LinkedIn Growth Engine

Building profitable audiences for established recruitment firms ($1M-20M revenue).

Founder & CEO

Longevity Life

Helping people live measurably longer, healthier lives. Our mission is to add 1B healthy years to humanity.

Founder OS

Hired as first Founder Success Manager (FSM) to:

- Build out backend continuity program (OS+) from 0-1
- Build & deliver upsell motion from OS → OS+
- FSM to 30+ founders. Player-coach to newly hired FSMs

Results:
- Helped grow OS+ ($25K offer) to 200+ members
- Closed $250K in cash collected upsell revenue
- Collected 20+ 5-star testimonials on TrustPilot
- Developed 10+ SOPs, playbooks and frameworks that comprise core curriculum

Founder Success & LinkedIn Growth Instructor

KarmaCheck

Head of Customer Success

Blueshift

Head of Customer Success, EMEA (2019 to 2021)

Director of Customer Success

Mixpanel

Enterprise Customer Success

Optimizely

Onboarding Specialist

Ashraya Initiative for Children (AIC)

Supported the development of AIC's Education Outreach Program

Dada

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 $5M to $30M+ ARR, delivering 110%+ net revenue retention and top 10% NPS scores (65+).

Today, we help recruitment firm owners & Principals ($1M–$20M billings, 5–20 recruiters) turn LinkedIn into their #1 revenue channel by building trusted authority in their market.

Our clients don’t want to be “content creators.” They want visibility that converts into qualified pipeline and high-intent retained searches. That’s what we do.

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

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

Our results:
→ 40+ founders and Principals served
→ $5M+ in client revenue generated from inbound leads via LinkedIn
→ 4+ qualified inquiries per month within 90 days (average client result)
→ Doubling client pipelines in under 6 months
→ Clients include 7 and 8-figure retained search firms commanding $50K+ fees and securing multi-search mandates

And we're just getting started!

We help recruitment founders 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 15-minute strategy call: 

https://calendly.com/rohan-karunakaran-mbww/1-1-15-min-consult

Rohan Karunakaran

The talent landscape is shifting in real time.

Mass layoffs. Hiring freezes. Leaner teams:

I sat down with Gina Hadley to unpack what top CHROs and hiring leaders are doing to stay ahead.

Her company The Second Shift was just acquired by Sinecure, Inc.  — and is shifting from “flexible talent for women” → a total talent solution built for leaders designing teams that are adaptive, resilient, and capital-efficient:

• On-demand senior talent for mission-critical work
• Retained search when the role should become full-time
• Scalable recruiting for team build-outs

For CHROs and hiring managers, that means:

• Solve critical work fast without waiting on headcount
• Validate culture fit before committing full-time
• Reduce hiring risk without slowing execution

And this isn’t “send a contractor and hope it works.” 🤞

Sinecure is rolling out training, documentation, and tailored enablement to help HR leaders deploy on-demand talent successfully — KPIs, milestones, onboarding playbooks, culture integration, and more.

This is the evolution of flexible work — applied to high-complexity knowledge work.

Full clip below 👇

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

I didn’t start posting content because I was “trying to build a personal brand.”

I posted because I was obsessed with longevity — epigenetic age tests, biomarkers, health experiments.

That was it.

Then something unexpected happened:

People started reaching out.

Even Bryan Johnson slid into my DMs after I tagged him.

That’s when I realized something most founders still miss:

• You don't need a massive audience
• You just need consistency + a POV worth sharing

Because unlike ads and referrals, content compounds.

One great piece of content can:

 • Spark conversations with dream customers
 • Position you as the trusted expert before the first call
 • Generate leads months — sometimes years — later

A founder-led content strategy isn’t about “being an influencer.”

It’s about controlling your destiny and attracting your perfect-fit clients. 

Full clip below 👇

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.

90% of your future customers will never like, comment, or share your content.

And they'll still buy from you.

Last month we analyzed booking data across our clients. Sales calls, demos, strategy sessions.

The pattern was clear: 4 out of 5 people who booked had never engaged with a single post. No likes. No comments. Nothing.

They'd been watching the entire time.

I talked with a SaaS founder last week who was ready to quit posting. "I'm getting 20 reactions per post. Feels like I'm shouting into the void."

Three days later, someone booked a demo. First conversation ever. The prospect said: "I've been following you for 6 months. I know exactly how you work."

Zero prior engagement.

Here's what we've seen: The decision-makers - the ones with budget authority— they're professional lurkers. They don't engage. But they're paying attention.

The recruiting firm owner who lands a $125K retained search from someone who never engaged once.

The agency founder whose biggest client watched silently for 90 days before reaching out.

Most founders quit in the first 90 days because they think low engagement means it's not working.

Meanwhile, hundreds of ideal customers are watching, evaluating, building trust invisibly.

The best leads aren't engaging. They're watching.

And when they're ready, they'll reach out.

The question is: Will you still be showing up?

B2B marketing runs 10 years behind B2C. 

Which means the future is obvious:

2014 → Ryan Reynolds buys Aviation Gin. 

Sells for $610M. Then Mint Mobile. Then Wrexham FC. 

2017 → Rihanna launches Fenty. Billion-dollar brand in 3 years.

George Clooney, Dwayne Johnson, Kim Kardashian… 

Same playbook: Build audience → Launch product → Print money.

Now it’s happening in B2B:

Brian Chesky turned Airbnb into a movement by telling the story himself.

Dharmesh Shah & Brian Halligan coined “Inbound” and built HubSpot into a category by educating the market at scale.

Jason Lemkin built SaaStr into the #1 SaaS community — deal flow, partnerships, LPs, and talent on demand.

Patrick Collison turned Stripe into the intellectual hub of tech — through essays, open source learning, and ideas.

The founders with distribution are winning everywhere:

• Faster sales cycles, higher ACVs
• Inbound pipeline, not chasing demos
• Category authority vs vendor energy
• Better talent, investors, & partnerships
• Demand that compounds instead of resets every quarter

This is no longer a “content strategy.” It’s an unfair advantage

And right now?

Most B2B founders are sitting on the sidelines waiting for:

❌ The "right" time (it was 2 years ago)
❌ More clarity (it comes from action, not waiting)
❌ Confidence (built by publishing, not planning)

In 12-24 months, B2B will be saturated with founder-creators.

The 1% publishing today are capturing the hearts, minds and wallets of their customers. 

What are you waiting for?

Helping recruiting agency owners get new clients with done-for-you LinkedIn content | Podcast host at Founder-Led

Most CEOs think pipeline is built in their CRM.

It’s not.

Right now, somewhere, your future buyer is listening to a podcast where your competitor gets mentioned. Another is reading a LinkedIn post that positions someone else as the category leader. A third is in a Slack community asking for recommendations — and your name isn’t coming up.

None of this shows up in your attribution dashboard.

This is what Chris Walker and others call the 'dark funnel' — the invisible network of conversations, content, and word-of-mouth that actually drives 60–80% of B2B buying decisions.

Here’s what few people understand 👇

B2B buyers don’t discover you through:

 • Gated eBooks
 • Paid search
 • SDR outreach

They discover you in places attribution software can’t see:

 • Podcasts
 • Founder content on LinkedIn
 • Niche industry communities
 • Private group chats
 • Word-of-mouth between peers
 • “Here’s how we use XYZ tool” Zoom conversations

Buyers are learning from your content and from each other.

They already know:
 • How your product works
 • Where it fits in their stack
 • The aha-moment use cases
 • The lift you deliver

Before they ever speak to you.

The dark funnel isn’t small — it’s where 70–90% of the buying journey now happens.

And because founders can’t measure it… they don’t invest in it.

78% of executive buying decisions now involve online research before the first sales call.

Companies leaning into dark-funnel channels are seeing 50–67% shorter sales cycles.

But most executives hold back because:

 • It can’t be measured like traditional channels
 • It requires creativity — more art than science
 • It feels risky because it's a new paradigm

And that’s the opportunity.

You’re not competing on product anymore. You’re competing on who educated the buyer first.

The dark funnel isn’t new — it’s how consumers have been buying for decades.

What’s new is that it’s now where the majority of B2B buying decisions start.

And if you’re not showing up where it counts, you’re not in the consideration set.

--

If this resonates and you want to start winning inside this new paradigm, DM me and I’ll send you the playbook we’ve developed after working with 40+ businesses.

It takes 2 hours per week and compounds faster than any other marketing channel when done right.

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

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

No alternative text description for this image

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!

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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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