OUTWORK

Oliver Ward
  • 5.0 (1)
  • Entrepreneurship
  • Updated Weekly

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.

Episodes

  1. Sep 29 ·  Video

    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.

    We Had an Adult Sleepover… and Things Got Personal

  2. Sep 24 ·  Video

    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.

    I Shoot $5M Homes on an iPhone. Handheld. Here's why.

  3. Sep 18 ·  Video

    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.

    We REACT to Upmarket's "Ultimate Betrayal"

  4. Sep 9 ·  Video

    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.

    Ep2. All Alex's Side Quests Led to This… Here’s How She’d Start Over

  5. Sep 1 ·  Video

    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.

    Ep1. Sharing What We Wish We Knew Before Starting a Real Estate Media Business
  • 5 Episodes

About

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.

Information

  • Creator
    Oliver Ward
  • Years Active
    2026
  • Episodes
    5
  • Rating
    Explicit

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