The rocketship

The odds of riding a successful unicorn are slim—about 0.00006%. It takes a combination of relentless hard work, a good dose of luck, and immense personal sacrifice. Not everyone is willing or able to endure the turbulence, let alone thrive in it.

I didn’t experience WeWork’s earliest years firsthand, but I made it a point to seek out stories from those who did. They described a tight-knit group of people who pushed themselves to extraordinary limits, achieving ambitious goals in what was often described as a "work-hard, play-hard" culture. It burned people out, yes, but it also got results and created career-defining opportunities.

When I joined WeWork in 2017, the long hours and drive to succeed were still woven into the company’s DNA. However, the arrival of newcomers from prominent firms—many from the Big 4—introduced office politics and egos that quickly became part of the dynamic. Even so, the energy to achieve big things remained a defining characteristic of most of the workforce.

One thing that stood out to me, coming from large corporate transformations, was the sheer startup hustle. It was remarkable to see how the company, despite its size and complexity, still operated on spreadsheets, Airtables, and Monday.com boards. WeWork had scaled to a global organization while holding on to these scrappy, resourceful tools.

It was also the first time I was exposed to early-stage tactics in such a raw form. I remember a conversation with a top 50 joiner who described visiting 20 cafes near a new location, striking up conversations with people working on laptops, and handing out signup discounts. It was grassroots, hands-on, and deeply real. I appreciated that hustle and had a genuine respect for the people who embodied it.

The contrast between the different cohorts of employees was striking. It’s like the expanding rings of a tree trunk. The early employees—the inner rings—were incredibly talented, resilient, and self-driven. They had independently built and scaled new products and business units, working collaboratively and valuing diverse perspectives.

Then there were the newer employees—the outer rings—who brought technical expertise, said all the right things, and quickly climbed into management roles, despite making minimal impact on the business. This dynamic stalled progress, caused friction, and led to a wave of attrition. By the time I joined, many of the early employees were burnt out and ready to pass on their responsibilities.

This experience underscored the critical role business managers and HR play in integrating different cohorts in a growing workforce. New employees need to understand and respect the achievements and culture of early employees, while early employees need support in adapting to professional management practices. Without intentional effort to bridge these gaps, the tension between groups can lead to hostility and wasted potential—time that could be better spent driving growth.

Takeaways

  1. Early-Stage Tactics Deliver Results
    Grassroots approaches, like directly engaging with potential customers, create authentic connections and fuel growth.
  2. Early Employees Set the Tone
    Inner-circle employees embody the company’s original culture, driving resilience and collaboration in the early years.
  3. Cultural Shifts Create Tension
    The arrival of corporate hires can disrupt startup dynamics, introducing politics and egos if not carefully managed.
  4. HR and Leadership Must Bridge Cohorts
    Integrating early and new employees is essential to avoid friction and ensure a unified, productive workforce.
  5. Startup Hustle Builds Respect
    Scrappy, hands-on efforts, even at scale, foster a sense of authenticity and earn respect from those involved.