A year ago, The Daily Whatever Show was a lark. Two longtime friends deciding, almost on impulse, to go live every morning and see what happened. No real plan beyond “this could be fun.” Maybe a few dozen people would watch. Maybe it would fizzle out.
Instead, Lawrence Winnerman and I built something real.
Not just a show—but a room. A community. A refuse in very dark political times A place where people show up every day not just to listen, but to talk to each other, challenge each other, comfort each other, and occasionally laugh at whatever absurdity Lawrence and I have gotten ourselves into that day.
So for our first birthday, Lawrence suggested we… do nothing.
Obviously, being the true Leo I am, I ignored that.
I booked a two-hour online extravaganza because when it comes to hosting parties (and podcasts), my ethos is: there’s always room for more friends.
Over two hours, the show turned into exactly what I wanted it to be—a rotating, slightly chaotic, deeply human cocktail party where brilliant people dropped in, met each other for the first time, and immediately started having real conversations.
We had journalists. Creators. Political strategists. A feminist writer calling in from Dubai under a pseudonym for her own safety. A sock puppet turned real boy. Old friends. New voices. And yes—at one point, a sitting U.S. Senator in a jaunty hat singing us “Happy Birthday,” which is not something we could’ve imagined in our wildest dreams.
But what struck me most wasn’t the guest list. It was the throughline.
Every single person who came through that show is part of how this thing exists.
Some helped us at the very beginning, when we had maybe five people watching and were just trying to figure out how Substack even worked. Some are part of what’s happening now—new voices growing fast, pushing conversations forward, making this space sharper and more interesting by the day. Some are just… there. Every morning. In the chat. Holding the whole thing together in a way Lawrence and I never could on our own.
That’s the part I keep coming back to.
We didn’t just host 250+ shows this past year. We didn’t just book incredible guests or stumble into conversations that somehow matter more than we expect.
We found our people.
And in a year that has been, by any reasonable measure, a lot—politically, culturally, personally—we built a space where those people could show up and not feel alone in it.
That’s the win.
So yeah, we celebrated. Loudly. The hugest of thanks to all of our guests who showed up today: Aidan Wharton, Anne P. Mitchell, Esq., Grounded Podcast (Maritsa Georgiou & Senator Jon Tester), Jason Odell, Julie Roginsky, Karen Marie Shelton, Letters from a Feminist, Libbie Grant, Marlon Weems, Nick Paro, Ossiana Tepfenhart, The Opinionated Ogre, Walter Rhein, Yanni Hamburger, and Zev Shalev.
A special shoutout to Karen Marie Shelton, who is not only our amazing moderator but who also has never, ever missed an episode of TDWS—and to Walter Rhein for being the first-ever guest on TDWS, 364 days ago. And also because he wrote us this epic poem!! Tune in around the 61 minute mark to hear Walter read it—call and response and all!
And if year one looked like this—if this is what happens when you say “what if we just try it?”—then who even knows what year two will bring?
We just know we’re not doing it alone…
Thank you Walter Rhein, Mr. Troy Ford, Dr. Amber Hull, Beth Cruz, Harry Hogg, and so so so many others for tuning in.
WE LOVE YOU ALL, MEAN IT!
PS - Our First Birthday Party Annual Subscription Discount is still in effect through the weekend. Subscribe for just $24/year!
