When Founders Grow Up Too Fast
And a few ideas for more ethical founders
In January last year, I had the pleasure of listening to a talk from Jeremy Weinstein at NYU Abu Dhabi. He argued the startup-building mantra is flawed. It usually goes like this: find a problem, scale a solution as fast as possible, and you win (who cares how many things you break along the way).
🔎 SIGNAL
That’s a one-sided, single-minded approach to operating a venture. A single focus on the problem often overlooks the bigger picture. Weinstein gave the example of a founder who spotted a problem: nobody likes to pay parking tickets.
He built a very efficient solution: a chatbot that disputes your parking ticket fine, and often wins (more for the attrition and cost of considering your case than for the abilities of the chatbot, by the way). However, Jeremy argued, parking tickets exist for a reason. Laws exist to maintain an orderly society.
Most founders of VC-backed companies feel the pressure to “blitzscale” while second-guessing their moves. Meanwhile, the SEC, FTC, and EU regulators are scrambling behind the scenes to catch up with an ecosystem designed to reward blitzscaling and market dominance.
In this climate, books like Careless People (Sarah Wynn-Williams’ memoir from inside Facebook’s leadership circles) should be making waves and prompting regulatory scrutiny. Strangely, they’re not (yet, hopefully).
The book isn’t perfect. But it’s a necessary mirror: for heads of state, ministers, startup operators, tech platform users, and yes, for people like me who have built tech companies while juggling ethical tradeoffs with personal costs. The question is no longer if we need better safeguards—it’s how we design incentives that let founders choose the right path, without martyrdom.
🎥 STORY | Careless People—a memoir from the Ex-Director of Public Policy
Sarah Wynn-Williams wasn’t your average Facebook senior employee. She joined early, stayed long, and climbed high enough to see the machine from the inside. In Careless People, she writes about decisions made as much as more critical ones that were dodged, distorted, and denied.
She tells of leaders shaped more by proximity to power than preparedness. Of a culture that rewarded growth and blind founder loyalty while externalities—harms to democracy, mental health, civil discourse—were relegated to PR containment strategies. It’s not a surprising story. But it’s a rare one, told by someone from within.
That said, the memoir left me unsettled. Not just because of what she describes (a familiar stew of arrogance, youth, and hypergrowth), but how she describes it.
There are no citations, no sourcing—just memory. Anecdotes float untethered from corroboration. She paints herself, often, as the lone adult in the room. According to her account, she was underpaid and overworked, yet ethically aware. Maybe. But anyone who joins Facebook that early and that senior isn’t exactly working for minimum wage.
Still, I found myself nodding more than wincing (and my full review of the book will soon appear on Honest AI). Because her central tension is real: What happens when your job is to manifest the digital nation state power of an emerging company, while your employer’s superpower is pretending the risks aren’t there?
It’s not a hit piece. It’s more intimate than that. She doesn’t shout about villains. She mourns a culture that forgot how to think long-term.
🧭 THE HUMAN OVERRIDE
Wynn-Williams’ book stirred something uncomfortable in me. Because I’ve been there. Not inside Facebook’s war rooms, but inside tradeoffs. As a founder, there’s no shortage of choices. But there’s a severe shortage of time, clarity, and (let’s be honest) economic cushion to always choose the principled path.
There’s a pattern in Careless People that struck a nerve: even the smartest people avoid hard ethical questions when incentives reward speed, opacity, and ego. The antidote isn’t more values posters in the break room. It’s design. Ethics needs to be structural—baked into process, not bolted on as PR.
Here are a few ideas to make that real:
Incentives for ethics in founding teams
1. Delay as a Feature
Facebook’s mantra was “move fast and break things.” Sounds cool—until what you break is democracy. Why not take six months to evaluate entry into new markets? Boring? Maybe. But boring decisions are often better ones. Institutionalizing waiting periods in high-impact product decisions creates space for judgment. A two-week delay before a major launch. A 24-hour cooling-off period before changing core algorithms. Not everything needs to ship by Friday.
2. Laws That Regulate Incentives
Corporate values are aspirational. Legal accountability changes behavior. Theranos execs only got serious about data accuracy when prison time was on the table. Make companies liable for the harms caused by their products, especially at scale. When risk can’t be offloaded to users or buried in legalese, decisions get sharper, fast.
3. Coaching for Judgment, Not Just Pitches
VCs spend zero teaching founders how to make ethical decisions under pressure. Accelerators should run founders through simulated moral dilemmas, just like they run market validation sprints. What happens when your recommender system amplifies hate? When your AI helps someone cheat on a medical exam? Judgment isn’t instinctive. It’s trained.
4. Tradeoff Logs
A simple habit: log the ethical tradeoffs. When you choose growth over safety, document the why. Treat ethics like code: if it’s not versioned, it didn’t happen. This also builds solid institutional memory.
5. Stop the CEO Worship
When we treat Zuckerberg (and Musk, Amodei, Altman, …) like oracles instead of humans, we give everyone else permission to skip the hard thinking. These aren’t philosopher-kings. They’re guys who got lucky with timing, capital, and compounding effects. If we stopped deifying them, maybe more founders would feel free to think critically, not perform invincibility.
The underlying idea here is simple but radical: don’t just expect ethics—engineer for it. Make it easier for good people to make good decisions. Because if we keep relying on founder heroism, we’re going to keep getting ethical trainwrecks wrapped in TED Talks.
🔥 SPARK: What If We Paid Founders to Pause?
Here’s a provocation: What if governments created ethical sabbaticals for founders at scale-heavy startups?
Imagine: You hit 100M users. You get a state-sponsored 3-month sabbatical, paid. During that time, you meet with ethicists, civil society, regulators. No launches. No press. Just structured reflection.
Crazy? Maybe. But so is the alternative: a generation of leaders sprinting through the fog, celebrated for not stopping.
Wynn-Williams’ book isn’t flawless. But its flaws say something too. We don’t yet know how to talk about ethics in tech without making it either a confession or a TED Talk. We need something in between: sober, structured, and public.
Because in the end, what we reward is what we scale.