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20 Questions

This Successful Entrepreneur Shares The Trick That Helps Her Tell The Difference Between Being Productive and Being Busy

Tradesy founder and CEO Tracy DiNunzio swears by relentless list making.
This Successful Entrepreneur Shares The Trick That Helps Her Tell The Difference Between Being Productive and Being Busy
Image credit: Courtesy of Tracy DiNunzio
Entrepreneur Staff
10 min read

Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

In 2012, Tracy DiNunzio looked at her closet and knew that something had to change.

It was messy and filled with items that she once cherished but simply wouldn’t wear anymore. She figured that there had be some other women out there who would enjoy and take good care of her things -- and probably had the same issues she did.

The fine artist-turned-entrepreneur decided to pursue the idea of building a platform that would allow people to sell their old goods and shop in someone else’s closet.

DiNunzio bootstrapped the company at the beginning by renting her bedroom on Airbnb, sleeping on the couch and working at her kitchen table. The hard work paid off.

Over the last five years, the peer-to-peer resale marketplace has grown from a staff of seven in DiNunzio’s home to 100 employees at the company’s Santa Monica, Calif. Headquarters. And with nearly $75 million in funding, including from Richard Branson, the company shows no sign of slowing down.

We caught up with DiNunzio to ask her 20 Questions and find out what makes her tick.

Related: The Founder of Bumble Reveals How the 'Question of Nine' Can Help You Stay Focused

1. How do you start your day?
I start my day with coffee and emails. I like to give myself a little time to wake up and clear my inbox, so I can start the day fresh. Then I get ready for work while listening to NPR, so I'm all caught up on the news.

2. How do you end your day?
After I have wrapped up work for the day, I go home, eat dinner and think about our company strategy and how the team is doing. To settle down into a mode where I can reflect well, I do these very complicated jigsaw puzzles. I look for the ones that are the hardest -- the harder it is, the more it lets me get absorbed and think on a deeper level. My house looks like a 12 year old lives there, but it works for me.

3. What’s a book that changed your mind and why?
I read Sapiens by Yuval Noah Harari twice. It broadened my view of everything from human behavior to how industry formed and how we got here today. I think more than anything it contextualizes modern life against the backdrop of the larger human history. To me it felt like it brought wisdom into my life that I didn't have before I read it.

4. What’s a book you always recommend and why?
Elon Musk by Ashlee Vance. For me, Elon Musk is our greatest living entrepreneur. And his story is both inspiring and practical for any entrepreneur. Normally the only people that look for book recommendations are entrepreneurs. So, I've been recommending and giving away copies since it came out.

I'm also been recommending a book called By Invitation Only: How We Built Gilt and Changed the Way Millions Shop by Alexis Maybank and Alexandra Wilkis Wilson. I  recommend it to any commerce-oriented founders and entrepreneurs, because it's an amazingly rich story of how Alexander and Alexis, the co-founders of Gilt Groupe, really transformed shopping in a very short period of time.

Related: Use This Founder's Top Tip To Make Your Meetings Work For You

5. What’s a strategy to keep focused?
There are two sides to staying focused. One is to figure out how you find your way to your own flow state. To get really absorbed in that specific piece of work and spend hours inside of it. Mine is about a certain amount of privacy, about having my schedule cleared. I like to be in a public place, but in a private part of the public space. 

The complete flip side of that you also need to master the art of quickly switching gears. So I keep copious lists that allow me to switch between tasks without forgetting or losing things that I know I have to come back to. If you just write down everything you've done and need to do then you know you're not losing the thread and can jump to the next one quite quickly.

6. When you were a kid what did you want to be when you grew up?
An artist. It was all I ever wanted to be, and that’s what I was until I started Tradesy.

7. What did you learn from the worst boss you ever had?
I've never really had a boss. But what I've learned from observing people being bosses within our company is just how much we all influence each other and how careful a leader has to be with how they choose their words. It is a tremendous responsibility to be someone's boss, to say what you mean and mean what you say and be thoughtful about your words.

8. Who has influenced you most when it comes to how you approach your work?
John Doerr [an investor], who is on our board. He is just an incredible, remarkable leader who has figured out how to scale himself in ways that I've not seen up close with anybody else. I think that he has influenced me to let go and learn how to scale -- meaning let other people do the work and keep offloading things you used to do so that you can gain more capacity.

9. What’s a trip that changed you?
I went to Mexico and ended up staying to get my master's degree in fine arts. I was there for over three years. It was supposed to be a short trip that turned into a pretty long one. And when I came back from Mexico, the difference in how we treated objects shocked me. There is less of a disposable culture there -- you don't throw things away. That really inspired me to start Tradesy.

Related: This Introvert Founder Swears by This Management Tip

10. What inspires you?
Our customers and team. I don't know how I got so lucky to have them all in my life. I think knowing that we're touching millions of women and making their lives a little easier, a little more affordable, empowering them to look and feel the way they want is endlessly inspiring.

And then watching our team learn and grow, get better, get stronger and be the talented and incredible people they are, just makes it exciting to come to work every day.

11. What was your first business idea and what did you do with it?
Tradesy was my first business idea. I know a lot of entrepreneurs scaled a lemonade stand at the age of 12 but that wasn't me. I came from a much more creative place. All of my projects were about making art.

12. What was an early job that taught you something important or useful?
I worked my way through high school and college waiting tables and bartending. I learned that people are mean when they're hungry and nice when they are drinking.]

Also, I learned that in any group -- where they are people going out to dinner or a group of investors -- there tends to be an alpha, a beta and a detractor. If you can identify who those people are within a group, it's a little bit easier to get the result you want.

13. What’s the best advice you ever took?
Somebody told me very early on when I was starting Tradesy is that the only reason any business ever fails is because it runs out of money. And as a founder/CEO, my job is to keep fuel in the tank. If the business is a bus, the only reason that the bus is going to stop is if it runs out of fuel. That's how every business ends eventually. It's easy sometimes when you're focused on other parts of the business as a leader to forget that very basic common principle.

 

14. What's the worst piece of advice you ever got?
More than one investor that I pitched in the early stage commented on my appearance and told me I needed to look more like that of a fashion founder, rather than showing up for meetings looking like I spent three days straight at my computer, which is what I was doing at that time. That was terrible advice. What you look like has absolutely nothing to do with the quality of your work or the validity of your pitch. I think anyone who thinks it does is probably not worthy of being your investor or partner.

Related: Use This Successful Entrepreneur's Scheduling Secret to Have Your Most Productive Day

15. What’s a productivity tip you swear by?
Relentless list-making. I tend to re-prioritize my list about three times a day. So I'll take 10 minutes and ask myself With what I know now, what's the most important thing on this list? What's the most urgent thing on this list? As you grow as an entrepreneur and there are more moving pieces, in order to remain productive and not just busy, you absolutely have to pause to prioritize with more frequency.

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I use tool called notebook on [the Tradesy] app that lets you create multiple different books of notes and lists. I find that super useful.

For workflows, there are a lot of fancy solutions, but we find that Google Docs is the absolute best and most flexible way to keep track of stacks of documents, share and collaborate.

17. What does work-life balance mean to you?
I’m still figuring that out, but I think it means more work-life integration. Being able to take vacations but do some work when you’re on them. Or take breaks while working to do things that feel leisurely. But in all honesty this area is not something I've yet mastered.

18. How do you prevent burnout?
You know what people say about doctors: their lives are not their own because they are always on call.

And that's true for CEO and founders. So I can't always prevent burnout, but I've learned how to quickly recover from burnout with a combination of meditation and for me, a short trip to the desert, to Palm Springs, is healing.  

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
To make art. This is something my co-founder Sash Catanzarite also believes in deeply. In our office, we have a lot of art-making tools, so if anyone feels blocked, they can go paint or build a lego set.

20. What are you learning now? Why is that important?
I’m learning to meditate and a little bit of self-hypnosis. It’s important because when you’re focused a lot on mastery and achievement, as I have been with my work, you can forget that there there is a whole other area of life that can be equally or even more fulfilling. I'm a very humble meditation student. I'm terrible at it so far, but I keep at it, because I believe in its value.

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