[INTERNAL MEMO]

Nothing Fails Like Success

The people we honor today didn't have the luxury of comfort. They moved with urgency because the MISSION demanded it.

That's the standard I want us to hold ourselves to, not just today, but every week.

Here's what's been on my mind...

I remember back in 2019 we were sitting in a room reviewing the numbers in our quarterly meeting at Gym Launch. Everything was up - revenue, retention, team size, the scoreboard looked awesome by all accounts. "All greens baby"

By every metric, we were fucking winning.

And in the next moment I remember looking around the conference room and realizing something frightening - nobody looked hungry.

Listen, I’m not asking for everyone to look STRESSED or PANICKED (that doesn’t help) but everyone just looked soo comfortable.

What I realized is that everyone in that room felt a false sense of relief, like suddenly we had ‘made it’. I remember the feeling of unease that sat with me for those two days, as I wasn’t yet the leader who could call it out directly.

Here's the thing nobody tells you about success: it's not a reward. It's a TRAP. "Nothing fails like success"

Every company follows the same S-curve. You start scrappy, you attack with everything you have, you grow fast. Then you hit the plateau, what most people call "making it."

And that's exactly where the decline begins insidiously. The irony is that it does not start with some terribly bad decision, crisis, or massive mistake - it starts with COMFORT. With the slowing down that happens when people stop feeling the pressure of the gap between where they are and where they need to go.

460 of the original Fortune 500 companies are no longer on the list.

And if you study them - they certainly didn't all get outcompeted by someone smarter. Most of them got comfortable first, and comfortable second, and by the time the threat was visible it was already too late to respond to it.

The principle that keeps me up at night is this: getting to the next level requires no less effort than getting to this one. The market doesn't give you a discount for past performance. It doesn't care what you built last year. The standard doesn't drop just because you've already hit it once.

(Please think for a moment on how that applies to us, IMO us doing a $100M launch last year is truly irrelevant, you should all feel the same))

So I started asking my team a different question after that quarterly.

Not "how do we grow?" but "if I wanted to destroy this business, what would I do?"

  • Let people focus on doing their jobs instead of staying connected to the mission.

  • Stop setting deadlines that actually challenge anyone.

  • Measure hours instead of outcomes.

  • Convince ourselves our market position is safe because it was safe last quarter.

  • Slow down the decision-making.

  • Let good enough become the standard because things are going well enough that no one's forcing the issue.

READ THAT LIST. I want you all to really ask yourselves which of these you are currently doing. Nobody is immune to this, it takes self awareness to continuously win and shed these behaviors that creep up.

Winning once is easy, winning time and time again - year over year - takes a champion TEAM.

Now - the fix for this is not packing and letting anxiety keep you up at night.

It's a healthy urgency.

Urgency isn't a feeling, it's a DECISION you make.

Urgency when things are hard is what pretty much everyone does.

Urgency when things are good is what separates the companies that stay great from the ones that become case studies in what went wrong.

As leaders, we are either thermostats or thermometers. A thermometer reads the room. A thermostat sets it. Your team will only ever rise to the temperature you set, not the temperature you used to set, not the one you set two years ago when we were fighting to prove ourselves, the one you're setting right now.

If you're not actively resetting it upward, the room cools. And your team cools with it.

So this week I want you sitting with three questions.

  1. In what way is your current success a threat to your future success?

  2. Where on your team has comfort quietly replaced urgency and are you willing to reverse it?

  3. What would it look like to reset the thermostat starting Monday, not when things get hard, but right now while things are GOOD?

– Leila

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