From Cashmere Sweaters to Billion-Dollar Lessons: What PMs Can Learn from Jason Stoffer's Analysis of Quince

Fireside Product Management

Introduction

One of the great joys of hosting my Fireside PM podcast is the opportunity to reconnect with people I’ve known for years and go deep into the mechanics of business building. Recently, I sat down with Jason Stoffer, partner at Maveron Capital, a venture firm with a laser focus on consumer companies. Jason and I go way back to my Seattle days, so this was both a reunion and an education. Our conversation turned into a masterclass on scaling consumer businesses, the art of finding moats, and the brutal realities of marketplaces.

But beyond the case studies, what stood out were the actionable insights PMs can apply right now. If you’re an early or mid-career product manager in Silicon Valley, there are playbooks here you can borrow—not in theory, but in practice.

Jason summed up his approach to analyzing companies like this: “So many founders can get caught in the moment that sometimes it’s best when we’re looking at a new investment to talk about if things go right, what can happen. What would an S-1 or public filing look like? What would the company look like at a big M&A event? And then you work backwards.” That mindset—begin with the end in mind—is as powerful for a product manager shipping features as it is for a VC evaluating billion-dollar bets.

In this post, I’ll share:

* The key lessons from Jason’s breakdown of Quince and StubHub

* How these lessons apply directly to your PM career

* Tactical moves you can make to future-proof your trajectory

* Reflections on what surprised me most in this conversation

And along the way, I’ll highlight specific frameworks and examples you can put into action this week.

Part 1: Quince and the Power of Supply Chain Innovation

When Jason first explained Quince’s model, I’ll admit I was skeptical. On its face, it sounds like yet another DTC apparel play. Sell cheap cashmere sweaters online? Compete with incumbents like Theory and Away? It didn’t sound differentiated.

Jason disagreed. “Most people know Shein, and Shein was kind of working direct with factories. Quince’s innovation was asking, what do factories in Asia have during certain times of the year? They have excess capacity. Those are the same factories who are making a Theory shirt or an Away bag. Quince went to those factories and said, hey, make product for us, you hold the inventory, we’ll guarantee we’ll sell it.”

That’s not a design tweak—it’s a supply chain disruption. Costco built an empire on this principle. TJX did the same. Walmart before them. If you can structurally rewire how goods get to consumers, you’ve got the foundation for a massive business.

Lesson for PMs: Sometimes the real innovation isn’t visible in the interface. It’s hidden in the plumbing. As PMs, we often obsess over UI polish, onboarding flows, or feature prioritization. But step back and ask: what’s the equivalent of supply chain disruption in your domain? It might be a new data pipeline, a pricing model, or even a workflow that cuts out three layers of manual steps for your users. Those invisible shifts can unlock outsized value.

Jason gave the example of Quince’s $50 cashmere sweater. “Anyone in retail knows that if you’re selling at a 12% gross margin and it’s apparel with returns, you’re making no money on that. What is it? It’s an alternative method of customer acquisition. You hook them with the sweater and sell them everything else.” In other words, they turned a P&L liability into a marketing hack.

Actionable move for PMs: Identify your “$50 sweater.” What’s the feature you can offer that might look unprofitable or inconvenient in isolation, but serves as an on-ramp to deeper engagement? Maybe it’s a generous free tier in SaaS, or an intentionally unscalable white-glove onboarding process. Don’t dismiss those just because they don’t scale on day one.

Part 2: Moats, Marketing, and Hero SKUs

Jason emphasized that great retailers pair supply chain execution with marketing innovation. Costco has rotisserie chickens and $2 hot dogs. Quince has $50 cashmere sweaters. These “hero SKUs” create shareable moments and lasting brand associations.

“You’re pairing supply chain innovation with marketing innovation, and it’s super effective,” Jason explained.

Lesson for PMs: Don’t just think about your feature set—think about your hero feature. What’s the one thing that makes users say, “You have to try this product”? Too often, PM roadmaps are a laundry list of incremental improvements. Instead, design at least one feature that can carry your brand in conversations, tweets, and TikToks. Think about Figma’s multiplayer cursors or Slack’s playful onboarding. These are features that double as marketing.

Part 3: StubHub and the Economics of Trust

After Quince, Jason shifted to a very different case study: StubHub. Here, the lesson wasn’t about supply chain but about moats built on trust, liquidity, and cash flow mechanics.

“Customers will pay for certainty even if they hate you,” Jason said. Think about that. StubHub’s fees are infamous. Buyers grumble, sellers grumble. And yet, if you need a Taylor Swift ticket and want to be sure it’s legit, you go to StubHub. That reliability is the moat.

Lesson for PMs: Trust is an underrated product feature. In consumer software, this might mean uptime and reliability. In enterprise SaaS, it might mean compliance and security certifications. In AI, it could mean interpretability and guardrails. Don’t underestimate how much people will endure friction if they can be sure you’ll deliver.

Jason also pointed out StubHub’s cash flow hack: “StubHub gets money from buyers up front and then pays the sellers later. That’s a beautiful business model. If you create a cash flow cycle where you’re getting the money first and delivering later, you raise a lot less equity and get diluted less.”

This is a reminder that product decisions can have financial implications. As PMs, you may not directly set billing cycles, but you can influence monetization models, free trial design, or even refund policies—all of which affect working capital.

Actionable move for PMs: Partner with finance. Ask them: what product levers could improve cash conversion cycles? Could prepayment discounts, annual billing, or usage-based pricing reduce working capital strain? Thinking beyond the feature spec makes you more valuable to your company—and accelerates your own career.

Part 4: Five Takeaways from StubHub

Jason listed five lessons from StubHub:

* Trust is a moat – Even if users complain, reliability keeps them loyal.

* Liquidity is a moat – Scale compounds, especially in marketplaces.

* Cash flow mechanics matter – Payment terms can determine survival.

* Tooling locks in supply – Seller-facing tools create stickiness.

* Scale itself compounds – Once you’re ahead, momentum carries you.

Part 5: What Surprised Me Most

As I listened back to this conversation, two surprises stood out.

First, the sheer size of value retail. Jason noted that TJX is worth $157 billion. Burlington, $22 billion. Costco, $418 billion. These aren’t sexy tech names, but they are empires. It made me rethink my assumptions about what “boring” industries can teach us.

Second, Jason’s humility about being wrong. “Reddit might be one,” he admitted when I asked about his biggest misses. “I had no idea that LLMs would use their data in a way that would make it incredibly important. I was dead wrong. I said sit on the sidelines.” That candor is refreshing—and a reminder that even seasoned investors get it wrong. The key is to keep learning.

Lesson for PMs: Admit your misses. Write them down. Share them. Don’t hide them. Your credibility grows when you own your blind spots and show how you’ve adjusted.

Closing Thoughts

Talking with Jason felt like being back in business school—but with sharper edges. These aren’t abstract frameworks. They’re battle-tested strategies from companies that scaled to billions. As PMs, our job isn’t just to ship features. It’s to build businesses. That requires thinking about supply chains, trust, cash flow, and marketing moats.

If you found this helpful and want to go deeper, check out Jason’s Substack, Ringing the Bell, where he publishes his case studies. And if you want to level up your own career trajectory, I offer 1:1 executive, career, and product coaching at tomleungcoaching.com.

Shape the Future of PMAnd if you haven’t yet, I’d love your input on my Future of Product Management survey. It only takes about 5 minutes, and by filling it out you’ll get early access to the results plus an invitation to a live readout with a panel of top product leaders. The survey explores how AI, team structures, and skill sets are reshaping the PM role for 2026 and beyond.OK. Let’s ship greatness.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit firesidepm.substack.com