I Quit Tommy Boy Records to Start a Dot-Com—and 27 Years Later, I’m Reinventing Myself Again

In 1999, I did something that probably sounded crazy.

I left a secure job at Tommy Boy Records to start an internet company.

I had a salary, benefits, and a position at one of the most respected independent record labels in the music business. I could have stayed and continued building my career there.

Instead, two of my coworkers and I decided to take a chance.

This was right in the middle of the dot-com boom. We believed the internet was going to completely change the music business, even though none of us knew exactly what that future would look like.

So we started a company called Takeoutmusic.com.

The idea was to give independent artists and record labels a way to promote and sell their music and merchandise online.

Remember—this was 1999.

There was no Spotify.

There was no iTunes Store.

There was no TikTok, Instagram, or YouTube.

The digital music business we know today didn’t exist yet. Artists still depended heavily on record labels, distributors, radio programmers, DJs, record stores, and traditional media to reach an audience.

But we knew something was changing.

So we took the chance.

That little idea eventually became a real company. We built a team, worked with artists and labels, and even took the company public.

More than two decades later, I find myself facing another major shift in the music business.

Today, independent artists can finish a song, upload it, and make it available around the world almost immediately. The barriers to releasing music have nearly disappeared.

But access and attention are two completely different things.

Putting a song on Spotify doesn’t mean people are going to find it. Streams alone aren’t a marketing strategy.

Artists now have to understand content, advertising, social media, audience development, and data. We also have access to artificial intelligence and other tools that would have seemed impossible when we launched Takeoutmusic.

With my new song, “I Surrender,” I’ve been learning how to use those tools.

I’m running Meta ads, studying my Spotify data, testing different videos and audiences, and using AI to help me understand how people are responding to the music.

AI didn’t write the song. It didn’t replace the singer, producers, or creative process. It helps me analyze what happens after the music is released so I can make better decisions.

The more I thought about it, the more I realized that this isn’t the first time I’ve had to reinvent myself.

In 1999, it was the internet.

Today, it’s algorithms and AI.

At 56, I’m learning new tools, trying things I haven’t done before, and figuring out the next chapter as I go.

Maybe I’m not really starting over.

Maybe reinvention is simply part of who I’ve always been—someone who gets comfortable and then leaves anyway.

I still don’t know if that’s brave or just restless.

But 27 years later, I’m doing it again.