Why You Must Own Your Name Online in 2024

What we talked about.

In this episode of the Sunny Ray Show, host Sunny Ray talks with Ben McDougall, a serial entrepreneur and writer based in the Midwest, about why owning your name online matters heading into an AI driven future. Ben explains the philosophy behind benmcdoo.com as a lifelong home base for his writing, film, photography, and podcasting. The conversation traces his path from a Baptist upbringing in Iowa, through a computer science degree, to founding the Iowa 3v3 soccer tournament and later an esports focused social network. He shares lessons from eight years in web development sales, eight more years doing multimedia marketing for a home builder, and thirteen years volunteering and then leading 1 Million Cups through the Kauffman Foundation. Ben also discusses building an early AI chatbot called Benbot, the failed hardware bet behind FlightBrite that pivoted into a successful app, and how three years of weekly writing became the foundation for his new book with twenty contributing authors. Throughout, he champions a diversified career portfolio over single minded specialization.

A serial founder explains why owning your name online, and staying a polymath, matters more than ever in the AI era.

The questions, and the answers.

What's benmcdoo.com and what are you building there?

It's my home base that transcends whatever quest I'm on, whether writing, filmmaking, photography, or podcasting. I loaded it with experiential wisdom through various creative formats. You can spend time with me there and it's an easy way to connect directly. It's kind of my favorite site.

How important do you think it is to own your name online, especially in this AI era?

I don't love the term personal brand since it's overused, but having that identity and ownership online is important. In web three terms it's read, write, and own. Having a home base and key identifiers you control matters. It's even a fun gift for kids, buying firstname lastname dot com for them before they're born.

What was your childhood like, and what did you want to be when you grew up?

I grew up in a traditional way with a strong sense of family and two siblings. My parents were religious, Baptist specifically, which introduced me to community building. Over time I shifted toward being more spiritual than religious, valuing open mindedness and finding common ground over rigid either or thinking.

How did playing soccer shape the way you build today, starting with the Iowa 3v3 soccer challenge?

I wasn't taught entrepreneurship, but after getting a computer science degree I saw the internet's power early on. I polished a tournament experience I'd enjoyed and executed it as a business, using SEO to find sponsors, eventually selling it to a local soccer club as my first exit.

What pulled you toward computers?

Honestly, video games. At the time being a video game designer, a pro athlete, or now an influencer were the aspirational paths for young guys. Technology wasn't part of our home growing up, but I found a lot of interest in it, and getting a free laptop in college pushed me further toward it.

When did you first feel the pull of AI beyond being a curious technologist?

My senior year AI class was brutal matrix math, thankfully pass or fail. The real moment was building Benbot right as OpenAI's API came online, before ChatGPT was mainstream. We trained it on content I'd written and gated access through NFT ownership so people could interact with it on Discord.

FlightBrite was a hardware bet that couldn't raise capital and pivoted to a mobile app. What did that teach you?

I don't know if it was failure so much as a shift. Hardware is hard, software is magic. Manufacturing cost against quantity put us in a tough spot at a big brewers conference. We'd built strong software underneath, so we pivoted that into an app for beer festivals, and it found product market fit right as the pandemic hit.

You retired from running 1 Million Cups after thirteen years. What does the next chapter look like?

That's a whole other episode. I volunteered five years, then helped the Kauffman Foundation build a role supporting organizers nationally for eight more. I'm not fully sure what's next, I'm letting the new book hit shelves first, but I'm drawn to digitized consciousness and high tech stuff, maybe a twist back into industry.