Earlier this month, the entire 500 team was in Puerto Vallarta for our annual winter retreat. Given how dispersed we are, it’s an unforgettable experience to be with everyone from all around the world (more than 20 countries, to be specific).

I witnessed a lot of serendipity over the last few days where people would strike up conversations with a team member they hadn’t yet met in person, which would result in ideas and plans to collaborate post-retreat. Impromptu breakout sessions were formed, which were probably some of the most engaging sessions of the week.

Everyone returned home on a high, invigorated and motivated to do great things. They’re reminded of 500’s mission and why they joined in the first place.

Everything made me reflect on where 500 is at now — 100 team members strong, across more than 20 different countries around the world, over $200M under management, 1300 portfolio companies, lots of GIFs. The journey thus far has certainly been a roller coaster. High highs. Low lows. Severe growing pains. Tons of scars.

Your role as a founder changes dramatically once your team hits 10, 20, 50, 100, and so on. Sometimes you forget how big you’ve grown and continue to act as if you’re still 10 people.

You make mistake after mistake after mistake.

You suffer from a severe case of imposter syndrome.

You constantly wonder WTF you’re doing.

Below are my thoughts on what to expect as your company hits 100 people. YMMV, but one or more of these may cause you to nod your head in agreement — whether or not your company is 100 people strong. (Maybe you’re an early bloomer)