Running OffScript with Calypso Rose and Guest Features Max Fosh, William Hanson, Reese Wong and Charlotte Liebling

Annie Wenmiao Yu (00:00)
Hello everyone, it's Annie, and welcome back to the Low to Grow podcast. Today I have something a little different for you — a bonus episode. Over the weekend, I packed up my mic and headed to South Kensington to attend the very first Offscript Generation Summit. This is a brand-new gathering that’s neither a careers fair nor a traditional networking event. Instead, it's a curated space for 16 to 25-year-olds who don’t want to follow a linear, well-trodden career rulebook. It’s for the creatives, coders, thinkers, doers — all eager to learn from people who carved their own path and proved that a well-lived life doesn't have to be linear.

My main mission was to interview Calypso Rose, one of the brilliant founders of the Offscript Summit and a serial entrepreneur, to understand why creating this third venture is socially meaningful and why something like the Offscript Generation is so needed in 2026. Over the course of the day, I also spoke with several inspiring speakers, such as YouTuber Max Fosh on how he broke into YouTube when the platform was already crowded.

Max Fosh (01:27)
For me, building mental resilience as a creator is about understanding that not everything you make will perform well, and divorcing the effort you put in from the outcome — because the outcome is often out of your control. As long as you're making things you genuinely enjoy, that’s what matters most. I’ve always said the most important viewer you have is yourself. If you’re happy with your content, the right audience will find you.

For better mental health, communication and having a core group of people you love and trust is crucial — friends, family, anyone you can genuinely talk to. Moving your body always helps too. I’m also incredibly grateful to have close friendships that give me real grounding. So for me it’s friendship, communication, and getting outside for a run.

What makes the Summit special is seeing so many passionate young people eager to learn about different subjects and industries. If I can impart even a small piece of wisdom to them, I’m honoured to be part of it.

Annie Wenmiao Yu (02:35)
I then found the courage — and hopefully the good manners — to ask William Hanson, the British etiquette coach, why he believes that minding your manners will serve young people well in today’s job market.

William Hanson (02:47)
Building mental resilience can be difficult, especially online. The digital world is democratic: everyone can share their thoughts and opinions, even when those comments are abrasive or bigoted. That’s part and parcel of free speech. One thing that helps me is simply not reading the comments and not taking things too seriously.

For better mental health, we need to prioritise interacting with people rather than relying entirely on devices. Phones and laptops are useful and essential, but they should complement human interaction, not replace it. Developing people skills, focusing on real human contact — this boosts confidence and improves mental health.

The Summit is special because it’s a chance to connect with the next generation as they step into the workplace. It allows me to talk about something that isn’t discussed enough — treating others with respect, civility, charm, and grace. You only have to glance at the news to see how much we need that right now.

Annie Wenmiao Yu (04:08)
I also connected with fellow female entrepreneur Charlotte Liebling, also known as the Fluffy CEO, about building a social-impact company that has already partnered with Bloomingdale’s and Selfridges.

Charlotte Liebling (04:22)
As a female entrepreneur, building resilience has been something I’ve had to learn quickly. For me, it’s been about accepting that doubt, failure, and even profile-related hate will always be part of the journey. That energy sits with you, but I’ve learned to turn it into rocket fuel — not something that pushes me down, but something that helps lift me into who I know I can be.

For better mental health, I think we need to invest more time in imagining the positive. It's easy to get swept up in negative news and catastrophising, but we rarely allow ourselves to envision the possibilities of good things happening. Whatever the opposite of catastrophizing is — that needs to become a habit.

This Summit is special because there was nothing like it when I was young. There are career fairs for people who already have a sense of where they're headed, but for those following non-linear paths, there’s so little that celebrates and empowers them. This event feels magical for that reason.

Annie Wenmiao Yu (06:00)
On my way around, I surprisingly ran into a previous Low to Grow guest, Reese Wong — a Diana Award winner and recent graduate who was leading a workshop on personal branding.

Reese Wong (06:14)
Offscript stood out to me instantly because first, it brings young people together with their parents — and so few events do that. Second, it’s incredibly needed. We’re moving into a world where careers are non-linear and young people need to embrace entrepreneurship. This event hits all those marks. I’ve been speaking with parents and their kids all day; it’s been great.

With so much uncertainty right now, young people need to think about their careers, yes — but also about protecting their mental health and safeguarding their wellbeing. Go out, be entrepreneurial, take initiative, but also know when you’re pushing yourself too far and avoid burnout.

Annie Wenmiao Yu (07:09)
Every speaker, organiser, and entrepreneur I met brought something real and grounded to the Summit. It truly is something I wish I’d been able to attend as a teenager. Now, here’s your exclusive behind-the-scenes conversation with Calypso Rose — the powerhouse behind the Offscript Generation Summit. Let's dive in.

Annie Wenmiao Yu (07:33)
Calypso, who do you want to be listening to this podcast?

Calypso Rose (07:38)
After this event, we’ve gathered all this incredible content, and instead of just putting it on YouTube, we’re creating an educational library for schools, career leads, and universities. I’d love them to get in touch so we can share access. We didn’t want the content getting lost in YouTube algorithms — we want it used intentionally.

Annie Wenmiao Yu (08:07)
It’s great to be here. So where did your story start?

Calypso Rose (08:10)
This is my third business. I’m a serial entrepreneur and sold my previous company about six months ago. My co-founder, John Ford Gordon, came to me and said careers fairs simply aren’t doing the job anymore — the world is changing, and people need to explore what the future looks like now, not what it looked like ten years ago. Together we came up with Offscript: a Summit featuring big-name thinkers and workshops on the future of work, AI, and more.

Annie Wenmiao Yu (08:38)
Today is the first day of the Summit. How’s it going?

Calypso Rose (08:45)
It’s been fantastic. The insights we’re getting from young people who’ve seen speakers like Ali Eslami and Max Fosh are incredible. It’s our first time running this, so it’s been slightly chaotic — but it’s all coming together beautifully.

Annie Wenmiao Yu (09:01)
What’s the most meaningful part of organising this event?

Calypso Rose (09:07)
It’s the outcomes for the young adults. Even if only a handful leave with clarity on their next steps — whether that’s starting a business, pivoting away from a big tech dream, or realising they want to do something on their own — that’s what matters. We’re doing this because we truly believe in helping people find their direction.

Annie Wenmiao Yu (09:40)
Earlier, I attended a talk by the Editor-in-Chief of The Observer on AI and how young people can adapt. What struck me was seeing parents and children together — that’s so rare.

Calypso Rose (10:00)
Exactly. Parents are feeling lost too. Many default to saying “Go to university, do what I did,” but hearing these talks opens up new possibilities. There are apprenticeships, side hustles, entrepreneurial paths — and parents seeing this alongside their children is powerful.

Annie Wenmiao Yu (10:28)
Was entrepreneurship something you pursued while studying?

Calypso Rose (10:32)
Not quite — I went to about three different universities for about two weeks each. I tried PR and marketing but felt too young to work full-time, went back to university, got overwhelmed, and dropped out. At 21, I started my first business — a product company I ran for ten years. It sold across the world, from Japan to becoming a Christmas bestseller in Selfridges.

Annie Wenmiao Yu (11:04)
How did it feel at 21 to create that first success?

Calypso Rose (11:12)
I loved the adventure. I don’t know how much money I made — most of it went into stock and paying everyone else — but the opportunities were incredible. I learned so much. After licensing that business, I started The Indytute, because by then I felt unemployable after years of working for myself. If I could redo my first business, I would have found a mentor and a finance director early on.

Annie Wenmiao Yu (12:01)
Were you handling everything yourself?

Calypso Rose (12:03)
Pretty much. I was young and successful quickly, so part of me didn’t think I needed advice. Now I know I absolutely did. I’d tell my younger self to seek guidance from someone who understood my industry and could look at my books with insight.

Annie Wenmiao Yu (12:25)
How do you feel you’ve changed as a business owner and female entrepreneur since then?

Calypso Rose (12:36)
At 21, I wanted to be a millionaire. My second business was about creating a more balanced lifestyle. Offscript is about purpose. I want to support the journeys of the young people we help, from start to finish, and build something with real longevity.

Annie Wenmiao Yu (13:06)
Why are in-person events still important in such a digital age?

Calypso Rose (13:23)
Because real connections are memorable. You’re not just being scrolled past. Events like this allow you to ask speakers questions and realise you’re not alone. LinkedIn, for me, is like everyone else’s Instagram — it gives me FOMO and makes me feel I'm not doing enough. But when you’re in a room with people, you see how much you actually are doing.

Annie Wenmiao Yu (13:59)
How has young people’s definition of success changed?

Calypso Rose (14:08)
Young people today want balance. They’ve seen burnout firsthand and don’t want it. They want to stay healthy, see their friends, and build something meaningful — very different from my generation.

Annie Wenmiao Yu (14:28)
In the age of AI, what’s one thing young people can do to equip themselves?

Calypso Rose (14:37)
Just start. Use tools like Lovable, build something, and put it on your CV. Solve a small problem in your life. Create an app, build a brand with ChatGPT, make lots of mini-projects. These micro-skills will make you invaluable in your next job.

Annie Wenmiao Yu (15:10)
What’s one challenging moment that shaped you?

Calypso Rose (15:21)
The pandemic. I had an experience-based business and lost all revenue overnight. We pivoted to at-home experiences. During that time, I also fell off my bike and broke my jaw — it was wired shut for lockdown, so I could only drink soup. With a three-year-old at home, it was tough. But I learned how resilient I am. In business, setbacks feel catastrophic, but you come out the other side stronger. Now when things go wrong, I remind myself it will be fine.

Annie Wenmiao Yu (16:43)
That’s such an entrepreneur’s mindset. How do you teach resilience?

Calypso Rose (16:52)
I tell my son it doesn’t matter if things go wrong — just keep trying. He’s nine and already an amazing little salesman. When he sells at markets and gets rejected, he just says “Next!” That thick skin is so important. You need to be able to ask without taking “no” personally. If you can relate to people, listen, and remember their names, that’s a superpower.

Annie Wenmiao Yu (18:00)
Do you experience imposter syndrome?

Calypso Rose (18:05)
Not really. It wasn’t a concept when I was younger. I just get on with things. Do you get imposter syndrome?

Annie Wenmiao Yu (18:18)
For me, imposter syndrome means I’m in the right place — pushing myself outside my comfort zone. It shows I’m doing something new, uncertain, and challenging, which is often exactly where I need to be.

Calypso Rose (18:41)
Exactly. When things go wrong or you have to push yourself to learn something new, I get excited. During the pandemic, even in the chaos of pivoting the business, I loved the challenge. When things are too easy, I get bored.

Annie Wenmiao Yu (19:06)
Running an event at this scale must come with pressure. How did you handle the anxiety?

Calypso Rose (19:23)
The anxiety hit two weeks ago — wondering whether we’d sold enough tickets, or reached enough schools and community groups. Last night was surprisingly calm — the calm before the storm.

Annie Wenmiao Yu (19:45)
As you start this new venture, how is your mindset different from when you were 21?

Calypso Rose (19:55)
With Offscript, I have a bigger team. It’s amazing to have people to bounce ideas off — but I’ve had to adjust, because I’m used to making decisions alone. Now I pause, consult the team, and move together. It makes everything better.

Annie Wenmiao Yu (20:10)
How did you meet your partners and know they were the right people?

Calypso Rose (20:36)
I worked with John Gordon in my previous business — he’s wonderful. I go a lot by instinct. You need good rapport and complementary skills. Our investor, Mehdi, is empathetic, open, and instantly inspiring. I knew I wanted to work with them.

Annie Wenmiao Yu (21:03)
What is one thing you believe will allow more people to have better mental health?

Calypso Rose (21:11)
Make time for yourself and exercise. Go for a run, get outside, look up, appreciate the world.

Annie Wenmiao Yu (21:19)
Wonderful. Thank you for coming on the Low to Grow podcast.

Calypso Rose (21:22)
Thank you.