- 9
- Episodes
- 1
- Ratings
- Weekly
- Cadence
- 2026
- First episode
About OUTWORK
What’s the point of building a successful creative business if you don’t have the time to enjoy it? OUTWORK is a podcast about building a creative business around your life — not building your life around your business. Real estate media entrepreneurs Alex Coombs and Oliver Ward took two very different paths. Alex scaled. Oliver built boutique. Each week, with their guests they get into the real stuff: pricing, profit, hiring, systems, creativity, burnout, growth and freedom — sharing what worked, what didn’t, and what they’re still figuring out. Two approaches. Same goal. Build a business that gives you more life, not less of it.
- Publisher
- Oliver Ward
- Category
- business
- Language
- en
- Explicit
- No
- First episode
- 1 Sept 2026
- Latest episode
- 3 Nov 2026
Latest episodes
9 episodes in the feed.
3 Nov 2026
He Almost Quit. Then He Hired a Coach.
9 years building a business. One year away from burning it all down. Craig Cole was making good money running his real estate media company, but he was exhausted, overwhelmed, and ready to quit. Then he hired a coach. In this episode of OUTWORK, Oliver Ward and Alex Coombs sit down with Craig to unpack how coaching helped him rebuild his business, raise prices, create better systems, and finally get his life back. Today, Craig’s team is shooting houses without him, his business is expanding into new markets, and he’s spending less time working IN his business and more time working ON it. We talk burnout, delegation, pricing, building a team, and why sometimes the smartest business move is admitting you need help. If you’re doing everything yourself, this episode is for you. 🎙️ GUEST — CRAIG COLE Owner of Wavefront Media Co. wavefrontmediaco.com https://wavefrontmediaco.com/ 🙌 SPONSORED BY HDPHOTOHUB The all-in-one platform helping real estate media professionals streamline bookings, deliver media, and grow their businesses. hdphotohub.com https://hdphotohub.com/ 🤝 SPECIAL SHOUTOUT — MIKE HERMAN / CORE MEDIA OPS Mike and his team help both Craig and Oliver manage the behind-the-scenes operations that keep their businesses running. coremediaops.com https://www.coremediaops.com/ OUTWORK is hosted by Oliver Ward and Alex Coombs. Real estate media, entrepreneurship, and building a business that gives you more freedom. Work smarter. Live bigger. OUTWORK. #OUTWORK #RealEstatePhotography #BusinessCoaching #Entrepreneurship #BusinessGrowth
27 Oct 2026
What Should You Charge? Real Estate Media Pricing & First Clients
Thinking about starting a real estate photography or real estate media business? Start here. In this episode of OUTWORK, Oliver Ward and Alex Coombs break down some of the biggest questions they get from people entering the real estate media industry — from pricing your first shoot and building packages to finding your first real estate agent clients. We get into what you should actually charge, why being the cheapest photographer in your market can backfire, what services you should offer from day one, and how to figure out whether you’re actually making money on a shoot. Then we tackle the other big problem: getting clients. How do you build a portfolio when nobody has hired you yet? Which agents should you approach? Should you work for free? Should you cold email, DM, walk into brokerages, or start with people you already know? These are real questions we’re getting from photographers and videographers trying to build real estate media businesses — so we’re answering them. And we want YOUR questions. 👇 ASK US IN THE COMMENTS. Pricing. Packages. Clients. Gear. Hiring. Scaling. Editing. Sales. Marketing. Whatever you’re struggling with in your real estate media business, drop the question below. WE READ THEM. WE ANSWER THEM. Your question might become a segment — or an entire episode — of OUTWORK. 🎙️ LISTEN TO OUTWORK ANYWHERE YOU GET YOUR PODCASTS Prefer audio? OUTWORK is available on Spotify and all major podcast platforms. Search OUTWORK Podcast and follow the show so you don’t miss an episode. A huge thank you to HDPhotoHub for sponsoring OUTWORK and supporting the real estate media community. https://hdphotohub.com/ If you’re a real estate photographer, videographer, real estate media company owner, or you’re thinking about starting a real estate photography business, subscribe to OUTWORK. New conversations about building better businesses, getting better clients, making more money — and creating a business that actually works for your life. IN THIS EPISODE: Real estate photography pricing How to price your first real estate shoot Building real estate media packages What services new photographers should offer Photo, video, drone and floor plans How to calculate your actual profit Why competing on price can hurt your business How to build a real estate photography portfolio How to land your first real estate agent clients Cold outreach and email What to do when an agent asks for a discount Growing a real estate media business OUTWORK Hosted by Oliver Ward & Alex Coombs Sponsored by HDPhotoHub. #RealEstatePhotography #RealEstateMedia #RealEstatePhotographer #RealEstateVideography #PhotographyBusiness #RealEstateMarketing #Entrepreneurship #OUTWORK
20 Oct 2026
Why PMRE Matters: Brandon Cooper on Business & Building Community in the Industry
What does it take to build the biggest gathering of real estate photographers and media creators in the world? In this episode of OUTWORK, Oliver Ward and Alex Coombs sit down with Brandon Cooper, founder and creator of PMRE — the Photo + Media for Real Estate Conference. Brandon takes us behind the scenes of his journey from real estate photographer and business owner to building a conference that has become one of the most important meeting places for the real estate media industry. We talk about the early days of PMRE, how the conference evolved from a technical photography event into something much bigger, and why community, connection and sharing ideas with other real estate media professionals have become such a huge part of its purpose. We also get into what it actually takes to run a real estate media company while building PMRE, the challenges behind growing both, lessons Brandon has learned along the way, and why he continues putting the conference together year after year. If you’re a real estate photographer, videographer, media company owner or entrepreneur trying to grow a real estate media business, this conversation is a look at the people, relationships and community behind the industry. ABOUT PMRE PMRE — Photo + Media for Real Estate — brings real estate photographers and media creators from around the world together to connect, learn and grow. Learn more about PMRE, the conference, speakers and tickets: https://www.pmreconference.com/ SPECIAL THANKS TO OUR SPONSOR OUTWORK is proudly supported by HDPhotoHub — an all-in-one platform built for real estate media businesses, including online ordering, scheduling, payment collection, media delivery and marketing tools. https://hdphotohub.com/ CREDITS Guest: Brandon Cooper — Founder & Creator - https://www.pmreconference.com/ OUTWORK Hosts: Oliver Ward - https://www.instagram.com/oliwoodmedia Alex Coombs - https://www.instagram.com/alex__coombs Produced by: OUTWORK Topics: real estate photography, real estate media, PMRE Conference, Brandon Cooper, photography business, real estate videography, entrepreneurship, growing a photography business, real estate media business, community, networking and business growth.
14 Oct 2026
We sat down with our competition - and shared our business secrets.
Our first-ever OUTWORK guest! 🍸 This week, Alex and Oliver sit down with Phil Marion, founder of Visual Advantage, one of the longest-running real estate media companies in Canada. Phil started Visual Advantage nearly two decades ago and has grown it into a team of around 20 people — with some photographers sticking with him for 10–15+ years. So we wanted to know: what the hell is he doing differently? Over a few martinis, we get into the stuff that actually matters when you’re trying to turn a real estate photography job into a real business: hiring and keeping great people, separating photographers from editing, scaling without destroying your life, competing in crowded markets, customer service, building systems, and creating a company that can actually operate without you. But the conversation eventually gets bigger than real estate media. How big do you actually want your business to become? When is enough… enough? And what are you building the business for in the first place? Phil has a pretty great perspective on balancing growth with actually enjoying your life — which is exactly what OUTWORK is about. Huge thank you to Big Phil for inviting us into his home, pouring the martinis, and being our first guest. Check out Phil + Visual Advantage: Visual Advantage - https://visualadvantage.ca Follow Visual Advantage on Instagram www.instagram.com/visual_advantage_ca OUTWORK is proudly sponsored by HDPhotoHub Check out HDPhotoHub - https://hdphotohub.com/ OUTWORK is a podcast about real estate media, entrepreneurship, and building a business that actually supports the life you want to live. Hosted by Oliver Ward & Alex Coombs. #RealEstatePhotography #RealEstateMedia #PhotographyBusiness #Entrepreneurship #OUTWORK
29 Sept 2026
We Had an Adult Sleepover… and Things Got Personal
We had an adult sleepover… and things got personal. This week on OUTWORK, we’re finally recording together in person from Oliver’s studio in Muskoka. Alex spent the night, we learned a little too much about each other, and naturally that turned into a conversation about first impressions, money, motivation, ambition, family, business, and what we actually want our lives to look like. One of the things we’re both endlessly curious about is how other entrepreneurs actually live. Not what you see on Instagram. We want to know what your house looks like. What you spend money on. What your morning looks like. What motivates you. How big you actually want your business to become. And ultimately, what are you doing all of this for? We get into our own answers in this episode, including how differently we think about success, growth, money, and the lives we’re trying to build outside our businesses. If you’re a real estate photographer, real estate videographer, real estate media company owner, or creative entrepreneur, this is a different kind of business conversation. Less about cameras and tactics, and more about why we’re building these businesses in the first place. OUTWORK is brought to you by HDPhotoHub — the all-in-one platform built for real estate media professionals to deliver media, market listings, manage clients, and grow their businesses. Subscribe to OUTWORK for weekly conversations about real estate media, entrepreneurship, business growth, lifestyle design, money, freedom, and building a business that actually gives you a life.
24 Sept 2026
I Shoot $5M Homes on an iPhone. Handheld. Here's why.
Can you really shoot a $5 million luxury home on an iPhone? Oliver does—and he shoots his real estate videos handheld. This episode of OUTWORK is brought to you by HDPhotoHub — the platform built for real estate photographers to deliver media, create property websites, and run their real estate media business. In this episode, we break down how to shoot better real estate videos, the simple real estate video formula Oliver uses on every property, and why expensive cameras and gimbals might not matter as much as real estate photographers think. Oliver shares the exact video blueprint his team uses for everything from everyday listings to $5M luxury real estate: the first three shots he captures, how he shoots detail shots, why context matters, and how a repeatable shot list makes real estate videography faster and easier to scale. We also get into: • iPhone vs. mirrorless cameras for real estate video • Shooting real estate video handheld without a gimbal • The 3-shot formula Oliver uses to open every property video • How to shoot luxury real estate without expensive camera gear • Why editing is a superpower for real estate photographers and videographers • How better shooting can dramatically speed up video editing • Creating repeatable systems for your real estate media team • Outsourcing real estate video editing • Pricing and profitability for real estate video • Why clients care more about the final product than the camera you use • AI photo-to-video and the future of real estate media Whether you’re a real estate photographer adding video, a real estate videographer trying to improve your workflow, or a real estate media company trying to scale, this episode is packed with practical ideas you can actually use on your next shoot. Real estate photography is changing fast. Cameras are getting better, iPhones are getting ridiculously capable, AI video is improving, and the barrier to creating great content keeps getting lower. The question isn’t who owns the most expensive camera. It’s who can consistently create great work, deliver it efficiently, and build a business around it. Don’t wanna search Oliver’s instagram for the Video Blueprint Course - link below. https://oliwoodfilms.online/nofuss-video-workflow Welcome to OUTWORK.
18 Sept 2026
We REACT to Upmarket's "Ultimate Betrayal"
If you own a real estate media company and have photographers or videographers working for you, this is probably one of your biggest unspoken fears: What happens if you train someone… and they leave, start competing with you, and take your clients with them? That’s exactly the situation Mark and Reed unpacked on Upmarket’s recent episode, “The Ultimate Betrayal.” After listening, we immediately knew we wanted to continue the conversation. Alex and Oliver get into what this looks like from the perspective of two real estate media business owners who have hired shooters, built teams, lost employees, dealt with competitors—and had team members openly tell them they eventually want to start their own companies. We talk about non-competes, moonlighting shooters, client loyalty, employee culture, protecting key accounts, hiring future entrepreneurs, and the uncomfortable reality that sometimes your photographer has a stronger relationship with your agent than you do. But the bigger question is: How do you build a real estate media company that’s incredibly difficult to compete with? Not because you’ve locked everyone down—but because your systems, service, relationships, culture and brand are so good that clients and employees genuinely don’t want to leave. We also turn the microscope on our own companies and ask: If a competitor wanted to steal our best clients tomorrow, where would they attack? Huge credit to Mark and Reed for putting such a difficult situation out publicly. It gave the entire real estate media industry something worth talking about—and learning from. If you have a team—or want one someday—this episode is for you. OUTWORK — Build the business. Escape the average. This episode of OUTWORK is brought to you by HDPhotoHub — the platform built for real estate photographers to deliver media, create property websites, and run their real estate media business.
9 Sept 2026
Ep2. All Alex's Side Quests Led to This… Here’s How She’d Start Over
Before Alex Coombs built Northern Spruce Media, she did a little bit of everything. DJing. Creative work. Academia. Plans to become a professor. Different jobs, different ideas, and a whole lot of hunger to figure out where she belonged. Looking back, all those side quests were building toward something. In Episode 2 of OUTWORK, Alex tells the story of how she found real estate media and turned that creative drive into a successful business. Then we flip the conversation: knowing everything she knows now, what would Alex do if she had to start her real estate media business again from absolute zero? We get into finding your first clients, what she’d focus on, what she’d ignore, and how she’d approach building the business today. Part origin story. Part playbook for starting over. OUTWORK is about building the business — and figuring out the life you actually want it to create. Supporting Sponsor: HDPhotoHub New episodes weekly.
1 Sept 2026
Ep1. Sharing What We Wish We Knew Before Starting a Real Estate Media Business
Episode 1 — What We Wish We Knew Before Starting a Real Estate Media Business Welcome to the first episode of OUTWORK. Alex Coombs and Oliver Ward have built two very different real estate media businesses. Alex went from shooting everything herself to building a team and an office. Oliver deliberately stayed lean, eventually building businesses in both Canada and Costa Rica around the life he wanted to live. In this episode, we go back to the beginning. Why do so many people get into real estate media and quit? How much does being a great photographer actually matter? When should you make your first hire? And how do you build a business without accidentally creating another job you can’t escape? We talk about our first hires, rejection, customer service, scaling vs. staying small, company culture, AI, the future of real estate video, and some of the mistakes we’d avoid if we were starting again today. We also get into something bigger: what are you actually building all of this for? We’ve taken very different paths, but we both believe your business should be designed around the life you want—not the other way around. If you’re starting a real estate media business, grinding it out as a solo shooter, or already running a team and wondering what’s next, this is where OUTWORK starts. Build the business. Escape the job. This episode of OUTWORK is brought to you by HDPhotoHub — the platform built for real estate photographers to deliver media, create property websites, and run their real estate media business.
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