Cover image of show You Win or You Learn with Dylan Haskin

You Win or You Learn with Dylan Haskin

Podcast by Dylan Haskin

English

Business

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About You Win or You Learn with Dylan Haskin

In this podcast I, Dylan Haskin, am sharing my thoughts, philosophy and ideas around business, creativity, money, mindset and failure. I'll also be interviewing other South African entrepreneurs and business owners on their journey in business and the lessons they have learned along the way.

All episodes

12 episodes

episode E12 - How Thomas Sandell Went from DIY Camera Rigs to Filming the MTB World Cup artwork

E12 - How Thomas Sandell Went from DIY Camera Rigs to Filming the MTB World Cup

In this episode of You Win or You Learn, I chat with Cape Town-based filmmaker Thomas Sandell about his incredible journey in the world of filmmaking. From building DIY cable cams as a teenager to documenting some of the world’s top mountain biking events, Thomas shares how passion, persistence, and a bit of serendipity shaped his career. We dive into his early days shooting BMX and downhill with a borrowed handycam, how he landed his first job with Monster Energy, and the full-circle moment of finally filming the UCI Mountain Bike World Cup—nearly a decade after he first dreamed of it. Thomas opens up about what it means to stay creative, the pressure of freelancing, burnout, and learning to see world-class athletes as humans first. 🎧 Watch the full episode for an honest and inspiring conversation about filmmaking, growth, and chasing what you love. 📌 New episodes every month – Subscribe for more stories like this! Thomas Links : https://www.instagram.com/thomassandell_/ In this episode: 00:37 What YWOYL is about. 01:22 Who is Thomas Sandell. 03:23 Starting with film making. 16:54 Getting a job with Monster. 20:54 Mountain Bike World Cup dream actualising. 28:43 Dealing with nervousness. 32:12 Trust in the process. 35:35 Clients are just other humans. 38:49 Goals 44:33 Working smarter not harder. 46:20 Biggest Challenge 49:29 Staying Organised 54:38 Advice for aspiring film makers. 01:02:10 Learning to let go 01:08:15 Personal Projects 01:09:43 Work Life Balance Links Instagram : http://www.instagram.com/dylanhaskin Website : http://www.dylanhaskin.com Subscribe https://bit.ly/2H4LSmW Work with me : contact@dylanhaskin.com

19 May 2025 - 1 h 18 min
episode The RoofPod | From Garage Project to Rooftop Tent Revolution artwork

The RoofPod | From Garage Project to Rooftop Tent Revolution

In this episode of You Win or You Learn, I sit down with Simon and Tammy from The RoofPod to chat about their journey building lightweight rooftop tents. What started as a side project during the COVID lockdown quickly turned into a thriving business. Simon, with no prior tent-making experience, crafted a prototype in his garage, and that led to the creation of The RoofPod—a company focused on making camping more accessible for everyday people, not just hardcore overlanders. We talk about their struggles and triumphs, from creating their first models to facing cash flow problems, production hiccups, and slow growth. But with determination, they found success by building a community of loyal fans and customers who love the brand for its integrity and personal touch. Tune in as we explore how they made their vision a reality, the lessons they learned from launching a business without a traditional business background, and why staying authentic has been the key to their success. We also dive into some major business hurdles, like managing stock and international shipping challenges, and the importance of passion and persistence when building something from scratch. Chapters: 00:00 Introduction 01:05 How did The RoofPod start? 03:26 Current product range available. 04:34: Why lightweight rooftop tents and benefits there of? 08:32 Challenges of bringing a new product into the South African market. 13:25 Was a pivotal moment when The RoofPod turned from a personal project to product? 17:18 Marketing & building a community. 21:56 Where is the business run from? 24:09 Is the product made per order? 25:32 Is the product only sold locally? 32:22 Has there been any challenges with having employees? 34:42 Background with running businesses and lessons learned. 46:45 How do you handle client complaint? 48:42 Marketing besides social media. 58:07 What advice would you give other South Africans wanting to create and launch a product in South Africa? 1:03:02 Future plans for The RoofPod. 1:06:57 How can people find and contact The RoofPod? 1:08:02 Outro   Find The RoofPod here: Home | The RoofPod [https://theroofpod.co.za/] Instagram (@the_roofpod) [https://www.instagram.com/the_roofpod/?hl=en] The RoofPod | Cape Town [https://www.facebook.com/TheRoofpod/] The RoofPod [https://www.youtube.com/@theroofpod9331]

17 Feb 2025 - 1 h 9 min
episode How Zen Mind, Beginners Mind is helping my business. artwork

How Zen Mind, Beginners Mind is helping my business.

In this episode of You Win or You Learn, I break down a concept that seriously got me thinking—straight out of Zen Mind, Beginner’s Mind: “In the beginner’s mind, there are many options. In the expert’s mind, there are few.” The more experience we get, the easier it is to fall into patterns and miss new opportunities. But what if we could keep that fresh, open mindset—while still using what we’ve learned? That’s what I’ve been thinking about lately, especially in business and creativity. Let me know what you think—where could a beginner’s mindset change the game for you? Drop a comment below. 👇 Get the book here! Zen Mind, Beginner's Mind: Informal Talks on Zen Meditation and Practice [https://www.amazon.com/Zen-Mind-Beginners-Informal-Meditation/dp/1590308492]

3 Feb 2025 - 3 min
episode Business Challenges I Faced This Year | Finances | Adapting | Decision Making artwork

Business Challenges I Faced This Year | Finances | Adapting | Decision Making

In this episode, I’m reflecting on what I learned from running a business in 2024. This year really piled it on - from dealing with financial shortfalls and adapting to shifting client needs, to making some difficult decisions—you name the curveball, 2024 threw it. So I thought I’d lay down the real lessons I learned: managing finances, staying adaptable, and owning your decisions (even when they’re unpopular). Spoiler: knowing your “why” changes everything. Hit subscribe for more content about entrepreneurship in South Africa, and follow on Apple Podcasts or Spotify. About You Win or You Learn: If you are running a business in South Africa, or plan to, this is for you! I'm Dylan Haskin, and I run a marketing and content creation agency in Cape Town South Africa. I'm new at running my company, and want to use this podcast to document my journey in business and entrepreneurship. I will also be interviewing other South African business owners about their journey in business and have them share some of the lessons they have learned. If you would like to be a guest on this podcast, please reach out to me at dylan@haskinstudios.co.za [dylan@haskinstudios.co.za] My Links Instagram : Instagram (@dylanhaskin) [https://www.instagram.com/dylanhaskin/?hl=en] Website : http://www.dylanhaskin.com [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbFlHS0prTnh4Z0pnRzZORFRPbndLUmpiVXRHUXxBQ3Jtc0tuRXB5blhqRndwemFVbmgzVEJYSERlT3JETkI0b2Rxd0J3N0xtYVQxQUE5ZjdrOV9iTTN6WnVpclEwVVROMGNreXQ3cWlqQ2xXYnpOUlE1M1doalEzQ2d5LWUzc2JzeHVZMEVobU1sMTFfd0ZhS0Fqdw&q=http%3A%2F%2Fwww.dylanhaskin.com%2F&v=OgimpJ5KVxU] Subscribe https://bit.ly/2H4LSmW [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbWlncV90eDA5Y3BFRmx2NlpEcjc4VVVseGRZZ3xBQ3Jtc0ttR3I0VUdXcXI1TVctbW8yaTBieG1MRkp0MFlPZE1IOEloaVRyUUxuOGdSbURtX0ZhaTVrZlBCckI1S3ZsTDVJU256VVo1UWlLcWJTOFBBcGNKZ0ZwUHZ1VU9MYWhXb2locnRnMnhfU1VxTlZuVVh3RQ&q=https%3A%2F%2Fbit.ly%2F2H4LSmW&v=OgimpJ5KVxU] Listen on Spotify : https://open.spotify.com/show/4uKQIGx... [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbGFWQnp3azlYSVBTZTRrQm1iVTllaHpJQkZPZ3xBQ3Jtc0tsN0tOVDgyS3YtZUdaaEpTZk9fTTNjbmk1N2g4NC03WWZodHMyeDc4cTltc3M5YjBMRm5YaWtXRERQNUpEcWdTLUZ1V0FVSW9YejVyMVUzajgtblR2ZmJ0SlRQV0xic3hVckM2S3Nmak4tZnRHc0hySQ&q=https%3A%2F%2Fopen.spotify.com%2Fshow%2F4uKQIGxyI20ev2uTizDbfE&v=OgimpJ5KVxU] Listen on Apple Podcasts : https://podcasts.apple.com/us/podcast... [https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa0RCTHNCRTBabzZiNWluTi1JNjZveHRfYnlLQXxBQ3Jtc0tsSTdScUNZaWx0MHpMdHdvcS1rLUhJc1Q3SXJ3NkZJUU1nY3diQS1PRk9CU2Nmc09QUm5sTmZGTW5XbXpOYTQ5ZzFnLU1MMEpFM3ZmRG5LZFNmMm83S2VmVkJtemVReVBzQVF3cllLbWRKR3RCVVhSUQ&q=https%3A%2F%2Fpodcasts.apple.com%2Fus%2Fpodcast%2Fyou-win-or-you-learn-with-dylan-haskin%2Fid1668034337&v=OgimpJ5KVxU]

17 Dec 2024 - 8 min
episode Troy Davies | Freelancing, AI Tools, and Creative Freedom artwork

Troy Davies | Freelancing, AI Tools, and Creative Freedom

In this episode of You Win or You Learn, I sit down with Troy Davies, a Cape Town-based videographer and founder of Retroyspective. From corporate audiovisual to freelancing, Troy shares his journey and the pivotal projects that shaped his career. Fun fact: Troy was one of the first to hire me for creative work—shoutout to him for that! We dive into the balance between creative freedom and client needs, how AI is shaking up the creative industry, and why human touch still matters in a world full of automation. Troy also gives some solid advice for new creatives on landing clients and delivering real value. Troy’s Instagram: @retroyspective Troy’s Website: https://retroyspective.co.za Tune in for a mix of real talk, lessons learned, and insights on building a creative career. Don’t forget to like, subscribe, and let me know your thoughts! About You Win or You Learn: If you are running a business in South Africa, or plan to, this is for you! I'm Dylan Haskin, and I run a marketing and content creation agency in Cape Town South Africa. I'm new at running my company, and want to use this podcast to document my journey in business and entrepreneurship. I will also be interviewing other South African business owners about their journey in business and have them share some of the lessons they have learned. If you would like to be a guest on this podcast, please reach out to me at dylan@haskinstudios.co.za My Links Instagram :   / dylanhaskin   Website : http://www.dylanhaskin.com Subscribe https://bit.ly/2H4LSmW Listen on Spotify : https://open.spotify.com/show/4uKQIGxyI20ev2uTizDbfE Listen on Apple Podcasts : https://podcasts.apple.com/us/podcast/you-win-or-you-learn-with-dylan-haskin/id1668034337

9 Dec 2024 - 1 h 30 min
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