6 Things To Expect When Your Company Hits 100 People

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)

1. Upholding Values Is HARD.

Values are the foundation of a company. Culture is the manifestation of values IRL — the day to day actions and behavior. Adapt tactical cultural behavior that helps you execute on your values. (and don’t wait — this starts on Day 1) . For example, these are 500’s core values: (also discussed here)

• Be Bold, Be Humble. Forgive mistakes, but not timidity.
• Move Fast, Break Things. Iterate to success. Fast.
• Challenge Yourselves and Others. Hold each other accountable 100% of the time.
• Be Diverse, Be Diversified. Diversity and inclusion is our profit strategy & moral imperative. Embrace it.
• Have Fun, Make Money. It’s our job to make money and GSD, but it’s also our job to have fun.

(It’s also worth noting our love of hashtags. These three encapsulate our values: #500STRONG, #500LOVE, and #HFGSD)

Once your company grows past a certain point, upholding values becomes more and more difficult. This is where companies get into trouble. Thus, it’s absolutely critical to take your company values seriously and practice it everyday.

In Mexico, we shared stories of different team members exemplifying each company value, as well as what values everyone felt we were doing well at and sucking at. (solicited via a company-wide survey prior to the retreat)

Codifying cultural behavior can range from explicit statements, formal policies (ex. declaring a conflict resolution policy), positive reinforcement in the form of rewards/praise, and what I discuss in the next bullet.

2. Rituals Will Make Or Break Your Company.

Many people are allergic to process and structure because it causes traumatic flashbacks of working at BigCo and suffering through bureaucracy for bureaucracy’s sake. (TPS Reports!) They fear that it will stifle creativity and slow them done.

But to the contrary, rituals are absolutely necessary to keeping a company nimble and setting your team up for success. Moreover, they will help you actually practice your values day-to-day and make them more tangible.

Rituals are applicable to anything and everything, be it team communication, meetings, quarterly OKRs, sales, customer engagement, data, team bonding events, etc. Investing in rituals, as well as solid infrastructure across the company, will do wonders for accountability and performance.

Within the 500 team, 15Five and weekly 1:1s are channels for managers and their direct reports to keep each other accountable and share feedback. Teams regularly communicate what they’re working on via emailing weekly meeting minutes or monthly summaries. Every accelerator batch kicks off with a welcome night where we invite 500 alumni and community, and it is always a fun evening. And for the last few years, we’ve done a pretty good job committing to bi-annual company retreats in January and June.

Professional athletes don’t play it by ear when it comes to practice and conditioning. They have insanely disciplined regimens and rituals which enable them to perform when it counts. The same applies to companies.

3. Let It Go.

As a founder, your role undergoes a dramatic transformation as the company grows beyond the founders. You’re no longer hands-on with things you were before. Letting go is oftentimes the hardest thing for founders to do. But it’s critical for your team to be empowered and feel ownership over their role in order to expect high performance from them.

This may mean removing yourself entirely from discussions or even offering your 2 cents unless explicitly asked. Become ruthless about delegating and trusting your team to make smart decisions. In fact, do it at the expense of your own recognition. This is often one of the toughest things for founders to do. After all, it’s much more fun to build product than to review your 2016 budget forecast, right?

Micromanaging or being unable to delegate means you’re too busy meddling in things your team is more than capable of handling, and you risk driving people away because they feel demoralized about never owning their work.

Don’t be that kind of leader.

Doing is how your team learns. The new approach and perspective of the team is why you hired them in the first place. Let them do their job. Only interject if you see something catastrophic with the idea.

4. High School Never Ends.

High school drama ends with high school, right?

Wrong.

As your company grows, cliques naturally form — whether it’s by function, office, age, hobbies, you name it. Birds of a feather flock together, and as long as your company’s hiring humans vs. bots to do work, it will be par for the course. Curiously, when humans interact, sometimes they don’t get along.

A big chunk of my time is spent on supporting our team through RITUALS like weekly 1:1s, responding to 15Five reports, answering questions, offering encouragement, and helping to resolve conflict. Riffing off of #3, you may be accustomed to fixing bugs in code. Now your time may be spent fixing ‘bugs’ within your team. Your role becomes a lot more about people — hiring, firing, and firing them UP and setting them up for success. But rather than perceiving this as a hassle, take it seriously. Your team matters.

Also, preventative medicine is more effective than reactive medicine. If you’ve waited until something manifests into a real problem to address it, you waited too long. Invest heavily in solutions (rituals!) that will prevent problems before they happen. It will make your life easier, and your team will be happier as a result.

5. Approach Diversity and Inclusion From All Angles.

We think about diversity and inclusion as it relates to race, ethnicity, gender, age, religion, etc. However, it’s also important to be inclusive to different working styles and find ways to bring out the best in everyone.

For example, introverts and extroverts. Post-retreat, I heard feedback from several people that 500 has quite the extroverted culture, and the retreat format presented challenges for introverts who weren’t comfortable standing up and talking in front of 100+ people. It was an unfortunate realization that a lot of how we operate day-to-day is “loudest voice wins” (ex. how meetings are run, how we evaluate investments, etc) which is hugely demotivating for the many talented people who aren’t vocal.

As much as you can encourage people to speak up, create rituals that also cater to the introverts. It could be in the form of written communication (ex. written surveys, email, Slack), intimate settings for feedback (1:1 or smaller groups), meeting agendas where each person is given the opportunity to share ideas or lead a topic, etc. Otherwise, you risk losing amazing talent.

6. Don’t Worry So Much About “Not Supposed To”.

A line from Chocolat, one of my all-time favorite movies. Naturally once your company is big, you may start to think “I can’t do that anymore, we’re no longer a small startup.” It’s not unlike how people feel pressure to act a certain way once they become a parent — almost as if they can’t be their true selves.

While you will need to change certain things about how you operate as the team grows (for example, if transparency is a core value, you may execute on that differently with a team of 10 vs a team of 100), it’s also an opportunity to break the mold.

Stay true to your values and all else will follow. Don’t do things just because it worked well for Google or Facebook. Do what’s right for your company.

Special thanks to Susan Su, Dave McClure, Bedy Yang, Tawheed Kader, Brett Northart, and Ken Lin for their feedback on this post.