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 : [email protected]

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

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

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 [email protected]

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...

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 [email protected]

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

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 [email protected]

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/

In this episode of You Win or You Learn, I share a huge client win that highlights the power of consistent, value-driven marketing.

Links

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 [email protected] .

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...

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 [email protected] .

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

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!