Adam & the executive team

Adam had an undeniable physical presence that demanded attention. He stood tall, dressed like a rockstar, and carried a reputation for putting people on the spot in front of large audiences. Luckily, I’d heard this before my first interaction with him and made sure I was prepared. As you can imagine, many people dreaded being in meetings with him because of his unpredictability. But I found it entertaining, especially during the weekly Deal Meetings, where he’d casually show up in Adidas flip-flops.

It was never easy to anticipate what Adam wanted to hear. His questions often veered toward the obscure rather than seeking clear, direct answers. But whenever I was asked a question, I made sure to respond in a way I knew would appeal to him and reflect well on my team. One day, he approached my desk and started firing questions. I was ready, confident, and passed his test. Then, he moved on to someone on my team. She handled it brilliantly—until the conversation suddenly shifted, and Adam began asking if her surname was connected to a billion-dollar company and exploring any potential deal opportunities. He was always thinking about deals.

When I joined the company, Adam had a small, tight-knit executive team that operated largely behind the scenes. They were usually seen hovering around him before investor meetings or on stage during All Company meetings, introducing speakers or handing out awards. Most employees had no idea what these executives were responsible for—and frankly, most were too busy to care. The occasional headlines about one of them buying a mansion or something similarly extravagant were more entertaining than relevant.

In 2018, as the company’s valuation climbed rapidly, things started to shift. Power grabs became more visible, and new roles seemed to appear and gain influence overnight. Titles like “Head of Gratitude” or “Director of Culture” started popping up—roles that didn’t always make sense. These middle and upper managers began taking the stage at All Company meetings, talking about the company’s vision and its evolution. Meanwhile, the people actually doing the work were too swamped to even attend those meetings.

The language during these meetings became vague, filled with loose ideas and lofty ambitions that didn’t resonate with most employees on the ground. Alongside this, Adam’s direct team expanded significantly, trying to keep up with the company’s breakneck growth. It was a surreal combination of real hustle, visionary ideas, and corporate theater, all wrapped into one chaotic environment.

Lessons From Adam & the Executive Team

  1. Leadership Style Shapes Culture
    Adam’s bold, unpredictable approach kept employees on edge but also reinforced the company’s focus on ambition and deal-making.
  2. Clear Roles Matter
    Ambiguous or invented roles, like “Head of Gratitude,” diluted focus and created confusion about who was driving real impact.
  3. Leadership Visibility Builds Trust
    A distant executive team leaves employees disconnected. Leaders need to be transparent and actively involved to earn trust.
  4. Power Grabs Disrupt Culture
    Rapid growth and inflated titles fueled competition rather than collaboration, undermining the company’s core values.
  5. Substance Over Show
    Lofty, vague visions from leadership alienated employees doing the real work. Clear, grounded communication is essential for alignment.