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Want to hear the recap of the 17th Digital Insiders Mastermind?
๐๏ธI chatted about this to myself on my podcast Million Dollar Grit.๐๏ธ
โYou can listen on Apple, Spotify, or any web browser.
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I just got back from three days in New Haven with 40 of the entrepreneurs in my Digital Insiders mastermind... the 17th one in nine years!
In this episode, I walk you through the three days.
- A keynote from Michael Roderick on aspirational vs. excellence buyers
- Member shares from Emily Green, Amber Housley, Aryeh Sheinbein, and Brittany Long
- A halftime report on what's actually working in 2026
- An afternoon on the Three Overs โ overcomplicating, overthinking, and overfunctioning.
- And a full Get It Done day where we built AI-powered daily sales rituals
The moment that landed hardest for me wasn't a framework or a slide. It was watching one of the most skeptical people in the room (someone who'd been giving me side eye the whole hour) finish building her ritual, run it once, and close a $1,200 sale before lunch. Then another DIer locked down a $5,500 retainer.
Here are the three themes I walked away with:
- Discomfort is non-negotiable. Every success story in that room was a story about tolerating discomfort. The people who win aren't the ones with better strategies. They're the ones who sit in the hard middle without quitting or pivoting.
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- AI is infrastructure, not a project. This is the one I can't stop thinking about. Most people treat AI like a finish line or a bunch of side quests that keep them on the hamster wheel of busyness. We have to stop this or we'll burn out on dopamine.
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- Being in the room matters. Nine years of running this mastermind and I'm still surprised every time. Something happens when 40 people sit in one room for three days that cannot be replicated anywhere else. If you're not currently in or hosting a room, it's worth asking why not.
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Have a great week!
xx Julie
P.S. If you haven't been following the AI & Sheep workshop announcement, I have five spots left for August (the 3rd workshop I put up!). It's a do not miss!
Catch up - AI & Sheep & Important Details about AI & Sheepโ
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