Sitting Uncomfortably with James Connelly

Wow. What a first season. When we started Sitting Uncomfortably, the idea was pretty simple: sit down with brilliant people and get beyond the polished version of success. One season later, we’ve talked about the wins, the failures, the decisions that changed everything, the moments nobody saw and plenty of things our guests probably weren’t expecting James to ask. More than anything, these conversations have been a reminder that there’s always a human behind the success. And that’s exactly why James loves doing this: meeting interesting people, asking the questions he genuinely wants the answers to, and learning something along the way. So, for our final episode of Season One, we’re looking back at some of our favourite moments. Who Said It? James is confronted with some of the best quotes from the season. The only catch? He has to remember who actually said them. The Sitting Uncomfortably Awards We hand out the completely unofficial, highly coveted awards of Season One. And, inevitably, we get distracted reminiscing about everything that happened along the way. Thank you to every guest who sat uncomfortably with us, and to everyone who watched, listened, shared a clip, sent it to a mate or followed along with Season One. We’ve had an incredible time making it. Season Two is coming. And we’re only getting started.

Vishal Amin founded UNTIL, the wellness members club growing fast enough to pull Steven Bartlett on board as an investor. His premise: wellness deserves the same intentionality as any other part of business.He didn't take the obvious route to get there. A childhood side-hustle that earned him the label "an effective drug dealer." A stint at McKinsey. A healthcare startup he scaled to a sale to Goldman Sachs, years before UNTIL existed.But this conversation isn't about the business. It's about ambition, setbacks, and what it actually feels like once you get the thing you thought you wanted.Vish on:🧠 The idea behind UNTIL and the moment he knew it would work🧠 Building with Steven Bartlett, and who he really is as an investor🧠 Success, setbacks, and what "making it" actually feels like🧠 Wellness and longevity; what works, and what just sellsVishal Amin is Sitting Uncomfortably. Produced by Charlie Oscar's Creative Studio.

Caspar Rose built Fresh Fitness Food into the UK's top-rated and most-loved meal prep brand, growing it from scratch into a business trusted by professional athletes and everyday people alike, before selling to Calo. But his path there wasn't a straight line: from washing dishes while his friends were away at university, to working in some of the most brutal kitchens in the industry, to spending time helping the UK prison system. Caspar's journey to building something of his own was anything but conventional. But this conversation isn't just about building a business. It's about self-doubt, discipline, and what it actually takes to reach your ceiling, physically, mentally, and in business.Caspar shares: 🍽️ What lengths he goes to in order to reach his potential 🍽️ Working in some of the industry's most brutal kitchens, including for Gordon Ramsay 🍽️ Nutrition, health hacks, and the routine behind performing at his best Caspar Rose is Sitting Uncomfortably. Full episode available now on all platforms. Produced by Charlie Oscar's Creative Studio.

Carly Natalizia is Chief Commercial Officer at Gymshark, having built her career through senior marketing roles at some of the UK's biggest brands, including CMO at The Very Group and Marketing Director at Virgin Money.
But this conversation isn't just about marketing.It's about navigating self-doubt, leading with empathy, balancing ambition with family, and building a career without losing yourself along the way.
Carly shares:
🧡 Building a career across some of the UK's biggest brands🧡 Leadership, disagreement and working alongside Ben Francis🧡 Motherhood, ambition and holding your boundaries🧡 The reality behind confidence and self-doubt🧡 How Gymshark helped shape modern influencer marketingCarly Natalizia is Sitting Uncomfortably.Full episode available now on all platforms.Produced by Charlie Oscar's Creative Studio.

Steve Sidwell played over 500 professional games, won the Premier League with Chelsea, and has become one of football's most respected broadcasters and podcasters.But this conversation isn't just about football.It's about staying grounded, leading by example, navigating life after sport, and building a meaningful second chapter.Steve shares:⚽️ The standards behind a long career at the top⚽️ Life after football⚽️ Leadership, family and loyalty⚽️ Why humility remains his greatest strengthSteve Sidwell is Sitting Uncomfortably.Full episode available now on all platforms.Produced by Charlie Oscar's Creative Studio.