You Win or You Learn with Dylan Haskin

Dylan Haskin
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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.

Episodes

  1. 05/19/2025

    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

    1h 19m

  2. 02/17/2025

    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 Instagram (@the_roofpod) The RoofPod | Cape Town The RoofPod

    1h 10m

  3. 02/03/2025

    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

    4 min

  4. 12/17/2024

    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 My Links Instagram : Instagram (@dylanhaskin) Website : http://www.dylanhaskin.com Subscribe https://bit.ly/2H4LSmW Listen on Spotify : https://open.spotify.com/show/4uKQIGx... Listen on Apple Podcasts : https://podcasts.apple.com/us/podcast...

    9 min

  5. 12/09/2024

    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

    1h 30m

  6. 11/25/2024

    Devin Paisley | Building Community, Imposter Syndrome, and Comparison

    In this episode of You Win or You Learn, I sit down with Devin, a photographer, trail runner, and serial entrepreneur, to talk about what it really takes to build a personal brand that stands out. We talk highs and the lows as Devin shares his transition from modeling to photography and recounts the creation of Woodstock Moto Co., a DIY motorcycle garage and creative hub in Cape Town. A key theme in this episode is that of turning passion into purpose, why showing up (even when it’s hard) is non-negotiable, and how collaborating with others can hugely elevate your game. Plus, we dig into the anxiety of putting yourself out there, the pressure to always be on, and how to keep your edge without burning out. If you’re a creator, entrepreneur, or just someone looking to grow, this episode will hit home. Check it out and let me know your favourite takeaway! 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.z My Links Youtube: https://www.youtube.com/@DylanHaskin Subscribe here : https://bit.ly/2H4LSmW Instagram : https://www.instagram.com/dylanhaskin/?hl=en Listen on Spotify : https://open.spotify.com/show/4uKQIGx... Listen on Apple Podcasts : https://podcasts.apple.com/us/podcast... Davin’s Links Devin’s Instagram : https://www.instagram.com/devin_paisley/ Devin’s Website : https://devinpaisley.com/

    1h 25m

  7. 11/11/2024

    How We Grew a Brand from 200 Followers to 70,000 in 18 Months

    In this episode of You Win or You Learn, I share a huge client win that highlights the power of consistent, value-driven marketing. Alexander Swart Property Group, based in Brackenfell, grew from just a few hundred followers to 70,000 across multiple platforms in just 18 months—all without spending a cent on ads. Our marketing strategy was simple but effective: focus on educating their audience and building trust. This approach didn’t just boost their visibility; it also helped them establish authority in the South African property market. The results speak for themselves: not long after growing their online presence, Alexander Swart was invited to speak at a major industry event in Johannesburg. I’ll walk you through how this small, local real estate team managed to go from a niche presence in Cape Town to being recognised as experts in their field—showing that staying consistent, giving value first, and embracing organic growth can lead to real, impactful results. If you found this episode valuable, don’t forget to subscribe! You can listen to more episodes on Apple Podcasts and Spotify. About You Win or You Learn: If you’re 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’d like to be a guest on this podcast, please reach out to me at dylan@haskinstudios.co.za . Links Youtube: https://www.youtube.com/@DylanHaskin Instagram : http://www.instagram.com/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 Work with me : contact@dylanhaskin.com

    5 min

  8. 10/28/2024

    Why We Should’ve Hired an Accountant Sooner

    In this episode of You Win or You Learn, I’m sharing one of the biggest lessons I’ve learned since starting my business - which is to get an accountant—like, yesterday. When you’re just starting out, you’re probably trying to juggle everything yourself, but trust me, this is one area you don’t want to DIY. Having an accountant isn’t just about doing taxes—it’s about working smarter. They’ll help you stay on top of everything from cash flow to tax efficiency, and they can save you a ton of stress down the road. Honestly, it’s one of the best investments we made for our business, and I wish we had done it sooner. Be sure to subscribe for more tips and insights on running or starting a business, and listen in on Spotify and Apple Podcasts. About You Win or You Learn: If you’re 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’d like to be a guest on this podcast, please reach out to me at dylan@haskinstudios.co.za . My Links Subscribe here : https://bit.ly/2H4LSmW Instagram : Instagram (@dylanhaskin) Listen on Spotify : https://open.spotify.com/show/4uKQIGx... Listen on Apple Podcasts : https://podcasts.apple.com/us/podcast...

    4 min

  9. 10/14/2024

    Breaking into Cinematography: Building a Business From Ground Zero

    In this episode of You Win Or You Learn, I’m talking creativity and business with Andre Hugo. A successful cinematographer, Andre shares his passion for storytelling and finding excitement in new and unexpected subjects. His professional experience was hard won, and his journey a winding one where he drew from multiple areas of his life to build both his business and approach to life. From mountain biking and sports, to the hidden costs of running a creative business, developing resilience and mentoring fellow entrepreneurs, join us for a candid conversation that’ll hopefully inspire you to keep rolling! 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 Subscribe here : https://bit.ly/2H4LSmW Instagram : Instagram (@dylanhaskin) Listen on Spotify : https://open.spotify.com/show/4uKQIGx... Listen on Apple Podcasts : https://podcasts.apple.com/us/podcast... Andre’s Links Andre’s Instagram : Instagram (@andrehugomedia) Andre Hugo Media Website : Andre Hugo | Cinematographer | Editor

    1h 15m

  10. 09/30/2024

    Growing a Business from Zero Followers: Social Media Strategy Case Study

    In this episode of You Win or You Learn, I share how we approached a local brand with a cold email and turned them into a social media client. I'll walk you through our process for identifying businesses with potential, reaching out, and discussing strategy. Plus, I’ll share insights into the importance of listening to clients’ concerns and creating content that fits their vision, in this case specifically focusing on organic growth and brand awareness without relying on ads. Watch the full video to see how we're planning to build their online presence from the ground up! 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 here 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 . Links Subscribe here : https://bit.ly/2H4LSmW Instagram : http://www.instagram.com/dylanhaskin 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

    13 min

  11. 09/16/2024

    E02 - Going into the unknown Ft. Kevin Sawyer | You Win or You Learn Podcast

    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 In this second episode of You Win or You Learn, I'm joined by Kevin Sawyer, owner of Show + Tell, a marketing agency here in Cape Town South Africa. Kevin shares how he got into photography, video and finally why he decided to move from a freelancer to starting a company. 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 here 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 Subscribe here : https://bit.ly/2H4LSmW Instagram : http://www.instagram.com/dylanhaskin 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 Kevins Links : Instagram : https://www.instagram.com/kevinsawyer/?hl=en Show + Tell Instagram : https://www.instagram.com/showandtell_media/?hl=en Show+Tell Website : https://www.showandtell.co.za

    1h 15m

  12. 08/15/2024

    Lets begin! | South African Entrepreneurship Podcast

    In this first episode of You Win or You Learn, I'm setting some intentions of what this podcast is about and who it is serving. 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 here 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 .

    8 min
  • 12 Episodes

About

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.

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