Episodit
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In this conversation, Ben speaks to Kimeshan Naidoo, the CTO at BX, and former co-founder and CTO at UniBuddy. They explore stress, health, meditation, stoic beliefs, and the philosophies that guide Kimeshan’s working life.
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In this conversation, Ben speaks to Mike Fisher, the (outgoing) CTO at Etsy.
Mike and Ben discuss why he sees high-performing teams as “accountability communities”. Why grounding our identity firmly in our job title is misguided. How he’s found the courage to ask critical questions of himself and his peers. Why his career has been defined more by running towards things he loves than away from things. And why scrutiny is important to his work.
Mike has built multiple consequential companies - and through his insights - it is clear why he is so well regarded.
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In this conversation, Ben speaks to David Heinemeier Hansson, the creator of Ruby on Rails - and Co-owner & CTO of 37signals - the company behind Basecamp and Hey.com.
They explore David’s past and it’s influence on his work. Why he finds meaning by pushing himself harder. Stoicism and its continuing influence on David’s life. How to externalise factors beyond our control. How to work through adversity. The differences between loyalty and obligation. The meaning of legacy, and much more.
It makes for the type of conversation Ben wishes he'd had years ago, and one he won’t forget.
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In this conversation Ben speaks to the Founder and Chief CTO Coach at CTO Craft, Andy Skipper. Andy was previously the CTO at MADE.com, Lumitrix and Comic Relief before founding CTO Craft.
After finding himself in a CTO role at a pre-product startup almost by accident, Andy had his first experience of burnout. Experiences like this early on in his career seem to have fuelled Andy to look for opportunities that save people from similar circumstances, highlighting red flags to people early so they don’t have to learn through experience.
They discuss self-awareness, Andy’s early influences and the value of professional coaching, as well as Andy’s own experience with chronic illness and how that’s affected how he uses his energy effectively.
Andy has a deep care for individuals, learning from environments where he wasn’t able to access the support he needed to grow. He now places a lot of focus on helping to improve the individuals within a team, not the entire unit, putting more emphasis on a coaching style of leadership, driven by empathy.
Their conversation is highly personal - and by going so deep - they uncover truths all of us experience - but don’t articulate.
Multiple people recommended Ben speak to Andy - and after listening - he thinks you’ll see why
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In this conversation, Ben speaks to Sara Stephens, CTO & Co-founder at Rest Less.
Her own story is a distinctive one, which has seen her uproot herself geographically throughout her life. Sara speaks in detail about the process of self re-invention that accompanies each of these shifts. And she shares how she realised that other needs besides her financial ones could be satisfied through work.
Rest Less is a digital community for people in their 50s and 60s, with support on a range of topics including work and careers. As such, it is unsurprising that the impact, and irrationality, of ageism at work is one area on which Sara shares her insight during their discussion - one that many of us over look.
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In this conversation, Ben speaks to Min Ong. Min is the ex CTO at nate and now an Engineering Manager at WeTransfer.
They discuss how Min transitioned from an IC role to a managerial one - a move that was not straight forward. They talk through the challenges associated with changing your place of work, and the importance of creating environments where people can safely reflect.
At every step, Min accepts the challenge of being true to her intrinsic long-term motivators - and their conversation is a deep dive into the mind of someone not willing to sacrifice what matters to them.
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In this conversation, Ben speaks to Kate Pljaskovova, Founder and CEO of Fair HQ.
Ben and Kate discuss how work and a career take shape - and use her own experience as the backdrop. In an interesting turn of events, having begun as a nanny, she stumbled into working for the start-up the child’s father was building … and then didn't look back from there.
They reflect on the importance of patterns, in our cultures and our memories, and reflect on the influence of our parents. Kate talks about why she feels able to step “outside of the box” in a way that others can’t - and she reflects on becoming a mother.
Kate’s expectations of work, are defined above all by freedom, learning, autonomy and this sense of adventure. She makes big career decisions based on learning and excitement, not opportunity cost - and it makes for one of the most free-flowing conversations to date.
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In this conversation, Ben speaks to the Founder and CTO at Cordless, Irina Bednova. Irina is an experienced Software Engineer, having led payments and operations at Monzo before leaving to join EF and found Cordless.
Irina is beautifully, and brutally, honest. She approaches taboo subjects like being money-motivated with a refreshing honesty that make the counterintuitive feelings we associate with them wash away with clear logic.
They talk though independence and how we can understand and respect our own limits when applying ourselves to work, and the safety nets we can build into our professional lives so that we engage with it in the long run. They also talk the psychological battle of fundraising and more.
Irina communicates with such truth and honesty - that her prolonged self-reflection makes it easier for us to frame how we view our own work..
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In this conversation, Ben speaks to Charlene Hunter, CEO & Founder of Coding Black Females. Coding Black Females is a nonprofit organisation who support Black female developers by providing networking events and learning opportunities.
Charlene talks Ben through the incredible story of how she founded CBF. She talks about the fact that opportunities that seem to just “fall into our lap” are often the result of years of dreaming and painstaking planning; and that big, “risky” decisions can be made in a risk-averse way.
Charlene talks about the barriers to entry for black women into technology, both in terms of how lots of companies sometimes think about recruiting, and how would-be engineers pigeon-hole themselves.
And fascinatingly, Charlene describes herself, and perceives her work at CBF, as an exact mix of the careers of both her parents. They talk about the influence that parents, and grandparents, have on us as individuals, as well as the way in which inspiring figures are often people who stood for something bigger than themselves.
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In this conversation, Ben speaks to Olov Eriksson, Chief Product Officer at Pleo. Their conversation focuses on the intersection between relationships and decision-making.
They discuss how Olov prioritises inputs over outputs. He explains how to use and understand your emotions to make big professional decisions. And they discuss the topic of fear; how it can drive us, hinder us, and help us navigate our working journey.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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