Life After Indie

“So… what are you up to now”?

A frequent question that I’ve been awkwardly answering for the last year. At various times the answer to that question has been more certain than others- making investments, talking to other funds about joining them, talking to folks about joining us, starting an Indie DAO ;-)

After over a decade of professional dubs, the L of Indie hit me hard.

Harder than I could have imagined or planned. We talk about failure. Sometimes even lionize it. But that doesn’t take away from the sting and self-doubt it seeds. I felt like I’d let everyone down- myself, my family, my team, and the founders who’d taken a risk on the Indie model and invested so much of themselves into proving out the model.

And then there’s the feeling of letting down Indie itself which I viewed as far more than a fund or a strategy but a new kind of ecosystem and economy. What I started as a small experiment had infected me. It consumed my thoughts, my nights, and my days. With each iteration, the vision became clearer, the mission more expansive, the momentum more palpable.

Right up until we turned off the lights.

I beat myself up for a long time.

Eventually, the woe is me’s became the what is nexts. And that’s where I’ve been spending the vast majority of my time.

Shortly after The End of Indie announcement, I quietly closed a new fund under the OATV banner, our fifth fund. It’s around $20M, mostly my money with a couple family offices and one large foundation joining, each of which I’ve worked with over many years and multiple funds.

It’s just me and there’s no predefined strategy; rather, it’s intended for an exploration of strategies, structures, and deployment models.

In the last year, we’ve made just over 20 new investments (my version of eating my feelings, apparently), most in the engagement mode of an angel investor with check sizes ranging from $50k to $1M.

But me writing angel checks isn’t the end goal. The ultimate goal is to find a scalable strategy to build the next chapter of my investing career around. Given the dynamism in venture right now, there’s no shortage of surface area for new strategies to explore and new experiments to run. And who knows, given the progress we’re seeing in the Indie portfolio, maybe there’s another bite from the apple there too.

Anyway, I guess that’s my publicly awkward way of answering what I’m up to now.

Stay in touch or get in touch if you have something we should be working together on…