notebooks at the dining table, organizing his thoughts and to-dos. I have some of this note-taking discipline in me. I love this quotation from Lee Iacocca: “The discipline of writing something down is the first step toward making it happen.”
X: What career advice do you give to new college graduates?
R.A.: Optimize your choice of what you do for growth and learning, not only for money or perks or convenience. One way to maximize growth and learning comes from joining a mid-stage startup. Another way to do this is select what you do based on the boss or leader that you think you’ll learn the most from.
X: What’s your biggest failure as an entrepreneur or investor?
R.A.: As an investor in early stage startups, the companies that you missed investing in are your anti-portfolio. So, three companies in my anti-portfolio, companies that I saw and spent time with (all from my first YC demo day) but ultimately didn’t invest in: PlanGrid, FarmLogs, and Zapier.
X: What did you want to be when you were a kid?
R.A.: I don’t know if I ever thought about what I wanted to be when I grew up. I guess I thought I’d do something like my Dad, who was an engineer and ran a business he started. But I always had an interest in technology—I learned to write programs in BASIC and then Pascal in elementary school and middle school. I was into bulletin boards (BBSs) when I was 12 or 13. So I guess it’s not surprising that I ended up working in technology.
X: If you got stranded on a desert island, what’s the one thing you would have to have with you?
R.A.: My coffee setup. I love good coffee and start most days making myself a cappuccino at home with beans from either Houston-based Amaya Roasting Company or Oakland, CA-based Blue Bottle Coffee (I subscribe to one of their beans-by-mail subscriptions.) What’s that you say? The desert island doesn’t have electricity or potable water? Welp. I guess I’m screwed then!
