Navigating Life After a Startup Sale

Once upon a time, when MTV played music videos, their more mature sister channel, VH1, had a show called “Where Are They Now”. The idea behind the show was to track down notable artists of previous generations to see where life had taken them once they’d stepped out of the spotlight. 

OK boomer, what does this have to do with the indieverse specifically, and the culture of technology more broadly?

In most creative fields, whether it's art, fashion, architecture, etc., there's a deeply held sense of respect, even reverence, for the innovators who came before. The breadcrumbs of insights and artifacts or creation serve as a foundation of reference points for those who come after. 

But tech, as a creative field, feels different. Always forward, never back. There's frequently disregard, even contempt, for the innovators who came before. 

I often say we have the raw materials for any number of possible futures. Breakthroughs in AI, energy, chip design, crypto, biology — the future has never been brighter. As excited as I am to charge forward, I thought it would be valuable to look back. 

When I entered the venture market, it was in the wake of the dot com crash. Shortly after, my partner, Tim, popularized the term Web 2.0. Then, as now, there was a deep sense of hope starting to swell in technology. There were lessons to draw from and infrastructure to leverage to build upon, in addition to a renewed sense of optimism for the role technology could play in our lives. 

As we enter a similar moment in tech, I wanted to return to some of the innovators of Web 2.0 to see if there were any lessons to glean from their experiences, and to celebrate their contributions to the progress we're building on now. 

The first of these came up in our conversation with Charles from Are.na earlier this year. He and his team and had drawn inspiration from a popular Web 2.0 called Del.icio.us, known primarily as a shared, social website bookmarking service. I have known and respected its founder, Joshua Shacter, for years. We decided to trek to Mountain View for a catchup with Joshua on his past learnings and current projects. 

Joshua built Del.icio.us as a side project while working at Morgan Stanley, evolving it from his earlier project called Meme Pool. He didn’t set out to build a startup - it was simply a tool to manage his own bookmarks that grew organically to millions of users. Within less than a year of raising funding from Fred Wilson at USV, Del.icio.us was acquired by Yahoo, where Joshua experienced the challenges of corporate bureaucracy and struggled with the loss of control over his product.

The Web 2.0 era allowed for more experimental approaches, whereas today’s entrepreneurs are highly focused on specific business opportunities, particularly in areas like AI tooling for business functions. Joshua believes that the current AI revolution has reset computing to a pre-6502 type era where fundamental architectures are still being determined, making it an exciting and challenging time for founders who need to balance innovation with market demands.

When investing, Joshua looks for founders who are perpetually unhappy with their tools and constantly seeking improvement. He prefers to invest in weird ideas that make him think, “I never would have thought of that”, rather than incremental improvements to existing solutions. His approach is fundamentally engineering-driven, and he values founders who can engage in deep technical discussions.

This one was a ton of fun. It's a new format for us, so be gentle with the feedback. We’ve already learned so much and hope to improve on it. We have a few more of these in the can and a few more lined up for the new year. If there’s someone you’d love to see us catch up with, shoot us a reply with suggestions. 

As always, if you or someone you know are working on something that could be a fit for the indieverse, we’re always on the hunt for our next investment. 

Finally, from all of us to all of you, wishing you the happiest of holiday seasons.