The Cheese #71 🧀 - Kate Winslet, a Vegas Bet, and Steroids (the legal kind)

Locked Up (Literally)

Sunday morning, I got out of the shower, and my lower back felt tight. Within 30 minutes, it had completely locked up, and I could not walk. No event, no lifting something wrong, nothing. All I could think about was 2022, when I had a bulging disc (L4/L5), and how it took me close to a year to get back to normal.

Monday morning, I went to see an orthopedic surgeon. Good thing my car drives itself, because I don't think I could have moved the steering wheel on turns otherwise. Doc said he's 70% confident this is muscular and not spinal. I really hope he's right, because a week or two of recovery beats a year of it all day. I'm writing this late Thursday night, and today was the first day I've felt any sort of improvement, and I'm talking maybe 15-20%. Hoping it's the steroids finally working and I wake up tomorrow with even more improvements. If not, there's a chance this isn't muscular ☹️

The week itself didn't slow down for any of it, though.

Blade Show first. I went for a few hours on Friday, and it was a great time. The team was straight working, cranking out content, and it was great to see. I also picked up 5 exclusive Blade Show knives and handed them to the Whatnot team to use as giveaways on our shows.

Now the agent stuff, because this got out of hand in the best way. I came into the week thinking Leo (the PDP automation) was 99% built. He kind of was. Then on Monday, good ideas started rolling in on other things Leo could do with the same knowledge he uses to build our PDPs. I ended up spending about 80% of every day this week building those new automations. Close to 35 hours. Did not plan on that lol.

Worth it though. The 3 audits I built found about $50,000 of product sitting on our shelves that was not for sale. Listings that were never made but should have been. PDPs hidden on our site, so nobody could buy them. A couple of years of mistakes, and a painful couple of days for the team cleaning it all up. The good news is it's all being cleaned up, and these maintenance audits will run on a cadence so nothing falls through the cracks again.

I eventually built Leo as far as I can take him (without causing context issues), so I started another agent to handle more of the product audits and automations. After talking with Shay and Seele, it was very clear the next agent had to be Kate Winslet.

Kate made her appearance yesterday with her first automation. Every two weeks, she finds active listings on our site with zero inventory, no reorder points, and no open purchase orders, then adds them to a sheet for review so decisions get made quickly. Over 100 products on the first audit. I expect single digits on future runs.

The call with the major network went well, and in a direction we didn't expect. It ended up NOT being solely focused on BattlGames as we had intended. We ended up talking about several other opportunities they already have green-lit that we might be able to participate in as well. And then today we got an email from ANOTHER major network sending us days and times to pick from, because they want to chat about BattlGames too. Exciting times for sure.

Whatnot is off to a fast start. June is currently pacing to do $384k, which would top the $356k record we just set in May. A fast start and momentum are always fun. Also, I made a bet with Cameron. If he does $500k a month on Live Shopping, I'm taking him to Vegas for a couple of days. Not likely for June, but July is already shaping up to be a month where $500k might actually be possible.

Amazon is off to a fast start too, outperforming May by about 27% through the first 11 days. Membership gets its big opportunity today as we relaunch the PACKED promo with brand new landing pages to support it. And Cameron got the product pages duplicated to start building our first eBay Live show, so we are absolutely running a test or two this month. YouTube growth slowed back down; we're sitting at 908k.

Oh, and the only thing on the calendar right now is Disney World with the family in July. The back has until then to get its act together lol.

Let's get into the rest!

How Ralph Lauren Sold a Lifestyle

Lhea's latest. The story of how Ralph Lauren built a billion-dollar empire with no fashion school and no elite connections, just selling a lifestyle people wanted in on. Good operator read.

BAD SALES EMAIL ALERT

The Saturday morning batch process keeps humming. Here's the latest teardown.

Fable 5 Is a Different Animal

Anthropic dropped Claude Fable 5 this week, and the early numbers are wild. Beating GPT-5.5 and Gemini on the benchmarks, and Stripe says it compressed months of engineering into days. Given how much of my week you just read about was spent building agents, you can guess how closely I'm watching this one.

BattlGames Season 3 sponsorships

Quick reminder. We're filming BattlGames Season 3 in Athens, GA, in September, and we still have a few sponsorship spots open. If you want the deck, just reply to this email.

The GTM bets that shouldn't have worked, and did

One grew revenue 50x after half his team quit over the strategy. One brought in 50K signups in a single day with no paid budget. One generated 100M+ views from a stunt that took 50 hours to conceive. One asked every prospect to demo the product themselves instead of demoing it for them.

None of them followed the safe playbook. They treated GTM like an experiment, moved before they had proof, and made bets most founders would never get approved.

HubSpot for Startups documented all 6 stories in the free Bold Bets Playbook. The risks they took, why it was risky, and what it returned.

Read the free Bold Bets Playbook

That’s a Wrap on This Week’s Cheesy Scoop! 🧀

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Team Online Queso