Jenny pitched one brand. Landed a $6,000 deal. First pitch ever. 100% close rate.

Her husband John still has his day job — but not for much longer if this conversation has anything to say about it.

I sat down with Jenny Blake (author of Wild Courage) and her husband John to talk through one of the scariest, most exciting decisions a creator couple can make: pulling the spouse out of their stable career to go all-in on the business together. What started as a sponsorship strategy session turned into something a lot more honest than that.

The Setup

Jenny left Google after 18 years — executive level — to launch her book and build a coaching and speaking business. She's 5x her revenue goals in the first year. About half from one-on-one coaching, half from keynote speaking. Brand deals were always supposed to be 10% of the pie. She just never made time for them.

Then she did my 10K challenge, landed her first deal immediately, and had a realization: she's leaving serious money on the table. And she has a husband with a nonprofit job who's watching all of this happen from the sideline.

So the question became: should John quit and run brand partnerships for Jenny?

Here's the thing — this isn't a crazy idea. April helped me grow our Creator Wizard business while I was still in medical devices. Eventually I quit, and yeah, things got weird at first. But it worked. And what I built from that experience eventually became a whole other career.

The playbook exists. The question is whether Jenny and John can execute it without torching their marriage in the process.

The First Fight Is Actually a Good Sign

Before we even got deep into strategy, Jenny brought up something that happened in their kitchen after the kids went to bed.

John had looked at her first sponsorship deal — the $6,000 one — and asked: "Is this even the right brand for you?"

The brand? An AI platform that summarizes books. Jenny's whole business is built around getting people to read her book. Do you see the problem?

John flagged it. Jenny got defensive. They had their first real business fight.

I told them: that's exactly what you want.

John wasn't being obstructionist. He was protecting something Jenny had worked years to build — the trust of her audience. And honestly? He was right to raise it. That's the whole win-win-win framework I talk about in Sponsor Magnet. The deal has to work for you, for the brand, and for your audience. If one of those legs is shaky, the whole thing wobbles.

Now, I did push back on one thing. Jenny called it a "trust battery drainer" like that was a foregone conclusion. But here's what most creators miss: the way you talk about a brand matters as much as the brand itself. You can address the elephant in the room directly. You can say, "I know what you're thinking — why is an author promoting something that summarizes books?" and then answer it. That transparency can actually strengthen trust rather than drain it.

The fight wasn't a bad sign. It was evidence that John already understands what the job is supposed to be.

The Mistake I Made (And You Probably Will Too)

When I quit my job to work with April, the very first thing I did was kick the door down.

I was ready to justify my decision. I wanted to be involved in everything. And April — who had spent years setting up her own mic, her own lights, running her own podcast — looked at me and essentially said: I didn't ask for your help with this. Go find something else to do.

That moment was humbling. And necessary.

If John quits his job tomorrow, his instinct is going to be the same. He's going to want to prove it was worth it. And Jenny — who has built real systems and rhythms over the last two years — is going to feel like someone just walked into her kitchen and started rearranging the cabinets.

So: John, stay in your lane until you're explicitly invited out of it. Jenny, be open to the possibility that John finds value in areas you haven't thought of yet. The brand deals carve-out is the obvious entry point. But there are probably other places he can contribute that aren't on anyone's list right now.

The "Menial Work" Conversation

Jenny brought up something that made me stop her.

She has 2,000 LinkedIn connection requests sitting there unresponded to. Data to cut. Admin piling up. And she said she felt like that work was "beneath John" because he's a man.

I asked John directly: is it beneath you?

"No," he said. "I've told Jenny proactively I'm happy to do those things. I know it's part of the bigger picture."

This is a trap that will swallow your working relationship whole if you let it. You cannot assume your partner shares your feelings about what is or isn't beneath them. Jenny was building resentment over something John hadn't even complained about. She was doing his emotional math for him and getting the wrong answer.

Say the thing. Don't carry it around until it becomes a fight about something else entirely.

The Real Risk Calculation

There's a version of this conversation that sounds like: Jenny is the breadwinner now, all the eggs are in one basket, this is terrifying.

Here's the other version.

John's nonprofit job is one decision away from going to zero. One reorganization. One new executive. One budget cut. When that happens, that entire income stream disappears overnight. That's not stability — that's the illusion of stability.

Jenny's business right now has speaking, coaching, and a brand deal revenue stream that's just getting started. A course is coming. Probably a community eventually. If speaking slows down, coaching can carry it. If coaching slows down, something else will exist by then that doesn't even exist yet.

That's what entrepreneurship actually looks like when you build it right. It's not one fragile thing — it's a portfolio. And a portfolio is genuinely more resilient than a salary, even if it doesn't feel that way.

Our own revenue at Creator Wizard has swung wildly over 15 years. What was 95% YouTube AdSense when I first quit is now a completely different mix. The two biggest revenue streams you have today might be 3% of your revenue in five years. That's not scary — that's the game.

The most important skill you can develop isn't any specific tactic. It's agility.

The One Piece of Marriage Advice Worth Keeping

I'll leave you with this, because it matters more than any sponsorship strategy:

The moment something bothers you — say it. Right then. Don't let it sit. Don't let it compound. Don't leave the room until you've said the thing you were thinking, even if you know it's going to lead to a disagreement.

Working with your spouse means the work never stops. There's no commute home where you decompress and separate. You're in it together, all the time. The only way that doesn't destroy your relationship is if you build the muscle of honesty before resentment has a chance to build.

Jenny and John have that. I could see it in the conversation. They fight well — which means they communicate well. That's the whole game.

At the end of our session, Jenny looked at John and said, "Should we do it?"

He said yes.

She said yes.

I think they're going to be fine.

If you're thinking about adding brand deals to your own business — whether you're doing it solo or with a partner — the Wizard's Guild is where we get into the real work of making that happen. And if you want the full framework for finding, pitching, and closing sponsorships, grab a copy of Sponsor Magnet.

What about you — have you ever thought about bringing a partner into the business? What's the thing that's holding you back?