Back in 2010, I was running a startup accelerator called Year One Labs with Raymond Luk, Ian Rae, and Benjamin Yoskovitz. We had a hot take: Most accelerators were just Innovation Theatre: They’d choose founding teams via forms and voting, then spend ninety days trying to pretty them up for a Demo Day where investors might give them money.
At the time, a book called The Lean Startup had just come out, and someone (I think it was Ben) suggested we apply its lessons to an accelerator. So we did things differently:
We ran hackathons to figure out who would be a good fit. A weekend working on a project shows you who can hustle, who’s coachable, and—let’s be frank—who’s a toxic jerk. Better to know early.
We invested a very small amount of money. We had a total of $350K from investors, and we put $50K into each of five founding teams, with $100K to pay for offices, bandwidth, legal, and other costs.
The money came in tranches. $10K to figure out what you were making; $20K to make it; $20K to find investors. That was intentional: If a company couldn’t make it past the first or second hurdle, we’re reinvest it in one that could.
We ran it for a year. This gave the companies enough time to get out of the building, run experiments, and figure out what business they were actually in. This is why we called it Year One Labs. Oh, and at the time, in Montreal, you and a roommate could live on ramen for a year for that much, if you were careful.
We learned a ton. If you’ve heard my interview with Lenny Rachitsky, one of the founders in the accelerator, you know it’s the first time I asked someone (jokingly) if they were being evil enough. And Ben and I used what we learned about measurement and metrics to write Year One Labs.
Plenty has happened since that time. Ben and Marcus Daniels co-founded Highline Beta, which stands up and invests in innovation labs. But whenever Ben and I meet, we inevitably return to our first love: Product Managers.
My first job out of university was as the product manager for client-to-mainframe software at Eicon Technology. Then I managed the dial-up modem banks that answered your AOL CD-ROM for Primary Access (a product called the DNG/IP, which engineering sometimes referred to as the Dung Heap.) When 3Com (the inventor of Ethernet) bought Primary Access, I managed policy-based networking—basically the software that made the Internet handle different types of traffic gracefully at 3Com.
In 2001, I co-founded a web performance startup called Coradiant. I mostly owned the product roadmap. Even when we hired people far smarter than me, I clung to the product manager job for much longer than I should have.
Earlier in the year, Theresa Johnson asked me to speak to the Intro to Product Management course at Stanford. And I sorta roasted product managers.
The thinking went like this:
The job of a for-profit business is to deliver positive returns (to shareholders, the bank, or founders.) If not, that business is fraudulent.
There are other ways to get positive returns, from casinos (high return, high risk) to bonds (low return, low risk.)
The reason people choose to invest in a business instead of a casino or a bond is because they believe it will have a better risk-to-reward ratio than either of those options.
Every employee must ultimately “roll up” to this goal. If you’re in operations, you need to manage costs. If you’re in sales, you need to deliver profitable customers. And if you’re the product manager, you need to steer the product into low-risk, high-revenue seas.
But too many product managers focus on what customers want, instead of what the business needs. They write detailed feature specifications, and order them carefully. They translate user calls and Jira tickets into promises. They forget to make calculated bets.
Most importantly, they almost never view their roadmaps as tools for creating attention and turning it into profitable demand.
Meanwhile, the business needs to grow.
Once upon a time, growth was the domain of the marketing communications (marcom) team. They wrote content, wined and dined industry analysts, fought over press releases, and hired agencies to help them pick Pantone colors. The product couldn’t help growth—after all, a hammer can’t upsell you a new hammer—so marcom did it.
But as every product became—at least in part—digital, growth and the product roadmap became inextricably entwined.
Digital products are cheap to deliver and can be free to try. This led to the Freemium business model, which let users try the product with limitations. Maybe it was a one-week trial. Maybe everything you produced had a watermark. Maybe you couldn’t export your designs. Gone were proof-of-concept trials, replaced by a natural path towards payment.
This gave marcom teams new tactics. Consider Dropbox, which grew by encouraging users to invite new people to the platform. When a user invited a friend, they both got storage. This was unprecedented—and, importantly for this discussion, it was part of the product roadmap.
After the purchase, the product could sell you a higher tier of storage, or more licenses, or advanced features. This was known as Product-Led Growth, and it became central to growing digital-first products without adding sales and marketing teams.
Companies also deployed digital “tricks” to help sales. Some of these were innocuous (a pop-up message that offers you a discount when you’re about to leave a page); others were misleading or even outright fraudulent (pre-checking boxes that should be opt-in, for example.)
The end result? Too many cooks in the roadmap kitchen, each fighting for their customer feature, sales tactic, upsell functionality, or trick. That’s bad for everyone, because when everyone’s responsible, nobody’s accountable.
I put this thinking into a talk for Theresa’s class, and got unequivocally clear feedback, with students calling it “the most applicable [talk] we’ve had so far” and that it “reshaped the way I think about product management.”
So I was pretty excited to share this take on Product Management through a Just Evil Enough lens with Ben. When I was in Toronto earlier this year giving talks to the Toronto Product Management Association and U of T’s Rotman Business School, Ben and I finally got to hang out.
Turns out, he’s been thinking similar things—that product management lost the script, and in many cases became a glorified Jira janitor that could soon be replaced by AI. So we decided to write something about it.
If you’re not already subscribed to Ben’s Focused Chaos, you’re missing out.

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