Happy Thursday!

I joined John Coyle on The Checkout Pod and we got into the question I get asked probably three times a week: what are the brands actually doing to get to $100M fast? True Classic, Hint, Jolie, Overnight Oats. Here's what separates them. I pulled the 4 biggest things below.

Vendor of the Week

Anrok — sales tax compliance for modern eCommerce brands, now including tax compliance for your ads.

Quick gut check. You're spending on Meta, Google, TikTok, maybe a little CTV. None of that gets taxed, right?

Already wrong in Washington. And actively moving through legislative hearings in Utah, Tennessee, Rhode Island, Pennsylvania, and Colorado.

Digital ad taxes are not a policy debate anymore. They're a fragmenting compliance problem with no standard framework, different revenue thresholds in every state, different exemptions. Most brands have no idea this is happening, and the ones that do are hoping their accountant flags it. The accountant will not flag it in time.

Anrok put together a guide on exactly what's coming, why Colorado's bill is the one to watch, and what your finance team should be doing right now. Here's the part that matters for most ecomm brands: you're not going to have to handle the tax collection yourself, but you will start paying tax on your ad buys. It's the doc worth dropping in a Slack thread with your CFO and media buyer this week.

Anrok handles all of this end-to-end as it rolls out, same way they already handle registration, calculation, reconciliation, filings, and remittance for growing Shopify and WooCommerce brands.

Read the guide on this special link.

The Gap Between a $20M Brand and a $100M Brand

I've been thinking about this a lot on my walks lately. You pass a bodega with a Boar's Head window sticker and realize: that's right time, right place. No one else is getting that real estate again. Some of the brands that made it to $100M were just first to category. But it's not the whole story.

Because there are fast followers in every single category who hit the same inflection points, the same cap table, the same CPMs. And they stall at $20M. The difference isn't luck.

Eight Sleep's mid-funnel strategy is the case study everyone should study. If you Google "Eight Sleep" right now, you'll find comparison videos, unboxings, Reddit threads, YouTube reviews. They built that intentionally, starting in 2017 or 2018. Before they had massive ad spend, they were filling the middle of the funnel everywhere a high-consideration buyer would go to research a $3,000 purchase. Their "Wall of Love" has been growing for seven years. That's a moat.

Listen here: YouTube | Spotify | Apple Podcasts

The Biggest Takeaways

• Brand is not optional past $20M. If your brand is just your logo and color palette, you've got a product business. The brands that break through to $100M have a personality, a story, a reason to exist beyond the specs. Build it early. The cost of skipping it shows up at scale.

• Innovate on top of what's already working. Eight Sleep didn't convince people to buy online (Casper did that). They convinced people to spend $3,000 on a smart mattress once online buying was normalized. Find the market behavior that already exists and build the next layer on top of it.

• Speed is a compounding advantage. Small teams of generalists who use AI to multiply their output will outperform large specialized teams. 128 ads tested vs. 4 is not a small difference. The feedback loop is faster, the learning is better, the cost per insight is lower.

• Win the middle funnel before you need it. Eight Sleep built their review layer, their Reddit presence, their YouTube comparisons before they were at scale. By the time someone searched "Eight Sleep" with buying intent, the content was already there. Most brands ignore the middle funnel entirely until they've already hit the ceiling.

• Nimble beats big. Lemmy is a Kardashian brand. Still a small, fast team. The brands that get to $100M in this era are not building traditional org charts. They're building small groups of really smart generalists with AI as their leverage.

That's all for today

It's Thursday, and it's all downhill from here. Go search your own brand name on Google right now and see what the middle of your funnel actually looks like.

Nik