Sensible Woo is the mind. Sasquatch Media Grounds is the muscle.
Hey Reader,
When this message hits your inbox, I'll have packed my boots and am currently wandering around Austin for SXSW and Podcast Movement Evolutions, where I’ll be hanging out on the creator economy track with the good folks from Podcast Movement and Sounds Profitable.
If you’re attending and you’ve got a conference badge, come say hello at Skybox on 6th.
I’ll be closing out the Futures track on Sunday, March 15 at 3pm with my talk:
“Why Bold Creative Wins.”
The case I’m making is simple: small creators deserve access to real funding opportunities, and monetization shouldn’t be gatekept by legacy media systems.
Stick around after the talk for the final panel featuring one of the founders of Meidas Media, plus the indie podcast awards where Tim Ferriss will receive a lifetime achievement honor.
It’s going to be a big day.
👉 See the Podcast Movement Evolutions schedule
🤝 Catch Up on The Awkward Handshake
While I’m wandering around Austin pretending to be calm in rooms full of podcast industry heavyweights… you can catch up on the show Megan Eckman and I have been building over the last few months.
The Awkward Handshake is our love letter to real-world networking.
Not the stiff “elevator pitch” version of networking. We prefer the human version.
The kind where curiosity leads the conversation, unexpected partnerships form, and you realize the person across the table might become a collaborator, a client, or a lifelong friend.
We talk with founders, organizers, and community builders who understand something powerful: Business is people.
New episodes coming soon feature incredible voices from the Portland ecosystem, including the co-founders of AI Portland and other leaders shaping the local landscape.
👉 Browse the YouTube episode gallery
or
👉 Listen on your favorite podcast app
(And yes, I’ll drop a recent listener review in here because it made my whole week.)
🌍 Your Local Economy Is Waiting
While I’m maxing out my daily step count around downtown Austin and being extra-super-brave networking in the big leagues this week… I want to challenge you to do something a little closer to home.
Go outside.
Talk to someone in your community.
Attend a meetup and introduce yourself to a founder. Show up to something interesting... and *be* interesting for other people to show up for as well.
Two years ago Megan and I started paying closer attention to our own backyard and realized something important:
There is an enormous amount of opportunity sitting just outside your front door.
Your next partnership, client, investor, or collaborator probably isn’t hiding behind an algorithm.
They’re across town. You don't have to dive into the deep end at one of the largest festivals for entrepreneurs. I mean, you can... and if you are in Austin, scroll to the bottom so you can fill out my form and let me know if you want to grab some Torchy's Tacos on Monday morning.
So while I’m roaming around SXSW… you go roam around your city.
And if you're struggling to do that, it's a giant neon blinking sign to register for our workshop on March 28th. More on that when you scroll down... ⬇️
Gossip From the Creator Trenches...
🎬 Ben Affleck’s AI Bet
So now we know why Ben Affleck and Matt Damon made that Netflix movie recently… Ben’s been doing business with them. Specifically, selling his AI production company to Netflix. Before you assume this is another cursed AI content factory (looking at you, Chinese soap opera animal platforms 🐶), that’s not what it is. The tech focuses on fixing production problems in post, turning messy footage into usable scenes without expensive reshoots. Yes, the AI anxiety is real. But let’s be honest… a lot of producers probably wish they’d thought of this first.
🔗 Get your backstage pass
🍑 The “Butthole Logo” Era
Apparently we’re living in the butthole era of AI branding. Someone finally mapped the design evolution of tech logos, and right now many AI companies are converging on the same soft, circular, glowing… anatomy-adjacent shapes. Once you see it, you can’t unsee it. The real lesson here? Startups copy whatever the biggest players are doing visually. Which means half the AI companies launching right now are unintentionally branding themselves like actual assholes. At least it's honest.
🔗 Butt stuff explained
📺 YouTube Is Eating the Internet
Let me plant a flag in the sand for future reference. If you’re not building the foundation of a YouTube channel for your business right now, you’re going to be painfully behind in a few years... and it’ll cost you a lot more to catch up. This isn’t about becoming a Netflix-level creator. It’s about learning the ropes while nobody’s paying attention yet. Publishing imperfectly. Building your library. Because attention is consolidating… and a massive chunk of it is landing on YouTube. Spoiler: TikTok was the appetizer. Follow the money? How about follow the eyeballs.
🔗 See the numbers
🎬 Guess Who’s Back… And the Stakes Are Higher
School of Moxie is back for Season 3.
This time every guest is bringing their comfort show or comfort movie — the one they rewatch when life gets chaotic and their nervous system needs a reset.
But this season isn’t about nostalgia.
Every founder in these conversations runs a business that carries their entire life. Housing. Health insurance. Groceries. Future. No dual-income parachutes floating quietly overhead.
When the stakes are that real, the way someone watches a story tells you everything about how they lead, how they take risks, and how they survive in business.
The trailer just dropped… and yes, Papi Pascal still has a reserved seat in the conversation. 👉 Listen to the Season 3 trailer on your favorite podcast app!
🔥 The Yes Friend Lab Is Live
If you’ve ever left a networking event thinking, “I could’ve said that better…” — this is for you.
On March 28, Megan and I are hosting The Yes Friend Lab, a 3-hour live workshop where we practice the actual skills that make rooms work:
- How to clearly tell people what you do
- How to ask for what you need
- How to offer what you can give
- And yes… the art of small talk
This is not a lecture. It’s reps. Breakout rooms. Real-time coaching. Real feedback.
It’s pay-what-you-can (minimum $97, suggested $197) because we know it’s a crunchy season... and better networking helps all of us win.
If you’re serious about getting paid through relationships, this is where you sharpen the blade.
Stop overthinking the room. Start practicing.
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$97.00
The Yes Friend Lab: March 2026
A 3-Hour Live Networking & Conversation Skills Workshop | Live on Zoom
Saturday, March 28th
10am - 1pm PT (1pm - 4pm ET)... Read more |
🔮 The Fog Is Lifting
Mercury retrograde finally ends this week, and the shift is noticeable.
For the past few weeks many of us have been processing a lot internally. Conversations have required extra patience, plans have needed revision, and emotional awareness has been doing most of the heavy lifting behind the scenes. This week marks the turning point.
The Tarot spread + astrology weather for the week mirror each other perfectly. It reads like people standing in the messy middle of their lives and finally deciding to confront what needs to change. Patterns get acknowledged. Old cycles begin closing. And the next chapter starts coming into view.
I dropped a short excerpt on YouTube so you can feel the shift for yourself. Tap to hear this week's excerpt ⤵️
Want the whole thing?
Inside this week’s reading we unpack the astrology, the full Tarot spread, and the CEO pillars for navigating the transition from processing to progress.
Join the Woo Crew for $7/month and get the full reading, the CEO-level context, and the action prompts that help you move through the week with clarity instead of confusion.
Let's Hang Out
Last call! THIS MONDAY ONLY, March 16th. Are you in Austin this week for SXSW? Could be official, could be unoffocial... I don't judge. I really only care if you like brisket breakfast tacos at Torchy's. If you're going to be in town, I'd like to hang out IRL! This also applies if you know someone you think that I should meet while I'm there, too. You'll find all the info on this form and you're also welcome to forward it to trusted network connections if that is easier. Is it weird that I'm only focused on smoked meats instead of the main stage??
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Participate + Join In
The Creator Economy Dojo ran a killer workshop on 30-second ad spots because monetization is not optional anymore. The March workshop is for members only because we're preparing our sponsor pitch pipelines which builds a critical layer before I start managing everyone's media kits. If your show cannot cover its own overhead, you are bleeding energy into a void. The discipline of building infrastructure is happening now, month by month, brick by brick. Do the work. Get paid. Grow your shit... this year.
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