In this conversation, Ben speaks to Stefan Boronea, Co-founder and CTO of Proportunity.

Stefan discusses why it’s now a commonplace thing in western society for people to want, and experience, several different careers over the course of their lives, and why the degree of choice afforded to us is both a blessing and a curse.

They discuss the management of our most precious resource, time, and how doing it successfully amounts to fulfilment in our working life. Stefan explores the human tendency to over-estimate risk, and its implications on our choice of work. Finally, their conversation touches on why we should all aim to be an outlier, and how self-knowledge is a critical part of identifying the optimal path for ourselves.

In this conversation, Ben speaks to Tim Chong, Co-founder and CEO at Yonder. Tim’s story bucks the trend, culturally and personally. Tim has a unique awareness of what he calls his ‘mental itches’ - inclinations that he treats as seeds - giving them the time and space to take root.

They discuss why there is never a binary moment where people realise they’ve “made it,”. Why our best work doesn’t have to be limited to a small number of skilled professions. They discuss how boredom while volunteering and a “road to Damascus” moment shaped Tim’s view, and gave him the niggling feeling that led Tim to found Yonder.

Tim also discusses how he has previously defined his own best work extrinsically rather than intrinsically, and how a consciously-defined “Plan Z” allows him to view risk from a fresh perspective.

In this conversation Ben speaks to Daniel Svonava. Daniel is a Co-Founder of Superlinked. Daniel was previously a Senior Software Engineer at Google before founding Primeflow at the CTO.

He splits his time between the ‘manic creation’ of being an executor, and the quiet contemplation that comes with thinking about wider strategy and career goals. Based in Switzerland, Daniel shares how location can be ones of the aspects that affects not only the life we lead outside of work, but also the macro level of how we work.

They also discuss the rewards of ‘going deep’ into learning and the natural feedback loops that form from repeating this process, as well as how we can make work more of a game, incorporating aspects of play into how we approach problems.

Their conversation also covers how we can stay aligned to the visions we set for our careers, and how we can measure our journey along that path, in both the near and long term.

In this conversation, Ben speaks to Ben Phillips, co-founder and CTO of Thread.

They approach a wide range of topics, from Stoic philosophy to mental health, relationships, sleep, burnout, learning, decision making and others - which makes their conversation distinctly in-depth and, at times, deeply introspective.

In detail, they discuss the role of death and how we can use it to cultivate resilience in ourselves. How to use mental frameworks to find the benefit of hindsight in advance. And how Ben has developed outstanding professional relationships - like the one with his Co-founder - now onto their second company - and 16th year together.

Ben openly shares his experience of burnout. How a combination of obsessive learning and lack of sleep meant that … after an all-hands meeting late one Friday- Ben sought found support from the people and services around him.

The conversation is so wide-ranging, and so natural, in part because they've been through similar experiences. The lessons Ben has learnt have been hard at times. Yet hearing from Ben, you get the sense that he’s opened his heart to the toughest moments - to soak in every part of his experience. The full tapestry of life as a founder is complex - and as a result - difficult, illuminating and unique. Ben’s story so far reveals truths we can all relate to and learn from.

In this conversation Ben speaks to Maksym Schipka, the CTO at Vortexa. Maksym has spent his career working in cybersecurity and was previously the CTO at Clearswift.

Maksym details his journey of optimisation, from focussing on survival after leaving home and studying at University, to concentrating on learning and becoming a CTO.

They discuss circles of influence, status and the journey of change that happens throughout our careers, as well as working to make yourself redundant as a leader.

Maksym’s attitude towards having purpose, and the constituent parts that create purpose, have allowed him to focus on what will bring him happiness through work, but also in his life outside of it.

In this conversation, Ben speaks to Afiya Chohollo, VP of Engineering & Technical Program Management at Onfido.

They discuss why specialists and generalists are complementary to one another, as well as the concept of multi-potentiality. Afiya explains the Einstellung effect, and why being more generalist often gives us an advantage when it comes to problem-solving.

Afiya delineates two psychological drivers in her life: positive forces like curiosity, problem-solving and inspiring leaders, and forms of hardship, as well as being underestimated and the imposter syndrome that results. This set of drivers leads Afiya to be intensely competitive with herself which, paradoxically, has enabled her to outperform her doubters over the years.

She also describes a model she calls “the cone of uncertainty,” which she uses to approach decision-making and to inform how involved she gets with her teams’ planning.

In this conversation, Ben speaks to Albara Hakami, VP of Payments and Founding Team Member at Corpay One. Albara has always been driven by an intense curiosity, which has led to him living a digital nomadic lifestyle and founding companies in multiple industries.

As a result, he approaches work with a unique perspective. He talks to Ben about the way in which focussing on topics he’s passionate about helps him to grow professionally and personally, and the way in which he uses his principles to guide and tame his inner child.

They discuss how to balance making big decisions with clarity whilst receiving the input of others, and why learning is one of the most important principles that Albara considers when making the final call. They also discuss the extrinsic and intrinsic motivations that have guided his unique journey, as well as how our environments work to shape these motivations into habits.

In this conversation, Ben speaks to Claire Donald, VP of Engineering at MOO.

Claire’s career trajectory has seen her work in the army, HP, and the civil service, as well as contracting, before joining her current organisation - all alongside balancing the demands of motherhood. She has a comprehensive knowledge of different working styles and cultures, and a refreshing honesty and openness about how to navigate these.

Ben and Claire's conversation touches on how motherhood has helped Claire in her own working life, as well as the challenges of taking a pay cut. She talks with candour about her experience of burnout, and about its causes and the signs that, in hindsight, showed she was suffering from it.

They discuss Claire’s own managerial toolkit, which is centred around generalism and empathy, as well as the future of workplace culture as the professional world emerges from the aftermath of the pandemic.

In this conversation, Ben speaks to Stephen Whitworth, co-founder and CEO of incident.io. Stephen began his career at Hailo, Co-founded Ravelin and joined Monzo early on. Since starting incident with Pete and Chris, Stephen has gone on to raise over £34 million dollars at the date of this recording, from notable people like Monzo’s Co-founders Tom Blomfield and Jonas Templestein, Monzo’s lead investor Eileen Burbidge - the CEO of GoCardless Hiroki Takeuchi, the CTO of Loom Vinay Hiremath, Instagram’s co-founder Mike Kieger - and a seed and Series A Led by Index Ventures.

Yet, the conversation touches on very little of that. They explore Stephens personal journey. How he discovered Engineering. The way he approaches the ambiguity of his work. How cross pollination between different disciplines provide him with unique insights and how the sense of freedom engineering has given him - has led him.

Stephen talks Ben through a model for augmenting quantitative data with our gut feel in decision-making, and Stephen talks with candour about why effective prioritization is, by necessity, a painful process.

In this conversation, Ben speaks to the Head of Engineering at WorldPay, Usman Bashir.

The conversation predominantly centres on mentorship, with Usman sharing his route towards management and then on to leadership, detailling the role of mentors in that journey. He reveals his experiences in finding a mentor, why their seniority and experience matters, and why it’s helpful if you don’t work at the same company as them.

Usman shares his insights on the key points throughout a mentoring process from both sides - how to know when your mentor might not be a fit for you, and how to run your first session as a mentor.

He also details the importance of values in continually improving one’s decision-making, and what it really takes towards becoming a leader that truly generates change.