Good morning 👋
And Happy New Year!
Some of you have been reading this newsletter since 2020, and you have seen the full arc of starting as a Notion doc → starting a podcast → realizing newsletters are better businesses → creating services on top of the newsletter → launching a fund that sits on top of this ecosystem we have created.
Every year for the past five years, we have shared an annual update. We do this because we believe that building in public is an asymmetric bet. We do this so that all of you can stay on top of what we’re doing, but also so that the experiments we run while building can be useful for others thinking through the same things.
2025 was a difficult year.
The media business continues to compound, but we have had to think creatively of where we want to take it from here.
The old newsletter playbook is not relevant in today’s world, advertising is not nearly as lucrative as it once was, and as a media operator, the bulk of your time is now spent thinking through ways to increase the lifetime value per subscriber. How well you do that is the difference between massive success and closing your doors.
I started Outlaw last winter, and I have spent most of the year fundraising.
Something that you don’t realize until you set out to raise money yourself is that fundraising is hard - mentally, physically, and emotionally. I wouldn’t be doing this if I didn’t think it was worth it in the end, I am now in a much better spot than I was last year, but 2025 was a year of getting my teeth kicked in.
Below the Confluence annual notes, I have shared the annual letter I am sending out to all of my LPs for Outlaw.
Hopefully, you find something valuable in here.
P.S. This is a long one and will get clipped by Gmail.
If you want to read the full letter, click the button above.
