NAIC Model Bulletin.

The Executive Order uses two enforcement approaches. A DOJ task force to challenge state laws in court. And provisions to withhold federal funding from states enforcing "burdensome" AI rules.

But state regulators aren't pausing.

Colorado's AI governance rules took effect October 15. New York's DFS continues implementing AI guidelines. The NAIC issued commentary in September affirming state authority and opposing federal moratoriums.

No states have signaled a halt to enforcement while this plays out in court.

Executive orders face serious challenges preempting state insurance regulations. The McCarran-Ferguson Act reserves insurance oversight to states. Courts have historically upheld this structure.

Even Florida Governor DeSantis called it potential federal overreach.

Litigation could take months or years to get sorted. State rules apply until courts say otherwise. Institutions that pause compliance efforts waiting for federal clarity may face regulatory penalties in the meantime.

Read about our guidance to clients in this week’s Friday Five Boardroom Briefing. 

Like this kind of post? You’ll love our weekly Boardroom Briefing!

Comment “BRIEF,” if you’re not on the distribution, and we’ll get you subscribed! 

Stay covered everybody! 

FLIP

P.S. over 2,500 FI executives are reading these briefings weekly! Here’s a link to subscribe…

https://lnkd.in/gP22wvyF

What do DEI programs and billing fraud have in common?

For those of us around during the credit crisis years, you’ll likely remember when 19 of the top 30 banks got crushed, the last time the DOJ dusted off the Civil War Era False Claims Act! 

That was for lending services. 
Now it’s diversity, equity and inclusion. 

DOJ just launched False Claims Act investigations into corporate DEI programs.

Billing fraud? Nah. 
Not defense contractor over-billing either. DEI practices.

CFOs, GCs, and board members at regional insurers, reciprocals, and mutuals…maybe all financial services companies. 

This could affect you if your institution has federal touchpoints — SBA relationships, TRIA coverage, federal program participation.

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

→ Whistleblowers can initiate lawsuits even if DOJ declines — and collect a percentage
→ The investigative phase alone imposes significant document production and reputational costs 
→ The time to build the paper trail is before anyone asks for it

If you want the framework sophisticated institutions use to treat compliance as balance-sheet protection…

…read about it in this week's LION Specialty ‘Friday Five’ Boardroom Briefing.

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

Stay covered out there everybody!

P.S. If you're wondering whether your certifications create FCA exposure, let's talk. 

DM me

And join 2,500 financial services executives reading our weekly Briefs…

https://lnkd.in/gP22wvyF

How to know if your insurance coverage will actually respond during a claim—in under 3 minutes:

(buyers, trust but verify your structure)

After 20+ years negotiating coverage for financial institutions and private equity firms, I've found every program that actually works passes three tests.

Swipe through to see if yours would pass →

There is a quiet dysfunction that plagues even the best brokerages. 
We built something different. Inspired by the world's Blue Zones. Regions like Okinawa and Sardinia where people live longest due to their systems, not their genetics—we designed an environment for professional longevity. We call it the Insurance Blue Zone.

There's a coverage structure most Insurtech MGAs have that will fail them at claim time.

I call it the Two-Carrier Trap.

Two policies. Two carriers. Tech E&O with one. MGA E&O with the other.

When the claim comes in, the tech carrier says "that's an operational issue, not ours."

And the MGA carrier says "that's a tech failure, not ours."

You're caught in a finger-pointing battle while nobody pays.

But for an Insurtech, the tech is the operation. You can't separate them. 

The risk is singular. An insurtech we work with had this exact setup. They came to us after they'd outgrown their startup coverage. They'd bought direct back then, went online, checked the box. Vanilla program. Generic terms. And the Two-Carrier Trap baked in.

We took them to the global market. US, Bermuda, Lloyd's. Arbitraged the markets, to get a better form, not just a better price. Found a carrier willing to build a single unified policy. 

One carrier. All E&O perils under one roof.

→ No coverage gaps between policies
→ No finger-pointing at claim time
→ No arguing over which carrier responds

P.S. We write about structural gaps like this in our newsletter:

https://lnkd.in/e8qkpZkY

The orphaned deal was too small for reinsurance brokers. Too complex for standard retail brokers. So it sat in between.

A retirement and insurance organization wanted to offer D&O protection to the churches they served. They didn't have the policy forms, the state filings, or the underwriting criteria to do it themselves. So they went to a major carrier to structure a white-label program.

The structure: carrier provides the policy form, underwriting requirements, and claims handling. The organization handles front-end marketing and gets some underwriting authority. And they take 50 percent of the risk on the back end.

If there's a claim for a dollar, the organization pays 50 cents, the carrier pays 50 cents. Effectively how some reinsurance trades work.

But here's the problem. About $7 million in premium running through the program. Maybe a million in revenue. Reinsurance brokers don't engage until you hit $50 million in premium. So deals like this get orphaned.

Even worse, many try to handle them in house.

No broker. 

We've done enough of these to know how they work. And how to get them done. We know commercial market structure. We know enough reinsurance to be valuable. The key, we know that when a client is taking risk, the job changes.

On a normal retail deal, our job is to get you the broadest coverage at the best price. On a deal like this, where the client is also taking risk, we help calibrate. Where is coverage too broad for your appetite? Where does it become cost-prohibitive for your underlying clients? How do you balance what you're offering with what you're retaining?

These deals exist. They just don't always find the right broker.

Every other Wednesday we break down insurance structures and market signals like this. Join the pride: https://lnkd.in/e8qkpZkY

After 25+ years in insurance, I've watched too many talented people sacrifice too much for “success”... 

The traditional insurance model is:

→ Individual producers grinding alone
→ 60+ hour weeks disguised as "dedication"
→ Compensation structures that pit teammates against each other
→ Knowledge hoarding as competitive advantage
→ Burnout treated as inevitable

( for pros trying to be elite ) 

So we‘re building something different..

An “Insurance Blue Zone.” Seems a bit woo woo at first! But, give me another min here…

When we look at the world's actual Blue Zones - regions where people live to 100+ at extraordinary rates - you see their longevity comes from their systems.

And the principles that create longevity in Italy, Japan, California are ones you’ll see in LION.

1. Purpose Over Performance

Blue Zone communities have ikigai - reason for being. 

At LION, we solve problems that matter instead of chasing revenue targets. When your work has meaning beyond metrics, sustainable intensity replaces destructive grinding.

2. Community Over Competition

Centenarians in Blue Zones live in tight social networks. 

We structured LION as "Elevated Ensemble" - shared success, collective expertise. Knowledge flows freely because everyone wins when anyone wins.

3. Movement as Medicine

Blue Zone residents walk naturally throughout their day. 

Our workflows eliminate artificial urgency. Steady progress over frantic sprints. 150-day renewal orchestration instead of 90-day panic cycles.

4. Stress Resilience, Not Stress Avoidance

Blue Zone communities face challenges but have strong support systems. 

We embrace complex risks but tackle them systematically as a team. "Crucible Forged"—edge earned under pressure, together.

5. Sustainable Rhythms

Blue Zone eating patterns: regular, moderate, mindful. 

Our workload design prevents feast-or-famine cycles. Consistent quality over erratic heroics.

These principles have led to:
→ 92% team retention over 20 months
→ 30% faster project delivery
→ Zero compromise on quality
→ People actually want to be here 

We stopped asking, "How do we make people work harder?"

And started asking, "How do we help people thrive longer?"

Most firms push until people break.

We built a system where excellence is the natural outcome of sustainable practices.

The insurance industry treats burnout like a badge of honor.

But the world's healthiest communities prove that longevity will always beat intensity.

P.S. I wrote about our Blue Zone in our latest “Wednesday Intelligence,” blog series yesterday. See link in comments…👇🏻

A health insurer embedded an off-the-shelf AI solution into their claims process. Regulators asked how it worked. 

The company said they didn't know! 

Florida's insurance commissioner is now pushing two bills that would require humans in the loop whenever a claim is denied.

Other state regulators are watching.  

Rep. Hillary Cassel filed HB 527. Sen. Jennifer Bradley filed SB 202. House Speaker Daniel Perez declared December 8-12 "Artificial Intelligence Week" with subcommittees examining AI across their jurisdictions.

Commissioner Michael Yaworsky outlined his framework to the Senate Banking and Insurance Committee: disclosure when AI is used, auditing that confirms systems do what they're supposed to do, and a human in the loop who actually understands the technology.

He's not calling for AI elimination. "I'm not an opponent of AI," he told lawmakers. But he wants carriers to be able to explain what their systems do.

The bills aren't law yet. But the regulatory direction is clear.

Quick question: if someone asked your team to explain what your AI systems do, could they?


P.S. We built a 5-day email course on the D&O insurance mistakes we see boards make most often and how to fix them. Comment BLUEPRINT and I'll send it.

AI in Your Claims Processes? 

The market made money. But the risk exposure got worse.

Between June 30 and November 30, U.S. market caps expanded by $10.7 trillion. During the same period, securities litigation risk exposure climbed to $13.7 trillion. Up nearly $2 trillion since July.

806 additional high-risk disclosure events on the NYSE and NASDAQ triggered material stock declines. The rate of litigation-triggering losses outpaced equity growth by 1.5 percentage points.

The million dollar question heading into 2026: Will D&O underwriters adjust their pricing models? 

Companies with higher-than-average frequency of adverse corporate events could face premium increases in 2026.

But financial institutions carry the lowest lawsuit risk score in the market at 6.6%. That improved by 0.30 percentage points vs. other industries. For comparison, tech companies saw their risk spike by 5+ points to 28.1%.

FIs, you’re not riding the AI hype cycle volatility that's hammering tech D&O pricing. That stability matters at renewal. Make sure your underwriting partners know it.

One way we’re advising our clients: take action. 

Audit your two-year corporate disclosure record before your underwriter does.

P.S. We built a 5-day email course on the D&O mistakes we see most often. Comment BLUEPRINT and I'll send it.

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