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Two Cherubs by Raffaello Sanzio Raphael, 1512

I started angel investing in 2018 and have made 23 investments to date. Here’s an overview of my approach to investing and what I’ve learned so far.

How did I start angel investing?

I didn’t give investing much thought when I moved to the Bay Area 6 years ago — I was here to join a startup and build something valuable. But that changed when I became Chief of Staff to Opendoor CEO Eric Wu. Eric shared pitch decks, introduced me to other angels, and we chatted through the business models and technologies he was looking at. While discussions were theoretical at first — I wasn’t asking myself “would I invest my own money in this?” — my outlook slowly started to change as I thought to myself “this is super interesting” and “I could do this too.” …


I served as Chief of Staff to the CEO at Opendoor as we scaled from 200 to 800 employees in a year. Here’s an overview of the role, when and why the role is valuable, and how to make it a success for both the Chief of Staff and the executive.

This post includes 3 parts:

  • Part 1: Overview of the Chief of Staff role
  • Part 2: FAQs for potential Chiefs of Staff
  • Part 3: FAQs for executives considering hiring a Chief of Staff
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Before working at Google and Facebook, Sheryl Sandberg was Chief of Staff to US Treasury Secretary Larry Summers

Part 1: Overview of the Chief of Staff Role

What is a Chief of Staff?

A Chief of Staff is the right-hand person and force-multiplier to an executive, often the CEO. This can mean many things depending on the needs of the company and executive, and can change over time, but typically encompasses managing the executive’s priorities, overseeing staff/internal operations, and spearheading special projects. …


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I left Bain to join seed-stage Opendoor in 2014. For those making the transition to the startup world, here are some thoughts based on my experience.

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Opendoor’s Open House signs in front of a home for sale

1. Educate yourself on the startup world

Startups and consulting firms are worlds apart in what their priorities are, how they operate, and what they’re like to work at. Learn as much as you can before applying for jobs. …

About

Julia DeWahl

Angel investor. Formerly Opendoor and Bain. Loves skiing and dinner parties.

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