Jack’s parting letter to Sarah Friar

Amazing parting email Jack sent to Sarah.


Long SQ


Someone in the Becoming an Investing Master asked recently “What financial indicators do you track for the companies you invest in?”

My answer can be summed up as:

I don’t. I don’t invest in companies, I invest in people.

And Jack’s note to Sarah is perfectly indicative of the kind of person I like to invest in. Which makes me even more confident of my choice to own SQ. But, I am also now interested in looking at NextDoor, because for someone like Sarah to have had such an impact on someone like Jack to have moved him to write such a parting letter indicates just how highly he thinks of her. Which means that any company she’s leading is worthy of investigating.

And just to be clear:

Note 1: while I don’t track numbers over the long-term, it doesn’t at all mean I don’t look at them, especially in the beginning, and periodically over time.

Note 2: just because I now understand a little bit more about both Jack and Sarah, it does not mean that any company they may run is necessarily worthy of investing in. I don’t own TWTR, for example, and NextDoor may not be worthy of running, despite each having great leaders. But the fact that they each have great leadership will make me dig in even more!

Paul - who now wants to buy even more SQ…

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Paul, I couldn’t find Jack’s letter to Sarah. Since it’s publicly posted, would you mind putting a copy on the board?

Nextdoor is not public (net yet anyway). I’m a subscriber. I posted briefly about my perspective of it as a user on a different thread. It’s pretty much an electronic neighborhood bulletin board/blog. Maybe I have no imagination, but I’m hard pressed to see much potential in it, especially with respect to monetization. I don’t who set it up in my neck of the woods, how manages and maintains it or who pays for it (I don’t, subscription is free, I don’t even recall how I became aware of it). In a way it’s like one of those local weekly papers that gets dropped on your driveway whether you want it or not, but so far as I can tell, there’s no paid advertising. I get daily emails that lists the post subjects, if nothing interests me (which is most of the time) I delete the email and never look at the website.



Link to letter from Jack - Sarah posted a series of 4 screenshots on twitter

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Apologize for not reading this initial post… I copied the transcript from twitter to make up for it!


Thank you for everything you’ve done for me, Square, and the world. You’re an amazingly solid leader and partner, and I’ve learned so much from you and what you do, and what you choose not to do.

No one has ever written me a letter of advice upon parting, and I haven’t done enough of it myself, so I thought it important to do for you as you embark on your new journey. I don’t know if I’ll ever do this again! I probably won’t get this right, but I believe this effort might be valuable to both of us.
In considering what you’re about to take on, I believe it’s best to highlight some challenges you’ll likely face. I have no doubt you’ll be able to overcome all.

  1. Allow yourself to fail in public

We’ve talked about pushing yourself to take more risks, to be more creative, and question the traditional path. You won’t be successful at any of those unless you allow yourself to fail in the eyes of others. Risk, creativity, and defining your own path is made possible only through a series of failures, some big, some small. Hide none of them. Show all of them! Take pride in your ability to recognize them faster and better than anyone else, and your drive to learn from them to improve yourself.

  1. Don’t take things personally

Life is short. Remind yourself of this with every single thing you do. It will be hard to keep this in mind, I certainly struggle with it, but leading with this understanding puts what matters most into view. It’s not about you. It’s about what you contribute. Most people won’t understand it while you’re doing it. They may express hate towards you along the way! If you take this as a reflection of yourself, you’ll stall. If you approach instead with empathy, and decide to use it, you’ll keep moving, and do more than you think you’re able.

  1. The work matters most.

We can’t do much meaningful work without other people. It’s right to put them first. Yet we must remember why they’re with us: to contribute to something bigger than themselves. It’s critical we articulate a clear purpose and story that we can share and serve. Coaching people to serve that purpose better everyday is your job. They will look to you not to make decisions, but for guidance on how to make more informed decisions. They will want you to challenge them to reach levels they may not consider possible. They are with you to work with you. It’s their work that matters most. Everything else follows.

I’ve failed at all three of these. It’s never easy. If you could only focus on one of these, I’d suggest the first. It’s the one that will enable your greatest learning and improvement, and will drive your greatest contributions.

Thank you Sarah. I’ll miss our work together.


Thank you for this effort, Alex!

You beat me to it :slight_smile:

Paul - Who appreciates this letter even more after reading it in this format vs. Twitter. And realizes once again, why he’s not at all a fan of Twitter :slight_smile:


“Allow yourself to fail in public”

I could tell you a long winded story about when I finally was brave enough to take a chance in my life and open my first restaurant 20 years ago.

At that point in my life taking that jump off, I knew that even if I failed I would have landed on my feet because taking a risk like that for the first time, I would have considered that in itself a very big success.

A quote from the legendary jazz icon Miles Davis was my mantra.

“Don’t fear mistakes, there are none”.