Getting sued, running dry, and going obsolete are all normal. Durability is what you build around them.
Jason's lawsuit stories and an asset-protection checklist, a live coaching session with a $20k-in-debt Amazon seller, and how Carter and Jason each future-proof for the next decade.
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Will you get sued?
Carter: never personally sued — it comes down to knowing where the line is. Jason: get big enough and you'll most likely get sued; the bigger and more public you are, the more people think they can win.
Jason, on ADA scans and SMS trolls. share
What a $300 mailer can cost.
Protect what you build.
At scale, hire a legal team to structure this properly. Until then, the basics:
you always want to have it and not need it
William: electrolytes, Amazon and Shopify.
Ad spend last year. Didn't break even. share
Business credit-card balance carrying the spend.
"Passive" income the brand still throws off.
Amazon keeps selling even while the ad spend doesn't work. "I'm totally in the red, not in a good way."
Jason
What does the data say?
At $10k you're just buying data. Has he checked SKU take rates, flavors? Go narrower: of 20 sales, did 3 come from one ad? Lock in on one image, one channel, no new debt.
Carter
Two levers, and you're short one
Money and time-and-effort are the only two levers in business. His own brand went -$500k over 12 months before break-even — with capital behind it. William doesn't have that lever, so the other one has to work harder.
Broke-brand triage
- Read the data: SKU, flavor, bundle, subscription, which ad drove sales.
- One channel, one ad format, narrow until profitable.
- Zach Stuck: 1 image × 50 headlines → 5 → iterate.
- Amazon first if that's where sales already are.
- No new debt.
John Haddon: Amazon is financially incentivized to rank whichever listing converts best — 12% vs. a competitor's 11%. Hyper-focus on the one channel where sales already happen before adding more.
you really only have two levers you can pull in business like you can pull the money lever you can pull the time and effort lever
How Carter future-proofs
Marketing pivots every year — TV didn't kill advertising, it moved it. Future-proofing is mostly knowing what other people are doing successfully right now.
- Build systems.
- Stay in the conversation.
- Raise LTV: recurring, data, back-end.
- Cut the middleman.
- Reinvent niche software with AI; retrain teams on AI.
Carter
Systems and LTV:CAC
Build systems, stay in the conversation, and watch LTV:CAC. If acquisition cost keeps rising, raise lifetime value instead — recurring revenue, data monetization, a bigger back end off every sale.
Jason
Cut the middleman
Every layer of brokering you remove is alpha. All software gets reinvented for AI agents over the next 5-10 years, and every employee needs retraining — his AI-using staff are already far more productive than the rest.
if you can pull out the middleman you're going to create alpha
Money moves in waves.
Ad platforms get pricier, offer owners get savvier with funnels and payouts, and the cycle turns again. The last huge lead-gen boom was ACA a couple of years ago — booms tend to trail a government-subsidized program (ACA, solar tax credits, Medicare), so they track who's in office.
The operators in Carter's circles keep going through every cycle. The skill set transfers across verticals. share
Someone else will figure it out first. Find that person, and if they're generous enough to share, you'll always be good.
Every shelf looks like the summit.
Whatever you're standing on right now, a lawsuit, a big campaign, a crash, is a shelf with a limited view. The fix isn't willpower. It's finding people further up who can see the shelves you can't yet.
“the most important machine to feed is yourself” Jason. share
Work harder on yourselves than you do in your job or your work.