E16: The Pricing Playbook
In this episode of The SaaS Operators, we dive into Prime Day data, shifting consumer behavior, and what it signals about the broader slowdown in e-commerce. Jeremiah breaks down why Prime Day underperformed and why Amazon is no longer the discovery engine it once was. We explore how DTC brands are getting squeezed and why the winners are pulling further ahead. Rishabh raises tough questions around pricing strategy, flat-rate ceilings, and whether today’s growth is just pulling forward demand. We talk through SaaS retention, CAC misalignment, and why median order value might be the better metric. Zach shares how one DTC brand rebuilt their business from the ground up post-tariffs and the pricing insights that unlocked their next wave of growth. We also go deep on nostalgia-driven investing, broken brand stories like Harley-Davidson and Kodak, and the case for a PE fund that buys and revives brands built on childhood memories. The episode closes with a debate on flat pricing, competition, NRR tradeoffs, and whether private equity will start using AI agents to turn around bloated service-heavy SaaS companies.
Someone claimed it was Shopify’s biggest sales day ever. It wasn’t. Jeremiah checked the numbers, it didn’t even beat July 4th weekend. Even with a four-day window instead of two, sales were soft.
Day one? Up 12% YoY.
Day two? Up 6%.
Combined? Just 18%.
Considering how much e-com is supposed to grow each year, that’s not impressive. Especially when you remember inflation.
Amazon’s Not Fun, It’s a Tool Now
Has Amazon matured into a utility? You don’t browse, you search. You solve a problem, you check out. That’s it. There’s no discovery. No dopamine.
Most of us didn’t even log in.
Rishabh ignored the sales entirely while shopping for his kid’s birthday.
I only knew Prime Day was happening because I work in this space.
That says a lot.
Brands Are Winning the Emotional Game
Amazon gave us abundance. Now brands are winning by helping customers feel something. Whether that’s trust, simplicity, or nostalgia, they’re building moats with meaning.
Like Stamped. One product. Clear pricing. No mess. You know what it does, you know what it costs, and you don’t have to talk to five sales reps to get a quote. That’s powerful.
Flat Pricing Sounds Great, Until It Isn’t
Flat pricing works until your flat price becomes a ceiling. A customer paying $1,000/month now sees that as your max value. When a competitor shows up at $300, your customer asks you to match.
And if you add a second product? It’s not an upsell. It’s a discount tool to save the deal.
That’s why Jeremiah’s model works:
- Feature gating
- Clear upgrade paths
- No automatic price hikes
- Value scales with usage
It’s technically flat, but it’s flexible. And it avoids the “no NRR” trap.
Great Operators Survive Tight Markets
The mediocre are getting squeezed. The good ones are rebuilding. Zach told a story about a brand that restructured everything, supply chain, offers, pricing, and came out stronger. The trick? Stop optimizing for AOV. Start optimizing for median order value. That’s what aligned CAC with profit.
Smart move. That’s what this era demands.
PE Should Be Jumping on This
There’s a big opportunity here:
Buy $20–80M SaaS businesses bloated with services.
Replace workflows with AI agents.
Service the debt with improved cashflow.
Rebuild. Scale. Exit.
It’s LBO + AI. Obvious play. No one’s really doing it yet.
Nostalgia Is a Cheat Code
Harley-Davidson. Levi’s. Kodak. These brands should be thriving. They just stopped standing for anything. Meanwhile, Crocs figured it out. They leaned into the weird and built a movement.
Zach and I want to start a nostalgia PE firm. Buy old brands. Rebuild the emotional connection. Make them cool again. First buy: Heelys.
The market’s crowded. But if you create something that feels like home, you’ll always have customers.
The Takeaway
Prime Day is a proxy. It’s not just about Amazon. It’s a reminder that the whole market is maturing. Growth is slowing. Competition is tightening. And the old tricks don’t work anymore.
To survive, you need a point of view.
To win, you need to make people feel something.
