In this special episode, James Potter and Ian Anson swap seats and become the guests. 

Expertly hosted by Sophie Roberts (The Insurer TV), they unpack how Rokstone grew from a feral startup vibe to a professional, high-performance business breaking $1bn GWP — without losing the underdog edge. 

It’s a transparent look at conviction, ownership, and building teams that say “yes” and figure out the how. Expect stories from the early days, lessons learned scaling fast, why culture is a living thing, and what the industry needs to let go of to move faster.

Listen as we discuss…

(00:02:44) The “Virtual Lunch” idea

(00:05:30) Why bring in voices beyond insurance (and making it interesting)

(00:06:25) Ownership as a theme: partnering with founders to build businesses

(00:08:17) Behind the scenes: chaos, first-episode nerves, and studio setup

(00:10:36) How they got here: Ian’s path from sports dreams to insurance

(00:14:03) James’s entry into underwriting

(00:15:54) Founding Rokstone: frustration, market gap, and betting on underwriting

(00:20:09) Risk appetite: mortgage worries, hustle mindset, and underdog fuel

(00:26:00) Less than 10 years to $1bn GWP - what big, hairy, audacious goals look like

(00:26:42) Why Ian joined: energy, scrappy culture, and fighting the MGA bias

(00:36:40) Rapid growth consequences: from feral to professional (with data)

(00:39:08) Fail fast, improve daily - the momentum of marginal gains

(00:43:13) Keeping culture at scale: ownership, no passengers, say “yes” first

(00:46:18) Hiring, failing fast, and building culture

(00:56:39) Leadership lessons: hold on too long / surround yourself with challengers

(00:59:47) What to drop and what to build: inertia out; clarity, talent, and tech in

(01:05:49) Advice to younger selves: don’t wait for perfect; confidence + instinct

(01:08:50) The lunch question…

KEY INSIGHTS

Ownership isn’t a slogan - it’s a behaviour: fix the roof, then optimise it.

Speed scales when paired with structure: say “yes,” then build the how.

Culture is living: protect the underdog mindset as you professionalize.

Fail fast, learn faster: momentum compounds when you improve daily.

The industry’s drag factor is inertia; clarity (wordings), talent, and tech win next.

GUESTS

James Potter, Chairman, Rokstone

Ian Anson, Global CEO, Rokstone

Guest interviewer: Sophie Roberts, The Insurer TV

Hasani Jess, Group CTO at Aventum, joins James and Ian to talk about what it really takes to build technology that works in the real world.

This isn’t a conversation about buzzwords. It’s about engineering empathy into systems, designing platforms that simplify complexity, and leading people through the messy reality of change.

In his role as the architect of Atomx – Aventum’s proprietary tech suite – Hasani is spearheading one of the largest tech transformations in the London insurance market. In this episode, he opens up about what makes great technology actually useful, why most AI implementations fail, and how to bring people with you when everything is changing.

From early beginnings with a typewriter in Hackney to running a 140-person tech team, Hasani shares deep insight into culture, leadership, and the power of integrity when building at scale.

Listen as we discuss…

(02:11) Early career and falling in love with tech

(08:42) What he walked into at Aventum – and what excited him

(10:48) Building Atomx from scratch – and why it had to be end-to-end

(14:00) Modernising underwriting without alienating people

(17:12) How to do change management well 

(18:07) The real opportunity: distribution, not just efficiency

(21:00) Turning submission data into portfolio insight

(23:00) Why email is still the MVP - and how they made it work

(25:11) Apple-inspired design for a complex world

(27:06) What UX errors reveal - and how to fix them

(28:08) The AI hype cycle - and why chatbots aren’t the answer

(30:00) Real AI impact comes from workflow integration

(33:04) How to future-proof your architecture

(36:00) What great looks like in 5 years: tripling growth, scaling clients

(39:27) Leading people through tech change with empathy

(44:00) Culture non-negotiables: trust, integrity, and representation

(47:07) Why they deliberately hired non-insurance people

(48:17) Visual transformation: why wireframes beat Word docs

(52:00) Final reflections on self-awareness and what he’d tell his day-one self

(55:00) Hasani’s dream lunch guest and where they’d go

KEY INSIGHTS

Good tech isn’t built in isolation – it’s built with empathy

Most transformation fails because people weren’t brought with it

If you want people to change, start by earning their trust

Efficiency isn’t the end goal – growth is

AI only works when it’s part of the workflow, not stuck on top of it
GUEST

Hasani Jess, Group CTO, Aventum

Follow Hasani on LinkedIn

Whether you're in insurance or not, this is a story about leadership under pressure, disciplined decision-making, and the mindset it takes to bet on yourself.

Jordan Lanford, Global Head of Aviation at Rokstone, joins James and Ian to talk about risk, speed, and rebuilding a legacy-dominated market from a blank slate.

From pilot school to global leadership, Jordan shares how his team is reshaping aviation underwriting through deep technical conviction, smarter tools, and an ownership mindset.

This episode dives into what happens when you stop waiting for innovation and start building it yourself - revealing why clarity, culture, and trust matter more than bureaucracy when the pressure’s on.

Listen as we discuss…

(00:00) From childhood obsession with flight to pilot school

(01:34) 9/11, furlough, and the unexpected pivot into insurance

(03:27) Aviation underwriting in plain English

(04:31) Are planes really becoming less safe? Jordan sets the record straight

(05:18) Building an aviation business from a blank slate

(06:39) What large-carrier experience taught his team

(07:45) The moment he knew Rokstone’s approach was different

(08:31) Tech that “doesn’t exist yet” - and why timing matters

(10:21) Why big carriers struggle to innovate

(11:20) What underwriting discipline actually looks like

(13:25) Becoming a business owner - autonomy, risk, and responsibility

(15:54) How MGAs have evolved - and where Rokstone fits

(17:48) Flipping the 70/30 rule: admin vs. value creation

(20:23) Risk-taking, adrenaline, and big decisions

(23:31) Building a high‑performance team with different strengths

(26:05) Aviation voices at global industry tables - why it matters

(33:57) The advice he’d give his younger self

(36:30) His dream lunch guest…

KEY INSIGHTS

Innovation needs autonomy: speed requires trust and decision-making at the edge

High-performing teams thrive on diversity of background, not uniformity

Underwriting discipline means doing the right thing - even when no one’s watching

Legacy systems slow you down - building fresh lets you unlock new value

Ownership shifts how you think: about risk, about leadership, and about people

GUEST

Jordan Lanford: Global Head of Aviation, Rokstone

Follow Rokstone on LinkedIn

Learn more about Rokstone Aviation

Jamie McDonald - known around the world as Adventureman - joins James and Ian to talk about the mindset behind extreme endurance, redefining risk, and turning pain into purpose.

From spending years in hospital as a child with a rare immune disorder to running 200 marathons across Canada dressed as a superhero, Jamie’s story is one of courage, humour, and heart.

He opens up about childhood trauma, rediscovering meaning through adventure, and why embracing discomfort is the only way to grow - in life, leadership, and business.

Now a bestselling author, motivational speaker, and founder of the Superhero Foundation and Ward Buddies, Jamie has raised millions for sick children around the world. His mission is simple: help people keep going when it hurts.

Listen as we discuss…

(09:12) Becoming Adventureman – how one £50 bike changed his life

(13:00) From childhood illness to strength – turning trauma into fuel

(16:39) The £20,000 decision that led to 14,000 miles across the world

(19:00) Why naivety beats overplanning every time

(22:03) Building belief: the difference between planners and doers

(25:54) The Canada run, breaking point, and what he learned from strangers

(31:11) Money, trust, and finding hope in small acts of kindness

(33:48) The family in Tajikistan who changed his view on gratitude

(38:20) Why purpose matters more than success – and how giving back keeps you grounded

(43:19) Childhood trauma, therapy, and creating Ward Buddies

(46:10) Redefining fear – why it’s okay to feel it, and what matters after

(51:09) Pain, birth, and why we need discomfort to feel alive

(54:45) The treadmill world record and the science of endurance

(1:00:10) What keeps him going when everything hurts

(1:02:26) The letter that changed everything – running for something bigger than himself

(1:03:47) Legacy, purpose, and what really matters at the end

(1:07:06) Goal setting, crumbs vs. cake, and why fulfillment lives in the journey

KEY INSIGHTS

Pain and discomfort are gateways to growth

Naivety is a superpower: start before you’re ready

Gratitude comes from perspective, not possessions

Purpose beyond yourself sustains you when motivation fades

Real strength is learning to keep going when it hurts most

GUEST

Jamie McDonald (Adventureman): Endurance Athlete, Author, Motivational Speaker, and Founder of Ward Buddies

Follow Jamie on Instagram

Donate to Ward Buddies

Kevin Fisher, President at IQUW and former Global Chair at Guy Carpenter, joins James and Ian to reflect on four decades at the top of the (re)insurance industry, what real leadership looks like when the market, technology, and talent keep changing.

From starting as a 16-year-old claims clerk to running one of the world’s leading reinsurance brokers, Kevin shares lessons learned over 45 years of building teams, backing people, and leading through change.

He talks about imposter syndrome, loyalty, and why “it’s okay not to know,” explores the evolution of the London Market from the 1980s to AI, and explains why integrity, curiosity, and human connection still sit at the heart of everything.

Listen as we discuss…

(02:24) From school leaver to insurance - how sport shaped his view on people and performance

(07:13) What the industry gave him - friendships, learning and the trade-offs of success

(13:56) Why we’re losing real talent through over-automation

(17:15) What makes a great team - diversity, difference and shared accountability

(20:08) The leaders who shaped him and what they taught him about trust

(26:02) Loyalty, money, and why job-hopping isn’t always progress

(29:30) Imposter syndrome and learning to lead with honesty

(33:35) What reinsurance actually does - and why it underpins the global economy

(41:00) The role of brokers and how capital cycles ripple through the market

(53:11) The shift from broking to underwriting and what surprised him most

(58:00) AI’s impact - opportunity, risk, and the future of underwriting talent

(1:03:00) Big Tech, brand trust, and whether they’ll ever enter the market

(1:07:18) Algorithmic underwriting and the next 10 years of risk

(1:12:02) What keeps him grounded, who he’d lunch with, and the one piece of advice he’d give his younger self

KEY INSIGHTS

Leadership starts with listening, not knowing everything

Integrity and curiosity build careers that last

The right people matter more than perfect process

AI will change the pace, not the purpose, of underwriting

Reinsurance is the hidden engine of the global economy

GUEST

Kevin Fisher, President, IQUW

Follow Kevin on LinkedIn

Ex-Premier League footballer Henri Lansbury (Arsenal academy, Luton Town promotion) joins James and Ian to talk about moving from elite sport to entrepreneurship. Building Grass Gains - the organic lawn and plant nutrition brand now stocked in 400+ garden centres.

Henri shares how a lockdown question sparked a product, why he’s taking a “pro-grade for retail” approach, and what leadership lessons from Arsenal (hello, Patrick Vieira) look like inside a fast-growing startup. 

We cover ownership mindset, pressure, routine, fundraising, and the power of talking openly about health - including his 2016 testicular cancer story and why these conversations can save lives.

Listen as we discuss…

(03:46) From player to founder: the Grass Gains origin story

(06:48) From home trials to 400+ garden centres - and supplying pitches like the Emirates

(13:56) Pressure, performance, and channelling it at work

(15:17) How to do marketing differently in a stale category

(16:25) Building team culture: fun, standards, and clear goals

(18:05) On role models, service, and treating people right

(19:24) Playing while building and knowing when to step back

(21:20) How to take ownership and accountability when the buck stops with you

(26:45) Life after sport: routine, purpose, and why golf became the new “training”

(30:37) How to trust the team you’re going into business battle with

(34:13) Raising, investors, and why alignment matters

(35:23) The biggest risk he’s taken… and the one he didn’t

(38:13) Mental health, masculinity, and talking about testicular cancer

(42:44) What he’d tell his younger self

(45:00) His dream lunch guest, location, and his order!

KEY INSIGHTS

Product-market spark: solve a real home problem with pro-grade quality, made simple

Leadership travels: standards, aura, and trust from the dressing room to the boardroom

Culture beats category: playful, modern marketing wins in “old” industries

Ownership raises the game: accountability, communication, and aligned investors

Talk about it: openness on health and mindset lifts people and performance

GUEST

Henri Lansbury - Co-Founder, Grass Gains (ex-professional footballer)

Follow Henri on Instagram
Shop Grass Gains

Larry Burrows, Head of US Casualty at Rokstone, joins James and Ian to talk about taking the leap from balance-sheet comfort to business ownership - and what it really takes to build something from the ground up.

From failing computer science at university to leading one of Rokstone’s fastest-growing portfolios, Larry opens up about self-belief, innovation, and redefining what it means to be an underwriter in a fast-changing market.

He shares how his team is using AI and automation to reshape underwriting, why ownership has changed everything about his motivation, and what the next decade of (re)insurance could look like.

Listen as we discuss…

(03:05) How Larry fell into insurance and found his niche in US casualty

(05:09) What failure taught him about resilience and self-starting

(12:00) Why he chose to leave a big balance-sheet carrier for an entrepreneurial model

(15:01) The mindset shift of becoming a business owner

(17:24) Building a high-performing team and culture from scratch

(20:02) Using AI and automation to turn unstructured data into underwriting intelligence

(26:14) Automation, productivity and how tech is changing day-to-day underwriting

(29:14) Why he chose Rokstone, and what surprised him about the culture

(38:00) The future of the MGA model and AI’s impact on the industry

(41:22) Advice for underwriters thinking about starting their own business

(46:12) The risk he took that changed everything

KEY INSIGHTS

Why ownership is the ultimate motivator

The evolution of MGAs and what’s driving their rise

How AI is reshaping underwriting precision and decision-making

Why culture, trust and autonomy drive better results

What it means to take a leap and back yourself

GUEST

Larry Burrows, Head of US Casualty, Rokstone

Follow Larry on LinkedIn

Lucy Clarke, President of Risk & Broking at WTW, joins James and Ian for a refreshingly honest conversation on falling into insurance, finding your feet, and leading with conviction.

From her start as a secretary in Houston to becoming one of the most influential women in the global (re)insurance market, Lucy opens up about what shaped her leadership, how risk and resilience show up in real life, and why we need to stop hiding behind jargon.

Listen as we discuss…

(01:14) How Lucy fell into insurance  

(07:38) What attracted Lucy to the energy market and how that path helped shape her approach to leadership 

(10:51) Leadership lessons from JLT and early role models  

(14:03) How to embrace new opportunities whilst overcoming imposter syndrome  

(20:28) Authentic leadership and ditching the jargon  

(23:40) What Lucy would tell her younger self  

(26:53) The new era of WTW and Greenfield reinsurance  

(30:05) Culture, resilience and what attracted her to WTW

(33:18) The transformation of the MGA landscape and how Rokstone is setting a new standard

(36:30) Looking ahead: AI, digital transformation, and the next 10 years  

(39:42) Work-life balance, motherhood, and being a woman in leadership  

KEY INSIGHTS

Falling into a career you grow to love

What the energy market taught her about scale and precision

Why the best leaders don’t pretend to know everything

How to balance work, leadership, and family without burnout

What the rise of MGAs and AI really mean for the future of broking

GUEST

Lucy Clarke, President Risk & Broking at WTW
Follow Lucy on LinkedIn

Pull up a chair and join Rokstone Chairman James Potter and Global CEO Ian Anson for lunch with some of the biggest and boldest minds in and beyond (re)insurance.

From athletes and entrepreneurs to underwriters and industry challengers, you’ll hear candid conversations about what it really takes to lead.

These aren’t boardroom soundbites - they’re real stories of risk, conviction, and the mindset behind bold decisions.

New episodes drop weekly. Same time, same table. This is Virtual Lunch.

Available wherever you get your podcasts.