Twenty years ago, I was about to pitch LinkedIn’s Series B to Greylock and other investors. I remember going through slides at Starbucks, equipped with a PowerPoint deck, a game plan for growth, and what I thought was a solid pitch. But there were, of course, challenges and uncertainties to address. More than just building a company, our team was trying to create a category. Some were calling us "Friendster for business," but the concept of professional networking was more or less untested. Our pitch deck had a vision I believed in deeply—enough to stake my career on it—but that didn’t make it easy. Knowing what I know now, what I would tell myself back in 2004, during that pivotal moment for me and for LinkedIn? What advice would I give younger Reid? What reassurances or warnings would I deliver?
I’ve created a new Reid AI—20 years younger—to pitch the real, present-day me on the 2004 LinkedIn plan.
To clarify: What you are watching is an attempt to use the latest AI tools to replicate some of my younger self’s curiosity and revisit an exciting moment for the company I co-founded—which is also an interesting test of how this technology can be used more generally. When we created “Reid AI”—my present-day avatar—a few months ago, we did so by training it on 20 years worth of books and interviews. We had a 4K video interview to train a video model, and we were able to use voice replication tools to replicate my voice.
To create Reid AI 2004, my team had to get creative. It’s a custom GPT trained on knowledge up to 2004, including my own writing. Using Hedra, UNSHUT, and other tools, we relied largely on an image-to-video process that doesn’t require any training video but can generate video from AI-generated images.
Overall, hearing myself pitch LinkedIn to myself was a bit surreal. I remember that early entrepreneur. This conversation between past and future selves feels not only like a reflection on how much has changed, but also on what remains constant: The core values of trust, integrity, and community that were pivotal in some of the startup's earliest pitches remain at the heart of LinkedIn today.
I believe I would still invest in that idea. But I'm also amazed by how much 2004 Reid is about to see the world and technology change.
What do you think? What would you tell the younger you from a decade or two ago?
