The real danger for leaders comes during great success, when it is easy to become detached from reality. Avoiding the bubble created by executive perks requires a conscious effort to stay grounded, as this is when judgment is most at risk.
Technically-minded founders often believe superior technology is the ultimate measure of success. The critical metamorphosis is realizing the market only rewards a great business model, measured by revenue and margins, not technical elegance. Appreciating go-to-market is essential.
Founders remain long after hired executives depart, inheriting the outcomes of past choices. This long-term ownership is a powerful justification for founders to stay deeply involved in key decisions, trusting their unique context over an expert's resume.
AI services crawl web content but present answers directly, breaking the traditional model where creators earn revenue from traffic. Without compensation, the incentive to produce quality content diminishes, putting the web's business model at risk.
The tech industry creates first-generation wealth at an unprecedented rate, yet there's a lack of services to help these individuals navigate its complexities. Unlike inherited wealth, they lack pre-built support structures, creating a significant business opportunity to serve this group.
Effective long-term leadership isn't static; it's an 'accordion' that flexes between deep involvement and granting autonomy. This adaptive approach is key for different company seasons, knowing when to lean into details and when to empower the team to make 'foot fault' mistakes and learn.
Michelle Zatlin finds her 15-year tenure doesn't feel 'hard' because she loves her job, feels lucky, and believes Cloudflare is just getting started. This long-term passion for the 'awesome adventure' overrides the daily difficulties and the allure of other opportunities.
When a key leader left Cloudflare for a CEO job, Michelle Zatlin reframed the frustration. She views it as a positive signal that other public companies recruit from their team for top jobs. This perspective validates the company's talent caliber and helps manage the pain of recruiting again.