10 Questions with Anna Counselman

Cofounder at Upstart

Anna Counselman in a Co-Founder at Upstart, an online lending platform that uses data and analytics to finance borrowers based on signals of their potential. Anna co-founded Upstart after 5 years at Google, where she ran Gmail Consumer Operations as it scaled from 150 million to 450 million users and launched the global Enterprise Customer Programs team. Previously, Anna held a variety of operations roles at McMaster Carr and several startups.

Anna graduated Summa Cum Laude from Boston University with a BA in Finance and Entrepreneurship. She received a White House Champion of Change award and was named by Silicon Valley Business Journal as Top 40 under 40.

  1. When did you know you wanted to be in tech?

I’m a business person in tech so my path was a little different. In college I thought I wanted to be a lawyer, so I took a cyberlaw class and we were learning about the Napster case. I was really intrigued by the idea that this technology threatened the disruption of an entire industry. There was tremendous power and potential in that. A few years later I started working at Google — and I’ve never looked back.

2. Who’s your idol?

My mom. She’s the most fearless and inspiring person I know. Back when we lived in Moscow, she founded the first and only private boys and girls club, and it let her employ all these amazing artists, scientists, mathematicians, etc. that had fallen out of favor with the communist party.

When she moved to America in her early 40s, she decided that computers were the future and threw herself into studying Java and C++. I’ve never met anyone with more determination and resolve to make the most of any situation she’s in.

3. What technology gets you excited?

Uber and self-driving cars. I cannot wait to turn in my car keys for my car-as-a-service membership. And I’m really excited for all the parking lots we can turn into public parks.

4. What’s a big challenge you’ve faced in your career journey, and how have you dealt with it?

Launching our loan product while launching my other startup — my son Tristan. There was about a 3-month period of my life where everything was a blur. I just remember this mantra that one of my Google mentors kept telling me — ‘It gets easier, it gets easier.’ And it did. As a result, I have this dream job at my startup and a really awesome kid at home. I wouldn’t trade either for the world.

5. When’s a time you felt immense pride in your work?

Every time I read a review from one of our borrowers. Our customers come to us when they feel like they’re never going to get control over their finances, that they’re being crushed by high-interest credit card debt and see no way out of it. It’s so rewarding to watch somebody get on a path to financial fitness so they can pursue their other life goals — getting married, moving, starting a new job, whatever it is.

6. What’s something you want to get better at?

Cooking. I’m pretty useless in the kitchen so my husband does most of the cooking in our household. I’d like to get beyond pancakes and mac and cheese.

7. Where’s your happy place?

Hanging out with my 2-year-old when he’s in a good mood and doing yoga when he’s not.

8. Best book you’ve ever read?

“The Power of Habit” — I’m a bit of a self-improvement junkie and building new habits is one of the most powerful ways to transform yourself.

9. If you could try another job for a day, what would it be?

I would love to sing in a band for a day. I have zero vocal talent, but if I could wave a magic wand that’s what I’d do.

10. If you could give your 18-year-old self any advice, what would it be?

Don’t worry about having a grand plan. Life will surprise you in the most unpredictable ways. Just think of every opportunity as a chance to prove how good you are, and new doors will always open up. Oh, and buy some Apple stock as soon as you can.