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David reflects on the advantages of creators over traditional media, tips for founders, and hard-won lessons.

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David Segura has been a driving force in the media space since founding Giant Media, which was later acquired by Adknowledge. To fuel the creator economy, David has also been an angel investor in over 70 companies and founded Glassbox Media, a premium podcast creator platform. Today, we’ll focus on his vision of what it means to build a media empire from the ground up. 

Launching Giant Media

Prior to Giant, David created a short-lived business called Dorsia Media, which involved starting and buying Facebook pages and using them to promote content. When Facebook changed its terms of service, it became irrelevant overnight.

So, he decided to create Giant Media, then quickly scaled it up. “We had a very simple vision: We thought if we work with amazing brands, and in some cases, content creators, distribute their content … hopefully make it go viral, we could build a significant franchise.”

Not everyone saw it as a wise idea. “There were very, very smart people that were absolutely 100% certain that Facebook was a fad, would never be a large, legitimate business, and they advised us not to bet the ranch on it. What they didn’t realize is not that we knew more than them; it’s that we had no other choice.” 

They knew that Facebook wanted people to innovate in a way that it could monetize, so they baked that into their plan. They leveraged publisher connections from his previous roles, like and Funnier Guy. Soon they’d grown a significant business while enjoying every moment of it.

Lessons from Giant Media’s acquisition

Giant Media was the first company David had ever sold. While there were ups and downs, it gave him the freedom to travel and the luxury of more time, he says. 

Of course, it was an adjustment: He was no longer in control, though they consulted with him heavily to grow their video business within the larger conglomerate.

But they were patient with those going through that transition, and it was a great learning opportunity. “The two years that I was there post-acquisition, I soaked up as much information and experiences as I could,” he notes. 

Advice for newer entrepreneurs

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David shares some words of wisdom on getting started in the media space—and much of his advice applies to any new entrepreneur.

Laying the foundation

Despite the popular media narrative of just launching right in, most successful entrepreneurs keep their day job for a while, David says. “Almost everybody starts as a side hustle or a fun labor of love—and then suddenly, through hard work but honestly, a lot of luck, it becomes a business, and it becomes suddenly scalable,” he asserts.

That’s true for many influencers creating short, shareable “bites” on platforms like TickTock, as well as dedicated podcast hosts working in a more episodic fashion, he notes. “What most of them have in common is that they started out as very passionate hobbyists, and then, only over time … did it suddenly become a business,” he says. “They suddenly realized there’s actually a huge market for this, I like doing it, and it’s actually working.” 

Do what’s right for your mental state as well as financial situation, he urges. Lay the foundation steadily, then jump in with full force when you’re ready.

Finding your niche

Growing an audience is tough, he acknowledges. People always ask if what they’re passionate about is relevant and has a market. “And the short answer is, probably,” he says. “What all of these folks have in common is, they have a very quirky, unique, personalized way of doing something,” he says, speaking of Glassbox Media’s podcast creators. From examining crime cases to philosophy, their podcasters all bring a distinct flavor and perspective.

Being accountable

Early on, new founders have no board or hands-on oversight, David notes. “But what if there was?” he asks himself. How would he position an idea to his imaginary board and explain why he’s doing it? He’ll question his own decisions, running through a conversation with an imaginary investor. By pushing him to consider different stakeholders’ perspectives, this makes him a better entrepreneur.

“One thing that investors bring to the table that is very clarifying and helpful is that they have this really big, abstract point of view,” he says. “It basically makes you do things that are very scalable, it makes you do things that are repeatable, and as a consequence of that, I think it’s a very good clarifier.” So, he has investors for goal-driven rather than financial reasons now.

Growing Glassbox Media

After becoming a prolific angel investor, the pandemic pushed him to get back into entrepreneurial work. By 2021, he and a group of folks from Giant ultimately decided to focus on podcasts. Through iteration and testing, they defined their space and model. They didn’t want to be an ad network, nor did they have producer skills, so they couldn’t build something from scratch.

Ultimately, they carved out a space of their own, promoting up-and-coming podcast creators. The premise? “Let’s go out and engage star creators that are already doing well, that have already built a great business, but essentially offer them not only amazing financial terms but limit some of their downside by making a guarantee,” David explains. “Then, in exchange for that, we’ll get exclusivity, we’ll host all their content catalog in our own platform and own environment.” At the same time, they leveraged their extensive understanding of technology and advertising to automate ad reads. Ads aren’t baked into the catalog, so they can change them out once a campaign wraps up.

Like a record company, they also invest in their creators. They become a minority owner in the podcasts on their platform and work hard to support them.

While it would be tough to take on big distributors like Spotify and Apple, they launched a media empire in their own right by focusing on the content space. Podcasting is just getting started, they believe, and it has much to offer as a source of other types of investment—from TV show adaptations to live events. “That’s why we think bundling the best with the best is the right way to actually build meaningful scale and basically help solve problems for people like Spotify and others,” David asserts.

Advantages of creators over traditional publishers

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Creators have some real advantages over more traditional publishers, David emphasizes. “The one thing is that it’s more efficient and lean. In other words, you can basically start a media company in a very simple fashion. You get some equipment—some very basic tools of the trade—and you can go from there.” With the low investment, you can use trial and error to get started.

Creators and podcasters are producing quality content right in their homes, he asserts. “They’re doing incredible, world-class content from their living room, their bedroom, and that would have been unthinkable back in 2014,” he says. “You just wouldn’t have believed that quality content, that literally millions of people would want to consume, could be done so efficiently.” 

Twenty or even 10 years ago, you needed a substantial amount of investment for businesses that you now can start for $20 on the weekend, Freddie says. Today, you can produce an HD or even 4K-quality production, sharing it on multiple platforms in real-time, assisted by tools that make it feel like a 20-person team created it. You’re only limited by talent and time.

Plus, consumers love the authenticity of personal stories, David emphasizes. Live shows are growing popular, and people are single-handedly starting media organizations.

Creatives who are adaptable have an advantage, too. Many of his contemporaries are set on imposing outdated best practices on this new era of creators, but in reality, you need to be ready to radically evolve.

Why he’s passionate about angel investing

David is an incredibly prolific angel investor, having contributed to the growth of 70 companies. He began by investing in close friends, then branched out to acquaintances, varying his strategies. 

He got started because he wanted to live vicariously through other founders, experiencing the excitement of getting a new project off the ground. Early on, people need input from trusted sources to solve the numerous challenges that arise. But he’s careful not to overstep, knowing the project needs to follow their vision.

“I like problems. I think that too many entrepreneurs get scared and think they’re to be avoided,” he says. “There’s no upside without tremendous risk.” For him, the early stage—with all its hurdles to surmount—is the most exciting part. 

Oh Ship! Moments

Just over a decade ago, Giant was doing a major campaign with Nissan that involved making and distributing one- to two-minute videos. Their PR staff would encourage media outlets to cover these stories in an effort to make the videos go viral through earned media. Importantly, they never paid the outlets to do this. They did, however, pay a young freelancer to seed the campaign by reaching out to platforms he had relationships with. Because the freelancer worked for AOL, they told him not to pitch that outlet. But the freelancer ended up pitching his AOL colleague, who covered the story.

“Nissan understood the situation, but the truth is sometimes different from the optics. So they were kind of irate,” he says. But they immediately worked out a plan with Nissan, who later told them they decided to continue the campaign because of their strong accountability.

“You always have to tackle a problem; it doesn’t get better with time,” David learned. “Now, I have enough humility to recognize I don’t control the outcomes; I control the inputs and the process, and if you maximize those things, good things will happen more often than bad.” 

Find David on LinkedIn or @DSeg10 on Instagram. And be sure to like and follow us for more inspiring content!


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