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Ecomm Cowboy Talks AI and Underdogs


Chris Hall is an ecommerce entrepreneur turned media operator. His new “Ecomm Cowboy” show broadcasts live Monday through Friday on X and YouTube. The mission, he says, is twofold: deliver daily news to sellers and offer companionship to those working alone.

Chris first appeared on the podcast in 2023 as the marketing head of a D2C brand. In this our latest conversation, he addresses his goals for Ecomm Cowboy, production challenges, and, yes, the power of AI tools for one-person brands.

Our entire audio is embedded below. The transcript is edited for length and clarity.

Eric Bandholz: Who are you and what do you do?

Chris Hall: I’m the founder of Ecomm Cowboy, a startup media company broadcasting live Monday through Friday on X and YouTube. We talk about the current and future state of ecommerce so operators can survive and thrive. I launched the show about a month ago.

I stumbled into ecommerce in 2014. I created one of the first subscription coffee brands on the internet.

After that, I worked for a marketing agency and then with Bruce Bolt, the D2C athletic glove company.

Bandholz: What are your goals for Ecomm Cowboy?

Hall: I’ve contemplated the concept for years, with two missions.

First, ecommerce owners are on the bleeding edge of the ever-changing internet. We cover the top news stories, retail developments, direct-to-consumer topics, artificial intelligence — anything related to selling online.

Second, working from a laptop at home is common in the ecommerce industry, but it’s intensely lonely. For many, it’s a dreadful experience. So I hope Ecomm Cowboy is also a place where people can have a companion of sorts and interact.

Bandholz: A daily show with guests is a lot of work.

Hall: Yes, it is. We usually have one guest, but sometimes it’s two. Each show runs an hour. I hope to extend it eventually to two hours.

I prepare for three to four hours each day, covering everything that’s happened, who’s appearing, and what to discuss. Plus events occur in real time that alter the plan.

After each show,  there’s editing, cutting, and posting to make the most of the content. So it’s a lot of energy and time, but I love it.

I thrive on the pressure. There’s much to do every day before noon Central time, when the show goes live.

It brings me back to my time playing football at the University of Texas, where every practice I had to be ready to battle,  mentally and physically. A part of me still welcomes the challenge. I wake up excited every day because of it.

Bandholz: What’s the state of ecommerce?

Hall: AI tools are jaw-dropping. Six months ago, we were laughing at them, but no more. AI can now perform tasks such as ad creation, empowering what I call a one-person brand.

Sean Frank of Ridge, the wallet maker, calls it Ecommerce 4.0. It’s an opportunity for underdogs. One person, harnessing today’s tools, can do what took an entire team five years ago.

A good example is Kive, an AI tool that generates product specs directly within the image. A recent guest, Bart Szaniewski from Dad Gang, a D2C hat seller, described the tool. He uses the images on his Instagram feed.

Bandholz: If you can’t communicate in today’s world, you will be left behind.

Hall: That’s fair. The most adept operators are communicating (in ways I have yet to take advantage of) using AI tools that produce a voice, a video, a copywriting style.

I see two routes going forward. There’s the anti-AI bet. The best way to be anti-AI and build trust is to be live and in person. Be an actual human who’s making mistakes and producing something good enough that people will come back.

The second route is to stay at the forefront of AI technology and become expert on the tools and methods. If you can win visitors in a way that doesn’t deceive them, there’s a way to enrich yourself.

On a recent show, we touched on an app called DramaBox. It produces AI-generated TikTok-style mini dramas. Each episode is literally one minute long. I’m told the business is booming from selling access to the shows. Viewers download the app, pay, and then consume the content.

To me, it’s horrible for humanity, although I use an AI-powered video maker from ByteDance called Seedance 2.0. A number of popular videos use Seedance, such as Ethan Hunt from Mission Impossible.

Many observers say Hollywood is obsolete, a step behind. I don’t know about that. But what I do know is that the capabilities are better than ever.

And now it’s up to us. How can we use the tools to improve what we talk about or solve a problem for them?

Bandholz: Where can listeners watch your show, follow you, or get in touch?

Hall: The show “Ecomm Cowboy” on X and YouTube. I’m also on X or LinkedIn.



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