May 9th

I try to read the Bible in the morning. I’m not a disciplinarian about it but I’ll do it when I can, for as long as I’m able to. On May 9th, I happened to be in the Bible in the book of Romans. I read the following:

Not only that, but we rejoice in our sufferings, knowing that suffering produces endurance, and endurance produces character, and character produces hope, and hope does not put us to shame…. (Romans 5:3-5)

When I read that, it was around 1130am PST. I thought – wow that is a cool verse. I inked an “A-men!” on the margin next to it. What I didn’t know was that two hours later, Upstart stock would be down 56% due to an earnings report. As I write this, Upstart is now trading at around $30, down 90% from its high last year of $390.

If you’re reading this, it’s because you also lost something. I’m sure it was money, but it was probably something else too. Maybe it was the down payment for a house you’ve been planning to buy. Maybe a new car. Whatever it was, I’m sure it was real and that you are hurting a lot. I spent 6 years of my life building a company and have now seen most of the economics from that disappear. I’m one of the lucky ones. Some of you had options and not restricted stock.

What I also want to share with you is that you’ve also gained something. It may not feel like it right now. This is not an “everything in life happens for a reason” statement, although I do believe that. This is a “you are now a person of higher character” statement. I think this is important to mention, because unlike your money, your character cannot be taken away from you.

If you’ve experienced a great loss in your life (and I’m sure you have), you know what I’m talking about better than I can put into words. For the rest of your life, you’ll be able to speak from a place of greater humility and authenticity. You gained something – maybe not equal to what you lost but certainly valuable in a different sort of way. I hope that wherever you are in this remote-first world, you are experiencing at least some of this life after death.

As a final note, I also want to say something radical. Losing everything could be the best thing that ever happened to you. At least it was for me. When I left Dropbox to start Prodigy, I was in such financial distress that my roommate approached me and asked me if I’d be able to make rent and that otherwise, he’d be kicking me out of the apartment. Without that experience, I wouldn’t be here today writing to you.

My radical hope – is that something better will happen to you. I hope that someday, you too will be able to say that losing everything was the best thing that ever happened to you.


Now read this


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