Virtual Lunch

How to Grow Fast Without Losing Control with Nadine Kearney

Rokstone’s Chief Underwriting & Risk Officer, Nadine Kearney, joins James and Ian to talk about underwriting, governance and what it really takes to build a business that can grow quickly without losing control. From starting out in claims in Canada to leading underwriting and risk at Rokstone, Nadine reflects on the career path that shaped her, the lessons she took from great leaders, and why no decision in insurance ever sits in isolation. She talks through the difference between big corporate insurance and Rokstone’s more entrepreneurial model, how strong frameworks can empower underwriters rather than restrict them, and why Rokstone now looks more like a virtual insurer than a traditional MGA. This is a conversation about portfolio thinking, technology, accountability, and modern leadership inside a fast-moving underwriting business. Listen as we discuss… (01:00) Why Nadine deliberately chose insurance (02:00) Starting out in claims in Canada and the early career path that shaped her (04:30) The leaders she learned from and what she chose to take forward (06:00) What her role at Rokstone actually is and how she thinks about sustainable, profitable results (07:30) Why no underwriting decision sits in isolation (08:30) The difference between big corporate insurance and Rokstone’s entrepreneurial model (10:00) How governance should enable growth rather than block it (12:00) The healthy tension between central oversight and empowered underwriters (15:00) Why Rokstone now looks more like a virtual insurer than a traditional MGA (16:30) How portfolio optimisation builds confidence with capital providers (18:00) Atomx, dynamic portfolio management and real-time decision-making (20:00) What should and shouldn’t be automated in underwriting (22:00) What the next generation of underwriters will need to thrive (25:00) Winning trust and respect in a leadership role (29:00) Ownership, accountability and what happens when portfolios go wrong (33:00) Why Rokstone’s ownership model creates real alignment (35:00) Returning from maternity leave into a bigger leadership role (39:00) What changes when your time becomes your scarcest resource (43:00) What she’d tell herself on day one (45:00) Who she’d take to lunch, and where they’d go KEY INSIGHTS Great underwriting needs frameworks that empower people, not block them No underwriting decision sits in isolation - every call affects the wider portfolio Technology should remove noise, not replace judgement Healthy tension creates better decisions when trust and accountability are in place Leadership is often about listening, creating clarity and helping others perform at their best GUEST Nadine Kearney- Chief Underwriting and Risk Officer, Rokstone

Composure at 200mph - Leadership, Focus and Life in Formula One with Ollie Bearman

Ollie Bearman joins James and Ian to talk about pressure, performance and growing up fast inside one of the most demanding environments in sport. From karting at Rye House with his dad to stepping into a Ferrari Formula One car, Ollie reflects on the moments that shifted racing from passion to profession, the reality of being signed to the Ferrari Driver Academy, and what it actually feels like to make your F1 debut under global scrutiny. He opens up about leadership inside the garage, emotional control at 200mph, the mental load of modern Formula One, and why fear isn’t something he feels in the car but something he’s deeply motivated by outside it. This is a thoughtful, grounded look at elite performance, maturity under pressure, and what it takes to keep improving when the margins are measured in tenths. Listen as we discuss… (01:00) When racing stopped being a hobby and became a career (02:45) The Ferrari Driver Academy moment that changed everything (04:40) Confidence, belief and questioning yourself as a young driver (05:55) Role models, work ethic and lessons learned from his father (07:10) Leadership in Formula One and setting the tone inside the garage (09:25) Becoming the “best sensor in the car” and earning engineering trust (11:00) Getting the call from Ferrari and the reality of academy life (16:25) Driving a Ferrari F1 car for the first time at Fiorano (18:50) Composure, emotion and decision-making at extreme speed (24:50) The Jeddah call-up and making an F1 debut with no preparation (28:20) Media pressure, attention and staying mentally clear (33:00) Finding flow, rhythm and peak performance in the car (38:00) Rookie mistakes and learning fast (45:00) Fear, failure and the motivation to avoid regret (59:20) What great looks like five years from now (01:07:20) Advice to his younger self and learning to savour the moment KEY INSIGHTS Pressure sharpens performance when you learn to manage capacity Leadership starts with respect for the whole team, especially those behind the scenes Confidence grows through preparation, not ego Fear isn’t always danger but the risk of wasted potential Elite performance is built on small, repeatable decisions GUEST Ollie Bearman [https://www.instagram.com/olliebearman/] Formula One Driver

How Rokstone Won - the Work Behind Achieving $1bn with James, Ian, and Sophie Roberts

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

Why Insurance Tech Has Failed (And What Comes Next) with Hasani Jess

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 [https://www.linkedin.com/in/hasani-jess/]

Why Fast Underwriters Win: Aviation, Ownership and Discipline with Jordan Lanford

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 [https://www.linkedin.com/company/rokstone-underwriting/posts/?feedView=all] Learn more about Rokstone Aviation [https://rokstoneuw.com/aviation]