Tip
Chip Conley talks about blind spots at Airbnb: “I said to Brian, ‘I’ve seen the business plan and the goals for how big we want to be in three years. But what we’re really trying to do is have no regulations and pay no occupancy tax.’ I said, ‘If we’re as big as we’re going to be three years from now, I promise you we’re going to be regulated. I promise you we’re going to be paying occupancy taxes. Let’s take some proactive steps toward building a strategy for how we’re going to be regulated.’ That has consistently been Airbnb’s biggest challenge—regulation in municipal markets all around the world.”
Turns out AI strategy blind spots work the same way.
Your AI startup is growing fast—10x revenue growth, expanding to enterprise, adding features rapidly. The team’s focused on shipping: better models, faster inference, new integrations. Board meetings are about growth metrics and competitive positioning. No one’s talking about the regulatory landscape that’s forming around AI.
You’ve seen this movie before. In 2015, you watched sharing economy companies dismiss regulation concerns: “We’re a platform, not a taxi company.” By 2018, cities worldwide had rewritten the rules. Companies that prepared early (negotiated with regulators, built compliance infrastructure, shaped policy) survived. Companies that fought regulation spent millions on legal battles and lost market access.
Younger executives see current growth and dismiss future constraints. “Regulation is years away. We’ll deal with it when it comes.” They’re hyper-focused on the immediate sprint—the product roadmap, the competitive threats, this quarter’s metrics. You know better. You’ve watched enough regulatory cycles over decades to recognize the pattern: fast growth in gray areas attracts regulatory attention. The bigger you get, the bigger the target.
The companies that anticipate regulation and proactively engage—build relationships with policymakers, invest in compliance infrastructure before it’s required, shape the conversation—gain structural advantages. The companies that ignore it until forced to react spend 10x more and lose strategic optionality.
This judgment—knowing which second-order effects matter before they show up in metrics—comes from watching enough business models hit regulatory walls. You’ve seen GDPR reshape consumer internet. You’ve seen financial services compliance costs kill startups. You know the pattern: what works in a regulatory gray area has an expiration date. That peripheral vision lets you invest in resilience before the crisis.
Chip had the luxury of decades in hospitality watching regulatory battles. You might have decades watching SaaS, marketplaces, fintech hit similar walls. The pattern recognition is what matters—fast growth eventually attracts scrutiny, and proactive beats reactive every time.
Context
Chip Conley was 52 when he joined Airbnb as head of global hospitality and strategy, reporting to Brian Chesky (21 years younger). After 24 years running Joie de Vivre hotels, Chip recognized immediately that Airbnb’s fastest growth strategy (avoiding occupancy taxes and regulations) would become its biggest liability.
He pushed for proactive regulatory strategy early. For experienced executives evaluating AI company strategy, this pattern recognition is critical—you’ve watched enough business models hit regulatory constraints over decades to know which blind spots matter.
That wisdom comes from seeing the full arc repeatedly: growth → scrutiny → regulation → winners and losers based on who prepared.