Failing to scale is not about lack of will. I haven’t heard of someone who got layered at a startup and wasn’t trying as hard as they could to keep up with the job.

Experience definitely helps, but even experienced leaders have to accept that their past experiences are not perfectly translatable to a new startup.

Perhaps a better way to think about experience is not as how many times you’ve done a job before, but instead how many times you had to change yourself in order to be successful.

hiring an exec who spent twelve years at Google will almost certainly be a disaster for an early stage company.

If ability to change is what it takes to scale, a more interesting question, then, is why changing is hard.

The moment you stop paying close attention to each individual action, you come back to auto-pilot mode.

There’s a better way to change your actions: change the belief system that generates them instead.

Reinventing your core beliefs is the silver bullet of scaling.

There’s a certain grief involved in reinventing your core beliefs: a part of you has to cease existing for the new to come in.

once the death is accepted and the grief period is over, there’s now fertile ground to nurture new core beliefs. A new version of you. Ready to scale.

if you ask someone how to become a better leader, they will tell you to surround yourself with good leaders and learn from them.

It is frustrating, but learning from good leaders is the safest path we know to become a better one. A big part of the reason is because the hardest parts of a leader’s job can’t be learned by reading a book. You have to feel it in order to develop a sense of what great looks like.

While heroes are absolutes, role models are domain-specific. It’s important to learn what to learn from whom.

it’s important to be authentic too, and lead in a way that is compatible with who you are.

people want to know who you really are. What are your quirks, your passions, your style, and what makes you different? Don’t hide these away; put them at the forefront.

I figured out that writing is a more authentic communication method for who I am. This led me to start writing weekly emails and essays, which became an important part of how I lead.

the easiest, and best way to be authentic is to be vulnerable. Since every person is going through a unique challenge in life, when you share any details about what you’re struggling with, it is remarkably authentic.

People can read through the lines much faster than you think. Sharing where you are on your journey is just stating the obvious, but with bonus points for authenticity and trust. Do it.

Dismissing your intuition is ignoring valuable data.

when you’re making a hard decision with no clear answer, but it still feels right, don’t dismiss it just because you can’t explain it.

Reinventing your core beliefs, picking the right role models, being authentic, and listening to your feelings.

the biggest leap of faith of all is having faith in yourself. Things will go wrong, and you’ll feel like a failure many times. But don’t assume that you can’t scale just because you haven’t done the job before. The truth about successful startups is that no one really has.

The struggles are what shape us. So regardless of how hard it is, embrace the journey of scaling. Cherish every moment of accomplishing things you didn’t think you would. Remember what it feels like. These are the moments you will never forget.