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Jenny 5x'd her revenue goals after leaving Google, and now her husband Jon is about to quit his steady nonprofit job to join her business full-time as Director of Brand Partnerships. They're terrified and excited in equal measure.
Here's what we cover:
Why Jenny's first $6K brand deal almost caused a marriage fight (and what it revealed about trust batteries)
The "beneath you" trap that kills couples who work together—and how to avoid it
Why betting on one business with multiple revenue streams is actually safer than a single 9-to-5 paycheck
The critical mistake I made when I first quit my job to work with April (don't kick down the door)
How to prevent work conversations from bleeding into every moment of your marriage
Jenny landed her first deal during the 10K Challenge with a 100% conversion rate. But the real test isn't closing deals—it's whether Jon and Jenny can build this thing together without destroying their relationship in the process.
Follow our guest(s): - https://itsjennywood.com/
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Chapters:
0:00 - The Decision: Should Jon Quit His Job?
0:49 - From Google Executive to Wild Courage Author
2:36 - Why Jon Wants to Bet on Jenny
4:25 - The Fear Everyone Has About Career Gaps
6:50 - My Biggest Mistake When I Quit My Job
8:49 - Is Brand Partnership Work Even Enough?
9:48 - Sponsor Games 2026 Announcement
11:46 - The First Fight Over a $6K Brand Deal
14:46 - Trust Battery Drainers vs. Builders
15:54 - When Work Never Stops (Marriage Boundaries)
16:54 - The "Beneath You" Assumption Trap
18:31 - Why Multiple Revenue Streams Beat Job Security
20:07 - Don't Assume Your Partner's Limits
22:15 - Revenue Streams Will Swing Wildly (And That's Normal)
23:46 - Say It In The Moment (Don't Let It Build)
24:29 - Decision Made: Jon's Quitting
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