Alex Packham knows what it’s like to have everything change in a single day, and nothing changes at all. From selling ContentCal to Adobe from his spare bedroom in the middle of lockdown to waking up the next morning wondering who he was without the business, Alex’s journey blends adrenaline highs with the quieter, harder work of rebuilding identity.

In this episode, he opens up about the reality of sudden wealth, the role of luck in big wins, and why mental health matters just as much as the deal itself. Alex shares the behind-the-scenes strategies that helped a small team “punch above their weight,” the lessons he’s bringing from Silicon Valley back to the UK, and how letting go of ego has reshaped his approach to life and work.

It’s a candid look at ambition, adaptation, and what happens after you’ve reached the milestone you spent years chasing.

Partners:

IFS - award-winning Asset & Service Management software

👉 Reimagine your operations at: https://highpfrmc.com/ifs-au

Heights 👉 Join Jake in maintaining your energy, with Vitals. Get 20% off with code Room20: https://highpfrmc.com/heights-vitals-au

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TS Anil’s journey through the world of banking has been anything but conventional. From boardrooms in Tokyo to the fast-moving culture of Silicon Valley, each step taught him that real change doesn't come from preserving the past, it comes from building something new.

In this episode, TS reflects on his decision to leave the safety of big banks, the career-defining leap into tech at Visa, and how those experiences prepared him to lead Monzo through some of its toughest moments, including the height of the pandemic. He shares the story behind Monzo’s most innovative features, the importance of listening closely to customers, and why purpose and adaptability are the real keys to leading in uncertain times.

It’s a story of bold decisions, quiet resilience, and building the kind of company you’d want to be a customer of.

Partners:

IFS - award-winning Asset & Service Management software

👉 Reimagine your operations at: https://highpfrmc.com/ifs-au

Heights 👉 Join Jake in maintaining your hydration. Get 20% off with code Room20:

https://highpfrmc.com/heights-hydrate-au

The Book of Money: How to feel good (or better) about your finances by Monzo publishes 4th September: https://www.amazon.co.uk/Book-Money-better-about-finances/dp/1804948667

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Gary Stevenson didn’t follow a traditional path, he challenged it at every turn. Expelled from school at 16 and later pushed out of Citibank for speaking up, Gary’s journey has been shaped by resilience, rebellion, and a refusal to stay silent.

In this episode, Gary opens up about the high-stakes world of trading, the psychological toll of chasing success, and the personal battles that came with confronting corporate power. From unexpected lessons in Tokyo to quiet acts of solidarity in a cutthroat industry, his story is as much about survival as it is about awakening.

It’s a powerful look at what happens when you step off the fast track, and choose to fight for something bigger than yourself.

Partners:

IFS - award-winning Asset & Service Management software

👉 Reimagine your operations at: https://highpfrmc.com/ifs-au

Heights 👉 Join Jake in maintaining your hydration. Get 20% off with code Room20:

https://highpfrmc.com/heights-hydrate-au

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George Heaton’s journey with Represent wasn’t a straight line, it was a series of hard pivots, gut checks, and quiet rebuilds. What started as a passion project in streetwear hit a breaking point, forcing George to confront what wasn’t working and make the kind of decisions most founders avoid.

In this episode, George takes us through the moment everything stalled, the warehouse bathroom where reality hit, and the bold move to rebuild the brand from scratch. He shares how returning to simple product drops reconnected Represent with its roots, and how stepping back from the business side, by bringing in a CEO, unlocked new levels of creative and commercial growth.

It’s a story about letting go, doubling down, and the power of starting over, with purpose.

IFS - award-winning Asset & Service Management software

👉 Reimagine your operations at: https://highpfrmc.com/ifs-au

Heights 👉 Join Jake in maintaining your hydration. Get 20% off with code Room20: https://highpfrmc.com/heights-hydrate-au

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Paul Clement never set out to build a flashy startup, he set out to build something that mattered. Born from genuine passion and a deep connection to the community he served, his business grew not by chasing trends, but by staying grounded in purpose.

In this episode, Paul talks about the power of building slowly and sustainably, why loving the process matters more than chasing quick wins, and how adapting to change doesn’t mean losing your identity. From bootstrapping with intention to making decisions based on evidence, not ego, his story is a masterclass in thoughtful entrepreneurship.

It’s about staying true to your values, trusting your pace, and creating something that lasts.

IFS - award-winning Asset & Service Management software

👉 Reimagine your operations at https://hppod.co/ifsai

Heights 👉 Join Jake in maintaining your hydration. Get 20% off with code Room20:

Audio Link: https://highpfrmc.com/heights-hydrate-au

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Jim Chapman was part of a digital wave no one saw coming, and found himself at the center of it. What started as casual videos turned into global influence, brand deals, and a move to London that changed everything almost overnight.

In this episode, Jim reflects on the chaos and charm of building a career in the early days of YouTube, the pressure to constantly evolve as the internet shifted beneath his feet, and how fatherhood forced him to rethink everything, from content schedules to what success really means. He shares the highs, the hidden challenges, and the quiet moments that taught him how to keep creating without losing himself.

It’s a story about fame, flexibility, and finding clarity when the spotlight dims.

IFS - award-winning Asset & Service Management software

👉 Reimagine your operations at https://hppod.co/ifsai

Heights 👉 Join Jake in maintaining your hydration. Get 20% off with code Room20:

https://highpfrmc.com/heights-hydrate-au

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Aron D’Souza didn’t just question the rules, he set out to rewrite them. Frustrated by the limitations of legacy institutions, he launched the Enhanced Games: a bold, controversial vision aimed at redefining the future of human performance.

In this episode, Aron shares the moment he walked away from venture capital to pursue something far riskier, the power of writing down your vision before speaking it aloud, and how viral headlines paired with deep operational strategy created a movement that couldn’t be ignored.

From fierce public debates to long nights and personal trade-offs, this episode is a story of conviction, controversy, and building something truly unprecedented.

IFS - award-winning Asset & Service Management software

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Learn more about Enhanced Games and follow Aron D’Souza for upcoming announcements.

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Dan Bosomworth wasn’t chasing fame, he was chasing a feeling. One moment in his garage, fed up with complacency and craving change, sparked the creation of a product that would go on to redefine recovery for athletes, celebrities, and wellness seekers around the world.

In this episode, Dan unpacks the early missteps, how challenge creates change, and the tough calls that pushed Brass Monkey toward the luxury space. From building bespoke tech to navigating near collapse, his journey is a raw look at what it takes to back yourself, build from the ground up, and create something truly original.

It’s a story about discomfort, discipline, and designing a brand that stands the test of time.

IFS - award-winning Asset & Service Management software

👉 Reimagine your operations at https://hppod.co/ifsai

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