Hi all –

This is the 100th edition of my newsletter, The One Thing. That means I’ve spent 100 weeks thinking about and sharing the most important lessons I’ve learned building Drift. It also means you’ve stuck with me for 100 weeks. And for that I am eternally grateful. Because I’m learning just as much from all of you.

So, to say thanks (and catch anyone up who hasn’t been here for all 100 editions), I wanted to share some of the most important lessons I’ve learned over the past couple of years.

What lessons resonate with you most? How can I continue to make this newsletter valuable for you over the next 100 editions? Text me at +1-212-380-1036 to let me know.

– DC

P.S. Share my newsletter out with this Click to Tweet and I’ll pick three people to win limited edition Drift swag.

#21: Building a Learning Machine 

Of all the great lessons I’ve learned from Charlie Munger, this one is my favorite (which is why I made it one of our Leadership Principles at Drift):

“I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines. They go to bed every night a little wiser than they were when they got up and boy does that help, particularly when you have a long run ahead of you.”

At Drift we aren’t building a product, we are building a learning machine. A learning machine that can learn from our customers, adapt to a changing market, and deliver solutions that help our customers enter a new era where businesses can easily buy from other businesses the way we do in our personal lives.

So each day, remember to go to bed a little bit wiser than you were when you got up, and that way you too can become a learning machine. If we all do that, then over the long-run we will have created a remarkable team and an enduring company.

Read the full edition here.

#30: Cultural Fit

The problem with hiring for cultural fit is that people tend to just hire people who look and sound just like them. But the key to hiring the right people is recognizing the behaviors you celebrate, and those you don’t tolerate.

At Drift, we want to be the new face of corporate America. We want to be made up of people who look, sound, and think differently. Because that is how great things are created – and how we will build an enduring company.

But we also want people who embody the things we celebrate – like bias for action, an obsession with our customers and the desire to be a curious learning machine.

So the next time you’re interviewing a candidate, ask yourself: “Does this person represent what we celebrate?”

Read the full edition here.

#7: Circle of Competence

“Know your circle of competence, and stick within it. The size of that circle is not very important; knowing its boundaries, however, is vital.” – Warren Buffett

Warren Buffett and Charlie Munger developed the Circle of Competence as a mental model to limit where to make financial investments (based on understanding and / or experience), but I’ve found the model to be useful in all areas of life. The idea is to understand where you’re naturally strong and to stay within that area.

Your circle of competence is the subject area that matches your skills or expertise. And understanding your own will help you concentrate on areas you have the greatest familiarity with while also aligning a subjective assessment of your own competence with your actual competence.

And it’s not the size of the circle that matters, but how well you stick within it.

Sticking strictly to their own circles is what makes Buffett and Munger among the most successful investors in history. They stick to what they know.

And remaining within one’s circle has a number of benefits – an unfair information advantage, a narrower pool of available options, and the reduction of poor decision making. Pretty powerful stuff.

Read the full edition here.

#5: Achieving the Impossible

 As teams grow, it’s inevitable to feel like it’s harder to get things done. This is normal.

There are many theories for why this is – from the telephone game example we all played as kids to theories like Dunbar’s Number, which claims that humans are only capable of supporting a small number of stable social relationships.

But whatever the reason may be, it’s the solution that matters. Which is why I want to focus on how to prevent this feeling from taking over in the first place.

So as your own company and teams grow, I encourage you to optimize for the following:

  1. Stay focused and move quickly.
  2. Question everything.
  3. Assume best intent.

These three things alone won’t completely solve every issue as you scale, but they will help you continue to operate as if you’re still that small, tight-knit organization.

Read the full edition here.

#52: The Tough Conversations

“What have you learned from the tough conversations you’ve undoubtedly had to have over the years?”

That’s a question I received recently and I thought it was particularly relevant in this current climate. Because not only are we all having tough conversations right now – with each other, with our customers, family members, etc., but those conversations are even harder when you can’t have them in person.

So here are the three things that I’ve learned to make these conversations easier and as constructive as possible:

  • Assume best intent.
  • Sleep on it. Don’t just react.
  • Do the right thing for the business, not for yourself.

Read the full edition here.

You can catch up with every edition of The One Thing right here.

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