Shanley Knox is a brand strategist and social entrepreneur based in New York. In this conversation, we get into dismantling a business on the cusp on success, a dangerous bias around meaningful work, the audacious hope of building something new, and why a set of traffic lights in Downtown Manhattan changed just about everything… Show Notes 08:00 A tipping point to dismantle a company 12:00 Returning to Africa 21:00 Recognizing real problems as a founder 28:00 The feeling of belonging and not belonging 32:00 The photographer as observer 41:00 Stakeholders that strategists don’t always notice 52:00 The audacious hope of building a thing 59:00 What happens when you freeze in the face of possibility 66:00 Cultural bias around meaningful work

Sims Foster is co-founder of Foster Supply Hospitality - a group of rurally independent small hotels and restaurants based in New York's Catskills Mountains. In this conversation we get into facing up to the inevitably of hundreds of tiny failures, finding thought partners, the importance of the practice room, how the hospitality industry could rethink the ways it trains talent, and why local matters. Show Notes 05:00 Introducing Foster Supply Hospitality (and a rogue refrigerator) 08:00 Why the Catskills is such a storied region, and how it’s changed so dramatically in the past few decades 15:00 Starting in hospitality: from dishwashing to digging into data 25:00 Bringing a music sensibility to the hospitality business - and the importance of the practice room 33:00 Facing up to the prospect of constant tiny failures 36:00 The future of training in the hospitality industry 45:00 How Sims assesses new hotel and restaurant opportunities 50:00 Underrated factors that make or break a hospitality company 54:00 The colossal financial failure - and making a recovery 63:00 Seeking out thought partners… and working with your life partner 70:00 Recognizing crisis, and moving forward 77:00 The importance of doing business for local good

Jonathan Stark is on a mission to rid the world of hourly billing. He helps freelancers, consultants and creatives of all flavours find better ways to do the work they want to do in the world. Jonathan’s own journey has gone from live musician to digital agencies, independent software developer to teacher. While his books, talks, and daily newsletter are now hugely successful - there have inevitably been some bumps along the way. In this conversation we get into why artists and designers can be very opposite, the real value of music, unexpected occurrences of the employee mentality, and why marketing can make us mad. Show notes 04:00 Getting it wrong on-stage 11:00 Why creatives get pulled in two directions 17:00 Funding the mission 22:00 The value of music 35:00 What it means to have an employee mentality - even when you don’t think you do… 43:00 A big lesson from Disneyland 50:00 Wrangling with marketing 58:00 Getting comfortable with speaking and writing in public 67:00 The value of podcasting and newsletters 74:00 Daily publishing

Amsterdam is widely renowned as a global hub. It's a centre of art, creativity, forward-thinking approaches to sustainability, and a centre of incredible nightlife. Olaf Boswijk has been at the very center of Amsterdam's nightlife scene for well over a decade: as the music programmer and resident DJ at the Club 11 venue, before setting up the legendary Trouw, and the equally vital De School. It's fair to say Olaf's had a big part to play in creating a worldwide buzz around electronic music in the city. When Olaf decided to take a little break, he headed out of the city for a little while with his wife Mirla in their yellow camper van. But this wasn't any old trip - they headed west to Canada, went south into the US, and then all the way through Latin America to Patagonia. It was in southern Chile that they fell in love - with an incredible part of nature they've come to call Valley of the Possible. Valley of the Possible is a place where Olaf, Mirja and their team invite and challenge artists, scientists and other creative thinkers and makers to envision alternative perspectives on our relationship with the natural world. In this conversation Olaf shares the back story of launching this latest project, the questions he asks about his own creative work, his attitude to risk, and why less ambition may be a positive sign. Show Notes 05:00 Hitting the road from Amsterdam to Patagonia 10:00 The tension between the DJ and club owner 18:00 The power of live vs pre-recording 24:00 Falling in love in Chile 30:00 Making career pivots 33:00 Bringing Valley of the Possible to life 42:00 Olaf's attitude to risk and ambition 55:00 Asking the difficult questions around climate and nature 59:00 Nightlife going from global to local 63:00 The impact of fatherhood

A lot's happened since 9 year old Dmitry Koltunov and his family packed a few suitcases, left the Soviet Union, and headed west into the unknown. Today, he's known by many as the co-founder of Alice, a hugely successful tech company serving the hospitality industry. To many hundreds more, he's the indefatigable linchpin of a popular startup fellowship program. And to others, he's the creator of a new Broadway musical. Before all these ventures, Dmitry had to learn a new language and culture, and found himself in the gladiatorial environments of corporate America. It was only after two very different visits to New York's Lower East Side that his current path began to emerge. In this wide-ranging conversation we get into the surprises that come when following the American dream, why confidence can create fragility, the commonalities between hiphop and startups, and lessons learned from freestyling with one Lin Manuel Miranda. Show Notes: 6:00 Lower East Side free styling with Two Touch &  Lin Manuel 17:00 Detecting the difference between startups and hobbies 25:00 The gladiator game of business - and going the other way 30:00 Following the American dream, and observing culture 43:00 Hiphop and startup communities 48:00 Being fragile from the confidence 58:00 Structures and segments of creative work 66:00 Handling success 73:00 Writing Broadway musicals

Steve Bodow is a writer and producer, most well-known for being executive producer of The Daily Show. ----- Jerry Seinfeld says writing is perhaps the hardest thing in the world. But sometimes it feels easy. The pen just flows. What’s Jerry on about? And then all of a sudden it gets hard. The page stays blank. When you’re writing under time constraints, it can get harder. And working under them pretty much every day - probably harder still. How about writing for a TV show where millions of people are tuning in 4 times every week to be both entertained and informed? Yep, that's not always gonna come easy. As a writer and then executive producer of The Daily Show, Steve Bodow's done just that. He was an integral part of a team that won 16 - yes, 16 - Emmy Awards before departing the show in 2019 with well over a thousand episodes under his belt. Since then he’s worked on TV shows like Patriot Act with Hasan Minhaj, as well as high profile political campaigns, and a range of his own new projects. In this conversation on writing, producing, and so much more we get into the joy of travel, juggling multiple projects, the allure of writing, finding a meditative state in improv, and what makes for a good host... yes I was taking notes. Show Notes: 04:00 The start of In Quarantine 08:00 Moving from behind the scenes to front and center 12:00 The flow of improv 17:00 The allure of writing 22:00 Shifting from writer to management 28:00 Recognizing the pace of selling 38:00 Working in sprints 43:00 Seeing the game slow down over time 48:00 Working to deadlines

When it comes to starting any new project - whether an app, a product, a course, a book - there are so many potential traps to fall into. One of the biggest is not understanding what people actually want. After falling into this trap more times than he’d like, Rob Fitzpatrick decided to write a book to help others avoid it. Fast forward a few years and Rob’s career is entering its third phase: from seeking scale in his days as a founder going through tech accelerator Y Combinator, which gave him the inspiration for that first book - The Mom Test; to going after the hammock lifestyle that comes with the freedom of working remotely; to focusing more on consistency and reliability. This third chapter arrives alongside his third book, and brings together much of what he’s learned and built so far. Write Useful Books is a book, but it’s also a community, software product, and potentially a backer for independent nonfiction authors. In this conversation we get into several topics Rob hasn’t talked about much in public before - from how he deals with tougher days; to changing his mindset about marketing; and the unique approach he’s taken with his business partner. Show Notes: 04:00: The gap between books two and three 10:30: Applying product design principles to books 16:00: The theme running through Rob’s books 24:00: Staying loyal to an audience, but also to yourself 28:00: Respecting marketing 35:00: Y Combinator Rob vs. Hammock Rob 40:00: Solo versus team and a novel way of being in partnership 47:00: Interlocking layers to support independent non-fiction writers 56:00: From 700 copies to 100,000 61:00: Comfort tasks 67:00: Overcoming the rough days, and disappearing 75:00: The importance of thinking as entrepreneurship as a career, not a company or project

In 2003, a new magazine launched. It felt a little different to what else was on the shelves at the time. Covering music, literature, street art and fashion, it featured a new generation of talent, and had a focus on quality: not just the content, but on bespoke cover art and high-end paper stock. The magazine was called Blowback and one its co-founders was a 21 year old called Georgina Wilson-Powell. After the London-based company folded in 2007, Georgina spent time at one of the world's largest publishing companies, traveling around the globe as a journalist. It was these gas guzzling trips that in fact led her back to entrepreneurship - this time as founder of sustainable living magazine Pebble. This time, Georgina is going it alone, building an ethical media business as a solo female founder. In this deep dive conversation we get into why not being an expert can be freeing; the challenge of intertwined identities as an entrepreneur, using grief as fuel; and how build support structures when you're going it alone. Oh and you'll hear Georgina’s dog Maggie in the background a couple of times... we just couldn't bring ourselves to edit her out... Show notes: 01:00: The craft of editing 05:30: The sudden end of Georgina’s first company 11:30: Why magazines have such a strong allure 14:30: Lost experiences post-failure, and the intertwined identity 23:00: Coming back for round 2 of entrepreneurship 29:00: Why not being an expert can be a positive 32:30: Dealing with grief 37:00: The differences being a solo founders vs. having multiple founders 40:00: Communicating with life partners in different work situations 46:00: Finding support structures 51:00: Being a female founder of an ethical media business 56:30: Why write a book 62:30: Being everything to everyone, and the challenges of staying visible 66:00: Bad advice 77:00: The importance of knowing your own mind, and overcoming fear

Starting a new company? Let's be honest - it's hard. In the midst of a global pandemic? Yep, definitely hard. Compared to a decade ago there are now far more places to get support in those early days, but Andrew Hutton and the team at Day One feel there are still some gaps that urgently need to be filled. With the belief that entrepreneurship is going to be the most important skill of the 21st century, Day One are seeking to rethink the way early stage companies get built, going beyond the narrative of venture capital as the be-all and end-all, and to support all kinds of founders who are focused on outcomes, not just achievements. In this conversation we get into challenging the conventions around building early stage companies, the identity shift when becoming a founder, how to focus on outputs first, and understanding which game you're really playing. Show Notes 06:30: The conventions around ‘early-stage’ startups 14:00: Conforming to typical milestones and points, and what’s shifting 20:30: What emerges during the early stages, and the questions of identity around being a founder 32:30: Chasing dreams with rigor, and the shift from inputs to outputs 40:00: What Andrew rewired in himself as he became a company founder 47:00: The meta game of running a business that helps other businesses 52:00: Building a community and education business that isn’t built around a guru 55:00: Launching, relaunching, and what happens when the energy starts to dissipate 61:00: Pockets of influence and figuring out the game you’re playing 64:00: Underestimating time

Back in 2008, Kevin Kelly wrote a now legendary article on the long tail, and the concept of 1000 true fans. It's a concept that's gained ground in the 12 years since it was first posted, and in 2020, those trends around fandoms and the wide creator economy are - like a lot else in the world - accelerating. Today here are many new voices and platforms. 1000 true fans becomes 100. There are Macro trends in micro communities and micro payments. The way we create and consume content of all kinds is changing at an extraordinary rate. In the middle of all this, both as a guide for brands and creators, and as a creator building a brand of their own, is Zoe Scaman. Zoe's spent time at some of the world's leading brands and agencies - from Naked Communications and Droga5; to Adidas and Ridley Scott's Creative Group. Today she runs the strategy studio Bodacious, helping develop and define compelling brands of all flavors. Unafraid to share what she's learnt, and shout out the successes in public, she's built a significant following over the past 12 months in particular. But it's not all been an upward curve. We talk about the ill-fitting nature of the word 'fit' when organizations are looking for talent; rejecting linear progression and social conventions; the deep fear held by many people in the advertising industry; and the value - and challenges - of putting yourself out there in the world. Show Notes: 04:00: Why ‘fit’ is dangerous for many businesses 08:30: The vindication of having ‘Range’, and rejecting the linear path 16:30: Who was missing for Zoe when she was at school 20:00: What it means to ‘bang down the door’ 22:30: Persistence vs. Confidence 28:00: The Phoenix and The Magpie 32:30: What 22 year old Zoe would make of Zoe today 34:00: The shift from employee to owner 40:00: The bit before Bodacious, and dealing with the self doubt 45:00: What happens when a full-time gig comes along… and making a vote of confidence in yourself 50:30: Putting yourself out in the world, and managing energy 57:00: The anger and fear held by others 64:00: Homesteading, and staying curious 69:00: Culivating fandoms - for others, and for yourself