DissedMedia: A Startup Story Podcast: A Media Buyer’s Lessons on Building a Business from Nothing

I recently had the chance to sit down with Ben Olmos on DissedMedia: A Startup Story — a podcast that documents what it actually takes to build a media business from scratch. Ben has been at it for nearly three years, bootstrapping the whole thing while figuring out what works in a crowded digital landscape. We covered a lot of ground: how I got into paid advertising, what beginners get wrong, how cheap clicks disappeared and what that means now, and where AI fits into running a paid ads business in 2025.

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Introduction

Ben Olmos: Welcome back everybody to DissedMedia: A Startup Story — the podcast where we take you behind the scenes of starting a business from the ground up. Today we’re getting into something vital for every business: how do you cut through the noise? How do you get heard when there’s so much competing for attention?

We’ve tried a lot of things. Some have worked. A lot haven’t. And today I’m talking to someone with serious experience in this space — someone who’s built himself up and helped a lot of other people do the same. Pleasure to welcome Jeremy Yang to the show. Jeremy, how are you?

Jeremy Yang: Thanks so much for having me, Ben. I appreciate the warm intro — I hope I can live up to it.

Ben Olmos: I have a feeling you will. When I started DissedMedia, we had nothing — no webpage, no social following. I didn’t even broadcast it widely at first. I wanted to understand: if you’re a business owner with no voice and no network, is it possible to build from zero on a shoestring budget? Almost three years in, we’re still here. Are we where we want to be? Not quite. But we’re working on it.

Jeremy Yang: I love that. Because honestly, why would you want to put the spotlight on yourself when there are no followers, no views, nothing? That takes real motivation. What drove you to do it?

Building From Nothing: Ben’s Origin Story

Ben Olmos: I’ll give you the quick version. I’ve been in the consumer packaged goods industry for over 30 years. I didn’t have a college degree when I started — I always joke that I passed all my classes on the way to my car. Eventually I went back, finished my undergrad, got the bug, went back for my MBA, then a PhD. And along the way I started teaching.

I was working full-time in consumer goods and doing part-time faculty work. I was brought in to teach social media marketing, which fit my background. But when I got into it, I realised I was teaching a lot of theory and not much real-world experience. I needed skin in the game. That’s really how this started.

Jeremy Yang: Now it all makes sense. You wanted to bring real examples into the classroom — not just textbook stuff.

Ben Olmos: Exactly. And the younger generation wants to become influencers — it’s practically a job title now. Easy to call yourself one, hard to actually do it. I wanted to document what it really takes, for both younger people and older professionals trying to transition into something new. And now I get to talk to really interesting people like you.

Jeremy’s Path: From Antennas to Ads

Jeremy Yang: My backstory is a bit different. I left school — it just didn’t hold my interest. When I was about 21, I bought a franchise and we installed TV antennas. Good business, but there was always going to be a ceiling on it. My dad was a college professor back in China, and I always felt like not finishing school was something I hadn’t resolved.

Jeremy Yang: So when that business ran its course, I went back to university as a mature-age student. I went from $150,000 a year income to zero. I had $43,000 saved up and an apartment. I thought: let’s see how this goes. I did a business degree because I wasn’t sure what I wanted yet. But one subject stood out: marketing. The people around me were terrible at it — they didn’t want to speak, didn’t want to put themselves out there. I saw that as my gap.

I came out top of my class. Perfect GPA, top of the whole year. I thought: that’s it, that’s my transition. But it wasn’t, because even with those results, I didn’t fit the mold of a typical university graduate. I was 35 at the time. I couldn’t get marketing jobs. I applied for paid internships — couldn’t get those either.

The only place that accepted me was a one-year, full-time, unpaid internship. So at 36, I was updating WordPress websites and manually transcribing YouTube videos every day. That was my entry point.

Ben Olmos: That’s remarkable. And humbling.

Jeremy Yang: From there I moved to a paid internship, then started working around marketing companies. One of my managers told me: “Jeremy, if you want results fast, go into paid advertising. Media buying.” I’d never heard the term. When he explained it, I thought: that sounds exactly like me. A year later, my mentor offered to set me up with some starter clients and let me run from there. That’s how Digital Goliath started.

Why Paid Advertising Made Sense

Ben Olmos: Media buying really does tap into the heart of digital marketing. You need two things: psychology and statistics. You need to understand behaviour — how to interrupt someone, capture their attention, and move them in a direction. And then on the back end, you need to analyse the data to see what’s working.

Jeremy Yang: Exactly. You work out what’s clicking — whether that’s the hook, the offer, the approach — and you feed it back into the front end. Then you test again, and again. It’s a loop.

The Early Days of Digital Advertising

Ben Olmos: When you got into media buying, what were some of the early challenges in getting your head around it?

Jeremy Yang: I got into it around 2017, 2018. Back then, digital advertising was still genuinely cheap. People were complaining about paying 85 cents a click. You wish you could get that now.

If you’re getting a good price per click, maximise it until that gap is gone. Because once it’s gone, it’s gone. The same advertisers who were paying 85 cents are now paying three dollars a click and they’re still in business — which means they could have dominated the market back when it was cheap, and they didn’t. Back then it was still cowboy days. These days everything is down to science and there’s basically no open ground left to exploit on the major platforms.

Ben Olmos: Gary Vaynerchuk has been saying something similar for years — it’s dirt cheap, why aren’t you moving on it? He still says it now.

Jeremy Yang: Yeah, for sure. And back then, organic was still powerful too. Hashtags worked, five-day challenges worked, there was real open water to play in. Nowadays organic is so restricted the platforms have basically stamped it out. Which makes paid even more important.

Why Organic Is Harder Than It Looks

Ben Olmos: Organic has been really tough for us. I came into this reading everything about keywords and SEO — optimising every page, thinking traffic would just show up. I was so far from the truth. You’ve got to make sure nobody’s competing on your keyword, that they don’t have higher domain authority, that you’re building backlinks… and even when we did all of that, it barely moved the needle. It wasn’t until we shifted to YouTube and video podcasting that we started getting real traction.

Jeremy Yang: That’s exactly it. Think about a local business trying to compete in a crowded category. There’s a competitor who’s been around for 12 years with someone diligent doing their SEO. That race was lost before you even started. Ads can level that out.

Ben Olmos: The content strategy we’re running now is long-form podcast for depth, two-minute clips for broader reach, and medium-form YouTube videos. Each platform has its own format and you have to respect that.

Jeremy Yang: Native to the platform. Always. And consistency matters more than most people realise — even when you don’t see results, you keep doing it.

What New Advertisers Get Wrong

Ben Olmos: When people come to you who’ve never run ads before, what are the most common misconceptions?

Jeremy Yang: The first thing most beginners focus on is the mechanics. Which campaign type? What structure? How do I set it up? That’s not where the needle moves.

What they should be focused on is creating an offer that cuts through. If you can nail that, the technical stuff largely takes care of itself.

The second big misconception is around targeting. People think platforms can zero in on a CEO, or target only pregnant mothers shopping for baby products. That’s not the world we live in anymore. Privacy changes have made audiences very broad. So if you can’t rely on the platform to narrow it down for you, you have to call out your audience’s deepest problem right at the very start of the ad.

Ben Olmos: You mentioned the ICP — the ideal customer profile — and I know that comes up a lot in marketing teaching. How much weight do you put on it?

Jeremy Yang: ICP is useful as a starting point, but it’s theoretical. You won’t really know your customer’s pain points until people are voting with their wallets. Waitlists, surveys, personas — they give you a hypothesis. Real customers give you the truth.

So rather than spending months perfecting your ICP, put things in the market and test. Run different offers, different hooks, different framings. The one that gets traction tells you more than any persona exercise.

The example I use: imagine you’re an accounting firm. You could run one ad that says “accounting services.” Or you could run five ads, each speaking to a different niche — digital marketing agencies, ten-person teams, eCommerce brands. You’re the same firm. But for each ad, you’re talking directly to one type of person, and that person thinks “that’s for me.” That specificity is what gets the click.

Testing, Patience, and Putting Yourself Out There

Ben Olmos: One thing I’ve noticed is that people hesitate to put things out publicly because they’re afraid of looking foolish. I’ve let go of that entirely. I’ve had content I thought was really strong get nothing, and stuff I thought was silly do really well.

Jeremy Yang: That’s so true. The clients who’ve been doing ads for years — they know they need to turn it up when they go live. They lean into being more animated, more direct, more themselves. The fear of looking bad on camera is real, but it’s a bigger obstacle than most people admit.

Ben Olmos: Fail in public. Who cares? Nobody gets it right first time. I did ten book promo videos recently. I scripted them, got the words right — and they were awful. They sounded like a presentation, not me.

Jeremy Yang: Authenticity is the thing you actually can’t fake. And the charlatans — the ones promising to make you famous for a large upfront fee — they’ve always been there. I saw it firsthand when I started in 2019. Clients with fake social proof notifications. No one in the room but the alert kept firing. I was sitting in the back thinking: there’s no one there.

Building the Business and the Team

Ben Olmos: You’re not just running ads — you’ve built a whole company around this. What are you most proud of?

Jeremy Yang: A couple of things. First, I’m currently the most recommended specialist in Australia in this space — Google Ads and Facebook Ads. That was a real milestone.

When I started, I looked at the traditional agency model: salesperson, account manager in the middle, then an outsourced team doing the actual work. That account manager layer is overhead — and it creates distance between the specialist and the client. I cut that out. I hired directly from the Philippines, built a team of ten full-timers, and every client works directly with the person doing the work. It’s a big part of why our results look the way they do. If you’re curious how the shift from full-service agencies to specialists is playing out across the industry, we wrote about that recently.

What makes me proudest though is something that happened early on. One of my early employees came up to me and said, “I just got air conditioning.” I thought there was more to the story. She said: “I’ve never had air conditioning before.” That’s when I understood what kind of company I actually wanted to build.

People on my team are putting siblings through university. They’re improving their families’ lives. That matters to me far more than the agency ranking.

And then recently — the business has been running for seven years, many of the team have been with me for five — I finally went to the Philippines for the first time and met them all in person. We rented a villa, shot some photography together. That was a big moment.

Ben Olmos: You said “what do I have to share?” and then in the same breath told me you’re the number one recommended person in Australia in this space. You can’t have nothing to share and also be at the top of the field.

Jeremy Yang: Fair point. I suppose I undersell it sometimes.

AI, Automation, and What Doesn’t Get Replaced

Ben Olmos: AI is reshaping the work landscape fast. There are things you used to struggle to get insights on that tools like Claude or ChatGPT can produce in seconds now.

Jeremy Yang: I wouldn’t have dreamed of it a few years ago. And here’s what I’d add: because AI is now available to everyone — including competitors — we’ve had to raise what we offer. Things we would never have touched before, we now do proactively, because we know a competitor could spin it up overnight. We had to move first. It’s something I touched on recently in our piece on what the AI wave actually means if you’re good at this.

Ben Olmos: A small business with five employees can now operate like an 800-person company because of what automation is running in the background. It’s completely changed how people compete.

But here’s the thing — the reason I put myself out there, put my personality on camera, share my mistakes publicly — is because I think that’s what wins in the long run. Authenticity. People want to connect with a real person. As it becomes easier to hide behind a digital curtain, the people who show up in the open will stand out more, not less.

Ben Olmos: The biggest struggle I have with students right now is that they’re leaning so hard into AI that I don’t know what their voice is anymore. Because I’ve been teaching for 20 years, I know what student writing looks like. But over the last two years, everyone sounds the same. I pull up their discussion answers in class: here’s one, here’s another, here’s a third. Identical. And the problem is that AI is giving everyone the same voice, the same resume, the same cover letter. Your value is in showing people what you know.

Jeremy Yang: They need a playbook. It’s not enough to say “you need to stand out” — they need to know what standing out actually looks like, and what specifically AI and offshore teams can’t replace. That’s the exercise worth building.

Closing

Ben Olmos: Jeremy, this has been a genuinely good conversation and I feel like we’ve only scratched the surface. We need a part two. Before we wrap — where do people find you?

Jeremy Yang: The easiest way is LinkedIn — search Jeremy Yang, easy to find. I read and reply to everything. And if anyone has a podcast covering marketing, small business, or advertising, I’d love to be a guest.

Ben Olmos: Check out Jeremy Yang and Digital Goliath. And for everyone following along with DissedMedia — we’re on a mission to hit 100,000 subscribers by end of 2026. Tell your friends. Tell your enemies — they’re more likely to actually do something with your words.

Key Takeaways

• The offer beats the setup. New advertisers waste time obsessing over campaign structures and targeting settings. The thing that moves results is having an offer that clearly speaks to a real problem. Nail that, and the technical decisions become much easier.
• ICP is a starting point, not the answer. Ideal customer profiles are useful theory, but customers only reveal their real pain points when they vote with their wallets. Get something in front of real people and let their behaviour tell you what’s working.
• What you can’t automate is the thing worth building. AI can produce content, code, and analysis at scale. What it can’t replicate is a genuine point of view, built-up experience, and a real relationship with an audience. That’s the asset worth investing in.
• Build for the people doing the work, not just the clients paying the bills. Jeremy’s proudest moments aren’t the rankings — they’re the team member who got air conditioning for the first time, and the siblings being put through university. Sustainable business is built on that kind of buy-in.

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